Global and local chemical reactivities of mutagen X and simple derivatives

Elizabeth Rincon, Francisco Zuloaga, Eduardo Chamorro

Resultado de la investigación: Article

6 Citas (Scopus)

Resumen

Registered by the World Health Organization (WHO), 3-chloro-4- (dichloromethyl)-5-hydroxy-2(5H)-furanone (MX) is one of the strongest bacterial mutagens ever tested, as highlighted by the Ames Salmonella typhimurium TA100 assay. We provide new insights concerning this mutagenic activity on the basis of global and local theoretically defined electrophilicity indices. Our results further support the idea that mutagenicity of MX and its analogues is related more closely to one-electron transfer processes from the electron-rich biological environment than to adduct formation processes. We also stress that, although the Z-open tautomers are intrinsically more electrophilic than furanone ring analogues, the observed mutagenic activity is significantly correlated only to the electrophilicity response of the ring forms. In that context, we also emphasize that it is electrophilicity at the C α in the α-β unsaturated carbonyl moiety that exhibits a strong correlation with the observed mutagenic activity. [Figure not available: see fulltext.]

Idioma originalEnglish
Páginas (desde-hasta)2573-2582
Número de páginas10
PublicaciónJournal of Molecular Modeling
Volumen19
N.º6
DOI
EstadoPublished - jun 2013

Huella dactilar

3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone
mutagens
Mutagens
Chemical reactivity
reactivity
Derivatives
Salmonella
Electrons
analogs
salmonella
Assays
rings
tautomers
Health
adducts
health
electron transfer
electrons

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Computer Science Applications
  • Computational Theory and Mathematics
  • Catalysis
  • Organic Chemistry
  • Inorganic Chemistry

Citar esto

Rincon, Elizabeth ; Zuloaga, Francisco ; Chamorro, Eduardo. / Global and local chemical reactivities of mutagen X and simple derivatives. En: Journal of Molecular Modeling. 2013 ; Vol. 19, N.º 6. pp. 2573-2582.
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Global and local chemical reactivities of mutagen X and simple derivatives. / Rincon, Elizabeth; Zuloaga, Francisco; Chamorro, Eduardo.

En: Journal of Molecular Modeling, Vol. 19, N.º 6, 06.2013, p. 2573-2582.

Resultado de la investigación: Article

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AB - Registered by the World Health Organization (WHO), 3-chloro-4- (dichloromethyl)-5-hydroxy-2(5H)-furanone (MX) is one of the strongest bacterial mutagens ever tested, as highlighted by the Ames Salmonella typhimurium TA100 assay. We provide new insights concerning this mutagenic activity on the basis of global and local theoretically defined electrophilicity indices. Our results further support the idea that mutagenicity of MX and its analogues is related more closely to one-electron transfer processes from the electron-rich biological environment than to adduct formation processes. We also stress that, although the Z-open tautomers are intrinsically more electrophilic than furanone ring analogues, the observed mutagenic activity is significantly correlated only to the electrophilicity response of the ring forms. In that context, we also emphasize that it is electrophilicity at the C α in the α-β unsaturated carbonyl moiety that exhibits a strong correlation with the observed mutagenic activity. [Figure not available: see fulltext.]

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