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

被引：31

作者：

Sobolciak, Patrik ^{[1
]}

Spirek, Mario ^{[2
]}

Katrlik, Jaroslav ^{[3
]}

Gemeiner, Peter ^{[3
]}

Lacik, Igor ^{[1
]}

Kasak, Peter ^{[1
,4
]}

机构：

[1] Slovak Acad Sci, Inst Polymer, Ctr Excellence FUN MAT, Bratislava 84541, Slovakia

[2] Masaryk Univ, Dept Biol, Fac Med, Brno 62500, Czech Republic

[3] Slovak Acad Sci, Inst Chem, Bratislava 84538, Slovakia

[4] Qatar Univ, Ctr Adv Mat, Doha, Qatar

来源：

MACROMOLECULAR RAPID COMMUNICATIONS | 2013年 / 34卷 / 08期

关键词：

antibacterial; carboxybetaine ester; dsDNA polyplex; photochemistry; water-soluble polymers; RADICAL POLYMERIZATION; SULFOBETAINE; POLYPLEXES; SURFACES; CARBOXYBETAINE; TRANSFECTION; DEGRADATION; DERIVATIVES; HYDROLYSIS; EFFICIENCY;

D O I：

10.1002/marc.201200823

中图分类号：

O63 [高分子化学（高聚物）];

学科分类号：

070305 ; 080501 ; 081704 ;

摘要：

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.

引用

页码：635 / 639

页数：5

共 36 条

[1] The effect of hydrocarbon chain length, pH, and temperature on the binding and bactericidal effect of amphiphilic betaine esters on Salmonella typhimurium [J].

Ahlström, B ;

Thompson, RA ;

Edebo, L .

APMIS, 1999, 107 (03) :318-324

[2] Acid-degradable polymers for drug delivery: a decade of innovation [J].

Binauld, Sandra ;

Stenzel, Martina H. .

CHEMICAL COMMUNICATIONS, 2013, 49 (21) :2082-2102

[3]

Cao Z., 2011, ANGEW CHEM INT EDIT, V50, P50

[4]

Cheng G, 2008, ANGEW CHEM, V120, P8963, DOI DOI 10.1002/ANGE.200803570

[5] Inhibition of bacterial adhesion and biofilm formation on zwitterionic surfaces [J].

Cheng, Gang ;

Zhang, Zheng ;

Chen, Shengfu ;

Bryers, James D. ;

Jiang, Shaoyi .

BIOMATERIALS, 2007, 28 (29) :4192-4199

[6] Light-Triggered Multifunctionality at Surfaces Mediated by Photolabile Protecting Groups [J].

Cui, Jiaxi ;

San Miguel, Veronica ;

del Campo, Aranzazu .

MACROMOLECULAR RAPID COMMUNICATIONS, 2013, 34 (04) :310-329

[7]

Dey B., 2010, MOL CELL BIOCHEM, V365, P279

[8] Polymer side-chain degradation as a tool to control the destabilization of polyplexes [J].

Funhoff, AM ;

van Nostrum, CF ;

Janssen, APCA ;

Fens, MHAM ;

Crommelin, DJA ;

Hennink, WE .

PHARMACEUTICAL RESEARCH, 2004, 21 (01) :170-176

[9] Biotinylated photocleavable polyethylenimine: Capture and triggered release of nucleic acids from solid supports [J].

Handwerger, Rachel G. ;

Diamond, Scott L. .

BIOCONJUGATE CHEMISTRY, 2007, 18 (03) :717-723

[10] Synthesis and degradation of pH-sensitive linear poly(amidoamine)s [J].

Jain, Rachna ;

Standley, Stephany M. ;

Frechet, Jean M. J. .

MACROMOLECULES, 2007, 40 (03) :452-457

← 1 2 3 4 →