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| Predicate | Object |
|---|---|
| rdf:type | |
| lifeskim:mentions | |
| pubmed:issue |
2-3
|
| pubmed:dateCreated |
1994-3-8
|
| pubmed:abstractText |
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.
|
| pubmed:language |
eng
|
| pubmed:journal | |
| pubmed:citationSubset |
IM
|
| pubmed:chemical |
http://linkedlifedata.com/resource/pubmed/chemical/Alkynes,
http://linkedlifedata.com/resource/pubmed/chemical/DNA, Viral,
http://linkedlifedata.com/resource/pubmed/chemical/Diynes,
http://linkedlifedata.com/resource/pubmed/chemical/Oxygen,
http://linkedlifedata.com/resource/pubmed/chemical/Photosensitizing Agents,
http://linkedlifedata.com/resource/pubmed/chemical/Singlet Oxygen,
http://linkedlifedata.com/resource/pubmed/chemical/Superoxides
|
| pubmed:status |
MEDLINE
|
| pubmed:month |
Dec
|
| pubmed:issn |
1011-1344
|
| pubmed:author | |
| pubmed:issnType |
Print
|
| pubmed:volume |
21
|
| pubmed:owner |
NLM
|
| pubmed:authorsComplete |
Y
|
| pubmed:pagination |
135-42
|
| pubmed:dateRevised |
2007-7-23
|
| pubmed:meshHeading |
pubmed-meshheading:8301409-3T3 Cells,
pubmed-meshheading:8301409-Alkynes,
pubmed-meshheading:8301409-Animals,
pubmed-meshheading:8301409-Bacteriophage M13,
pubmed-meshheading:8301409-DNA, Viral,
pubmed-meshheading:8301409-DNA Damage,
pubmed-meshheading:8301409-Daphnia,
pubmed-meshheading:8301409-Diynes,
pubmed-meshheading:8301409-Enterococcus faecalis,
pubmed-meshheading:8301409-Escherichia coli,
pubmed-meshheading:8301409-Fishes,
pubmed-meshheading:8301409-Isomerism,
pubmed-meshheading:8301409-Mice,
pubmed-meshheading:8301409-Oxygen,
pubmed-meshheading:8301409-Photochemistry,
pubmed-meshheading:8301409-Photosensitizing Agents,
pubmed-meshheading:8301409-Plasmids,
pubmed-meshheading:8301409-Singlet Oxygen,
pubmed-meshheading:8301409-Spectrophotometry,
pubmed-meshheading:8301409-Superoxides
|
| pubmed:year |
1993
|
| pubmed:articleTitle |
DNA cleavage, antiviral and cytotoxic reactions photosensitized by simple enediyne compounds.
|
| pubmed:affiliation |
Department of Chemistry, University of Illinois at Chicago 60607-7061.
|
| pubmed:publicationType |
Journal Article,
Research Support, Non-U.S. Gov't
|