Synthesis and characterization of a functionalized amphiphilic diblock copolymer: MePEG-b-poly(DL-lactide-co-RS-β-malic acid)

Wang, Liang; Jia, Xiaohua; Liu, Xiaohang; Yuan, Zhi; Huang, Jiaxian

doi:10.1007/s00396-006-1560-1

Cited by 10 publications

(4 citation statements)

References 43 publications

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“…Finally, with the aim to functionalize the PLA block of PLA-b-PEG, Yuan and co-workers developed copolymers with PMLABe, PLA and PEG segments. 161 The simultaneous bulk ring-opening copolymerization of D,L-lactide (LA) and rac-MLABe was catalyzed by Sn(Oct) 2 in the presence of Me-PEG-OH as the initiator, thereby affording Me-PEG-b-P(LA-co-MLABe). The inuence of various parameters (reaction temperature, reaction time, monomer and initial initiator loading) was studied.…”

Section: Copolymerization Of Mlabe With Lactidesmentioning

confidence: 99%

Benzyl β-malolactonate polymers: a long story with recent advances

Jaffredo

Guillaume

2014

Polym. Chem.

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International audiencePoly (-benzyl malolactonate) (PMLABe) is an aliphatic renewable, biocompatible, biodegradable, hydrophobic polyester of the poly(hydroxyalkanoate) (PHA) family. Along with the hydrophilic parent poly(-malic acid) (PMLA), PMLABe and PMLA have been studied as materials for biomedical applications. Herein, advances on the synthesis of benzyl -malolactonate (MLABe) and the related alkyl -malolactonates (MLARs), PMLABe homopolymers and copolymers, are reviewed. Focus is placed on the ring-opening polymerization (ROP) of MLABe and on copolymers of MLABe, with relevant data on the performances of the initiating systems and on the PMLABes molecular characteristics, along with detailed mechanistic insights, being reported

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Section: Copolymerization Of Mlabe With Lactidesmentioning

confidence: 99%

Benzyl β-malolactonate polymers: a long story with recent advances

Jaffredo

Guillaume

2014

Polym. Chem.

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“…A variety of functional groups, such as cyclic ketal group, , aromatic, , carbonyl, carboxyl, ,, and amino, have been introduced onto the PCL segment. For example, the attachment of aromatic, hydroxyl, carboxyl, and hydrophobic drug on the polyester chain can change the thermodynamic and kinetic stability of NPs. ,− Moreover, the introduction of functional groups into the core block can adjust the encapsulation and release properties of NPs via some special interactions between the core forming block and drug, such as π–π interaction, , hydrogen bond, , electrostatic complexation, , and some chemical reaction. , In a word, the introduction of functional groups to the polyester segment has exhibited great potentials for the modifications in the stability, biodegradation, drug solubility and release properties of NPs. Despite significant advances, the introduction of functional groups to the polyester segment is still a challenge.…”

Section: Introductionmentioning

confidence: 99%

Poly(ethyleneglycol)-b-Poly(ε-caprolactone-co-γ-hydroxyl-ε- caprolactone) Bearing Pendant Hydroxyl Groups as Nanocarriers for Doxorubicin Delivery

et al. 2012

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A novel biodegradable amphiphilic diblock copolymer methoxy poly(ethylene glycol)-b-poly(ε-caprolactone-co-γ-hydroxyl-ε-caprolactone) (mPEG-b-P(CL-co-HCL)) bearing pendant hydroxyl groups on the PCL block was prepared. The hydroxyl groups were formed through the reduction of ketones by sodium borohydride without protection and deprotection. The obtained polymers were well characterized by (1)H NMR, Fourier transform infrared (FT-IR), gel permeation chromatography (GPC), differential scanning calorimetry (DSC), X-ray diffraction (XRD), and contact angle measurement. mPEG-b-P(CL-co-HCL) could self-assemble into stable nanoparticles (NPs) with critical micellar concentrations (CMC) of 6.3 × 10(-4) ∼ 8.1 × 10(-4) mg/mL. The NPs prepared from mPEG-b-P(CL-co-HCL) were spherical in shape with diameters about 100 to 140 nm. The hydrophobic doxorubicin (DOX) was chosen as a drug model and successfully encapsulated into the NPs. The encapsulation efficiency and release kinetics of DOX were investigated. The results indicated that the introduction of hydroxyl groups onto the core-forming block could decrease the hydrophobicity of copolymers, thus improving the storage stability of NPs in aqueous solution. Moreover, higher loading capacity and slower in vitro release of DOX were observed, which was due to the hydrogen-bonding formation between DOX and hydroxyl groups. Meanwhile, the MTT assay demonstrated that the blank NPs were biocompatible to HepG2 cell,s while free DOX and DOX-loaded NPs showed significant cytotoxicity against the cells. Moreover, Compared to the free DOX, the DOX-loaded NPs were more efficiently internalized by HepG2 cells. In sum, the introduction of hydroxyl groups on the polyester block in mPEG-b-P(CL-co-HCL) exhibited great potentials for modifications in the stability, drug solubilization, and release properties of NPs.

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“…Unlike poly( L ‐lactide) or poly( D ‐lactide) which are characterized by high tensile strength and low ultimate elongation, poly( DL‐ lactide) is an amorphous material which exhibits lower tensile strength and higher ultimate elongation 24. DL‐LA has been used for copolymerization or blending with other polymers containing glycolide,25 ethylene oxide,26 ε‐caprolactone,27–29 and amino acids such as glycine 30. Aslan et al blended poly( DL‐ lactide) and poly(ε‐caprolactone) and the latter decreased the modulus and elongation‐at‐yield of the blend compared to neat PDLLA 27.…”

Section: Discussionmentioning

confidence: 99%

Synthesis and characterization of functionalized biodegradable poly(DL‐lactide‐co‐RS‐β‐malic acid)

He¹,

Poon²,

Feng³

et al. 2008

J Biomedical Materials Res

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Amorphous poly(DL-lactide-co-RS-beta-malic acid) (PDLLMAc) was synthesized by hydrogenolysis of poly(DL-lactide-co-RS-beta-malolactonate) (PDLLMA), which was obtained from the ring-opening polymerization of DL-lactide (DLLA) and RS-beta-benzyl malolactonate (MA) using stannous octoate as the catalyst. The amount of malolactonate (MA) in the feeding dose was varied from 0 to 8.0 mol %. The copolymers were characterized by 1H NMR, FTIR, GPC, and DSC. The tensile properties and water uptake of the copolymers were measured. The protective benzyl groups in PDLLMA were completely removed in hydrogenolysis to produce PDLLMAc. The molecular weight (M(n)) of the copolymers decreased with increasing MA content. However, with low feed MA content of 0.6 and 1.0%, high molecular weight PDLLMAc with M(n) of 63 and 35 kDa, respectively, were obtained; these copolymers exhibited good tensile yield stress and modulus of 17-23 MPa and 1.1-1.4 GPa, which are comparable to PDLLA homopolymer. The corresponding protected PDLLMA have tensile yield stress/modulus of 2.0-2.4 MPa and 11-42 MPa. The malic acid comonomer in PDLLMAc significantly improves the tensile strength and modulus compared to the protected PDLLMA. Further, the functionalizable PDLLMAc (with 0.6 mol % feed MA) was grafted with bioactive RGD peptide. The culture of primary umbilical artery smooth muscle cells was investigated. Methylthiazoletetrazolium results showed that both the RGD- and COOH-functionalized (0.6 mol %) PDLLMAc copolymers were significantly more biocompatible than the control PDLLA and could potentially be employed as tissue engineering scaffolds.

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Synthesis and characterization of a functionalized amphiphilic diblock copolymer: MePEG-b-poly(DL-lactide-co-RS-β-malic acid)

Cited by 10 publications

References 43 publications

Benzyl β-malolactonate polymers: a long story with recent advances

Benzyl β-malolactonate polymers: a long story with recent advances

Poly(ethyleneglycol)-b-Poly(ε-caprolactone-co-γ-hydroxyl-ε- caprolactone) Bearing Pendant Hydroxyl Groups as Nanocarriers for Doxorubicin Delivery

Synthesis and characterization of functionalized biodegradable poly(DL‐lactide‐co‐RS‐β‐malic acid)

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