<i>In Vitro</i> Inhibition of <i>Helicobacter pylori</i> Growth by Redox Cycling Phenylaminojuglones

Benites, Julio; Toledo, Héctor; Salas, Felipe; Guerrero, Angélica Hernández; Ríos, David; Valderrama, Jaime A.; Calderón, Pedro Buc

doi:10.1155/2018/1618051

Cited by 8 publications

(9 citation statements)

References 55 publications

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“…The NADPHcytochrome P450 reductase enzyme catalyzes the reduction of an electron from Q7 to the semiquinone (•Q7) which becomes very reactive. This semiquinone •Q7 is reoxidized to the quinone in the presence of molecular oxygen, while oxygen is reduced to superoxide radical ( • O2 -) (Benites et al, 2018). We confirmed that Q7 causes oxidative stress in proteins.…”

Section: Q7 Induces Oxidative Stress and Role Of Ascorbatesupporting

confidence: 61%

Ascorbic supplementation attenuates juglone induced metabolic derangement

Ayavire¹,

Fonseca²,

Salas³

et al. 2021

BLACPMA

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Juglone derivatives like 2-(4-hydroxyphenyl) amino-1,4-naphthoquinone (Q7) are used as antitumor agents, and act through reactive oxygen species (ROS) generation. Such may lead to abnormal lipid metabolism and ROS dysregulation. The objective of this study was to evaluate the effect of ascorbate on the metabolism of lipids and carbohydrates following Q7-induced oxidative stress. Male Wistar rats were administered Q7 (10 mg/Kg) and/or ascorbate (500 mg/Kg) orally for 20 days. Rats treated with Q7 showed an increase in serum triglycerides, VLDL cholesterol and lipid peroxidation levels. When Q7 treatment was followed up by ascorbate (500 mg/Kg) administration, we observed a reduction in serum triglycerides, VLDL cholesterol and lipid peroxidation. The oral administration of ascorbate reduced the Q7-induced increases in lipids, and postprandial glycemia. This could be associated with the redox activity of ascorbate that reduced the oxidative stress induced by Q7. We thus conclude that ascorbate modulates the Q7-induced increase of lipid and carbohydrate metabolism.

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Section: Q7 Induces Oxidative Stress and Role Of Ascorbatesupporting

confidence: 61%

Ascorbic supplementation attenuates juglone induced metabolic derangement

Ayavire¹,

Fonseca²,

Salas³

et al. 2021

BLACPMA

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“…Both AroQ and AroE (retrieved from metabolic pathway proteins and essential proteins analysis approaches) are involved in the chorismate synthesis, which is the precursor of folic acid and aromatic amino acids (phenylalanine, tyrosine, and tryptophan) that take part in protein and nucleic acid biosynthesis. Inhibition of folate biosynthesis is known to exert an anti-helicobacter activity [ 41 , 42 ]. DapB is involved in lysine biosynthesis via diaminopimelate, which are compounds used by bacteria to link peptidoglycan covalently to their cell wall.…”

Section: Discussionmentioning

confidence: 99%

Identification of Potential Drug Targets in Helicobacter pylori Using In Silico Subtractive Proteomics Approaches and Their Possible Inhibition through Drug Repurposing

et al. 2020

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The class 1 carcinogen, Helicobacter pylori, is one of the World Health Organization’s high priority pathogens for antimicrobial development. We used three subtractive proteomics approaches using protein pools retrieved from: chokepoint reactions in the BIOCYC database, the Kyoto Encyclopedia of Genes and Genomes, and the database of essential genes (DEG), to find putative drug targets and their inhibition by drug repurposing. The subtractive channels included non-homology to human proteome, essentiality analysis, sub-cellular localization prediction, conservation, lack of similarity to gut flora, druggability, and broad-spectrum activity. The minimum inhibitory concentration (MIC) of three selected ligands was determined to confirm anti-helicobacter activity. Seventeen protein targets were retrieved. They are involved in motility, cell wall biosynthesis, processing of environmental and genetic information, and synthesis and metabolism of secondary metabolites, amino acids, vitamins, and cofactors. The DEG protein pool approach was superior, as it retrieved all drug targets identified by the other two approaches. Binding ligands (n = 42) were mostly small non-antibiotic compounds. Citric, dipicolinic, and pyrophosphoric acid inhibited H. pylori at an MIC of 1.5–2.5 mg/mL. In conclusion, we identified potential drug targets in H. pylori, and repurposed their binding ligands as possible anti-helicobacter agents, saving time and effort required for the development of new antimicrobial compounds.

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“…Melting points (mp) were determined on a Stuart Scientific SMP3 (Staffordshire, UK) apparatus and are uncorrected. The record of IR, 1 H- and 13 C-NMR spectra, and chromatography procedures were done according to methods reported by Benites et al [ 27 ]. Proton nuclear magnetic resonance ( 1 H NMR) spectra were measured at 300 MHz in a Bruker Ultrashield-300 spectrometer.…”

Section: Methodsmentioning

confidence: 99%

New 2-Acetyl-3-aminophenyl-1,4-naphthoquinones: Synthesis andIn VitroAntiproliferative Activities on Breast and Prostate Human Cancer Cells

Ríos

Valderrama

Cautin

et al. 2020

Oxidative Medicine and Cellular Longevity

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The reaction of 2-acyl-1,4-naphthoquinones with N,N-dimethylaniline and 2,5-dimethoxyaniline, promoted by catalytic amounts of CeCl3·7H2O under “open-flask” conditions, produced a variety of 2-acyl-3-aminophenyl-1,4-naphthoquinones structurally related to the cytotoxic 2-acetyl-3-phenyl-1,4-naphthoquinone, an inhibitor of the heat shock chaperone protein Hsp90. The members of the 2-acyl-3-aminophenyl-1,4-naphthoquinone series were isolated in good yields (63-98%). The cyclic voltammograms of the 2-acyl-3-aminophenyl-1,4-naphthoquinone exhibit two one-electron reduction waves to the corresponding radical-anion and dianion and two quasireversible oxidation peaks. The first and second half-wave potential values (E1/2) of the members of the series are sensitive to the push-pull electronic effects of the substituents in the naphthoquinone scaffold. Furthermore, the in vitro antiproliferative properties of these new quinones were evaluated on two human cancer cells DU-145 (prostate) and MCF-7 (mammary) and a nontumorigenic HEK-293 (kidney) cell line, using the MTT colorimetric method. Two members, within the series, exhibited interesting cytotoxic activities on human prostate and mammary cancer cells.

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In Vitro Inhibition of Helicobacter pylori Growth by Redox Cycling Phenylaminojuglones

Cited by 8 publications

References 55 publications

Ascorbic supplementation attenuates juglone induced metabolic derangement

Ascorbic supplementation attenuates juglone induced metabolic derangement

Identification of Potential Drug Targets in Helicobacter pylori Using In Silico Subtractive Proteomics Approaches and Their Possible Inhibition through Drug Repurposing

New 2-Acetyl-3-aminophenyl-1,4-naphthoquinones: Synthesis andIn VitroAntiproliferative Activities on Breast and Prostate Human Cancer Cells

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