2. Academic Validation
  3. Synthesis of quinone imine and sulphur-containing compounds with antitumor and trypanocidal activities: redox and biological implications

Synthesis of quinone imine and sulphur-containing compounds with antitumor and trypanocidal activities: redox and biological implications

  • RSC Med Chem. 2020 Jul 13;11(10):1145-1160. doi: 10.1039/d0md00072h.
Renata G Almeida 1,  Wagner O Valença 1 2,  Luísa G Rosa 1,  Carlos A de Simone 3,  Solange L de Castro 4,  Juliana M C Barbosa 4,  Daniel P Pinheiro 5,  Carlos R K Paier 5,  Guilherme G C de Carvalho 5,  Claudia Pessoa 5,  Marilia O F Goulart 6,  Ammar Kharma 1 7,  Eufrânio N da Silva Júnior 1
Affiliations

Affiliations

  • 1 Institute of Exact Sciences , Department of Chemistry , Federal University of Minas Gerais , Belo Horizonte , 31270-901 , MG , Brazil . Email: eufranio@ufmg.br.
  • 2 Center for the Development of Chemical Technologies , State University of Mato Grosso do Sul , Naviraí , 79950-000 , MS , Brazil.
  • 3 Department of Physics and Informatics , Institute of Physics , University of São Paulo , São Carlos , 13560-160 , SP , Brazil.
  • 4 Oswaldo Cruz Institute , FIOCRUZ , Rio de Janeiro , 21045-900 , RJ , Brazil.
  • 5 Department of Physiology and Pharmacology , Federal University of Ceará , Fortaleza , CE 60430-270 , Brazil.
  • 6 Institute of Chemistry and Biotechnology , Federal University of Alagoas , CEP 57072-970 , Maceió , AL , Brazil.
  • 7 Division of Bioorganic Chemistry , School of Pharmacy , University of Saarland , D-66123 Saarbruecken , Germany.
PMID: 33479619 DOI: 10.1039/d0md00072h
Abstract

Ortho-Quinones represent a special class of redox active compounds associated with a spectrum of pronounced biological activities, including selective cytotoxicity and antimicrobial actions. The modification of the quinone ring by simple nitrogen and sulphur substitutions leads to several new classes of compounds with their own, distinct redox behaviour and equally distinct activities against Cancer cell lines and Trypanosoma cruzi. Some of the compounds investigated show activity against T. cruzi at concentrations of 24.3 and 65.6 μM with a selectivity index of around 1. These results demonstrate that simple chemical modifications on the ortho-quinone ring system, in particular, by heteroatoms such as nitrogen and sulphur, transform these simple redox molecules into powerful cytotoxic agents with considerable "potential", not only in synthesis and electrochemistry, but also, in a broader sense, in health sciences.

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