Synthesis and characterization of novel chitosan derivatives (containing dipyridinium quaternary salts) with antimicrobial potential

Andreea Veronica Dediu Botezatu; Roxana-Mihaela Apetrei; Iuliana Florina Costea Nour; Vasilica Barbu; Leontina Grigore-Gurgu; Florina Botez; Rodica Mihaela Dinica; Bianca Furdui; Geta Cârâc

doi:10.1016/j.carres.2023.108964

Synthesis and characterization of novel chitosan derivatives (containing dipyridinium quaternary salts) with antimicrobial potential

Carbohydr Res. 2023 Dec:534:108964. doi: 10.1016/j.carres.2023.108964. Epub 2023 Oct 19.

Authors

Andreea Veronica Dediu Botezatu¹, Roxana-Mihaela Apetrei², Iuliana Florina Costea Nour³, Vasilica Barbu⁴, Leontina Grigore-Gurgu⁵, Florina Botez⁶, Rodica Mihaela Dinica⁷, Bianca Furdui⁸, Geta Cârâc⁹

Affiliations

¹ (")Dunarea de Jos" University of Galati, Faculty of Science and Environment, Department of Chemistry, Physics and Environment, Domneasca Street 111, 800201, Galati, Romania. Electronic address: andreea.botezatu@ugal.ro.
² (")Dunarea de Jos" University of Galati, Faculty of Science and Environment, Department of Chemistry, Physics and Environment, Domneasca Street 111, 800201, Galati, Romania; "Dunarea de Jos" University of Galai, Rexdan Research Infrastructure, George Coșbuc Bdv. 98, 800385, Galati, Romania. Electronic address: mihaelaapetrei21@yahoo.com.
³ (")Dunarea de Jos" University of Galati, Faculty of Science and Environment, Department of Chemistry, Physics and Environment, Domneasca Street 111, 800201, Galati, Romania. Electronic address: iulianaflorinanour@gmail.com.
⁴ ('')Dunarea de Jos" University of Galati, Faculty of Food Science and Engineering, Domneasca Street 111, 800201, Galati, Romania. Electronic address: Vasilica.Barbu@ugal.ro.
⁵ ('')Dunarea de Jos" University of Galati, Faculty of Food Science and Engineering, Domneasca Street 111, 800201, Galati, Romania. Electronic address: Leontina.Gurgu@ugal.ro.
⁶ University of Bucharest, Faculty of Biology, Department of Systems Ecology, Splaiul Independenţei no. 91-95, District 5, 050095, Bucharest, Romania. Electronic address: florina.botez@bio.unibuc.ro.
⁷ (")Dunarea de Jos" University of Galati, Faculty of Science and Environment, Department of Chemistry, Physics and Environment, Domneasca Street 111, 800201, Galati, Romania. Electronic address: Rodica.Dinica@ugal.ro.
⁸ (")Dunarea de Jos" University of Galati, Faculty of Science and Environment, Department of Chemistry, Physics and Environment, Domneasca Street 111, 800201, Galati, Romania. Electronic address: bfurdui@ugal.ro.
⁹ (")Dunarea de Jos" University of Galati, Faculty of Science and Environment, Department of Chemistry, Physics and Environment, Domneasca Street 111, 800201, Galati, Romania. Electronic address: geta.carac@ugal.ro.

PMID: 37925873
DOI: 10.1016/j.carres.2023.108964

Abstract

Chitosan derivatives are versatile materials, biocompatible and biodegradable, that can be tailor-made to suit specific biomedical applications. In this study, two N-heterocyclic salts (N,N'-diphenacyl-[4,4'-dipyridinium] dibromide (DP) and N,N'-diphenacyl-1,2-bis-(4-pyridinium)ethane dibromide (DPE)) were used for chitosan functionalization to enhance its antimicrobial potential. Physico-chemical characterization of the newly synthesized derivatives (Ch-DP and Ch-DPE) was performed by elemental analysis, spectrometry (UV-Vis, FTIR), electrochemistry (OCP, CV), and electron microscopy (SEM) proving that the highest degree of functionalization was obtained for Ch-DP. The antimicrobial effect of chitosan functionalization was further tested in terms of its interaction with Listeria monocytogenes Scott A, and Staphylococcus aureus ATCC 25923, as Gram-positive bacteria and Escherichia coli ATCC 25922, as Gram-negative bacterium, respectively, showing that the Ch-DP had a good inhibitory activity compared with Ch-DPE.

Keywords: Antibacterial activity; Chitosan derivatives; Functional materials; N-heterocyclic dipyridinium salts.

MeSH terms

Anti-Bacterial Agents / chemistry
Anti-Infective Agents* / chemistry
Chitosan* / chemistry
Chitosan* / pharmacology
Escherichia coli
Microbial Sensitivity Tests
Salts / pharmacology

Substances

Anti-Bacterial Agents
Chitosan
Salts
Anti-Infective Agents