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Penetratin and Derivatives Acting as Antibacterial Agents
Author(s) -
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.
Publication year - 2013
Publication title -
chemical biology and drug design
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.59
H-Index - 77
eISSN - 1747-0285
pISSN - 1747-0277
DOI - 10.1111/cbdd.12143
Subject(s) - chemistry , antibacterial activity , molecular dynamics , combinatorial chemistry , antibacterial peptide , in vitro , antimicrobial , stereochemistry , bacteria , gram , water soluble , computational chemistry , biochemistry , organic chemistry , biology , genetics
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 ‐ NH 2 and RQIKIFFQNRRM [ O ] KFKK ‐ NH 2 ) 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 /6‐31 G (d) calculations. In addition, the non‐apeptide RQIRRWWQR ‐ NH 2 showed strong inhibitory action against the Gram‐negative and Gram‐positive bacteria tested in this study.