Linked Life Data

7205885

Source:http://linkedlifedata.com/resource/pubmed/id/7205885

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
2
pubmed:dateCreated
1981-5-26
pubmed:abstractText
In an investigation of the structure-activity relationships in the 4'-(9-acridinylamino)methanesulfonanilide (AMSA) tumor inhibitory analogues, the DNA-binding properties of a series of simple 9-anilinoacridines were examined. Positional numbering as in the AMSA series has been employed. DNA binding was determined by drug competition with the fluorochrome ethidium for available sites. The decrease in fluorescence of a DNA-ethidium complex by the addition of drug is due to both drug displacement of bound ethidium and quenching of the fluorescence of bound ethidium by bound drug; measurement of both factors allows drug-DNA association constants (K) to be determined. DNA binding is augmented by 1' or 2' electron donor substituents, and significant correlation equations have been derived with Hammett's sigma p or sigma m constants. Group molar refractivity (MR) for 1'-substituents is an additional significant regression equation term for binding, while the values for 2' and 3' groups play no significant role. Most 3'-substituents decrease binding, presumably as a result of steric inhibition of entry of the acridine nucleus into intercalation sites. A 3'-NHSO2CH3 and 3'-NHCOCH3 substituent confer selectivity of binding to poly[d(G-C)] and poly[d(A-T)], respectively. It is suggested that a combination of H-bond formation and stereochemical features, coupled with steric hindrance, provides the selectivity observed. Binding data are consistent with a model in which the acridine nucleus occupies an intercalation site and the noncoplanar 9-anilino ring resides in the DNA minor groove.
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
Feb
pubmed:issn
0022-2623
pubmed:author
pubmed:issnType
Print
pubmed:volume
24
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
170-7
pubmed:dateRevised
2006-11-15
pubmed:meshHeading
pubmed:year
1981
pubmed:articleTitle
Potential antitumor agents. 34. Quantitative relationships between DNA binding and molecular structure for 9-anilinoacridines substituted in the anilino ring.
pubmed:publicationType
Journal Article, Research Support, Non-U.S. Gov't