Synthesis, characterization and antibacterial activity of new fluorescent chitosan derivatives

Hana Přichystalová; Numan Almonasy; A M Abdel-Mohsen; Rasha M Abdel-Rahman; Moustafa M G Fouda; L Vojtova; Libor Kobera; Zdenek Spotz; Ladislav Burgert; J Jancar

doi:10.1016/j.ijbiomac.2014.01.050

Synthesis, characterization and antibacterial activity of new fluorescent chitosan derivatives

Int J Biol Macromol. 2014 Apr:65:234-40. doi: 10.1016/j.ijbiomac.2014.01.050. Epub 2014 Jan 25.

Authors

Affiliations

¹ Institute of Organic Chemistry and Technology, Faculty of Chemical Technology, University of Pardubice, Studentská 573, Pardubice CZ-532 10, Czech Republic; Institute of Polymeric Materials, Faculty of Chemical Technology, University of Pardubice, Studentská 573, Pardubice CZ-532 10, Czech Republic.
² Institute of Organic Chemistry and Technology, Faculty of Chemical Technology, University of Pardubice, Studentská 573, Pardubice CZ-532 10, Czech Republic; Institute of Polymeric Materials, Faculty of Chemical Technology, University of Pardubice, Studentská 573, Pardubice CZ-532 10, Czech Republic. Electronic address: [email protected].
³ Central European Institute of Technology (CEITEC), Brno University of Technology, Brno, Czech Republic; Textile Research Divisions, National Research Centre, Dokki, Cairo, Egypt. Electronic address: [email protected].
⁴ Institute of Organic Chemistry and Technology, Faculty of Chemical Technology, University of Pardubice, Studentská 573, Pardubice CZ-532 10, Czech Republic.
⁵ Petrochemical Research Chair, Chemistry Department, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia; Textile Research Divisions, National Research Centre, Dokki, Cairo, Egypt.
⁶ Central European Institute of Technology (CEITEC), Brno University of Technology, Brno, Czech Republic.
⁷ Institute of Macromolecular Chemistry, Academy of Sciences of the Czech Republic, Heyrovského nám. 2, 162 06 Praha 6, Czech Republic.
⁸ Institute of Polymeric Materials, Faculty of Chemical Technology, University of Pardubice, Studentská 573, Pardubice CZ-532 10, Czech Republic.
⁹ Central European Institute of Technology (CEITEC), Brno University of Technology, Brno, Czech Republic; Institute of Materials Chemistry, Brno University of Technology, Czech Republic.

PMID: 24472505
DOI: 10.1016/j.ijbiomac.2014.01.050

Abstract

The present work aims to the development of innovative new derivatives of chitosan that can be used for medical applications. This innovation is based on the synthesis and characterization of chitosan-g-aminoanthracene derivatives. Thus, N-(anthracen-9-yl)-4,6-dichloro-[1,3,5]-triazin-2-amine (AT) reacted with chitosan by the following steps: at first, cyanuric chloride reacted with 9-aminoanthracene to obtain N-(anthracen-9-yl)-4,6-dichloro-[1,3,5]-triazin-2-amine (AT), then the AT reacted with chitosan to obtain (CH-g-AT). The final product of CH-g-AT was separated, purified and re-crystallized by dioxane. The structure of the prepared chitosan derivatives was confirmed by FTIR-ATR, solid-NMR, TGA, X-RD, and DSC. The new chitosan derivatives showed fluorescence spectra in liquid and in solid state as well. CH-g-AT showed also high antibacterial activity against gram -ve species (Escherichia coli).

Keywords: Antibacterial activity; Chitosan derivatives; Fluorescence.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Anti-Bacterial Agents / chemical synthesis*
Anti-Bacterial Agents / chemistry
Anti-Bacterial Agents / pharmacology*
Chemistry Techniques, Synthetic
Chitosan / chemical synthesis*
Chitosan / chemistry
Chitosan / pharmacology*
Drug Stability
Escherichia coli / drug effects
Fluorescent Dyes / chemical synthesis*
Fluorescent Dyes / chemistry
Fluorescent Dyes / pharmacology*
Temperature

Substances

Anti-Bacterial Agents
Fluorescent Dyes
Chitosan