Novel anionic surfactant-modified chlorhexidine and its potent antimicrobial properties

Zilma Pereira Muneeswaran; Baran Teoman; Yu Wang; Haroon Chaudhry; Tatiana V. Brinzari; Gaurav Verma; Lomaani Ranasinghe; Kylie Ryan Kaler; Xiaoyi Huang; Xing He; Belvin Thomas; Shiyou Xu; Chi-Yuan Cheng; Jeffrey M. Boyd; Dailin Chen; Zhigang Hao; Shengqian Ma; Tewodros Asefa; Long Pan; Viktor Dubovoy

doi:10.1039/D3DT02559D

Novel anionic surfactant-modified chlorhexidine and its potent antimicrobial properties†

Zilma Pereira Muneeswaran,

^ac Baran Teoman,

^ae Yu Wang,^ac Haroon Chaudhry,^ac Tatiana V. Brinzari,^a Gaurav Verma,^f Lomaani Ranasinghe,^g Kylie Ryan Kaler,^g Xiaoyi Huang,^b Xing He,^b Belvin Thomas,

^c Shiyou Xu,^a Chi-Yuan Cheng,^a Jeffrey M. Boyd,

^g Dailin Chen,^b Zhigang Hao,

^a Shengqian Ma,

^f Tewodros Asefa,

^cd Long Pan

*^a and Viktor Dubovoy

*^a

Author affiliations

* Corresponding authors

^a Colgate-Palmolive Company, 909 River Road, Piscataway, New Jersey 08854, USA
E-mail: vdubovoy@gmail.com

^b Colgate-Palmolive Company, 338 Qingnian Road, Economic Development Zone, Guangzhou 510620, China

^c Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, 610 Taylor Road, Piscataway, New Jersey 08854, USA

^d Department of Chemical and Biochemical Engineering, Rutgers, The State University of New Jersey, 98 Brett Road, Piscataway, New Jersey 08854, USA

^e Otto H. York Department of Chemical and Materials Engineering, New Jersey Institute of Technology, 323 Dr. Martin Luther King Jr Boulevard, Newark, New Jersey 07102, USA

^f Department of Chemistry, University of North Texas, 1508 W. Mulberry Street, Denton, Texas 76201, USA

^g Department of Biochemistry and Microbiology, Rutgers, The State University of New Jersey, 76 Lipman Drive, New Brunswick, New Jersey 08901, USA

Abstract

Chlorhexidine dodecyl sulfate (CHX-DS) was synthesized and characterized via single-crystal X-ray diffraction (SC-XRD), ¹H nuclear magnetic resonance (NMR) spectroscopy, ¹H nuclear Overhauser effect spectroscopy (NOESY), and attenuated total reflectance Fourier-transform infrared spectroscopy (ATR-FTIR). The solid-state structure, comprising a 1 : 2 stoichiometric ratio of chlorhexidine cations [C₂₂H₃₀Cl₂N₁₀]²⁺ to dodecyl sulfate anions [C₁₂H₂₅SO₄]⁻, is the first report of chlorhexidine isolated with a surfactant. CHX-DS exhibits broad-spectrum antibacterial activity and demonstrates superior efficacy for reducing bacteria-generated volatile sulfur compounds (VSCs) as compared to chlorhexidine gluconate (CHG). The minimum inhibitory concentrations (MICs) of CHX-DS were 7.5, 2.5, 2.5, and 10 μM for S. enterica, E. coli, S. aureus, and S. mutans, respectively. Furthermore, MIC assays for E. coli and S. mutans demonstrate that CHX-DS and CHX exhibit a statistically significant efficacy enhancement in 2.5 μM treatment as compared to CHG. CHX-DS was incorporated into SBA-15, a mesoporous silica nanoparticle (MSN) framework, and its release was qualitatively measured via UV-vis in aqueous media, which suggests its potential as an advanced functional material for drug delivery applications.

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Novel anionic surfactant-modified chlorhexidine and its potent antimicrobial properties†

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