Synthesis and Micellization of Star‐Shaped Poly(ethylene glycol)‐<i>block</i>‐Poly(<i>ε</i>‐caprolactone)

Kim, Keon Hyeong; Cui, Guo Hua; Lim, Hyung Bin; Huh, June; Ahn, Cheol Hee; Jo, Won Ho

doi:10.1002/macp.200400084

Cited by 71 publications

(55 citation statements)

References 21 publications

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“…20 The mean hydrodynamic diameter of copolymer micelles was less than 50 nm, s-(PCL 5.1 -PEO 2.0 ) 4 micelles being larger than l-PCL 6.7 -(PEO 2.0 ) 2 micelles, while significant differences were not observed for polydispersity index. Micelle size for s-(PCL 5.1 -PEO 2.0 ) 4 was lower than that reported by Kim et al, 18 probably because of a different preparation procedure (nanoprecipitation vs. dialysis). The greater size of s-(PCL 5.1 -PEO 2.0 ) 4 micelles when compared with that of l-PCL 6.7 -(PEO) 2.0 micelles was interpreted on the basis of the schematic model proposed in Figure 3(C) and related to the effective length of PCL segments (L c ) upon self-assembly which is higher for s-(PCL 5.1 -PEO 2.0 ) 4 .…”

Section: Micelle Preparation and Characterizationcontrasting

confidence: 70%

Micelles based on amphiphilic PCL‐PEO triblock and star‐shaped diblock copolymers: Potential in drug delivery applications

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et al. 2008

J Biomedical Materials Res

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In this work, the potential in drug nanodelivery of micelles made from poly(epsilon-caprolactone) (PCL) and poly (ethyleneoxide) (PEO) copolymers with triblock and star-diblock architectures was explored. Linear and 4-arm star-shaped PCL macromers with two or four --OH end groups were prepared by ring-opening polymerization of CL and condensed with alpha-methoxy-omega-carboxy-PEO. The resulting amphiphilic copolymers were characterized by (1)H NMR, size exclusion chromatography, and differential scanning calorimetry. Separate PCL and PEO crystalline phases were observed for both copolymers. Copolymers self-assembled in water giving critical association concentrations in the range 0.010-0.023 mg/mL. Micelles with a size of 32-45 nm were prepared by dialysis and characterized for hydrodynamic diameter and surface charge. Their potential as nanocarriers in drug delivery applications was evaluated too. Micelles were nontoxic to both Red blood cells and HeLa cells. Complement activation experiments indicated that micelles can escape the reticuloendothelial system once intravenously injected. Finally, a different uptake on HeLa cells was found for micelles obtained from triblock and star-shaped copolymers.

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Section: Micelle Preparation and Characterizationcontrasting

confidence: 70%

Micelles based on amphiphilic PCL‐PEO triblock and star‐shaped diblock copolymers: Potential in drug delivery applications

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Ostacolo

Nese

et al. 2008

J Biomedical Materials Res

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“…Star-shaped block copolymers with a core consisting of hydrophobic inner branches and multiple hydrophilic poly(ethylene glycol) (PEG) tails have been synthesized in the range of 3 to 32 by Wang et al [7,8], Zheng et al [9] and some other groups [10][11][12][13][14][15][16]. The unimers with arm numbers of 16 or 32 have shown the high stability, drug delivery efficacy and physicochemical properties compared to unimers with a smaller arm number.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Biodegradable Amphiphilic Star and Y-Shaped Block Copolymers as Potential Carriers for Vinorelbine

et al. 2014

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Two amphiphilic block copolymers using hydrophobic poly(ε-caprolactone) (PCL) and hydrophilic poly(ethylene glycol) (PEG) were successfully synthesized. One of them is an (A-b-B) 4 type star polymer [(PCL-b-PEG) 4 ] and the other one is a Y-shaped PEG-(PCL) 2 . A star-shaped polymer (PCL-b-PEG) 4 was prepared by ring-opening polymerization (ROP) of ε-caprolactone continued by click reaction of (PCL-azide) 4 and PEG-alkyne. The synthesis of Y-shaped PEG-(PCL) 2 block copolymer was carried out via Diels-Alder click reaction of a furan protected maleimide end-functionalized PEG (PEG-MI) with an anthracene end-functionalized PCL following the ROP of ε-caprolactone. The characterization of micelles is carried out using both materials in aqueous media as drug delivery vehicles, which showed satisfying results and enhanced the cytotoxic effect of the OPEN ACCESSPolymers 2014, 6 215 anti-cancer drug vinorelbine (VLB). However, micelles consisted of Y-shaped unimers were found to be more convenient for delivery of hydrophobic drugs such as VLB because they formed in lower concentration, carrying a higher amount of drugs and owing a monomodal distribution. We concluded that the free tails of hydrophobic chains in Y-shaped block copolymer facilitate the assembly of amphiphilic material in water to form micelles.

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“…One paper (13) described the synthesis of a 4 arm star block copolymer of PCL and PEG using chemistry similar to that reported in this manuscript. Another report (14) described the preparation of a 4 arm star PCL-b-PEG polymer using a diethyl zinc catalyst.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Star Poly(ε-caprolactone)-b-Poly(ethylene glycol) and Poly(l-lactide)-b-Poly(ethylene glycol) Copolymers: Evaluation as Drug Delivery Carriers

et al. 2008

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Two types of 32 arm star polymers incorporating amphiphilic block copolymer arms have been synthesized and characterized. The first type, stPCL-PEG 32 , is composed of a polyamidoamine (PAMAM) dendrimer as the core with radiating arms having poly(ε-caprolactone) (PCL) as an inner lipophilic block in the arm and poly(ethylene glycol) (PEG) as an outer hydrophilic block. The second type, stPLA-PEG 32 , is similar but with poly(L-lactide) (PLA) as the inner lipophilic block. Characterization with SEC, 1 H NMR, FTIR, and DSC confirmed the structure of the polymers. Micelle formation by both star copolymers was studied by fluorescence spectroscopy. The stPCL-PEG 32 polymer exhibited unimolecular micelle behavior. It was capable of solubilizing hydrophobic molecules, such as pyrene, in aqueous solution, while not displaying a critical micelle concentration. In contrast, the association behavior of stPLA-PEG 32 in aqueous solution was characterized by an apparent critical micelle concentration of ca. 0.01 mg/mL. The hydrophobic anticancer drug etoposide can be encapsulated in the micelles formed from both polymers. Overall, the stPCL-PEG 32 polymer exhibited a higher etoposide loading capacity (up to 7.8 w/w % versus 4.3 w/w % for stPLA-PEG 32 ) as well as facile release kinetics and is more suitable as a potential drug delivery carrier.

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Synthesis and Micellization of Star‐Shaped Poly(ethylene glycol)‐block‐Poly(ε‐caprolactone)

Cited by 71 publications

References 21 publications

Micelles based on amphiphilic PCL‐PEO triblock and star‐shaped diblock copolymers: Potential in drug delivery applications

Micelles based on amphiphilic PCL‐PEO triblock and star‐shaped diblock copolymers: Potential in drug delivery applications

Synthesis and Characterization of Biodegradable Amphiphilic Star and Y-Shaped Block Copolymers as Potential Carriers for Vinorelbine

Synthesis and Characterization of Star Poly(ε-caprolactone)-b-Poly(ethylene glycol) and Poly(l-lactide)-b-Poly(ethylene glycol) Copolymers: Evaluation as Drug Delivery Carriers

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