betadex and glycidyl-methacrylate

Although various cyclodextrins (CDs) have been utilized to prepare organic polymer-based monolithic columns, there were few reports on fabrication of cyclodextrin functionalized hybrid monolithic columns. Herein, a sulfobutylether β-cyclodextrin (SBE-β-CD)-silica hybrid monolithic column was prepared by "one-step" method via the co-polymerization of hydrolyzed organosiloxane precursors and glycidyl methacrylate-sulfobutylether β-cyclodextrin (GMA-SBE-β-CD). The morphologies of prepared monolithic columns were observed by optical microscopy and scanning electron microscopy (SEM). The sulfobutylether β-cyclodextrin was incorporated into the polymeric structure, which was demonstrated by energy dispersive X-ray spectroscopy (EDS), Fourier-transform infrared spectroscopy (FTIR) spectrum and X-ray photoelectron spectroscopy (XPS). The resulting columns were used for chiral separations of twenty six racemic compounds, and satisfactory separation selectivity was obtained. Compared with other two kinds of neutral cyclodextrin (β-CD and HP-β-CD) based hybrid monoliths, sulfobutylether β-cyclodextrin-silica hybrid monolith showed superior chiral resolution. These results demonstrated the sulfobutylether β-cyclodextrin-silica hybrid monolithic column was promising in chiral compounds analysis.

Topics: 2-Hydroxypropyl-beta-cyclodextrin; beta-Cyclodextrins; Capillary Electrochromatography; Epoxy Compounds; Methacrylates; Microscopy, Electron, Scanning; Photoelectron Spectroscopy; Polymerization; Polymers; Silicon Dioxide; Stereoisomerism

Scarless wound healing is ideal for patients suffering from soft tissue defects. In this study, we prepared a novel wet dressing (β-CD-ic-CUR/GC) based on the visible light-cured glycol chitosan (GC) hydrogel and inclusion complex between beta-cyclodextrin (β-CD) and curcumin (CUR). We also evaluated its efficacy in the acceleration of wound healing as compared to that of CUR-loaded GC (CUR/GC). The conjugation of glycidyl methacrylate (GM) to GC for photo-curing was confirmed by ¹H-NMR measurement, and the photo-cured GC hydrogel was characterized by the analyses of rheology, swelling ratio, SEM and degradation rate. After visible light irradiation, the surface/cross-sectional morphologies and storage (G')/loss (G'') moduli revealed the formation of hydrogel with interconnected porosity. The dressing β-CD-ic-CUR/GC exhibited a controlled release of 90% CUR in a sustained manner for 30 days. On the other hand, CUR/GC showed CUR release of 16%. β-CD acted as an excipient in improving the water-solubility of CUR and affected the release behavior of CUR. The in vivo animal tests including measurement of the remaining unhealed wound area and histological analyses showed that β-CD-ic-CUR/GC may have potential as a wet dressing agent to enhance soft tissue recovery in open fractures.

Topics: Animals; Bandages, Hydrocolloid; beta-Cyclodextrins; Cell Line; Cell Proliferation; Chitosan; Curcumin; Delayed-Action Preparations; Drug Liberation; Epoxy Compounds; Fibroblasts; Hydrogels; Light; Methacrylates; Mice; Mice, Inbred BALB C; Photochemical Processes; Surgical Wound; Wound Healing

In order to investigate the effect of the linking spacer on the enantioseparation ability of β-cyclodextrin (β-CD) functionalized polymeric monoliths, three β-CD-functionalized organic polymeric monoliths with different spacer lengths were prepared by using three amino-β-CDs, i.e. mono-6-amino-6-deoxy-β-CD, mono-6-ethylenediamine-6-deoxy-β-CD, mono-6-hexamethylenediamine-6-deoxy-β-CD, as starting materials. These amino-β-CDs reacted with glycidyl methacrylate to produce functional monomers which were then copolymerized with ethylene dimethacrylate. The enantioseparation ability of the three monoliths was evaluated using 14 chiral acidic compounds, including mandelic acid derivatives, nonsteroidal anti-inflammatory drugs, N-derivatized amino acids, and chiral herbicides under optimum chromatographic conditions. Notably, the poly(GMA-NH2-β-CD-co-EDMA) column provides higher enantioresolution and enantioselectivity than the poly(GMA-EDA-β-CD-co-EDMA) and poly(GMA-HDA-β-CD-co-EDMA) columns for most tested chiral analytes. Furthermore, the enantioseparation performance of triazole-linker containing monoliths was compared to that of ethylenediamine-linker containing monoliths. The results indicate that the enantioselectivity of β-CD monolithic columns is strongly related to the length and type of spacer tethering β-CD to the polymeric support.

Topics: Amination; Amino Acids; Anti-Inflammatory Agents, Non-Steroidal; beta-Cyclodextrins; Chromatography, High Pressure Liquid; Epoxy Compounds; Ethylenediamines; Mandelic Acids; Methacrylates; Methylmethacrylates; Polymerization; Stereoisomerism; Triazoles

Low column efficiency for enantioseparations in capillary liquid chromatography (CLC) is a major problem commonly encountered with β-cyclodextrin (β-CD) functionalized polymer-based monoliths. In order to investigate the effect of the crosslinker type on enantioseparation performance, three commonly used crosslinkers, i.e. 1,4-bis(acryloyl)piperazine (PDA), ethylene dimethacrylate (EDMA) and N,N-methylenebisacrylamide (MBA), were copolymerized using the one-pot approach with glycidyl methacrylate-mono-6-amino-6-deoxy-β-CD (GMA-NH

Topics: Acrylamides; Amino Acids; beta-Cyclodextrins; Chromatography, High Pressure Liquid; Cross-Linking Reagents; Epoxy Compounds; Herbicides; Mandelic Acids; Methacrylates; Permeability; Phenylpropionates; Polymerization

The present work deals with the preparation of innovative cotton textiles which act against blood sucking insects such as mosquitoes. Thus experiments were designed to incorporation of efficient insecticide (Permethrin, bioallethrin) in the macro-molecular structure of modified cotton fabrics. Chemical modification of cotton was realized by grafting with glycidyl methacrylate alone or in combination with β-cyclodextrin by irradiation using fasting electron beam. Retreatment of the so obtained modified cotton was also made to increase the amount of CDs, and in turn, their cavities within the molecular structure of the modified cottons. Finished fabrics were though evaluated using chemical analysis; physical testing, bioassay tests and IR as well as SEM. Results obtained conclude that the amount of insecticide in the finished fabrics increases by increasing of the fixed amount of cyclodextrins which incorporate through their cavities the insecticide. The bioassay test shows that finished cotton fabrics display fast acting against mosquitoes.

Topics: Aedes; Allethrins; Animals; beta-Cyclodextrins; Electrons; Epoxy Compounds; Gossypium; Insecticides; Methacrylates; Permethrin; Polymerization; Radiation, Ionizing; Textiles

A novel and facile one-pot copolymerization approach was developed for the preparation of a β-cyclodextrin (β-CD) functionalized organic polymer monolith. The proposed one-pot process involved two major reactions occurring in sequence in the same vial: (1) the ring opening reaction between the epoxy groups of glycidyl methacrylate (GMA) and the primary amino groups of ethylenediamine-β-CD (EDA-β-CD); (2) the copolymerization of glycidyl methacrylate-ethylenediamine-β-CD (GMA-EDA-β-CD) and ethylene dimethacrylate (EDMA) using 2,2'-azobisisobutyronitrile (AIBN) as the polymerization initiator. This approach avoids the time-consuming post-polymerization derivatization of the traditional two-step strategy. Compared to the previously reported two-step strategy, the monolith prepared by this one-pot method exhibited higher β-CD ligand density and better column efficiency in HPLC. Satisfactory column permeability and separation selectivity were also obtained on the optimized poly(GMA-EDA-β-CD-co-EDMA) monolithic column. Additionally, the column was also applied to the enantioseparation of some racemic acidic compounds with promising results.

Topics: beta-Cyclodextrins; Chromatography, High Pressure Liquid; Epoxy Compounds; Ethylenediamines; Isomerism; Methacrylates; Microscopy, Electron, Scanning

A new restricted access chiral stationary phase was designed and synthesized via atom transfer radical polymerization (ATRP). Surface modified bi-functional silica with chiral selector in the inner layer and hydrophilic external layer was prepared by taking advantage of the controlled/living property of the ATRP method. ATRP initiator bound porous silica was synthesized to perform surface initiated polymerization. The chiral stationary phase was then synthesized by grafting poly(glycidyl methacrylate) (pGMA) on the surface of the silica through "grafting from" polymerization followed by beta-cyclodextrin (beta-CD) immobilization. On the surface of this beta-CD immobilized material, the external pGMA layer was synthesized via second round ATRP using the initiator on the material. The hydrophilic structure was formed after the hydrolysis, which created a diffusion barrier for proteins. The new chiral restricted access material (chiral-CD-RAM) was characterized and its abilities for chiral separation and protein exclusion were evaluated. The result demonstrates that enantio-separations can be achieved for several drugs in HPLC using chiral-CD-RAM as stationary phase. Meanwhile, good protein recovery has been obtained. It indicated that this chiral-CD-RAM can be used for determination of certain chiral drugs in biological samples with direct injection in the HPLC analysis.

Topics: beta-Cyclodextrins; Chromatography, High Pressure Liquid; Epoxy Compounds; Free Radicals; Methacrylates; Pharmaceutical Preparations; Polymers; Porosity; Silicon Dioxide; Stereoisomerism

Polyethylene (PE) and polypropylene (PP) were surface functionalized with beta-cyclodextrin (beta-CD) and hydroxypropyl-beta-cyclodextrin (HP-beta-CD) with the aim of providing PE and PP with the capability of behaving as drug delivery systems. Functionalization was carried out according to a two-step procedure: (i) glycidyl methacrylate (GMA) was grafted by means of gamma radiation and (ii) the epoxy groups of GMA reacted with the hydroxyl groups of CDs forming ether bonds. For a fix radiation dose and GMA concentration, grafting yield (ranging from 1 to 100 micromol GMA cm(-2)) depended on the time during which the preirradiated PE and PP films and slabs were immersed in the GMA solution. CD grafting (from 0.013 to 0.734 micromol cm(-2)) was confirmed by infrared analysis, DSC and the organic compound approach (using 3-methylbenzoic acid as a probe). Functionalization with CDs rendered as highly cytocompatible materials as the starting ones, did not cause relevant changes in the water contact angle and the friction coefficient of PE and PP, but remarkably improved their capability to uptake diclofenac through formation of inclusion complexes with the CDs. Furthermore, the functionalized materials released the drug for 1 h, which could be useful for management of initial pain, inflammation at the insertion site as well as adhesion of certain microorganisms if these materials are used as medicated medical devices.

Topics: 2-Hydroxypropyl-beta-cyclodextrin; Animals; Anti-Inflammatory Agents, Non-Steroidal; BALB 3T3 Cells; beta-Cyclodextrins; Calorimetry, Differential Scanning; Cell Survival; Chemistry, Pharmaceutical; Coated Materials, Biocompatible; Diclofenac; Drug Carriers; Drug Compounding; Epoxy Compounds; Fibroblasts; Friction; Gamma Rays; Kinetics; Methacrylates; Mice; Microscopy, Electron, Scanning; Polyethylene; Polypropylenes; Solubility; Spectroscopy, Fourier Transform Infrared; Surface Properties; Technology, Pharmaceutical; Temperature; Wettability

An organic polymeric monolithic disk was prepared by situ polymerization of glycidyl methacrylate (GMA) and ethylene dimethacrylate (EDMA) in a binary porogenic solvent consisting 1-propanol and 1,4-butanediol, then modified by a reaction with beta-cyclodextrin (beta-CD). The beta-CD modified disk can be used as a solid substrate and solid phase extraction (SPE) membrane for solid phase extraction-room temperature phosphorescence (SPE-RTP). The room temperature phosphorescence (RTP) behaviors of 14 organic compounds on the beta-CD modified disk were examined. The results indicated that phenanthrene, 7,8-benzoquinoline, carbazole, fluorene, 3-indoleacetic acid and 1-naphthylacetic acid can emit strong RTP, and the limits of detection (LOD) were found to be 6.5 x 10(-10)-3.0 x 10(-9) mol mL(-1). Used as solid phase extraction membrane, the modified disk could selectively enrich compounds with three rings such as phenanthrene, 7,8-benzoquinoline, carbazole and fluorene. After solid phase extraction, LODs of four compounds were decreased to 4.0 x 10(-12)-6.4 x 10(-11) mol mL(-1). The method was applied to the determination of fluorene and phenanthrene in biosamples with satisfactory results.

Topics: beta-Cyclodextrins; Epoxy Compounds; Fluorenes; Luminescent Measurements; Methacrylates; Phenanthrenes; Polymers; Solid Phase Microextraction