Viktor Dubovoy1,2, Primit Desai3, Zhigang Hao1, Chi-Yuan Cheng1, Gaurav Verma4, Lukasz Wojtas4, Tatiana V Brinzari1, Jeffrey M Boyd3, Shengqian Ma4, Tewodros Asefa2,5, Long Pan1. 1. Colgate-Palmolive Company, 909 River Road, Piscataway, New Jersey 08854, United States. 2. Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, 610 Taylor Road, Piscataway, New Jersey 08854, United States. 3. Department of Biochemistry and Microbiology, Rutgers, The State University of New Jersey, 76 Lipman Drive, New Brunswick, New Jersey 08901, United States. 4. Department of Chemistry, University of South Florida, 4202 East Fowler Avenue, Tampa, Florida 33620, United States. 5. Department of Chemical and Biochemical Engineering, Rutgers, The State University of New Jersey, 98 Brett Road, Piscataway, New Jersey 08854, United States.
Abstract
The synthesis, crystal structure, and antimicrobial efficacy are reported for a novel material comprising a 1:2 ratio of chlorhexidine (CHX) to N-cyclohexylsulfamate (i.e., artificial sweetener known as cyclamate). The chemical structure is unambiguously identified by incorporating a combination of single-crystal X-ray diffraction (SC-XRD), electrospray ionization mass spectrometry (ESI-MS), 1H nuclear magnetic resonance (NMR) spectroscopy, correlation spectroscopy (COSY), and attenuated total reflection Fourier-transform infrared spectroscopy (ATR-FTIR). The new material: 1) is amongst only several reported structures identified to date incorporating the vital chlorhexidine antimicrobial drug; 2) exhibits broad spectrum antimicrobial activity at concentrations less than 15 μg/mL; and 3) provides a unique delivery method for the essential active pharmaceutical ingredient (API). Furthermore, substitution of inactive gluconate with bioactive cyclamate counterion potentially provides the additional benefit of improving the taste profile of chlorhexidine.
The synthesis, crystal structure, and antimicrobial efficacy are reported for a novel material comprising a 1:2 ratio of chlorhexidine (n class="Chemical">CHX) to N-cyclohexylsulfamate (i.e., artificial sweetener known as cyclamate). The chemical structure is unambiguously identified by incorporating a combination of single-crystal X-ray diffraction (SC-XRD), electrospray ionization mass spectrometry (ESI-MS), 1H nuclear magnetic resonance (NMR) spectroscopy, correlation spectroscopy (COSY), and attenuated total reflection Fourier-transform infrared spectroscopy (ATR-FTIR). The new material: 1) is amongst only several reported structures identified to date incorporating the vital chlorhexidine antimicrobial drug; 2) exhibits broad spectrum antimicrobial activity at concentrations less than 15 μg/mL; and 3) provides a unique delivery method for the essential active pharmaceutical ingredient (API). Furthermore, substitution of inactive gluconate with bioactive cyclamate counterion potentially provides the additional benefit of improving the taste profile of chlorhexidine.
Authors: Tara Rema; John R Lawrence; James J Dynes; Adam P Hitchcock; Darren R Korber Journal: Antimicrob Agents Chemother Date: 2014-07-14 Impact factor: 5.191
Authors: Viktor Dubovoy; Anjani Ganti; Tao Zhang; Hassan Al-Tameemi; Juan D Cerezo; Jeffrey M Boyd; Tewodros Asefa Journal: J Am Chem Soc Date: 2018-10-04 Impact factor: 15.419
Authors: Christina A Roberts; Hassan M Al-Tameemi; Ameya A Mashruwala; Zuelay Rosario-Cruz; Unnati Chauhan; William E Sause; Victor J Torres; William J Belden; Jeffrey M Boyd Journal: Infect Immun Date: 2017-05-23 Impact factor: 3.441