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

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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Published in:Medicinal Chemistry Research
Main Author: Saha K.; Lam K.W.; Abas F.; Sazali Hamzah A.; Stanslas J.; Hui L.S.; Lajis N.H.
Format: Article
Language:English
Published: 2013
Online Access:https://www.scopus.com/inward/record.uri?eid=2-s2.0-84879684589&doi=10.1007%2fs00044-012-0197-5&partnerID=40&md5=dcf98f62fa0ec7e672cb9da28fe0d14f
id 2-s2.0-84879684589
spelling 2-s2.0-84879684589
Saha K.; Lam K.W.; Abas F.; Sazali Hamzah A.; Stanslas J.; Hui L.S.; Lajis N.H.
Synthesis of damnacanthal, a naturally occurring 9,10-anthraquinone and its analogues, and its biological evaluation against five cancer cell lines
2013
Medicinal Chemistry Research
22
5
10.1007/s00044-012-0197-5
https://www.scopus.com/inward/record.uri?eid=2-s2.0-84879684589&doi=10.1007%2fs00044-012-0197-5&partnerID=40&md5=dcf98f62fa0ec7e672cb9da28fe0d14f
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. © 2012 Springer Science+Business Media, LLC.

15548120
English
Article
author Saha K.; Lam K.W.; Abas F.; Sazali Hamzah A.; Stanslas J.; Hui L.S.; Lajis N.H.
spellingShingle Saha K.; Lam K.W.; Abas F.; Sazali Hamzah A.; Stanslas J.; Hui L.S.; Lajis N.H.
Synthesis of damnacanthal, a naturally occurring 9,10-anthraquinone and its analogues, and its biological evaluation against five cancer cell lines
author_facet Saha K.; Lam K.W.; Abas F.; Sazali Hamzah A.; Stanslas J.; Hui L.S.; Lajis N.H.
author_sort Saha K.; Lam K.W.; Abas F.; Sazali Hamzah A.; Stanslas J.; Hui L.S.; Lajis N.H.
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
publishDate 2013
container_title Medicinal Chemistry Research
container_volume 22
container_issue 5
doi_str_mv 10.1007/s00044-012-0197-5
url https://www.scopus.com/inward/record.uri?eid=2-s2.0-84879684589&doi=10.1007%2fs00044-012-0197-5&partnerID=40&md5=dcf98f62fa0ec7e672cb9da28fe0d14f
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. © 2012 Springer Science+Business Media, LLC.
publisher
issn 15548120
language English
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