Impact of chain length on antibacterial activity and hemocompatibility of quaternary N-alkyl and n,n-dialkyl chitosan derivatives.

A highly efficient method for chemical modification of chitosan biopolymers by reductive amination to yield N,N-dialkyl chitosan derivatives was developed. The use of 3,6-O-di-tert-butyldimethylsilylchitosan as a precursor enabled the first 100% disubstitution of the amino groups with long alkyl cha...

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Bibliographic Details
Published in:Biomacromolecules
Main Authors: Sahariah, Priyanka, Benediktssdóttir, Berglind E, Hjálmarsdóttir, Martha Á, Sigurjonsson, Olafur E, Sørensen, Kasper K, Thygesen, Mikkel B, Jensen, Knud J, Másson, Már
Other Authors: 1 Univ Iceland, Sch Hlth Sci, Fac Pharmaceut Sci, IS-107 Reykjavik, Iceland 2 Univ Iceland, Fac Med, Dept Biomed Sci, IS-101 Reykjavik, Iceland 3 Landspitali Univ Hosp, Blood Bank, REModeL Lab, IS-105 Reykjavik, Iceland 4 Reykjavik Univ, Inst Biomed & Neural Engn, IS-101 Reykjavik, Iceland 5 Univ Copenhagen, Ctr Carbohydrate Recognit & Signalling, Fac Sci, Dept Chem, DK-1871 Copenhagen C, Denmark
Format: Article in Journal/Newspaper
Language:English
Published: Amer Cemical Soc 2015
Subjects:
In Vitro Techniques
Chitin
Acetylation
Iceland
Online Access:http://hdl.handle.net/2336/560815
https://doi.org/10.1021/acs.biomac.5b00163
Description
Summary:A highly efficient method for chemical modification of chitosan biopolymers by reductive amination to yield N,N-dialkyl chitosan derivatives was developed. The use of 3,6-O-di-tert-butyldimethylsilylchitosan as a precursor enabled the first 100% disubstitution of the amino groups with long alkyl chains. The corresponding mono N-alkyl derivatives were also synthesized, and all the alkyl compounds were then quaternized using an optimized procedure. These well-defined derivatives were studied for antibacterial activity against Gram positive S. aureus, E. faecalis, and Gram negative E. coli, P. aeruginosa, which could be correlated to the length of the alkyl chain, but the order was dependent on the bacterial strain. Toxicity against human red blood cells and human epithelial Caco-2 cells was found to be proportional to the length of the alkyl chain. The most active chitosan derivatives were found to be more selective for killing bacteria than the quaternary ammonium disinfectants cetylpyridinium chloride and benzalkonium chloride, as well as the antimicrobial peptides melittin and LL-37. Icelandic Research Fund 120443021 University of Iceland Research Fund Bergthoru og Thorsteins Schevings Thorsteinsson

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