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, IC50 = 5.70 ± 0.21 and 8.50 ± 1.18 mg/mL), 2-hydroxymethyl-1,3-dimethoxyanthraquinone (6, IC50 = 12.10 ± 0.14 and 14.00 ± 2.13), 2-formyl-1,3-dimethoxyantharquinone (7, IC50 = 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, IC50 = 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.
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Authors | Muhammad Nadeem Akhtar, Seema Zareen, Swee Keong Yeap, Wan Yong Ho, Kong Mun Lo, Aurangzeb Hasan, Noorjahan Banu Alitheen |
Journal | Molecules (Basel, Switzerland)
(Molecules)
Vol. 18
Issue 8
Pg. 10042-55
(Aug 20 2013)
ISSN: 1420-3049 [Electronic] Switzerland |
PMID | 23966087
(Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
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Chemical References |
- Aldehydes
- Anthraquinones
- nordamnacanthal
- damnacanthal
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Topics |
- Aldehydes
(chemistry, pharmacology)
- Anthraquinones
(chemistry, pharmacology)
- Cell Line, Tumor
- Cell Survival
(drug effects)
- Humans
- Inhibitory Concentration 50
- Molecular Structure
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