DNA Cleavage, antiviral and cytotoxic reactions photosensitized by simple enediyne compounds
| Autor: | Irenea V. Batac, Ka Y. Lau, Jacques Kagan, James B. Hudson, R. W. Tuveson, Xiangdong Wang, Xinsheng Chen |
|---|---|
| Rok vydání: | 1993 |
| Předmět: |
Sindbis virus
Photochemistry Stereochemistry Biophysics Biology medicine.disease_cause Diynes Mice chemistry.chemical_compound Isomerism Superoxides Enterococcus faecalis Escherichia coli medicine Enediyne Animals Moiety Radiology Nuclear Medicine and imaging Photosensitizing Agents Radiation Singlet Oxygen Radiological and Ultrasound Technology Superoxide Singlet oxygen Fishes 3T3 Cells biology.organism_classification Oxygen Daphnia chemistry Spectrophotometry Alkynes Bergman cyclization DNA Viral DNA Bacteriophage M13 DNA Damage Plasmids |
| Zdroj: | Journal of Photochemistry and Photobiology B: Biology. 21:135-142 |
| ISSN: | 1011-1344 |
| DOI: | 10.1016/1011-1344(93)80175-9 |
| Popis: | Very potent antibiotic antitumor natural products contain a enediyne moiety which, upon thermal activation, is capable of abstracting hydrogens from DNA. 1,6-Diphenyl-3-hexene-1,5-diyne was selected as a candidate for inducing DNA strand breaks photochemically. Easily interconverted with light, both geometric isomers 1 and 2 were expected to be phototoxic. As anticipated, they photosensitized the production of strand breaks in double-stranded supercoiled pBR322, and in single-stranded M13 DNA. The DNA cleavage reactions were favored by the presence of oxygen and were inhibited by ethanol. Preliminary experiments with the (Z)-isomer indicated moderate light-dependent antiviral activity against human immunodeficiency virus (HIV), Sindbis virus, and mouse cytomegalovirus. The enediynes were cytotoxic to Escherichia coli, a gram-negative organism, to Streptococcus faecalis, a gram-positive organism, to Daphnia magna and to fish (Pimephales promelas), but only in the presence of light. The production of o-terphenyl, the expected product of Bergman cyclization of 1, could not be confirmed. However, both 1 and 2 photosensitized the formation of singlet oxygen and of superoxide anion radical, and photodynamic reactions could have been responsible for some of the phototoxic reactions observed. |
| Databáze: | OpenAIRE |
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