Linked Life Data

1277150

Source:http://linkedlifedata.com/resource/pubmed/id/1277150

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
7 PT 1
pubmed:dateCreated
1976-9-1
pubmed:abstractText
The three-dimensional structures of two carcinogens, 7-chloromethyl-12-methylbenz[a]anthracene and 7-chloromethylbenz[ai1anthracene, have been determined by X-ray crystallographic techniques. Both compounds are carcinogenic and are believed to act by alkylating DNA. However, the first has a nonplanar ring system, whereas the second has a planar ring system. The nonplanarity of 7-chloromethyl-12-methylbenz[a]anthracene results from steric hindrance between a hydrogen atom of the 12-methyl group and a hydrogen atom on the [a] ring. This molecule cannot be made planar unless the 12-methyl group or the [a] ring is removed. It is concluded that the carcinogenic activity of these compounds does not correlate with planarity of the ring system. This implies that, if DNA is the critical target of attack by these carcinogens, complete intercalation of the aromatic ring system of the carcinogen between the bases of DNA is not a likely mechanism of carcinogenic action in this system of compounds. The results presented here and those of others are more consistent with a model for a common interaction of the carcinogens 7-chloromethyl-12-methylbenz[a]anthracene and 7-chloromethylbenz[a]anthracene with DNA, in which they alkylate the bases of DNA and then lie with their long axes approximately parallel to the helix axis, probably in the major groove.
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
Jul
pubmed:issn
0008-5472
pubmed:author
pubmed:issnType
Print
pubmed:volume
36
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
2428-35
pubmed:dateRevised
2008-11-21
pubmed:meshHeading
pubmed:year
1976
pubmed:articleTitle
Molecular structures of the chemical carcinogens 7-chloromethylbenz(a)anthracene and 7-chloromethyl-12-methylbenz(a)anthracene.
pubmed:publicationType
Journal Article, Research Support, U.S. Gov't, P.H.S., Research Support, U.S. Gov't, Non-P.H.S.