Study of the Chemical Structure of Dialdehyde Carboxymethyl Cellulose Produced by Periodate Oxidation under Different Conditions

Dyatlov, V. A.; Gumnikova, V. I.; Grebeneva, T. A.; Kruppa, I. S.; Rustamov, I. R.; Kireev, Vjacheslav; Maleev, Victor I.

doi:10.1177/0307174x1504200404

Cited by 6 publications

(5 citation statements)

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“…Still, a characteristic signal of carbonyl groups in ketones appears at 217.77 ppm. There is a possibility that the hydrated form of the aldehyde groups may appear in an aqueous solution [ 50 , 51 ], but the characteristic signals were not found in the spectrum of CMCOx dissolved in deuterated water. In the spectrum of CMCOx dissolved in DMSO, there are signals of the aldehyde groups at 204.03 ppm, 200.29 ppm, 197.78 ppm, and 194.06 ppm.…”

Section: Resultsmentioning

confidence: 99%

“…CMC oxidation determines numerous signals in the region of 80–105 ppm. The signals are attributed to carbon atoms from C-O-C groups of hemiacetals [ 50 ]. The results obtained are consistent with those reported by other studies [ 50 , 51 , 52 ].…”

Section: Resultsmentioning

confidence: 99%

“…In some papers, it is estimated that the oxidation process retardation can be caused by the hydrogen bond that is formed between the carboxyl group of one polymer chain and the hydroxyl group from the C3 atom of neighboring chains. The oxidation degree can also be adjusted by changing the ratio between the reactants [ 50 ].…”

Section: Resultsmentioning

confidence: 99%

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Hydrogel Films Based on Chitosan and Oxidized Carboxymethylcellulose Optimized for the Controlled Release of Curcumin with Applications in Treating Dermatological Conditions

et al. 2021

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Cross-linked chitosan (CS) films with aldehyde groups obtained by oxidation of carboxymethyl cellulose (CMC) with NaIO4 were prepared using different molar ratios between the CHO groups from oxidized carboxymethyl cellulose (CMCOx) and NH2 groups from CS (from 0.25:1 to 2:1). Fourier-transform infrared (FTIR) and nuclear magnetic resonance (NMR) spectroscopy demonstrated the aldehyde groups’ presence in the CMCOx. The maximum oxidation degree was 22.9%. In the hydrogel, the amino groups’ conversion index value increased when the -CHO/-NH2 molar ratio, cross-linking temperature, and time increased, while the swelling degree values decreased. The hydrogel films were characterized by scanning electron microscopy (SEM) and FTIR analysis. The curcumin encapsulation efficiency decreases from 56.74% to 16.88% when the cross-linking degree increases. The immobilized curcumin release efficiency (REf%) and skin membrane permeability were evaluated in vitro in two different pH solutions using a Franz diffusion cell, and it was found to decrease when the molar ratio -CH=O/NH2 increases. The curcumin REf% in the receptor compartment was higher at pH = 7.4 (18%- for the sample with a molar ratio of 0.25:1) than at pH = 5.5 (16.5%). The curcumin absorption in the skin membrane at pH = 5.5 (47%) was more intense than at pH = 7.4 (8.6%). The curcumin-loaded films’ antioxidant activity was improved due to the CS presence.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Hydrogel Films Based on Chitosan and Oxidized Carboxymethylcellulose Optimized for the Controlled Release of Curcumin with Applications in Treating Dermatological Conditions

et al. 2021

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“…In figure 1, a sharp peak at 1738.37cm -1 is due to C=O Stretching vibration of carboxylic acid and ester component of hemicelluloses in untreated BNHF. In treated BNHF the peak 1738.37cm -1 is corresponding to C=O Stretching vibration of hemicelluloses disappeared due to the removal of lignin and hemicelluloses (14). Figure 3.…”

Section: Ftir Analysis:-mentioning

confidence: 97%

Impact on Morphological, Physicomechanical and Thermal Properties of Polypropylene Composites Reinforced With Chemically Modified Betel Nut Husk Fiber.

Sultana¹

2019

IJAR

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“…Chemical modification of gossypol was studied several times with respect to toxicity reduction and activity retention. Substantial progress was made by immobilizing it on polysaccharide substrates that were chemically modified via periodate oxidation [6,7]. However, the chemical structures of these compounds are still little studied.…”

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Covalent Linkage of Gossypol and Dialdehyde Dextran

et al. 2016

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The structures of the products from addition of gossypol to dialdehyde dextran were studied using 13 C NMR and MALDI-TOF mass spectrometry of model compounds and computer modelling. The model reaction was highly stereo-and regiospecific owing to steric hindrance to adding two E-glucose molecules to one gossypol molecule. The main binding sites to the oxidized polysaccharide were determined.Gossypol (1,6,7-trihydroxy-3-methyl-5-isopropyl-8-naphthaldehyde) is a natural polyphenol and cotton toxin with experimentally confirmed contraceptive, antioxidant, antitrypanosomal, antimicrobial, and other activities [1][2][3][4]. Derivatives with antiviral and antitumor activity are most interesting [4,5]. Chemical modification of gossypol was studied several times with respect to toxicity reduction and activity retention. Substantial progress was made by immobilizing it on polysaccharide substrates that were chemically modified via periodate oxidation [6,7]. However, the chemical structures of these compounds are still little studied.Herein, the chemical structures of the addition products of gossypol to different reactive sites on the dialdehyde dextran macromolecule were studied. The reaction of gossypol with glucose in aqueous and alcoholic solutions was used as a model. Boric acid was used as an orienting agent that could change the course of the condensation of gossypol aldehydes and polysaccharide hydroxyls.Keto-enol tautomerism is typical of gossypol. It can adopt three different forms (aldehyde, lactol, ketol) depending on the solvent and acidity [1].The aldehyde form dominates in the solid state and non-polar solvents. The ketol tautomer occurs in alkaline aqueous solutions. Gossypol lactol and aldehyde forms are in equilibrium in strongly polar solvents. Only two of the three forms (aldehyde and ketol) can react with polysaccharides to give products with different chemical structures [1][2][3][4][5][8][9][10][11][12][13][14].Dextran is a natural polysaccharide that is widely used as a polymer substrate for physiologically active compounds and is suitable for parenteral administration. It is chemically inert to proteins and peptides. Therefore, it is often functionalized using Malaprade periodate oxidation to give dialdehyde dextran. As it turned out, the oxidized units did not contain free aldehydes [6, 7] but were closed into cyclic hemiacetals (1) in both solutions and the solid state.

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Study of the Chemical Structure of Dialdehyde Carboxymethyl Cellulose Produced by Periodate Oxidation under Different Conditions

Cited by 6 publications

References 4 publications

Hydrogel Films Based on Chitosan and Oxidized Carboxymethylcellulose Optimized for the Controlled Release of Curcumin with Applications in Treating Dermatological Conditions

Hydrogel Films Based on Chitosan and Oxidized Carboxymethylcellulose Optimized for the Controlled Release of Curcumin with Applications in Treating Dermatological Conditions

Impact on Morphological, Physicomechanical and Thermal Properties of Polypropylene Composites Reinforced With Chemically Modified Betel Nut Husk Fiber.

Covalent Linkage of Gossypol and Dialdehyde Dextran

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