Structural Characterization and Bacteriostatic and Cytotoxicity to 3T3 Cells Study of Oligobiguanidine (Polyhexamethylene Biguanidine Hydrochloride) and its 3-Glycidoxypropyltrimethoxysilane Derivatives

Abstract

In this paper, polyhexamethylene biguanidine hydrochloride (PHMB) oligomers were prepared by polycondensation of hexamethylenediamine, hydrochloric acid and 1,6-hexamethylenebis(dicyanamide); the organosilicon derivatives of PHMB oligomers (PHMB-Si) were prepared in solution through the reaction of PHMB and 3-Glycidoxypropyltrimethoxysilane (GLYMO). The analyses of FT-IR, 1 H and 13 C-NMR, elemental analysis, and TGA showed that the PHMB-Si was synthesized successfully. The relationship between antibiotic activity and viscosity-average molecular weight of PHMB; the relationship between antibiotic activity and the content of organosilicon in PHMB-Si were investigated. The experimental results revealed that the antibacterial activity of PHMB yielded the maximum at the viscosity-average molecular weight of 9000. The higher ratio of GLMYO in PHMB-Si, the higher antibiotic activity of PHMB-Si was. The minimal bactericidal concentration (MBC) of PHMB was 10 ppm, and the MBC of PHMB-Si was 5 ppm. The results showed there was an obvious synergy of PHMB-Si in bacteriostatic activity than PHMB.

Multifunctional Magnetic Porous Microspheres for Highly Efficient and Recyclable Water Disinfection and Dye Removal

“…To further verify the successful grafting, the chemical structures of PMS, PHMB, and PHMB- g -PMS were examined by FTIR spectroscopy. As presented in Figure A, compared with PMS, a new characteristic peak at 2120 cm –1 appeared in the spectrum of PHMB- g -PMS, corresponding to the stretching vibration of the cyano (R–CN) terminal group of PHMB, which shifted from 2060 cm –1 . Besides, the peak intensity at 1645 cm –1 belonging to the stretching vibrations of CO in the amide group increased obviously, which was attributed to the reaction of amino in PHMB and carboxyl in PMS, demonstrating the successful synthesis of PHMB- g -PMS.…”

Poly(hexamethylene biguanide) hydrochloride (PHMB)-based materials: synthesis, modification, properties, determination, and application

“…[31][32][33] For example, Jiang and coworkers prepared an organosilicon derivative of PHMB (PHMB-Si) in a solution via reaction with 3-glycidoxypropyltrimethoxysilane to improve its antibiotic activity (Scheme 4(i)). 34 The minimal bactericidal concentration of PHMB derivative was double the concentration of PHMB alone due to the presence of GLMYO. Zhi and colleagues developed a dual-functional antimicrobial and antifouling coating strategy by conjugating PHMB with allyl-terminated polyethylene glycol (allyloxy polyethylene glycol) (Scheme 4(ii)).…”