Keyword Search:


Bookmark and Share

Total synthesis, cytotoxic effects of damnacanthal, nordamnacanthal and related anthraquinone analogues

Akhtar, Muhammad Nadeem and Zareen, Seema and Yeap, Swee Keong and Ho, Wan Yong and Lo, Kong Mun and Hasan, Aurangzeb and Mohammed Alitheen, Noorjahan Banu (2013) Total synthesis, cytotoxic effects of damnacanthal, nordamnacanthal and related anthraquinone analogues. Molecules, 18 (8). pp. 10042-10055. ISSN 1420-3049

[img] PDF
Restricted to Repository staff only

316Kb

Official URL: http://www.mdpi.com/1420-3049/18/8/10042

Abstract

Naturally occurring anthraquinones, damnacanthal (1) and nordamnacanthal (2) were synthesized with modified reaction steps and investigated for their cytotoxicity against the MCF-7 and K-562 cancer cell lines, respectively. Intermediate analogues 2-bromomethyl-1,3-dimethoxyanthraquinone (5, IC 50 = 5.70 ± 0.21 and 8.50 ± 1.18 μg/mL), 2-hydroxymethyl-1,3-dimethoxyanthraquinone (6, IC50 = 12.10 ± 0.14 and 14.00 ± 2.13), 2-formyl-1,3-dimethoxyantharquinone (7, IC 50 = 13.10 ± 1.02 and 14.80 ± 0.74), 1,3-dimethoxy-2-methylanthraquinone (4, IC50 = 9.40 ± 3.51 and 28.40 ± 2.33), and 1,3-dihydroxy-2-methylanthraquinone (3, IC 50 = 25.60 ± 0.42 and 28.40 ± 0.79) also exhibited moderate cytotoxicity against MCF-7 and K-562 cancer cell lines, respectively. Other structurally related compounds like 1,3-dihydroxyanthraquinone (13a, IC50 = 19.70 ± 0.35 and 14.50 ± 1.28), 1,3-dimethoxyanthraquinone (13b, IC50 = 6.50 ± 0.66 and 5.90 ± 0.95) were also showed good cytotoxicity. The target compound damnacanthal (1) was found to be the most cytotoxic against the MCF-7 and K-562 cancer cell lines, with IC50 values of 3.80 ± 0.57 and 5.50 ± 1.26, respectively. The structures of all compounds were elucidated with the help of detailed spectroscopic techniques.

Item Type:Article
Keyword:Anthraquinone; Cytotoxic effects; Damnacanthal; K-562; MCF-7; Nordamnacanthal
Faculty or Institute:Faculty of Biotechnology and Biomolecular Sciences
Institute of Bioscience
Publisher:MDPI
DOI Number:10.3390/molecules180810042
Altmetrics:http://www.altmetric.com/details.php?domain=psasir.upm.edu.my&doi=10.3390/molecules180810042
ID Code:28053
Deposited By: Nabilah Mustapa
Deposited On:21 Apr 2016 16:49
Last Modified:21 Apr 2016 16:49

Repository Staff Only: Edit item detail

Document Download Statistics

This item has been downloaded for since 21 Apr 2016 16:49.

View statistics for "Total synthesis, cytotoxic effects of damnacanthal, nordamnacanthal and related anthraquinone analogues"