In Vitro Inhibition of Helicobacter pylori Growth by Redox Cycling Phenylaminojuglones

Infection by Helicobacter pylori increases 10 times the risk of developing gastric cancer. Juglone, a natural occurring 1,4-naphthoquinone, prevents H. pylori growth by interfering with some of its critical metabolic pathways. Here, we report the design, synthesis, and in vitro evaluation of a serie...

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Bibliographic Details
Published in:Oxidative medicine and cellular longevity 2018-01, Vol.2018 (2018), p.1-8
Main Authors: Buc Calderon, Pedro, Rios, David, Guerrero, Angélica, Salas, Felipe, Toledo, Héctor, Benites, Julio, Valderrama, Jaime
Format: Article
Language:English
Subjects:
Anti-Bacterial Agents - pharmacology
Anti-Bacterial Agents - therapeutic use
Antibiotics
Antimicrobial agents
Biological activity
Biological Products - pharmacology
Biological Products - therapeutic use
Chromatography
Development and progression
Gastric cancer
Health aspects
Helicobacter Infections - drug therapy
Helicobacter pylori
Helicobacter pylori - pathogenicity
Humans
Infections
Metronidazole
Naphthoquinones - pharmacology
Naphthoquinones - therapeutic use
NMR
Nuclear magnetic resonance
Organic chemistry
Oxidation-Reduction
Patient compliance
Phytochemicals
Stomach cancer
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Summary:Infection by Helicobacter pylori increases 10 times the risk of developing gastric cancer. Juglone, a natural occurring 1,4-naphthoquinone, prevents H. pylori growth by interfering with some of its critical metabolic pathways. Here, we report the design, synthesis, and in vitro evaluation of a series of juglone derivatives, namely, 2/3-phenylaminojuglones, as potential H. pylori growth inhibitors. Results show that 5 out of 12 phenylaminojuglones (at 1.5 μg/mL) were 1.5–2.2-fold more active than juglone. Interestingly, most of the phenylaminojuglones (10 out of 12) were 1.1–2.8 fold more active than metronidazole, a known H. pylori growth inhibitor. The most active compound, namely, 2-((3,4,5-trimethoxyphenyl)amino)-5-hydroxynaphthalene-1,4-dione 7, showed significant higher halo of growth inhibitions (HGI = 32.25 mm) to that of juglone and metronidazole (HGI = 14.50 and 11.67 mm). Structural activity relationships of the series suggest that the nature and location of the nitrogen substituents in the juglone scaffold, likely due in part to their redox potential, may influence the antibacterial activity of the series.
ISSN:1942-0900
1942-0994
DOI:10.1155/2018/1618051