Efficient chemoenzymatic synthesis, cytotoxic evaluation, and SAR of epoxysterols.
A library of diastereomerically pure epoxysterols, prepared by combining chemical and enzymatic methodologies, was evaluated for cytotoxicity toward human cancer and noncancer cell lines. Unsaturated steroids were oxidized by magnesium bis(monoperoxyphthalate) hexahydrate in acetonitrile, and the resulting epimeric epoxides were enzymatically separated using Novozym 435 or lipase AY. Some of the synthesized epoxysterols have potent cytotoxicity and higher activity on cancer cell lines HT29 and LAMA-84.
Carvalho
João F S
JF
Centro de Estudos Farmaceuticos, Laboratorio Quiimica Farmaceutica, Faculdade de Farmacia, Universidade de Coimbra, 3000-548 Coimbra, Portugal.
Cruz Silva
M Manuel
MM
Moreira
João N
JN
Simões
Sérgio
S
Sá E Melo
M Luisa
ML
D000970:Antineoplastic Agents / Q000737:chemistry* / Q000494:pharmacology; D045744:Cell Line, Tumor; D020650:Combinatorial Chemistry Techniques; D004354:Drug Screening Assays, Antitumor; D004852:Epoxy Compounds / Q000737:chemistry* / Q000494:pharmacology; D006801:Humans; D013261:Sterols / Q000737:chemistry* / Q000494:pharmacology; D013329:Structure-Activity Relationship
D000970:Antineoplastic Agents; D004852:Epoxy Compounds; D013261:Sterols