title: Reduction of aflatoxin B1 to aflatoxicol: a comprehensive DFT study provides clues to its toxicity.
abstract: BACKGROUND
  Aflatoxicol (AFL) is one of most the important metabolites of aflatoxin B1 (AFB1). AFL can be formed through enzymatic or synthetic reduction of AFB1. Various experimental and theoretical studies have been focused on the AFB1 due to its high toxicity and carcinogenicity.
  
  
  RESULTS
  The selective reduction of AFB1 carbonyls, molecular structure of AFL and its effect on toxicity has been studied here by the density functional theory (DFT) method. Although the toxicity of AFL is 18 times lower than that of AFB1, it has been concluded that both molecular structures have similar potency to form an exo-epoxide (AFEP) analogue which can bind to DNA.
  
  
  CONCLUSIONS
  Calculations revealed that only one of the three possible tautomers of AFL is stable, both in the gas phase and water. The electronic properties of aflatoxicol are calculated as similar to aflatoxin B1 and this may be an explanation of similar carcinogenicity and toxicity of these compounds, which has been proved by experimental results.
authors.affiliation: Department of Chemistry, Faculty of Science and Literature, Balikesir University, Balikesir, Turkey.
authors.forename: Sedat
authors.initials: S
authors.lastname: Karabulut
authors.forename: Guvanchmyrat
authors.initials: G
authors.lastname: Paytakov
authors.forename: Jerzy
authors.initials: J
authors.lastname: Leszczynski
mesh_terms: D016604:Aflatoxin B1 / Q000737:chemistry* / Q000378:metabolism / Q000633:toxicity*; D000348:Aflatoxins / Q000737:chemistry* / Q000378:metabolism; D002273:Carcinogens; D004247:DNA / Q000378:metabolism; D004249:DNA Damage; D004355:Drug Stability; D004852:Epoxy Compounds / Q000737:chemistry / Q000378:metabolism; D006801:Humans; D008958:Models, Molecular; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D000348:Aflatoxins; D002273:Carcinogens; D004852:Epoxy Compounds; C012170:aflatoxicol; D004247:DNA; D016604:Aflatoxin B1
keywords: DFT; aflatoxicol; aflatoxin B1; tautomer; toxicity