Synthesis of C6-amino agarose and evaluation of its antibacterial activity

Synthesis of C6-amino agarose and evaluation of its antibacterial activity

In this paper, the biologically inert agarose was selectively modified at C6 of β-d-Galp units to produce an amino derivative with antibacterial property. The synthetic route involved the preparation of tosyl and azido agarose intermediates. All the polysaccharide derivatives were characterized by m...

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Bibliographic Details
Published in:Carbohydrate research Vol. 507; p. 108387
Main Authors: Heuko, Janaina G., Duarte, Maria Eugênia R., Gonçalves, Alan G., Noseda, Miguel D., Murakami, Fabio S., de Carvalho, Mariana M., Ducatti, Diogo R.B.
Format: Journal Article
Language:English
Published: Netherlands Elsevier Ltd 01-09-2021
Subjects:
Agarose
Amino polysaccharide
Anti-Bacterial Agents - chemical synthesis
Anti-Bacterial Agents - chemistry
Anti-Bacterial Agents - pharmacology
Antibacterial activity
Azido polysaccharide
Escherichia coli - drug effects
Galactan
Microbial Sensitivity Tests
Pseudomonas aeruginosa - drug effects
Sepharose - chemistry
Staphylococcus aureus - drug effects
Tosylation
Antibacterial activity
Tosylation
Galactan
Azido polysaccharide
Agarose
Amino polysaccharide
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Summary:In this paper, the biologically inert agarose was selectively modified at C6 of β-d-Galp units to produce an amino derivative with antibacterial property. The synthetic route involved the preparation of tosyl and azido agarose intermediates. All the polysaccharide derivatives were characterized by mono- and bidimensional 1H and 13C NMR and FT-IR analysis. A water-soluble amino polymer (Mw = 39,000 g mol−1, DSamino = 0.50) was produced by partial acid hydrolysis showing bactericidal and bacteriostatic activity against P. aeruginosa (ATCC 9027), S. aureus (ATCC 6538), and E. coli (ATCC 25922), with MIC values lower than 2.5 mg mL−1 and MBC values ranging from 2.5 to 5.0 mg mL−1. [Display omitted] •Agarose was selectively modified at C6 of β-D-Galp units.•Amino-agarose was synthesized via a new route involving tosyl and azido intermediates.•A water-soluble amino-agarose was produced by partial acid hydrolysis.•The amino derivative showed bactericidal and bacteriostatic activity.
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ISSN:0008-6215
1873-426X
1873-426X
DOI:10.1016/j.carres.2021.108387