Synthesis and biological activity of derivatives of the marine quinone avarone
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2010
Authors
Božić, Tatjana T.
Novaković, Irena

Gašić, Miroslav J.
Juranić, Zorica

Stanojković, Tatjana

Tufegdžić, Srđan

Kljajić, Zoran
Sladić, Dušan

Article (Published version)

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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.
Keywords:
Marine quinone / Avarone / Alkyl(aryl)thio derivatives / cytotoxic activity / Cyclic voltammetrySource:
European Journal of Medicinal Chemistry, 2010, 45, 3, 923-929Publisher:
- Elsevier France-Editions Scientifiques Medicales Elsevier, Paris
Funding / projects:
- Interakcije prirodnih proizvoda i njihovih analoga sa proteinima i nukleinskim kiselinama (RS-142026)
DOI: 10.1016/j.ejmech.2009.11.033
ISSN: 0223-5234
PubMed: 19995673
WoS: 000275404900010
Scopus: 2-s2.0-75949110978
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IHTMTY - 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 . .