Light-Switchable Polymer from Cationic to Zwitterionic Form: Synthesis, Characterization, and Interactions with DNA and Bacterial Cells

• Published in: Macromolecular rapid communications. Vol. 34; no. 8; pp. 635 - 639
• Main Authors: Sobolčiak, Patrik, Špírek, Mário, Katrlík, Jaroslav, Gemeiner, Peter, Lacík, Igor, Kasák, Peter
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 25.04.2013; WILEY‐VCH Verlag; Wiley; Wiley Subscription Services, Inc
• Subjects: Acrylamides - chemistry; antibacterial; Applied sciences; carboxybetaine ester; Cations - chemistry; Deoxyribonucleic acid; DNA; DNA - chemistry; DNA - metabolism; dsDNA polyplex; Escherichia coli; Escherichia coli - drug effects; Escherichia coli - metabolism; Exact sciences and technology; Free Radicals - chemistry; Light; Organic polymers; photochemistry; Photolysis; Physicochemistry of polymers; Polymers; Polymers - chemical synthesis; Polymers - chemistry; Polymers - pharmacology; Polymers with particular properties; Preparation, kinetics, thermodynamics, mechanism and catalysts; Proteins; Quaternary Ammonium Compounds - chemistry; Surface Plasmon Resonance; water-soluble polymers; Biological properties; Nitro compound; Polyplex; dsDNA polyplex; Drug carrier; antibacterial; Photochemical reaction; Double stranded DNA; Binding capacity; Debenzylation; Release; Carboxylate polymer; Polyampholyte; Control release polymer; Photoinduced effect; carboxybetaine ester; Bactericidal effect; Methacrylamide derivative polymer; Polyelectrolyte; Chemical modification; Free radical polymerization; Light sensitive polymer; photochemistry; Preparation; water-soluble polymers; Kinetics; Aqueous solution; Antibacterial agent; Quaternary ammonium polymer
• ISSN: 1022-1336; 1521-3927
• DOI: 10.1002/marc.201200823

A novel cationic polymer poly(N,N‐dimethyl‐N‐[3‐(methacroylamino) propyl]‐N‐[2‐[(2‐nitrophenyl)methoxy]‐2‐oxo‐ethyl]ammonium chloride) is synthesized by free‐radical polymerization of N‐[3‐(dimethylamino)propyl] methacrylamide and subsequent quaternization with o‐nitrobenzyl 2‐chloroacetate. The photolabile o‐nitrobenzyl carboxymethyl pendant moiety is transformed to the zwitterionic carboxybetaine form upon the irradiation at 365 nm. This feature is used to condense and, upon the light irradiation, to release double‐strand DNA tested by gel electrophoresis and surface plasmon resonance experiments as well as to switch the antibacterial activity to non‐toxic character demonstrated for Escherichia coli bacterial cells in solution and at the surface using the self‐assembled monolayers. A polymer containing photolabile o‐nitrobenzyl carboxymethyl pendant on a quaternary ammonium moiety in the monomer unit is synthesized. Light‐induced switch from cationic to zwitterionic form is utilized for controlled interaction with DNA and bacteria.