Synthesis and antimicrobial activity of polymeric guanidine and biguanidine salts

Zhang, Yumei; Jiang, Jianming; Chen, Yanmo

doi:10.1016/s0032-3861(98)00828-3

Cited by 198 publications

(114 citation statements)

References 9 publications

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“…Fig. 7, is a widely used environmental biocide and contact lens disinfectant that has been demonstrated to have antifungal activity as well [74,75]. Several early antimicrobial studies on this cationic polymer appeared in the 1980's.…”

Section: Biocidal Cationic Polymersmentioning

confidence: 99%

Infectious disease: Connecting innate immunity to biocidal polymers

Gabriel

Som

Madkour

et al. 2007

Materials Science and Engineering: R: Reports

251

258

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Infectious disease is a critically important global healthcare issue. In the U.S. alone there are 2 million new cases of hospital-acquired infections annually leading to 90,000 deaths and 5 billion dollars of added healthcare costs. Couple these numbers with the appearance of new antibiotic resistant bacterial strains and the increasing occurrences of community-type outbreaks, and clearly this is an important problem. Our review attempts to bridge the research areas of natural host defense peptides (HDPs), a component of the innate immune system, and biocidal cationic polymers. Recently discovered peptidomimetics and other synthetic mimics of HDPs, that can be short oligomers as well as polymeric macromolecules, provide a unique link between these two areas. An emerging class of these mimics are the facially amphiphilic polymers that aim to emulate the physicochemical properties of HDPs but take advantage of the synthetic ease of polymers. These mimics have been designed with antimicrobial activity and, importantly, selectivity that rivals natural HDPs. In addition to providing some perspective on HDPs, selective mimics, and biocidal polymers, focus is given to the arsenal of biophysical techniques available to study their mode of action and interactions with phospholipid membranes. The issue of lipid type is highlighted and the important role of negative curvature lipids is illustrated. Finally, materials applications (for instance, in the development of permanently antibacterial surfaces) are discussed as this is an important part of controlling the spread of infectious disease.

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Section: Biocidal Cationic Polymersmentioning

confidence: 99%

Infectious disease: Connecting innate immunity to biocidal polymers

Gabriel

Som

Madkour

et al. 2007

Materials Science and Engineering: R: Reports

251

258

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“…12 Guanidinium salts have attracted increasing interest in recent years, the guanidine derivatives with antimicrobial and antifungal activity have been investigated as medical and crop protection agents and antiseptics for industry products, food and other goods for daily use. [13][14][15][16][17][18] Few studies have investigated the feasibility of guanidinylated chitosan. 19 Therefore, possibility of guanidinylated chitosan with multi-amino groups seemed attractive.…”

mentioning

confidence: 99%

Synthesis and Characterization of Chitosan Biguanidine Hydrochloride under Microwave Irradiation

Zhao

Yi-zhen³

2009

Polym. J.

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Chitosan biguanidine hydrochloride was synthesized by reacting chitosan with dicyandiamide under microwave irradiation. The influence of reaction temperature, reaction solvent and microwave heating time was studied, and optimal conditions were identified. The representative microwave synthesized chitosan biguanidine hydrochloride was characterized by Fourier transform infrared spectroscopy, scanning electron microscopy and X-ray diffraction measurement, taking chitosan as a reference. The solubility pH for the chitosan biguanidine hydrochloride with different substitution degrees was monitored. The antimicrobial activities of chitosan biguanidine hydrochloride were measured by means of the minimal inhibition concentration (MIC). In vitro antimicrobial activity of guanidinylated chitosans with different substitution degrees were evaluated against staphylococcus aureus, bacillus subtilis, escherichia coli and pseudomonas aeruginosa. The results show that the microwave irradiation method can increase the reaction rate by twelve times over the conventional method. Chitosan biguanidine hydrochloride are effective of bacteriostasis, compared with chitosan, guanidinylated chitosan had much better antibacterial activity. The antibacterial activity of chitosan biguanidine hydrochloride derivative enhanced with increasing substitution degrees of guanidinylated chitosan.

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“…The main active ingredient in the AKWATON-based disinfectant tested is PHMGH. Zhang et al (1999) reported that PHMGH is effective in controlling bacteria and fungi. The bactericidal mechanism of PHMGH has been extensively documented.…”

Section: Resultsmentioning

confidence: 99%

Fungicidal activity of AKWATON and in vitro assessment of its toxic effects on animal cells

Oulé

Staines

Lightly

et al. 2015

Journal of Medical Microbiology

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Acquired superficial fungal infections are among the most common infections. It is necessary to create new effective and non-toxic disinfectants. AKWATON is a new disinfectant of the polymeric guanidine family. Its fungicidal activity against Trichophyton mentagrophytes and its in vitro toxicity assessment were determined in this study. The MIC, minimum fungicidal concentration (MFC) and time required for its fungicidal activity at the MFC were evaluated using the official methods of analysis of the Association of Official Analytical Chemists, with modifications as recommended by the Canadian General Standards Board. The toxic effects of AKWATON and of four commercial disinfectants were evaluated on rat pancreatic (C2C12) and muscle (RnM5F) cells, using the trypan blue and MTT [3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide] methods. The MIC, MFC and time required for the fungicidal activity of AKWATON at the MFC were 0.025 % (w/v), 0.045 % (w/v) and 2.5 min, respectively. Cell cultures and the different tests carried out showed that the AKWATON-based disinfectant killed fewer cells than the commercial disinfectants, sparing 80 % of C2C12 cells and 65 % of RnM5F cells, whilst some of the well-known disinfectants currently on the market killed 85-100 % of cells. This study demonstrates that AKWATON has great potential as an odourless, colourless, non-corrosive and safe disinfectant for use in hospitals, the agriculture industry, farming and household facilities.

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Synthesis and antimicrobial activity of polymeric guanidine and biguanidine salts

Cited by 198 publications

References 9 publications

Infectious disease: Connecting innate immunity to biocidal polymers

Infectious disease: Connecting innate immunity to biocidal polymers

Synthesis and Characterization of Chitosan Biguanidine Hydrochloride under Microwave Irradiation

Fungicidal activity of AKWATON and in vitro assessment of its toxic effects on animal cells

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