Redox tunable delivery systems: sweet block copolymer micelles via thiol-(bromo) maleimide conjugation

被引:15
作者
Petrelli, Antoine [1 ]
Borsali, Redouane [1 ]
Fort, Sebastien [1 ]
Halila, Sami [1 ]
机构
[1] Univ Grenoble Alpes, CNRS, CERMAV, F-38000 Grenoble, France
关键词
POLYMERIC MICELLES; NANOPARTICLES; THIOL; ENCAPSULATION; STABILITY;
D O I
10.1039/c6cc07136h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Oligosaccharide-based block copolymers (OBCPs) are synthesized by thiol click conjugation using reducing-end thiol-containing xyloglucooligosaccharides and maleimide- or bromomaleimide-terminated polycaprolactone. The self-assembled OBCPs in aqueous solution lead to redox-sensitive micelles with different responsiveness. This distinguishing feature allows us to control the release of entrapped hydrophobic Nile red by mixing both OBCPs.
引用
收藏
页码:12202 / 12205
页数:4
相关论文
共 25 条
[1]  
Baker J. R., 2009, CHEM COMMUN, P6583
[2]   Tunable Degradation of Maleimide-Thiol Adducts in Reducing Environments [J].
Baldwin, Aaron D. ;
Kiick, Kristi L. .
BIOCONJUGATE CHEMISTRY, 2011, 22 (10) :1946-1953
[3]   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
[4]   Sulfated Glycosaminoglycan-Based Block Copolymer: Preparation of Biocompatible Chondroitin Sulfate-b-poly(lactic acid) Micelles [J].
Fajardo, Andre R. ;
Guerry, Alexandre ;
Britta, Elizandra A. ;
Nakamura, Celso V. ;
Muniz, Edvani C. ;
Borsali, Redouane ;
Halila, Sami .
BIOMACROMOLECULES, 2014, 15 (07) :2691-2700
[5]   Long-Term Stabilization of Maleimide-Thiol Conjugates [J].
Fontaine, Shaun D. ;
Reid, Ralph ;
Robinson, Louise ;
Ashley, Gary W. ;
Santi, Daniel V. .
BIOCONJUGATE CHEMISTRY, 2015, 26 (01) :145-152
[6]   Enzyme Degradable Polymersomes from Hyaluronic Acid-block-poly(ε-caprolactone) Copolymers for the Detection of Enzymes of Pathogenic Bacteria [J].
Haas, Simon ;
Hain, Nicole ;
Raoufi, Mohammad ;
Handschuh-Wang, Stephan ;
Wang, Tao ;
Jiang, Xin ;
Schoenherr, Holger .
BIOMACROMOLECULES, 2015, 16 (03) :832-841
[7]   POLYMERIC MICELLES - THEIR RELAXATION KINETICS [J].
HALPERIN, A ;
ALEXANDER, S .
MACROMOLECULES, 1989, 22 (05) :2403-2412
[8]   Thiol-click chemistry: a multifaceted toolbox for small molecule and polymer synthesis [J].
Hoyle, Charles E. ;
Lowe, Andrew B. ;
Bowman, Christopher N. .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (04) :1355-1387
[9]   Self-hydrolyzing maleimides improve the stability and pharmacological properties of antibody-drug conjugates [J].
Lyon, Robert P. ;
Setter, Jocelyn R. ;
Bovee, Tim D. ;
Doronina, Svetlana O. ;
Hunter, Joshua H. ;
Anderson, Martha E. ;
Balasubramanian, Cindy L. ;
Duniho, Steven M. ;
Leiske, Chris I. ;
Li, Fu ;
Senter, Peter D. .
NATURE BIOTECHNOLOGY, 2014, 32 (10) :1059-+
[10]   Dual effect of thiol addition on fluorescent polymeric micelles: ON-to-OFF emissive switch and morphology transition [J].
Mabire, Anne B. ;
Robin, Mathew P. ;
Willcock, Helen ;
Pitto-Barry, Anais ;
Kirby, Nigel ;
O'Reilly, Rachel K. .
CHEMICAL COMMUNICATIONS, 2014, 50 (78) :11492-11495