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Synthesis, Characterization, and Antimicrobial Investigation of a Novel Chlorhexidine Cyclamate Complex.

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.

SUBMITTER: Dubovoy V

PROVIDER: S-EPMC8159181 | biostudies-literature | 2020 Aug

REPOSITORIES: biostudies-literature

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Synthesis, Characterization, and Antimicrobial Investigation of a Novel Chlorhexidine Cyclamate Complex.

Dubovoy Viktor V Desai Primit P Hao Zhigang Z Cheng Chi-Yuan CY Verma Gaurav G Wojtas Lukasz L Brinzari Tatiana V TV Boyd Jeffrey M JM Ma Shengqian S Asefa Tewodros T Pan Long L

Crystal growth & design 20200504 8

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>i.e.</i>, 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), <sup>1</sup>H nuclear magnetic resonance (NMR) spectroscopy, correlation spectroscopy (COSY), and ...[more]

PMID: 34054352

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Project description:Chlorhexidine belongs to a group of medicines called antiseptic antibacterial agents. Chlorhexidine is commonly used for the care and clean off the skin, hands, and wounds. In recent years, medicinal and aromatic plants have been used for prevention of disease, maintaining health, and improving disease in traditional and modern medicine as a medicament. According to recent research, cineole is the isolated active agent of eucalyptus oil and possesses antimicrobial activity. It was demonstrated that cineole could enhance the antimicrobial effects of the other antiseptics.The aim of this study was to investigate the efficacy of 1,8-cineole on the antimicrobial effect of chlorhexidine against some microorganisms.The effect of 1,8-cineole on antimicrobial activity of chlorhexidine gluconate (CHG) was tested using seven different microorganisms. In this study, CHG (128-0.125 mg/l) and cineole (512-2 g/l) were analyzed together and separately using checkerboard assay. Interactions between CHG and 1,8-cineole have been identified as synergistic, indifferent, or antagonistic.Synergistic activity was demonstrated between CHG and 1,8-cineole against Staphylococcus aureus, methicillin-resistant S. aureus, Escherichia coli, Klebsiella pneumoniae, Enterococcus faecalis, and Candida albicans. Indifferent interactions for these compounds were demonstrated against Pseudomonas aeruginosa.CHG antiseptic properties were found to be increased when CHG was used in combination with 1,8-cineole. In this way, CHG will reveal stronger effect against microorganisms.Cineole has increased the antimicrobial activity of chlorhexidine gluconate against all microorganisms except Pseudomonas aeruginosaIn topical application, using cineole in combination with chlorhexidine may be easier, eradicate certain resistant bacteria by increasing the antimicrobial efficacy. Abbreviation Used: CHG: Chlorhexidine gluconate, MRSA: Methicillin-resistant S. aureus, MHB: Mueller Hinton broth, SDB: Sabouraud dextrose broth, CFU: Colonyforming unit, FIC: Fractional inhibitory concentration, FICI: FIC index, EO: Eucalyptus oil.

Project description:The goal of this study was to synthesize and evaluate new antimicrobial compounds. We specifically focused on the development of 2,5-disubstituted tetrazole derivatives containing the O-methyl-2,3-O-isopropylidene-(D)-ribofuranoside groups through N-alkylation reactions. The synthesized compounds were characterized using 1H and 13C nuclear magnetic resonance (NMR) spectroscopy. Their antibacterial activity was tested against Pseudomonas aeruginosa, Escherichia coli, Streptococcus fasciens, and Staphylococcus aureus. Density functional theory (DFT) was applied to examine the electronic properties, including the highest occupied molecular orbital (HOMO)-least unoccupied molecular orbital (LUMO) gap, hardness, softness, density of states (DOS), and molecular electrostatic potential. Additionally, crystal structure modeling of protein 7AZ5 was performed to study the binding affinities through hydrophobic interactions and hydrogen bonding. Molecular dynamics simulations were carried out for 100 ns and OPLS_2005 force field re performed to investigate the stability of 3c and 5c into 7AZ5 binding site. Root-mean-square deviation (RMSD), root mean square fluctuation (RMSF), and intermolecular interactions analysis showed that these two compounds may gave relative stability into the 7AZ5 binding site. Several of the N-ribofuranosyl tetrazole derivatives synthesized displayed a strong antibacterial activity. Compounds 1c and 5c were particularly effective, with a minimum inhibitory concentration (MIC) of 15.06 μM and 13.37 μM, respectively, against E. coli and S. aureus both surpassing the efficacy of chloramphenicol (19.34 μM) and ampicillin (28.62 μM). These compounds also displayed the highest binding energies in protein modeling, indicating strong interactions with the DNA polymerase sliding clamp of E. coli. Compounds 1c and 5c show promise as potent antibacterial agents with notable chemical stability and favorable binding profiles. These findings suggest that these derivatives may serve as valuable leads for the development of new antimicrobial drugs.

Dataset Information

Synthesis, Characterization, and Antimicrobial Investigation of a Novel Chlorhexidine Cyclamate Complex.

Publications

Synthesis, Characterization, and Antimicrobial Investigation of a Novel Chlorhexidine Cyclamate Complex.

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