Thiol-substituted copolylactide: synthesis, characterization and post-polymerization modification using thiol-ene chemistry

被引：11

作者：

Kalelkar, Pranav P. ^{[1
]}

Collard, David M. ^{[1
]}

机构：

[1] Georgia Inst Technol, Sch Chem & Biochem, Atlanta, GA 30332 USA

来源：

POLYMER CHEMISTRY | 2018年 / 9卷 / 08期

关键词：

RING-OPENING POLYMERIZATION; DRUG-DELIVERY SYSTEMS; L-MALIC ACID; CLICK CHEMISTRY; BIOMEDICAL APPLICATIONS; BIODEGRADABLE POLYMER; CHEMICAL-MODIFICATION; POLY(LACTIC ACID); BLOCK-COPOLYMERS; GLUTAMIC-ACID;

D O I：

10.1039/c7py01930k

中图分类号：

O63 [高分子化学（高聚物）];

学科分类号：

070305 ; 080501 ; 081704 ;

摘要：

The synthesis of a copolylactide that is substituted with pendent thiol side chains is described. The copolymer is prepared by the ring-opening copolymerization of a new monomer, 3,6-bis(4-methoxybenzylthiomethyl)-1,4-dioxane-2,5-dione, with L-lactide to afford poly(lactide-co-(4-methoxybenzylthio) methylglycolide) (MBT-PL). Debenzylation of MBT-PL affords poly(lactide-co-mercaptomethylglycolide), thiol-PL. We demonstrate the modification of thiol-PL by addition to a variety of electron-deficient alkenes: N-phenylmaleimide, N-phenyl acrylate and acrylonitrile.

引用

页码：1022 / 1031

页数：10

共 63 条

[41]

Ouchi T, 1997, J POLYM SCI POL CHEM, V35, P377

[42] Synthesis of a block copolymer of L-lactide and depsipeptide with pendant thiol groups [J].

Ouchi, T ;

Seike, H ;

Miyazaki, H ;

Tasaka, F ;

Ohya, Y .

DESIGNED MONOMERS AND POLYMERS, 2000, 3 (03) :279-287

[43] Ambient temperature polymer modification by in situ phototriggered deprotection and thiol-ene chemistry [J].

Pauloehrl, Thomas ;

Delaittre, Guillaume ;

Bastmeyer, Martin ;

Barner-Kowollik, Christopher .

POLYMER CHEMISTRY, 2012, 3 (07) :1740-1749

[44] Ring-opening polymerization of an O-carboxyanhydride monomer derived from L-malic acid [J].

Pounder, Ryan J. ;

Fox, David J. ;

Barker, Ian A. ;

Bennison, Michael J. ;

Dove, Andrew P. .

POLYMER CHEMISTRY, 2011, 2 (10) :2204-2212

[45] Synthesis and Organocatalytic Ring-Opening Polymerization of Cyclic Esters Derived from L-Malic Acid [J].

Pounder, Ryan J. ;

Dove, Andrew P. .

BIOMACROMOLECULES, 2010, 11 (08) :1930-1939

[46] Towards poly(ester) nanoparticles: recent advances in the synthesis of functional poly(ester)s by ring-opening polymerization [J].

Pounder, Ryan J. ;

Dove, Andrew P. .

POLYMER CHEMISTRY, 2010, 1 (03) :260-271

[47] Preparation of Polymeric Prodrug Paclitaxel-Poly(lactic acid)-b-Polyisobutylene and Its Application in Coatings of a Drug Eluting Stent [J].

Ren, Kai ;

Zhang, Mingzu ;

He, Jinlin ;

Wu, Yixian ;

Ni, Peihong .

ACS APPLIED MATERIALS & INTERFACES, 2015, 7 (21) :11263-11271

[48] Mechanistic Studies on the Degradation and Protein Release Characteristics of Poly(lactic-co-glycolic-co-hydroxymethylglycolic acid) Nanospheres [J].

Samadi, N. ;

van Nostrum, C. F. ;

Vermonden, T. ;

Amidi, M. ;

Hennink, W. E. .

BIOMACROMOLECULES, 2013, 14 (04) :1044-1053

[49] When Functionalization of PLA Surfaces Meets Thiol-Yne Photochemistry: Case Study with Antibacterial Polyaspartamide Derivatives [J].

Sardo, Carla ;

Nottelet, Benjamin ;

Triolo, Daniela ;

Giammona, Gaetano ;

Garric, Xavier ;

Lavigne, Jean-Philippe ;

Cavallaro, Gennara ;

Coudane, Jean .

BIOMACROMOLECULES, 2014, 15 (11) :4351-4362

[50] Lactic acid-based functionalized polymers via copolymerization and chemical modification [J].

Saulnier, B ;

Ponsart, S ;

Coudane, J ;

Garreau, H ;

Vert, M .

MACROMOLECULAR BIOSCIENCE, 2004, 4 (03) :232-237

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