Ultrasound-assisted catalyst-free phenol-yne reaction for the synthesis of new water-soluble chitosan derivatives and their nanoparticles with enhanced antibacterial properties

Kritchenkov, Andreii S.; Egorov, Anton R.; Волкова, О. В.; Kritchenkov, Ilya S.; Kurliuk, Aleh V.; Shakola, Tatsiana V.; Khrustalev, Victor N.

doi:10.1016/j.ijbiomac.2019.07.203

Cited by 28 publications

(9 citation statements)

References 58 publications

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“…Antimicrobial activity (in vitro) was evaluated completely as previously described by some of us [ 20 , 21 , 22 ]. The DPPH• scavenging effect was evaluated according to the published procedure [ 23 ].…”

Section: Methodsmentioning

confidence: 99%

Rhodamine B-Containing Chitosan-Based Films: Preparation, Luminescent, Antibacterial, and Antioxidant Properties

Khubiev,

Egorov,

Semenkova

et al. 2024

Polymers

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In this study, Rhodamine B-containing chitosan-based films were prepared and characterized using their mechanical, photophysical, and antibacterial properties. The films were synthesized using the casting method and their mechanical properties, such as tensile strength and elongation at break, were found to be dependent on the chemical composition and drying process. Infrared spectroscopy and X-ray diffraction analysis were used to examine the chemical structure and degree of structural perfection of the films. The photophysical properties of the films, including absorption spectra, fluorescence detection, emission quantum yields, and lifetimes of excited states, were studied in detail. Rhodamine B-containing films exhibited higher temperature sensitivity and showed potential as fluorescent temperature sensors in the physiological range. The antibacterial activity of the films was tested against Gram-positive bacteria S. aureus and Gram-negative bacteria E. coli, with Rhodamine B-containing films demonstrating more pronounced antibacterial activity compared to blank films. The findings suggest that the elaborated chitosan-based films, particularly those containing Rhodamine B can be of interest for further research regarding their application in various fields such as clinical practice, the food industry, and agriculture due to their mechanical, photophysical, and antibacterial properties.

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Section: Methodsmentioning

confidence: 99%

Rhodamine B-Containing Chitosan-Based Films: Preparation, Luminescent, Antibacterial, and Antioxidant Properties

Khubiev,

Egorov,

Semenkova

et al. 2024

Polymers

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“…There are several works involving natural monomers as building blocks for the construction of drug delivery systems. [79,[126][127] However, these works focused more on biological purposes, and natural monomers were not the research priority. Systematic studies of polymerization itself using these monomers are scarce.…”

Section: Monomer Scope Expansionmentioning

confidence: 99%

X‐yne click polymerization

Qin

Tang

2023

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Alkyne‐based click polymerizations have been nurtured into a powerful synthetic technique for the preparation of new polymers with advanced structures and versatile properties. Among them, the emerging thiol‐yne, hydroxyl‐yne, and amino‐yne click polymerizations have made remarkable progress from reactions to applications. These polymerizations avoid the usage of inherently dangerous monomers and are safer to operate than the classical azide‐alkyne click polymerization (AACP), making them more prospective for diverse applications. To greatly promote the new alkyne‐based click polymerizations beyond AACP, a new concept of “X‐yne click polymerization” is proposed to unify them, where “X” denotes the monomers that can react with alkynes under mild reaction conditions, including thiols, alcohols, amines, and other promising ones. In this review, we mainly present a brief account of the progress of X‐yne click polymerization and discuss in detail the challenges and opportunities in this field.

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“…Recently, we reported that ultrasonic irradiation can promote a number of heterogeneous organic transformation of chitin and chitosan resulting in dramatic decrease of the reaction time and the required amount of reagent, wherein it leads to increase in the degree of conversion (in comparison with the conventional, i.e., ultrasound-free conditions) [28][29][30][31]. Moreover, it is often possible to find such acoustic conditions that promote the desired reaction without causing ultrasonic degradation of chitosan backbone [9,32,33]. As an extension of our previous findings, we attempted to promote the DCC-mediated conjugation of ciprofloxacin with chitosan using ultrasound.…”

Section: Synthesis Of Ciprofloxacin-chitosan Conjugates In Which Cipr...mentioning

confidence: 99%

Chitosan-Based Ciprofloxacin Extended Release Systems: Combined Synthetic and Pharmacological (In Vitro and In Vivo) Studies

et al. 2022

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Ciprofloxacin is one of the most effective antibiotics, but it is characterized by a range of side effects. Elaboration of drug-releasing systems which allow to diminish toxicity of ciprofloxacin is a challenging task in medicinal chemistry. The current study is focused on development of new ciprofloxacin releasing systems (CRS). We found that ultrasound efficiently promotes N,N′-dicyclohexyl carbodiimide-mediated coupling between COOH and NH2 functionalities in water. This was used for conjugation of ciprofloxacin to chitosan. The obtained ciprofloxacin/chitosan conjugates are capable of forming their self-assembled nanoparticles (SANPs) in aqueous medium. The SANPs can be additionally loaded by ciprofloxacin to form new CRS. The CRS demonstrated high loading and encapsulation efficiency and they are characterized by extended release profile (20 h). The elaborated CRS were tested in vivo in rats. The in vivo antibacterial effect of the CRS exceeded that of the starting ciprofloxacin. Moreover, the in vivo acute and subacute toxicity of the nanoparticles was almost identical to that of the chitosan, which is considered as the non-toxic biopolymer.

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Ultrasound-assisted catalyst-free phenol-yne reaction for the synthesis of new water-soluble chitosan derivatives and their nanoparticles with enhanced antibacterial properties

Cited by 28 publications

References 58 publications

Rhodamine B-Containing Chitosan-Based Films: Preparation, Luminescent, Antibacterial, and Antioxidant Properties

Rhodamine B-Containing Chitosan-Based Films: Preparation, Luminescent, Antibacterial, and Antioxidant Properties

X‐yne click polymerization

Chitosan-Based Ciprofloxacin Extended Release Systems: Combined Synthetic and Pharmacological (In Vitro and In Vivo) Studies

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