Psoralen and Bergapten: In Silico Metabolism and Toxicophoric Analysis of Drugs Used to Treat Vitiligo
PURPOSE: 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 psoral...
| Main Authors: | , , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
Frontiers Media S.A.
2009-12-01
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| Series: | Journal of Pharmacy & Pharmaceutical Sciences |
| Online Access: | https://journals.library.ualberta.ca/jpps/index.php/JPPS/article/view/6499 |
| _version_ | 1797709191069040640 |
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| author | Vinicius Barreto da Silva Daniel Fábio Kawano Ivone Carvalho Edemilson Cardoso Conceição Osvaldo Freitas Carlos Henrique Tomich de Paula Silva |
| author_facet | Vinicius Barreto da Silva Daniel Fábio Kawano Ivone Carvalho Edemilson Cardoso Conceição Osvaldo Freitas Carlos Henrique Tomich de Paula Silva |
| author_sort | Vinicius Barreto da Silva |
| collection | DOAJ |
| description | PURPOSE: 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. CONCLUSION: 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. |
| first_indexed | 2024-03-12T06:32:46Z |
| format | Article |
| id | doaj.art-30fdc7b74e944b55af52691b40275d89 |
| institution | Directory Open Access Journal |
| issn | 1482-1826 |
| language | English |
| last_indexed | 2024-03-12T06:32:46Z |
| publishDate | 2009-12-01 |
| publisher | Frontiers Media S.A. |
| record_format | Article |
| series | Journal of Pharmacy & Pharmaceutical Sciences |
| spelling | doaj.art-30fdc7b74e944b55af52691b40275d892023-09-03T01:29:49ZengFrontiers Media S.A.Journal of Pharmacy & Pharmaceutical Sciences1482-18262009-12-0112310.18433/J3W01DPsoralen and Bergapten: In Silico Metabolism and Toxicophoric Analysis of Drugs Used to Treat VitiligoVinicius Barreto da Silva0Daniel Fábio Kawano1Ivone Carvalho2Edemilson Cardoso Conceição3Osvaldo Freitas4Carlos Henrique Tomich de Paula Silva5Departamento de Ciências Farmacêuticas, Faculdade de Ciências Farmacêuticas de Ribeirão Preto, Universidade de São PauloDepartamento de Ciências Farmacêuticas, Faculdade de Ciências Farmacêuticas de Ribeirão Preto, Universidade de São PauloDepartamento de Ciências Farmacêuticas, Faculdade de Ciências Farmacêuticas de Ribeirão Preto, Universidade de São PauloDepartamento de Tecnologia Farmacêutica, Faculdade de Farmácia, Universidade Federal de GoiásDepartamento de Ciências Farmacêuticas, Faculdade de Ciências Farmacêuticas de Ribeirão Preto, Universidade de São PauloDepartamento de Ciências Farmacêuticas, Faculdade de Ciências Farmacêuticas de Ribeirão Preto, Universidade de São PauloPURPOSE: 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. CONCLUSION: 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.https://journals.library.ualberta.ca/jpps/index.php/JPPS/article/view/6499 |
| spellingShingle | Vinicius Barreto da Silva Daniel Fábio Kawano Ivone Carvalho Edemilson Cardoso Conceição Osvaldo Freitas Carlos Henrique Tomich de Paula Silva Psoralen and Bergapten: In Silico Metabolism and Toxicophoric Analysis of Drugs Used to Treat Vitiligo Journal of Pharmacy & Pharmaceutical Sciences |
| title | Psoralen and Bergapten: In Silico Metabolism and Toxicophoric Analysis of Drugs Used to Treat Vitiligo |
| title_full | Psoralen and Bergapten: In Silico Metabolism and Toxicophoric Analysis of Drugs Used to Treat Vitiligo |
| title_fullStr | Psoralen and Bergapten: In Silico Metabolism and Toxicophoric Analysis of Drugs Used to Treat Vitiligo |
| title_full_unstemmed | Psoralen and Bergapten: In Silico Metabolism and Toxicophoric Analysis of Drugs Used to Treat Vitiligo |
| title_short | Psoralen and Bergapten: In Silico Metabolism and Toxicophoric Analysis of Drugs Used to Treat Vitiligo |
| title_sort | psoralen and bergapten in silico metabolism and toxicophoric analysis of drugs used to treat vitiligo |
| url | https://journals.library.ualberta.ca/jpps/index.php/JPPS/article/view/6499 |
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