STUDIES ON ^|^ldquo;MACRAMIN^|^rdquo;, A NEW HIGH-MOLECULAR ANTIBACTERIAL SUBSTANCE DERIVED FROM CHITIN*

Hatta, Sadayoshi; Kuwabara, Shogo; Miyamoto, Haruo; Aoyama, Kosaku; Utsunomiya, Norihisa; Tanji, Sonoe

doi:10.7883/yoken1948.3.119

Cited by 8 publications

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“…On the other hand, chitin derivatives are not in widespread use as wound dressings, and relevant studies on wound healing have been confined to a few recent articles (1, 11). Interestingly, some antibacterial and antifungal activities have been described with chitosan and modified chitosans (5,8,9,18).N-Carboxybutyl chitosan is more versatile than any other polysaccharide currently used in wound management and lends itself to the manufacture of wound dressings with peculiar characteristics. Such dressings, in particular, can stimulate ordered regeneration (3) and vascularization (10) of tissue and allow gaseous exchange and turn into a gel form when they are in contact with body fluids (14), thus permitting dressing removal without disturbing the newly formed tissues.…”

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Antimicrobial properties of N-carboxybutyl chitosan

Müzzarelli

Tarsi

Filippini

et al. 1990

Antimicrob Agents Chemother

404

199

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N-Carboxybutyl chitosan, a modified chitin of crustacean origin, displayed inhibitory, bactericidal, and candidacidal activities when tested against 298 cultures of various pathogens. Examination by electron microscopy showed that microbial cells exposed to N-carboxybutyl chitosan underwent marked morphological alterations. The data are of importance in defining the suitability of N-carboxybutyl chitosan as a wound dressing.A number of polysaccharides, mainly cross-linked dextran, calcium alginate, carboxymethyl starch, modified agar, and carboxymethyl cellulose, are used in wound treatment (13,17). These polysaccharides, however, do not seem to combine favorable physical forms with functional properties; rather, besides the hemostatic action of oxycellulose, no functional property has been reported (17). The same is true for gelatin and collagen (15). On the other hand, chitin derivatives are not in widespread use as wound dressings, and relevant studies on wound healing have been confined to a few recent articles (1, 11). Interestingly, some antibacterial and antifungal activities have been described with chitosan and modified chitosans (5,8,9,18).N-Carboxybutyl chitosan is more versatile than any other polysaccharide currently used in wound management and lends itself to the manufacture of wound dressings with peculiar characteristics. Such dressings, in particular, can stimulate ordered regeneration (3) and vascularization (10) of tissue and allow gaseous exchange and turn into a gel form when they are in contact with body fluids (14), thus permitting dressing removal without disturbing the newly formed tissues. We undertook the present study to define the antimicrobial properties of N-carboxybutyl chitosan and to test it in different physical forms in view of its use in wound management. N-Carboxybutyl chitosan, which was prepared from crustacean chitosan (degree of deacetylation, 0.73) according to a proprietary procedure (R. Muzzarelli, U.S. patent 4,835,265, June 1986) and as described previously (12, 14), was tested against a variety of gram-positive and gramnegative pathogens and Candida spp. A total of 298 strains were used, all of which were freshly isolated from clinical material and identified according to conventional laboratory criteria.Two different methods were used to assess the antimicrobial activity of N-carboxybutyl chitosan. The first method was a quantitative assay based on conventional agar dilution tests (20), with final concentrations being 2, 4, 6, 8, and 9 mg/ml (concentrations above 9 mg/ml did not permit full solubilization of N-carboxybutyl chitosan into the test medium). The inoculum suspensions were prepared from fresh broth cultures and adjusted to obtain a concentration of approximately 107 CFU/ml. Test plates were inoculated by using an automatic replicating device (Titertek; Flow Labo-* Corresponding author. ratories, Inc., McLean, Va.) that delivered 1 1.l of bacterial suspension per spot. A control plate with no N-carboxybutyl chitosan was inoculated first, and a second co...

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confidence: 99%

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confidence: 99%

Antimicrobial properties of N-carboxybutyl chitosan

Müzzarelli

Tarsi

Filippini

et al. 1990

Antimicrob Agents Chemother

404

199

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“…TMC was first synthesized by Terayama, H. and Terayama, E. [45] and it was called Macramin. Its antibacterial activity was first reported by Hatta et al [46]. Much later experiments carried out by Muzzarelli and Tanfani [47] were able to produce TMC through different steps, but the compound displayed low water solubility.…”

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confidence: 92%

An Overview of Current Knowledge on the Properties, Synthesis and Applications of Quaternary Chitosan Derivatives

et al. 2020

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Chitosan, a chitin-derivative polysaccharide, known for its non-toxicity, biocompatibility and biodegradability, presents limited applications due to its low solubility in neutral or basic pH medium. Quaternization stands out as an alternative to modify this natural polymer, aiming to improve its solubility over a wide pH range and, consequently, expand its range of applications. Quaternization occurs by introducing a quaternary ammonium moiety onto or outside the chitosan backbone, via chemical reactions with primary amino and hydroxyl groups, under vast experimental conditions. The oldest and most common forms of quaternized chitosan involve N,N,N-trimethyl chitosan (TMC) and N-[(2-hydroxy-3-trimethyl ammonium) propyl] chitosan (HTCC) and, more recently, quaternized chitosan by insertion of pyridinium or phosphonium salts. By modifying chitosan through the insertion of a quaternary moiety, permanent cationic charges on the polysaccharide backbone are achieved and properties such as water solubility, antimicrobial activity, mucoadhesiveness and permeability are significantly improved, enabling the application mainly in the biomedical and pharmaceutical areas. In this review, the main quaternized chitosan compounds are addressed in terms of their structure, properties, synthesis routes and applications. In addition, other less explored compounds are also presented, involving the main findings and future prospects regarding the field of quaternized chitosans.

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Antimicrobial Properties of Chitosan and Its Derivatives

Másson

2021

Advances in Polymer Science

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STUDIES ON ^|^ldquo;MACRAMIN^|^rdquo;, A NEW HIGH-MOLECULAR ANTIBACTERIAL SUBSTANCE DERIVED FROM CHITIN*

Cited by 8 publications

References 0 publications

Antimicrobial properties of N-carboxybutyl chitosan

Antimicrobial properties of N-carboxybutyl chitosan

An Overview of Current Knowledge on the Properties, Synthesis and Applications of Quaternary Chitosan Derivatives

Antimicrobial Properties of Chitosan and Its Derivatives

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