Synthesis of glycopoly(pseudo amino acid)s and their interaction with lectins

• Published in: Reactive & functional polymers Vol. 72; no. 9; pp. 564 - 573
• Main Authors: Lee, Ren-Shen, Peng, Kang-Yu
• Format: Journal Article
• Language: English
• Published: Kidlington Elsevier B.V 01.09.2012; Elsevier
• Subjects: Amino acids; Applied sciences; Binding; Biological and medical sciences; Click chemistry; Derivatives; Exact sciences and technology; General pharmacology; Glycopolymer; Joining; Lectin; Lectins; Medical sciences; Micelles; Organic polymers; Pharmaceutical technology. Pharmaceutical industry; Pharmacology. Drug treatments; Physicochemistry of polymers; Poly(pseudo amino acid); Polymers; Polymers with particular properties; Preparation, kinetics, thermodynamics, mechanism and catalysts; Uptakes; Glycopolymer; Lectin; Click chemistry; Poly(pseudo amino acid); Micelles; Biological properties; Antineoplastic agent; 1,3-Dipolar cycloaddition; End group; Indometacin; Cytotoxicity; Drug carrier; Doxorubicin; Nanoencapsulation; Disaccharide; Glycoside; Release; Amphiphilic polymer; Solution polycondensation; Control release polymer; Ester polymer; Concanavalin A; Experimental study; In vitro; Hela cell line; Non steroidal antiinflammatory agent; Azides; Nitrogen heterocycle polymer; Chemical modification; Internalization; Preparation; Molecular recognition; Kinetics; Aqueous solution; Micellar solution; Nucleophilic substitution
• ISSN: 1381-5148
• DOI: 10.1016/j.reactfunctpolym.2012.06.003

In this study, we developed a novel bioeliminable amphiphilic glycopoly(pseudo amino acid), which was synthesized by the condensation polymerization of N-benzyloxycarbonyl-4-hydroxyl-l-proline (NZHpr) followed by the coupling of an alkynyl-functional sugar derivative to the azido-end group, P(NZHpr)n. The glycosylated P(NZHpr)n polymers formed micelles in the aqueous phase. Selective lectin binding experiments confirmed that the glycosylated P(NZHpr)n can be used in biorecognition applications. The DOX-loaded micelles facilitated improved uptake of DOX by HeLa cells within 2h and were primarily retained in the cytoplasm, whereas free DOX tended to accumulate in the nuclei. The DOX-loaded glucosylated P(NZHpr)n micelles exhibited a substantially lower cytotoxicity compared to free DOX.