Design of a new DNA-polyintercalating drug, a bisacridinyl peptidic analogue of Triostin A

The synthesis of a new bifunctional compound in which two aminoacridine chromophores are linked by the bicyclic depsipeptidic backbone of des-N-tetramethylTriostin A is described. The molecule, bis-[(9-acridinyl)-D-seryl-L-alanyl-L-cysteinyl-L-valine] dilactone disulphide, structurally analogous to...

Full description

Saved in:
Bibliographic Details
Published inBiochemical journal Vol. 225; no. 3; pp. 829 - 832
Main Authors Helbecque, N, Bernier, J L, Hénichart, J P
Format Journal Article
LanguageEnglish
Published England 01.02.1985
Subjects
Aminacrine
Chemical Phenomena
Chemistry
DNA
Intercalating Agents - chemical synthesis
Models, Chemical
Oligopeptides - chemical synthesis
Spectrophotometry
Online AccessGet full text

Cover

More Information
Summary:The synthesis of a new bifunctional compound in which two aminoacridine chromophores are linked by the bicyclic depsipeptidic backbone of des-N-tetramethylTriostin A is described. The molecule, bis-[(9-acridinyl)-D-seryl-L-alanyl-L-cysteinyl-L-valine] dilactone disulphide, structurally analogous to the antibiotic anti-tumour drug Triostin A, is shown to possess a high affinity to DNA and to act as a bis-intercalator on the basis of spectroscopic, viscosimetric and thermal-denaturation studies. This model constitutes the first attempt of a synergic association between a peptidic moiety that mimics a naturally occurring drug and aminoacridine, the two parts themselves each exhibiting a high affinity for the DNA target.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0264-6021
1470-8728
DOI:10.1042/bj2250829