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N-Reacetylated Oligochitosan: PH Dependence Of Self-Assembly Properties And Antibacterial Activity.
I. Blagodatskikh, S. N. Kulikov, O. V. Vyshivannaya, E. A. Bezrodnykh, V. E. Tikhonov
Published 2017 · Chemistry, Medicine
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Oligochitosan (short chain chitosan) is more soluble in acidic aqueous media than a high molecular weight (MW) chitosan, but its antimicrobial activity decreases with increase in degree of acetylation (DA) and increase in pH above a critical pH threshold point. In the present study, oligochitosans varying in MW were additionally N-acetylated and their self-assembly properties and antibacterial activity toward Staphylococcus aureus and Escherichia coli were investigated in a wide pH range as a function of MW and DA. Light scattering studies reveals that reacetyleted oligochitosan with Mw ≤ 11 kDa is completely soluble in alkaline media (up to pH 12.5), if its DA is not less than 16%. Reacetylated chitosans with DA ∼ 30% are solubile in the entire pH range up to 12.5, if their Mw is not higher than 25 kDa, but they aggregate and precipitate from the solution at pH ≥ 8 when their Mw is above 25 kDa. Considering the influence of DA and MW, the antibacterial activity of reacetylated oligochitosans is maximal in the short interval of DA 16-28% at pH 7.4. These results are promising for expanding practical application of oligochitosan in pharmaceutical, cosmetic, and food compositions.
This paper references
Chitin and chitosan: Properties and applications
M. Rinaudo (2006)
Influence of glucosamine on oligochitosan solubility and antibacterial activity.
I. Blagodatskikh (2013)
Molecular weight and pH aspects of the efficacy of oligochitosan against methicillin-resistant Staphylococcus aureus (MRSA)
S. N. Kulikov (2012)
Effect of chitosan on epithelial permeability and structure.
V. Dodane (1999)
Static Light Scattering Studies on Chitosan Solutions: From Macromolecular Chains to Colloidal Dispersions
C. Schatz (2003)
Study of the depolymerization behavior of chitosan by hydrogen peroxide
F. Tian (2004)
Chitosan and its derivatives as intestinal absorption enhancers.
M. Thanou (2001)
Antibacterial activity of chitosans and chitosan oligomers with different molecular weights.
H. K. No (2002)
Influence of acetylation degree and molecular weight of homogeneous chitosans on antibacterial and antifungal activities.
I. Younes (2014)
A perspective on 30 years research on chitin and chitosan
A. Domard (2011)
Comparison of the ability of partially N-acetylated chitosans and chitooligosaccharides to elicit resistance reactions in wheat leaves
Heterogeneous Distribution of Amino Groups in Partially N-Acetylated Derivatives of Chitosan
S. Hirano (1981)
Studies on chitosan: 2. Solution stability and reactivity of partially N-acetylated chitosan derivatives in aqueous media.
Satoshi Aiba (1989)
Antibacterial Effects of Water-Soluble Low-Molecular-Weight Chitosans on Different Microorganisms
D. Gerasimenko (2004)
Continuum of structural organization from chitosan solutions to derived physical forms.
S. Popa-Nita (2010)
Antimicrobial Activity of Chitosan with Different Degrees of Acetylation and Molecular Weights
Y. Omura (2003)
Comparative Study of the First Heterogeneous Deacetylation of α- and β-Chitins in a Multistep Process
G. Lamarque (2004)
A review of chitin and chitosan applications
M. Kumar (2000)
Preparation and structure of chitosan soluble in wide pH range
Min Fan (2009)
Low molecular weight chitosan prepared with the aid of cellulase, lysozyme and chitinase: Characterisation and antibacterial activity
Shih-Bin Lin (2009)
Biomedical Activity of Chitin/Chitosan Based Materials—Influence of Physicochemical Properties Apart from Molecular Weight and Degree of N-Acetylation
J. Kumirska (2011)
Recent advances in drugs and prodrugs design of chitosan.
J. Vinšová (2008)
Stability of Chitosan—A Challenge for Pharmaceutical and Biomedical Applications
E. Szymańska (2015)
Production of Chitooligosaccharides and Their Potential Applications in Medicine
Berit B. Aam (2010)
Facile Preparation of Water-Soluble N-Acetylated Chitosan and Molecular Weight Dependence of Its Water-Solubility
N. Kubota (1997)
Preparation and characterisation of oligosaccharides produced by nitrous acid depolymerisation of chitosans.
K. Tømmeraas (2001)
Synergistic Combinations of Chitosans and Antibiotics in Staphylococcus aureus
S. Tin (2010)
Antimicrobial properties of chitosan and mode of action: a state of the art review.
M. Kong (2010)
Studies on chitin, 4. Evidence for formation of block and random copolymers of N‐acetyl‐D‐glucosamine and D‐glucosamine by hetero‐ and homogeneous hydrolyses
K. Kurita (1977)
Characterization of half N-acetylated chitosan powders and films
F. Feng (2012)
Atomic force microscopy study of the antibacterial effects of chitosans on Escherichia coli and Staphylococcus aureus.
P. Eaton (2008)
Potential applications of chitosan in oral mucosal delivery
S. Şenel (2010)
Evaluation of a method for the determination of antibacterial activity of chitosan
S. N. Kulikov (2016)
Antifungal activity of oligochitosans (short chain chitosans) against some Candida species and clinical isolates of Candida albicans: molecular weight-activity relationship.
S. N. Kulikov (2014)
Light scattering studies of the solution properties of chitosans of varying degrees of acetylation.
P. Sorlier (2003)
Advances in characterisation and biological activities of chitosan and chitosan oligosaccharides.
P. Zou (2016)
Water-solubility of chitosan and its antimicrobial activity
Caiqin Qin (2006)
The safety of chitosan as a pharmaceutical excipient.
P. Baldrick (2010)
Chitosan as a subphase disturbant of membrane lipid monolayers. The effect of temperature at varying pH: I. DPPG
B. Krajewska (2013)
Chitosan permeabilizes the plasma membrane and kills cells of Neurospora crassa in an energy dependent manner.
J. Palma-Guerrero (2009)
Short chain chitosan solutions: self-assembly and aggregates disruption effects
I. Blagodatskikh (2013)
Biodegradation, biodistribution and toxicity of chitosan.
T. Kean (2010)
Determination of degree of deacetylation of chitosan by 1H NMR spectroscopy
A. Hirai (1991)
Current views on fungal chitin/chitosan, human chitinases, food preservation, glucans, pectins and inulin: A tribute to Henri Braconnot, precursor of the carbohydrate polymers science, on the chitin bicentennial
R. Muzzarelli (2012)
Blood compatibility and biodegradability of partially N-acylated chitosan derivatives.
K. Lee (1995)
Relation between solution properties and degree of acetylation of chitosan: role of aging.
P. Sorlier (2002)
Chemical modification of chitin and chitosan 2: preparation and water soluble property of N-acylated or N-alkylated partially deacetylated chitins
H. Sashiwa (1999)
Physicochemical behavior of homogeneous series of acetylated chitosans in aqueous solution: role of various structural parameters.
G. Lamarque (2005)
Safety evaluation of short-term exposure to chitooligomers from enzymic preparation.
Caiqin Qin (2006)
Chitosan-based drug delivery systems.
A. Bernkop-Schnürch (2012)
Probing the modes of antibacterial activity of chitosan. Effects of pH and molecular weight on chitosan interactions with membrane lipids in Langmuir films.
B. Krajewska (2011)
Typical physicochemical behaviors of chitosan in aqueous solution.
C. Schatz (2003)
Depolymerization and de-N-acetylation of chitin oligomers in hydrochloric acid.
Aslak Einbu (2007)
Deamination of Carbohydrate Amines and Related Compounds
J. Williams (1975)
Insights into the Mode of Action of Chitosan as an Antibacterial Compound
Dina Raafat (2008)
Chitosan as a subphase disturbant of membrane lipid monolayers. The effect of temperature at varying pH: II. DPPC and cholesterol
B. Krajewska (2013)
Kinetics and efficiency of chitosan reacetylation
M. Lavertu (2012)
Influence of molecular weight on oral absorption of water soluble chitosans.
S. Chae (2005)
A simple preparation of half N-acetylated chitosan highly soluble in water and aqueous organic solvents.
N. Kubota (2000)
Acid hydrolysis of chitosans
K. M. Vårum (2001)
Hydrogen ion titration of chitosans with varying degrees of N-acetylation by monitoring induced 1H-NMR chemical shifts
M. Anthonsen (1995)
Susceptibility of Candida albicans and Enterococcus faecalis to Chitosan, Chlorhexidine gluconate and their combination in vitro.
N. Ballal (2009)
pH Effects on solubility, zeta potential, and correlation between antibacterial activity and molecular weight of chitosan.
Shun-Hsien Chang (2015)
Preparation, characterization, and swelling behavior of N-acetylated and deacetylated chitosans
S. M. Taghizadeh (2006)
Studies on chitosan: 3. Evidence for the presence of random and block copolymer structures in partially N-acetylated chitosans.
Satoshi Aiba (1991)
Antibacterial effects of chitosan and its water‐soluble derivatives on E. coli, plasmids DNA, and mRNA
X. Liu (2007)
Activity of Chitosans in combination with antibiotics in Pseudomonas aeruginosa
S. Tin (2009)
Electrophoretic light scattering studies of chitosans with different degrees of N-acetylation.
S. Strand (2001)
Antimicrobial Activity of Hetero-Chitosans and Their Oligosaccharides with Different Molecular Weights
P. Park (2004)
Relation between the degree of acetylation and the electrostatic properties of chitin and chitosan.
P. Sorlier (2001)
Water-solubility of partially N-acetylated chitosans as a function of pH: effect of chemical composition and depolymerisation
K. M. Vårum (1994)
Study on antimicrobial activity of chitosan with different molecular weights
lian-ying Zheng (2003)
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Polyelectrolyte Complexes of Partially Betainated Chitosan Derivatives Soluble in Weakly Alkaline Media
Inesa V. Blagodatskikh (2020)
Amphipathic chitosans improve the physicochemical properties of siRNA-chitosan nanoparticles at physiological conditions.
Grazieli Olinda Martins (2019)
Antibacterial Activity and Cytotoxicity of Betainated Oligochitosane Derivatives
I. Blagodatskikh (2018)
Chitosan in Biology, Microbiology, Medicine, and Agriculture
V. Varlamov (2018)
Consequences of chitosan decomposition by nitrous acid: Approach to non-branched oligochitosan oxime.
E. A. Bezrodnykh (2018)
Effect of Molecular Weight and Degree of Acetylation on Adjuvantive Properties of Chitosan Derivatives
S. Markushin (2018)