Penetratin and Derivatives Acting as Antibacterial Agents

Garro, Adriana D. and Olivella, Mónica S. and Bombasaro, José A. and Lima, Beatriz and Tapia, Alejandro and Feresin, Gabriela and Perczel, András and Somlai, Csaba and Penke, Botond and Cascales, Javier López and Rodríguez, Ana M. and Enriz, Ricardo D. (2013) Penetratin and Derivatives Acting as Antibacterial Agents. Chemical Biology & Drug Design , 82 (2). pp. 167-177. ISSN 1747-0285


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The synthesis, in vitro evaluation and conformational study of penetratin and structurally related derivatives acting as antibacterial agents are reported. Among the compounds evaluated here, two methionine sulphoxide derivatives (RQIKIWFQNRRM[O]KWKK-NH2 and RQIKIFFQNRRM[O]KFKK-NH2) exhibited the strongest antibacterial effect in this series. In order to better understand the antimicrobial activity obtained for these peptides, we performed an exhaustive conformational analysis using different approaches. Molecular dynamics simulations were performed using two different media (water and trifluoroethanol/water). The results of these theoretical calculations were corroborated using experimental CD measurements. The electronic study for these peptides was carried out using molecular electrostatic potentials obtained from RHF/6-31G(d) calculations. In addition, the non-apeptide RQIRRWWQR-NH2 showed strong inhibitory action against the Gram-negative and Gram-positive bacteria tested in this study.

Item Type: Article
Subjects: Q Science / természettudomány > QD Chemistry / kémia > QD04 Organic chemistry / szerves kémia
Depositing User: Dóra K. Menyhárd
Date Deposited: 20 Jan 2014 14:43
Last Modified: 20 Jan 2014 14:43

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