Novel glycoconjugates of diospyrin, a quinonoid plant product: Synthesis and evaluation of cytotoxicity against human malignant melanoma (A375) and laryngeal carcinoma (Hep2)
Metadata of CSIR Papers
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| Title |
Novel glycoconjugates of diospyrin, a quinonoid plant product: Synthesis and evaluation of cytotoxicity against human malignant melanoma (A375) and laryngeal carcinoma (Hep2)
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| Creator |
Das Sarma, M
Ghosh, R Patra, A Chowdhury, R Chaudhuri, K Hazra, B |
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| Subject |
Chemistry, Organic
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| Description |
Glycoside derivatives of diospyrin (1) were synthesized for the first time, and the cytotoxicity of the novel compounds vis-a-vis their precursors were evaluated against two human cancer cell lines, viz. malignant melanoma (A375) and laryngeal carcinoma (Hep2). The IC50 values were in the low micromolar range for all the compounds tested, and A375 cells showed comparatively greater sensitivity than Hep2. Most of the compounds exhibited enhanced activity as compared to the plant-derived quinonoid precursor of the series (1), while the aminophenyl mannosyl (6) was found to be the most effective derivative. In A375 cells, 6 (IC50 = 0.02 mu M) showed the maximum increase in cytotoxicity (similar to 35-fold) over that of 1 (IC50 = 0.82 mu M). Again, when the glycosides were evaluated at a given concentration (0.1 mu M) for their relative capacity to generate ROS from A375 cells, the compound 6 could produce the highest amount of ROS. Incidentally, this derivative also showed a comparatively lower toxicity (IC50 similar to 41 mu M) when tested against normal human peripheral blood mononuclear cells, indicating a fair prospect of its development as a novel chemotherapeutic agent for the treatment of malignant melanoma.
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| Publisher |
ROYAL SOC CHEMISTRYCAMBRIDGETHOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLAND
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| Date |
2011-09-20T12:12:28Z
2011-09-20T12:12:28Z 2007 |
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| Type |
Article
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| Identifier |
ORGANIC & BIOMOLECULAR CHEMISTRY
1477-0520 http://hdl.handle.net/123456789/14288 |
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| Language |
English
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