Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Enzymatic Polymerization of an Ibuprofen-Containing Monomer and Subsequent Drug Release.

ABSTRACT: Novel ibuprofen-containing monomers comprising naturally occurring and biocompatible compounds were synthesized and subsequently polymerized via enzymatic methods. Through the use of a malic acid sugar backbone, ibuprofen was attached as a pendant group, and then subsequently polymerized with a linear aliphatic diol (1,3-propanediol, 1,5-pentanediol, or 1,8-octanediol) as comonomer using lipase B from Candida antarctica, a greener alternative to traditional metal catalysts. Polymer structures were elucidated by nuclear magnetic resonance and infrared spectroscopies, and thermal properties and molecular weights were determined. All polymers exhibited sustained ibuprofen release, with the longer chain, more hydrophobic diols exhibiting the slowest release over the 30 d study. Polymers were deemed cytocompatible using mouse fibroblasts, when evaluated at relevant therapeutic concentrations. Additionally, ibuprofen retained its chemical integrity throughout the polymerization and in vitro hydrolytic degradation processes. This methodology of enzymatic polymerization of a drug presents a more environmentally friendly synthesis and a novel approach to bioactive polymer conjugates.

SUBMITTER: Stebbins ND

PROVIDER: S-EPMC4534339 | biostudies-literature | 2015 Aug

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Similar Datasets

Acrylate monomer polymerization triggered by iron oxide magnetic nanoparticles and catechol containing microgels.

Project description:Phenol and its derivatives are the most used polymerization inhibitors for vinyl-based monomers. Here, we reported a novel catalytic system composed of mussel inspired adhesive moiety, catechol, in combination with iron oxide nanoparticles (IONPs) to generate hydroxyl radical (•OH) at pH 7.4. Catechol-containing microgel (DHM) was prepared by copolymerizing dopamine methacrylamide (DMA) and N-hydroxyethyl acrylamide (HEAA), which generated superoxide (•O2-) and hydrogen peroxide (H2O2) as a result of catechol oxidation. In the presence of IONPs, the generated reactive oxygen species were further converted to •OH, which initiated free radical polymerization of various water-soluble acrylate-based monomers including neutral (acrylamide, methyl acrylamide, etc.), anionic (2-acrylamido-2-methyl-1-propanesulfonic acid sodium salt), cationic ([2-(methacryloyloxy)ethyl]trimethylammonium chloride), and zwitterionic (2-(methacryloyloxy)ethyl]dimethyl-(3-sulfopropyl)ammonium hydroxide) monomers. Compared with the typical free radical initiating systems, the reported system does not require the addition of extra initiators for polymerization. During the process of polymerization, a bilayer hydrogel was formed in situ and exhibited the ability to bend during the process of swelling. The incorporation of IONPs significantly enhanced magnetic property of the hydrogel and the combination of DHM and IONPs also improved the mechanical properties of these hydrogels.

| S-EPMC10275414 | biostudies-literature

Drug release from hydrazone-containing peptide amphiphiles.

Project description:Hydrolytically-labile hydrazones in peptide amphiphiles were studied as degradable tethers for release of the drug nabumetone from nanofiber gels. On-resin addition of the novel compound tri-Boc-hydrazido adipic acid to a lysine ?-amine allowed for precise placement of a hydrazide in a peptide sequence.

| S-EPMC3292209 | biostudies-literature

Evaluation of the Structural Modification of Ibuprofen on the Penetration Release of Ibuprofen from a Drug-in-Adhesive Matrix Type Transdermal Patch.

Project description:This study aimed to evaluate the effect of chemical modifications of the structure of active compounds on the skin permeation and accumulation of ibuprofen [IBU] from the acrylic pressure-sensitive adhesive used as a drug-in-adhesives matrix type transdermal patch. The active substances tested were ibuprofen salts obtained by pairing the ibuprofen anion with organic cations, such as amino acid isopropyl esters. The structural modification of ibuprofen tested were Ibuprofen sodium salt, [GlyOiPr][IBU], [AlaOiPr][IBU], [ValOiPr][IBU], [SerOiPr][IBU], [ThrOiPr][IBU], [(AspOiPr)2][IBU], [LysOiPr][IBU], [LysOiPr][IBU]2, [PheOiPr][IBU], and [ProOiPr][IBU]. For comparison, the penetration of unmodified ibuprofen and commercially available patches was also investigated. Thus, twelve transdermal patches with new drug modifications have been developed whose adhesive carrier is an acrylate copolymer. The obtained patches were characterized for their adhesive properties and tested for permeability of the active substance. Our results show that the obtained ibuprofen patches demonstrate similar permeability to commercial patches compared to those with structural modifications of ibuprofen. However, these modified patches show an increased drug permeability of 2.3 to even 6.4 times greater than unmodified ibuprofen. Increasing the permeability of the active substance and properties such as adhesion, cohesion, and tack make the obtained patches an excellent alternative to commercial patches containing ibuprofen.

| S-EPMC9320482 | biostudies-literature

Investigation on the Drug Release Efficacy of the Ibuprofen-Loaded ZIF-8/Fe3O4 NPs Nanocarrier

Project description: Not available

| S-EPMC11292841 | biostudies-literature

Linear Polymerization of Protein by Sterically Controlled Enzymatic Cross-Linking with a Tyrosine-Containing Peptide Loop.

Project description:The structure of a protein complex needs to be controlled appropriately to maximize its functions. Herein, we report the linear polymerization of bacterial alkaline phosphatase (BAP) through the site-specific cross-linking reaction catalyzed by Trametes sp. laccase (TL). We introduced a peptide loop containing a tyrosine (Y-Loop) to BAP, and the Y-Looped BAP was treated with TL. The Y-Looped BAP formed linear polymers, whereas BAP fused with a C-terminal peptide containing a tyrosine (Y-tag) showed an irregular shape after TL treatment. The sterically confined structure of the Y-Loop could be responsible for the formation of linear BAP polymers. TL-catalyzed copolymerization of Y-Looped BAP and a Y-tagged chimeric antibody-binding protein, pG2pA-Y, resulted in the formation of linear bifunctional protein copolymers that could be employed as protein probes in an enzyme-linked immunosorbent assay (ELISA). Copolymers comprising Y-Looped BAP and pG2pA-Y at a molar ratio of 100:1 exhibited the highest signal in the ELISA with 26- and 20-fold higher than a genetically fused chimeric protein, BAP-pG2pA-Y, and its polymeric form, respectively. This result revealed that the morphology of the copolymers was the most critical feature to improve the functionality of the protein polymers as detection probes, not only for immunoassays but also for other diagnostic applications.

| S-EPMC7081431 | biostudies-literature

Living supramolecular polymerization based on reversible deactivation of a monomer by using a 'dummy' monomer.

Project description:Although living supramolecular polymerization (LSP) has recently been realized, the scope of the monomer structures applicable to the existing methods is still limited. For instance, a monomer that spontaneously nucleates itself cannot be processed in a manner consistent with LSP. Herein, we report a new method for such a "reactive" monomer. We use a 'dummy' monomer which has a similar structure to the reactive monomer but is incapable of one-dimensional supramolecular polymerization. We show that in the presence of the dummy monomer, the reactive monomer is kinetically trapped in the dormant state. In this way, spontaneous nucleation of the reactive monomer is retarded; yet, addition of seeds of a supramolecular polymer can initiate the supramolecular polymerization in a chain growth manner. As a result, we obtain the supramolecular polymer of the reactive monomer with a controlled length, which is otherwise thermodynamically inaccessible. We believe that this concept will expand the scope of LSP for the synthesis of other functional supramolecular polymers, and thus lead to a variety of applications.

| S-EPMC6640193 | biostudies-literature

Chemoselective polymerization control: from mixed-monomer feedstock to copolymers.

Project description:A novel chemoselective polymerization control yields predictable (co)polymer compositions from a mixture of monomers. Using a dizinc catalyst and a mixture of caprolactone, cyclohexene oxide, and carbon dioxide enables the selective preparation of either polyesters or polycarbonates or copoly(ester-carbonates). The selectivity depends on the nature of the zinc-oxygen functionality at the growing polymer chain end, and can be controlled by the addition of exogeneous switch reagents.

| S-EPMC4232277 | biostudies-literature

The limits of precision monomer placement in chain growth polymerization.

Project description:Precise control over the location of monomers in a polymer chain has been described as the 'Holy Grail' of polymer synthesis. Controlled chain growth polymerization techniques have brought this goal closer, allowing the preparation of multiblock copolymers with ordered sequences of functional monomers. Such structures have promising applications ranging from medicine to materials engineering. Here we show, however, that the statistical nature of chain growth polymerization places strong limits on the control that can be obtained. We demonstrate that monomer locations are distributed according to surprisingly simple laws related to the Poisson or beta distributions. The degree of control is quantified in terms of the yield of the desired structure and the standard deviation of the appropriate distribution, allowing comparison between different synthetic techniques. This analysis establishes experimental requirements for the design of polymeric chains with controlled sequence of functionalities, which balance precise control of structure with simplicity of synthesis.

| S-EPMC4740409 | biostudies-literature

Polymerization driven monomer passage through monolayer chemical vapour deposition graphene.

Project description:Mass transport through graphene is receiving increasing attention due to the potential for molecular sieving. Experimental studies are mostly limited to the translocation of protons, ions, and water molecules, and results for larger molecules through graphene are rare. Here, we perform controlled radical polymerization with surface-anchored self-assembled initiator monolayer in a monomer solution with single-layer graphene separating the initiator from the monomer. We demonstrate that neutral monomers are able to pass through the graphene (via native defects) and increase the graphene defects ratio (Raman ID/IG) from ca. 0.09 to 0.22. The translocations of anionic and cationic monomers through graphene are significantly slower due to chemical interactions of monomers with the graphene defects. Interestingly, if micropatterned initiator-monolayers are used, the translocations of anionic monomers apparently cut the graphene sheet into congruent microscopic structures. The varied interactions between monomers and graphene defects are further investigated by quantum molecular dynamics simulations.

| S-EPMC6170411 | biostudies-literature

Cyclodextrin-containing hydrogels as an intraocular lens for sustained drug release.

Project description:To improve the efficacy of anti-inflammatory factors in patients who undergo cataract surgery, poly(2-hydroxyethyl methacrylate-co-methyl methacrylate) (p(HEMA-co-MMA)) hydrogels containing β-cyclodextrin (β-CD) (pHEMA/MMA/β-CD) were designed and prepared as intraocular lens (IOLs) biomaterials that could be loaded with and achieve the sustained release of dexamethasone. A series of pHEMA/MMA/β-CD copolymers containing different ratios of β-CD (range, 2.77 to 10.24 wt.%) were obtained using thermal polymerization. The polymers had high transmittance at visible wavelengths and good biocompatibility with mouse connective tissue fibroblasts. Drug loading and release studies demonstrated that introducing β-CD into hydrogels increased loading efficiency and achieved the sustained release of the drug. Administering β-CD via hydrogels increased the equilibrium swelling ratio, elastic modulus and tensile strength. In addition, β-CD increased the hydrophilicity of the hydrogels, resulting in a lower water contact angle and higher cellular adhesion to the hydrogels. In summary, pHEMA/MMA/β-CD hydrogels show great potential as IOL biomaterials that are capable of maintaining the sustained release of anti-inflammatory drugs after cataract surgery.

| S-EPMC5731761 | 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