Preparation of methoxy poly (ethyleneglycol)-b-poly (ε-caprolactone-co-L-lactide) and characterization as biodegradable micelles

Kwon, Doo Yeon; Tai, Guo Zhe; Park, Ji Hoon; Lee, Bo Keun; Lee, Jae Hyeok; Kim, Jae Ho; Lee, Kyu Wan; Lee, Bong; Jang, Ju Woong; Kim, Moon Suk

doi:10.1007/s10965-014-0474-8

Cited by 4 publications

(4 citation statements)

References 26 publications

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“…These stiffer cores provided stability of polyplexes in physiological fluids and degradable backbone of nanoparticles, but the compact cores lead to a slow degradation rate in cells [30,31]. It has been confirmed that copolymerizing CL and DLLA in various ratio could adjust the stiffness and degradation rate of implant in tissue engineering [32] as well as the drug release from drug-loaded NPs with PCL/ PDLLA hybrid cores [33]. However, whether this structurefunction relationship could be applied in siRNA delivery still remained unclear.…”

Section: Introductionmentioning

confidence: 91%

“…S3. Although PECLD-30 and PECLD-70 had similar chemical constitution, PECLD-70 had a softer core according to DSC results, which may facilitate diffusion of water molecule and proton into the polyester core, and improved its degradation [32]. Therefore, combining proton sponge effect provided by PDMAEMA segments and increase in colloidal osmotic pressure in the endosomal vesicles after rapid degradation of polyester core [45,46], PECLD-70 showed an enhanced capability in endosomal escape and siRNA release compared to PECD and PECLD-30 NPs.…”

Section: Intracellular Release Of Sirnamentioning

confidence: 99%

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Effects of hydrophobic core components in amphiphilic PDMAEMA nanoparticles on siRNA delivery

Han

Cheng

et al. 2015

Biomaterials

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Section: Introductionmentioning

confidence: 91%

Section: Intracellular Release Of Sirnamentioning

confidence: 99%

Effects of hydrophobic core components in amphiphilic PDMAEMA nanoparticles on siRNA delivery

Han

Cheng

et al. 2015

Biomaterials

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“…Thus, tailoring the PLLA into the PCL segment can change the melting points of PLC. Consistent with this idea, we previously found that incorporation of the PLLA into the PCL segment decreased melting points by decreasing crystalline aggregation of the PCL segment interrupted by PLLA [19][20][21][22][23][24].…”

Section: Introductionmentioning

confidence: 53%

Effect of Drug Carrier Melting Points on Drug Release of Dexamethasone-Loaded Microspheres

Park

Kwon

Heo

et al. 2017

Tissue Eng Regen Med

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Here, we examined the effect of melting point of drug carriers on drug release of dexamethasone (Dex)-loaded microspheres. We prepared poly(L-lactide-ran-e-caprolactone) (PLC) copolymers with varying compositions of poly(ecaprolactone) (PCL) and poly(L-lactide) (PLLA). As the PLLA content increased, the melting points of PLC copolymers decreased from 61 to 43°C. PLC copolymers in vials solubilized at 40-50°C according to the incorporation of PLLA into the PCL segment. Dexamethasone (Dex)-loaded PLC (MC x L y) microspheres were prepared by the oil-in-water (O/W) solvent evaporation/extraction method. The preparation yields were above 70%, and the mean particle size ranged from 30 to 90 lm. The MC x L y microspheres also showed controllable melting points in the range of 40-60°C. Dex-loaded MC x L y microspheres showed similar in vitro and in vivo sustained release patterns after the initial burst of Dex. The in vitro and in vivo order of the Dex release was MC 80 L 20 [ MC 90 L 10 [ MC 95 L 5 , which agreed well with the melting point order of the drug carrier. Using in vivo fluorescence imaging of fluorescein (FI)-loaded microspheres implanted in animals, we confirmed the sustained release of FI over an extended period. In vivo inflammation associated with the PLC microsphere implants was less pronounced than that associated with Poly(lactide-co-glycolide) (PLGA). In conclusion, we successfully demonstrated that it is possible to control Dex release using Dex-loaded MC x L y microspheres with different melting points.

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“…Some biodegradable polyesters, such as polyhydroxyalkanoates (e.g., poly 3-hydroxybutyrate (P3HB) and poly 3-hydroxybutyrateco-3-hydroxyvalerate (P3HB3HV)), are produced via the biological route [11][12][13], more expensive and less controlled than a conventional chemical polymerisation. The most common chemical strategy to synthesise biodegradable polyesters is the Ring-Opening Polymerisation (ROP) starting from cyclic esters (lactones); ROP is a well-consolidated reaction scheme for the polymerization of lactide [14][15][16][17][18] and glycolide [19] (6-membered dimers of lactic and glycolic acids respectively), ε-caprolactone (7-membered ring [20][21][22][23]), δ-valerolactone (6-membered [24]) and β-butyrolactone (4-membered [25][26][27][28]). …”

Section: Introductionmentioning

confidence: 99%

Chemical synthesis of a biodegradable PEGylated copolymer from ε-caprolactone and γ-valerolactone: evaluation of reaction and functional properties

et al. 2015

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This paper reports the chemical synthesis of methoxy poly(ethyleneglycol)-block-poly(ε-caprolactone-co-4-hydroxyvalerate) from ε-caprolactone and γ-valerolactone, a five-membered ring rarely used in chemical synthesis due to its low reactivity. This procedure enabled production of copolymers with controlled ratios of repeating units and molecular weights, as demonstrated by GPC, FT-IR and NMR characterization. Copolymer degradation rate was found to depend on macromolecular composition, and finely tuneable in a wide range of values. Similarly, hydrophilicity was dependent on γ-valerolactone content, and could be accurately controlled by varying the composition of the reaction feed. Importantly, this copolymer showed lower levels of acidic degradation products than other biodegradable polymers, thus resulting in improved biocompatibility. These encouraging results demonstrate the feasibility of the chemical synthesis of a novel and versatile material with interesting properties that fill a gap in the range of commercially available biodegradable polymers.

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Preparation of methoxy poly (ethyleneglycol)-b-poly (ε-caprolactone-co-L-lactide) and characterization as biodegradable micelles

Cited by 4 publications

References 26 publications

Effects of hydrophobic core components in amphiphilic PDMAEMA nanoparticles on siRNA delivery

Effects of hydrophobic core components in amphiphilic PDMAEMA nanoparticles on siRNA delivery

Effect of Drug Carrier Melting Points on Drug Release of Dexamethasone-Loaded Microspheres

Chemical synthesis of a biodegradable PEGylated copolymer from ε-caprolactone and γ-valerolactone: evaluation of reaction and functional properties

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