Aggregation and pH Responsive Disassembly of a New Acid-Labile Surfactant Synthesized by Thiol-Acrylate Michael Addition Reaction

被引：60

作者：

Dan, Krishna ^{[1
]}

Pan, Rakesh ^{[1
]}

Ghosh, Suhrit ^{[1
]}

机构：

[1] Indian Assoc Cultivat Sci, Polymer Sci Unit, Kolkata 700032, India

来源：

LANGMUIR | 2011年 / 27卷 / 02期

关键词：

CLEAVABLE SURFACTANTS; DRUG-DELIVERY; THIOPROPIONATE LINKAGE; MICELLES; ENE; VESICLES; POLYMER; LIGHT; CONJUGATE; SYSTEMS;

D O I：

10.1021/la104445h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Nucleophilic thiol-acrylate Michael reaction between a hydrophobic thiol and hydrophilic acrylate derivative generated a nonionic surfactant with acid-labile beta-thiopropionate linker. Micellization of the surfactant, its ability to encapsulate hydrophobic dye, acid-induced disruption of the aggregate and pH-selective dye release profile have been revealed in this report. The micellar aggregates were found to be stable under neutral conditions, but they could be disrupted in acidic pH (5.3), and thus the encapsulated hydrophobic dye molecules could be selectively released. Appropriate control experiments revealed that the sulfur atom in the beta-position is essential for acidic hydrolysis of the ester functionality of the surfactant.

引用

页码：612 / 617

页数：6

共 41 条

[1] Ferrocene-containing cationic lipids: Influence of redox state on cell transfection [J].

Abbott, NL ;

Jewell, CM ;

Hays, ME ;

Kondo, Y ;

Lynn, DM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (33) :11576-11577

[2] Preparation and biological characterization of polymeric micelle drug carriers with intracellular pH-triggered drug release property: Tumor permeability, controlled subcellular drug distribution, and enhanced in vivo antitumor efficacy [J].

Bae, Y ;

Nishiyama, N ;

Fukushima, S ;

Koyama, H ;

Yasuhiro, M ;

Kataoka, K .

BIOCONJUGATE CHEMISTRY, 2005, 16 (01) :122-130

[3] Convergent synthesis of 3-arm star polymers from RAFT-prepared poly(N,N-diethylacrylamide) via a thiol-ene click reaction [J].

Chan, Justin W. ;

Yu, Bing ;

Hoyle, Charles E. ;

Lowe, Andrew B. .

CHEMICAL COMMUNICATIONS, 2008, (40) :4959-4961

[4] Nucleophile-Initiated Thiol-Michael Reactions: Effect of Organocatalyst, Thiol, and Ene [J].

Chan, Justin W. ;

Hoyle, Charles E. ;

Lowe, Andrew B. ;

Bowman, Mark .

MACROMOLECULES, 2010, 43 (15) :6381-6388

[5] Sequential Phosphine-Catalyzed, Nucleophilic Thiol-Ene/Radical-Mediated Thiol-Yne Reactions and the Facile Orthogonal Synthesis of Polyfunctional Materials [J].

Chan, Justin W. ;

Hoyle, Charles E. ;

Lowe, Andrew B. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (16) :5751-+

[6] Self-assembly of light-sensitive sufactants [J].

Eastoe, J ;

Vesperinas, A .

SOFT MATTER, 2005, 1 (05) :338-347

[7] EXTRACELLULAR PH DISTRIBUTION IN HUMAN TUMORS [J].

ENGIN, K ;

LEEPER, DB ;

CATER, JR ;

THISTLETHWAITE, AJ ;

TUPCHONG, L ;

MCFARLANE, JD .

INTERNATIONAL JOURNAL OF HYPERTHERMIA, 1995, 11 (02) :211-216

[8]

Evans DF., 1999, COLLOIDAL DOMAIN

[9]

Gerweck LE, 1996, CANCER RES, V56, P1194

[10] Tunable disassembly of micelles using a redox trigger [J].

Ghosh, Suhrit ;

Irvin, Katharine ;

Thayumanavan, S. .

LANGMUIR, 2007, 23 (15) :7916-7919

← 1 2 3 4 5 →