New approach to the quaternization of chitosan and its amphiphilic derivatives

Stepnova, Evgeniya A.; Тихонов, В. Е.; Babushkina, T.A.; Klimova, T. P.; Vorontsov, Evgeniy V.; Babak, Valéry G.; Лопатин, С. А.; Yamskov, I. A.

doi:10.1016/j.eurpolymj.2007.02.028

Cited by 56 publications

(20 citation statements)

References 34 publications

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“…All the C–H protons of chitin were shifted downfield by 0.36 ppm in QC‐5 and QC‐12 because of the absence of KOH. The signals from the acetyl group protons of N ‐acetyl‐glucosamine were observed at ≈1.97 ppm, and the signal between 2 and 3 ppm from the amino group protons of glucosamine was absent in QC‐5 and QC‐12, confirming again that deacetylation during the dissolution and quaternization of chitin is negligible . The significant signal at ≈3.14 ppm was assigned to the protons of the –N + (CH 3 ) 3 group, confirming the formation of quaternized β‐chitin derivatives.…”

Section: Antimicrobial and Hemolytic Activities Of Quaternized β‐Chitmentioning

confidence: 79%

Green Fabrication of Amphiphilic Quaternized β‐Chitin Derivatives with Excellent Biocompatibility and Antibacterial Activities for Wound Healing

et al. 2018

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Bacterial infection has always been a great threat to public health, and new antimicrobials to combat it are urgently needed. Here, a series of quaternized β-chitin derivatives is prepared simply and homogeneously in an aqueous KOH/urea solution, which is a high-efficiency, energy-saving, and "green" route for the modification of chitin. The mild reaction conditions keep the acetamido groups of β-chitin intact and introduce quaternary ammonium groups on the primary hydroxyl at the C-6 position of the chitin backbone, allowing the quaternized β-chitin derivatives (QCs) to easily form micelles. These QCs are found to exhibit excellent antimicrobial activities against Escherichia coli, Staphylococcus aureus, Candida albicans, and Rhizopus oryzae with minimum inhibitory concentrations (MICs) of 8, 12, 60, and 40 µg mL , respectively. As a specific highlight, their inherent outstanding biocompatibility and significant accelerating effects on the healing of uninfected, E. coli-infected, and S. aureus-infected wounds imply that these novel polysaccharide-based materials can be used as dressings for clinical skin regeneration, particularly for infected wounds.

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Section: Antimicrobial and Hemolytic Activities Of Quaternized β‐Chitmentioning

confidence: 79%

Green Fabrication of Amphiphilic Quaternized β‐Chitin Derivatives with Excellent Biocompatibility and Antibacterial Activities for Wound Healing

et al. 2018

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“…The ATR‐FTIR spectra of the PCU‐modified films revealed the presence of a most important band at 1471 cm −1 , which corresponded to the asymmetric angular bending of methyl and hexyl groups of quaternary nitrogen atoms . The band at 1250 cm −1 was assigned to the ester COC stretching in the polycarbonate segments…”

Section: Resultsmentioning

confidence: 99%

Biomimetic design of amphiphilic polycations and surface grafting onto polycarbonate urethane film as effective antibacterial agents with controlled hemocompatibility

Khan

Feng

Yang

et al. 2013

J. Polym. Sci. Part A: Polym. Chem.

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The synthetic polycations are ideal candidates as antimicrobial agents, because they resemble natural antimicrobial peptides, but to render hemocompatibility to these materials is a great challenge. Herein, we used 2‐(tert‐butyl‐aminoethyl) methacrylate (TBAEMA), to synthesize its homopolymer and pegylated random and diblock copolymers with polyethyleneglycol methacrylate (PEGMA, Mn = 360 Da) by single‐electron transfer–living radical polymerization (SET‐LRP). In the second step, the secondary amino groups in the precursor polymers were quaternized with iodomethane and bromohexane, to obtain three series of quaternized polymers. The antimicrobial properties of these quaternized polymers were evaluated against Escherichia coli (E. coli), by studying the minimum inhibitory concentrations (MICs) which ranged between 32 and 200 mg L−1 and showed higher values for the quaternized random than the diblock copolymers. In addition to, we have also demonstrated the grafting of these polycations onto polycarbonate urethane film surfaces, which showed good killing efficacy against E. coli. Furthermore, the hemolysis of these materials was investigated against human red blood cells, which indicated that except the quaternized homopolymers that showed highest hemolysis, all other amphiphilic polycations exhibited very low hemolytic activity. Therefore, our designed materials with controlled structures and functionality, synthesized from cheaply available resources could serve as useful agents in the field of biomedicines and implantable materials. © 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2013, 51, 3166–3176

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“…That side-product formation can be slowed down by increasing betaine/EEDQ ratio. 23 The quaternized chitosan derivatives can also be prepared by microwave irradiation. Chitosan is dispersed in isopropyl alcohol and the PH of solution was adjusted to basic.…”

Section: Figure 3: N-deacetylation and Hydrolysis Of Chitinmentioning

confidence: 99%

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2013

IJPSR

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Chitosan is a natural polysaccharide which is widely exploited for its various applications. It has received much attention as a functional biopolymer especially in pharmaceutics and medicine because of its better biodegradability, biocompatibility, versatility and availability. The unique biological applications of chitosan are attributed to these specific properties. The chemical and biological modification of chitosan is mainly done to increase its solubility in aqueous solutions and absorbability in the in vivo system. A variety of chemical modifications are employed to modify this carbohydrate polymer. The modifications of chitosan are influenced by several factors such as molecular weight of chitosan, viscosity, reaction conditions etc. The selective biological applications include antimicrobial, hypocholesterolemic, antitumor, anti-inflammatory, antioxidant, angiotensin-I-converting enzyme (ACE) inhibition, excluding toxins from the intestines, reducing heavy-metal poisoning in humans, mucoadhesive haemostatic, analgesic, radio-protective properties, preventing tooth decay and tooth diseases and immunity enhancing activities. It is also widely useful in biomedical industries and food industries. The present paper reviews the current trend of investigation on various useful modifications on chitosan and their applications in various fields. INTRODUCTION:Natural polysaccharides are being utilized more and more in the markets for the reason that they show biodegradability, biocompatibility, versatility, and are found plentiful in nature. The diversity of natural polysaccharides provides the chemist with a broad spectrum of raw materials that can be used in many biological applications.

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New approach to the quaternization of chitosan and its amphiphilic derivatives

Cited by 56 publications

References 34 publications

Green Fabrication of Amphiphilic Quaternized β‐Chitin Derivatives with Excellent Biocompatibility and Antibacterial Activities for Wound Healing

Green Fabrication of Amphiphilic Quaternized β‐Chitin Derivatives with Excellent Biocompatibility and Antibacterial Activities for Wound Healing

Biomimetic design of amphiphilic polycations and surface grafting onto polycarbonate urethane film as effective antibacterial agents with controlled hemocompatibility

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