TY  - JOUR
AU  - Opsenica, Igor
AU  - Opsenica, Dejan
AU  - Lanteri, C.A.
AU  - Anova, L.
AU  - Milhous, Wilbur K.
AU  - Smith, K. S.
AU  - Šolaja, Bogdan
PY  - 2008
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/448
AB  - The synthesis of the chimeric molecules consisting of two pharmacophores, tetraoxane and 7-chloro-4-aminoquinoline, is reported. The tetraoxanes 2, 4, and 8 show relatively potent in vitro antimalarial activities, with IC90 values for the Plasmodium falciparum strain W2 of 2.26, 12.44, and 10.74 nM, respectively. In addition, two compounds, 2 and 4, cured mice in a modified Thompson test for antimalarial blood stage activity, with a minimum curative dose of 80 mg/kg, a minimum active dose of 20 mg/kg/day, and a maximum tolerated dose of >960 mg/kg.
PB  - American Chemical Society (ACS)
T2  - Journal of Medicinal Chemistry
T1  - New chimeric antimalarials with 4-aminoquinoline moiety linked to a tetraoxane skeleton
VL  - 51
IS  - 19
SP  - 6216
EP  - 6219
DO  - 10.1021/jm8006905
ER  - 

@article{
author = "Opsenica, Igor and Opsenica, Dejan and Lanteri, C.A. and Anova, L. and Milhous, Wilbur K. and Smith, K. S. and Šolaja, Bogdan",
year = "2008",
abstract = "The synthesis of the chimeric molecules consisting of two pharmacophores, tetraoxane and 7-chloro-4-aminoquinoline, is reported. The tetraoxanes 2, 4, and 8 show relatively potent in vitro antimalarial activities, with IC90 values for the Plasmodium falciparum strain W2 of 2.26, 12.44, and 10.74 nM, respectively. In addition, two compounds, 2 and 4, cured mice in a modified Thompson test for antimalarial blood stage activity, with a minimum curative dose of 80 mg/kg, a minimum active dose of 20 mg/kg/day, and a maximum tolerated dose of >960 mg/kg.",
publisher = "American Chemical Society (ACS)",
journal = "Journal of Medicinal Chemistry",
title = "New chimeric antimalarials with 4-aminoquinoline moiety linked to a tetraoxane skeleton",
volume = "51",
number = "19",
pages = "6216-6219",
doi = "10.1021/jm8006905"
}

Opsenica, I., Opsenica, D., Lanteri, C.A., Anova, L., Milhous, W. K., Smith, K. S.,& Šolaja, B.. (2008). New chimeric antimalarials with 4-aminoquinoline moiety linked to a tetraoxane skeleton. in Journal of Medicinal Chemistry
American Chemical Society (ACS)., 51(19), 6216-6219.
https://doi.org/10.1021/jm8006905

Opsenica I, Opsenica D, Lanteri C, Anova L, Milhous WK, Smith KS, Šolaja B. New chimeric antimalarials with 4-aminoquinoline moiety linked to a tetraoxane skeleton. in Journal of Medicinal Chemistry. 2008;51(19):6216-6219.
doi:10.1021/jm8006905 .

Opsenica, Igor, Opsenica, Dejan, Lanteri, C.A., Anova, L., Milhous, Wilbur K., Smith, K. S., Šolaja, Bogdan, "New chimeric antimalarials with 4-aminoquinoline moiety linked to a tetraoxane skeleton" in Journal of Medicinal Chemistry, 51, no. 19 (2008):6216-6219,
https://doi.org/10.1021/jm8006905 . .

TY  - JOUR
AU  - Śolaja, B.A.
AU  - Opsenica, Dejan
AU  - Smith, K. S.
AU  - Milhous, Wilbur K.
AU  - Terzić, Nataša
AU  - Opsenica, Igor
AU  - Burnett, J.C.
AU  - Nuss, J.
AU  - Gussio, R.
AU  - Bavari, S.
PY  - 2008
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/451
AB  - We report on the initial result of the coupling of 4-amino-7- chloroquinoline with steroidal and adamantane constituents to provide small molecules with excellent in vitro antimalarial activities (IC90 (W2) down to 6.74 nM). The same entities also inhibit the botulinum neurotoxin serotype A light chain metalloprotease at low micromolar levels (7-31 μM). Interestingly, structural features imparting increased antimalarial activity also provide increased metalloprotease inhibition, thus allowing for simultaneous compound optimizations against distinct targets.
PB  - American Chemical Society (ACS)
T2  - Journal of Medicinal Chemistry
T1  - Novel 4-aminoquinolines active against chloroquine-resistant and sensitive P. falciparum strains that also inhibit botulinum serotype A
VL  - 51
IS  - 15
SP  - 4388
EP  - 4391
DO  - 10.1021/jm800737y
ER  - 

@article{
author = "Śolaja, B.A. and Opsenica, Dejan and Smith, K. S. and Milhous, Wilbur K. and Terzić, Nataša and Opsenica, Igor and Burnett, J.C. and Nuss, J. and Gussio, R. and Bavari, S.",
year = "2008",
abstract = "We report on the initial result of the coupling of 4-amino-7- chloroquinoline with steroidal and adamantane constituents to provide small molecules with excellent in vitro antimalarial activities (IC90 (W2) down to 6.74 nM). The same entities also inhibit the botulinum neurotoxin serotype A light chain metalloprotease at low micromolar levels (7-31 μM). Interestingly, structural features imparting increased antimalarial activity also provide increased metalloprotease inhibition, thus allowing for simultaneous compound optimizations against distinct targets.",
publisher = "American Chemical Society (ACS)",
journal = "Journal of Medicinal Chemistry",
title = "Novel 4-aminoquinolines active against chloroquine-resistant and sensitive P. falciparum strains that also inhibit botulinum serotype A",
volume = "51",
number = "15",
pages = "4388-4391",
doi = "10.1021/jm800737y"
}

Śolaja, B.A., Opsenica, D., Smith, K. S., Milhous, W. K., Terzić, N., Opsenica, I., Burnett, J.C., Nuss, J., Gussio, R.,& Bavari, S.. (2008). Novel 4-aminoquinolines active against chloroquine-resistant and sensitive P. falciparum strains that also inhibit botulinum serotype A. in Journal of Medicinal Chemistry
American Chemical Society (ACS)., 51(15), 4388-4391.
https://doi.org/10.1021/jm800737y

Śolaja B, Opsenica D, Smith KS, Milhous WK, Terzić N, Opsenica I, Burnett J, Nuss J, Gussio R, Bavari S. Novel 4-aminoquinolines active against chloroquine-resistant and sensitive P. falciparum strains that also inhibit botulinum serotype A. in Journal of Medicinal Chemistry. 2008;51(15):4388-4391.
doi:10.1021/jm800737y .

Śolaja, B.A., Opsenica, Dejan, Smith, K. S., Milhous, Wilbur K., Terzić, Nataša, Opsenica, Igor, Burnett, J.C., Nuss, J., Gussio, R., Bavari, S., "Novel 4-aminoquinolines active against chloroquine-resistant and sensitive P. falciparum strains that also inhibit botulinum serotype A" in Journal of Medicinal Chemistry, 51, no. 15 (2008):4388-4391,
https://doi.org/10.1021/jm800737y . .

TY  - JOUR
AU  - Opsenica, Igor
AU  - Opsenica, Dejan
AU  - Smith, K. S.
AU  - Milhous, Wilbur K.
AU  - Šolaja, Bogdan
PY  - 2008
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/471
AB  - Of 17 prepared 1,2,4,5-tetraoxacyclohexanes stable to reductive and acidic conditions, 3 of them were more active than artemisinin against CQ and MFQ resistant strain TM91C235 and all compounds were more active in vitro against W2 than against D6 strain. In vivo, amines 10 and 11a cured all mice at higher doses with MCD ≤ 37.5 (mg/kg)/day. Triol 13 was exceptionally active against melanoma (LOX IMVI) and ovarian cancer (IGROV1), both with LC 50 = 60 nM.
PB  - American Chemical Society (ACS)
T2  - Journal of Medicinal Chemistry
T1  - Chemical stability of the peroxide bond enables diversified synthesis of potent tetraoxane antimalarials
VL  - 51
IS  - 7
SP  - 2261
EP  - 2266
DO  - 10.1021/jm701417a
ER  - 

@article{
author = "Opsenica, Igor and Opsenica, Dejan and Smith, K. S. and Milhous, Wilbur K. and Šolaja, Bogdan",
year = "2008",
abstract = "Of 17 prepared 1,2,4,5-tetraoxacyclohexanes stable to reductive and acidic conditions, 3 of them were more active than artemisinin against CQ and MFQ resistant strain TM91C235 and all compounds were more active in vitro against W2 than against D6 strain. In vivo, amines 10 and 11a cured all mice at higher doses with MCD ≤ 37.5 (mg/kg)/day. Triol 13 was exceptionally active against melanoma (LOX IMVI) and ovarian cancer (IGROV1), both with LC 50 = 60 nM.",
publisher = "American Chemical Society (ACS)",
journal = "Journal of Medicinal Chemistry",
title = "Chemical stability of the peroxide bond enables diversified synthesis of potent tetraoxane antimalarials",
volume = "51",
number = "7",
pages = "2261-2266",
doi = "10.1021/jm701417a"
}

Opsenica, I., Opsenica, D., Smith, K. S., Milhous, W. K.,& Šolaja, B.. (2008). Chemical stability of the peroxide bond enables diversified synthesis of potent tetraoxane antimalarials. in Journal of Medicinal Chemistry
American Chemical Society (ACS)., 51(7), 2261-2266.
https://doi.org/10.1021/jm701417a

Opsenica I, Opsenica D, Smith KS, Milhous WK, Šolaja B. Chemical stability of the peroxide bond enables diversified synthesis of potent tetraoxane antimalarials. in Journal of Medicinal Chemistry. 2008;51(7):2261-2266.
doi:10.1021/jm701417a .

Opsenica, Igor, Opsenica, Dejan, Smith, K. S., Milhous, Wilbur K., Šolaja, Bogdan, "Chemical stability of the peroxide bond enables diversified synthesis of potent tetraoxane antimalarials" in Journal of Medicinal Chemistry, 51, no. 7 (2008):2261-2266,
https://doi.org/10.1021/jm701417a . .

TY  - JOUR
AU  - Opsenica, Igor
AU  - Opsenica, Dejan
AU  - Jadranin, Milka
AU  - Smith, Kirsten
AU  - Milhous, Wilbur K.
AU  - Stratakis, Manolis
AU  - Šolaja, Bogdan
PY  - 2007
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/303
AB  - Several dicyclohexylidene tetraoxanes were prepared in order to gain a further insight into structure-activity relationship of this kind of antimalarials. The tetraoxanes 2-5, obtained as a cis/trans mixture, showed pronounced antimalarial activity against Plasmodium falciparum chloroquine susceptible D6, chloroquine resistant W2 and multidrug-resistant TM91C235 (Thailand) strains. They have better than or similar activity to the corresponding desmethyl dicyclohexylidene derivatives. Two chimeric endoperoxides with superior antimalarial activity to the natural product ascaridole were also synthesized.
AB  - U ovom radu prikazana je sinteza nekoliko dicikiloheksilidenskih tetraoksana u cilju sagledavanja odnosa struktura-aktivnost ove vrste antimalarika. Jedinjenja 2-5 dobijena kao (cis,trans)-smese pokazala su izraženu antimalarijsku aktivnost prema D6, W2 i TM91C235 (Thailand) sojevima P. falciparum. Ona imaju bolju ili sličnu aktivnost od odgovarajućih desmetil cikloheksilidenskih derivata. Sintetisana su i dva endoperoksida himerne strukture znatno izraženije aktivnosti od prirodnog proizvoda askaridola. .
PB  - Serbian Chemical Society
T2  - Journal of the Serbian Chemical Society
T1  - On peroxide antimalarials
T1  - O peroksidnim antimalaricima
VL  - 72
IS  - 12
SP  - 1181
EP  - 1190
DO  - 10.2298/JSC0712181O
ER  - 

@article{
author = "Opsenica, Igor and Opsenica, Dejan and Jadranin, Milka and Smith, Kirsten and Milhous, Wilbur K. and Stratakis, Manolis and Šolaja, Bogdan",
year = "2007",
abstract = "Several dicyclohexylidene tetraoxanes were prepared in order to gain a further insight into structure-activity relationship of this kind of antimalarials. The tetraoxanes 2-5, obtained as a cis/trans mixture, showed pronounced antimalarial activity against Plasmodium falciparum chloroquine susceptible D6, chloroquine resistant W2 and multidrug-resistant TM91C235 (Thailand) strains. They have better than or similar activity to the corresponding desmethyl dicyclohexylidene derivatives. Two chimeric endoperoxides with superior antimalarial activity to the natural product ascaridole were also synthesized., U ovom radu prikazana je sinteza nekoliko dicikiloheksilidenskih tetraoksana u cilju sagledavanja odnosa struktura-aktivnost ove vrste antimalarika. Jedinjenja 2-5 dobijena kao (cis,trans)-smese pokazala su izraženu antimalarijsku aktivnost prema D6, W2 i TM91C235 (Thailand) sojevima P. falciparum. Ona imaju bolju ili sličnu aktivnost od odgovarajućih desmetil cikloheksilidenskih derivata. Sintetisana su i dva endoperoksida himerne strukture znatno izraženije aktivnosti od prirodnog proizvoda askaridola. .",
publisher = "Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "On peroxide antimalarials, O peroksidnim antimalaricima",
volume = "72",
number = "12",
pages = "1181-1190",
doi = "10.2298/JSC0712181O"
}

Opsenica, I., Opsenica, D., Jadranin, M., Smith, K., Milhous, W. K., Stratakis, M.,& Šolaja, B.. (2007). On peroxide antimalarials. in Journal of the Serbian Chemical Society
Serbian Chemical Society., 72(12), 1181-1190.
https://doi.org/10.2298/JSC0712181O

Opsenica I, Opsenica D, Jadranin M, Smith K, Milhous WK, Stratakis M, Šolaja B. On peroxide antimalarials. in Journal of the Serbian Chemical Society. 2007;72(12):1181-1190.
doi:10.2298/JSC0712181O .

Opsenica, Igor, Opsenica, Dejan, Jadranin, Milka, Smith, Kirsten, Milhous, Wilbur K., Stratakis, Manolis, Šolaja, Bogdan, "On peroxide antimalarials" in Journal of the Serbian Chemical Society, 72, no. 12 (2007):1181-1190,
https://doi.org/10.2298/JSC0712181O . .

TY  - JOUR
AU  - Terzić-Jovanović, Nataša
AU  - Opsenica, Dejan
AU  - Milić, Dragana
AU  - Tinant, Bernard
AU  - Smith, K. S.
AU  - Milhous, Wilbur K.
AU  - Šolaja, Bogdan
PY  - 2007
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/350
AB  - The synthesis of deoxycholic acid (DCA)- and cholic acid (CA)-derived mixed tetraoxanes revealed that N-(2-dimethylamino)ethyl derivatives are potent antimalarials in vitro and in vivo. The tetraoxanes presented in this paper are dual inhibitors: besides curing mice in vivo without observed toxic effects, they kill cancer cell lines at very low concentrations. For example, DCA and CA derivatives 16 and 25 cured 3/5 (160 mg/kg/day) and 2/5 (40 mg/kg/day, MTD >960 mg/kg), respectively, and they were extremely active against melanoma LOX IMVI cancer, LC50 = 22 nM and 69 nM, respectively.
PB  - American Chemical Society (ACS)
T2  - Journal of Medicinal Chemistry
T1  - Deoxycholic acid-derived tetraoxane antimalarials and antiproliferatives
VL  - 50
IS  - 21
SP  - 5118
EP  - 5127
DO  - 10.1021/jm070684m
ER  - 

@article{
author = "Terzić-Jovanović, Nataša and Opsenica, Dejan and Milić, Dragana and Tinant, Bernard and Smith, K. S. and Milhous, Wilbur K. and Šolaja, Bogdan",
year = "2007",
abstract = "The synthesis of deoxycholic acid (DCA)- and cholic acid (CA)-derived mixed tetraoxanes revealed that N-(2-dimethylamino)ethyl derivatives are potent antimalarials in vitro and in vivo. The tetraoxanes presented in this paper are dual inhibitors: besides curing mice in vivo without observed toxic effects, they kill cancer cell lines at very low concentrations. For example, DCA and CA derivatives 16 and 25 cured 3/5 (160 mg/kg/day) and 2/5 (40 mg/kg/day, MTD >960 mg/kg), respectively, and they were extremely active against melanoma LOX IMVI cancer, LC50 = 22 nM and 69 nM, respectively.",
publisher = "American Chemical Society (ACS)",
journal = "Journal of Medicinal Chemistry",
title = "Deoxycholic acid-derived tetraoxane antimalarials and antiproliferatives",
volume = "50",
number = "21",
pages = "5118-5127",
doi = "10.1021/jm070684m"
}

Terzić-Jovanović, N., Opsenica, D., Milić, D., Tinant, B., Smith, K. S., Milhous, W. K.,& Šolaja, B.. (2007). Deoxycholic acid-derived tetraoxane antimalarials and antiproliferatives. in Journal of Medicinal Chemistry
American Chemical Society (ACS)., 50(21), 5118-5127.
https://doi.org/10.1021/jm070684m

Terzić-Jovanović N, Opsenica D, Milić D, Tinant B, Smith KS, Milhous WK, Šolaja B. Deoxycholic acid-derived tetraoxane antimalarials and antiproliferatives. in Journal of Medicinal Chemistry. 2007;50(21):5118-5127.
doi:10.1021/jm070684m .

Terzić-Jovanović, Nataša, Opsenica, Dejan, Milić, Dragana, Tinant, Bernard, Smith, K. S., Milhous, Wilbur K., Šolaja, Bogdan, "Deoxycholic acid-derived tetraoxane antimalarials and antiproliferatives" in Journal of Medicinal Chemistry, 50, no. 21 (2007):5118-5127,
https://doi.org/10.1021/jm070684m . .

TY  - JOUR
AU  - Opsenica, Igor
AU  - Terzić-Jovanović, Nataša
AU  - Opsenica, Dejan
AU  - Angelovski, Goran
AU  - Lehnig, Manfred
AU  - Eilbracht, Peter
AU  - Tinant, Bernard
AU  - Juranić, Zorica
AU  - Smith, Kirsten S.
AU  - Yang, Young S.
AU  - Diaz, Damaris S.
AU  - Smith, Philip L.
AU  - Milhous, Wilbur K.
AU  - Đoković, Dejan
AU  - Šolaja, Bogdan
PY  - 2006
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3096
AB  - Mixed tetraoxanes 5a and 13 synthesized from cholic acid and 4-oxocyclohexanecarboxylic acid were as active as artemisinin against chloroquine-susceptible, chloroquine-resistant, and multidrug-resistant Plasmodium falciparum strains (IC50, IC90). Most active 13 is metabolically stable in in vitro metabolism studies. In vivo studies on tetraoxanes with a C(4'') methyl group afforded compound 15, which cured 4/5 mice at 600 and 200 mg, kg(-1), day(-1), and 2/5 mice at 50 mg, kg(-1), day(-1), showing no toxic effects. Tetraoxane 19 was an extremely active antiproliferative with LC50 of 17 nM and maximum tolerated dose of 400 mg/kg. In Fe(II)-induced scission of tetraoxane antimalarials only RO center dot radicals were detected by EPR experiments. This finding and the indication of Fe(IV)=O species led us to propose that RO center dot radicals are probably capable of inducing the parasite's death. Our results suggest that C radicals are possibly not the only lethal species derived from peroxide prodrug antimalarials, as currently believed.
PB  - American Chemical Society (ACS)
T2  - Journal of Medicinal Chemistry
T1  - Tetraoxane antimalarials and their reaction with Fe(II)
VL  - 49
IS  - 13
SP  - 3790
EP  - 3799
DO  - 10.1021/jm050966r
ER  - 

@article{
author = "Opsenica, Igor and Terzić-Jovanović, Nataša and Opsenica, Dejan and Angelovski, Goran and Lehnig, Manfred and Eilbracht, Peter and Tinant, Bernard and Juranić, Zorica and Smith, Kirsten S. and Yang, Young S. and Diaz, Damaris S. and Smith, Philip L. and Milhous, Wilbur K. and Đoković, Dejan and Šolaja, Bogdan",
year = "2006",
abstract = "Mixed tetraoxanes 5a and 13 synthesized from cholic acid and 4-oxocyclohexanecarboxylic acid were as active as artemisinin against chloroquine-susceptible, chloroquine-resistant, and multidrug-resistant Plasmodium falciparum strains (IC50, IC90). Most active 13 is metabolically stable in in vitro metabolism studies. In vivo studies on tetraoxanes with a C(4'') methyl group afforded compound 15, which cured 4/5 mice at 600 and 200 mg, kg(-1), day(-1), and 2/5 mice at 50 mg, kg(-1), day(-1), showing no toxic effects. Tetraoxane 19 was an extremely active antiproliferative with LC50 of 17 nM and maximum tolerated dose of 400 mg/kg. In Fe(II)-induced scission of tetraoxane antimalarials only RO center dot radicals were detected by EPR experiments. This finding and the indication of Fe(IV)=O species led us to propose that RO center dot radicals are probably capable of inducing the parasite's death. Our results suggest that C radicals are possibly not the only lethal species derived from peroxide prodrug antimalarials, as currently believed.",
publisher = "American Chemical Society (ACS)",
journal = "Journal of Medicinal Chemistry",
title = "Tetraoxane antimalarials and their reaction with Fe(II)",
volume = "49",
number = "13",
pages = "3790-3799",
doi = "10.1021/jm050966r"
}

Opsenica, I., Terzić-Jovanović, N., Opsenica, D., Angelovski, G., Lehnig, M., Eilbracht, P., Tinant, B., Juranić, Z., Smith, K. S., Yang, Y. S., Diaz, D. S., Smith, P. L., Milhous, W. K., Đoković, D.,& Šolaja, B.. (2006). Tetraoxane antimalarials and their reaction with Fe(II). in Journal of Medicinal Chemistry
American Chemical Society (ACS)., 49(13), 3790-3799.
https://doi.org/10.1021/jm050966r

Opsenica I, Terzić-Jovanović N, Opsenica D, Angelovski G, Lehnig M, Eilbracht P, Tinant B, Juranić Z, Smith KS, Yang YS, Diaz DS, Smith PL, Milhous WK, Đoković D, Šolaja B. Tetraoxane antimalarials and their reaction with Fe(II). in Journal of Medicinal Chemistry. 2006;49(13):3790-3799.
doi:10.1021/jm050966r .

Opsenica, Igor, Terzić-Jovanović, Nataša, Opsenica, Dejan, Angelovski, Goran, Lehnig, Manfred, Eilbracht, Peter, Tinant, Bernard, Juranić, Zorica, Smith, Kirsten S., Yang, Young S., Diaz, Damaris S., Smith, Philip L., Milhous, Wilbur K., Đoković, Dejan, Šolaja, Bogdan, "Tetraoxane antimalarials and their reaction with Fe(II)" in Journal of Medicinal Chemistry, 49, no. 13 (2006):3790-3799,
https://doi.org/10.1021/jm050966r . .

TY  - CONF
AU  - Šolaja, Bogdan
AU  - Terzić, Nataša
AU  - Smith, K. S.
AU  - Opsenica, Dejan
AU  - Smith, PL
AU  - Milhous, Wilbur K.
PY  - 2005
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2836
PB  - American Chemical Society (ACS)
C3  - Abstracts of papers of the American Chemical Society
T1  - Reductive cleavage of 1,2,4,5-tetraoxane antimalarials
VL  - 230
UR  - https://hdl.handle.net/21.15107/rcub_cherry_774
ER  - 

@conference{
author = "Šolaja, Bogdan and Terzić, Nataša and Smith, K. S. and Opsenica, Dejan and Smith, PL and Milhous, Wilbur K.",
year = "2005",
publisher = "American Chemical Society (ACS)",
journal = "Abstracts of papers of the American Chemical Society",
title = "Reductive cleavage of 1,2,4,5-tetraoxane antimalarials",
volume = "230",
url = "https://hdl.handle.net/21.15107/rcub_cherry_774"
}

Šolaja, B., Terzić, N., Smith, K. S., Opsenica, D., Smith, P.,& Milhous, W. K.. (2005). Reductive cleavage of 1,2,4,5-tetraoxane antimalarials. in Abstracts of papers of the American Chemical Society
American Chemical Society (ACS)., 230.
https://hdl.handle.net/21.15107/rcub_cherry_774

Šolaja B, Terzić N, Smith KS, Opsenica D, Smith P, Milhous WK. Reductive cleavage of 1,2,4,5-tetraoxane antimalarials. in Abstracts of papers of the American Chemical Society. 2005;230.
https://hdl.handle.net/21.15107/rcub_cherry_774 .

Šolaja, Bogdan, Terzić, Nataša, Smith, K. S., Opsenica, Dejan, Smith, PL, Milhous, Wilbur K., "Reductive cleavage of 1,2,4,5-tetraoxane antimalarials" in Abstracts of papers of the American Chemical Society, 230 (2005),
https://hdl.handle.net/21.15107/rcub_cherry_774 .

TY  - JOUR
AU  - Opsenica, Igor
AU  - Terzić-Jovanović, Nataša
AU  - Opsenica, Dejan
AU  - Milhous, Wilbur K.
AU  - Šolaja, Bogdan
PY  - 2004
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/140
AB  - Several C2 symmetrical mixed tetraoxanes were prepared starting from a gemdihydroperoxide and a ketone. The obtained tetraoxanes showed pronounced antimalarial activity against P. falciparum chloroquine resistant W2 and chloroquine susceptible D6 strains, with N-(2-dimethylamino)ethyl-7,8,15,16-tetraoxa-dispiro Š5.2.5.2Ćhexadecane-3-carboxamide being as active as artemisinin.
AB  - U ovom radu prikazana je sinteza serije C2 mešovitih tetraoksana polazeći od gem-dihidroperoksida cikloheksanona. Dobijenim derivatima ispitana je in vitro aktivnost prema W2 i D6 sojevima P. falciparum. Utvrđeno je da derivat N-(2-dimetilamino)etil 7,8,15,16-tetraoksa-dispiroŠ5.2.5.2Ćheksadekan-3-karboksamid pokazuje aktivnost vrlo blisku aktivnosti poznatog antimalarika artemizinina.
PB  - Serbian Chemical Society
T2  - Journal of the Serbian Chemical Society
T1  - 7, 8, 15, 16-Tetraoxa-dispiro [5. 2. 5. 2]hexadecane-3-carboxylic acid derivatives and their antimalarial activity
T1  - Antimalarijska aktivnost derivata 7,8,15,16-tetraoksa-dispiro5.2.5.2heksadekan-3-karboksilne kiseline
VL  - 69
IS  - 11
SP  - 919
EP  - 922
DO  - 10.2298/JSC0411919O
ER  - 

@article{
author = "Opsenica, Igor and Terzić-Jovanović, Nataša and Opsenica, Dejan and Milhous, Wilbur K. and Šolaja, Bogdan",
year = "2004",
abstract = "Several C2 symmetrical mixed tetraoxanes were prepared starting from a gemdihydroperoxide and a ketone. The obtained tetraoxanes showed pronounced antimalarial activity against P. falciparum chloroquine resistant W2 and chloroquine susceptible D6 strains, with N-(2-dimethylamino)ethyl-7,8,15,16-tetraoxa-dispiro Š5.2.5.2Ćhexadecane-3-carboxamide being as active as artemisinin., U ovom radu prikazana je sinteza serije C2 mešovitih tetraoksana polazeći od gem-dihidroperoksida cikloheksanona. Dobijenim derivatima ispitana je in vitro aktivnost prema W2 i D6 sojevima P. falciparum. Utvrđeno je da derivat N-(2-dimetilamino)etil 7,8,15,16-tetraoksa-dispiroŠ5.2.5.2Ćheksadekan-3-karboksamid pokazuje aktivnost vrlo blisku aktivnosti poznatog antimalarika artemizinina.",
publisher = "Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "7, 8, 15, 16-Tetraoxa-dispiro [5. 2. 5. 2]hexadecane-3-carboxylic acid derivatives and their antimalarial activity, Antimalarijska aktivnost derivata 7,8,15,16-tetraoksa-dispiro5.2.5.2heksadekan-3-karboksilne kiseline",
volume = "69",
number = "11",
pages = "919-922",
doi = "10.2298/JSC0411919O"
}

Opsenica, I., Terzić-Jovanović, N., Opsenica, D., Milhous, W. K.,& Šolaja, B.. (2004). 7, 8, 15, 16-Tetraoxa-dispiro [5. 2. 5. 2]hexadecane-3-carboxylic acid derivatives and their antimalarial activity. in Journal of the Serbian Chemical Society
Serbian Chemical Society., 69(11), 919-922.
https://doi.org/10.2298/JSC0411919O

Opsenica I, Terzić-Jovanović N, Opsenica D, Milhous WK, Šolaja B. 7, 8, 15, 16-Tetraoxa-dispiro [5. 2. 5. 2]hexadecane-3-carboxylic acid derivatives and their antimalarial activity. in Journal of the Serbian Chemical Society. 2004;69(11):919-922.
doi:10.2298/JSC0411919O .

Opsenica, Igor, Terzić-Jovanović, Nataša, Opsenica, Dejan, Milhous, Wilbur K., Šolaja, Bogdan, "7, 8, 15, 16-Tetraoxa-dispiro [5. 2. 5. 2]hexadecane-3-carboxylic acid derivatives and their antimalarial activity" in Journal of the Serbian Chemical Society, 69, no. 11 (2004):919-922,
https://doi.org/10.2298/JSC0411919O . .

TY  - JOUR
AU  - Opsenica, Dejan
AU  - Angelovski, Goran
AU  - Pocsfalvi, Gabriella
AU  - Juranić, Zorica
AU  - Žižak, Željko
AU  - Kyle, Dennis
AU  - Milhous, Wilbur K.
AU  - Šolaja, Bogdan
PY  - 2003
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/7446
AB  - Several cis and trans bis-steroidal 1,2,4,5-tetraoxanes possessing amide terminus were synthesised and evaluated as antimalarials and antiproliferatives. The compounds exhibited submicromolar antimalarial activity against Plasmodium falciparum D6 and W2 strains. The existence of HN-C(O) moiety was found necessary for pronounced antimalarial and antiproliferative activity. In antiproliferative screen, the trans tetraoxane 6 was found to exhibit a pronounced cytotoxicity on 14 cancer cell lines. In addition, tetraoxanes 11 and 12 exhibited significant cytotoxic activity too; microscopic examination of treated HeLa cells showed morphological appearance reminiscent for apoptosis (condensed and/or fragmented nuclei).
PB  - Elsevier
T2  - Bioorganic and Medicinal Chemistry
T1  - Antimalarial and antiproliferative evaluation of bis-steroidal tetraoxanes
VL  - 11
IS  - 13
SP  - 2761
EP  - 2768
DO  - 10.1016/S0968-0896(03)00224-4
ER  - 

@article{
author = "Opsenica, Dejan and Angelovski, Goran and Pocsfalvi, Gabriella and Juranić, Zorica and Žižak, Željko and Kyle, Dennis and Milhous, Wilbur K. and Šolaja, Bogdan",
year = "2003",
abstract = "Several cis and trans bis-steroidal 1,2,4,5-tetraoxanes possessing amide terminus were synthesised and evaluated as antimalarials and antiproliferatives. The compounds exhibited submicromolar antimalarial activity against Plasmodium falciparum D6 and W2 strains. The existence of HN-C(O) moiety was found necessary for pronounced antimalarial and antiproliferative activity. In antiproliferative screen, the trans tetraoxane 6 was found to exhibit a pronounced cytotoxicity on 14 cancer cell lines. In addition, tetraoxanes 11 and 12 exhibited significant cytotoxic activity too; microscopic examination of treated HeLa cells showed morphological appearance reminiscent for apoptosis (condensed and/or fragmented nuclei).",
publisher = "Elsevier",
journal = "Bioorganic and Medicinal Chemistry",
title = "Antimalarial and antiproliferative evaluation of bis-steroidal tetraoxanes",
volume = "11",
number = "13",
pages = "2761-2768",
doi = "10.1016/S0968-0896(03)00224-4"
}

Opsenica, D., Angelovski, G., Pocsfalvi, G., Juranić, Z., Žižak, Ž., Kyle, D., Milhous, W. K.,& Šolaja, B.. (2003). Antimalarial and antiproliferative evaluation of bis-steroidal tetraoxanes. in Bioorganic and Medicinal Chemistry
Elsevier., 11(13), 2761-2768.
https://doi.org/10.1016/S0968-0896(03)00224-4

Opsenica D, Angelovski G, Pocsfalvi G, Juranić Z, Žižak Ž, Kyle D, Milhous WK, Šolaja B. Antimalarial and antiproliferative evaluation of bis-steroidal tetraoxanes. in Bioorganic and Medicinal Chemistry. 2003;11(13):2761-2768.
doi:10.1016/S0968-0896(03)00224-4 .

Opsenica, Dejan, Angelovski, Goran, Pocsfalvi, Gabriella, Juranić, Zorica, Žižak, Željko, Kyle, Dennis, Milhous, Wilbur K., Šolaja, Bogdan, "Antimalarial and antiproliferative evaluation of bis-steroidal tetraoxanes" in Bioorganic and Medicinal Chemistry, 11, no. 13 (2003):2761-2768,
https://doi.org/10.1016/S0968-0896(03)00224-4 . .

TY  - JOUR
AU  - Opsenica, Dejan
AU  - Dennis, Kyle E.
AU  - Milhous, Wilbur K.
AU  - Šolaja, Bogdan
PY  - 2003
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/116
AB  - Mixed tetraoxanes of the 4"-phenyl-substituted cyclohexyl-spirotetraoxacyclohexyl- spirocholate series have been prepared and evaluated as possible antimalarials, antiproliferatives and antimycobacterials. The activity of the (4"R or S)-phenyl series against P. falciparum D6 and W2 strains was found to be at the level of artemisinin with two compounds, the acid 4 and the amide 6, exhibiting encouraging anti-TB activity as well. Very promising in vitro results of the said tetraoxanes were obtained against solid tumours and, in some instances, the activity against a selected number of cell lines was higher than that of the antitumor drug Paclitaxel.
AB  - U ovom radu prikazana je sinteza serije mešovitih tetraoksana 4"-fenil-supstituisanih cikloheksil-spirotetraoksacikloheksil-spiroholata, a ispitana je i njihova in vitro aktivnost kao mogućih antimalarika, anti-TBC agenasa i antiproliferativnih jedinjenja. Aktivnost (4"R ili S)-fenil serije na D6 i W2 sojeve P. falciparum vrlo je slična aktivnosti poznatog antimalarika artemizinina. Izraženu anti-TBC aktivnost iskazala su jedinjenja 4 i 6, čija antiproliferativna in vitro aktivnost prema nekim kompaktnim tumorima prevazilazi aktivnost leka paklitaksela.
PB  - Serbian Chemical Society
T2  - Journal of the Serbian Chemical Society
T1  - Antimalarial, antimycobacterial and antiproliferative activity of phenyl substituted mixed tetraoxanes
T1  - Antimalarijska, antimikobakterijska i antiproliferativna aktivnost fenil-supstituisanih tetraoksana
VL  - 68
IS  - 4-5
SP  - 291
EP  - 302
DO  - 10.2298/JSC0305291O
ER  - 

@article{
author = "Opsenica, Dejan and Dennis, Kyle E. and Milhous, Wilbur K. and Šolaja, Bogdan",
year = "2003",
abstract = "Mixed tetraoxanes of the 4"-phenyl-substituted cyclohexyl-spirotetraoxacyclohexyl- spirocholate series have been prepared and evaluated as possible antimalarials, antiproliferatives and antimycobacterials. The activity of the (4"R or S)-phenyl series against P. falciparum D6 and W2 strains was found to be at the level of artemisinin with two compounds, the acid 4 and the amide 6, exhibiting encouraging anti-TB activity as well. Very promising in vitro results of the said tetraoxanes were obtained against solid tumours and, in some instances, the activity against a selected number of cell lines was higher than that of the antitumor drug Paclitaxel., U ovom radu prikazana je sinteza serije mešovitih tetraoksana 4"-fenil-supstituisanih cikloheksil-spirotetraoksacikloheksil-spiroholata, a ispitana je i njihova in vitro aktivnost kao mogućih antimalarika, anti-TBC agenasa i antiproliferativnih jedinjenja. Aktivnost (4"R ili S)-fenil serije na D6 i W2 sojeve P. falciparum vrlo je slična aktivnosti poznatog antimalarika artemizinina. Izraženu anti-TBC aktivnost iskazala su jedinjenja 4 i 6, čija antiproliferativna in vitro aktivnost prema nekim kompaktnim tumorima prevazilazi aktivnost leka paklitaksela.",
publisher = "Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "Antimalarial, antimycobacterial and antiproliferative activity of phenyl substituted mixed tetraoxanes, Antimalarijska, antimikobakterijska i antiproliferativna aktivnost fenil-supstituisanih tetraoksana",
volume = "68",
number = "4-5",
pages = "291-302",
doi = "10.2298/JSC0305291O"
}

Opsenica, D., Dennis, K. E., Milhous, W. K.,& Šolaja, B.. (2003). Antimalarial, antimycobacterial and antiproliferative activity of phenyl substituted mixed tetraoxanes. in Journal of the Serbian Chemical Society
Serbian Chemical Society., 68(4-5), 291-302.
https://doi.org/10.2298/JSC0305291O

Opsenica D, Dennis KE, Milhous WK, Šolaja B. Antimalarial, antimycobacterial and antiproliferative activity of phenyl substituted mixed tetraoxanes. in Journal of the Serbian Chemical Society. 2003;68(4-5):291-302.
doi:10.2298/JSC0305291O .

Opsenica, Dejan, Dennis, Kyle E., Milhous, Wilbur K., Šolaja, Bogdan, "Antimalarial, antimycobacterial and antiproliferative activity of phenyl substituted mixed tetraoxanes" in Journal of the Serbian Chemical Society, 68, no. 4-5 (2003):291-302,
https://doi.org/10.2298/JSC0305291O . .

TY  - JOUR
AU  - Opsenica, Dejan
AU  - Pocsfalvi, Gabriella
AU  - Milhous, Wilbur K.
AU  - Šolaja, Bogdan
PY  - 2002
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/53
AB  - An intramolecular steroidal 1,2,4,5-tetraoxane has been synthesised in six steps starting from methyl3-oxo-7α,12α-diacetoxy-5β-cholan-24-oate. The synthesised 1,2,4,5-tetraoxane has moderate in vitro antimalarial activity against P. falciparum strains (IC50 (D6) = 0.35 µg/mL; IC50 (W2) = 0.29 µg/mL).
AB  - Polazeći od methyl 3-oxo-7α,12α-diacetoxy-5β-cholan-24-oate sintetisan je u šest faza intramolekulski steroidni 1,2,4,5-tetraoksan. Proizvod ima umerenu in vitro antimalarijsku aktivnost prema P. falciparum sojevima (IC50 (D6) = 0.35 µg/mL; IC50 (W2) = 0.29 µg/mL).
PB  - Serbian Chemical Society
T2  - Journal of the Serbian Chemical Society
T1  - Antimalarial peroxides: The first intramolecular 1,2,4,5-tetraoxane
T1  - Antimalarijski peroksidi - prvi intramolekulski 1,2,4,5-tetraoksan
VL  - 67
IS  - 7
SP  - 465
EP  - 471
DO  - 10.2298/JSC0207465O
ER  - 

@article{
author = "Opsenica, Dejan and Pocsfalvi, Gabriella and Milhous, Wilbur K. and Šolaja, Bogdan",
year = "2002",
abstract = "An intramolecular steroidal 1,2,4,5-tetraoxane has been synthesised in six steps starting from methyl3-oxo-7α,12α-diacetoxy-5β-cholan-24-oate. The synthesised 1,2,4,5-tetraoxane has moderate in vitro antimalarial activity against P. falciparum strains (IC50 (D6) = 0.35 µg/mL; IC50 (W2) = 0.29 µg/mL)., Polazeći od methyl 3-oxo-7α,12α-diacetoxy-5β-cholan-24-oate sintetisan je u šest faza intramolekulski steroidni 1,2,4,5-tetraoksan. Proizvod ima umerenu in vitro antimalarijsku aktivnost prema P. falciparum sojevima (IC50 (D6) = 0.35 µg/mL; IC50 (W2) = 0.29 µg/mL).",
publisher = "Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "Antimalarial peroxides: The first intramolecular 1,2,4,5-tetraoxane, Antimalarijski peroksidi - prvi intramolekulski 1,2,4,5-tetraoksan",
volume = "67",
number = "7",
pages = "465-471",
doi = "10.2298/JSC0207465O"
}

Opsenica, D., Pocsfalvi, G., Milhous, W. K.,& Šolaja, B.. (2002). Antimalarial peroxides: The first intramolecular 1,2,4,5-tetraoxane. in Journal of the Serbian Chemical Society
Serbian Chemical Society., 67(7), 465-471.
https://doi.org/10.2298/JSC0207465O

Opsenica D, Pocsfalvi G, Milhous WK, Šolaja B. Antimalarial peroxides: The first intramolecular 1,2,4,5-tetraoxane. in Journal of the Serbian Chemical Society. 2002;67(7):465-471.
doi:10.2298/JSC0207465O .

Opsenica, Dejan, Pocsfalvi, Gabriella, Milhous, Wilbur K., Šolaja, Bogdan, "Antimalarial peroxides: The first intramolecular 1,2,4,5-tetraoxane" in Journal of the Serbian Chemical Society, 67, no. 7 (2002):465-471,
https://doi.org/10.2298/JSC0207465O . .

TY  - JOUR
AU  - Šolaja, Bogdan
AU  - Terzić, Nataša
AU  - Pocsfalvi, Gabriella
AU  - Gerena, L.
AU  - Tinant, Bernard
AU  - Opsenica, Dejan
AU  - Milhous, Wilbur K.
PY  - 2002
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/91
AB  - Mixed 1,2,4,5-tetraoxanes possessing simple spirocycloalkane and spirocholic acid-derived substituents were prepared and shown to have significantly higher in vitro antimalarial activity than bis-substituted tetraoxanes. Out of 41 synthesized tetraoxanes, 12 were in vitro more potent against Plasmodium falciparum chloroquine-resistant W2 clone than artemisinin, and the most potent one was 2.4 times as active as arteether. In addition, 9 compounds exhibit higher activity than chloroquine against P. falciparum chloroquine-susceptible D6 clone. Cytotoxicity was assessed for most active compounds against the Vero cell line, showing a cytotoxicity/antimalarial potency ratio of 1/(1400-9500). For the first time, tetraoxanes were screened against Mycobacterium tuberculosis with MICs as low as 4.73 μM against H37Rv strain. Mixed tetraoxanes were synthesized in a simple procedure from cholic acid methyl esters by direct coupling of steroidal gem-dihydroperoxide to simple ketones and further transformed into corresponding acids and amides.
PB  - American Chemical Society (ACS)
T2  - Journal of Medicinal Chemistry
T1  - Mixed steroidal 1,2,4,5-tetraoxanes: Antimalarial and antimycobacterial activity
VL  - 45
IS  - 16
SP  - 3331
EP  - 3336
DO  - 10.1021/jm020891g
ER  - 

@article{
author = "Šolaja, Bogdan and Terzić, Nataša and Pocsfalvi, Gabriella and Gerena, L. and Tinant, Bernard and Opsenica, Dejan and Milhous, Wilbur K.",
year = "2002",
abstract = "Mixed 1,2,4,5-tetraoxanes possessing simple spirocycloalkane and spirocholic acid-derived substituents were prepared and shown to have significantly higher in vitro antimalarial activity than bis-substituted tetraoxanes. Out of 41 synthesized tetraoxanes, 12 were in vitro more potent against Plasmodium falciparum chloroquine-resistant W2 clone than artemisinin, and the most potent one was 2.4 times as active as arteether. In addition, 9 compounds exhibit higher activity than chloroquine against P. falciparum chloroquine-susceptible D6 clone. Cytotoxicity was assessed for most active compounds against the Vero cell line, showing a cytotoxicity/antimalarial potency ratio of 1/(1400-9500). For the first time, tetraoxanes were screened against Mycobacterium tuberculosis with MICs as low as 4.73 μM against H37Rv strain. Mixed tetraoxanes were synthesized in a simple procedure from cholic acid methyl esters by direct coupling of steroidal gem-dihydroperoxide to simple ketones and further transformed into corresponding acids and amides.",
publisher = "American Chemical Society (ACS)",
journal = "Journal of Medicinal Chemistry",
title = "Mixed steroidal 1,2,4,5-tetraoxanes: Antimalarial and antimycobacterial activity",
volume = "45",
number = "16",
pages = "3331-3336",
doi = "10.1021/jm020891g"
}

Šolaja, B., Terzić, N., Pocsfalvi, G., Gerena, L., Tinant, B., Opsenica, D.,& Milhous, W. K.. (2002). Mixed steroidal 1,2,4,5-tetraoxanes: Antimalarial and antimycobacterial activity. in Journal of Medicinal Chemistry
American Chemical Society (ACS)., 45(16), 3331-3336.
https://doi.org/10.1021/jm020891g

Šolaja B, Terzić N, Pocsfalvi G, Gerena L, Tinant B, Opsenica D, Milhous WK. Mixed steroidal 1,2,4,5-tetraoxanes: Antimalarial and antimycobacterial activity. in Journal of Medicinal Chemistry. 2002;45(16):3331-3336.
doi:10.1021/jm020891g .

Šolaja, Bogdan, Terzić, Nataša, Pocsfalvi, Gabriella, Gerena, L., Tinant, Bernard, Opsenica, Dejan, Milhous, Wilbur K., "Mixed steroidal 1,2,4,5-tetraoxanes: Antimalarial and antimycobacterial activity" in Journal of Medicinal Chemistry, 45, no. 16 (2002):3331-3336,
https://doi.org/10.1021/jm020891g . .

TY  - JOUR
AU  - Opsenica, Dejan
AU  - Pocsfalvi, Gabriella
AU  - Juranić, Zorica
AU  - Tinant, Bernard
AU  - Declercq, J.-P.
AU  - Kyle, D.E.
AU  - Milhous, Wilbur K.
AU  - Šolaja, Bogdan
PY  - 2000
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/21
AB  - Cholic acid-derived 1,2,4,5-tetraoxanes were synthesized in order to explore the influence of steroid carrier on its antimalarial and antiproliferative activity in vitro. Starting with chiral ketones, cis and trans series of diastereomeric tetraoxanes were obtained, and the cis series was found to be ~2 times as active as the trans against Plasmodium falciparum D6 and W2 clones. The same tendency was observed against human melanoma (Fem-X) and human cervix carcinoma (HeLa) cell lines. The amide C(24) termini, for the first time introduced into the carrier molecule of a tetraoxane pharmacophore, significantly enhanced both antimalarial and antiproliferative activity, as compared to the corresponding methyl esters, with cis-bis(N-propylamide) being most efficient against the chloroquine-susceptible D6 clone (IC50 = 9.29 nM). cis- and trans-bis(N-propylamides) were also screened against PBMC, and PHA-stimulated PBMC, showing a cytotoxicity/antimalarial potency ratio of 1/10 000.
PB  - American Chemical Society (ACS)
T2  - Journal of Medicinal Chemistry
T1  - Cholic acid derivatives as 1,2,4,5-tetraoxane carriers: Structure and antimalarial and antiproliferative activity
VL  - 43
IS  - 17
SP  - 3274
EP  - 3282
DO  - 10.1021/jm000952f
ER  - 

@article{
author = "Opsenica, Dejan and Pocsfalvi, Gabriella and Juranić, Zorica and Tinant, Bernard and Declercq, J.-P. and Kyle, D.E. and Milhous, Wilbur K. and Šolaja, Bogdan",
year = "2000",
abstract = "Cholic acid-derived 1,2,4,5-tetraoxanes were synthesized in order to explore the influence of steroid carrier on its antimalarial and antiproliferative activity in vitro. Starting with chiral ketones, cis and trans series of diastereomeric tetraoxanes were obtained, and the cis series was found to be ~2 times as active as the trans against Plasmodium falciparum D6 and W2 clones. The same tendency was observed against human melanoma (Fem-X) and human cervix carcinoma (HeLa) cell lines. The amide C(24) termini, for the first time introduced into the carrier molecule of a tetraoxane pharmacophore, significantly enhanced both antimalarial and antiproliferative activity, as compared to the corresponding methyl esters, with cis-bis(N-propylamide) being most efficient against the chloroquine-susceptible D6 clone (IC50 = 9.29 nM). cis- and trans-bis(N-propylamides) were also screened against PBMC, and PHA-stimulated PBMC, showing a cytotoxicity/antimalarial potency ratio of 1/10 000.",
publisher = "American Chemical Society (ACS)",
journal = "Journal of Medicinal Chemistry",
title = "Cholic acid derivatives as 1,2,4,5-tetraoxane carriers: Structure and antimalarial and antiproliferative activity",
volume = "43",
number = "17",
pages = "3274-3282",
doi = "10.1021/jm000952f"
}

Opsenica, D., Pocsfalvi, G., Juranić, Z., Tinant, B., Declercq, J.-P., Kyle, D.E., Milhous, W. K.,& Šolaja, B.. (2000). Cholic acid derivatives as 1,2,4,5-tetraoxane carriers: Structure and antimalarial and antiproliferative activity. in Journal of Medicinal Chemistry
American Chemical Society (ACS)., 43(17), 3274-3282.
https://doi.org/10.1021/jm000952f

Opsenica D, Pocsfalvi G, Juranić Z, Tinant B, Declercq J, Kyle D, Milhous WK, Šolaja B. Cholic acid derivatives as 1,2,4,5-tetraoxane carriers: Structure and antimalarial and antiproliferative activity. in Journal of Medicinal Chemistry. 2000;43(17):3274-3282.
doi:10.1021/jm000952f .

Opsenica, Dejan, Pocsfalvi, Gabriella, Juranić, Zorica, Tinant, Bernard, Declercq, J.-P., Kyle, D.E., Milhous, Wilbur K., Šolaja, Bogdan, "Cholic acid derivatives as 1,2,4,5-tetraoxane carriers: Structure and antimalarial and antiproliferative activity" in Journal of Medicinal Chemistry, 43, no. 17 (2000):3274-3282,
https://doi.org/10.1021/jm000952f . .