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A Laccase-catalysed one-pot synthesis of aminonaphthoquinones and their anticancer activity

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dc.contributor.author Wellington, Kevin W
dc.contributor.author Kolesnikova, NI
dc.date.accessioned 2012-06-29T10:45:41Z
dc.date.available 2012-06-29T10:45:41Z
dc.date.issued 2012-05
dc.identifier.citation Wellington, KW and Kolesnikova, NI. 2012. A Laccase-catalysed one-pot synthesis of aminonaphthoquinones and their anticancer activity. Bioorganic and Medical Chemistry, vol. 20(14), pp 4472-4481 en_US
dc.identifier.issn 0968-0896
dc.identifier.uri http://www.sciencedirect.com/science/article/pii/S0968089612004026
dc.identifier.uri http://hdl.handle.net/10204/5958
dc.description Copyright: 2012 Elsevier. This is the pre-print version of the work. The definitive version is published in Bioorganic and Medical Chemistry, vol. 20(14), pp 4472-4481 en_US
dc.description.abstract Nuclear monoamination of a 1,4-naphthohydroquinone with primary aromatic amines was catalysed by the commercial laccase, Novozym 51003, from Novozymes to afford aminonaphthoquinones. The synthesis was accomplished by reacting a mixture of the primary amine and 1,4-naphthohydroquinone in succinate-lactate buffer and a co-solvent, dimethylformamide, under mild reaction conditions in a vessel open to air at pH 4.5 and pH 6.0. Anticancer screening showed that the aminonaphthoquinones exhibited potent cytostatic effects particularly against the UACC62 (melanoma) cancer cell line (GI50 = 3.98-7.54 µM). One compound exhibited potent cytostatic effects against both the TK10 (renal) and the UACC62 (melanoma) cancer cell line. The cytostatic effects of this compound (GI50 = 8.38 µM) against the TK10 cell line was almost as good as that of the anticancer aganet, etoposide (GI50 = 7.19 µM). Two compounds exhibited potent cytostatic effects against both the UACC62 (melanoma) and the MCF7 (breast) cancer cell lines. The total growth inhibition (TGI) of most of the compounds was better than that of etoposide against the UACC62 cell line. Three compounds (TGI = 7.17-7.94 µM) exhibited potent cytostatic effects against the UACC62 cell line which was 7 to 8-fold better than that of etoposide (TGI = 52.71 µM). The aminonaphthoquinones exhibit moderate to weak cytotoxic effects against a normal HeLa cell line. The results are encouraging for further study of the aminonaphthoquinones for their application in anticancer therapy. en_US
dc.language.iso en en_US
dc.publisher Elsevier en_US
dc.relation.ispartofseries Workflow;8813
dc.subject Biocatalysis en_US
dc.subject Laccase en_US
dc.subject Oxidative enzymes en_US
dc.subject Green chemistry en_US
dc.subject 1,4-naphthohydroquinones en_US
dc.subject Primary amines en_US
dc.subject Monoamination en_US
dc.subject Anticancer agents en_US
dc.subject Cytostatic effects en_US
dc.subject Cytotoxic effects en_US
dc.title A Laccase-catalysed one-pot synthesis of aminonaphthoquinones and their anticancer activity en_US
dc.type Article en_US


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