Online citations, reference lists, and bibliographies.
← Back to Search

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

Cite This
Download PDF
Analyze on Scholarcy
Share
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
10.1016/J.PROGPOLYMSCI.2006.06.001
Chitin and chitosan: Properties and applications
M. Rinaudo (2006)
10.1016/j.carres.2013.08.012
Influence of glucosamine on oligochitosan solubility and antibacterial activity.
I. Blagodatskikh (2013)
10.1016/J.CARBPOL.2011.08.017
Molecular weight and pH aspects of the efficacy of oligochitosan against methicillin-resistant Staphylococcus aureus (MRSA)
S. N. Kulikov (2012)
10.1016/S0378-5173(99)00030-7
Effect of chitosan on epithelial permeability and structure.
V. Dodane (1999)
10.1021/LA034410N
Static Light Scattering Studies on Chitosan Solutions: From Macromolecular Chains to Colloidal Dispersions
C. Schatz (2003)
10.1016/J.CARBPOL.2004.03.016
Study of the depolymerization behavior of chitosan by hydrogen peroxide
F. Tian (2004)
10.1016/S0169-409X(01)00180-6
Chitosan and its derivatives as intestinal absorption enhancers.
M. Thanou (2001)
10.1016/S0168-1605(01)00717-6
Antibacterial activity of chitosans and chitosan oligomers with different molecular weights.
H. K. No (2002)
10.1016/j.ijfoodmicro.2014.04.029
Influence of acetylation degree and molecular weight of homogeneous chitosans on antibacterial and antifungal activities.
I. Younes (2014)
10.1016/J.CARBPOL.2010.04.083
A perspective on 30 years research on chitin and chitosan
A. Domard (2011)
10.1104/PP.118.4.1353
Comparison of the ability of partially N-acetylated chitosans and chitooligosaccharides to elicit resistance reactions in wheat leaves
Vander (1998)
10.1271/BBB1961.45.1335
Heterogeneous Distribution of Amino Groups in Partially N-Acetylated Derivatives of Chitosan
S. Hirano (1981)
10.1016/0141-8130(89)90077-9
Studies on chitosan: 2. Solution stability and reactivity of partially N-acetylated chitosan derivatives in aqueous media.
Satoshi Aiba (1989)
10.1023/B:ABIM.0000025947.84650.b4
Antibacterial Effects of Water-Soluble Low-Molecular-Weight Chitosans on Different Microorganisms
D. Gerasimenko (2004)
10.1021/bm9012138
Continuum of structural organization from chitosan solutions to derived physical forms.
S. Popa-Nita (2010)
10.4265/BIO.8.25
Antimicrobial Activity of Chitosan with Different Degrees of Acetylation and Molecular Weights
Y. Omura (2003)
10.1021/BM034498J
Comparative Study of the First Heterogeneous Deacetylation of α- and β-Chitins in a Multistep Process
G. Lamarque (2004)
10.1016/S1381-5148(00)00038-9
A review of chitin and chitosan applications
M. Kumar (2000)
10.1016/J.CARBPOL.2009.03.031
Preparation and structure of chitosan soluble in wide pH range
Min Fan (2009)
10.1016/J.FOODCHEM.2009.02.002
Low molecular weight chitosan prepared with the aid of cellulase, lysozyme and chitinase: Characterisation and antibacterial activity
Shih-Bin Lin (2009)
10.3390/POLYM3041875
Biomedical Activity of Chitin/Chitosan Based Materials—Influence of Physicochemical Properties Apart from Molecular Weight and Degree of N-Acetylation
J. Kumirska (2011)
10.2174/138161208799316410
Recent advances in drugs and prodrugs design of chitosan.
J. Vinšová (2008)
10.3390/md13041819
Stability of Chitosan—A Challenge for Pharmaceutical and Biomedical Applications
E. Szymańska (2015)
10.3390/md8051482
Production of Chitooligosaccharides and Their Potential Applications in Medicine
Berit B. Aam (2010)
10.1295/POLYMJ.29.123
Facile Preparation of Water-Soluble N-Acetylated Chitosan and Molecular Weight Dependence of Its Water-Solubility
N. Kubota (1997)
10.1016/S0008-6215(01)00130-6
Preparation and characterisation of oligosaccharides produced by nitrous acid depolymerisation of chitosans.
K. Tømmeraas (2001)
10.2174/157018010789869406
Synergistic Combinations of Chitosans and Antibiotics in Staphylococcus aureus
S. Tin (2010)
10.1016/j.ijfoodmicro.2010.09.012
Antimicrobial properties of chitosan and mode of action: a state of the art review.
M. Kong (2010)
10.1002/MACP.1977.021781203
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)
10.1016/J.PROENG.2011.12.511
Characterization of half N-acetylated chitosan powders and films
F. Feng (2012)
10.1016/j.ultramic.2008.04.015
Atomic force microscopy study of the antibacterial effects of chitosans on Escherichia coli and Staphylococcus aureus.
P. Eaton (2008)
10.1016/S1773-2247(10)50003-0
Potential applications of chitosan in oral mucosal delivery
S. Şenel (2010)
10.1134/S0003683816050100
Evaluation of a method for the determination of antibacterial activity of chitosan
S. N. Kulikov (2016)
10.1016/j.ejmech.2013.12.017
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)
10.1021/BM034054N
Light scattering studies of the solution properties of chitosans of varying degrees of acetylation.
P. Sorlier (2003)
10.1016/j.foodchem.2015.06.076
Advances in characterisation and biological activities of chitosan and chitosan oligosaccharides.
P. Zou (2016)
10.1016/J.CARBPOL.2005.09.023
Water-solubility of chitosan and its antimicrobial activity
Caiqin Qin (2006)
10.1016/j.yrtph.2009.09.015
The safety of chitosan as a pharmaceutical excipient.
P. Baldrick (2010)
10.1016/J.COLSURFA.2013.03.015
Chitosan as a subphase disturbant of membrane lipid monolayers. The effect of temperature at varying pH: I. DPPG
B. Krajewska (2013)
10.1016/j.fgb.2009.02.010
Chitosan permeabilizes the plasma membrane and kills cells of Neurospora crassa in an energy dependent manner.
J. Palma-Guerrero (2009)
10.1007/s10965-013-0073-0
Short chain chitosan solutions: self-assembly and aggregates disruption effects
I. Blagodatskikh (2013)
10.1016/j.addr.2009.09.004
Biodegradation, biodistribution and toxicity of chitosan.
T. Kean (2010)
10.1007/BF00299352
Determination of degree of deacetylation of chitosan by 1H NMR spectroscopy
A. Hirai (1991)
10.1016/J.CARBPOL.2011.09.063
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)
10.1016/0142-9612(95)98126-Y
Blood compatibility and biodegradability of partially N-acylated chitosan derivatives.
K. Lee (1995)
10.1021/BM0256146
Relation between solution properties and degree of acetylation of chitosan: role of aging.
P. Sorlier (2002)
10.1016/S0144-8617(98)00167-2
Chemical modification of chitin and chitosan 2: preparation and water soluble property of N-acylated or N-alkylated partially deacetylated chitins
H. Sashiwa (1999)
10.1021/BM0496357
Physicochemical behavior of homogeneous series of acetylated chitosans in aqueous solution: role of various structural parameters.
G. Lamarque (2005)
10.1016/J.FCT.2005.11.009
Safety evaluation of short-term exposure to chitooligomers from enzymic preparation.
Caiqin Qin (2006)
10.1016/j.ejpb.2012.04.007
Chitosan-based drug delivery systems.
A. Bernkop-Schnürch (2012)
10.1021/bm2012295
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)
10.1021/BM025724C
Typical physicochemical behaviors of chitosan in aqueous solution.
C. Schatz (2003)
10.1021/BM0608535
Depolymerization and de-N-acetylation of chitin oligomers in hydrochloric acid.
Aslak Einbu (2007)
10.1016/S0065-2318(08)60294-2
Deamination of Carbohydrate Amines and Related Compounds
J. Williams (1975)
10.1128/AEM.00453-08
Insights into the Mode of Action of Chitosan as an Antibacterial Compound
Dina Raafat (2008)
10.1016/J.COLSURFA.2013.03.018
Chitosan as a subphase disturbant of membrane lipid monolayers. The effect of temperature at varying pH: II. DPPC and cholesterol
B. Krajewska (2013)
10.1016/J.CARBPOL.2011.08.096
Kinetics and efficiency of chitosan reacetylation
M. Lavertu (2012)
10.1016/J.JCONREL.2004.10.012
Influence of molecular weight on oral absorption of water soluble chitosans.
S. Chae (2005)
10.1016/S0008-6215(99)00263-3
A simple preparation of half N-acetylated chitosan highly soluble in water and aqueous organic solvents.
N. Kubota (2000)
10.1016/S0144-8617(00)00288-5
Acid hydrolysis of chitosans
K. M. Vårum (2001)
10.1016/0144-8617(95)00010-5
Hydrogen ion titration of chitosans with varying degrees of N-acetylation by monitoring induced 1H-NMR chemical shifts
M. Anthonsen (1995)
10.1111/J.1747-4477.2008.00126.X
Susceptibility of Candida albicans and Enterococcus faecalis to Chitosan, Chlorhexidine gluconate and their combination in vitro.
N. Ballal (2009)
10.1016/j.carbpol.2015.07.072
pH Effects on solubility, zeta potential, and correlation between antibacterial activity and molecular weight of chitosan.
Shun-Hsien Chang (2015)
10.1016/J.CARBPOL.2005.10.037
Preparation, characterization, and swelling behavior of N-acetylated and deacetylated chitosans
S. M. Taghizadeh (2006)
10.1016/0141-8130(91)90008-I
Studies on chitosan: 3. Evidence for the presence of random and block copolymer structures in partially N-acetylated chitosans.
Satoshi Aiba (1991)
10.1002/APP.25421
Antibacterial effects of chitosan and its water‐soluble derivatives on E. coli, plasmids DNA, and mRNA
X. Liu (2007)
10.7150/IJBS.5.153
Activity of Chitosans in combination with antibiotics in Pseudomonas aeruginosa
S. Tin (2009)
10.1021/BM015598X
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)
10.1021/BM015531+
Relation between the degree of acetylation and the electrostatic properties of chitin and chitosan.
P. Sorlier (2001)
10.1016/0144-8617(94)90140-6
Water-solubility of partially N-acetylated chitosans as a function of pH: effect of chemical composition and depolymerisation
K. M. Vårum (1994)
10.1016/J.CARBPOL.2003.07.009
Study on antimicrobial activity of chitosan with different molecular weights
lian-ying Zheng (2003)



This paper is referenced by
Semantic Scholar Logo Some data provided by SemanticScholar