Novel poly(ɛ-caprolactone)s bearing amino groups: Synthesis, characterization and biotinylation

Yan, Jinliang; Zhang, Yi; Xiao, Yan; Zhang, Yan; Lang, Meidong

doi:10.1016/j.reactfunctpolym.2010.03.008

Cited by 67 publications

(39 citation statements)

References 38 publications

(47 reference statements)

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“…PCL bearing NH 2 was synthesized as described in Ref. [29], PCL bearing CH 3 was prepared as in Ref. [30], PCL bearing COOH was prepared as reported in Refs.…”

Section: Synthesis Of Pcl Derivativesmentioning

confidence: 99%

“…This would serve as a realistic platform to gain further understanding of the effects of biomaterial surface chemistry on stem cells. The polymer series was synthesized via ring-opening copolymerization as described in our previous work [29,30,33], giving different pendant groups on the backbone of PCL chain (Fig. 2, left panel).…”

Section: Preparation Of Pcl Films Bearing Small Functional Groupsmentioning

confidence: 99%

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Pendant small functional groups on poly(ϵ-caprolactone) substrate modulate adhesion, proliferation and differentiation of human mesenchymal stem cells

Chen

Zhang

Zhou

et al. 2015

Colloids and Surfaces B: Biointerfaces

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“…PCL bearing NH 2 was synthesized as described in Ref. [29], PCL bearing CH 3 was prepared as in Ref. [30], PCL bearing COOH was prepared as reported in Refs.…”

Section: Synthesis Of Pcl Derivativesmentioning

confidence: 99%

Section: Preparation Of Pcl Films Bearing Small Functional Groupsmentioning

confidence: 99%

Pendant small functional groups on poly(ϵ-caprolactone) substrate modulate adhesion, proliferation and differentiation of human mesenchymal stem cells

Chen

Zhang

Zhou

et al. 2015

Colloids and Surfaces B: Biointerfaces

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“…23 As a continuing endeavor in developing micelles for drug delivery, the objective of the present study was to design and synthesize a novel family of amphiphilic copolymers based on PEG-b-PCL to improve both drug incorporation and release. Our strategy involved a ring-opening copolymerization of ε-caprolactone (CL) with a newly developed monomer (γ-(carbamic acid benzyl ester)-ε-caprolactone (CABCL)), 24 using mPEG as macroinitiator to prepare mPEGb-PCL diblock copolymers bearing carbamic acid benzyl ester (CAB) group on the backbone of PCL block ( Figure 1A). We hypothesized that the introduction of CAB groups was able to tune the properties of PEG-b-PCL micelles (mostly, the crystallinity and drugÀpolymer compatibility of the core-forming block) to achieve greater performance of DOX-loaded micelles.…”

Section: ' Introductionmentioning

confidence: 99%

Fine Tuning Micellar Core-Forming Block of Poly(ethylene glycol)-block-poly(ε-caprolactone) Amphiphilic Copolymers Based on Chemical Modification for the Solubilization and Delivery of Doxorubicin

et al. 2011

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This study aimed to optimize poly(ethylene glycol)-b-poly(ε-caprolactone) (PEG-b-PCL)-based amphiphilic block copolymers for achieving a better micellar drug delivery system (DDS) with improved solubilization and delivery of doxorubicin (DOX). First, the Flory-Huggins interaction parameters between DOX and the core-forming segments [i.e., poly(ε-caprolactone) (PCL) and poly[(ε-caprolactone-co-γ-(carbamic acid benzyl ester)-ε-caprolactone] (P(CL-co-CABCL))] was calculated to assess the drug-polymer compatibility. The results indicated a better compatibility between DOX and P(CL-co-CABCL) than that between DOX and PCL, motivating the synthesis of monomethoxy-poly(ethylene glycol)-b-poly[(ε-caprolactone-co-γ-(carbamic acid benzyl ester)-ε-caprolactone] (mPEG-b-P(CL-co-CABCL)) block copolymer. Second, two novel block copolymers of mPEG-b-P(CL-co-CABCL) with different compositions were prepared via ring-opening polymerization of CL and CABCL using mPEG as a macroinitiator and characterized by (1)H NMR, FT-IR, GPC, WAXD, and DSC techniques. It was found that the introduction of CABCL decreased the crystallinity of mPEG-b-PCL copolymer. Micellar formation of the copolymers in aqueous solution was investigated with fluorescence spectroscopy, DLS and TEM. mPEG-b-P(CL-co-CABCL) copolymers had a lower critical micelle concentration (CMC) than mPEG-b-PCL and subsequently led to an improved stability of prepared micelles. Furthermore, both higher loading capacity and slower in vitro release of DOX were observed for micelles of copolymers with increased content of CABCL, attributed to both improved drug-core compatibility and favorable amorphous core structure. Meanwhile, DOX-loaded micelles facilitated better uptake of DOX by HepG2 cells and were mainly retained in the cytosol, whereas free DOX accumulated more in the nuclei. However, possibly because of the slower intracellular release of DOX, DOX-loaded micelles were less potent in inhibiting cell proliferation than free DOX in vitro. Taken together, the introduction of CABCL in the core-forming block of mPEG-b-PCL resulted in micelles with superior properties, which hold great promise for drug delivery applications.

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“…[18] 的前期研究中, 合成了主链带有羧基的 PEG-PCL 聚合物, 并探索了羧基官能团对于聚合物胶束形成机理和 pH 敏感性的影响. 我们课题组 [19,20] 也合成了疏水主链 PCL 上带有氨基甲酸苄酯 (CAB)官能团的聚合物 mPEG-b-P(CABCL-co-CL), 同样发现此保护基的引入能够降低聚己内酯的结晶性和疏水性, 而且经过一步脱保护反应后得到了氨基修饰的聚己内酯能够进一步进行化学修饰. 本文采用 6-乙酸苄酯己内酯(BCL)作为官能化己内酯单体 [21] , 以 Pluronic F127 为大分子引发剂, 合成…”

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“…BCL 单体的配位能力, 从而导致在共聚反应中 BCL 的单体反应活性要低于 CL [19] . 另外, 通过 GPC 测得的分子量要低于 1 H NMR 计算得到的分子量, 这是由于 GPC 是以单分散性聚苯乙烯作为基准测定分子量, 而聚合物 Pluronic-b-P(CL-co-BCL)作为一种聚酯, 其流体力学体积和聚苯乙烯是有明显差别的 [22] .…”

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Synthesis and Properties of Thermo-sensitive Amphiphilic Pluronic-b-poly((ε-caprolactone)-co-(6-(benzyl-oxycarbonylmethyl)-ε-caprolactone))

杜征臻¹,

Zhang²,

张琰³

et al. 2014

Acta Chim. Sinica

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In this paper, a series of amphiphilic block copolymers Pluronic-b-poly(ε-caprolactone-co-benzyl-oxycarbonylmethyl-ε-caprolactone) (Pluronic-b-P(CL-co-BCL)) were synthesized successfully via ring-opening polymerization (ROP) of ε-caprolactone (CL) and 6-(benzyl-oxycarbonylmethyl)-ε-caprolactone (BCL) using stannous octoate as the catalyst (weight ratio: 0.5‰) and PEO 99 -b-PPO 69 -b-PEO 99 (Pluronic F127) as macroinitiator.1 H NMR, GPC and FT-IR were employed to determine the structure, composition, molecular weight and molecular weight distribution. The result of 1 H NMR showed the content of BCL in the copolymers was less than the theoretical value, which may be attributed to the low reactivity of BCL due to the steric hindrance of Bn substituent on the δ position of CL. The number-average molecular weight by GPC was different from the value calculated by 1 H NMR, it may be attributed to the hydrodynamic volume of the copolymers being different from that of the poly(styrene) as the GPC calibration in THF. The thermal properties of the copolymers were evaluated by TGA, DSC and XRD. The results indicated that the stability and the crystallinity of the copolymers could be adjusted by the content of the BCL. Due to the BCL units in the copolymers reduced the regularity of the PCL chain and intensively disrupted its crystallinity and the steric hindrance effect of BCL trammeled the movement of the PCL chain, the melting point (T m ) of CL segment in copolymer shifted down and the glass transition temperature (T g ) of copolymer increased with the increase of the content of BCL respectively. Emulsion/solvent evaporation technique was employed to prepare the polymeric micelle solution. The formation, size and morphologies of the micelles in aqueous solution were studied by fluorescence spectroscopy, TEM and DLS, the results demonstrated that the micelles were spherical spheres with narrow distribution, the copolymer had low critical micelles concentration (CMC) and depended on the content of BCL in the copolymer. Moreover,

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Novel poly(ɛ-caprolactone)s bearing amino groups: Synthesis, characterization and biotinylation

Cited by 67 publications

References 38 publications

Pendant small functional groups on poly(ϵ-caprolactone) substrate modulate adhesion, proliferation and differentiation of human mesenchymal stem cells

Pendant small functional groups on poly(ϵ-caprolactone) substrate modulate adhesion, proliferation and differentiation of human mesenchymal stem cells

Fine Tuning Micellar Core-Forming Block of Poly(ethylene glycol)-block-poly(ε-caprolactone) Amphiphilic Copolymers Based on Chemical Modification for the Solubilization and Delivery of Doxorubicin

Synthesis and Properties of Thermo-sensitive Amphiphilic Pluronic-b-poly((ε-caprolactone)-co-(6-(benzyl-oxycarbonylmethyl)-ε-caprolactone))

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