Synthesis of N,N,N-trimethyl chitosan homopolymer and highly substituted N-alkyl-N,N-dimethyl chitosan derivatives with the aid of di-tert-butyldimethylsilyl chitosan

Benediktsdóttir, Berglind Eva; Gaware, Vivek S.; Rúnarsson, Ögmundur Vidar; Jónsdóttir, Sigríður; Jensen, Knud J.; Másson, Már

doi:10.1016/j.carbpol.2011.06.007

Cited by 68 publications

(63 citation statements)

References 30 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…22 On the other hand, the conventional procedure for reductive mono-and dialkylation, based on reductive alkylation in acidic aqueous medium, results in a decrease in the DS as the alkyl chain length increases from methyl onwards. 13,29,30 In the current study, monoalkyl chitosan derivatives with ethyl, butyl, and hexyl chains were synthesized using this precursor.…”

Section: 1mentioning

confidence: 99%

“…As a control, the dialkylation reaction was also performed on 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 NMP. 22 The products were then purified by dialysis in order to remove the excess reagents and side products. In cases where traces of silyl groups were retained, the deprotection procedure was repeated once more.…”

Section: 1mentioning

confidence: 99%

“…Quaternization of these alkylated products also resulted in highly substituted products. 22 In general, it has been concluded that hydrophobicity tends to increase antibacterial activity; however, a detailed study of well-characterized quaternary chitosan derivatives, showing the degree of hydrophobicity required for optimum activity against various bacterial species, has not previously been reported.…”

Section: Introductionmentioning

confidence: 98%

See 2 more Smart Citations

Impact of Chain Length on Antibacterial Activity and Hemocompatibility of Quaternary N-Alkyl and N,N-Dialkyl Chitosan Derivatives

et al. 2015

Self Cite

View full text Add to dashboard Cite

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.

show abstract

Section: 1mentioning

confidence: 99%

Section: 1mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 98%

See 1 more Smart Citation

Impact of Chain Length on Antibacterial Activity and Hemocompatibility of Quaternary N-Alkyl and N,N-Dialkyl Chitosan Derivatives

et al. 2015

Self Cite

View full text Add to dashboard Cite

show abstract

“…Several methodologies concerning the TMC synthesis are depicted in the ( Figure 1). Among these, the highlighted methodologies were proposed by Sieval et al, Verheul et al, De Brito and Assis, and Benediktsdottir et al (Figure 1) [2][3][4][5].…”

Section: Introductionmentioning

confidence: 99%

“…On the other hand, Bendiktsdottir et al [5] synthesized a fully quaternized TMC from protection strategies toward -OH groups (using the tertbutyldimethylsilyl -TBDMS protection group and tetrabutylammonium fluoride (TBAF) as desprotetor agent), avoiding O-methylation ( Figure 1). The Figure 1 will be further discussed in the following sections.…”

Section: Introductionmentioning

confidence: 99%

N,N,N-Trimethyl Chitosan and Its Potential Bactericidal Activity: Current Aspects and Technological Applications

Facchi¹,

Facchi²

2016

J Infect Dis Ther

View full text Add to dashboard Cite

N,N,N-Trimethyl chitosan (TMC) is one of most important chitosan derivative with stronger bactericidal property. Currently, the TMC has been attracted considerable attention, because it contains quaternized ammonium moieties ( -+ N(CH 3 ) 3 ) in its network. Its cationic property leads to a renowned bactericidal power. Besides, TMC has appropriate biocompatibility, biodegradability, mucoadhesive capacity and greater solubility at pH close to physiological condition regarding chitosan. In this way, there are not sources regarding revision papers toward TMC bactericidal action. So, this revision work reports the TMC potential to be applied in many fields, depicting its bactericidal performance, as well as, its bactericidal mechanism and some current technological aspects that must be considered.

show abstract

Chitosan and Trimethyl Chitosan (TMC) as Drug Absorption Enhancers

Benediktsdóttir

2020

Encyclopedia of Marine Biotechnology

View full text Add to dashboard Cite

Synthesis of N,N,N-trimethyl chitosan homopolymer and highly substituted N-alkyl-N,N-dimethyl chitosan derivatives with the aid of di-tert-butyldimethylsilyl chitosan

Cited by 68 publications

References 30 publications

Impact of Chain Length on Antibacterial Activity and Hemocompatibility of Quaternary N-Alkyl and N,N-Dialkyl Chitosan Derivatives

Impact of Chain Length on Antibacterial Activity and Hemocompatibility of Quaternary N-Alkyl and N,N-Dialkyl Chitosan Derivatives

N,N,N-Trimethyl Chitosan and Its Potential Bactericidal Activity: Current Aspects and Technological Applications

Chitosan and Trimethyl Chitosan (TMC) as Drug Absorption Enhancers

Contact Info

Product

Resources

About