New analogues of amonafide and elinafide, containing aromatic heterocycles: synthesis, antitumor activity, molecular modeling, and DNA binding properties.
J Med Chem
; 47(6): 1391-9, 2004 Mar 11.
Article
in En
| MEDLINE
| ID: mdl-14998328
ABSTRACT
Amonafide- and elinafide-related mono and bisintercalators, modified by the introduction of a pi-excedent furan or thiophene ring fused to the naphthalimide moiety, have been synthesized. These compounds have shown an interesting antitumor profile. The best compound, 9, was 2.5-fold more potent than elinafide against human colon carcinoma cells (HT-29). Molecular dynamic simulations and physicochemical experiments have demonstrated that these compounds are capable of forming stable DNA complexes. These results, together with those previously reported by us for imidazo- and pyrazinonaphthalimide analogues, have prompted us to propose that the DNA binding process does not depend on the electronic nature of the fused heterocycle.
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Collection:
01-internacional
Database:
MEDLINE
Main subject:
DNA
/
Amides
/
Imides
/
Intercalating Agents
/
Isoquinolines
Limits:
Animals
/
Humans
Language:
En
Journal:
J Med Chem
Journal subject:
QUIMICA
Year:
2004
Document type:
Article
Affiliation country:
Spain