Synthesis and characterization of cinnamic acid conjugated N-(2-hydroxy)-propyl-3-trimethylammonium chitosan chloride derivatives: A hybrid flocculant with antibacterial activity

Min Wang; Lin Yue; Sobia Niazi; Imran Mahmood Khan; Yin Zhang; Zhouping Wang

doi:10.1016/j.ijbiomac.2022.03.075

Synthesis and characterization of cinnamic acid conjugated N-(2-hydroxy)-propyl-3-trimethylammonium chitosan chloride derivatives: A hybrid flocculant with antibacterial activity

Int J Biol Macromol. 2022 May 1:206:886-895. doi: 10.1016/j.ijbiomac.2022.03.075. Epub 2022 Mar 17.

Authors

Min Wang¹, Lin Yue², Sobia Niazi¹, Imran Mahmood Khan¹, Yin Zhang³, Zhouping Wang⁴

Affiliations

¹ State Key Laboratory of Food Science and Technology, Jiangnan University, Lihu Road 1800, Wuxi 214122, PR China; School of Food Science and Technology, Jiangnan University, Lihu Road 1800, Wuxi 214122, PR China.
² State Key Laboratory of Food Science and Technology, Jiangnan University, Lihu Road 1800, Wuxi 214122, PR China; School of Food Science and Technology, Jiangnan University, Lihu Road 1800, Wuxi 214122, PR China; International Joint Laboratory on Food Safety, Jiangnan University, Lihu Road 1800, Wuxi 214122, PR China; Collaborative Innovation Center of Food Safety and Quality Control, Jiangnan University, Lihu Road 1800, Wuxi 214122, PR China. Electronic address: yuelin@jiangnan.edu.cn.
³ Key Laboratory of Meat Processing of Sichuan, Chengdu University, Chengdu 610106, PR China.
⁴ State Key Laboratory of Food Science and Technology, Jiangnan University, Lihu Road 1800, Wuxi 214122, PR China; School of Food Science and Technology, Jiangnan University, Lihu Road 1800, Wuxi 214122, PR China; International Joint Laboratory on Food Safety, Jiangnan University, Lihu Road 1800, Wuxi 214122, PR China; Collaborative Innovation Center of Food Safety and Quality Control, Jiangnan University, Lihu Road 1800, Wuxi 214122, PR China; Key Laboratory of Meat Processing of Sichuan, Chengdu University, Chengdu 610106, PR China. Electronic address: wangzp@jiangnan.edu.cn.

PMID: 35306015
DOI: 10.1016/j.ijbiomac.2022.03.075

Abstract

The modified natural biopolymers, recognized as environmentally friendly flocculants, are gaining tremendous attention in the field of water treatment. In this study, a novel hybrid flocculant with antibacterial activity, cinnamic acid (CA) conjugated N-(2-hydroxy)-propyl-3-trimethylammonium chitosan chloride (HTCC) derivative (HTCC-CA), was prepared via quaternary ammonium and amide reactions. The characterization, flocculation, and antibacterial activities were carried out to access the structural properties and potential application. The results of UV-vis, FT-TR, and ¹H NMR confirmed the successful synthesis of HTCC-CA1-3 derivatives. XRD and TGA revealed the lower crystallinity and thermal stability of HTCC-CA1-3 derivatives than chitosan (CS). Bacterial flocculation and antibacterial tests indicated the excellent flocculation effect of HTCC-CA1-3 derivatives and showed high antibacterial activity for Escherichia coli suspension. Moreover, the mechanism of action of the derivatives was investigated via zeta potential measurements and scanning electron microscope, which can be summed up as the effective interaction between charges. The results proved that HTCC-CA derivatives are promising agents for wastewater treatment.

Keywords: Antibacterial activity; Chemical modification; Chitosan; Cinnamic acid; Flocculation.

MeSH terms

Anti-Bacterial Agents / chemistry
Anti-Bacterial Agents / pharmacology
Chitosan* / chemistry
Chlorides
Cinnamates / pharmacology
Escherichia coli

Substances

Anti-Bacterial Agents
Chlorides
Cinnamates
cinnamic acid
Chitosan