Bioorganic & Medicinal Chemistry Letters 2012-07-01

Lipase-catalyzed preparation of chromomycin A₃ analogues and biological evaluation for anticancer activity.

Javier González-Sabín, Luz Elena Núñez, Nuria Menéndez, Alfredo F Braña, Carmen Méndez, José A Salas, Vicente Gotor, Francisco Morís

Index: Bioorg. Med. Chem. Lett. 22(13) , 4310-3, (2012)

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Abstract

Several acyl derivatives of the aureolic acid chromomycin A(3) were obtained via lipase-catalyzed acylation. Lipase B from Candida antarctica (CAL-B) was found to be the only active biocatalyst, directing the acylation regioselectively towards the terminal secondary hydroxyl group of the aglycone side chain. All new chromomycin A(3) derivatives showed antitumor activity at the micromolar or lower level concentration. Particularly, chromomycin A(3) 4'-vinyladipate showed 3-5 times higher activity against the four tumor cell lines assayed as compared to chromomycin A(3).Copyright © 2012 Elsevier Ltd. All rights reserved.