Antimicrobial activity of arginine- and tryptophan-rich hexapeptides: the effects of aromatic clusters, D-amino acid substitution and cyclization

The Journal of Peptide Research : Official Journal of the American Peptide Society
Axel WessolowskiMargitta Dathe

Abstract

Many antimicrobial peptides bear arginine (R)- and tryptophan (W)-rich sequence motifs. Based on the sequence Ac-RRWWRF-NH2, sets of linear and cyclic peptides were generated by changes in the amino acid sequence, L-D-amino acid exchange and naphthylalanine substituted for tryptophan. Linear RW-peptides displayed moderate activity towards Gram-positive Bacillus subtilis (15 < MIC < 31 microm) and were inactive against Gram-negative Escherichia coli at peptide concentrations < 100 microm. Cyclization induced high antimicrobial activity. The effect of cyclization was most pronounced for peptides with three adjacent aromatic residues. Incorporation of d-amino acid residues had minor influence on the biological activity. The haemolytic activity of all RW-peptides at 100 microm concentration was low (< 7% lysis for linear R/W-rich peptides and < 28% for the cyclic analogues). Introduction of naphthylalanine enhanced the biological activities of both the linear and cyclic peptides. All peptides induced permeabilization of large unilamellar vesicles (LUVs) composed of lipids of the membrane of B. subtilis and erythrocytes, but surprisingly had no effect on LUVs composed of lipids of the E. coli inner membrane. The profiles of peptide ...Continue Reading

Citations

Dec 17, 2010·The Journal of Physical Chemistry. B·Ahmad ArouriAlfred Blume
Feb 22, 2011·Applied and Environmental Microbiology·Imma GüellEmilio Montesinos
Dec 4, 2012·International Journal of Molecular Sciences·Ramamourthy GopalYoonkyung Park
Dec 5, 2012·Beilstein Journal of Organic Chemistry·H Bauke AlbadaNils Metzler-Nolte
Jul 18, 2015·Pharmaceuticals·Biljana Mojsoska, Håvard Jenssen
Nov 15, 2011·Critical Reviews in Biotechnology·Mukesh PasupuletiMartin Malmsten
Jul 19, 2012·Journal of Peptide Science : an Official Publication of the European Peptide Society·Leonardo BaldassarreIvana Cacciatore
Sep 11, 2013·Journal of Peptide Science : an Official Publication of the European Peptide Society·Jens K MunkPaul R Hansen
Jul 22, 2014·Journal of Peptide Science : an Official Publication of the European Peptide Society·Susmita BandyopadhyayChiradip Chatterjee
Jun 8, 2006·Biochimica Et Biophysica Acta·David I ChanHans J Vogel
Jan 16, 2007·Biochemical and Biophysical Research Communications·Alberto MuñozJose F Marcos
Jul 16, 2015·Reproduction in Domestic Animals = Zuchthygiene·M SchulzeM Jung
Jul 26, 2005·Biophysical Journal·Christian AppeltJ Arvid Söderhäll
Nov 26, 2008·Biochimica Et Biophysica Acta·Mateja ZorkoRoman Jerala
Aug 10, 2013·Clinical Microbiology and Infection : the Official Publication of the European Society of Clinical Microbiology and Infectious Diseases·K V K MohanC D Atreya
Nov 15, 2012·Journal of Medicinal Chemistry·Mathieu LaurencinMichèle Baudy-Floc'h
Mar 10, 2017·Scientific Reports·Kathi ScheinpflugHenrik Strahl
Mar 13, 2018·Biopolymers·Diana P SloughYu-Shan Lin
Oct 27, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Cristina CamóLidia Feliu
Aug 20, 2016·Chemical Communications : Chem Comm·Iria SalvadóM Eugenio Vázquez
Feb 20, 2018·Biometals : an International Journal on the Role of Metal Ions in Biology, Biochemistry, and Medicine·Ya HaoJianhua Wang
Aug 3, 2005·Chembiochem : a European Journal of Chemical Biology·Christian AppeltPeter Schmieder
Nov 30, 2018·Journal of Peptide Science : an Official Publication of the European Peptide Society·Thibaut TheryElke K Arendt
Aug 1, 2006·Journal of Peptide Science : an Official Publication of the European Peptide Society·Qiuhong XieSachiko Machida
May 12, 2007·Chembiochem : a European Journal of Chemical Biology·Frank BringezuAlan J Waring
Nov 7, 2007·Journal of Peptide Science : an Official Publication of the European Peptide Society·Christian AppeltPeter Schmieder
Nov 7, 2007·Journal of Peptide Science : an Official Publication of the European Peptide Society·Christof JunkesMargitta Dathe
Dec 14, 2019·Chemical Communications : Chem Comm·Valeria CastellettoEmerson Rodrigo da Silva
Apr 5, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Awdhesh Kumar MishraKwang-Hyun Baek

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