Enhanced antimicrobial activity of a peptide derived from human lysozyme by arylation of its tryptophan residues

Journal of Peptide Science : an Official Publication of the European Peptide Society
Rodrigo GonzálezNancy B Iannucci

Abstract

Antimicrobial peptides are valuable agents to fight antibiotic resistance. These amphipatic species display positively charged and hydrophobic amino acids. Here, we enhance the local hydrophobicity of a model peptide derived from human lysozyme (107RKWVWWRNR115) by arylation of its tryptophan (Trp) residues, which renders a positive effect on Staphylococcus aureus and Staphylococcus epidermidis growth inhibition. This site-selective modification was accessed by solid-phase peptide synthesis using the non-proteinogenic amino acid 2-aryltryptophan, generated by direct C-H activation from protected Trp. The modification brought about a relevant increase in growth inhibition: S. aureus was fully inhibited by arylation of Trp 112 and by only 10% by arylation of Trp 109 or 111, respect to the non-arylated peptide. On the other hand, S. epidermidis was fully inhibited by the three arylated peptides and the parent peptide. The minimum inhibitory concentration was significantly reduced for S. aureus depending on the arylation site.

References

Mar 1, 1997·Journal of Applied Microbiology·A PellegriniR von Fellenberg
Dec 17, 2009·Chemistry : a European Journal·Javier Ruiz-RodríguezRodolfo Lavilla
Jun 29, 2010·Journal of Peptide Science : an Official Publication of the European Peptide Society·Rodrigo GonzálezNancy B Iannucci
Jul 20, 2013·The Journal of Organic Chemistry·Sara PreciadoRodolfo Lavilla
Aug 29, 2013·Biopolymers·N B IannucciJ M Delfino
Aug 12, 2014·Langmuir : the ACS Journal of Surfaces and Colloids·Christopher Aisenbrey, Burkhard Bechinger
Dec 2, 2014·Nature Reviews. Microbiology·Jessica M A BlairLaura J V Piddock
May 23, 2015·Nature Communications·Lorena Mendive-TapiaRodolfo Lavilla
Jun 24, 2015·ACS Medicinal Chemistry Letters·Peter G M WutsAke P Elhammer
Sep 10, 2015·Organic & Biomolecular Chemistry·Steven M WalesStephen G Pyne

❮ Previous
Next ❯

Citations

Jun 30, 2016·Journal of Peptide Science : an Official Publication of the European Peptide Society·Suhas RameshFernando Albericio
Apr 25, 2018·Journal of Medicinal Food·Wilman Carrillo, Mercedes Ramos
Aug 10, 2019·Critical Reviews in Clinical Laboratory Sciences·Adriana Barreto-SantamaríaHernando Curtidor
Apr 1, 2020·Current Topics in Medicinal Chemistry·Andrea BossoElio Pizzo
Jan 7, 2019·Journal of Molecular Biology·Marcelo D T TorresCesar de la Fuente-Nunez
Aug 11, 2017·Journal of Medicinal Chemistry·Shimaa A H Abdel MonaimBeatriz G de la Torre

❮ Previous
Next ❯

Related Concepts

Related Feeds

Antifungals

An antifungal, also known as an antimycotic medication, is a pharmaceutical fungicide or fungistatic used to treat and prevent mycosis such as athlete's foot, ringworm, candidiasis, cryptococcal meningitis, and others. Discover the latest research on antifungals here.

Bacterial Cell Wall Structure (ASM)

Bacterial cell walls are made of peptidoglycan (also called murein), which is made from polysaccharide chains cross-linked by unusual peptides containing D-amino acids. Here is the latest research on bacterial cell wall structures.

Bacterial Cell Wall Structure

Bacterial cell walls are made of peptidoglycan (also called murein), which is made from polysaccharide chains cross-linked by unusual peptides containing D-amino acids. Here is the latest research on bacterial cell wall structures.

Antifungals (ASM)

An antifungal, also known as an antimycotic medication, is a pharmaceutical fungicide or fungistatic used to treat and prevent mycosis such as athlete's foot, ringworm, candidiasis, cryptococcal meningitis, and others. Discover the latest research on antifungals here.

Related Papers

Journal of Peptide Science : an Official Publication of the European Peptide Society
Erik StrandbergAnne S Ulrich
Journal of Peptide Science : an Official Publication of the European Peptide Society
Galina M ZatsShimon Shatzmiller
Journal of Peptide Science : an Official Publication of the European Peptide Society
Sarah C MansourRobert E W Hancock
Journal of Peptide Science : an Official Publication of the European Peptide Society
Raz KhandadashGerardo Byk
© 2022 Meta ULC. All rights reserved