Fabrication of micelles from poly(butylene succinate) and poly(2‐methacryloyloxyethyl phosphorylcholine) copolymers as a potential drug carrier

Zhang, Yucheng; Yi, Meijun; Bao, Yi Wang; Zhang, Shiping

doi:10.1002/pi.5482

Cited by 10 publications

(10 citation statements)

References 44 publications

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“…P(MPC- co -MaPCL) and FA-P(MPC- co -MaPCL) micelles were prepared by a combination of solvent evaporation and dialysis methods according to our previous reports. ,, Briefly, 10 mg of copolymer P(MPC- co -MaPCL) or FA-P(MPC- co -MaPCL) was dissolved fully in 3 mL of mixed solution of CHCl 3 and CH 3 OH (v:v = 3:1) and the solution was added dropwise into 10 mL of deionized water under vigorous stirring. The resulting suspension was stirred overnight and dialyzed for 12 h to form micelles.…”

Section: Methodsmentioning

confidence: 99%

Folate-Conjugated Cell Membrane Mimetic Polymer Micelles for Tumor-Cell-Targeted Delivery of Doxorubicin

Zhang

et al. 2018

Langmuir

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Tumor-targeting nano-drug-delivery systems hold great potential to improve the therapeutic efficacy and alleviate the side effects of cancer treatments. Herein, folic acid (FA)-decorated amphiphilic copolymer of FA-P(MPC-co-MaPCL) (MPC: 2-methacryloxoethyl phosphorylcholine, MaPCL: poly(ε-caprolactone) macromonomer) is synthesized and its micelles are fabricated for doxorubicin (DOX) delivery. And non-FA-decorated P(MPC-co-MaPCL) micelles are used as the control. Dynamic light scattering and scanning electron microscopy measurements reveal that FA-P(MPC-co-MaPCL) and P(MPC-co-MaPCL) micelles are spherical with average diameters of 140 and 90 nm, respectively. The evaluation in vitro demonstrates that the blank micelles are nontoxic, while DOX-loaded FA-P(MPC-co-MaPCL) micelles show significant cytotoxicity to HeLa cells and slight cytotoxicity to L929 cells. Moreover, the cellular uptake of DOX-loaded FA-P(MPC-co-MaPCL) micelles in HeLa cells are 4.3-fold and 1.7-fold higher than that of DOX-loaded P(MPC-co-MaPCL) micelles and free DOX after 6 h of incubation, respectively. These results indicate the great potential of this system in anticancer target drug-delivery applications.

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Section: Methodsmentioning

confidence: 99%

Folate-Conjugated Cell Membrane Mimetic Polymer Micelles for Tumor-Cell-Targeted Delivery of Doxorubicin

Zhang

et al. 2018

Langmuir

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“…These methods required the use of complicated multi‐step synthesis, long reaction times and toxic metal catalysts to some extent. Another method for the improvement of PBS is the introduction of functional hydrophilic polymers . Recently, we prepared a series copolymers of poly(2‐methacryloyloxyethyl phosphorylcholine)‐ block ‐PBS‐ block ‐poly(2‐methacryloyloxyethyl phosphorylcholine) (PMPC‐ b ‐PBS‐ b ‐PMPC) by atom transfer radical polymerization .…”

Section: Introductionmentioning

confidence: 99%

“…Another method for the improvement of PBS is the introduction of functional hydrophilic polymers . Recently, we prepared a series copolymers of poly(2‐methacryloyloxyethyl phosphorylcholine)‐ block ‐PBS‐ block ‐poly(2‐methacryloyloxyethyl phosphorylcholine) (PMPC‐ b ‐PBS‐ b ‐PMPC) by atom transfer radical polymerization . The results showed that these copolymers could form nano‐sized micelles in water with phosphorylcholine shell and PBS core structure.…”

Section: Introductionmentioning

confidence: 99%

“…However, no work has been reported about PDMAEMA‐modified PBS to the best of our knowledge, although PBS is a degradable and biocompatible polyester. Also, among functional groups or polymers, only uncharged hydroxyl groups, PMPC polymer and negatively charged sulfonate groups have been used to modify PBS . No positively charged group or polymer has been used to modify PBS.…”

Section: Introductionmentioning

confidence: 99%

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Preparation of poly(butylene succinate)‐poly[2‐(dimethylamino)ethyl methacrylate] copolymers and their applications as carriers for drug delivery

Zhao

Guo

et al. 2018

Polymer International

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Copolymers of poly[2‐(dimethylamino)ethyl methacrylate]–poly(butylene succinate)–poly[2‐(dimethylamino)ethyl methacrylate] (PDMAEMA–PBS–PDMAEMA, PDBD) were synthesized through a chain‐extension reaction. The thermal properties characterized using differential scanning calorimetry showed that the introduction of PDMAEMA chains slightly decreased the melting temperature of PBS. The water contact angle of PDBD copolymer films with media of various pH decreased with a decrease of pH. This should be ascribed to the conformational transition of PDMAEMA blocks from a compact coil to an expanding shape in accordance with the variation of the pH of the surroundings. The results of dynamic light scattering and scanning electron microscopy revealed that PDBD copolymers could form spherical micelles with small particle size and narrow particle size distribution. Furthermore, drug loading (loading content, ca 10%; encapsulation efficiency, ca 60%) and release experiments were conducted using doxorubicin as a hydrophobic model drug. The results of release experiments of copolymer nanomicelles showed that these micelles had pH‐responsive properties. © 2018 Society of Chemical Industry

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“…The copolymer of PCL- b -PMPC was synthesized in three steps. First, hydroxyl-terminated poly(ε-caprolactone), PCL-OH, was synthesized by ring-opening polymerization (ROP) with benzyl alcohol as the initiator and Sn(Oct) 2 as the catalyst. , Then bromoisobutyryl-terminated poly(ε-caprolactone), PCL- i BuBr, was synthesized through a reaction of PCL-OH and 2-bromoisobutyryl bromide using TEA as the catalyst in a solvent of CH 2 Cl 2 . , Afterward, copolymer PCL- b -PMPC was synthesized via ATRP in the presence of CuBr and bpy, using THF and CH 3 OH as a mixed solvent at 50 °C for 36 h. − PCL- b -PMPC was purified by dialysis using a dialysis bag with MWCO-3500 Da for 3 days in water. Finally, PCL- b -PMPC was collected after lyophilization (yield 84%) and then characterized by 1 H NMR spectroscopy.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Characterization of Folate-Modified Cell Membrane Mimetic Copolymer Micelles for Effective Tumor Cell Internalization

Zhang

et al. 2021

ACS Appl. Bio Mater.

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The inefficient targeting and phagocytic clearance of nanodrug delivery systems are two major obstacles in cancer therapy. Here, inspired by the special properties of zwitterionic polymers and folic acid (FA), a partly biodegradable copolymer of FA-modified poly(ε-caprolactone) block poly(2-methacryloxoethyl phosphorylcholine), PCL-b-PMPC-FA, was synthesized via atom transfer radical polymerization (ATRP) and click reaction. Non-FA-modified copolymer PCL-b-PMPC was also synthesized as a control. The hydrodynamic diameter of the PCL-b-PMPC-FA micelles is 158 nm (PDI 0.261), slightly larger than that of the PCL-b-PMPC micelles (139 nm, PDI 0.242). The drug doxorubicin (DOX) could be entrapped in the micelles, and as the pH decreased from 7.4 to 5.0, DOX release (in vitro) was accelerated. The 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay indicated that both the PCL-b-PMPC and the PCL-b-PMPC-FA micelles showed low toxicity to L929, HeLa, and MCF-7 cells. In addition, the DOX-loaded micelles, PCL-b-PMPC/DOX and PCL-b-PMPC-FA/DOX micelles, exhibited low toxicity to L929 cells but high toxicity to HeLa and MCF-7 cells, especially the PCL-b-PMPC-FA/DOX micelles. HeLa and MCF-7 cell uptakes of the PCL-b-PMPC-FA/DOX micelles were 4.8 and 4.5 times higher than that of the PCL-b-PMPC/DOX micelles, respectively. Therefore, PCL-b-PMPC-FA micelles have great potential for developing drug delivery systems with extended circulation times and tumor-targeting properties.

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Fabrication of micelles from poly(butylene succinate) and poly(2‐methacryloyloxyethyl phosphorylcholine) copolymers as a potential drug carrier

Cited by 10 publications

References 44 publications

Folate-Conjugated Cell Membrane Mimetic Polymer Micelles for Tumor-Cell-Targeted Delivery of Doxorubicin

Folate-Conjugated Cell Membrane Mimetic Polymer Micelles for Tumor-Cell-Targeted Delivery of Doxorubicin

Preparation of poly(butylene succinate)‐poly[2‐(dimethylamino)ethyl methacrylate] copolymers and their applications as carriers for drug delivery

Synthesis and Characterization of Folate-Modified Cell Membrane Mimetic Copolymer Micelles for Effective Tumor Cell Internalization

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