TY  - JOUR
AU  - Vujčić, Miroslava
AU  - Tufegdžić, Srđan
AU  - Novaković, Irena
AU  - Djikanovic, Daniela
AU  - Gašić, Miroslav J.
AU  - Sladić, Dušan
PY  - 2013
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1237
AB  - The interactions of avarone, a quinone from the marine sponge Dysideaavara, and the methylamino derivatives of avarone (2), 3'-(methylamino)avarone (3) and 4'-(methylamino)avarone (4) with calf thymus DNA (CT-DNA) were studied. Agarose gel electrophoreticanalysis showed that binding of the quinones quenched fluorescence of ethidium bromide (EB). The extent of fluorescence quenching of intercalator EB by competitive displacement from EB-CT-DNA system and of groove binder Hoechst 33258 (H) from H-CT-DNA system with the quinones was analyzed by fluorescence spectroscopy. The obtained results demonstrated that the quinones reduced binding of both the intercalator EB and the minor groove binder H, indicating possible degradation of DNA. The substituent on the quinone moiety determined the extent of DNA damaging effect of the quinone, which was the most extensive with 3'-(methylamino)avarone and the least extensive with its regioisomer 4'-(methylamino)avarone. The results were confirmed by the observed hyperchromic effects in UV-visible spectra measured after interactions of the derivatives with CT-DNA.
PB  - Elsevier
T2  - International Journal of Biological Macromolecules
T1  - Studies on the interactions of bioactive quinone avarone and its methylamino derivatives with calf thymus DNA
VL  - 62
SP  - 405
EP  - 410
DO  - 10.1016/j.ijbiomac.2013.09.013
ER  - 

@article{
author = "Vujčić, Miroslava and Tufegdžić, Srđan and Novaković, Irena and Djikanovic, Daniela and Gašić, Miroslav J. and Sladić, Dušan",
year = "2013",
abstract = "The interactions of avarone, a quinone from the marine sponge Dysideaavara, and the methylamino derivatives of avarone (2), 3'-(methylamino)avarone (3) and 4'-(methylamino)avarone (4) with calf thymus DNA (CT-DNA) were studied. Agarose gel electrophoreticanalysis showed that binding of the quinones quenched fluorescence of ethidium bromide (EB). The extent of fluorescence quenching of intercalator EB by competitive displacement from EB-CT-DNA system and of groove binder Hoechst 33258 (H) from H-CT-DNA system with the quinones was analyzed by fluorescence spectroscopy. The obtained results demonstrated that the quinones reduced binding of both the intercalator EB and the minor groove binder H, indicating possible degradation of DNA. The substituent on the quinone moiety determined the extent of DNA damaging effect of the quinone, which was the most extensive with 3'-(methylamino)avarone and the least extensive with its regioisomer 4'-(methylamino)avarone. The results were confirmed by the observed hyperchromic effects in UV-visible spectra measured after interactions of the derivatives with CT-DNA.",
publisher = "Elsevier",
journal = "International Journal of Biological Macromolecules",
title = "Studies on the interactions of bioactive quinone avarone and its methylamino derivatives with calf thymus DNA",
volume = "62",
pages = "405-410",
doi = "10.1016/j.ijbiomac.2013.09.013"
}

Vujčić, M., Tufegdžić, S., Novaković, I., Djikanovic, D., Gašić, M. J.,& Sladić, D.. (2013). Studies on the interactions of bioactive quinone avarone and its methylamino derivatives with calf thymus DNA. in International Journal of Biological Macromolecules
Elsevier., 62, 405-410.
https://doi.org/10.1016/j.ijbiomac.2013.09.013

Vujčić M, Tufegdžić S, Novaković I, Djikanovic D, Gašić MJ, Sladić D. Studies on the interactions of bioactive quinone avarone and its methylamino derivatives with calf thymus DNA. in International Journal of Biological Macromolecules. 2013;62:405-410.
doi:10.1016/j.ijbiomac.2013.09.013 .

Vujčić, Miroslava, Tufegdžić, Srđan, Novaković, Irena, Djikanovic, Daniela, Gašić, Miroslav J., Sladić, Dušan, "Studies on the interactions of bioactive quinone avarone and its methylamino derivatives with calf thymus DNA" in International Journal of Biological Macromolecules, 62 (2013):405-410,
https://doi.org/10.1016/j.ijbiomac.2013.09.013 . .

TY  - JOUR
AU  - Novaković, Irena
AU  - Anđelković, Uroš
AU  - Zlatović, Mario
AU  - Gašić, Miroslav J.
AU  - Sladić, Dušan
PY  - 2012
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1005
AB  - A conjugate of lysozyme with avarone, a bioactive sesquiterpene quinone of marine origin, and its three derivatives were synthesized. MALDI TOF mass spectral analysis and tryptic digestion showed that the only residue in lysozyme that was modified by all derivatives was lysine 97. The identity of the residue was in full correlation with the prediction obtained by molecular modeling. All bioconjugates preserved most of the enzymatic activity of lysozyme. The melting point of the conjugates was slightly increased in comparison to lysozyme, indicating a slight stabilization of structure. The antibacterial activity of all the conjugates to both Gram positive and Gram negative bacteria was stronger than the activity of either lysozyme or the quinones, the MIC values being in low micromolar range for some conjugates.
PB  - American Chemical Society (ACS)
T2  - Bioconjugate Chemistry
T1  - Bioconjugate of Lysozyme and the Antibacterial Marine Sesquiterpene Quinone Avarone and Its Derivatives
VL  - 23
IS  - 1
SP  - 57
EP  - 65
DO  - 10.1021/bc200330m
ER  - 

@article{
author = "Novaković, Irena and Anđelković, Uroš and Zlatović, Mario and Gašić, Miroslav J. and Sladić, Dušan",
year = "2012",
abstract = "A conjugate of lysozyme with avarone, a bioactive sesquiterpene quinone of marine origin, and its three derivatives were synthesized. MALDI TOF mass spectral analysis and tryptic digestion showed that the only residue in lysozyme that was modified by all derivatives was lysine 97. The identity of the residue was in full correlation with the prediction obtained by molecular modeling. All bioconjugates preserved most of the enzymatic activity of lysozyme. The melting point of the conjugates was slightly increased in comparison to lysozyme, indicating a slight stabilization of structure. The antibacterial activity of all the conjugates to both Gram positive and Gram negative bacteria was stronger than the activity of either lysozyme or the quinones, the MIC values being in low micromolar range for some conjugates.",
publisher = "American Chemical Society (ACS)",
journal = "Bioconjugate Chemistry",
title = "Bioconjugate of Lysozyme and the Antibacterial Marine Sesquiterpene Quinone Avarone and Its Derivatives",
volume = "23",
number = "1",
pages = "57-65",
doi = "10.1021/bc200330m"
}

Novaković, I., Anđelković, U., Zlatović, M., Gašić, M. J.,& Sladić, D.. (2012). Bioconjugate of Lysozyme and the Antibacterial Marine Sesquiterpene Quinone Avarone and Its Derivatives. in Bioconjugate Chemistry
American Chemical Society (ACS)., 23(1), 57-65.
https://doi.org/10.1021/bc200330m

Novaković I, Anđelković U, Zlatović M, Gašić MJ, Sladić D. Bioconjugate of Lysozyme and the Antibacterial Marine Sesquiterpene Quinone Avarone and Its Derivatives. in Bioconjugate Chemistry. 2012;23(1):57-65.
doi:10.1021/bc200330m .

Novaković, Irena, Anđelković, Uroš, Zlatović, Mario, Gašić, Miroslav J., Sladić, Dušan, "Bioconjugate of Lysozyme and the Antibacterial Marine Sesquiterpene Quinone Avarone and Its Derivatives" in Bioconjugate Chemistry, 23, no. 1 (2012):57-65,
https://doi.org/10.1021/bc200330m . .

TY  - JOUR
AU  - Božić, Tatjana T.
AU  - Novaković, Irena
AU  - Gašić, Miroslav J.
AU  - Juranić, Zorica
AU  - Stanojković, Tatjana
AU  - Tufegdžić, Srđan
AU  - Kljajić, Zoran
AU  - Sladić, Dušan
PY  - 2010
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/730
AB  - Nine alkyl(aryl)thio derivatives of the marine sesquiterpene quinone avarone were synthesized by nucleophilic addition of thiols or thiophenol to avarone. In most cases only one regioisomer was obtained. Their cytotoxic activities, brine shrimp lethality and antibacterial activity were evaluated, as well as those of some previously synthesized avarone derivatives. Anti-HIV activity of two derivatives was tested. Electrochemical properties were determined for all the derivatives in Order to obtain more accurate information on structure-activity relationships. Most derivatives showed cytotoxic activity against tumor cell lines, with IC50 values less than 10 mu M for some of them, in particular those with electron-donating substituents. The most active Compound was 4'-(methylamino)avarone, with IC50 value of 2.4 mu M to melanoma Fem-X cells, and no cytotoxicity to normal lymphocytes.
PB  - Elsevier France-Editions Scientifiques Medicales Elsevier, Paris
T2  - European Journal of Medicinal Chemistry
T1  - Synthesis and biological activity of derivatives of the marine quinone avarone
VL  - 45
IS  - 3
SP  - 923
EP  - 929
DO  - 10.1016/j.ejmech.2009.11.033
ER  - 

@article{
author = "Božić, Tatjana T. and Novaković, Irena and Gašić, Miroslav J. and Juranić, Zorica and Stanojković, Tatjana and Tufegdžić, Srđan and Kljajić, Zoran and Sladić, Dušan",
year = "2010",
abstract = "Nine alkyl(aryl)thio derivatives of the marine sesquiterpene quinone avarone were synthesized by nucleophilic addition of thiols or thiophenol to avarone. In most cases only one regioisomer was obtained. Their cytotoxic activities, brine shrimp lethality and antibacterial activity were evaluated, as well as those of some previously synthesized avarone derivatives. Anti-HIV activity of two derivatives was tested. Electrochemical properties were determined for all the derivatives in Order to obtain more accurate information on structure-activity relationships. Most derivatives showed cytotoxic activity against tumor cell lines, with IC50 values less than 10 mu M for some of them, in particular those with electron-donating substituents. The most active Compound was 4'-(methylamino)avarone, with IC50 value of 2.4 mu M to melanoma Fem-X cells, and no cytotoxicity to normal lymphocytes.",
publisher = "Elsevier France-Editions Scientifiques Medicales Elsevier, Paris",
journal = "European Journal of Medicinal Chemistry",
title = "Synthesis and biological activity of derivatives of the marine quinone avarone",
volume = "45",
number = "3",
pages = "923-929",
doi = "10.1016/j.ejmech.2009.11.033"
}

Božić, T. T., Novaković, I., Gašić, M. J., Juranić, Z., Stanojković, T., Tufegdžić, S., Kljajić, Z.,& Sladić, D.. (2010). Synthesis and biological activity of derivatives of the marine quinone avarone. in European Journal of Medicinal Chemistry
Elsevier France-Editions Scientifiques Medicales Elsevier, Paris., 45(3), 923-929.
https://doi.org/10.1016/j.ejmech.2009.11.033

Božić TT, Novaković I, Gašić MJ, Juranić Z, Stanojković T, Tufegdžić S, Kljajić Z, Sladić D. Synthesis and biological activity of derivatives of the marine quinone avarone. in European Journal of Medicinal Chemistry. 2010;45(3):923-929.
doi:10.1016/j.ejmech.2009.11.033 .

Božić, Tatjana T., Novaković, Irena, Gašić, Miroslav J., Juranić, Zorica, Stanojković, Tatjana, Tufegdžić, Srđan, Kljajić, Zoran, Sladić, Dušan, "Synthesis and biological activity of derivatives of the marine quinone avarone" in European Journal of Medicinal Chemistry, 45, no. 3 (2010):923-929,
https://doi.org/10.1016/j.ejmech.2009.11.033 . .

TY  - JOUR
AU  - Milić, Dragana
AU  - Kop, Tatjana
AU  - Csanadi, J.
AU  - Juranić, Zorica
AU  - Žižak, Željko
AU  - Gašić, Miroslav J.
AU  - Šolaja, Bogdan
PY  - 2009
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/618
AB  - A simple approach to a stable steroidal estrone derived A,B-spiro system is reported. Treatment of estrone derived A-ring diepoxyalcohol with the Ac2O-TMSOTf system at the ambient temperature led to acetylation, while at the reflux temperature the acid-catalysed rearrangement took place affording the spiro-compound. Results of extensive in vitro and in vivo anticancer tests on the diepoxide, as well as preliminary data on the antiproliferative activity of the spiro-product against three cancer cell lines, are also presented.
PB  - Elsevier Science Inc, New York
T2  - Steroids
T1  - Estrone derived steroidal diepoxide: Biologically active compound and precursor of a stable steroidal A,B-spiro system
VL  - 74
IS  - 12
SP  - 890
EP  - 895
DO  - 10.1016/j.steroids.2009.06.002
ER  - 

@article{
author = "Milić, Dragana and Kop, Tatjana and Csanadi, J. and Juranić, Zorica and Žižak, Željko and Gašić, Miroslav J. and Šolaja, Bogdan",
year = "2009",
abstract = "A simple approach to a stable steroidal estrone derived A,B-spiro system is reported. Treatment of estrone derived A-ring diepoxyalcohol with the Ac2O-TMSOTf system at the ambient temperature led to acetylation, while at the reflux temperature the acid-catalysed rearrangement took place affording the spiro-compound. Results of extensive in vitro and in vivo anticancer tests on the diepoxide, as well as preliminary data on the antiproliferative activity of the spiro-product against three cancer cell lines, are also presented.",
publisher = "Elsevier Science Inc, New York",
journal = "Steroids",
title = "Estrone derived steroidal diepoxide: Biologically active compound and precursor of a stable steroidal A,B-spiro system",
volume = "74",
number = "12",
pages = "890-895",
doi = "10.1016/j.steroids.2009.06.002"
}

Milić, D., Kop, T., Csanadi, J., Juranić, Z., Žižak, Ž., Gašić, M. J.,& Šolaja, B.. (2009). Estrone derived steroidal diepoxide: Biologically active compound and precursor of a stable steroidal A,B-spiro system. in Steroids
Elsevier Science Inc, New York., 74(12), 890-895.
https://doi.org/10.1016/j.steroids.2009.06.002

Milić D, Kop T, Csanadi J, Juranić Z, Žižak Ž, Gašić MJ, Šolaja B. Estrone derived steroidal diepoxide: Biologically active compound and precursor of a stable steroidal A,B-spiro system. in Steroids. 2009;74(12):890-895.
doi:10.1016/j.steroids.2009.06.002 .

Milić, Dragana, Kop, Tatjana, Csanadi, J., Juranić, Zorica, Žižak, Željko, Gašić, Miroslav J., Šolaja, Bogdan, "Estrone derived steroidal diepoxide: Biologically active compound and precursor of a stable steroidal A,B-spiro system" in Steroids, 74, no. 12 (2009):890-895,
https://doi.org/10.1016/j.steroids.2009.06.002 . .

TY  - JOUR
AU  - Tsoukatou, M.
AU  - Maréchal, J.P.
AU  - Hellio, C.
AU  - Novaković, Irena
AU  - Tufegdžić, Srđan
AU  - Sladić, Dušan
AU  - Gašić, Miroslav J.
AU  - Clare, A.S.
AU  - Vagias, C.
AU  - Roussis, V.
PY  - 2007
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/359
AB  - The sesquiterpene hydroquinone avarol (1) was isolated from the marine sponge Dysidea avara, whereas the corresponding quinone, avarone (2), was obtained by oxidation of avarol, and the significantly more lipophilic compounds [3′-(p-chlorophenyl) avarone (3), 3′,4′-ethylenedithioavarone (4), 4′-isopropylthioavarone (5), 4′-tert-butylthioavarone (6), 4′-propylthioavarone (7), 4′-octylthioavarone (8)] were obtained by nucleophilic addition of thiols or p-chloroaniline to avarone. All these compounds were tested, at concentrations ranging from 0.5 to 50 μg/mL, for their effect on the settlement of the cyprid stage of Balanus amphitrite, for toxicity to both nauplii and cyprids and for their growth inhibitory activity on marine bacteria (Cobetia marina, Marinobacterium stanieri, Vibrio fischeri and Pseudoalteromonas haloplanktis) and marine fungi (Halosphaeriopsis mediosetigera, Asteromyces cruciatus, Lulworthia uniseptata and Monodictys pelagica).
PB  - MDPI
T2  - Molecules
T1  - Evaluation of the activity of the sponge metabolites avarol and avarone and their synthetic derivatives against fouling micro- and macroorganisms
VL  - 12
IS  - 5
SP  - 1022
EP  - 1034
DO  - 10.3390/12051022
ER  - 

@article{
author = "Tsoukatou, M. and Maréchal, J.P. and Hellio, C. and Novaković, Irena and Tufegdžić, Srđan and Sladić, Dušan and Gašić, Miroslav J. and Clare, A.S. and Vagias, C. and Roussis, V.",
year = "2007",
abstract = "The sesquiterpene hydroquinone avarol (1) was isolated from the marine sponge Dysidea avara, whereas the corresponding quinone, avarone (2), was obtained by oxidation of avarol, and the significantly more lipophilic compounds [3′-(p-chlorophenyl) avarone (3), 3′,4′-ethylenedithioavarone (4), 4′-isopropylthioavarone (5), 4′-tert-butylthioavarone (6), 4′-propylthioavarone (7), 4′-octylthioavarone (8)] were obtained by nucleophilic addition of thiols or p-chloroaniline to avarone. All these compounds were tested, at concentrations ranging from 0.5 to 50 μg/mL, for their effect on the settlement of the cyprid stage of Balanus amphitrite, for toxicity to both nauplii and cyprids and for their growth inhibitory activity on marine bacteria (Cobetia marina, Marinobacterium stanieri, Vibrio fischeri and Pseudoalteromonas haloplanktis) and marine fungi (Halosphaeriopsis mediosetigera, Asteromyces cruciatus, Lulworthia uniseptata and Monodictys pelagica).",
publisher = "MDPI",
journal = "Molecules",
title = "Evaluation of the activity of the sponge metabolites avarol and avarone and their synthetic derivatives against fouling micro- and macroorganisms",
volume = "12",
number = "5",
pages = "1022-1034",
doi = "10.3390/12051022"
}

Tsoukatou, M., Maréchal, J.P., Hellio, C., Novaković, I., Tufegdžić, S., Sladić, D., Gašić, M. J., Clare, A.S., Vagias, C.,& Roussis, V.. (2007). Evaluation of the activity of the sponge metabolites avarol and avarone and their synthetic derivatives against fouling micro- and macroorganisms. in Molecules
MDPI., 12(5), 1022-1034.
https://doi.org/10.3390/12051022

Tsoukatou M, Maréchal J, Hellio C, Novaković I, Tufegdžić S, Sladić D, Gašić MJ, Clare A, Vagias C, Roussis V. Evaluation of the activity of the sponge metabolites avarol and avarone and their synthetic derivatives against fouling micro- and macroorganisms. in Molecules. 2007;12(5):1022-1034.
doi:10.3390/12051022 .

Tsoukatou, M., Maréchal, J.P., Hellio, C., Novaković, Irena, Tufegdžić, Srđan, Sladić, Dušan, Gašić, Miroslav J., Clare, A.S., Vagias, C., Roussis, V., "Evaluation of the activity of the sponge metabolites avarol and avarone and their synthetic derivatives against fouling micro- and macroorganisms" in Molecules, 12, no. 5 (2007):1022-1034,
https://doi.org/10.3390/12051022 . .

TY  - JOUR
AU  - Vujčić, Miroslava
AU  - Tufegdžić, Srđan
AU  - Vujčić, Zoran
AU  - Gašić, Miroslav J.
AU  - Sladić, Dušan
PY  - 2007
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/302
AB  - Changes in electrophoresis pattern after interaction of supercoiled plasmid pBR322 DNA with avarol was studied at a micromolar concentration of reactants under mild reaction conditions. Interactions of avarol with linear high-molecular CT-DNA at millimolar concentrations were analyzed by electrophoresis and UV spectrophotometry. It was observed that avarol is capable of quenching ethidium bromide fluorescence in DNA bands. An increase in the absorbance of DNA was detected. The results indicate the binding of avarol to DNA and/or modification of nucleotide bases.
AB  - Proučavane su promene elektroforetskog ponašanja DNA posle interakcija superhelikoidalnog plazmida pBR322 s avarolom pri mikromolarnim koncentracijama reaktanata pod blagim reakcionim uslovima. Interakcije avarola sa linearnom visokomolekulskom CT-DNA pri milimolarnim koncentracijama analizirane su elektroforezom i UV spektrofotometrijom. Uočeno je da je avarol u stanju da gasi fluorescenciju etidijum-bromida u trakama koje potiču od DNA. Detektovan je porast apsorbancije DNA. Rezultati ukazuju na vezivanje avarona za DNA i/ili modifikaciju nukleotidnih baza.
PB  - Serbian Chemical Society
T2  - Journal of the Serbian Chemical Society
T1  - Interactions of the anti-tumor sesquiterpene hydroquinone avarol with DNA in vitro
T1  - Interakcije antitumorskog seskviterpenskog hidrohinona avarola sa DNA in vitro
VL  - 72
IS  - 12
SP  - 1265
EP  - 1269
DO  - 10.2298/JSC0712265V
ER  - 

@article{
author = "Vujčić, Miroslava and Tufegdžić, Srđan and Vujčić, Zoran and Gašić, Miroslav J. and Sladić, Dušan",
year = "2007",
abstract = "Changes in electrophoresis pattern after interaction of supercoiled plasmid pBR322 DNA with avarol was studied at a micromolar concentration of reactants under mild reaction conditions. Interactions of avarol with linear high-molecular CT-DNA at millimolar concentrations were analyzed by electrophoresis and UV spectrophotometry. It was observed that avarol is capable of quenching ethidium bromide fluorescence in DNA bands. An increase in the absorbance of DNA was detected. The results indicate the binding of avarol to DNA and/or modification of nucleotide bases., Proučavane su promene elektroforetskog ponašanja DNA posle interakcija superhelikoidalnog plazmida pBR322 s avarolom pri mikromolarnim koncentracijama reaktanata pod blagim reakcionim uslovima. Interakcije avarola sa linearnom visokomolekulskom CT-DNA pri milimolarnim koncentracijama analizirane su elektroforezom i UV spektrofotometrijom. Uočeno je da je avarol u stanju da gasi fluorescenciju etidijum-bromida u trakama koje potiču od DNA. Detektovan je porast apsorbancije DNA. Rezultati ukazuju na vezivanje avarona za DNA i/ili modifikaciju nukleotidnih baza.",
publisher = "Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "Interactions of the anti-tumor sesquiterpene hydroquinone avarol with DNA in vitro, Interakcije antitumorskog seskviterpenskog hidrohinona avarola sa DNA in vitro",
volume = "72",
number = "12",
pages = "1265-1269",
doi = "10.2298/JSC0712265V"
}

Vujčić, M., Tufegdžić, S., Vujčić, Z., Gašić, M. J.,& Sladić, D.. (2007). Interactions of the anti-tumor sesquiterpene hydroquinone avarol with DNA in vitro. in Journal of the Serbian Chemical Society
Serbian Chemical Society., 72(12), 1265-1269.
https://doi.org/10.2298/JSC0712265V

Vujčić M, Tufegdžić S, Vujčić Z, Gašić MJ, Sladić D. Interactions of the anti-tumor sesquiterpene hydroquinone avarol with DNA in vitro. in Journal of the Serbian Chemical Society. 2007;72(12):1265-1269.
doi:10.2298/JSC0712265V .

Vujčić, Miroslava, Tufegdžić, Srđan, Vujčić, Zoran, Gašić, Miroslav J., Sladić, Dušan, "Interactions of the anti-tumor sesquiterpene hydroquinone avarol with DNA in vitro" in Journal of the Serbian Chemical Society, 72, no. 12 (2007):1265-1269,
https://doi.org/10.2298/JSC0712265V . .

TY  - JOUR
AU  - Pajic, Ivana
AU  - Vujčić, Zoran
AU  - Vujčić, Miroslava
AU  - Novaković, Irena
AU  - Sladić, Dušan
AU  - Gašić, Miroslav J.
PY  - 2007
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/330
AB  - The quinone avarone, isolated from the marine sponge Dysidea avara, possesses the ability to chemically modify proteins. In this work, modification of lectin isolated from the coral Gerardia savaglia by avarone was examined. The techniques used for studying the modification were: SDS PAGE, isoelectric focusing and hemagglutination testing. The results of the SDS PAGE indicate dimerization of the protein. A shift of the pI toward lower value occurs upon modification. The change of the hemagglutination activity of the protein confirms that chemical modification of G. savaglia lectin by avarone changes its ability to interact with the membrane of erythrocytes.
AB  - Avaron, hinon izolovan iz morskog sunđera Dysidea avara, poseduje sposobnost da hemijski modifikuje proteine. U ovom radu ispitivana je modifikacija lektina izolovanog iz korala Gerardia savaglia avaronom. Tehnike za praćenje hemijske modifikacije bile su: SDS PAGE, izoelektrično fokusiranje i hemaglutinacioni test. Rezultati SDS PAGE upućuju na dimerizaciju proteina. Dolazi do pomeranja pI vrednosti proteina. Promena hemaglutinacione aktivnosti G. savaglia lektina avaronom uticala je na njegovu sposobnost interakcije sa membranom eritrocita.
PB  - Serbian Chemical Soc, Belgrade
T2  - Journal of the Serbian Chemical Society
T1  - Chemical modification of the lectin of the marine coral Gerardia savaglia by marine quinone avarone
T1  - Hemijske modifikacije lektina morskog korala Gerardia savaglia morskim hinonom avaronom
VL  - 72
IS  - 12
SP  - 1271
EP  - 1274
DO  - 10.2298/JSC0712271P
ER  - 

@article{
author = "Pajic, Ivana and Vujčić, Zoran and Vujčić, Miroslava and Novaković, Irena and Sladić, Dušan and Gašić, Miroslav J.",
year = "2007",
abstract = "The quinone avarone, isolated from the marine sponge Dysidea avara, possesses the ability to chemically modify proteins. In this work, modification of lectin isolated from the coral Gerardia savaglia by avarone was examined. The techniques used for studying the modification were: SDS PAGE, isoelectric focusing and hemagglutination testing. The results of the SDS PAGE indicate dimerization of the protein. A shift of the pI toward lower value occurs upon modification. The change of the hemagglutination activity of the protein confirms that chemical modification of G. savaglia lectin by avarone changes its ability to interact with the membrane of erythrocytes., Avaron, hinon izolovan iz morskog sunđera Dysidea avara, poseduje sposobnost da hemijski modifikuje proteine. U ovom radu ispitivana je modifikacija lektina izolovanog iz korala Gerardia savaglia avaronom. Tehnike za praćenje hemijske modifikacije bile su: SDS PAGE, izoelektrično fokusiranje i hemaglutinacioni test. Rezultati SDS PAGE upućuju na dimerizaciju proteina. Dolazi do pomeranja pI vrednosti proteina. Promena hemaglutinacione aktivnosti G. savaglia lektina avaronom uticala je na njegovu sposobnost interakcije sa membranom eritrocita.",
publisher = "Serbian Chemical Soc, Belgrade",
journal = "Journal of the Serbian Chemical Society",
title = "Chemical modification of the lectin of the marine coral Gerardia savaglia by marine quinone avarone, Hemijske modifikacije lektina morskog korala Gerardia savaglia morskim hinonom avaronom",
volume = "72",
number = "12",
pages = "1271-1274",
doi = "10.2298/JSC0712271P"
}

Pajic, I., Vujčić, Z., Vujčić, M., Novaković, I., Sladić, D.,& Gašić, M. J.. (2007). Chemical modification of the lectin of the marine coral Gerardia savaglia by marine quinone avarone. in Journal of the Serbian Chemical Society
Serbian Chemical Soc, Belgrade., 72(12), 1271-1274.
https://doi.org/10.2298/JSC0712271P

Pajic I, Vujčić Z, Vujčić M, Novaković I, Sladić D, Gašić MJ. Chemical modification of the lectin of the marine coral Gerardia savaglia by marine quinone avarone. in Journal of the Serbian Chemical Society. 2007;72(12):1271-1274.
doi:10.2298/JSC0712271P .

Pajic, Ivana, Vujčić, Zoran, Vujčić, Miroslava, Novaković, Irena, Sladić, Dušan, Gašić, Miroslav J., "Chemical modification of the lectin of the marine coral Gerardia savaglia by marine quinone avarone" in Journal of the Serbian Chemical Society, 72, no. 12 (2007):1271-1274,
https://doi.org/10.2298/JSC0712271P . .

TY  - CONF
AU  - Božić, Tatjana T.
AU  - Novaković, Irena
AU  - Gašić, Miroslav J.
AU  - Sladić, Dušan
PY  - 2005
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4171
AB  - In this work, inhibition of sulfhydryl containing glycolytic enzyme hexokinase by avarone and its derivatives was studied. The enzyme contains lysine and sulfhydryl residues, which can be modified by the quinone moiety. Our results show that avarone and its derivatives are capable of covalent modification of hexokinase.
PB  - Oxford : Blackwell Publishing
C3  - FEBS Journal / Federation of European of Biochemical Societies
T1  - Covalent modification of hexokinase by biologically active quinones
VL  - 272
SP  - 302
EP  - 302
UR  - https://hdl.handle.net/21.15107/rcub_cherry_752
ER  - 

@conference{
author = "Božić, Tatjana T. and Novaković, Irena and Gašić, Miroslav J. and Sladić, Dušan",
year = "2005",
abstract = "In this work, inhibition of sulfhydryl containing glycolytic enzyme hexokinase by avarone and its derivatives was studied. The enzyme contains lysine and sulfhydryl residues, which can be modified by the quinone moiety. Our results show that avarone and its derivatives are capable of covalent modification of hexokinase.",
publisher = "Oxford : Blackwell Publishing",
journal = "FEBS Journal / Federation of European of Biochemical Societies",
title = "Covalent modification of hexokinase by biologically active quinones",
volume = "272",
pages = "302-302",
url = "https://hdl.handle.net/21.15107/rcub_cherry_752"
}

Božić, T. T., Novaković, I., Gašić, M. J.,& Sladić, D.. (2005). Covalent modification of hexokinase by biologically active quinones. in FEBS Journal / Federation of European of Biochemical Societies
Oxford : Blackwell Publishing., 272, 302-302.
https://hdl.handle.net/21.15107/rcub_cherry_752

Božić TT, Novaković I, Gašić MJ, Sladić D. Covalent modification of hexokinase by biologically active quinones. in FEBS Journal / Federation of European of Biochemical Societies. 2005;272:302-302.
https://hdl.handle.net/21.15107/rcub_cherry_752 .

Božić, Tatjana T., Novaković, Irena, Gašić, Miroslav J., Sladić, Dušan, "Covalent modification of hexokinase by biologically active quinones" in FEBS Journal / Federation of European of Biochemical Societies, 272 (2005):302-302,
https://hdl.handle.net/21.15107/rcub_cherry_752 .

TY  - JOUR
AU  - Sladić, Dušan
AU  - Novaković, Irena
AU  - Vujčić, Zoran
AU  - Božić, Tatjana T.
AU  - Božić, Nataša
AU  - Milić, Dragana
AU  - Šolaja, Bogdan
AU  - Gašić, Miroslav J.
PY  - 2004
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/138
AB  - The avarone/avarol quinone/hydroquinone couple shows considerable antitumor activity. In this work, covalent modification of β-lactoglobulin by avarone and its derivatives as well as by the synthetic steroidal quinone 2,5(10)-estradiene- 1,4,17-trione and its derivatives were studied. The techniques for studying chemical modification of β-lactoglobulin by quinones were: UV/Vis spectrophotometry, SDS PAGE and isoelectrofocusing. SDS PAGE results suggest that polymerization of the protein occurs. It could be seen that the protein of 18 kD gives the bands of 20 kD, 36 kD, 40 kD, 45 kD, 64 kD and 128 kD depending on modification agent. The shift of the pI of the protein (5.4) upon modification toward lower values (from pI 5.0 to 5.3) indicated that lysine amino groups are the principal site of the reaction of β-lactoglobulin with the quinones.
AB  - Hinonsko/hidrohinonski par avaron/avarol pokazuje značajnu antitumorsku aktivnost. U ovom radu proučavane su kovalentne modifikacije β-laktoglobulina avaronom, sintetičkim steroidnim hinonom 2,5(10)-estradien-1,4,17-trionom i njihovim derivatima. Tehnike za praćenje hemijske modifikacije bile su: UV/Vis spektrofotometrija, SDS PAGE i izoelektrofokusiranje. Rezultati SDS PAGE ukazuju da se dešava polimerizacija proteina.Može se videti da protein od 18 kD daje trake od 20 kD, 36 kD, 40 kD, 45 kD, 64 kD i 128 kD u zavisnosti od agensa za modifikaciju. Pomeranje pI vrednosti proteina (5,4) nakon modifikacije ka nižim vrednostima (od pI 5,0 do 5,3) pokazuje da su amino-grupe lizina glavna mesta reakcije β-laktoglobulina sa hinonima.
PB  - Serbian Chemical Society
T2  - Journal of the Serbian Chemical Society
T1  - Protein covalent modification of biologically active quinones
T1  - Kovalentne modifikacije proteina biološki aktivnim hinonima
VL  - 69
IS  - 11
SP  - 901
EP  - 907
DO  - 10.2298/JSC0411901S
ER  - 

@article{
author = "Sladić, Dušan and Novaković, Irena and Vujčić, Zoran and Božić, Tatjana T. and Božić, Nataša and Milić, Dragana and Šolaja, Bogdan and Gašić, Miroslav J.",
year = "2004",
abstract = "The avarone/avarol quinone/hydroquinone couple shows considerable antitumor activity. In this work, covalent modification of β-lactoglobulin by avarone and its derivatives as well as by the synthetic steroidal quinone 2,5(10)-estradiene- 1,4,17-trione and its derivatives were studied. The techniques for studying chemical modification of β-lactoglobulin by quinones were: UV/Vis spectrophotometry, SDS PAGE and isoelectrofocusing. SDS PAGE results suggest that polymerization of the protein occurs. It could be seen that the protein of 18 kD gives the bands of 20 kD, 36 kD, 40 kD, 45 kD, 64 kD and 128 kD depending on modification agent. The shift of the pI of the protein (5.4) upon modification toward lower values (from pI 5.0 to 5.3) indicated that lysine amino groups are the principal site of the reaction of β-lactoglobulin with the quinones., Hinonsko/hidrohinonski par avaron/avarol pokazuje značajnu antitumorsku aktivnost. U ovom radu proučavane su kovalentne modifikacije β-laktoglobulina avaronom, sintetičkim steroidnim hinonom 2,5(10)-estradien-1,4,17-trionom i njihovim derivatima. Tehnike za praćenje hemijske modifikacije bile su: UV/Vis spektrofotometrija, SDS PAGE i izoelektrofokusiranje. Rezultati SDS PAGE ukazuju da se dešava polimerizacija proteina.Može se videti da protein od 18 kD daje trake od 20 kD, 36 kD, 40 kD, 45 kD, 64 kD i 128 kD u zavisnosti od agensa za modifikaciju. Pomeranje pI vrednosti proteina (5,4) nakon modifikacije ka nižim vrednostima (od pI 5,0 do 5,3) pokazuje da su amino-grupe lizina glavna mesta reakcije β-laktoglobulina sa hinonima.",
publisher = "Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "Protein covalent modification of biologically active quinones, Kovalentne modifikacije proteina biološki aktivnim hinonima",
volume = "69",
number = "11",
pages = "901-907",
doi = "10.2298/JSC0411901S"
}

Sladić, D., Novaković, I., Vujčić, Z., Božić, T. T., Božić, N., Milić, D., Šolaja, B.,& Gašić, M. J.. (2004). Protein covalent modification of biologically active quinones. in Journal of the Serbian Chemical Society
Serbian Chemical Society., 69(11), 901-907.
https://doi.org/10.2298/JSC0411901S

Sladić D, Novaković I, Vujčić Z, Božić TT, Božić N, Milić D, Šolaja B, Gašić MJ. Protein covalent modification of biologically active quinones. in Journal of the Serbian Chemical Society. 2004;69(11):901-907.
doi:10.2298/JSC0411901S .

Sladić, Dušan, Novaković, Irena, Vujčić, Zoran, Božić, Tatjana T., Božić, Nataša, Milić, Dragana, Šolaja, Bogdan, Gašić, Miroslav J., "Protein covalent modification of biologically active quinones" in Journal of the Serbian Chemical Society, 69, no. 11 (2004):901-907,
https://doi.org/10.2298/JSC0411901S . .

TY  - JOUR
AU  - Pajic, I
AU  - Kljajic, Z
AU  - Dogović, Nikola
AU  - Sladić, Dušan
AU  - Juranić, Zorica
AU  - Gašić, Miroslav J.
PY  - 2002
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2837
AB  - A lectin from the Adriatic sponge Haliclona cratera was purified by ion-exchange and gel chromatography The molecular mass of the lectin is approximately 29 kDa. Purified lectin is rich in hydrophobic and basic amino acids and has an isoelectric point at pH 8.6. H. cratera lectin is relatively heat- and pH-stable. It agglutinates native and trypsinized, papainized and neuraminidase-treated human A, B, O, AB and sheep erythrocytes, and the hemagglutinating activity is independent of Ca2+, Mn2+ and Mg2+ ions; D-galactose and N-acetyl-D-galactosamine are found to be moderate inhibitors of the activity. H. cratera lectin displays cytotoxic effect on HeLa and FemX cells and weak mitogenic effect on human T-lymphocytes pretreated with phytohemagglutinin (PHA). (C) 2002 Elsevier Science Inc. All rights reserved.
PB  - Elsevier Science Inc, New York
T2  - Comparative Biochemistry and Physiology. C: Toxicology and Pharmacology
T1  - A novel lectin from the sponge Haliclona cratera: isolation, characterization and biological activity
VL  - 132
IS  - 2
SP  - 213
EP  - 221
DO  - 10.1016/S1532-0456(02)00068-6
ER  - 

@article{
author = "Pajic, I and Kljajic, Z and Dogović, Nikola and Sladić, Dušan and Juranić, Zorica and Gašić, Miroslav J.",
year = "2002",
abstract = "A lectin from the Adriatic sponge Haliclona cratera was purified by ion-exchange and gel chromatography The molecular mass of the lectin is approximately 29 kDa. Purified lectin is rich in hydrophobic and basic amino acids and has an isoelectric point at pH 8.6. H. cratera lectin is relatively heat- and pH-stable. It agglutinates native and trypsinized, papainized and neuraminidase-treated human A, B, O, AB and sheep erythrocytes, and the hemagglutinating activity is independent of Ca2+, Mn2+ and Mg2+ ions; D-galactose and N-acetyl-D-galactosamine are found to be moderate inhibitors of the activity. H. cratera lectin displays cytotoxic effect on HeLa and FemX cells and weak mitogenic effect on human T-lymphocytes pretreated with phytohemagglutinin (PHA). (C) 2002 Elsevier Science Inc. All rights reserved.",
publisher = "Elsevier Science Inc, New York",
journal = "Comparative Biochemistry and Physiology. C: Toxicology and Pharmacology",
title = "A novel lectin from the sponge Haliclona cratera: isolation, characterization and biological activity",
volume = "132",
number = "2",
pages = "213-221",
doi = "10.1016/S1532-0456(02)00068-6"
}

Pajic, I., Kljajic, Z., Dogović, N., Sladić, D., Juranić, Z.,& Gašić, M. J.. (2002). A novel lectin from the sponge Haliclona cratera: isolation, characterization and biological activity. in Comparative Biochemistry and Physiology. C: Toxicology and Pharmacology
Elsevier Science Inc, New York., 132(2), 213-221.
https://doi.org/10.1016/S1532-0456(02)00068-6

Pajic I, Kljajic Z, Dogović N, Sladić D, Juranić Z, Gašić MJ. A novel lectin from the sponge Haliclona cratera: isolation, characterization and biological activity. in Comparative Biochemistry and Physiology. C: Toxicology and Pharmacology. 2002;132(2):213-221.
doi:10.1016/S1532-0456(02)00068-6 .

Pajic, I, Kljajic, Z, Dogović, Nikola, Sladić, Dušan, Juranić, Zorica, Gašić, Miroslav J., "A novel lectin from the sponge Haliclona cratera: isolation, characterization and biological activity" in Comparative Biochemistry and Physiology. C: Toxicology and Pharmacology, 132, no. 2 (2002):213-221,
https://doi.org/10.1016/S1532-0456(02)00068-6 . .

TY  - JOUR
AU  - Božić, Tatjana T.
AU  - Sladić, Dušan
AU  - Zlatović, Mario
AU  - Novaković, Irena
AU  - Trifunović, Snežana
AU  - Gašić, Miroslav J.
PY  - 2002
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/55
AB  - The regioselectivity of the reaction of conjugate addition of thiols amines, methanol and hydrogen chloride with the monoalkyl-1,4-benzoquinones avarone and 2-tert-butyl- 1,4-benzoquinone was investigated. It was shown that the regioselectivity of the reaction is influenced by the electrophilicity of position 5 in unprotonated 2-alkylquinones, the increased electrophilicity of position 6 in acidic medium, and by the acidity of the intermediate hydroquinones.
AB  - Proučavana je regioselektivnost konjugovane adicije tiola, amina, metanola i hlorovodonika na monoalkil-1,4-benzohinone avaron i 2-tert-butil-1,4-benzohinon. Pokazano je da na regioselektivnost reakcije utiču elektrofilnost položaja 5 neprotonovanih 2-alkil-hinona i povećana elektrofilnost položaja 6 u kiseloj sredini, kao i kiselost intermedijernih hidrohinona.
PB  - Serbian Chemical Society
T2  - Journal of the Serbian Chemical Society
T1  - Regioselectivity of conjugate additions to monoalkyl-1,4-benzoquinones
T1  - Regioselektivnost konjugovane adicijena monoalkil-1,4-benzohinone
VL  - 67
IS  - 8-9
SP  - 547
EP  - 551
DO  - 10.2298/JSC0209547B
ER  - 

@article{
author = "Božić, Tatjana T. and Sladić, Dušan and Zlatović, Mario and Novaković, Irena and Trifunović, Snežana and Gašić, Miroslav J.",
year = "2002",
abstract = "The regioselectivity of the reaction of conjugate addition of thiols amines, methanol and hydrogen chloride with the monoalkyl-1,4-benzoquinones avarone and 2-tert-butyl- 1,4-benzoquinone was investigated. It was shown that the regioselectivity of the reaction is influenced by the electrophilicity of position 5 in unprotonated 2-alkylquinones, the increased electrophilicity of position 6 in acidic medium, and by the acidity of the intermediate hydroquinones., Proučavana je regioselektivnost konjugovane adicije tiola, amina, metanola i hlorovodonika na monoalkil-1,4-benzohinone avaron i 2-tert-butil-1,4-benzohinon. Pokazano je da na regioselektivnost reakcije utiču elektrofilnost položaja 5 neprotonovanih 2-alkil-hinona i povećana elektrofilnost položaja 6 u kiseloj sredini, kao i kiselost intermedijernih hidrohinona.",
publisher = "Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "Regioselectivity of conjugate additions to monoalkyl-1,4-benzoquinones, Regioselektivnost konjugovane adicijena monoalkil-1,4-benzohinone",
volume = "67",
number = "8-9",
pages = "547-551",
doi = "10.2298/JSC0209547B"
}

Božić, T. T., Sladić, D., Zlatović, M., Novaković, I., Trifunović, S.,& Gašić, M. J.. (2002). Regioselectivity of conjugate additions to monoalkyl-1,4-benzoquinones. in Journal of the Serbian Chemical Society
Serbian Chemical Society., 67(8-9), 547-551.
https://doi.org/10.2298/JSC0209547B

Božić TT, Sladić D, Zlatović M, Novaković I, Trifunović S, Gašić MJ. Regioselectivity of conjugate additions to monoalkyl-1,4-benzoquinones. in Journal of the Serbian Chemical Society. 2002;67(8-9):547-551.
doi:10.2298/JSC0209547B .

Božić, Tatjana T., Sladić, Dušan, Zlatović, Mario, Novaković, Irena, Trifunović, Snežana, Gašić, Miroslav J., "Regioselectivity of conjugate additions to monoalkyl-1,4-benzoquinones" in Journal of the Serbian Chemical Society, 67, no. 8-9 (2002):547-551,
https://doi.org/10.2298/JSC0209547B . .

TY  - JOUR
AU  - Zlatović, Mario
AU  - Gašić, Miroslav J.
AU  - Sladić, Dušan
PY  - 1999
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4398
AB  - Several NADH model compounds, N-alkyl-1,4-dihydronicotinamides, some of them possessing amphiphilic properties, have been synthesized, and the kinetics of their reaction with a biologically active liphophilic quinone, avarone, has been studied in a protic solvent both in the presence and absence of cationic, anionic or non-ionic surfactants. In the absence of micellar agents, the medium-and long-chain N-dodecyl (3) and N-heptadecyl (4) derivatives show a significant increase in the reaction rates compared to other model compounds, due to the stabilization of the semiquinone intermediate. Anionic surfactants retard the reaction, non-ionic surfactants slightly accelerate the reaction with the short-chain derivatives, and retard the reaction with the medium-and long-chain derivatives, and the cationic surfactants increase the reaction rate with all derivatives except the long-chain 4. The results support the e-p-e mechanism of the reduction of lipophilic quinones by NADH models in protic medium.
AB  - Sintetisano je nekoliko N-alkil-1,4-dihidronikotinamida, model-jedinjenja
NADH, od kojih neki imaju amfifilne osobine, i proučavana je kinetika njihove
reakcije sa biološkim aktivnim, lipofilnim hinonom avaronom u protinom
rastvaraču u prisustvu katjonskih, anjonskih ili nejonskih površinski aktivnih supstanci i bez njh.Bez dodatih micelarnih agenasa, N-dodecil-derivat 3 (derivat srednje
dužine niza) i dugolančani N-heptadecil-derivat 4 pokazuju značajno povećanje brzine
reakcije u poređenju sa drugim model-jedinjenjima, usled stabilizacije semihinonskih
intermedijera. Anjonski površinski aktivni agensi usporavaju reakciju, nejonski
agensi dovode do slabog ubrzanja sa derivatima kratkog alkilniza, a usporavaju reak
ciju sa derivatima srednjeg i dugog niza, dok katjonski agensi ubrzavaju reakciju sa svim
derivatima, sem sa dugolančanim 4. Rezultati ukazuju na mehanizam e-p-e redukcije
lipofilnih hinona modelima NADH u protičnom medijumu.
PB  - Belgrade : Serbian Chemical Society
T2  - Journal of the Serbian Chemical Society
T1  - The kinetics of the reduction of the lipophilic quinone avarone by n-alkyl-1,4-dihydronicotinamides of various lipophilicities
T1  - Kinetika redukcije lipofilnog hinona avarona n-alkyl-1,4-di -hidronikotinamidima različite lipofilnosti
VL  - 64
IS  - 11
SP  - 647
EP  - 654
DO  - 10.2298/JSC9911647Z
ER  - 

@article{
author = "Zlatović, Mario and Gašić, Miroslav J. and Sladić, Dušan",
year = "1999",
abstract = "Several NADH model compounds, N-alkyl-1,4-dihydronicotinamides, some of them possessing amphiphilic properties, have been synthesized, and the kinetics of their reaction with a biologically active liphophilic quinone, avarone, has been studied in a protic solvent both in the presence and absence of cationic, anionic or non-ionic surfactants. In the absence of micellar agents, the medium-and long-chain N-dodecyl (3) and N-heptadecyl (4) derivatives show a significant increase in the reaction rates compared to other model compounds, due to the stabilization of the semiquinone intermediate. Anionic surfactants retard the reaction, non-ionic surfactants slightly accelerate the reaction with the short-chain derivatives, and retard the reaction with the medium-and long-chain derivatives, and the cationic surfactants increase the reaction rate with all derivatives except the long-chain 4. The results support the e-p-e mechanism of the reduction of lipophilic quinones by NADH models in protic medium., Sintetisano je nekoliko N-alkil-1,4-dihidronikotinamida, model-jedinjenja
NADH, od kojih neki imaju amfifilne osobine, i proučavana je kinetika njihove
reakcije sa biološkim aktivnim, lipofilnim hinonom avaronom u protinom
rastvaraču u prisustvu katjonskih, anjonskih ili nejonskih površinski aktivnih supstanci i bez njh.Bez dodatih micelarnih agenasa, N-dodecil-derivat 3 (derivat srednje
dužine niza) i dugolančani N-heptadecil-derivat 4 pokazuju značajno povećanje brzine
reakcije u poređenju sa drugim model-jedinjenjima, usled stabilizacije semihinonskih
intermedijera. Anjonski površinski aktivni agensi usporavaju reakciju, nejonski
agensi dovode do slabog ubrzanja sa derivatima kratkog alkilniza, a usporavaju reak
ciju sa derivatima srednjeg i dugog niza, dok katjonski agensi ubrzavaju reakciju sa svim
derivatima, sem sa dugolančanim 4. Rezultati ukazuju na mehanizam e-p-e redukcije
lipofilnih hinona modelima NADH u protičnom medijumu.",
publisher = "Belgrade : Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "The kinetics of the reduction of the lipophilic quinone avarone by n-alkyl-1,4-dihydronicotinamides of various lipophilicities, Kinetika redukcije lipofilnog hinona avarona n-alkyl-1,4-di -hidronikotinamidima različite lipofilnosti",
volume = "64",
number = "11",
pages = "647-654",
doi = "10.2298/JSC9911647Z"
}

Zlatović, M., Gašić, M. J.,& Sladić, D.. (1999). The kinetics of the reduction of the lipophilic quinone avarone by n-alkyl-1,4-dihydronicotinamides of various lipophilicities. in Journal of the Serbian Chemical Society
Belgrade : Serbian Chemical Society., 64(11), 647-654.
https://doi.org/10.2298/JSC9911647Z

Zlatović M, Gašić MJ, Sladić D. The kinetics of the reduction of the lipophilic quinone avarone by n-alkyl-1,4-dihydronicotinamides of various lipophilicities. in Journal of the Serbian Chemical Society. 1999;64(11):647-654.
doi:10.2298/JSC9911647Z .

Zlatović, Mario, Gašić, Miroslav J., Sladić, Dušan, "The kinetics of the reduction of the lipophilic quinone avarone by n-alkyl-1,4-dihydronicotinamides of various lipophilicities" in Journal of the Serbian Chemical Society, 64, no. 11 (1999):647-654,
https://doi.org/10.2298/JSC9911647Z . .

TY  - JOUR
AU  - Milić, Dragana
AU  - Kapor, Agneš J.
AU  - Markov, Borislava
AU  - Ribar, Bela J.
AU  - Strümpel, Marianna Katona
AU  - Juranić, Zorica
AU  - Gašić, Miroslav J.
AU  - Šolaja, Bogdan
PY  - 1999
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4405
AB  - Based on the biological properties of epoxyquinols from natural sources, the title compound was synthesised as a potential antitumor agent. Its molecular structure was partially confirmed by NMR studies. The detailed structure was established by X-ray analysis revealing two symmetry independent molecules in the asymmetric unit each consisting of four fused rings with the C(10) β-oriented hydroxy group and β-oriented O atom bridging C(4) and C(5). The conformation of A ring in both conformers A and B is boat (B3,6 ), while rings B and C are chairs (1C4) and the five-membered D ring is in an envelope (E2) conformation. The in vitro antitumor activity of title compound and its 17β-acetoxy analogue against HeLa and Fem-x cells revealed IC50 values of 5.7 and 7.1 μM, and 2.25 and 1.58 μM, respectively. Corresponding quinols were tested on 47 cell lines with 10β-hydroxy-17β-acetoxyestra-1,4-dien-3-one being most active against leukemia SR cells (GI50 = 0.17 μM).
PB  - MDPI
T2  - Molecules
T1  - X-ray crystal structure of 10β-hydroxy-4β,5β-epoxyestr-1-en3,17-dione and antitumor activity of its congeners
VL  - 4
IS  - 12
SP  - 338
EP  - 352
DO  - 10.3390/41200338
ER  - 

@article{
author = "Milić, Dragana and Kapor, Agneš J. and Markov, Borislava and Ribar, Bela J. and Strümpel, Marianna Katona and Juranić, Zorica and Gašić, Miroslav J. and Šolaja, Bogdan",
year = "1999",
abstract = "Based on the biological properties of epoxyquinols from natural sources, the title compound was synthesised as a potential antitumor agent. Its molecular structure was partially confirmed by NMR studies. The detailed structure was established by X-ray analysis revealing two symmetry independent molecules in the asymmetric unit each consisting of four fused rings with the C(10) β-oriented hydroxy group and β-oriented O atom bridging C(4) and C(5). The conformation of A ring in both conformers A and B is boat (B3,6 ), while rings B and C are chairs (1C4) and the five-membered D ring is in an envelope (E2) conformation. The in vitro antitumor activity of title compound and its 17β-acetoxy analogue against HeLa and Fem-x cells revealed IC50 values of 5.7 and 7.1 μM, and 2.25 and 1.58 μM, respectively. Corresponding quinols were tested on 47 cell lines with 10β-hydroxy-17β-acetoxyestra-1,4-dien-3-one being most active against leukemia SR cells (GI50 = 0.17 μM).",
publisher = "MDPI",
journal = "Molecules",
title = "X-ray crystal structure of 10β-hydroxy-4β,5β-epoxyestr-1-en3,17-dione and antitumor activity of its congeners",
volume = "4",
number = "12",
pages = "338-352",
doi = "10.3390/41200338"
}

Milić, D., Kapor, A. J., Markov, B., Ribar, B. J., Strümpel, M. K., Juranić, Z., Gašić, M. J.,& Šolaja, B.. (1999). X-ray crystal structure of 10β-hydroxy-4β,5β-epoxyestr-1-en3,17-dione and antitumor activity of its congeners. in Molecules
MDPI., 4(12), 338-352.
https://doi.org/10.3390/41200338

Milić D, Kapor AJ, Markov B, Ribar BJ, Strümpel MK, Juranić Z, Gašić MJ, Šolaja B. X-ray crystal structure of 10β-hydroxy-4β,5β-epoxyestr-1-en3,17-dione and antitumor activity of its congeners. in Molecules. 1999;4(12):338-352.
doi:10.3390/41200338 .

Milić, Dragana, Kapor, Agneš J., Markov, Borislava, Ribar, Bela J., Strümpel, Marianna Katona, Juranić, Zorica, Gašić, Miroslav J., Šolaja, Bogdan, "X-ray crystal structure of 10β-hydroxy-4β,5β-epoxyestr-1-en3,17-dione and antitumor activity of its congeners" in Molecules, 4, no. 12 (1999):338-352,
https://doi.org/10.3390/41200338 . .

TY  - JOUR
AU  - Lorenc, Ljubinka
AU  - Gašić, Miroslav J.
AU  - Juranić, Ivan
AU  - Dabović, Milan
AU  - Minailović, M. Lj.
PY  - 1980
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2709
AB  - Kinetic measurements of the solvolysis of (Z)-3α- and (Z)-3β-, and (E)-3α- and (E)-3β-tosyloxy-5,10-secocholest-1(10)-en-5-ones in buffered aqueous acetone (90 : 10 v/v) reveal that the (Z)-3α-, (E)-3α-, and (E)-3β-tosylates are solvolysed according to a first-order rate law (the relative rates being ca. 1 : 3 : 8), while the (Z)-3β-ester, under the same conditions, reacts at a much slower rate by a complex mechanism, the kinetics of which are best approximated by a second-order law. These data and product analysis indicate that the former three esters are solvolysed with considerable double bond participation [resulting in the case of the (E)-3-esters in intramolecular cyclopropane ring closure], and that this interaction is unimportant for the (Z)-3β-tosylate. On the basis of conformational analysis of the starting tosylates and stereoelectronic requirements for homoallylic interaction, a possible mechanistic pathway for these solvolyses is proposed.
PB  - Royal Society of Chemistry
T2  - Journal of the Chemical Society, Perkin Transactions 2
T1  - Synthesis, structure, and reactions of secosteroids containing a medium-sized ring. Part 17. Structure-reactivity relationship in the solvolysis of 5,10-secosteroidal 3-tosylates
IS  - 9
SP  - 1356
EP  - 1365
UR  - https://hdl.handle.net/21.15107/rcub_cer_2709
ER  - 

@article{
author = "Lorenc, Ljubinka and Gašić, Miroslav J. and Juranić, Ivan and Dabović, Milan and Minailović, M. Lj.",
year = "1980",
abstract = "Kinetic measurements of the solvolysis of (Z)-3α- and (Z)-3β-, and (E)-3α- and (E)-3β-tosyloxy-5,10-secocholest-1(10)-en-5-ones in buffered aqueous acetone (90 : 10 v/v) reveal that the (Z)-3α-, (E)-3α-, and (E)-3β-tosylates are solvolysed according to a first-order rate law (the relative rates being ca. 1 : 3 : 8), while the (Z)-3β-ester, under the same conditions, reacts at a much slower rate by a complex mechanism, the kinetics of which are best approximated by a second-order law. These data and product analysis indicate that the former three esters are solvolysed with considerable double bond participation [resulting in the case of the (E)-3-esters in intramolecular cyclopropane ring closure], and that this interaction is unimportant for the (Z)-3β-tosylate. On the basis of conformational analysis of the starting tosylates and stereoelectronic requirements for homoallylic interaction, a possible mechanistic pathway for these solvolyses is proposed.",
publisher = "Royal Society of Chemistry",
journal = "Journal of the Chemical Society, Perkin Transactions 2",
title = "Synthesis, structure, and reactions of secosteroids containing a medium-sized ring. Part 17. Structure-reactivity relationship in the solvolysis of 5,10-secosteroidal 3-tosylates",
number = "9",
pages = "1356-1365",
url = "https://hdl.handle.net/21.15107/rcub_cer_2709"
}

Lorenc, L., Gašić, M. J., Juranić, I., Dabović, M.,& Minailović, M. Lj.. (1980). Synthesis, structure, and reactions of secosteroids containing a medium-sized ring. Part 17. Structure-reactivity relationship in the solvolysis of 5,10-secosteroidal 3-tosylates. in Journal of the Chemical Society, Perkin Transactions 2
Royal Society of Chemistry.(9), 1356-1365.
https://hdl.handle.net/21.15107/rcub_cer_2709

Lorenc L, Gašić MJ, Juranić I, Dabović M, Minailović ML. Synthesis, structure, and reactions of secosteroids containing a medium-sized ring. Part 17. Structure-reactivity relationship in the solvolysis of 5,10-secosteroidal 3-tosylates. in Journal of the Chemical Society, Perkin Transactions 2. 1980;(9):1356-1365.
https://hdl.handle.net/21.15107/rcub_cer_2709 .

Lorenc, Ljubinka, Gašić, Miroslav J., Juranić, Ivan, Dabović, Milan, Minailović, M. Lj., "Synthesis, structure, and reactions of secosteroids containing a medium-sized ring. Part 17. Structure-reactivity relationship in the solvolysis of 5,10-secosteroidal 3-tosylates" in Journal of the Chemical Society, Perkin Transactions 2, no. 9 (1980):1356-1365,
https://hdl.handle.net/21.15107/rcub_cer_2709 .

TY  - JOUR
AU  - Lorenc, Ljubinka
AU  - Gašić, Miroslav J.
AU  - Dabović, Milan
AU  - Vuletić, N
AU  - Mihailović, Milhailo Lj.
PY  - 1979
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2700
AB  - The solvolysis of (Z)- and (E)-3β-acyloxy-5,10-seco-1(10)-cholesten-5β-ol p-nitrobenzoates 4 and 5 has been investigated and compared with the solvolytic reactivity of the epimeric (Z)- and (E)-5α-p-nitrobenzoates 1 and 2, as well as of the reference compound, i.e. the 1,10-saturated 5α-p-nitrobenzoate. Kinetic data and product analysis revealed that the relative spatial orientation of the 1(10)-olefinic double bond and the chiral center at C(5) in the 10-membered ring, which these secosteroidal 5-p-nitrobenzoates can adopt in the transition state, is the main factor which determines their solvolytic behaviour, so that the esters 1,2 and 5 solvolyse with transannular double bond participation, while such an interaction is not present in the case of the (Z)-5β-ester 4. © 1979.
PB  - Pergamon Press
T2  - Tetrahedron
T2  - Tetrahedron
T1  - Structure-reactivity relationship in the solvolysis of 5,10-secosteroidal 5-p-nitrobenzoates
VL  - 35
IS  - 20
SP  - 2445
EP  - 2452
DO  - 10.1016/S0040-4020(01)93762-7
ER  - 

@article{
author = "Lorenc, Ljubinka and Gašić, Miroslav J. and Dabović, Milan and Vuletić, N and Mihailović, Milhailo Lj.",
year = "1979",
abstract = "The solvolysis of (Z)- and (E)-3β-acyloxy-5,10-seco-1(10)-cholesten-5β-ol p-nitrobenzoates 4 and 5 has been investigated and compared with the solvolytic reactivity of the epimeric (Z)- and (E)-5α-p-nitrobenzoates 1 and 2, as well as of the reference compound, i.e. the 1,10-saturated 5α-p-nitrobenzoate. Kinetic data and product analysis revealed that the relative spatial orientation of the 1(10)-olefinic double bond and the chiral center at C(5) in the 10-membered ring, which these secosteroidal 5-p-nitrobenzoates can adopt in the transition state, is the main factor which determines their solvolytic behaviour, so that the esters 1,2 and 5 solvolyse with transannular double bond participation, while such an interaction is not present in the case of the (Z)-5β-ester 4. © 1979.",
publisher = "Pergamon Press",
journal = "Tetrahedron, Tetrahedron",
title = "Structure-reactivity relationship in the solvolysis of 5,10-secosteroidal 5-p-nitrobenzoates",
volume = "35",
number = "20",
pages = "2445-2452",
doi = "10.1016/S0040-4020(01)93762-7"
}

Lorenc, L., Gašić, M. J., Dabović, M., Vuletić, N.,& Mihailović, M. Lj.. (1979). Structure-reactivity relationship in the solvolysis of 5,10-secosteroidal 5-p-nitrobenzoates. in Tetrahedron
Pergamon Press., 35(20), 2445-2452.
https://doi.org/10.1016/S0040-4020(01)93762-7

Lorenc L, Gašić MJ, Dabović M, Vuletić N, Mihailović ML. Structure-reactivity relationship in the solvolysis of 5,10-secosteroidal 5-p-nitrobenzoates. in Tetrahedron. 1979;35(20):2445-2452.
doi:10.1016/S0040-4020(01)93762-7 .

Lorenc, Ljubinka, Gašić, Miroslav J., Dabović, Milan, Vuletić, N, Mihailović, Milhailo Lj., "Structure-reactivity relationship in the solvolysis of 5,10-secosteroidal 5-p-nitrobenzoates" in Tetrahedron, 35, no. 20 (1979):2445-2452,
https://doi.org/10.1016/S0040-4020(01)93762-7 . .

TY  - JOUR
AU  - Lorenc, Ljubinka
AU  - Gašić, Miroslav J.
AU  - Juranić, Ivan
AU  - Dabović, Milan
AU  - Mihailović, Milhailo Lj.
PY  - 1974
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2702
PB  - Pergamon Press
T2  - Tetrahedron Letters
T1  - Homoallylic interaction in steroidal cyclodecenyl systems
VL  - 15
IS  - 5
SP  - 395
EP  - 398
DO  - 10.1016/S0040-4039(01)82223-1
ER  - 

@article{
author = "Lorenc, Ljubinka and Gašić, Miroslav J. and Juranić, Ivan and Dabović, Milan and Mihailović, Milhailo Lj.",
year = "1974",
publisher = "Pergamon Press",
journal = "Tetrahedron Letters",
title = "Homoallylic interaction in steroidal cyclodecenyl systems",
volume = "15",
number = "5",
pages = "395-398",
doi = "10.1016/S0040-4039(01)82223-1"
}

Lorenc, L., Gašić, M. J., Juranić, I., Dabović, M.,& Mihailović, M. Lj.. (1974). Homoallylic interaction in steroidal cyclodecenyl systems. in Tetrahedron Letters
Pergamon Press., 15(5), 395-398.
https://doi.org/10.1016/S0040-4039(01)82223-1

Lorenc L, Gašić MJ, Juranić I, Dabović M, Mihailović ML. Homoallylic interaction in steroidal cyclodecenyl systems. in Tetrahedron Letters. 1974;15(5):395-398.
doi:10.1016/S0040-4039(01)82223-1 .

Lorenc, Ljubinka, Gašić, Miroslav J., Juranić, Ivan, Dabović, Milan, Mihailović, Milhailo Lj., "Homoallylic interaction in steroidal cyclodecenyl systems" in Tetrahedron Letters, 15, no. 5 (1974):395-398,
https://doi.org/10.1016/S0040-4039(01)82223-1 . .

TY  - JOUR
AU  - Mihailović, Milhailo Lj.
AU  - Dabović, Milan
AU  - Lorenc, Ljubinka
AU  - Gašić, Miroslav J.
PY  - 1970
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2701
PB  - Pergamon Press
T2  - Tetrahedron Letters
T1  - Transannular solvolysis reactions in seco-steroids containing a ten-membered ring.
VL  - 11
IS  - 49
SP  - 4245
EP  - 4248
DO  - 10.1016/S0040-4039(00)89455-1
ER  - 

@article{
author = "Mihailović, Milhailo Lj. and Dabović, Milan and Lorenc, Ljubinka and Gašić, Miroslav J.",
year = "1970",
publisher = "Pergamon Press",
journal = "Tetrahedron Letters",
title = "Transannular solvolysis reactions in seco-steroids containing a ten-membered ring.",
volume = "11",
number = "49",
pages = "4245-4248",
doi = "10.1016/S0040-4039(00)89455-1"
}

Mihailović, M. Lj., Dabović, M., Lorenc, L.,& Gašić, M. J.. (1970). Transannular solvolysis reactions in seco-steroids containing a ten-membered ring.. in Tetrahedron Letters
Pergamon Press., 11(49), 4245-4248.
https://doi.org/10.1016/S0040-4039(00)89455-1

Mihailović ML, Dabović M, Lorenc L, Gašić MJ. Transannular solvolysis reactions in seco-steroids containing a ten-membered ring.. in Tetrahedron Letters. 1970;11(49):4245-4248.
doi:10.1016/S0040-4039(00)89455-1 .

Mihailović, Milhailo Lj., Dabović, Milan, Lorenc, Ljubinka, Gašić, Miroslav J., "Transannular solvolysis reactions in seco-steroids containing a ten-membered ring." in Tetrahedron Letters, 11, no. 49 (1970):4245-4248,
https://doi.org/10.1016/S0040-4039(00)89455-1 . .

TY  - JOUR
AU  - Stefanović, Milutin
AU  - Djarmati, Z
AU  - Gašić, Miroslav
PY  - 1970
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4664
AB  - One of the structural features of many bitter principles ls the presence of a &-lactone ring. Some of these compounds differ from one another by the state of oxidation of the molecule as a whole and also by the state of oxidation of the lactone ring (Le. chaparrin-glauca rubol) (1). However, the correlation of these compound by direct introduction of an oxygen function Into the lactone ring by chemical means represents a great difficulty.
PB  - Elsevier
T2  - Tetrahedron Letters
T1  - Acetoxylation of steroidal lactones by means of lead tetraacetate
VL  - 11
DO  - 10.1016/S0040-4039(01)98337-6
ER  - 

@article{
author = "Stefanović, Milutin and Djarmati, Z and Gašić, Miroslav",
year = "1970",
abstract = "One of the structural features of many bitter principles ls the presence of a &-lactone ring. Some of these compounds differ from one another by the state of oxidation of the molecule as a whole and also by the state of oxidation of the lactone ring (Le. chaparrin-glauca rubol) (1). However, the correlation of these compound by direct introduction of an oxygen function Into the lactone ring by chemical means represents a great difficulty.",
publisher = "Elsevier",
journal = "Tetrahedron Letters",
title = "Acetoxylation of steroidal lactones by means of lead tetraacetate",
volume = "11",
doi = "10.1016/S0040-4039(01)98337-6"
}

Stefanović, M., Djarmati, Z.,& Gašić, M.. (1970). Acetoxylation of steroidal lactones by means of lead tetraacetate. in Tetrahedron Letters
Elsevier., 11.
https://doi.org/10.1016/S0040-4039(01)98337-6

Stefanović M, Djarmati Z, Gašić M. Acetoxylation of steroidal lactones by means of lead tetraacetate. in Tetrahedron Letters. 1970;11.
doi:10.1016/S0040-4039(01)98337-6 .

Stefanović, Milutin, Djarmati, Z, Gašić, Miroslav, "Acetoxylation of steroidal lactones by means of lead tetraacetate" in Tetrahedron Letters, 11 (1970),
https://doi.org/10.1016/S0040-4039(01)98337-6 . .

TY  - JOUR
AU  - Stefanović, Milutin
AU  - Gašić, Miroslav
AU  - Hranisavljević, J.
AU  - Đermanović, Miodrag
PY  - 1967
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4662
AB  - Although microbiological methods of introducing oxygen at C-11 of the steroid molecule are effective, it is obvious that purely synthetic way of producing cortisone and its analogs from bile acids or hecogenin have never been abandoned. Thus, we succeeded to obtain 3alpha-L-acetoxy-11,20-diketo-(5-beta)-pregnane, the key intermediate in the synthesis of 11-oxygenated corticosteroids in a very improved yield exceeding 13% calculated on starting deoxycholic acid by the following sequence of reactions.
PB  - Elsevier
T2  - Tetrahedron Letters
T1  - An improved preparation of 3-α-acetoxy-11,20-diketo-(5β)-pregnane, the key intermediate in the synthesis of 11-oxygenated corticosteroids
VL  - 8
IS  - 48
SP  - 4799
EP  - 4803
DO  - 10.1016/S0040-4039(01)89606-4
ER  - 

@article{
author = "Stefanović, Milutin and Gašić, Miroslav and Hranisavljević, J. and Đermanović, Miodrag",
year = "1967",
abstract = "Although microbiological methods of introducing oxygen at C-11 of the steroid molecule are effective, it is obvious that purely synthetic way of producing cortisone and its analogs from bile acids or hecogenin have never been abandoned. Thus, we succeeded to obtain 3alpha-L-acetoxy-11,20-diketo-(5-beta)-pregnane, the key intermediate in the synthesis of 11-oxygenated corticosteroids in a very improved yield exceeding 13% calculated on starting deoxycholic acid by the following sequence of reactions.",
publisher = "Elsevier",
journal = "Tetrahedron Letters",
title = "An improved preparation of 3-α-acetoxy-11,20-diketo-(5β)-pregnane, the key intermediate in the synthesis of 11-oxygenated corticosteroids",
volume = "8",
number = "48",
pages = "4799-4803",
doi = "10.1016/S0040-4039(01)89606-4"
}

Stefanović, M., Gašić, M., Hranisavljević, J.,& Đermanović, M.. (1967). An improved preparation of 3-α-acetoxy-11,20-diketo-(5β)-pregnane, the key intermediate in the synthesis of 11-oxygenated corticosteroids. in Tetrahedron Letters
Elsevier., 8(48), 4799-4803.
https://doi.org/10.1016/S0040-4039(01)89606-4

Stefanović M, Gašić M, Hranisavljević J, Đermanović M. An improved preparation of 3-α-acetoxy-11,20-diketo-(5β)-pregnane, the key intermediate in the synthesis of 11-oxygenated corticosteroids. in Tetrahedron Letters. 1967;8(48):4799-4803.
doi:10.1016/S0040-4039(01)89606-4 .

Stefanović, Milutin, Gašić, Miroslav, Hranisavljević, J., Đermanović, Miodrag, "An improved preparation of 3-α-acetoxy-11,20-diketo-(5β)-pregnane, the key intermediate in the synthesis of 11-oxygenated corticosteroids" in Tetrahedron Letters, 8, no. 48 (1967):4799-4803,
https://doi.org/10.1016/S0040-4039(01)89606-4 . .

TY  - JOUR
AU  - Mihailović, Milhailo Lj.
AU  - Lorenc, Ljubinka
AU  - Gašić, Miroslav J.
AU  - Rogić, Milorad
AU  - Melera, A.
AU  - Stefanović, Milutin
PY  - 1966
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4161
AB  - Assignment of configuration to the 1,10-double bond in the cis-trans isomeric 3β-acetoxy-5,10-seco-1,10-cholesten-5-ones has been achieved by means of NMR spectrometry. Some reactions of these new compounds have been studied and, as expected from conformational analysis, it was found that only the trans-isomer readily undergoes transannular cyclizations
PB  - Elsevier
T2  - Tetrahedron
T1  - Configuration and reactivity of ten-membered 5,10-seco-compounds obtained by fragmentation of 5-hydroxy-steroids
VL  - 22
IS  - 7
SP  - 2345
EP  - 2358
DO  - 10.1016/S0040-4020(01)82154-2
ER  - 

@article{
author = "Mihailović, Milhailo Lj. and Lorenc, Ljubinka and Gašić, Miroslav J. and Rogić, Milorad and Melera, A. and Stefanović, Milutin",
year = "1966",
abstract = "Assignment of configuration to the 1,10-double bond in the cis-trans isomeric 3β-acetoxy-5,10-seco-1,10-cholesten-5-ones has been achieved by means of NMR spectrometry. Some reactions of these new compounds have been studied and, as expected from conformational analysis, it was found that only the trans-isomer readily undergoes transannular cyclizations",
publisher = "Elsevier",
journal = "Tetrahedron",
title = "Configuration and reactivity of ten-membered 5,10-seco-compounds obtained by fragmentation of 5-hydroxy-steroids",
volume = "22",
number = "7",
pages = "2345-2358",
doi = "10.1016/S0040-4020(01)82154-2"
}

Mihailović, M. Lj., Lorenc, L., Gašić, M. J., Rogić, M., Melera, A.,& Stefanović, M.. (1966). Configuration and reactivity of ten-membered 5,10-seco-compounds obtained by fragmentation of 5-hydroxy-steroids. in Tetrahedron
Elsevier., 22(7), 2345-2358.
https://doi.org/10.1016/S0040-4020(01)82154-2

Mihailović ML, Lorenc L, Gašić MJ, Rogić M, Melera A, Stefanović M. Configuration and reactivity of ten-membered 5,10-seco-compounds obtained by fragmentation of 5-hydroxy-steroids. in Tetrahedron. 1966;22(7):2345-2358.
doi:10.1016/S0040-4020(01)82154-2 .

Mihailović, Milhailo Lj., Lorenc, Ljubinka, Gašić, Miroslav J., Rogić, Milorad, Melera, A., Stefanović, Milutin, "Configuration and reactivity of ten-membered 5,10-seco-compounds obtained by fragmentation of 5-hydroxy-steroids" in Tetrahedron, 22, no. 7 (1966):2345-2358,
https://doi.org/10.1016/S0040-4020(01)82154-2 . .