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Development of a novel expression, ZI MAX/K ZI, for determination of the counter-anion effect on the antimicrobial activity of tetrabutylammonium salts.

Bioorganic & medicinal chemistry letters (2009-08-08)
Michelle L Ingalsbe, Jeffrey D St Denis, Megan E McGahan, Walter W Steiner, Ronny Priefer
ABSTRACT

Due to the increasing number of strains of drug-resistant bacteria, the development of new antibiotics has become increasingly important. The antibacterial properties of quaternary amines and their derivatives on both Gram-positive and Gram-negative bacteria are well known. However, an encompassing study with specific emphasis on the role of the counter-anion has not been reported in the literature. By monitoring the Zone of Inhibition of various concentrations of tetrabutylammonium (TBA) salts, we observed that the counter anion plays a significant role in activity. We developed a novel method of reporting activity using zone of inhibition tests (ZI(MAX)/K(ZI)) and found it to be strongly correlated with the minimum inhibitory concentration (MIC).

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Tetrabutylammonium fluoride solution, 1.0 M in THF
Supelco
Tetrabutylammonium hydroxide solution, ~40% in water, suitable for ion chromatography
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Tetrabutylammonium hydroxide solution, 40 wt. % in H2O
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Tetrabutylammonium hydrogensulfate, 97%
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Tetrabutylammonium hydroxide solution, 1.0 M in methanol
Sigma-Aldrich
Tetrabutylammonium bromide, ACS reagent, ≥98.0%
Sigma-Aldrich
Tetrabutylammonium phosphate monobasic, puriss., ≥99.0% (T)
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Tetrabutylammonium chloride, ≥97.0% (NT)
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Tetrabutylammonium bisulfate, puriss., ≥99.0% (T)
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Tetrabutylammonium iodide, reagent grade, 98%
Sigma-Aldrich
Tetrabutylammonium tetrafluoroborate, 99%
Sigma-Aldrich
Tetrabutylammonium acetate, 97%
Supelco
Tetrabutylammonium perchlorate, for electrochemical analysis, ≥99.0%
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Tetrabutylammonium bisulfate, suitable for ion pair chromatography, LiChropur, ≥99.0%
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Tetrabutylammonium cyanide, 95%
Sigma-Aldrich
Tetrabutylammonium phosphate monobasic solution, 1.0 M in H2O
Sigma-Aldrich
Tetrabutylammonium hydroxide solution, technical, ~40% in H2O (~1.5 M)
Supelco
Tetrabutylammonium bromide, suitable for ion pair chromatography, LiChropur, ≥99.0%
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Tetrabutylammonium chloride, suitable for ion pair chromatography, LiChropur, ≥99.0%
Sigma-Aldrich
Tetrabutylammonium hydroxide solution, 54.0-56.0% in H2O
Sigma-Aldrich
Tetrabutylammonium fluoride solution, 75 wt. % in H2O
Sigma-Aldrich
Tetrabutylammonium acetate, technical, ≥90% (T)
Supelco
Tetrabutylammonium bisulfate solution, suitable for ion pair chromatography, LiChropur, concentrate, ampule
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Tetrabutylammonium acetate, for electrochemical analysis, ≥99.0%
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Tetrabutylammonium bromide solution, 50 wt. % in H2O
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Tetrabutylammonium acetate solution, 1.0 M in H2O
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Tetrabutylammonium fluoride on silica gel, ~1.5 mmol/g (F-)
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Tetrabutylammonium iodide, suitable for ion pair chromatography, LiChropur, ≥99.0%