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

International Journal of Biological Macromolecules
Andreii S KritchenkovVictor N Khrustalev

Abstract

This work describes ultrasound-assisted phenol-yne addition of p-hydroxybenzaldehyde and propargylic ester of betaine hydrochloride giving only 2-((3-(4-formylphenoxy)allyl)oxy)-N,N,N-trimethyl-2-oxoethan-1-aminium chloride as a product at 100kHz 300W in water. The ultrasonic assisted phenol-yne addition was enhanced to chitosan chemistry. Phenolic chitosan derivatives were obtained by treatment of chitosan with o-, m- or p-hydroxybenzaldehyde followed by reduction of the formed CN bound by NaBH4. The phenolic chitosan derivatives (phenolic component) were involved in ultrasound-mediated reaction with propargylic ester of betaine hydrochloride (yne component). The reaction led to betaine chitosan derivatives in different degree of substitution as o-, m- and p-isomers. The phenolic and betaine derivatives were tested as antibacterial agents against E. coli in comparison with reference antibiotic Tetracycline. Betaine derivatives showed high antibacterial activity. The most effective polymer was p-isomer of high substituted betaine derivative and its activity was more than 2 times higher than the activity of Tetracycline. The nanoparticles based on this polymer were obtained by ionic gelation method. They had 2Rh 126nm, ξ-potenti...Continue Reading

References

Oct 12, 2004·Ultrasonics Sonochemistry·Giancarlo CravottoMichele Trotta
Oct 20, 2004·Ultrasonics Sonochemistry·Giancarlo CravottoLivio Stevanato
Jun 7, 2008·Ultrasonics Sonochemistry·Mohammad R KasaaiGérard Charlet
Jul 19, 2008·International Journal of Pharmaceutics·V CardileG Cravotto
May 15, 2010·Ultrasonics Sonochemistry·Mohammad Taghi Taghizadeh, Reza Abdollahi
Jan 11, 2011·Ultrasonics Sonochemistry·Pedro CintasGiancarlo Cravotto
Dec 3, 2013·Ultrasonics Sonochemistry·Mohamad Taghi Taghizadeh, Ali Bahadori
Dec 3, 2014·Ultrasonics Sonochemistry·Shabbar AbbasXiaoming Zhang
Apr 11, 2015·Ultrasonics Sonochemistry·Zhenghua HuangDandan Zhang
Nov 21, 2015·Ultrasonics Sonochemistry·Nimesh PokhrelNezih Pala
Nov 21, 2015·Ultrasonics Sonochemistry·Petya PetkovaTzanko Tzanov
Dec 26, 2015·Ultrasonics Sonochemistry·M Soledad BelluzoM Susana Cortizo
Mar 1, 2016·Beilstein Journal of Nanotechnology·Ilana PerelshteinAharon Gedanken
Aug 16, 2016·Journal of Endodontics·Annie Shrestha, Anil Kishen
Oct 6, 2016·International Journal of Hyperthermia : the Official Journal of European Society for Hyperthermic Oncology, North American Hyperthermia Group·Samira EynaliElaheh Esmaelbeygi
Mar 1, 2017·International Journal of Nanomedicine·Linlin WangLongquan Shao
Mar 10, 2017·Ultrasonics Sonochemistry·Gareth J PriceSaira Bibi
Mar 23, 2017·Carbohydrate Polymers·Arno VerleeChristian V Stevens
Jun 22, 2017·Ultrasonics Sonochemistry·Richard James WoodMadeleine J Bussemaker
Feb 23, 2018·Current Pharmaceutical Design·Juliana Miguel VazDiego Mantovani
May 1, 2018·Ultrasonics Sonochemistry·Manuela Maria Iftime, Luminita Marin
Apr 14, 2013·Journal of Materials Chemistry. B, Materials for Biology and Medicine·Ilana PerelshteinAharon Gedanken
Mar 7, 2015·Journal of Materials Chemistry. B, Materials for Biology and Medicine·Ali Shakeri-ZadehSamideh Khoei

❮ Previous
Next ❯

Citations

Jan 29, 2020·International Journal of Biological Macromolecules·Andreii S KritchenkovVictor N Khrustalev

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.