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Antimicrobial activity of chitosan derivatives containing N-quaternized moieties in its backbone: a review.

Martins AF, Facchi SP, Follmann HD, Pereira AG, Rubira AF, Muniz EC - Int J Mol Sci (2014)

Bottom Line: However, chitosan applications as a biocide are only effective in acidic medium due to its low solubility in neutral and basic conditions.Also, the positive charges carried by the protonated amine groups of chitosan (in acidic conditions) that are the driving force for its solubilization are also associated with its antimicrobial activity.Recent reports in the literature demonstrate that such chitosan-derivatives present excellent antimicrobial activity due to permanent positive charge on nitrogen atoms side-bonded to the polymer backbone.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, Universidade Estadual de Maringá (UEM), Av. Colombo, 5790, Maringá-PR 87020-900, Brazil. afmartins50@yahoo.com.br.

ABSTRACT
Chitosan, which is derived from a deacetylation reaction of chitin, has attractive antimicrobial activity. However, chitosan applications as a biocide are only effective in acidic medium due to its low solubility in neutral and basic conditions. Also, the positive charges carried by the protonated amine groups of chitosan (in acidic conditions) that are the driving force for its solubilization are also associated with its antimicrobial activity. Therefore, chemical modifications of chitosan are required to enhance its solubility and broaden the spectrum of its applications, including as biocide. Quaternization on the nitrogen atom of chitosan is the most used route to render water-soluble chitosan-derivatives, especially at physiological pH conditions. Recent reports in the literature demonstrate that such chitosan-derivatives present excellent antimicrobial activity due to permanent positive charge on nitrogen atoms side-bonded to the polymer backbone. This review presents some relevant work regarding the use of quaternized chitosan-derivatives obtained by different synthetic paths in applications as antimicrobial agents.

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Route for synthesis of the N-quaternized chitosan derivatives. Reagents and conditions: (a) (i) TEA, pyridine, H2O; (ii) chloracetyl chloride, TEA, DMF, N2 atmosphere, 72 h, 22 °C; (iii) tertiary amine, DMF or NMP or pyridine, N2 atmosphere, NaI as catalyst when TEA and tripropylamine as reagents, 72 h, 60 °C, ion exchanged, dialysis; and (b) (i) methansulfonic acid, H2O; (ii) TBDMSCl, imidazole, DMSO, N2 atmosphere, 0 °C, 20 min, 2 × 24 h, 22 °C; (iii) chloracetyl chloride, TEA, pyridine dichloromethane, 1 h, 0 °C; (iv) dimethyldodecylamine or dimethylbutylamine, chloroform, 40 h, 22 °C; and (v) concentration of HCl, ethanol, 6 h, 22 °C [76,88].
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ijms-15-20800-f015: Route for synthesis of the N-quaternized chitosan derivatives. Reagents and conditions: (a) (i) TEA, pyridine, H2O; (ii) chloracetyl chloride, TEA, DMF, N2 atmosphere, 72 h, 22 °C; (iii) tertiary amine, DMF or NMP or pyridine, N2 atmosphere, NaI as catalyst when TEA and tripropylamine as reagents, 72 h, 60 °C, ion exchanged, dialysis; and (b) (i) methansulfonic acid, H2O; (ii) TBDMSCl, imidazole, DMSO, N2 atmosphere, 0 °C, 20 min, 2 × 24 h, 22 °C; (iii) chloracetyl chloride, TEA, pyridine dichloromethane, 1 h, 0 °C; (iv) dimethyldodecylamine or dimethylbutylamine, chloroform, 40 h, 22 °C; and (v) concentration of HCl, ethanol, 6 h, 22 °C [76,88].


Antimicrobial activity of chitosan derivatives containing N-quaternized moieties in its backbone: a review.

Martins AF, Facchi SP, Follmann HD, Pereira AG, Rubira AF, Muniz EC - Int J Mol Sci (2014)

Route for synthesis of the N-quaternized chitosan derivatives. Reagents and conditions: (a) (i) TEA, pyridine, H2O; (ii) chloracetyl chloride, TEA, DMF, N2 atmosphere, 72 h, 22 °C; (iii) tertiary amine, DMF or NMP or pyridine, N2 atmosphere, NaI as catalyst when TEA and tripropylamine as reagents, 72 h, 60 °C, ion exchanged, dialysis; and (b) (i) methansulfonic acid, H2O; (ii) TBDMSCl, imidazole, DMSO, N2 atmosphere, 0 °C, 20 min, 2 × 24 h, 22 °C; (iii) chloracetyl chloride, TEA, pyridine dichloromethane, 1 h, 0 °C; (iv) dimethyldodecylamine or dimethylbutylamine, chloroform, 40 h, 22 °C; and (v) concentration of HCl, ethanol, 6 h, 22 °C [76,88].
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4264197&req=5

ijms-15-20800-f015: Route for synthesis of the N-quaternized chitosan derivatives. Reagents and conditions: (a) (i) TEA, pyridine, H2O; (ii) chloracetyl chloride, TEA, DMF, N2 atmosphere, 72 h, 22 °C; (iii) tertiary amine, DMF or NMP or pyridine, N2 atmosphere, NaI as catalyst when TEA and tripropylamine as reagents, 72 h, 60 °C, ion exchanged, dialysis; and (b) (i) methansulfonic acid, H2O; (ii) TBDMSCl, imidazole, DMSO, N2 atmosphere, 0 °C, 20 min, 2 × 24 h, 22 °C; (iii) chloracetyl chloride, TEA, pyridine dichloromethane, 1 h, 0 °C; (iv) dimethyldodecylamine or dimethylbutylamine, chloroform, 40 h, 22 °C; and (v) concentration of HCl, ethanol, 6 h, 22 °C [76,88].
Bottom Line: However, chitosan applications as a biocide are only effective in acidic medium due to its low solubility in neutral and basic conditions.Also, the positive charges carried by the protonated amine groups of chitosan (in acidic conditions) that are the driving force for its solubilization are also associated with its antimicrobial activity.Recent reports in the literature demonstrate that such chitosan-derivatives present excellent antimicrobial activity due to permanent positive charge on nitrogen atoms side-bonded to the polymer backbone.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, Universidade Estadual de Maringá (UEM), Av. Colombo, 5790, Maringá-PR 87020-900, Brazil. afmartins50@yahoo.com.br.

ABSTRACT
Chitosan, which is derived from a deacetylation reaction of chitin, has attractive antimicrobial activity. However, chitosan applications as a biocide are only effective in acidic medium due to its low solubility in neutral and basic conditions. Also, the positive charges carried by the protonated amine groups of chitosan (in acidic conditions) that are the driving force for its solubilization are also associated with its antimicrobial activity. Therefore, chemical modifications of chitosan are required to enhance its solubility and broaden the spectrum of its applications, including as biocide. Quaternization on the nitrogen atom of chitosan is the most used route to render water-soluble chitosan-derivatives, especially at physiological pH conditions. Recent reports in the literature demonstrate that such chitosan-derivatives present excellent antimicrobial activity due to permanent positive charge on nitrogen atoms side-bonded to the polymer backbone. This review presents some relevant work regarding the use of quaternized chitosan-derivatives obtained by different synthetic paths in applications as antimicrobial agents.

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