title: Psoralen and bergapten: in silico metabolism and toxicophoric analysis of drugs used to treat vitiligo.
abstract: OBJECTIVE
  To discuss the contribution of psoralen and bergapten metabolites on psoralens toxicity.
  
  
  METHODS
  Computational chemistry prediction of metabolic reactions and toxicophoric groups based on the expert systems Derek and Meteor.
  
  
  RESULTS
  a total of 15 metabolites were suggested for both psoralen and bergapten based on phase 1 and 2 biotransformations until the 3rd generation. Five toxicophoric substructures were shared among psoralen, bergapten and their corresponding metabolites; one toxicophoric marker (resorcinol) was only identified in bergapten and its biotransformation products.
  
  
  CONCLUSIONS
  Although the toxic effects of psoralens are well known and documented, there is little information concerning the role of their metabolites in this process. We believe this work add to the knowledge of which molecular substructures are relevant to the process of metabolism and toxicity induction, thus guiding the search and development of more effective and less toxic drugs to treat vitiligo.
authors.affiliation: Departamento de Ciências Farmacêuticas, Faculdade de Ciências Farmacêuticas de Ribeirão Preto, Universidade de São Paulo, Ribeirão Preto, CEP 14040-903, Brazil. vbs11@usp.br
authors.forename: Vinicius Barreto
authors.initials: VB
authors.lastname: da Silva
authors.forename: Daniel Fábio
authors.initials: DF
authors.lastname: Kawano
authors.forename: Ivone
authors.initials: I
authors.lastname: Carvalho
authors.forename: Edemilson Cardoso
authors.initials: EC
authors.lastname: da Conceição
authors.forename: Osvaldo
authors.initials: O
authors.lastname: de Freitas
authors.forename: Carlos Henrique Tomich de Paula
authors.initials: CH
authors.lastname: da Silva
mesh_terms: D000078223:5-Methoxypsoralen; D000818:Animals; D001711:Biotransformation; D019295:Computational Biology; D003198:Computer Simulation; D055808:Drug Discovery / Q000379:methods; D005103:Expert Systems; D005363:Ficusin / Q000378:metabolism* / Q000633:toxicity*; D006801:Humans; D008730:Methoxsalen / Q000031:analogs & derivatives* / Q000378:metabolism / Q000633:toxicity; D017319:Photosensitizing Agents / Q000378:metabolism* / Q000633:toxicity*; D014820:Vitiligo / Q000188:drug therapy
chemical_list: D017319:Photosensitizing Agents; D000078223:5-Methoxypsoralen; D005363:Ficusin; D008730:Methoxsalen