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Azo-quaternary pyridinium salts with acid-enhanced antibacterial efficacy, methods of use, methods of syntheses, and uses thereof

A technology of quaternary pyridinium salts and azo compounds, applied in the direction of active ingredients of heterocyclic compounds, medical preparations of non-active ingredients, medical preparations containing active ingredients, etc.

Inactive Publication Date: 2019-06-21
ADA FOUND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, existing formulations of these salts failed to simultaneously exhibit high antibacterial potency against S. mutans and sensitivity to changing environmental pH

Method used

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  • Azo-quaternary pyridinium salts with acid-enhanced antibacterial efficacy, methods of use, methods of syntheses, and uses thereof
  • Azo-quaternary pyridinium salts with acid-enhanced antibacterial efficacy, methods of use, methods of syntheses, and uses thereof
  • Azo-quaternary pyridinium salts with acid-enhanced antibacterial efficacy, methods of use, methods of syntheses, and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Example 1. (E)-1-hexadecyl-4-((4-(methacryloyloxy)phenyl)diazenyl)-pyridinium bromide (named Azo-QPS-C16 )Synthesis.

[0023] General information on synthesis and characterization. Commercially available materials from Alfa Aesar (Tewksbury, MA, USA), Sigma-Aldrich (Saint Louis, MO, USA) and TCI America (Portland, OR, USA) were used as received. Proton and carbon nuclear magnetic resonance (1H and13CNMR) spectra were recorded on a Bruker instrument (600MHz, Billerica, MA, USA) using 5mm tubes. Chemical shifts are reported in parts per million (ppm, δ) relative to tetramethylsilane (δ = 0.00), dimethylsulfoxide (δ = 2.50) or chloroform (δ = 7.26). 1H NMR splitting patterns are assigned as singlet (s), doublet (d), triplet (t), quartet (q), dd (double doublet) and m (multiplet). High resolution mass spectra (MS) were recorded on a JEOL AccuTOF (Peabody, MA, USA) for ESI-TOF-MS analysis.

[0024] Azo-QPS-C16 is a smaller organic molecule. An exemplary synthesis proced...

Embodiment 2

[0028] Example 2. Acid Enhanced Antimicrobial Efficacy.

[0029] Azo-QPS-C16 is effective against both Gram-positive bacteria (Escherichia coli) and Gram-negative bacteria (Streptococcus mutans). The ability of bacteria to proliferate after exposure to Azo-QPS-C16 was characterized by adding growth medium and measuring optical density (OD) at 600 nm every 15 minutes in pH 4.1, 5.8 and 7.9 buffers. Exposure to 2.5 μg / mL of Azo-QPS-C16 at pH 4.1 completely inhibited E. coli growth for 19 hours. However, exposure at pH 7.9 required much higher concentrations (40 μg / mL) to inhibit cell growth. Significant growth of E. coli was observed for control assays containing all buffers at different pH values ​​with and without dimethylsulfoxide (DMSO). The pH dependence of the bactericidal activity of Azo-QPS-C16 in terms of minimum bactericidal concentration (MBC) was evaluated by plating the culture onto Lysogeny Broth (LB) agar plates after treating cells with two-fold serial dilution...

Embodiment 3

[0035] Example 3. Physicochemical properties of pH sensitivity.

[0036] Azo-QPS-C16 exhibited pH-sensitive physicochemical properties associated with its acid-enhanced antibacterial activity. Aqueous solutions of Azo-QPS-C16 (0.01 mmol / L, 5.7 μg / mL) were light orange and purple under acidic and basic conditions, respectively, which was consistent with the red shift observed in the UV–Vis spectrum. After baseline correction, UV-vis spectra were recorded on a Thermo Spectronic Genesys 5 UV-Vis spectrophotometer (Thermo Scientific, Waltham, MA USA) using a quartz cuvette with a 1 cm path length at 298K. The intensification of the peak centered at 554 nm and the simultaneous decrease of the peak at 347 nm are proportional to the pH change from 4.1 to 7.9. A similar absorption peak was detected in DMSO (0.05 mmol / L, 28.6 μg / mL) with the addition of a molar equivalent of a base such as triethylamine (TEA); the decrease in peak intensity at 347 nm was proportional to the molar rati...

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Abstract

A new azo-type quaternary pyridinium salt (Azo-QPS) shows enhanced activity at acidic conditions (e.g., pH = 5); in neutral or basic conditions, this new Azo-QPS shows a much lower level (2-50 times lower) anti-bacterial activity. The use of such a stimulus-enhance antibiotic can response to the proliferation of bacteria directly. It helps reduce or prevent the build-up of potent antibacterial agents in the oral environment. The antibacterial properties of Azo-QPS are activated when the environmental pH becomes acidic; this acidic pH may be indicative of the accumulation of Streptococcus mutans, or the initiation of tooth decay.

Description

Background technique [0001] Antimicrobial resistance is the ability of a microorganism to resist the effects of a drug previously used to treat that microorganism. More narrowly, antimicrobial resistance (sometimes called antimicrobial resistance or antibiotic resistance) refers to the resistance of bacteria to antibiotics. This type of antibiotic resistance is a current threat to every region of the world and has the potential to affect anyone, of any age, in any country, according to the World Health Organization. Antibiotic resistance, therefore, is now a major threat to public health when bacteria change so that antibiotics are no longer effective in the people who need them to treat infections. [0002] In the oral environment, Streptococcus mutans is the main pathogen of dental caries formation. S. mutans is able to survive and multiply in an acidic / low pH (down to pH 4) oral environment. In fact, in the oral environment, a sufficiently acidic pH indicates the accumul...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C245/06A61K31/655
CPCC07D213/76C08F220/34A61P1/02A61P31/04A61K47/56A61K31/44G01N33/5438G01N33/6887G01N33/84G01N2333/78C07D213/20C08F226/06C08F26/06C08F126/06
Inventor 孙继润
Owner ADA FOUND
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