Synthesis and characterization of novel copolymers based on 3(S)-methyl-morpholine-2,5-dione

Feng, Yakai; Chen, Chengbin; Zhang, Li; Tian, Hong; Yuan, Wenjie

doi:10.1007/s12209-012-1864-9

Cited by 13 publications

(11 citation statements)

References 24 publications

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“…Therefore, the amphiphilic block copolymers have the potential as safe and effi cient gene carriers, and the NPs/pEGFP-ZNF580 complexes might enhance the rapid endothelialization of artifi cial blood vessels. [ 70 ] Synthesis of Amphiphilic Block Copolymers: Synthesis of P(LA-co-MMD) : P(LA-co -MMD) copolymers were prepared as reported previously by ROP. [ 71 ] Three copolymers named P(LA-co -MMD) 1 , P(LA-co -MMD) 2 , and P(LA-co -MMD) 3 were obtained, in which the subscripts 1, 2, and 3 indicate the MMD contents (10 wt%, 20 wt%, and 30 wt%) in feed (Table S1, Supporting Information).…”

Section: Discussionmentioning

confidence: 99%

Nanoparticles Complexed with Gene Vectors to Promote Proliferation of Human Vascular Endothelial Cells

Shi

Zhang

et al. 2015

Adv Healthcare Materials

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Amphiphilic block copolymers containing biodegradable hydrophobic segments of depsipeptide based copolymers have been synthesized and explored as gene carriers for enhancing proliferation of endothelial cells in vitro. These polymers form nanoparticles (NPs) with positive charges on their surface, which could condense recombinant plasmids of enhanced green fluorescent protein plasmid and ZNF580 gene (pEGFP-ZNF580) and protect them against DNase I. ZNF580 gene is efficiently transported into EA.hy926 cells to promote their proliferation, whereby the transfection efficiency of NPs/pEGFP-ZNF580 is approximately similar to that of Lipofectamine 2000. These results indicate that the NPs might have potential as a carrier for pEGFP-ZNF580, which could support endothelialization of cardiovascular implants.

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Section: Discussionmentioning

confidence: 99%

Nanoparticles Complexed with Gene Vectors to Promote Proliferation of Human Vascular Endothelial Cells

Shi

Zhang

et al. 2015

Adv Healthcare Materials

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“…These monomers, that is, morpholine‐2,5‐dione ( M1 ), (S)‐3‐methylmorpholine‐2,5‐dione ( M2 ), and (S)‐3‐ iso‐ butylmorpholine‐2,5‐dione ( M4 ), have been reported to undergo homopolymerization by ROP in the presence of tin‐(II)‐octoate (Sn(Oct) 2 ), that is, the standard catalyst that is also used for the ROP of lactide. Feng et al.…”

Section: Methodsmentioning

confidence: 99%

“…[9] Similar to peptides, the substituent of the amino acid determines the hydrophilicity or lipophilicity of the resulting PEAs. As an example, polymers based on glycine or alanine would be less lipophilic than PEAs obtained from monomers made from the more hydrophobic valine, leucine, or isoleucine.These monomers, that is, morpholine-2,5-dione [10] (M1), (S)-3-methylmorpholine-2,5-dione [11][12][13] (M2), and (S)-3-isobutylmorpholine-2,5-dione [14] (M4), have been reported to undergo homopolymerization by ROP in the presence of tin-(II)-octoate (Sn(Oct) 2 ), that is, the standard catalyst that is also used for the ROP of lactide. Feng et al reported the polymerization of (S)-3-iso-propylmorpholine-2,5-dione (M3) in the presence of a lipase as a catalyst.…”

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confidence: 99%

TBD‐Catalyzed Ring‐Opening Polymerization of Alkyl‐Substituted Morpholine‐2,5‐Dione Derivatives

Dirauf

Bandelli

Weber

et al. 2018

Macromol. Rapid Commun.

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In a two-step synthesis, five different alkyl-substituted morpholine-2,5-dione monomers were synthesized from the natural amino acids glycine, alanine, valine, leucine, and isoleucine. The heterocyclic compounds crystallize in a boat-like conformation and are polymerized via 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD)-catalyzed ring-opening polymerization (ROP) in tetrahydrofuran. Well-defined polymers could be obtained from the monomers based on valine, leucine, and isoleucine at a feed ratio of M/I/TBD = 100/1/0.5. Kinetic studies of the ROP reveal that the molar masses and dispersities (Đ < 1.2) could be well controlled, as confirmed by size exclusion chromatography and H NMR spectroscopy. At conversions above 50%, the polymerization rate decreases and the dispersity slightly increases, presumably due to transesterification. Matrix-assisted laser desorption time-of-flight mass spectrometry indicates the presence of polymer chains with α-end groups derived from the initiator.

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“…17 The use of cyclic MD monomers allows for easy copolymerization with other cyclic monomers such as lactides and e-caprolactone (CL). [18][19][20][21] Previously, triblock copolymers of leucine-derived PDP with poly(L-lactide) (PLLA) and poly(ethylene glycol) (PEG) have been studied for use as antiadhesive membranes, 22 and multiblock copolymers of various PDPs and PCL have shown stimuli-responsive behavior. 23 Triblock copolymers of alanine-derived PDP with PLLA and PEG have been used as micellar drug delivery systems.…”

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confidence: 99%

Biodegradable photocrosslinkable poly(depsipeptide‐co‐ε‐caprolactone) for tissue engineering: Synthesis, characterization, and In vitro evaluation

Elomaa

Kang

Seppälä

et al. 2014

J. Polym. Sci. Part A: Polym. Chem.

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Stereolithography has become increasingly popular in scaffold fabrication due to automation and well-controlled geometry complexity, and consequently, there is a great need for new suitable biodegradable photocrosslinkable polymers. In this study, a new type of photocrosslinkable poly(ester amide) was synthesized based on e-caprolactone and L-alaninederived depsipeptide and was applied to fabrication of threedimensional (3D) scaffolds by stereolithography. 1 H nuclear magnetic resonance and Fourier transform infra-red analysis confirmed the formation of new bonds during the polymer synthesis. Incorporation of depsipeptide increased the glass transition temperature and hydrophilicity of the polymer and accelerated hydrolytic degradation compared with the poly(ecaprolactone) homopolymer. The compressive strength of the 3D scaffolds increased with the increasing depsipeptide content. This work demonstrated that incorporation of depsipeptide into photocrosslinkable polyesters resulted in excellent cytocompatibility and tunable degradation rates and mechanical properties and thus expanded the repertoire of biomaterials suitable for 3D photofabrication of high-resolution tissue engineering scaffolds.

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Synthesis and characterization of novel copolymers based on 3(S)-methyl-morpholine-2,5-dione

Cited by 13 publications

References 24 publications

Nanoparticles Complexed with Gene Vectors to Promote Proliferation of Human Vascular Endothelial Cells

Nanoparticles Complexed with Gene Vectors to Promote Proliferation of Human Vascular Endothelial Cells

TBD‐Catalyzed Ring‐Opening Polymerization of Alkyl‐Substituted Morpholine‐2,5‐Dione Derivatives

Biodegradable photocrosslinkable poly(depsipeptide‐co‐ε‐caprolactone) for tissue engineering: Synthesis, characterization, and In vitro evaluation

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