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1.
M. Yu. Gorshkova I. F. Volkova S. G. Alekseeva N. N. Molotkova E. E. Skorikova V. A. Izumrudov 《Polymer Science Series A》2011,53(1):57-66
The selective alkylation of primary amino groups of polysaccharide is conducted through the interaction of chitosan with glycidyltrimethylammonium
chloride with introduction of the quaternized amino group into every alkylated unit, thereby ensuring a positive charge and
solubility of the polymer over the entire pH range. The structure of the modified chitosan is studied via FTIR spectroscopy
and 13C and 1H NMR measurements. On the basis of the potentiometric titration of solutions of the parent polysaccharide, its modified derivative,
and their mixtures with the polystyrenesulfonate anion, as well as ζ-potential measurements and turbidimetric titration of
polymer mixtures, it is demonstrated that the secondary amino group of the complexed modified chitosan can be protonated in
weakly acidic solutions. This behavior is of particular importance for the design of biocompatible and biodegradable vehicles
suitable for the delivery of genetic material and drugs to cells. 相似文献
2.
Mariamne Dehonor-Gómez Margarita Hernández-Esparza F. Alberto Ruiz-Treviño Roberto Contreras-Reyes 《Macromolecular Symposia》2003,197(1):277-288
This work presents the results of the modification of lateral groups of chitosan (2-amino-2-desoxy-β-D-glucose) by the reaction with different amino acids (glycine, L-lysine, -glutamic acid and L-isoleucine) under acid catalysis. The Cu2+ adsorption capacity of pure chitosan and of the chemically modified chitosans were also evaluated. The modification reaction favored the amide formation of the C-2 carbon of the glycoside ring under the adopted reaction conditions: reaction time and temperature and using sulfuric acid as a catalyst. The Cu2+ adsorption kinetics and equilibrium response using pure chitosan and the chemically modified chitosans as adsorbents showes that the adsorption capacity of equilibrium depended on the initial ion concentration. The response of each adsorbent gave good correlation with Langmuir's isotherm model. The following maximum adsorption capacity constants were obtained: 172.4 mg/g for chitosan and 69.9, 34.4, and 26.7 mg/g for modified chitosan with glycine, L-glutamic acid, and L-lysine, respectively. The adsorptive capacity seems to be dependent on the length and complexity of the added group. 相似文献
3.
A new low-molecular-weight antibacterial dye was obtained by reaction of Reactive Blue 19 and chitosan previously hydrolyzed with H2O2. The compounds were characterized by Fourier-transform infrared spectroscopy, 13C solid-state nuclear magnetic resonance, X-ray photoelectron spectroscopy, X-ray diffraction analysis, and antibacterial, solubility, and dyeing performance tests including color difference and fastness. The results show that chitosan dyes were generated with covalent bonds between carbon and nitrogen atoms via reaction of alkene group of dye and primary amine group of chitosan. According to solubility tests, the solubility of the chitosan dye was controlled by the molecular weight of chitosan. In addition, compared with Reactive Blue 19, the antibacterial property of the chitosan dye was increased against both Gram-positive (Staphylococcus aureus) and Gram-negative (Escherichia coli) bacteria. Besides, chitosan dye demonstrated better lightfastness and waterfastness than the original dye. Therefore, chitosan dye provides a new perspective for improving decorative and antimicrobial properties of wood products. 相似文献
4.
Chitosan is a natural based polymer obtained by alkaline deacetylation of chitin, exhibiting excellent properties such as non‐toxicity, biocompatibility and biodegradability. N‐Methylenephenyl phosphonic chitosan (NMPPC) is synthesized from chitosan by reacting with phenyl phosphonic acid using formaldehyde. The NMPPC was characterized by FTIR, 31P‐NMR, X‐ray diffraction, scanning electron microscopy, thermogravimeteric analysis and solubility studies. A significant decrease of molecular weight was observed in the NMPPC. The TGA studies suggested that NMPPC has less thermal stability than chitosan. The X‐ray diffraction analysis showed that NMPPC was amorphous in nature. The solubility property of the polymer was improved after the incorporation of a phenyl phosphonic group. 相似文献
5.
Maumita Das Mukherjee Pratima R. Solanki Gajjala Sumana Takaaki Manaka Mitsumasa Iwamoto Bansi D. Malhotra 《Applied biochemistry and biotechnology》2014,174(3):1201-1213
A self-assembled monolayer (SAM) of thiol modified chitosan (SH-CHIT), with thioglycolic acid (TGA) as a modifier to bestow thiol groups, has been prepared onto gold (Au)-coated glass plates for fabrication of the nucleic acid biosensor. The chemical modification of CHIT via TGA has been evidenced by Fourier transform infrared spectroscopy (FT-IR) studies, and the biocompatibility studies reveal that CHIT retains its biocompatible nature after chemical modification. The electrochemical studies conducted onto SH-CHIT/Au electrode reveal that thiol modification in CHIT amino end enhances the electrochemical behavior indicating that it may be attributed to delocalization of electrons in CHIT skeleton that participates in the resonance process. The carboxyl group modified end of DNA probe has been immobilized onto SH-CHIT/Au electrode using N-ethyl-N′-(3-dimethylaminopropyl)carbodimide (EDC) and N-hydroxysuccinimide (NHS) chemistry for detection of complementary, one-base mismatch and non-complementary sequence using electrochemical and optical studies for Mycobacterium tuberculosis detection. It has been found that DNA-SH-CHIT/Au bioelectrode can specifically detect 0.01 μM of target DNA concentration with sensitivity of 1.69?×?10?6 A μM?1. 相似文献
6.
Synthesis and antibacterial activity of methylated N-(4-N,N-dimethylaminocinnamyl) chitosan chloride
The methylated chitosan containing different aromatic moieties were synthesized by two steps, the reductive amination and the methylation. The chemical structures of all methylated derivatives, methylated N-(4-N,N-dimethylaminocinnamyl) chitosan chloride (MDMCMCh), methylated N-(4-pyridylmethyl) chitosan chloride (MPyMeCh), and N,N,N-trimethyl chitosan chloride (TMChC) were characterized by ATR-FTIR and 1H NMR spectroscopy. The molecular weights of the methylated chitosan derivatives were determined by gel permeation chromatography. The results revealed that the molecular weights of chitosan and N-aryl chitosan derivatives could be reduced by the methylation process. The degree of N-substitution (DS) and the degree of quaternization (DQ) were calculated by 1H NMR ranged from 50% to 76%, and 28% to 82%, respectively. The water solubility of the methylated chitosan derivatives decreased with increasing concentration and pH. The antibacterial studies of these methylated chitosan derivatives were carried out by using minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) methods against Escherichia coli ATCC 25922 (Gram-negative) and Staphylococcus aureus ATCC 6538 (Gram-positive) bacteria. It was found that the MDMCMCh showed higher antibacterial activity than TMChC while MPyMeCh exhibited reduced antibacterial activity against both bacteria at the same DQ level. In comparison to each of the chemical structure, it was found that the antibacterial activity was not only dependent on the DQ but it was also dependent on the positively charged location and the molecular weight. 相似文献
7.
8.
In this work, n-alkyl chitosan (N-CTS) was obtained by alkylation modification of chitosan with n-butylaldehyde using Schiff alkali method. The etherifying agent 3-chloro-2-hydroxypropyl triethylammonium chloride (CHPTAC-ethyl) was synthesized from triethylamine and epichlorohydrin. The N-CTS and CHPTAC-ethyl were etherized to finally synthesize n-alkyl quaternary ammonium chitosan (N-CCTS). Scanning electron microscope, X-ray diffractometer, Fourier transform infrared, X-ray photoelectron spectroscopy, and 13CNMR were used to characterize the surface morphology and chemical structure. Viscosity method and spectrophotometry were used to determine its physical and chemical properties. The etherification reaction mechanism was studied systematically and the influence of reaction conditions on the degree of substitution and solubility of N-CCTS was investigated. The minimum inhibitory concentration (MIC) of N-CCTS against Escherichia coli (E. coli) and Staphylococcus aureus (S. aureus) was both 0.15 g/L, which was superior to the MIC value of natural chitosan. N-CCTS was used to finish rabbit hair fabric with citric acid as cross-linking agent and sodium hypophosphite as catalyst. The antibacterial and washing resistance of the product were investigated. After 25 times of washing, the antibacterial rate of N-CCTS against E. coli and S. aureus remained stable at about 90%, and the antibacterial rate was higher than that of N-CTS and natural chitosan, and it was a kind of natural polymer long-acting antibacterial finishing agent for rabbit hair fabric. 相似文献
9.
《Analytical letters》2012,45(10):1853-1863
Abstract NiO nanoparticles (NiO NPs) were prepared with chemical precipitation method and modified on the surface of vaseline‐impregnated graphite electrode with chitosan. It was found that, based on the catalysis of the NiO NPs for the chemiluminescent reaction of the ECL process, the enhancing effect of isoniazid on the weak electrogenerated chemiluminescence (ECL) signal of luminol at a NiO NPs‐chitosan modified electrode was stronger than that at a bare graphite electrode. Under the optimum experimental conditions, the relative ECL intensity was linear with isoniazid concentration over the range 3.0×10?10~1.0×10?6 g/ml at the NiO NPs‐chitosan modified electrode with a detection limit of 1.0×10?10 g/ml. 相似文献
10.
Ravindra Tewari 《International journal of quantum chemistry》1988,34(1):37-46
Conformational preferences of model modified nucleic acid base N6-(N-alanylcarbonyl) adenine, ac6Ade, have been investigated using the quantum chemical PCILO (perturbative configuration interaction using localized orbitals) method. The multidimensional conformational space has been searched using selected grid points formed by combining the various torsion angles that take favored values derived from energy variation with respect to each torsion angle individually. The preferred molecular structure is stabilized by an intramolecular hydrogen bond from N(11)H of the amino acid to N(1) of the adenine. The observed crystal structure conformations for the naturally occurring, anticodon adjacent, threonyl analogs, tc6Ade, correspond to the predicted most stable conformation for the model modified base ac6Ade. Three stable, low energy conformations differing in the orientations of the carboxyl group and the amino acid side chain are predicted within 1 kcal/mol of the most stable structure. The possible bifurcated hydrogen bonding of N(11)H with N(1) and either of the carboxyl oxygens is of minor significance. The indicated orientational flexibility for the carboxyl group and the amino acid side chain may enable convenient probing of the molecular environment, in the vicinity of the anticodon in tRNA, by the amino acid substituent, with only modest changes in energy stabilization. 相似文献
11.
Sharmin RAHMAN Kazi Hanium MARIA Mohammad Saif ISHTIAQUE Arijun NAHAR Harinarayan DAS Sheikh Manjura HOQUE 《Turkish Journal of Chemistry》2020,44(4):884
Artificially fabricated hydroxyapatite (HAP) shows excellent biocompatibility with various kinds of cells and tissues which makes it an ideal candidate for a bone substitute material. In this study, hydroxyapatite nanoparticles have been prepared by using the wet chemical precipitation method using calcium nitrate tetra-hydrate [Ca(NO3)2.4H2O] and di-ammonium hydrogen phosphate [(NH4)2 HPO4] as precursors. The composite scaffolds have been prepared by a freeze-drying method with hydroxyapatite, chitosan, and gelatin which form a 3D network of interconnected pores. Glutaraldehyde solution has been used in the scaffolds to crosslink the amino groups (|NH2) of gelatin with the aldehyde groups (|CHO) of chitosan. The X-ray diffraction (XRD) performed on different scaffolds indicates that the incorporation of a certain amount of hydroxyapatite has no influence on the chitosan/gelatin network and at the same time, the organic matrix does not affect the crystallinity of hydroxyapatite. Transmission electron microscope (TEM) images show the needle-like crystal structure of hydroxyapatite nanoparticle. Scanning Electron Microscope (SEM) analysis shows an interconnected porous network in the scaffold where HAP nanoparticles are found to be dispersed in the biopolymer matrix. Fourier transforms infrared spectroscopy (FTIR) confirms the presence of hydroxyl group (OH-) , phosphate group (PO3-4) , carbonate group (CO2-3) , imine group (C=N), etc. TGA reveals the thermal stability of the scaffolds. The cytotoxicity of the scaffolds is examined qualitatively by VERO (animal cell) cell and quantitatively by MTTassay. The MTT-assay suggests keeping the weight percentage of glutaraldehyde solution lower than 0.2%. The result found from this study demonstrated that a proper bone replacing scaffold can be made up by controlling the amount of hydroxyapatite, gelatin, and chitosan which will be biocompatible, biodegradable, and biofriendly for any living organism. 相似文献
12.
In this work, the modified Wilson model was used to obtain the activity coefficients of amino acids and simple peptides in non-electrolyte aqueous solutions. The Wilson model was modified using the new local mole fraction proposed by Zhao et al. and non-random case for the reference state. The binary interaction parameters (BIP) of the modified Wilson model for amino acid–water pairs were obtained using the experimental data of the activity coefficients for amino acids available in the literature. The modified Wilson model was also used to correlate the solubility of amino acids in water and the values of Δh/R, Δs/R, and Δg/R of the solutions studied were reported. The results obtained showed that the modified Wilson model can accurately correlate the activity coefficients as well as the solubility of amino acids and simple peptides in aqueous solutions. Also the modified Wilson model was coupled with the Pazuki–Rohani model to correlate the mean ionic activity coefficients of electrolytes in aqueous amino acid solutions. The results showed that the proposed model can accurately correlate the activity coefficients of the electrolytes in aqueous amino acid solution. 相似文献
13.
The alkylation of primary amino groups of chitosan with glycidyltrimethylammonium chloride yields the modified cationic polysaccharide
that carries, in practically every deacetylated unit, a secondary amino group and a quaternized amino group that provide the
solubility of the polymer over the whole range of pH values. The mixing of solutions of modified chitosan and nucleic acid
in neutral solutions at various ratios gives soluble DNA-containing polyelectrolyte complexes (polyplexes) that preserve stability
under physiological conditions. The effects of the pH, ionic strength, and charge-to-charge ratio of polymer components on
the boundaries of existence of soluble polyplexes both negatively and positively charged are elucidated. The collected experimental
data may serve as a basis for designing biocompatible and biodegradable means for the delivery of genetic material and drugs
to living cells. 相似文献
14.
IR study on chitosan oxidation with sodium chlorite 总被引:1,自引:0,他引:1
K. Yu. Murinov A. R. Kuramshina R. A. Khisamutdinov Yu. I. Murinov N. N. Kabal’nova 《Russian Journal of General Chemistry》2010,80(1):23-26
Oxidation of chitosan with sodium chlorite was studied by IR spectroscopy. The process was shown to involve oxidation of the
primary hydroxy group on C6 to carboxy group and subsequent oxidative decomposition of the polysaccharide. The degree of carboxylation of the oxidized
chitosan was determined by potentiometric titration. The possibility for formation of a covalent bond between the amino nitrogen
atom and carbon atom of the carboxy group in the oxidized chitosan was considered. 相似文献
15.
Regioselectively Modified Cellulose and Chitosan Derivatives for Mono- and Multilayer Surface Coatings of Hemocompatible Biomaterials 总被引:2,自引:0,他引:2
In this study different synthetic strategies were developed and applied to introduce solely or in combination heparin/heparansulfate-like functional groups such as N-sulfo, O-sulfo, N-acetyl, and N-carboxymethyl groups into chitosan and cellulose with highest possible regioselectivity and completeness and defined distribution along the polymer chain. Completely substituted 6-amino-6-deoxycellulose and related derivatives were prepared from tosylcellulose (DS 2.02; C6 1.0) by nucleophilic substitution with azido groups only in the 6-position at 50 °C with subsequent reduction to amino groups and completely removing tosyl groups in the 2,3-position. 2,6-Di-O-sulfocellulose was prepared using the reactivity difference between C-2, C-6 and C-3 of cellulose. The reactivity difference between amino groups and hydroxyl groups was used to prepare various N-substituted derivatives. Partially 2,6-di-O-sulfated cellulose was obtained from trimethylsilylcellulose by the insertion of sulfurtrioxide into the Si–O ether linkage. Partially 3-O-sulfocellulose was synthesized by protecting C-2 and C-6 with trifluoroacetyl groups. A copper–chitosan complex was used to synthesize 6-O-sulfochitosan with a DS of 1.0 at C-6 and various partially 6-O-desulfonated products are possible. Using the phthalimido group to increase the solubility of chitosan in DMF, the regioselectivity of 3-O-sulfo groups was improved by regioselective 6-O-desulfonation of nearly complete 3,6-O-disulfochitosan. The platelet adhesion properties of immobilized regioselectively modified water-soluble derivatives on membranes have been tested in vitro. Some regioselectively modified chitosan and cellulose derivatives are potential candidates for the surface coatings of biomaterials if the regioselective reactions are somewhat further optimized. 相似文献
16.
V. A. Izumrudov I. F. Volkova E. S. Grigoryan M. Yu. Gorshkova 《Polymer Science Series A》2011,53(4):281-288
A modified polysaccharide that, in each deacetylated unit, carries a functional secondary amino group and a quaternized amino
group that provides a positive charge and solubility to the polymer throughout the pH range is prepared by the alkylation
of primary amino groups of chitosan with glycidyltrimethylammonium chloride. The mixing of modified chitosan solutions with
solutions of polystyrenesulfonate or polymethacrylate anions in neutral solutions gives rise to negatively charged nonstoichiometric
polyelectrolyte complexes soluble and stable under physiological conditions. The effects of pH, ionic strength, the degree
of polymerization, the nature of the lyophilizing polyanion, and the charge-to-charge ratio of components on the boundaries
of existence of soluble complexes are ascertained. The collected experimental data may serve as a basis for designing biocompatible
and biodegradable means useful for the delivery of genetic material and drugs to living cells. 相似文献
17.
In the present paper, the depolymerization of chitosan was carried out by the ultraviolet-irradiated oxygen treatment. Influence of reaction conditions on depolymerization of chitosan was investigated. The chemical structure of the depolymerized chitosan was characterized by FT-IR and 13C NMR spectra. The FT-IR and 13C NMR spectra suggested that there was no obvious modification of chemical structure of the depolymerized chitosan. The X-ray diffraction analysis showed that crystalline structure of chitosan can be destroyed by ultraviolet-irradiated oxygen. The use of depolymerization of chitosan by ultraviolet-irradiated oxygen treatment can be a convenient, timesaving, and cost-efficient method for replacing the expensive and time-consuming enzymatic or chemical methods that are currently used to depolymerize chitosan. 相似文献
18.
Hao Feng Chang‐Ming Dong 《Journal of polymer science. Part A, Polymer chemistry》2006,44(18):5353-5361
Chitosan‐graft‐poly(ϵ‐caprolactone) was prepared via the ring‐opening graft polymerization of ϵ‐caprolactone (CL) through chitosan with 4‐dimethylaminopyridine as a catalyst and water as a swelling agent. The graft content of PCL within the graft copolymer was adjusted by the feed ratio of CL to chitosan, and the highest grafting concentration of PCL was up to about 400%. Fourier transform infrared, 1H NMR, and two‐dimensional heteronuclear single quantum coherence analyses indicated that the amino group (NH2 CH‐2) of chitosan initiated the graft polymerization of CL through the backbone of chitosan, and the hydroxyl group (HO CH2–6) of chitosan did not participate in initiating the graft polymerization. The percentage of amino groups initiating the graft polymerization decreased with an increasing molar ratio of CL to chitosan in the feed, and this was attributed to the fact that the graft polymerization system increasingly became heterogeneous with an increasing feed ratio of CL to chitosan. The physical properties of the graft copolymers were characterized by thermogravimetric analysis and wide‐angle X‐ray diffraction, respectively. These suggested that the introduction of PCL grafts through the chitosan backbone would to some extent destroy the crystalline structure of chitosan, and the PCL grafts existed in an amorphous structure. © 2006 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 44: 5353–5361, 2006 相似文献
19.
Fereshteh Chekin Jahan‐Bakhsh Raoof Samira Bagheri Sharifah Bee Abd Hamid 《中国化学会会志》2012,59(11):1461-1467
We report a simple and effective strategy for fabrication of the nanocomposite containing chitosan (CS) and multiwall carbon nanotube (MWNT) coated on a glassy carbon electrode (GCE). The characterization of the modified electrode (CS‐MWNT/GC) was carried out using scanning electron microscopy (SEM) and UV–vis absorption spectroscopy. The electrochemical behavior of CS‐MWNT/GC electrode was investigated and compared with the electrochemical behavior of chitosan modified GC (CS/GC), multiwalled carbon nanotube modified GC (MWNT/GC) and unmodified GC using cyclic voltammetry (CV) and electron impedance spectroscopy (EIS). The chitosan films are electrochemically inactive; similar background charging currents are observed at bare GC. The chitosan films are permeable to anionic Fe(CN)63?/4? (FC) redox couple. Electrochemical parameters, including apparent diffusion coefficient for the Fe(CN)63?/4? redox probe at FC/CS‐MWNT/GC electrode is comparable to values reported for cast chitosan films. This modified electrode also showed electrocatalytic effect for the simultaneous determination of D‐penicillamine (D‐PA) and tryptophan (Trp). The detection limit of 0.9 μM and 4.0 μM for D‐PA and Trp, respectively, makes this nanocomposite very suitable for determination of them with good sensitivity. 相似文献
20.
Kaushal Kumar Mahato Shivesh Sabbarwal Nira Misra 《International Journal of Polymer Analysis and Characterization》2020,25(5):353-361
Abstract Hydrogel composites from polyvinyl alcohol and chitosan have been developed by various researchers as a function of their composition for various medical applications. Although, the solubility of chitosan in acidic solvents may limit its wide bioengineering applications. In this article, we demonstrate that polyvinyl alcohol-chitosan oligosaccharide (water soluble) to develop cross-linked hydrogel network using chemical cross linker. X ray diffraction, Fourier transform infrared spectroscopy, and wettability study of these hydrogels were also performed. Lomefloxacin drug was loaded into the hydrogels and its release profile was studied. 相似文献