Photosensitization of Escherichia coli and Saccharomyces cerevisiae by phenylheptatriyne from Bidens pilosa

Abstract

The photosensitizing action of 7-phenylhepta-2,4,6-triyne (PHT), a polyacetylenic compound isolated from Bidens pilosa L. (Asteraceae), has been studied using Escherichia coli and Saccharomyces cerevisiae as the test organisms. The survival curves for E. coli treated with PHT and ultraviolet (UV) radiation were obtained and have been interpreted quantitatively on the basis of a target theory model. The number of "targets" in the cell that must be destroyed before cell death occurs was estimated at six, whereas the dose, D₀, that reduced the surviving fraction of the population to 1/e of its value was estimated to be 280 J/m².Survival was enhanced in aerobic conditions as compared with anaerobic conditions, which is strong evidence that PHT does not behave as a photodynamic sensitizer in vivo. This view was confirmed by work with azide (a quencher of singlet oxygen), D₂O (which increases the lifetime of singlet oxygen), and superoxide dismutase (which scavenges superoxide radicals). None of these treatments modified the survival curves significantly, indicating that activated species of O₂ are probably not involved in photosensitizations with PHT in vivo.Cell respiration was found to be rapidly inhibited by mild treatments of PHT and UV radiation, suggesting that nuclear metabolism is not the primary target of photosensitization as is the case with another group of photosensitizers, the furanocoumarins. The available evidence indicates that PHT is a representative of a new class of phototoxic compounds. A mechanism of action involving production of free radicals is proposed.