Sulfaquinoxaline inhibition of vitamin K epoxide and quinone reductase

Preusch, Peter C.; Hazelett, Susan; Lemasters, Kristine K.

doi:10.1016/0003-9861(89)90082-9

Cited by 14 publications

(3 citation statements)

References 31 publications

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“…Decursin induced cell-cycle arrest in prostate cancer derived cells , and coumarin itself produced tumor regression in clinical trials of metastatic prostate cancer . Sulfaquinoxaline, another compound identified in this study, is an antimicrobial that also has activity against vitamin K 1 epoxide . The connection between vitamin K 1 epoxide and AR activity is not immediately obvious but warrants further investigation, as the structure−activity relationship of these compounds suggest a novel mechanism to inhibit AR activity.…”

Section: Resultsmentioning

confidence: 84%

A Cellular Conformation-Based Screen for Androgen Receptor Inhibitors

Jones

Diamond

2008

ACS Chem. Biol.

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The androgen receptor (AR), a member of the steroid nuclear receptor family of transcription factors, regulates a wide range of physiological processes. Androgen signaling is also associated with numerous human diseases, including prostate cancer. All current antiandrogen therapies reduce ligand access to AR, whether by competitive antagonism or inhibition of androgen production, but are limited by acquired resistance and serious side-effects. Thus, novel antiandrogens that target events subsequent to ligand binding could have important therapeutic value. We developed a high throughput assay that exploits fluorescence resonance energy transfer (FRET) to measure ligand-induced conformation change in AR. We directly compared this assay to a transcription-based assay in a screen of FDA-approved compounds and natural products. The FRET-based screen identified compounds with previously unrecognized antiandrogen activities, with equivalent sensitivity and superior specificity compared to a reporter-based screen. This approach can thus improve the identification of small molecule AR inhibitors.

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Section: Resultsmentioning

confidence: 84%

A Cellular Conformation-Based Screen for Androgen Receptor Inhibitors

Jones

Diamond

2008

ACS Chem. Biol.

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“…Sulfaquinoxaline (SQX), a sulfonamide class compound, is one of the oldest synthetic antimicrobials still used, mainly in veterinary medicine, due to its low cost and broadspectrum activity against Gram-negative and Gram-positive bacteria and protozoa, in order to prevent coccidiosis and bacterial infections [8,9]. It is also used in rodenticides because it acts as an anticoagulant, due to the inhibition of K vitamin synthesis [10]. This compound shows low adsorption on soil (log K ow = 1.7) and as a result, it has been detected in environmental waters at concentrations ranging from 29.5 to 40.8 ng L −1 [4].…”

Section: Introductionmentioning

confidence: 99%

Sulfaquinoxaline Oxidation and Toxicity Reduction by Photo-Fenton Process

Urbano

Maniero

Guimarães

et al. 2021

IJERPH

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Sulfaquinoxaline (SQX) has been detected in environmental water samples, where its side effects are still unknown. To the best of our knowledge, its oxidation by Fenton and photo-Fenton processes has not been previously reported. In this study, SQX oxidation, mineralization, and toxicity (Escherichia coli and Staphylococcus aureus bacteria) were evaluated at two different setups: laboratory bench (2 L) and pilot plant (15 L). The experimental design was used to assess the influence of the presence or absence of radiation source, as well as different H2O2 concentrations (94.1 to 261.9 mg L−1). The experimental conditions of both setups were: SQX = 25 mg L−1, Fe(II) = 10 mg L−1, pH 2.8 ± 0.1. Fenton and photo-Fenton were suitable for SQX oxidation and experiments resulted in higher SQX mineralization than reported in the literature. For both setups, the best process was the photo-Fenton (178.0 mg L−1 H2O2), for which over 90% of SQX was removed, over 50% mineralization, and bacterial growth inhibition less than 13%. In both set-ups, the presence or absence of radiation was equally important for sulfaquinoxaline oxidation; however, the degradation rates at the pilot plant were between two to four times higher than the obtained at the laboratory bench.

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“…Several compounds, not being 4-hydroxycoumarins, have vitamin K-antagonistic properties and have been shown to inhibit vitamin KO-reductase. These compounds include salicylate (124)(125)(126), lapachol (127) and sulphaquinoxaline (128).…”

Section: Coumarin Derivativesmentioning

confidence: 99%

Vitamin K-dependent carboxylase : growth to maturity

Soute

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Sulfaquinoxaline inhibition of vitamin K epoxide and quinone reductase

Cited by 14 publications

References 31 publications

A Cellular Conformation-Based Screen for Androgen Receptor Inhibitors

A Cellular Conformation-Based Screen for Androgen Receptor Inhibitors

Sulfaquinoxaline Oxidation and Toxicity Reduction by Photo-Fenton Process

Vitamin K-dependent carboxylase : growth to maturity

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