A one-pot laccase-catalysed synthesis of 5,6-dihydroxylated benzo[b]furans and catechol derivatives, and their anticancer activity

Wellington, Kevin WQwebani-Ogunleye, TKolesnikova, NIBrady, DDe Koning, CB2013-10-232013-10-232013-04Wellington, K.W, Qwebani-Ogunleye, T, Kolesnikova, N.I, Brady, D and De Koning, C.B. 2013. A one-pot laccase-catalysed synthesis of 5,6-dihydroxylated benzo[b]furans and catechol derivatives, and their anticancer activity. Archive der Pharmazie Chemistry in Life Science, vol. 346, pp 266-2770365-6233http://onlinelibrary.wiley.com/doi/10.1002/ardp.201200413/pdfhttp://hdl.handle.net/10204/7015Copyright: 2013 Wiley Online Library. This is an ABSTRACT ONLY. The definitive version is published in Archive der Pharmazie Chemistry in Life Science, vol. 346, pp 266-277A commercial laccase, Suberase® from Novozymes, was used to catalyse the synthesis of 5,6-dihydroxylated benzo[b]furans and catechol derivatives. The yields were, in some cases, similar to or better than that obtained by other enzymatic, chemical or electrochemical syntheses. The synthesised derivatives were screened against renal (TK10), melanoma (UACC62), breast (MCF7) and cervical (HeLa) cancer cell-lines. GI(sub)50, TGI and LC(sub)50 are reported for the first time. Anticancer screening showed that the cytostatic effects of the 5,6-dihydroxylated benzo[b]furans were most effective against the melanoma (UACC62) cancer cell line with several compounds exhibiting potent growth inhibitory activities (GI9(sub50) = 0.77-9.76 (subµ)M) of which two compounds had better activity than the anticancer agent, etoposide (GI(sub50) = 0.89 (subµ)M). One compound exhibited potent activity (GI (sub50) = 9.73 (subµ) M) against the renal (TK10) cancer cell line and two exhibited potent activity (GI (sub50) = 8.79 and 9.30 (subµ)M) against the breast (MCF7) cancer cell line. These results encourage further studies of the 5,6-dihydroxylated benzo[b]furans for their potential application in anticancer therapy.enLaccaseBiocatalysisBenzo[b]furansC-C couplingCatechols1,3-dicarbonylsMichael additionAnticancerCytostatic effectsCytotoxic effectsA one-pot laccase-catalysed synthesis of 5,6-dihydroxylated benzo[b]furans and catechol derivatives, and their anticancer activityArticleWellington, K. W., Qwebani-Ogunleye, T., Kolesnikova, N., Brady, D., & De Koning, C. (2013). A one-pot laccase-catalysed synthesis of 5,6-dihydroxylated benzo[b]furans and catechol derivatives, and their anticancer activity. http://hdl.handle.net/10204/7015Wellington, Kevin W, T Qwebani-Ogunleye, NI Kolesnikova, D Brady, and CB De Koning "A one-pot laccase-catalysed synthesis of 5,6-dihydroxylated benzo[b]furans and catechol derivatives, and their anticancer activity." (2013) http://hdl.handle.net/10204/7015Wellington KW, Qwebani-Ogunleye T, Kolesnikova N, Brady D, De Koning C. A one-pot laccase-catalysed synthesis of 5,6-dihydroxylated benzo[b]furans and catechol derivatives, and their anticancer activity. 2013; http://hdl.handle.net/10204/7015.TY - Article AU - Wellington, Kevin W AU - Qwebani-Ogunleye, T AU - Kolesnikova, NI AU - Brady, D AU - De Koning, CB AB - A commercial laccase, Suberase® from Novozymes, was used to catalyse the synthesis of 5,6-dihydroxylated benzo[b]furans and catechol derivatives. The yields were, in some cases, similar to or better than that obtained by other enzymatic, chemical or electrochemical syntheses. The synthesised derivatives were screened against renal (TK10), melanoma (UACC62), breast (MCF7) and cervical (HeLa) cancer cell-lines. GI(sub)50, TGI and LC(sub)50 are reported for the first time. Anticancer screening showed that the cytostatic effects of the 5,6-dihydroxylated benzo[b]furans were most effective against the melanoma (UACC62) cancer cell line with several compounds exhibiting potent growth inhibitory activities (GI9(sub50) = 0.77-9.76 (subµ)M) of which two compounds had better activity than the anticancer agent, etoposide (GI(sub50) = 0.89 (subµ)M). One compound exhibited potent activity (GI (sub50) = 9.73 (subµ) M) against the renal (TK10) cancer cell line and two exhibited potent activity (GI (sub50) = 8.79 and 9.30 (subµ)M) against the breast (MCF7) cancer cell line. These results encourage further studies of the 5,6-dihydroxylated benzo[b]furans for their potential application in anticancer therapy. DA - 2013-04 DB - ResearchSpace DP - CSIR KW - Laccase KW - Biocatalysis KW - Benzo[b]furans KW - C-C coupling KW - Catechols KW - 1,3-dicarbonyls KW - Michael addition KW - Anticancer KW - Cytostatic effects KW - Cytotoxic effects LK - https://researchspace.csir.co.za PY - 2013 SM - 0365-6233 T1 - A one-pot laccase-catalysed synthesis of 5,6-dihydroxylated benzo[b]furans and catechol derivatives, and their anticancer activity TI - A one-pot laccase-catalysed synthesis of 5,6-dihydroxylated benzo[b]furans and catechol derivatives, and their anticancer activity UR - http://hdl.handle.net/10204/7015 ER -