Print Email Facebook Twitter Evaluation of readily accessible azoles as mimics of the aromatic ring of D-phenylalanine in the turn region of gramicidin S Title Evaluation of readily accessible azoles as mimics of the aromatic ring of D-phenylalanine in the turn region of gramicidin S Author van der Knaap, M. Lageveen, L.T. Busscher, H.J. Mars-Groenendijk, R. Noort, D. Otero, J.M. Llamas-Saiz, A.L. van Raaij, M.J. van der Marel, G.A. Overkleeft, H.S. Overhand, M. Publication year 2011 Abstract The influence of replacing the d-phenylalanine residue with substituted and unsubstituted azoles on the structure and biological activity of the antibiotic gramicidinS was investigated against a representative panel of Gram-positive and Gram-negative bacteria strains. Substituted triazole derivatives, obtained using a convergent synthetic strategy, are as active as gramicidinS, provided that any substituent on the triazole moiety is not too large. The unsubstituted triazole derivative was biologically less active than the parent natural product, gramicidinS. In general for the triazole series, the hemolytic activity could be correlated with the antibacterial activity, that is, the higher the antibacterial activity, the higher the toxicity towards blood cells. Interestingly, its imidazole counterpart showed high antibacterial activity, combined with significantly diminished hemolytic activity. Turning circles! A series of substituted and unsusbstituted azole derivatives of gramicidinS were synthesised, analysed and tested against a range of bacteria and against erythrocytes. The compound where R=H and X=N exhibited high antibacterial and lower hemolytic activities, while a considerable loss of antibacterial activity was observed for the triazole derivative (R=H; X=CH). © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. Subject LifeCBRN - CBRN ProtectionEELS - Earth, Environmental and Life SciencesChemistryAntibacterial activityAzoleGramicidinSHemolytic activityPeptides To reference this document use: http://resolver.tudelft.nl/uuid:7908424c-fce6-42e2-8f5c-8b06a3004447 DOI https://doi.org/10.1002/cmdc.201000539 TNO identifier 429280 ISSN 1860-7179 Source ChemMedChem, 6 (5), 840-847 Document type article Files To receive the publication files, please send an e-mail request to TNO Library.