Structure-activity studies of photoactivated antiviral and cytotoxic tricyclic thiophenes
| Autor: | Robin J. Marles, C. Soucy-Breau, James B. Hudson, R. L. Compadre, E. A. Graham, John T. Arnason, Peter Morand, G.H.N. Towers, Cesar M. Compadre |
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| Rok vydání: | 1992 |
| Předmět: |
Sindbis virus
Stereochemistry Cell Survival Ultraviolet Rays Carboxylic acid Cytomegalovirus Mast-Cell Sarcoma Antineoplastic Agents Thiophenes Biochemistry Antiviral Agents chemistry.chemical_compound Mice Structure-Activity Relationship Thiophene Tumor Cells Cultured Cytotoxic T cell Animals Physical and Theoretical Chemistry Cytotoxicity chemistry.chemical_classification biology Chemistry General Medicine 3T3 Cells biology.organism_classification In vitro Sindbis Virus Phototoxicity Tricyclic |
| Zdroj: | Photochemistry and photobiology. 56(4) |
| ISSN: | 0031-8655 |
| Popis: | The photoactivated antiviral and cytotoxic activities of the naturally occurring thiophene, alpha-terthienyl (1), and 15 synthetic analogues were evaluated against murine cytomegalovirus and Sindbis virus, and murine mastocytoma cells. After irradiation with near UV light alpha-terthienyl and most of its analogues had significant toxicity, with minimum inhibitory concentrations in the range of 0.02-40 micromolar. In the absence of near UV irradiation, only one analogue had antiviral activity and five were cytotoxic. The most active analogues were those containing carboxylic acid, hydroxyl, or cyano substituents. Quantitative structure-activity relationship analysis of thiophene phototoxicity suggested that the rate of singlet oxygen production is the primary determinant of antiviral and cytotoxic activities. For phototoxicity against murine cytomegalovirus, a significant role for hydrophobicity was also demonstrated. Tricyclic thiophenes show significant potential for photochemotherapy of viral infections and cancer, and further evaluation in animal models is recommended. |
| Databáze: | OpenAIRE |
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