Synthesis and DNA binding properties of saturated distamycin analogues

• Published in: Bioorganic & medicinal chemistry letters Vol. 12; no. 18; pp. 2647 - 2650
• Main Authors: Woods, Craig R., Faucher, Nicolas, Eschgfaller, Bernd, Bair, Kenneth W., Boger, Dale L.
• Format: Journal Article
• Language: English
• Published: Oxford Elsevier Ltd 16-09-2002; Elsevier
• Subjects: Biological and medical sciences; Distamycins - chemical synthesis; Distamycins - chemistry; Distamycins - metabolism; DNA - metabolism; Medical sciences; Miscellaneous; Pharmacology. Drug treatments; Biological fixation; Hairpin loop; Nylon; Oligopeptides; Structure activity relation; DNA; Pyrrole derivative polymer; Molecular interaction; Furan derivative polymer; Oligomer; Chemical synthesis; In vitro
• ISSN: 0960-894X; 1464-3405
• DOI: 10.1016/S0960-894X(02)00467-5

A series of saturated heterocyclic analogues of distamycin were prepared and examined. A fluorescent intercalator displacement (FID) assay conducted on p[dA]–p[dT] DNA to obtain
C
50 values and a hairpin deoxyoligonucleotide containing an A/T-rich binding site was used to evaluate DNA binding affinity. It is observed that saturated heterocycles greatly reduce the DNA binding relative to distamycin.
A series of saturated heterocyclic analogues of distamycin was prepared and DNA binding affinity evaluated with a fluorescent intercalator displacement (FID) assay.