Issue 88, 2016, Issue in Progress

π-Stacking assisted redox active peptide–gallol conjugate: synthesis of a new generation of low-toxicity antimicrobial silver nanoparticles

Abstract

In this study, we describe the rational design and synthesis of a redox-active petide–gallol conjugate and explore its application in the preparation of antimicrobial silver nanoparticles. Increase in acidity and redox activity of peptide–gallol compounds upon pi-stacking was predicted in silico. A representative phenyl alanine–glycine dipeptide–gallol conjugate was synthesized via click chemistry between N-propargyl dipeptide and azidomethyl pyrogallol. The enhanced redox properties of the conjugate were exemplified by rapid formation of silver nanoparticles (Ag NPs) at room temperature without the need of an external capping agent. The nanoparticles formed were found to exhibit prominent antifungal activity against Candida albicans NCIM 3471 along with robust biofilm eradication ability. Thus, our study established the hypothesis that rationally designed peptide–gallol conjugates can be used as biocompatible, redox-active moieties for in situ generation of non-toxic antimicrobial silver nanoparticles in a fast one pot chemical reduction method.

Graphical abstract: π-Stacking assisted redox active peptide–gallol conjugate: synthesis of a new generation of low-toxicity antimicrobial silver nanoparticles

Supplementary files

Article information

Article type
Paper
Submitted
19 May 2016
Accepted
27 Aug 2016
First published
01 Sep 2016

RSC Adv., 2016,6, 85254-85260

π-Stacking assisted redox active peptide–gallol conjugate: synthesis of a new generation of low-toxicity antimicrobial silver nanoparticles

M. Das, K. Senapati, S. S. Panda, P. Bhattacharya, S. Jana, S. M. Mandal and A. Basak, RSC Adv., 2016, 6, 85254 DOI: 10.1039/C6RA13075E

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements