Document Detail


Global and local chemical reactivities of mutagen X and simple derivatives.
MedLine Citation:
PMID:  23463265     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
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.
Authors:
Elizabeth Rincon; Francisco Zuloaga; Eduardo Chamorro
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2013-3-6
Journal Detail:
Title:  Journal of molecular modeling     Volume:  -     ISSN:  0948-5023     ISO Abbreviation:  J Mol Model     Publication Date:  2013 Mar 
Date Detail:
Created Date:  2013-3-6     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9806569     Medline TA:  J Mol Model     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
Affiliation:
Instituto de Ciencias Quimicas, Facultad de Ciencias, Universidad Austral de Chile, Las encinas 220, Valdivia, Chile, elizabethrincon@uach.cl.
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