Synthesis of damnacanthal, a naturally occurring 9,10-anthraquinone and its analogues, and its biological evaluation against five cancer cell lines.

Damnacanthal and nordamnacanthal, two naturally occurring 9,10-anthraquinones, and their analogues were synthesized. Cytotoxic activity against five cancer cell lines was evaluated using MTT assay. 2-Bromomethyl-1,3-dimethoxyanthraquinone was found to display the highest activity against all cell li...

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Autori principali: Saha, Koushik, Lam, Kok Wai, Abas, Faridah, Hamzah, A. Sazali, Stanslas, Johnson, Lim, Siang Hui, Lajis, Nordin
Natura: Articolo
Lingua:English
English
Pubblicazione: Springer 2013
Accesso online:http://psasir.upm.edu.my/id/eprint/30470/1/Synthesis%20of%20damnacanthal.pdf
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spelling oai:psasir.upm.edu.my:30470 http://psasir.upm.edu.my/id/eprint/30470/ Synthesis of damnacanthal, a naturally occurring 9,10-anthraquinone and its analogues, and its biological evaluation against five cancer cell lines. Saha, Koushik Lam, Kok Wai Abas, Faridah Hamzah, A. Sazali Stanslas, Johnson Lim, Siang Hui Lajis, Nordin Damnacanthal and nordamnacanthal, two naturally occurring 9,10-anthraquinones, and their analogues were synthesized. Cytotoxic activity against five cancer cell lines was evaluated using MTT assay. 2-Bromomethyl-1,3-dimethoxyanthraquinone was found to display the highest activity against all cell lines with IC50 range of 2–8 μM. Structure–activity relationship (SAR) assessment was considered to rationalise the cytotoxic effect. Bromomethyl group at position C-2 of the anthraquinone was found to be important in exerting cytotoxic activity of this class of compounds. The presence of the flanking methoxyl or hydroxyl groups at C-1 and C-3 also contributes to this activity. Finally, the antioxidant effect of these compounds was evaluated. MTT assay was used to measure the cytotoxicity against different cancer cell lines. Antioxidant activity was measured by FTC and TBA methods. Only two anthraquinones, damnacanthal and nordamnacanthal, were found to be antioxidative. Springer 2013 Article PeerReviewed application/pdf en http://psasir.upm.edu.my/id/eprint/30470/1/Synthesis%20of%20damnacanthal.pdf Saha, Koushik and Lam, Kok Wai and Abas, Faridah and Hamzah, A. Sazali and Stanslas, Johnson and Lim, Siang Hui and Lajis, Nordin (2013) Synthesis of damnacanthal, a naturally occurring 9,10-anthraquinone and its analogues, and its biological evaluation against five cancer cell lines. Medicinal Chemistry Research, 22 (5). pp. 2093-2104. ISSN 1054-2523; ESSN: 1554-8120 10.1007/s00044-012-0197-5 English
institution UPM IR
collection UPM IR
language English
English
description Damnacanthal and nordamnacanthal, two naturally occurring 9,10-anthraquinones, and their analogues were synthesized. Cytotoxic activity against five cancer cell lines was evaluated using MTT assay. 2-Bromomethyl-1,3-dimethoxyanthraquinone was found to display the highest activity against all cell lines with IC50 range of 2–8 μM. Structure–activity relationship (SAR) assessment was considered to rationalise the cytotoxic effect. Bromomethyl group at position C-2 of the anthraquinone was found to be important in exerting cytotoxic activity of this class of compounds. The presence of the flanking methoxyl or hydroxyl groups at C-1 and C-3 also contributes to this activity. Finally, the antioxidant effect of these compounds was evaluated. MTT assay was used to measure the cytotoxicity against different cancer cell lines. Antioxidant activity was measured by FTC and TBA methods. Only two anthraquinones, damnacanthal and nordamnacanthal, were found to be antioxidative.
format Article
author Saha, Koushik
Lam, Kok Wai
Abas, Faridah
Hamzah, A. Sazali
Stanslas, Johnson
Lim, Siang Hui
Lajis, Nordin
spellingShingle Saha, Koushik
Lam, Kok Wai
Abas, Faridah
Hamzah, A. Sazali
Stanslas, Johnson
Lim, Siang Hui
Lajis, Nordin
Synthesis of damnacanthal, a naturally occurring 9,10-anthraquinone and its analogues, and its biological evaluation against five cancer cell lines.
author_facet Saha, Koushik
Lam, Kok Wai
Abas, Faridah
Hamzah, A. Sazali
Stanslas, Johnson
Lim, Siang Hui
Lajis, Nordin
author_sort Saha, Koushik
title Synthesis of damnacanthal, a naturally occurring 9,10-anthraquinone and its analogues, and its biological evaluation against five cancer cell lines.
title_short Synthesis of damnacanthal, a naturally occurring 9,10-anthraquinone and its analogues, and its biological evaluation against five cancer cell lines.
title_full Synthesis of damnacanthal, a naturally occurring 9,10-anthraquinone and its analogues, and its biological evaluation against five cancer cell lines.
title_fullStr Synthesis of damnacanthal, a naturally occurring 9,10-anthraquinone and its analogues, and its biological evaluation against five cancer cell lines.
title_full_unstemmed Synthesis of damnacanthal, a naturally occurring 9,10-anthraquinone and its analogues, and its biological evaluation against five cancer cell lines.
title_sort synthesis of damnacanthal, a naturally occurring 9,10-anthraquinone and its analogues, and its biological evaluation against five cancer cell lines.
publisher Springer
publishDate 2013
url http://psasir.upm.edu.my/id/eprint/30470/1/Synthesis%20of%20damnacanthal.pdf
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