DSpace
 

Researchspace >
General science, engineering & technology >
General science, engineering & technology >
General science, engineering & technology >

Please use this identifier to cite or link to this item: http://hdl.handle.net/10204/5958

Title: A Laccase-catalysed one-pot synthesis of aminonaphthoquinones and their anticancer activity
Authors: Wellington, KW
Kolesnikova, NI
Keywords: Biocatalysis
Laccase
Oxidative enzymes
Green chemistry
1,4-naphthohydroquinones
Primary amines
Monoamination
Anticancer agents
Cytostatic effects
Cytotoxic effects
Issue Date: May-2012
Publisher: Elsevier
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
Series/Report no.: Workflow;8813
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.
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
URI: http://www.sciencedirect.com/science/article/pii/S0968089612004026
http://hdl.handle.net/10204/5958
ISSN: 0968-0896
Appears in Collections:Sustainability science
Enzyme technologies
General science, engineering & technology
General research interest
Discovery chemistry

Files in This Item:

File Description SizeFormat
Wellington_2012.pdf339.27 kBAdobe PDFView/Open
View Statistics

Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.

 

Valid XHTML 1.0! DSpace Software Copyright © 2002-2010  Duraspace - Feedback