Browse
Submit Data
Databases
API
Help

Dataset Information

17 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

A Versatile Monomer for Preparing Well-Defined Functional Polycarbonates and Poly(ester-carbonates).

ABSTRACT: Despite the increasing demands for functional degradable biomaterials, strategies for generating materials with modular compositions and well-defined functionalities from common building blocks are still lacking. Here we report an azido-functionalized cyclic carbonate monomer, AzDXO, that exhibited controlled/"living" ring-opening polymerization kinetics under the catalysis of 1,8-diazabicyclo[5.4.0]-undec-7-ene. Homopolymerization of AzDXO and copolymerization of AzDXO with lactide resulted in polycarbonate and poly(ester-carbonates) with well-defined composition and narrow polydispersity. Further side-chain functionalizations of these polymers were accomplished under facile conditions via copper-catalyzed or copper-free strain-promoted azido-alkyne cyclcoaddition. This versatile monomer building block, obtainable in two steps without tedious purifications, provides a practical solution to the preparation of well-defined functional polycarbonates and poly(ester-carbonates).

SUBMITTER: Xu J

PROVIDER: S-EPMC3115654 | biostudies-literature | 2011 Apr

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

A Versatile Monomer for Preparing Well-Defined Functional Polycarbonates and Poly(ester-carbonates).

Xu Jianwen J Prifti Fioleda F Song Jie J

Macromolecules 20110401 8

Despite the increasing demands for functional degradable biomaterials, strategies for generating materials with modular compositions and well-defined functionalities from common building blocks are still lacking. Here we report an azido-functionalized cyclic carbonate monomer, AzDXO, that exhibited controlled/"living" ring-opening polymerization kinetics under the catalysis of 1,8-diazabicyclo[5.4.0]-undec-7-ene. Homopolymerization of AzDXO and copolymerization of AzDXO with lactide resulted in ...[more]

PMID: 21686053

Similar Datasets

Novozym 435-Catalyzed Synthesis of Well-Defined Hyperbranched Aliphatic Poly(β-thioether ester).

Project description:A series of new hyperbranched aliphatic poly(β-thioether ester)s were prepared by the enzymatic ring-opening polycondensation of 1,4-oxathiepan-7-one (OTO) and AB2/ABB' comonomer with acid-labile β-thiopropionate groups. Two kinds of comonomers, methyl 3-((3-hydroxy-2-(hydroxymethyl)propyl)thio)propanoate (HHTP) and methyl 3-((2,3-dihydroxypropyl)thio)propanoate (DHTP), with different primary alcohols and secondary alcohols, were synthesized by thiol-ene click chemistry and thiol-ene Michael addition, respectively. Immobilized lipase B from Candida antarctica (CALB), Novozym 435, was used as the catalyst. The random copolymers were characterized by 1H-NMR, 13C-NMR, GPC, TGA, and DSC. All branched copolyesters had high molecular weights over 15,000 Da with narrow polydispersities in the range of 1.75-2.01 and were amorphous polymers. Their degradation properties under acidic conditions were also studied in vitro. The polymeric nanoparticles of hyperbranched poly(β-thioether ester)s were successfully obtained and showed good oxidation-responsive properties, indicating their potential for biomedical applications.

| S-EPMC7037349 | biostudies-literature

Well-defined Poly(lactic acid)s Containing Poly(ethylene glycol) Side-chains.

Project description:Poly(ethylene glycol) (PEG) side-chain functionalized lactide analogues have been synthesized in four steps from commercially available L-lactide. The key step in the synthesis is the 1,3-dipolar cycloaddition between PEG-azides and a highly strained spirolactide-heptene monomer, which proceeds in high conversions. The PEG-grafted lactides analogues were polymerized via ring-opening polymerization using triazacyclodecene as organocatalyst to give well-defined tri- and hepta-(ethylene glycol)-poly(lactide)s (PLA) with molecular weights above 10 kDa and polydispersity indices between 1.6 and 2.1. PEG-poly(lactide) (PLA) with PEG chain M(n) 2000 was also prepared but GPC analysis showed a bimodal profile indicating the presence of starting macromonomer. Cell adhesion assays were performed using MC3T3 E-1 osteoblast-like cells demonstrating that PEG-containing PLA reduces cell adhesion significantly when compared to unfunctionalized PLA.

| S-EPMC3263433 | biostudies-literature

Degradable Poly(ether-ester-urethane)s Based on Well-Defined Aliphatic Diurethane Diisocyanate with Excellent Shape Recovery Properties at Body Temperature for Biomedical Application.

Project description:The aim of this study is to offer a new class of degradable shape-memory poly(ether-ester-urethane)s (SMPEEUs) based on poly(ether-ester) (PECL) and well-defined aliphatic diurethane diisocyanate (HBH) for further biomedical application. The prepolymers of PECLs were synthesized through bulk ring-opening polymerization using ?-caprolactone as the monomer and poly(ethylene glycol) as the initiator. By chain extension of PECL with HBH, SMPEEUs with varying PEG content were prepared. The chemical structures of the prepolymers and products were characterized by GPC, 1H NMR, and FT-IR, and the effect of PEG content on the physicochemical properties (especially the shape recovery properties) of SMPEEUs was studied. The microsphase-separated structures of the SMPEEUs were demonstrated by DSC and XRD. The SMPEEU films exhibited good tensile properties with the strain at a break of 483%-956% and an ultimate stress of 23.1-9.0 MPa. Hydrolytic degradation in vitro studies indicated that the time of the SMPEEU films becoming fragments was 4-12 weeks and the introduction of PEG facilitates the degradation rate of the films. The shape memory properties studies found that SMPEEU films with a PEG content of 23.4 wt % displayed excellent recovery properties with a recovery ratio of 99.8% and a recovery time of 3.9 s at body temperature. In addition, the relative growth rates of the SMPEEU films were greater than 75% after incubation for 72 h, indicating good cytocompatibility in vitro. The SMPEEUs, which possess not only satisfactory tensile properties, degradability, nontoxic degradation products, and cytocompatibility, but also excellent shape recovery properties at body temperature, promised to be an excellent candidate for medical device applications.

| S-EPMC6631253 | biostudies-literature

A protocol for preparing nucleotide-free KaiC monomer.

Project description:The hexameric form of the KaiC protein is a core of the cyanobacterial biological clock, and its enzymatic activities exhibit circadian periodicity. The instability of the monomeric form of nucleotide-free KaiC has precluded its storage and detailed analyses of the activities of the reassembled hexamer. Here, we provide a protocol for preparing nucleotide-free KaiC monomer that is stable in solution and for triggering its reassembly into intact KaiC hexamer by the addition of ATP. A phosphate buffer containing glutamic acid and arginine enhanced the stability of KaiC monomer considerably. In addition, we found that reassembled KaiC hexamer was functionally active as the intact hexamer. This protocol provides a methodological basis for further analyses of first-turnover events of the ATPase/autokinase/autophosphatase activities of the KaiC hexamer.

| S-EPMC4736791 | biostudies-literature

Well-Defined Poly(Ester Amide)-Based Homo- and Block Copolymers by One-Pot Organocatalytic Anionic Ring-Opening Copolymerization of N-Sulfonyl Aziridines and Cyclic Anhydrides.

Project description:We report a new synthetic methodology for poly(ester amide)s by anionic ring-opening copolymerization of N-sulfonyl aziridines and cyclic anhydrides. Phosphazenes organocatalysts have been found to promote a highly-active, controlled, and selective alternating copolymerization in the absence of any competitive side reaction (zwitterionic mechanism and exchange transacylations). Mechanistic studies have shown first-order dependence of the copolymerization rate in N-sulfonyl aziridines and phosphazenes, and zero-order in cyclic anhydrides. This one-pot methodology leads not only to homopolymers but also to poly(ester amide)-based block copolymers. Two catalytic cycles involving ring-opening alternating copolymerization of N-sulfonyl aziridines with cyclic anhydrides and ring-opening polymerization of N-sulfonyl aziridines have been proposed to explain the one pot synthesis of poly(ester amide)-based homo- and block copolymers.

| S-EPMC8048504 | biostudies-literature

Aldehyde-functional polycarbonates as reactive platforms.

Project description:Ozonolysis of allyl-functional polycarbonates provides aldehyde-functional polycarbonates that have potential to be reactive platforms for transformation into diverse active materials.

| S-EPMC4285359 | biostudies-literature

Anionic polycondensation and equilibrium driven monomer formation of cyclic aliphatic carbonates.

Project description:The current work explores the sodium hydride mediated polycondensation of aliphatic diols with diethyl carbonate to produce both aliphatic polycarbonates and cyclic carbonate monomers. The lengths of the diol dictate the outcome of the reaction; for ethylene glycol and seven other 1,3-diols with a wide array of substitution patterns, the corresponding 5-membered and 6-membered cyclic carbonates were synthesized in excellent yield (70-90%) on a 100 gram scale. Diols with longer alkyl chains, under the same conditions, yielded polycarbonates with an M w ranging from 5000 to 16 000. In all cases, the macromolecular architecture revealed that the formed polymer consisted purely of carbonate linkages, without decarboxylation as a side reaction. The synthetic design is completely solvent-free without any additional post purification steps and without the necessity of reactive ring-closing reagents. The results presented within provide a green and scalable approach to synthesize both cyclic carbonate monomers and polycarbonates with possible applications within the entire field of polymer technology.

| S-EPMC9090641 | biostudies-literature

A Novel Synthesis of Poly(Ester-Alt-Selenide)s by Ring-Opening Copolymerization of ?-Selenobutyrolactone and Epoxy Monomer.

Project description:Ring-opening copolymerization (ROCOP) is an effective means to prepare functionalized polyester. In this work, a type of selenide-containing polyesters with controllable structure, molecular weight, and molecular weight distribution was successfully prepared by ROCOP of ?-selenobutyrolactone and epoxy compounds. The influence of the catalyst, solvent, and reaction temperature on the reaction efficiency was examined. Then, kinetic study was investigated under an optimized condition. The structure of the copolymers was carefully characterized by nuclear magnetic resonance (NMR), 1H NMR, 13C NMR, and 77Se NMR, Matrix-assisted laser-desorption-ionization time-of-flight mass spectrometry (MALDI-TOF-MS), and size exclusion chromatography (SEC). The resulting polymers showed a linear structure with a sequence regulated backbone repeating unit of ester-selenide. On this basis, some typical epoxides were investigated to verify the scope of the polymerization system. Due to the "living"/controlled characteristics of this ROCOP, multiblock, amphiphilic, and stereotactic copolymers could be prepared with a pre-designed structure. As expected, the selenide-containing amphiphilic copolymer could self-assemble to micelles and showed an oxidative response.

| S-EPMC7285084 | biostudies-literature

Ring-opening polymerization of prodrugs: a versatile approach to prepare well-defined drug-loaded nanoparticles.

Project description:The synthesis of polymer-drug conjugates from prodrug monomers consisting of a cyclic polymerizable group that is appended to a drug through a cleavable linker is achieved by organocatalyzed ring-opening polymerization. The monomers polymerize into well-defined polymer prodrugs that are designed to self-assemble into nanoparticles and release the drug in response to a physiologically relevant stimulus. This method is compatible with structurally diverse drugs and allows different drugs to be copolymerized with quantitative conversion of the monomers. The drug loading can be controlled by adjusting the monomer(s)/initiator feed ratio and drug release can be encoded into the polymer by the choice of linker. Initiating these monomers from a poly(ethylene glycol) macroinitiator results in amphiphilic diblock copolymers that spontaneously self-assemble into micelles with a long plasma circulation, which is useful for systemic therapy.

| S-EPMC4293338 | biostudies-literature

The synthesis of well-defined poly(vinylbenzyl chloride)-grafted nanoparticles via RAFT polymerization.

Project description:We describe the use of one of the most advanced radical polymerization techniques, the reversible addition fragmentation chain transfer (RAFT) process, to produce highly functional core-shell particles based on a silica core and a shell made of functional polymeric chains with very well controlled structure. The versatility of RAFT polymerization is illustrated by the control of the polymerization of vinylbenzyl chloride (VBC), a highly functional monomer, with the aim of designing silica core-poly(VBC) shell nanoparticles. Optimal conditions for the control of VBC polymerization by RAFT are first established, followed by the use of the "grafting from" method to yield polymeric brushes that form a well-defined shell surrounding the silica core. We obtain particles that are monodisperse in size, and we demonstrate that the exceptional control over their dimensions is achieved by careful tailoring the conditions of the radical polymerization.

| S-EPMC3701384 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data