Synthesis of poly(lactide-co-glycolide-co-ε-caprolactone)-graft-mannosylated poly(ethylene oxide) copolymers by combination of "clip" and "click" chemistries

Biomacromolecules
Hélène FreichelsChristine Jérôme

Abstract

Poly(lactide-co-glycolide) (PLGA) is extensively used in pharmaceutical applications, for example, in targeted drug delivery, because of biocompatibility and degradation rate, which is easily tuned by the copolymer composition. Nevertheless, synthesis of sugar-labeled amphiphilic copolymers with a PLGA backbone is quite a challenge because of high sensitivity to hydrolytic degradation. This Article reports on the synthesis of a new amphiphilic copolymer of PLGA grafted by mannosylated poly(ethylene oxide) (PEO). A novel building block, that is, α-methoxy-ω-alkyne PEO-clip-N-hydroxysuccinimide (NHS) ester, was prepared on purpose by photoreaction of a diazirine containing molecular clip. This PEO block was mannosylated by reaction of the NHS ester groups with an aminated sugar, that is, 2-aminoethyl-α-d-mannopyroside. Then, the alkyne ω-end-group of PEO was involved in a copper alkyne- azide coupling (CuAAC) with the pendent azides of the aliphatic copolyester. The targeted mannose-labeled poly(lactide-co-glycolide-co-ε-caprolactone)-graft-poly(ethylene oxide) copolymer was accordingly formed. Copolymerization of d,l-lactide and glycolide with α-chloro-ε-caprolactone, followed by substitution of chlorides by azides provided the ...Continue Reading

References

Dec 26, 2001·Chemical Reviews·K E UhrichK M Shakesheff
Feb 22, 2002·Biotechnology and Bioengineering·Jun Jin YoonTae Gwan Park
May 31, 2003·Somatic Cell and Molecular Genetics·Sandra S DieboldMartin Zenke
Jun 3, 2004·Journal of Biomedical Materials Research. Part a·Fenghua MengJan Feijen
Mar 16, 2005·Analytical Biochemistry·Tatsuya MasukoYuan C Lee
Jul 19, 2005·Biomaterials·Fatiha ChellatL'Hocine Yahia
Oct 26, 2005·Chemical Communications : Chem Comm·Raphaël RivaPhilippe Lecomte
Nov 18, 2005·Journal of Colloid and Interface Science·Annegret HildebrandReinhard H H Neubert
Nov 24, 2005·International Journal of Pharmaceutics·Donald E Owens, Nicholas A Peppas
Jul 4, 2006·Pharmacology & Therapeutics·Nobuhiro Nishiyama, Kazunori Kataoka
Oct 20, 2006·Journal of Nanoscience and Nanotechnology·Hesham H SalmanJuan M Irache
Oct 31, 2007·Journal of Drug Targeting·Abdullah MahmudAfsaneh Lavasanifar
Dec 18, 2007·Journal of Controlled Release : Official Journal of the Controlled Release Society·Raghavendra C MundargiTejraj M Aminabhavi
May 20, 2008·International Journal of Pharmaceutics·Tamer ShehataToshikiro Kimura
Jun 24, 2008·Journal of Drug Targeting·Farnaz EsmaeiliRassoul Dinarvand
Feb 20, 2009·Biomacromolecules·Vincent PourcelleJacqueline Marchand-Brynaert
May 5, 2009·European Journal of Pharmaceutics and Biopharmaceutics : Official Journal of Arbeitsgemeinschaft Für Pharmazeutische Verfahrenstechnik E.V·Virginie FievezVéronique Préat
May 14, 2009·Expert Review of Molecular Diagnostics·Jian-Ming LüChangyi Chen
Feb 17, 2010·Journal of Controlled Release : Official Journal of the Controlled Release Society·Luis J CruzCarl G Figdor
Mar 26, 2011·Macromolecular Rapid Communications·Hélène FreichelsChristine Jérôme

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Citations

Jul 3, 2013·ACS Applied Materials & Interfaces·Jian-Min ShenShuang Xu
Jan 22, 2014·Langmuir : the ACS Journal of Surfaces and Colloids·Laura RussoLaura Cipolla
Mar 5, 2013·Advanced Drug Delivery Reviews·Anne des RieuxVéronique Préat
Jan 15, 2015·Pharmaceutical Research·Feng QiZhiguo Su
Feb 5, 2013·Pharmacological Research : the Official Journal of the Italian Pharmacological Society·Jian-Min ShenFeng Yue
Apr 18, 2016·Carbohydrate Research·Xiao-Peng HeGuo-Rong Chen
Mar 26, 2013·Journal of Controlled Release : Official Journal of the Controlled Release Society·Joana M SilvaHelena F Florindo
Dec 17, 2014·Frontiers in Chemistry·João ConniotTeresa S Barata
Feb 21, 2014·Journal of Materials Chemistry. B, Materials for Biology and Medicine·Tao CaiEn-Tang Kang
Mar 17, 2020·Drug Delivery and Translational Research·Arpit BhargavaPradyumna Kumar Mishra

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