TY - JOUR
T1 - Synthesis, Characterization, and Antimicrobial Investigation of a Novel Chlorhexidine Cyclamate Complex
AU - Dubovoy, Viktor
AU - Desai, Primit
AU - Hao, Zhigang
AU - Cheng, Chi Yuan
AU - Verma, Gaurav
AU - Wojtas, Lukasz
AU - Brinzari, Tatiana V.
AU - Boyd, Jeffrey M.
AU - Ma, Shengqian
AU - Asefa, Tewodros
AU - Pan, Long
N1 - Publisher Copyright:
Copyright © 2020 American Chemical Society.
Copyright:
Copyright 2020 Elsevier B.V., All rights reserved.
PY - 2020/8/5
Y1 - 2020/8/5
N2 - 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 among 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. Furthermore, substitution of inactive gluconate with bioactive cyclamate counterion potentially provides the additional benefit of improving the taste profile of chlorhexidine.
AB - 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 among 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. Furthermore, substitution of inactive gluconate with bioactive cyclamate counterion potentially provides the additional benefit of improving the taste profile of chlorhexidine.
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U2 - 10.1021/acs.cgd.0c00107
DO - 10.1021/acs.cgd.0c00107
M3 - Article
AN - SCOPUS:85091510330
VL - 20
SP - 4991
EP - 4999
JO - Crystal Growth and Design
JF - Crystal Growth and Design
SN - 1528-7483
IS - 8
ER -