Tags

Type your tag names separated by a space and hit enter

Lipase-catalyzed synthesis of azido-functionalized aliphatic polyesters towards acid-degradable amphiphilic graft copolymers.
Soft Matter 2014; 10(8):1199-213SM

Abstract

A series of novel aliphatic polyesters with azido functional groups were synthesized via the direct lipase-catalyzed polycondensation of dialkyl diester, diol and 2-azido-1,3-propanediol (azido glycerol) using immobilized lipase B from Candida antarctica (CALB). The effects of polymerization conditions including reaction time, temperature, enzyme amount, substrates and monomer feed ratio on the molecular weights of the products were studied. The polyesters with pendant azido groups were characterized by (1)H NMR, (13)C NMR, 2D NMR, FTIR, GPC and DSC. Alkyne end-functionalized poly(ethylene glycol) containing a cleavable acetal group was then grafted onto the polyester backbone by copper-catalyzed azide-alkyne cycloaddition (CuAAC, click chemistry). Using fluorescence spectroscopy, dynamic light scattering (DLS) and transmission electron microscopy (TEM), these amphiphilic graft copolymers were found to readily self-assemble into nanosized micelles in aqueous solution with critical micelle concentrations between 0.70 and 1.97 mg L(-1), and micelle sizes from 20-70 nm. The degradation of these polymers under acidic conditions was investigated by GPC and (1)H NMR spectroscopy. Cell cytotoxicity tests indicated that the micelles had no apparent cytotoxicity to Bel-7402 cells, suggesting their potential as carriers for controlled drug delivery.

Authors+Show Affiliations

Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P. R. China. wnchem@scu.edu.cn xqyu@scu.edu.cn.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

24652240

Citation

Wu, Wan-Xia, et al. "Lipase-catalyzed Synthesis of Azido-functionalized Aliphatic Polyesters Towards Acid-degradable Amphiphilic Graft Copolymers." Soft Matter, vol. 10, no. 8, 2014, pp. 1199-213.
Wu WX, Wang N, Liu BY, et al. Lipase-catalyzed synthesis of azido-functionalized aliphatic polyesters towards acid-degradable amphiphilic graft copolymers. Soft Matter. 2014;10(8):1199-213.
Wu, W. X., Wang, N., Liu, B. Y., Deng, Q. F., & Yu, X. Q. (2014). Lipase-catalyzed synthesis of azido-functionalized aliphatic polyesters towards acid-degradable amphiphilic graft copolymers. Soft Matter, 10(8), pp. 1199-213. doi:10.1039/c3sm52496e.
Wu WX, et al. Lipase-catalyzed Synthesis of Azido-functionalized Aliphatic Polyesters Towards Acid-degradable Amphiphilic Graft Copolymers. Soft Matter. 2014 Feb 28;10(8):1199-213. PubMed PMID: 24652240.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Lipase-catalyzed synthesis of azido-functionalized aliphatic polyesters towards acid-degradable amphiphilic graft copolymers. AU - Wu,Wan-Xia, AU - Wang,Na, AU - Liu,Bei-Yu, AU - Deng,Qing-Feng, AU - Yu,Xiao-Qi, PY - 2014/3/22/entrez PY - 2014/3/22/pubmed PY - 2014/11/19/medline SP - 1199 EP - 213 JF - Soft matter JO - Soft Matter VL - 10 IS - 8 N2 - A series of novel aliphatic polyesters with azido functional groups were synthesized via the direct lipase-catalyzed polycondensation of dialkyl diester, diol and 2-azido-1,3-propanediol (azido glycerol) using immobilized lipase B from Candida antarctica (CALB). The effects of polymerization conditions including reaction time, temperature, enzyme amount, substrates and monomer feed ratio on the molecular weights of the products were studied. The polyesters with pendant azido groups were characterized by (1)H NMR, (13)C NMR, 2D NMR, FTIR, GPC and DSC. Alkyne end-functionalized poly(ethylene glycol) containing a cleavable acetal group was then grafted onto the polyester backbone by copper-catalyzed azide-alkyne cycloaddition (CuAAC, click chemistry). Using fluorescence spectroscopy, dynamic light scattering (DLS) and transmission electron microscopy (TEM), these amphiphilic graft copolymers were found to readily self-assemble into nanosized micelles in aqueous solution with critical micelle concentrations between 0.70 and 1.97 mg L(-1), and micelle sizes from 20-70 nm. The degradation of these polymers under acidic conditions was investigated by GPC and (1)H NMR spectroscopy. Cell cytotoxicity tests indicated that the micelles had no apparent cytotoxicity to Bel-7402 cells, suggesting their potential as carriers for controlled drug delivery. SN - 1744-6848 UR - https://www.unboundmedicine.com/medline/citation/24652240/Lipase_catalyzed_synthesis_of_azido_functionalized_aliphatic_polyesters_towards_acid_degradable_amphiphilic_graft_copolymers_ L2 - https://doi.org/10.1039/c3sm52496e DB - PRIME DP - Unbound Medicine ER -