Penetratin and Derivatives Acting as Antibacterial Agents. (1st July 2013)

• Record Type: Journal Article
• Authors: Garro, Adriana D.; Olivella, Mónica S.; Bombasaro, José A.; Lima, Beatriz; Tapia, Alejandro; Feresin, Gabriela; Perczel, Andras; Somlai, Csaba; Penke, Botond; López Cascales, Javier; Rodríguez, Ana M.; Enriz, Ricardo D.
• Is Part Of: Chemical biology & drug design. Volume 82:Number 2(2013:Aug.)
• Page Start: 167
• Page End: 177
• Publication Date: 2013-07-01
• Subjects: Drugs -- Design -- Periodicals; Pharmaceutical chemistry -- Periodicals; Biochemistry -- Periodicals; 615.19005
• DOI: 10.1111/cbdd.12143
• Languages: English
• ISSNs: 1747-0277

Abstract

<abstract abstract-type="main" id="cbdd12143-abs-0001"> <title> <x xml:space="preserve">Abstract</x> </title> <p>The synthesis, <italic>in vitro</italic> 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.</p> </abstract>