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Three-dimensional structure of the alpha-MSH-derived candidacidal peptide [Ac-CKPV]2.

Catania A, Grieco P, Randazzo A, Novellino E, Gatti S, Rossi C, Colombo G, Lipton JM

Division of Internal Medicine, Ospedale Maggiore di Milano IRCCS, 20122 Milano, Italy. anna.catania@unimi.it

Previous research has shown that the immunomodulatory peptide alpha-melanocyte-stimulating hormone (alpha-MSH) and its carboxy-terminal tripeptide KPV (Lys-Pro-Val alpha-MSH11-13) have antimicrobial influences. By inserting a Cys-Cys linker between two units of KPV, we designed the dimer [Ac-CKPV]2 that showed excellent candidacidal effects in pilot tests and was the subject of further investigations. [Ac-CKPV]2 was active against azole-resistant Candida spp. Therefore, the molecule appeared a promising candidate for therapy of fungal infections and was the subject of a structural study. 1H-NMR and restrained mechanic and dynamic calculations suggest that the peptide adopts an extended backbone structure with a beta-turn-like structure. These results open a pathway to development of additional novel compounds that have candidacidal effects potentially useful against clinical infections.

Published 10 June 2005 in J Pept Res, 66(1): 19-26.
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