The hydrolysis of cationic polycarboxybetaine esters to zwitterionic polycarboxybetaines with controlled properties.
In this work, we report a new class of materials, cationic polycarboxybetaine esters, which have unique properties when they interact with proteins, DNAs, and bacteria. These cationic polymers can be converted to nontoxic and nonfouling zwitterionic polymers upon their hydrolysis. Due to their unique properties, they are very promising for a wide range of applications, such as highly effective gene delivery carriers and environmentally friendly antimicrobial coatings. Three positively charged polyacrylamides, of which the pedant groups bear carboxybetaine ester groups, were synthesized. These three polymers have different spacer groups between the quaternary ammonium and the ester groups. Their hydrolysis behaviors were studied using proton NMR under different NaOH concentrations. Their interactions with biomolecules and microorganisms before and after hydrolysis were demonstrated by protein adsorption/resistance, DNA condensation/release, and antimicrobial properties. The polymers were grafted onto a gold-coated surface covered with initiators using surface-initiated atom transfer radical polymerization (ATRP). Fibrinogen adsorption was measured by surface plasmon resonance (SPR) sensors. While the polymer-grafted surfaces have high protein adsorption, the surfaces became nonfouling after hydrolysis. Linear polymers were also synthesized and DNA/polymer complexes were evaluated. Agarose gel electrophoresis shows that DNA can be condensed into nanoparticles by the cationic polymers before hydrolysis and released from the DNA/polymer complexes upon the hydrolysis of the cationic polymers into zwitterionic polymers. The complexes formed were characterized by dynamic light scattering measurements. In addition, the interactions of linear polymers with bacteria were also evaluated. The polycarboxybetaine ester with a pentene spacer exhibits evident antimicrobial properties when they are incubated with Gram negative bacteria (Escherichia Coli). The polymer can be converted to a nontoxic polycarboxybetaine after hydrolysis. This work shows that the biological properties of polycarboxybetaine esters can be dramatically changed via controlled hydrolysis.
Zhang
Zheng
Z
Department of Chemical Engineering, University of Washington, Seattle, WA 98195, USA.
Cheng
Gang
G
Carr
Louisa R
LR
Vaisocherová
Hana
H
Chen
Shengfu
S
Jiang
Shaoyi
S
D020106:Acrylamide / Q000737:chemistry; D000327:Adsorption / Q000187:drug effects; D000890:Anti-Infective Agents / Q000494:pharmacology; D001622:Betaine / Q000378:metabolism*; D004247:DNA / Q000378:metabolism; D004587:Electrophoresis, Agar Gel; D004926:Escherichia coli / Q000187:drug effects; D004952:Esters / Q000378:metabolism*; D005340:Fibrinogen / Q000378:metabolism; D006868:Hydrolysis / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D010957:Plasmids / Q000378:metabolism; D011108:Polymers / Q000378:metabolism*; D012996:Solutions; D020349:Surface Plasmon Resonance
D000890:Anti-Infective Agents; D004952:Esters; D011108:Polymers; D012996:Solutions; D020106:Acrylamide; D001622:Betaine; D005340:Fibrinogen; D004247:DNA