Biological properties of novel polysuccinimide derivatives synthesized via quaternary ammonium grafting. (15th May 2020)

• Record Type: Journal Article
• Authors: Velazco-de-la-Garza, Jaqueline; Avérous, Luc; Sosa-Santillán, Gerardo de Jesús; Pollet, Eric; Zugasti-Cruz, Alejandro; Sierra-Rivera, Crystel Aleyvick; Pérez-Aguilar, Nancy Verónica; Oyervides-Muñoz, Ernesto
• Is Part Of: European polymer journal. Volume 131(2020)
• Publication Date: 2020-05-15
• Subjects: Polysuccinimide -- Quaternary ammonium -- Hemolytic assay -- Biological activity; PSI Polysuccinimide -- QA-Br 4-bromobutyl-quinolinium bromide -- BZK-Br 4-bromobutyl-benzalkonium bromide -- QA-PSI Quinolinium polysuccinimide -- BZK-PSI Benzalkonium polysuccinimide -- MIC Minimum inhibitory concentration -- MBC Minimum bactericidal concentration -- MTT 3-(4, 5-dimethylthiazol-2-yl)-2, 5-diphenyltetrazolium bromide -- DMEM/F-12 Dulbeccós modified eaglés medium/nutrient mixture F-12 ham -- 3T3 Murine fibroblast -- HeLa Human cervical adenocarcinoma -- 4T1 Murine breast cancer -- HepG2 Human hepatocellular carcinoma -- FBS fetal bovine serum -- P Percentage of proliferation -- DMSO Dimethylsulfoxide -- TGA Thermogravimetric analysis -- DTA Differential thermal analysis -- DS Degree of substitution -- MH Müller-Hinton -- K2-EDTA dipotassium ethylenediaminetetraacetic acid -- MeCN Acetonitrile -- PAspNa Sodium polyaspartate -- SEC size exclusion chromatography; Polymers -- Periodicals; Polymerization -- Periodicals; Polymères -- Périodiques; Polymérisation -- Périodiques; Polymerization; Polymers; Periodicals; Electronic journals; 547.705
• DOI: 10.1016/j.eurpolymj.2020.109705
• Languages: English
• ISSNs: 0014-3057

Abstract

Graphical abstract: Highlights: Two quaternary ammonium salts having a bromide end group were synthesized. Polysuccinimide derivatives were synthesized via quaternary ammonium grafting. The Chemical structures of the derivatives were supported by NMR and FTIR. Biological properties of the polysuccinimide derivatives were evaluated. Abstract: Two novel polysuccinimide (PSI) derivatives with antibacterial properties were synthesized by the reaction of polysuccinimide with different quaternary ammonium salts with an active terminal group. 4-bromobutyl-quinolinium bromide and 4-bromobutyl-benzalkonium bromide were synthesized from a quaternization reaction between 1, 4-dibromobutane and a tertiary amine (quinoline and N, N-dimethylbenzylamine). These ammonium salts with a bromide end group were chemically grafted along the polysuccinimide chains by quaternization of the nitrogen atoms of PSI. The chemical structures of these PSI derivatives were characterized by 1 H NMR analysis and FT-IR spectra. Thermal stability of these macromolecules was studied by thermo-gravimetric analysis. Antibacterial activity against E. coli strains was determined by the minimum inhibitory concentration and the minimum bactericidal concentration. In all the cases, it was possible to grant antibacterial properties to the polysuccinimide derivatives. Finally, hemolysis and 3-(4, 5-dimethylthiazol-2-yl)-2, 5-diphenyltetrazolium bromide (MTT) assays were performed. PSI derivatives caused a lightly hemolytic effects on isolated human erythrocytes and murine fibroblast cell line, decreasing the cell proliferation of cancer cervical and breast cell lines.