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1.
Int J Biol Macromol ; 271(Pt 2): 132711, 2024 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-38815942

RESUMO

Biobased materials are expanding dramatically in various industrial applications due to their unique intrinsic properties. In this study, various chemical functionalization procedures were used to synthesize guar gum, a naturally occurring polysaccharide-based polyurea, and its iodine complexes. Firstly, guar gum was subjected to tosylation reaction using p-toluene sulphonyl chloride to introduce tosyl moieties in the polymer chain with the degree of substitution (DS) ranging between 0.16 and 1.54. Sample having the highest degree of tosyl moiety was further reacted with tris(2-aminoethyl) amine to produce 6-deoxy-6-tris(2-aminoethyl) amine derivative via nucleophilic substitution reaction to impart amino functional groups. The degree of substitution in 6-deoxy-6-tris(2-aminoethyl) amine derivative was found to be 0.59. 6-deoxy-6-tris(2-aminoethyl) amine derivative was reacted with different diisocyanates (Toluene-2,4-diisocyanate (TDI), 1,6-diisocyanatohexane (HMDI)) to produce guar gum based polyurea. Iodine complexes of the resulting polyurea were prepared by reacting with different iodinating agents. Different chemical reactions, formation of polyurea and its iodine complexes were thoroughly analyzed by different analytical techniques such as FT-IR, NMR, elemental analysis, XRD, UV-Vis spectroscopy, and a reaction scheme has been proposed. Morphological and rheological characteristics were analyzed by SEM and viscosity measurement. Thermal analysis was carried out by TGA and DSC studies. Finally, by examining the complex's UV-Vis spectra, the iodine release characteristics from polyurea­iodine complexes were investigated.


Assuntos
Galactanos , Iodo , Mananas , Gomas Vegetais , Polímeros , Gomas Vegetais/química , Galactanos/química , Mananas/química , Iodo/química , Polímeros/química , Polímeros/síntese química , Técnicas de Química Sintética
2.
Biomacromolecules ; 22(9): 3731-3745, 2021 09 13.
Artigo em Inglês | MEDLINE | ID: mdl-34436877

RESUMO

Local delivery of anticancer agents via injectable hydrogels could be a promising method for achieving spatiotemporal control on drug release as well as minimizing the disadvantages related to the systemic mode of drug delivery. Keeping this in mind, we report the development of N,O-carboxymethyl chitosan (N,O-CMCS)-guar gum-based injectable hydrogels for the sustained delivery of anticancer drugs. The hydrogels were synthesized by chemical crosslinking of multialdehyde guar gum (MAGG) and N,O-CMCS through dynamic Schiff base linkages, without requiring any external crosslinker. Fabrication of injectable hydrogels, involving N,O-CMCS and MAGG via Schiff base crosslinking, is being reported for the first time. The hydrogels exhibited pH-responsive swelling behavior and good mechanical properties with a storage modulus of about 1625 Pa. Due to the reversible nature of Schiff base linkages, hydrogels displayed excellent self-healing and thixotropic properties. Doxorubicin (Dox), an anticancer agent, was loaded onto these hydrogels and its release studies were conducted at pH 7.4 (physiological) and pH 5.5 (tumoral). A sustained release of about 67.06% Dox was observed from the hydrogel after 5 days at pH 5.5 and about 32.13% at pH 7.4. The 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide assay on the human embryonic kidney cell line (HEK-293) and the hemolytic assay demonstrated the biocompatible nature of the hydrogels. The Dox-loaded hydrogel exhibited a significant killing effect against breast cancer cells (MCF-7) with a cytotoxicity of about 72.13%. All the data presented support the efficiency of the synthesized N,O-CMCS/MAGG hydrogel as a biomaterial that may find promising applications in anticancer drug delivery.


Assuntos
Antineoplásicos , Quitosana , Antineoplásicos/farmacologia , Liberação Controlada de Fármacos , Galactanos , Células HEK293 , Humanos , Hidrogéis , Concentração de Íons de Hidrogênio , Mananas , Gomas Vegetais
3.
Int J Biol Macromol ; 183: 1495-1504, 2021 Jul 31.
Artigo em Inglês | MEDLINE | ID: mdl-34029580

RESUMO

Guar gum is a neutral, non-ionic polysaccharide that has been extensively utilized in the food industry as a stabilizer, excipients, and emulsifier agent. An oxidized derivative of this edible guar gum was prepared and used as a complexing agent for iron to obtain a polysaccharide-bound iron (II) complex. The degree of oxidation varies between 30.12 and 60.63% with a corresponding aldehyde content (0.59-1.79 mmol/g) and carboxyl contents (0.49-1.62 mmol/g), which were determined by the titrimetry method. Sophisticated spectroscopic techniques characterized all the products. The natural polymer-based hydrophilic and hydrophobic formulations as coating were used for achieving the sustained or prolonged release from the complex tablets. Release studies of the tablets were carried out in different mediums of varying pH. The total iron available from the tablets was compared with that obtained from ferrous fumarate prepared under similar conditions, and the results were found to be comparable. Release results demonstrate the pH-sensitive behaviour of the guar gum-based delivery system towards the controlled release of iron. Antianemic effect of new functionalized guar gum iron complexes was investigated on male albino rats. The complexes may exhibit the potential to recover the hematological index of the albino rats with some positive effects on improving rat's growth with iron deficiency anaemia.


Assuntos
Anemia/tratamento farmacológico , Galactanos/química , Ferro/química , Mananas/química , Gomas Vegetais/química , Anemia Ferropriva/tratamento farmacológico , Animais , Concentração de Íons de Hidrogênio , Interações Hidrofóbicas e Hidrofílicas , Masculino , Ratos , Solubilidade , Comprimidos/química , Comprimidos/uso terapêutico
4.
ACS Appl Bio Mater ; 3(12): 8460-8470, 2020 Dec 21.
Artigo em Inglês | MEDLINE | ID: mdl-35019617

RESUMO

Gum arabic with multialdehyde groups (GAMA) was synthesized and utilized as a naturally derived macromolecular and nontoxic cross-linker to develop biocompatible and smart succinic anhydride-modified chitosan (SCS)-based injectable hydrogels for the first time. Aqueous solutions of GAMA and SCS were mixed at 37 °C to obtain hydrogels through pH-responsive, dynamic, and biodegradable Schiff base linkages. The effect of concentration of GAMA on hydrogel stiffness, swelling, morphology, and drug release behavior was investigated. These hydrogels exhibited outstanding self-healing and mechanical properties. Nanocurcumin as a chemotherapeutic agent was synthesized and loaded into these hydrogels for release studies carried out at pH 7.4 and 5.5. MTT assay revealed that these hydrogels are nontoxic to human embryonic kidney cell line (HEK-293). Loaded hydrogels demonstrated significant cytotoxicity against breast cancer cell line (MCF-7). Thus, the present strategy may find promising application for controlled delivery of anticancer drugs for treating locally accessible cancers.

5.
Int J Biol Macromol ; 153: 1147-1156, 2020 Jun 15.
Artigo em Inglês | MEDLINE | ID: mdl-31760005

RESUMO

Folic acid a synthetic form of folate, is the oxidized form of folate which acts as a coenzyme in one carbon transfer reactions required in the biosynthesis of DNA and RNA and its deficiency could be related to diseases such as neural tube defects, Alzheimer's disease, pregnancy complications and cancer. Inulin is a polydisperse polysaccharide comprising mostly of fructosyl fructose units. An oxidized derivative of this inulin was prepared and used as a complexing agent for folic acid to obtain a polysaccharide bound folic acid conjugate. The aldehyde content and degree of oxidation of the oxidized inulin were determined by acid-base titrations. All the products were characterized by sophisticated spectroscopic and thermal methods of analysis. Release studies of folic acid from conjugates were carried out in different pH media and the results demonstrate the pH-sensitive behavior of the inulin-based delivery system towards the controlled release of folic acid.


Assuntos
Portadores de Fármacos/química , Liberação Controlada de Fármacos , Ácido Fólico/química , Inulina/química , Aldeídos/química , Aminação , Peso Molecular , Oxirredução
6.
ACS Omega ; 4(14): 16026-16036, 2019 Oct 01.
Artigo em Inglês | MEDLINE | ID: mdl-31592147

RESUMO

The chemically oxidized gum arabic was prepared and used as a naturally derived nontoxic and pH-responsive cross-linker to develop smart polyvinyl alcohol (PVA)-based hydrogels for the first time. The formulated hydrogels exhibited high mechanical properties, good porosity, and pH sensitivity, which facilitated their application as promising biomaterials for sustained delivery of folic acid. Further, the synthesized cross-linked PVA hydrogels displayed no cytotoxicity toward the human embryonic kidney cell line and exhibited higher blood compatibility. The hydrolytic degradation study confirmed their biodegradable nature. While the sustained delivery along with photoprotective properties of these hydrogels confirmed their multifunctional characteristics, these results suggest that these hydrogels may act as an efficient photoprotective material and find their application in the field of drug delivery.

7.
Int J Biol Macromol ; 137: 853-869, 2019 Sep 15.
Artigo em Inglês | MEDLINE | ID: mdl-31284008

RESUMO

Modification of Hyaluronic acid (HA) with Sodium metaperiodate (NaIO4) results in the formation of oxidized HA (OHA). OHA containing multiple aldehyde groups can easily react with the materials having amino functionality via formation of Schiff base linkage, resulting in the formation of OHA based hydrogel scaffolds. These hydrogels have recently attracted considerable attention as scaffolds for tissue engineering (TE) applications. Thus, the aim of the present review is to give an overview on OHA based hydrogels as scaffolds and their potential application in the field of TE along with the method of synthesis and important properties of OHA.


Assuntos
Ácido Hialurônico/química , Hidrogéis/química , Ácido Periódico/química , Engenharia Tecidual/métodos , Alicerces Teciduais/química , Animais , Humanos , Oxirredução
8.
Carbohydr Polym ; 180: 337-347, 2018 Jan 15.
Artigo em Inglês | MEDLINE | ID: mdl-29103513

RESUMO

Gum arabic, a plant polysaccharide was oxidized with periodate to produce aldehyde groups by the cleavage of diols present in the sugar units. The oxidized gum was then iodinated with iodine monochloride (ICl) and the interaction between electrophilic iodine, I+ and reactive carbonyl groups of the modified gum was studied.Results of titrimetric estimation performed to determine the extent of oxidation and aldehyde content in the oxidized gum showed that degree of oxidation ranged between 19.68-50.19% which was observed to increase with periodate concentration; the corresponding aldehyde content was calculated to be 5.15-40.42%. Different strengths of ICl were used to iodinate the oxidized gum and the iodine content of the complexes varied from 6.11-11.72% as determined by iodometric titration. Structure elucidation of the iodine complexes conclusively established the attachment of ICl molecules to CHO groups. A reaction scheme has been proposed suggesting an electrophilic addition of the reagent to the aldehyde groups, a mechanism that was also supported by iodide ion release studies.

9.
Carbohydr Polym ; 129: 224-31, 2015 Sep 20.
Artigo em Inglês | MEDLINE | ID: mdl-26050909

RESUMO

Acetylated gum Arabic (AGA) derivatives with different degrees of substitution (DS 0.97-2.74) were synthesized using acetyl chloride and a base under varying reaction conditions. The AGA derivatives were obtained in the form of microspheres and thereafter stable iodine products were prepared by doping the microspheres with an iodinating agent, iodine monochloride (ICl). The reaction between electrophilic iodine and polar carbonyl groups was studied by FT-IR, (1)H-NMR, and UV-VIS spectroscopies. The products were also characterized by DSC, TGA and SEM studies. The incorporated iodine was released in aqueous medium as iodide ions (I(-)). A reaction scheme has been proposed for the iodination and de-iodination of the gum derivatives. This work suggests that the iodine derivatives of modified gum Arabic could be used as a source of iodide ions which is the nutritional form of iodine.


Assuntos
Goma Arábica/química , Iodo/química , Microesferas , Acetilação , Varredura Diferencial de Calorimetria , Halogenação , Microscopia Eletrônica de Varredura , Espectroscopia de Prótons por Ressonância Magnética , Espectrofotometria Ultravioleta , Espectroscopia de Infravermelho com Transformada de Fourier , Temperatura , Termogravimetria
10.
Carbohydr Polym ; 92(1): 497-502, 2013 Jan 30.
Artigo em Inglês | MEDLINE | ID: mdl-23218326

RESUMO

To overcome the drawbacks associated with iodine e.g. insolubility in water, etc., it has been complexed with polymers that have the ability to bind it. In this study, gum arabic (GA), a natural gum was functionalized to introduce new reactive groups that can easily interact with small molecules followed by iodination in ethanol solution to prepare an iodine complex. The samples were characterized by FTIR, thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC). The synthesized iodine complex was found reddish-brown in colour and stable at room temperature. The interaction of free available iodine with functionalized GA was also studied and established by UV-vis spectrophotometer. The amount of iodine released in water was measured by iodometric titration method and its value compared with the available iodine complex, polyvinylpyrrolidone-iodine complex. The antimicrobial activity of iodine complex was tested against Escherichia coli (Gram negative bacteria) and found to be effective against it.


Assuntos
Goma Arábica , Compostos de Iodo , Iodo/química , Anti-Infecciosos/síntese química , Anti-Infecciosos/química , Anti-Infecciosos/farmacologia , Escherichia coli/efeitos dos fármacos , Etanol/química , Goma Arábica/síntese química , Goma Arábica/química , Compostos de Iodo/síntese química , Compostos de Iodo/química , Compostos de Iodo/farmacologia , Solubilidade , Água/química
11.
J Nanosci Nanotechnol ; 11(11): 10164-72, 2011 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-22413360

RESUMO

One-dimensional (1D) nanostructured polyindole (Nano-Pind) was synthesized with 10 minutes (Pind-10 m) and 24 hours (Pind-24 h) of polymerization time using a facile chemical oxidative polymerization method. The obtained Nano-Pinds were explored to study the differences in their structural, optical, spectral and conducting properties with regard to the variation in polymerization duration. Scanning Electron Microscopy (SEM) and Transmission Electron Microscopy (TEM) reveal formation of long and smooth surfaced 1D nanostructures of Pind with diameter of approximately 25-125 nm and lengths of several microns. Structural chemical analysis of the Nano-Pinds conducted by Fourier Transform Infrared (FTIR), Nuclear Magnetic Resonance (NMR) and Fluorescence spectroscopic measurements support their formations, thereby indicating Pind-24 h to exhibit sharper and far better resolved spectral profile than that of Pind-10 m. The Nano-Pinds exhibit good blue-light emitting property, and improved Electrical Conductivity (EC) than earlier reported globular Pinds, suggesting their potential applications in nanotechnology, especially in the field of optoelectronics. To the best of our knowledge, this is the first report on 1D nanostructures of Pind.

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