Document Detail


Diacridines: bifunctional intercalators. I. Chemistry, physical chemistry and growth inhibitory properties.
MedLine Citation:
PMID:  1247545     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
The synthesis, as well as the rationale for synthesis of diacridines, double intercalators, as potential inhibitors of nucleic acid synthesis is presented. The syntheses of (9-acridyl)-putrescine and -spermine, and bis(-9-acridyl)-putrescine, -spermidine, -spermine diamines and of bis(6-chloro-2-methoxy-9-acridyl)-putrescine and -spermine diamines, all substituted on the terminal NH2 groups are described. In addition, the homologous series of diacridines connected by the amino groups of the diamines NH2(CH2)nNH2 (where n = 2,3,4,6,8,10,12,14,16,18) to the C-9 of the diacridines has been synthesized. The chemical properties of these compounds as well as their molecular relationship to DNA are presented. The effect of the double intercalators on the Tm of DNA and of (A)n - (U)n, (dA)n - (dT)n, (G)n - (C)n and on (dG)n - (dC)n have been determined. The double acridine intercalators produce a much greater increase of the Tm of these nucleic acids than do the single acridine intercalators. They also profoundly affect the Tm of DNA in physiological salt concentrations; under these latter conditions the single intercalators have no effect. The relationship between the length of the chain connecting the two acridine rings and the inhibition of the growth of P-388 cells in vitro and vivo is presented. Their growth inhibitory properties appear, in general, to parallel their intercalative abilities.
Authors:
E S Canellakis; Y H Shaw; W E Hanners; R A Schwartz
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Publication Detail:
Type:  Journal Article; Research Support, U.S. Gov't, P.H.S.    
Journal Detail:
Title:  Biochimica et biophysica acta     Volume:  418     ISSN:  0006-3002     ISO Abbreviation:  Biochim. Biophys. Acta     Publication Date:  1976 Feb 
Date Detail:
Created Date:  1976-04-27     Completed Date:  1976-04-27     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  0217513     Medline TA:  Biochim Biophys Acta     Country:  NETHERLANDS    
Other Details:
Languages:  eng     Pagination:  277-89     Citation Subset:  IM    
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MeSH Terms
Descriptor/Qualifier:
Acridines* / chemical synthesis,  pharmacology
Binding Sites
Citrates
DNA / biosynthesis
Kinetics
Models, Molecular
Molecular Conformation
Nucleic Acid Conformation
Nucleic Acid Denaturation
Osmolar Concentration
Polynucleotides / biosynthesis
Spermine
Structure-Activity Relationship
Temperature
Chemical
Reg. No./Substance:
0/Acridines; 0/Citrates; 0/Polynucleotides; 71-44-3/Spermine; 9007-49-2/DNA

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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