Intramolecular Charge Transfer in the Azathioprine Prodrug Quenches Intersystem Crossing to the Reactive Triplet State in 6‐Mercaptopurine †
| Autor: | Sean J. Hoehn, Glesmarie Ortiz-Zayas, Luis A. Ortiz-Rodríguez, Steffen Jockusch, Carlos E. Crespo-Hernández, Marvin Pollum |
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| Rok vydání: | 2021 |
| Předmět: |
Absorption (pharmacology)
Singlet Oxygen Thiopurine methyltransferase biology Mercaptopurine Ultraviolet Rays Chemistry Singlet oxygen Azathioprine General Medicine Prodrug Photochemistry Biochemistry chemistry.chemical_compound Intersystem crossing medicine biology.protein Humans Prodrugs sense organs Physical and Theoretical Chemistry Triplet state medicine.drug |
| Zdroj: | Photochemistry and Photobiology. 98:617-632 |
| ISSN: | 1751-1097 0031-8655 |
| DOI: | 10.1111/php.13513 |
| Popis: | The thiopurine prodrugs 6-mercaptopurine and azathioprine are among the world's essential medications for acute lymphoblastic leukemia, immunosuppression and several autoimmune conditions. Thiopurine prodrugs are efficient UVA absorbers and singlet oxygen generators and the long-term treatment with these prodrugs correlates with a high incidence of sunlight-induced skin cancer in patients. In this contribution, we show that the electronic relaxation mechanisms and photochemical properties of azathioprine are remarkably different from those of 6-mercaptopurine upon absorption of UVA radiation. UVA excitation of 6-mercaptopurine results in nearly 100% triplet yield and up to 30% singlet oxygen generation, whereas excitation of azathioprine with UVA leads to triplet yields of 15-3% depending on pH of the aqueous solution and |
| Databáze: | OpenAIRE |
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