Thermal properties and physicochemical behavior in aqueous solution of pyrene-labeled poly(ethylene glycol)-polylactide conjugate

Wei-Lin Chen,1,2 Yun-Fen Peng,1,3 Sheng-Kuo Chiang,1 Ming-Hsi Huang1–3 1National Institute of Infectious Diseases and Vaccinology, National Health Research Institutes, Miaoli, Taiwan; 2Graduate Institute of Life Sciences, National Defense Medical Center, Taipei, Taiwan; 3PhD Program in T...

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Autores principales:	Chen WL, Peng YF, Chiang SK, Huang MH
Formato:	article
Lenguaje:	EN
Publicado:	Dove Medical Press 2015
Materias:	Medicine (General) R5-920
Acceso en línea:	https://doaj.org/article/04ed539c55664251b9f24a36dab8724a
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spelling	oai:doaj.org-article:04ed539c55664251b9f24a36dab8724a2021-12-02T07:43:42ZThermal properties and physicochemical behavior in aqueous solution of pyrene-labeled poly(ethylene glycol)-polylactide conjugate1178-2013https://doaj.org/article/04ed539c55664251b9f24a36dab8724a2015-04-01T00:00:00Zhttp://www.dovepress.com/thermal-properties-and-physicochemical-behavior-in-aqueous-solution-of-peer-reviewed-article-IJNhttps://doaj.org/toc/1178-2013 Wei-Lin Chen,1,2 Yun-Fen Peng,1,3 Sheng-Kuo Chiang,1 Ming-Hsi Huang1–3 1National Institute of Infectious Diseases and Vaccinology, National Health Research Institutes, Miaoli, Taiwan; 2Graduate Institute of Life Sciences, National Defense Medical Center, Taipei, Taiwan; 3PhD Program in Tissue Engineering and Regenerative Medicine, National Chung Hsing University, Taichung, Taiwan Abstract: A fluorescence-labeled bioresorbable polymer was prepared by a coupling reaction of poly(ethylene glycol)-polylactide (PEG-PLA) with carboxyl pyrene, using N,N’-diisopropylcarbodiimide/1-hydroxy-7-azabenzotriazole (DIC/HOAt) as a coupling agent and 4-dimethylaminopyridine (DMAP) as a catalyst. The obtained copolymer, termed PEG-PLA-pyrene, was characterized using various analytical techniques, such as gel permeation chromatography (GPC), matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS), proton nuclear magnetic resonance (1H-NMR), infrared spectroscopy (IR), differential scanning calorimetry (DSC), and thermogravimetric analysis (TGA), to identify the molecular structure and to monitor the thermal property changes before and after the reaction. The presence of a pyrene moiety at the end of polylactide (PLA) did not alter the crystallization ability of the poly(ethylene glycol) (PEG) blocks, indicating that the conjugate preserved the inherent thermal properties of PEG-PLA. However, the presence of PEG-PLA blocks strongly reduced the melting of pyrene, indicating that the thermal characteristics were sensitive to PEG-PLA incorporation. Regarding the physicochemical behavior in aqueous solution, a higher concentration of PEG-PLA-pyrene resulted in a higher ultraviolet-visible (UV-vis) absorbance and fluorescence emission intensity. This is of great interest for the use of this conjugate as a fluorescence probe to study the in vivo distribution as well as the internalization and intracellular localization of polymeric micelles. Keywords: bioresorbable polymer, fluorescence probe, pyrene, polymeric micelles, poly (ethylene glycol)-polylactide, PEG-PLAChen WLPeng YFChiang SKHuang MHDove Medical PressarticleMedicine (General)R5-920ENInternational Journal of Nanomedicine, Vol 2015, Iss default, Pp 2815-2822 (2015)
institution	DOAJ
collection	DOAJ
language	EN
topic	Medicine (General) R5-920
spellingShingle	Medicine (General) R5-920 Chen WL Peng YF Chiang SK Huang MH Thermal properties and physicochemical behavior in aqueous solution of pyrene-labeled poly(ethylene glycol)-polylactide conjugate
description	Wei-Lin Chen,1,2 Yun-Fen Peng,1,3 Sheng-Kuo Chiang,1 Ming-Hsi Huang1–3 1National Institute of Infectious Diseases and Vaccinology, National Health Research Institutes, Miaoli, Taiwan; 2Graduate Institute of Life Sciences, National Defense Medical Center, Taipei, Taiwan; 3PhD Program in Tissue Engineering and Regenerative Medicine, National Chung Hsing University, Taichung, Taiwan Abstract: A fluorescence-labeled bioresorbable polymer was prepared by a coupling reaction of poly(ethylene glycol)-polylactide (PEG-PLA) with carboxyl pyrene, using N,N’-diisopropylcarbodiimide/1-hydroxy-7-azabenzotriazole (DIC/HOAt) as a coupling agent and 4-dimethylaminopyridine (DMAP) as a catalyst. The obtained copolymer, termed PEG-PLA-pyrene, was characterized using various analytical techniques, such as gel permeation chromatography (GPC), matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS), proton nuclear magnetic resonance (1H-NMR), infrared spectroscopy (IR), differential scanning calorimetry (DSC), and thermogravimetric analysis (TGA), to identify the molecular structure and to monitor the thermal property changes before and after the reaction. The presence of a pyrene moiety at the end of polylactide (PLA) did not alter the crystallization ability of the poly(ethylene glycol) (PEG) blocks, indicating that the conjugate preserved the inherent thermal properties of PEG-PLA. However, the presence of PEG-PLA blocks strongly reduced the melting of pyrene, indicating that the thermal characteristics were sensitive to PEG-PLA incorporation. Regarding the physicochemical behavior in aqueous solution, a higher concentration of PEG-PLA-pyrene resulted in a higher ultraviolet-visible (UV-vis) absorbance and fluorescence emission intensity. This is of great interest for the use of this conjugate as a fluorescence probe to study the in vivo distribution as well as the internalization and intracellular localization of polymeric micelles. Keywords: bioresorbable polymer, fluorescence probe, pyrene, polymeric micelles, poly (ethylene glycol)-polylactide, PEG-PLA
format	article
author	Chen WL Peng YF Chiang SK Huang MH
author_facet	Chen WL Peng YF Chiang SK Huang MH
author_sort	Chen WL
title	Thermal properties and physicochemical behavior in aqueous solution of pyrene-labeled poly(ethylene glycol)-polylactide conjugate
title_short	Thermal properties and physicochemical behavior in aqueous solution of pyrene-labeled poly(ethylene glycol)-polylactide conjugate
title_full	Thermal properties and physicochemical behavior in aqueous solution of pyrene-labeled poly(ethylene glycol)-polylactide conjugate
title_fullStr	Thermal properties and physicochemical behavior in aqueous solution of pyrene-labeled poly(ethylene glycol)-polylactide conjugate
title_full_unstemmed	Thermal properties and physicochemical behavior in aqueous solution of pyrene-labeled poly(ethylene glycol)-polylactide conjugate
title_sort	thermal properties and physicochemical behavior in aqueous solution of pyrene-labeled poly(ethylene glycol)-polylactide conjugate
publisher	Dove Medical Press
publishDate	2015
url	https://doaj.org/article/04ed539c55664251b9f24a36dab8724a
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Thermal properties and physicochemical behavior in aqueous solution of pyrene-labeled poly(ethylene glycol)-polylactide conjugate

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