Preparation and characterization of a quaternary ammonium derivative of pectin

Fan, Lihong; Cao, Mi; Gao, Song; Wang, Weiping; Peng, Kai; Tan, Chang; Wen, Feng; Tao, Shengxiang; Xie, Weiguo

doi:10.1016/j.carbpol.2012.01.021

Cited by 78 publications

(14 citation statements)

References 42 publications

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“…The alkali metal hydroxide, NaOH, catalyzed the synthesiswhich followed the nucleophilic substitution SN2 reaction-to produce a strong nucleophile and break the epoxide ring before connecting the alkyl chain. The alkyl chain attached to the pectin backbone is anticipated to be non-specific, and it might have happened at both the C-6 carboxylate and hydroxyl groups [24]. The FTIR analysis of alkylated pectin was used to identify the spectroscopic alterations brought by the glycidyl tert-butyl ether modification, and the findings were compared to the native pectin.…”

Section: Resultsmentioning

confidence: 99%

Amphiphilic Alkylated Pectin Hydrogels for Enhanced Topical Delivery of Fusidic Acid: Formulation and In Vitro Investigation

Bostanudin¹

2022

Sci. Pharm.

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Hydrogels constructed of amphiphilically modified polysaccharides have attracted a lot of interest because of their potential to augment drug diffusion over the skin. This research describes the synthesis of amphiphilic alkylated pectin via glycidyl tert-butyl ether modification (alkylation degree 15.7%), which was characterized using spectroscopic and thermal analysis techniques and then formulated into hydrogels for the study of their potential in regulating fusidic acid diffusion topically. The hydrogels were formulated by the ionic interaction of negatively charged pectin and positively charged crosslinker CaCl2, with a reported fusidic acid loading degree of 93–95%. Hydrogels made of alkylated pectin showed a lower swelling percentage than that of native pectin, resulting in a slower fusidic acid release. The influence of pH on the swelling percentage and drug release was also investigated, with results revealing that greater pH enhanced swelling percentage and drug release. The in vitro interactions with HaCaT cells revealed negligible cytotoxicity under application-relevant settings. Utilizing Franz diffusion cells, the alkylated pectin hydrogels caused fusidic acid to penetrate the Strat-M® membrane at a 1.5-fold higher rate than the native pectin hydrogels. Overall, the in vitro results showed that alkylated pectin hydrogels have a lot of promise for topical distribution, which needs further investigation.

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Section: Resultsmentioning

confidence: 99%

Amphiphilic Alkylated Pectin Hydrogels for Enhanced Topical Delivery of Fusidic Acid: Formulation and In Vitro Investigation

Bostanudin¹

2022

Sci. Pharm.

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“…45,46 In 1 H NMR spectra, besides the proton signals at 5.3 ppm for H1 and 3.3−3.9 ppm for H2−H6 on the starch backbone, two characteristic peaks at 3.20 and 3.95 ppm were ascribed to the proton signals of the methyl groups of quaternary ammonium groups and methylene of the carboxymethyl groups, respectively. 46 The aforementioned results of FTIR and 1 H NMR both confirmed that anionic and cationic moieties, i.e., CTA and monochloroacetic acid, have been introduced onto the starch backbone successfully.…”

Section: Methodsmentioning

confidence: 99%

Flocculation of Both Kaolin and Hematite Suspensions Using the Starch-Based Flocculants and Their Floc Properties

Haijiang

Cai

Yuan

et al. 2014

Ind. Eng. Chem. Res.

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In this work, two kinds of starch-based flocculants with the same chemically modified functional groups but far different substitution degrees, (2-hydroxypropyl)trimethylammonium chloride etherified carboxymethyl starch (denoted as CMS-CTA-P and CMS-CTA-N, respectively) were successfully prepared. CMS-CTA-P and CMS-CTA-N bear opposite surface charge properties in water under most of the measured pH range. The flocculation performance of these two flocculants has been systematically studied using kaolin and hematite suspensions as synthetic wastewater under various pH conditions. CMS-CTA-P and CMS-CTA-N exhibited inverse flocculation behavior, but the commonness was that the starch-based flocculants with charge opposite to those of the contaminants in water always had higher flocculation efficiency. On the basis of the apparent flocculation performance and ζ-potential measurement, patching, a special charge neutralization mechanism, was significant here. Moreover, the floc properties including the floc size, fractal structure, and regrowth ability of flocs have been systematically studied by an in situ light-scattering technique in combination with fractal theory for further investigation of the flocculation mechanisms during the flocculation processes. The pH dependence of the floc properties and conformational changes of the polymeric flocculants indicated that bridging also made adequate contributions to efficient flocculation.

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“…Scheme 20. Formation of ether derivatives of pectin by addition reaction of pectin with in situ generated glycidyltrimethylammonium chloride in basic aqueous medium (adapted from Fan et al 2012) A similar reaction was published by Bostanudin et al (2019) describing the etherification of pectin in water at a pH value of 12 lasting for 16 h (Scheme 21). The DS ranging from values of 0.10 up to 0.14 was calculated from the 1 H NMR spectra.…”

Section: Alkylation Reaction At the Hydroxyl Groupmentioning

confidence: 97%

Chemical modification of pectin and polygalacturonic acid: A critical review

Würfel

Geitel

et al. 2021

BioRes

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Pectin, as a sustainable biopolymer with its two complementary functionalities (carboxyl and hydroxyl moieties) imparted in the α-1,4-galacturonic acid repeating unit, has gained increasing attention in the last few years. The interest in this ubiquitously occurring plant originating polysaccharide (PS) has shifted slowly from applications as a food additive to a broader range of potential applications in medicine, cosmetics, and other industries. Due to the increasing interest in alternatives for petrochemical materials, PSs as biomaterials have gained increasing attention in industrial processes in general. In the last decade, an increasing number of chemical transformations related to pectin have been published, and this is a prerequisite for the design of the structure and hence properties of novel biopolymer-based materials. This work aims to review the chemical modifications of pectin by covalent linkage of the last decade and analyze the materials obtained with these chemical methods critically.

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Preparation and characterization of a quaternary ammonium derivative of pectin

Cited by 78 publications

References 42 publications

Amphiphilic Alkylated Pectin Hydrogels for Enhanced Topical Delivery of Fusidic Acid: Formulation and In Vitro Investigation

Amphiphilic Alkylated Pectin Hydrogels for Enhanced Topical Delivery of Fusidic Acid: Formulation and In Vitro Investigation

Flocculation of Both Kaolin and Hematite Suspensions Using the Starch-Based Flocculants and Their Floc Properties

Chemical modification of pectin and polygalacturonic acid: A critical review

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