Trypanosoma cruzi: Activities of lapachol and α- and β-lapachone derivatives against epimastigote and trypomastigote forms

Derivatives obtained by chemical modifications of lapachol, α- and β-lapachones, have been synthesized and their trypanocidal activity evaluated in vitro in Trypanosoma cruzi epimastigote and trypomastigote forms. Derivatives of natural quinones with biological activities, such as lapachol, α- and β...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry 2008-01, Vol.16 (2), p.668-674
Main Authors: Salas, Cristian, Tapia, Ricardo A., Ciudad, Karina, Armstrong, Verónica, Orellana, Myriam, Kemmerling, Ulrike, Ferreira, Jorge, Maya, Juan Diego, Morello, Antonio
Format: Article
Language:English
Subjects:
Animals
Anti-trypanosomal activity
Antibiotics. Antiinfectious agents. Antiparasitic agents
Antiparasitic agents
Biological and medical sciences
Lapachol derivatives
Medical sciences
Molecular Structure
Naphthoquinones - chemical synthesis
Naphthoquinones - chemistry
Naphthoquinones - pharmacology
Oxidation-Reduction
Oxidative stress
Pharmacology. Drug treatments
Redox cycling
Stereoisomerism
Trypanocidal Agents - chemical synthesis
Trypanocidal Agents - chemistry
Trypanocidal Agents - pharmacology
Trypanosoma cruzi - drug effects
α- and β-Lapachone derivatives
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Summary:Derivatives obtained by chemical modifications of lapachol, α- and β-lapachones, have been synthesized and their trypanocidal activity evaluated in vitro in Trypanosoma cruzi epimastigote and trypomastigote forms. Derivatives of natural quinones with biological activities, such as lapachol, α- and β-lapachones, have been synthesized and their trypanocidal activity evaluated in vitro in Trypanosoma cruzi cells. All tested compounds inhibited epimastigote growth and trypomastigote viability. Several compounds showed similar or higher activity as compared with current trypanocidal drugs, nifurtimox and benznidazole. The results presented here show that the anti- T. cruzi activity of the α-lapachone derivatives can be increased by the replacement of the benzene ring by a pyridine moiety. Free radical production and consequently oxidative stress through redox cycling or production of electrophilic metabolites are the potential biological mechanism of action for these synthetic quinones.
ISSN:0968-0896
1464-3391
DOI:10.1016/j.bmc.2007.10.038