Tri- and tetra-substituted naphthalene diimides as potent G-quadruplex ligands

A series of tri- and tetra-substituted naphthalene diimides have been designed and synthesized. Several compounds show exceptional affinity for telomeric G-quadruplex DNA in classical and competition FRET assays and SPR studies. They inhibit telomerase in the TRAP assay, and show potent senescence-b...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry 2008-03, Vol.18 (5), p.1668-1673
Main Authors: Cuenca, Francisco, Greciano, Olga, Gunaratnam, Mekala, Haider, Shozeb, Munnur, Deeksha, Nanjunda, Rupesh, Wilson, W. David, Neidle, Stephen
Format: Article
Language:English
Subjects:
Antineoplastic agents
Antineoplastic Agents - chemistry
Antineoplastic Agents - metabolism
Antineoplastic Agents - pharmacology
Biological and medical sciences
Cell Line, Tumor
Fluorescence Resonance Energy Transfer
G-quadruplex
G-Quadruplexes
General aspects
Humans
Imides
Ligands
Medical sciences
Models, Molecular
Molecular Structure
Naphthalenes
Pharmacology. Drug treatments
Phenanthrolines - chemistry
Phenanthrolines - metabolism
Phenanthrolines - pharmacology
Telomerase - antagonists & inhibitors
Telomerase inhibition
Telomere
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Summary:A series of tri- and tetra-substituted naphthalene diimides have been designed and synthesized. Several compounds show exceptional affinity for telomeric G-quadruplex DNA in classical and competition FRET assays and SPR studies. They inhibit telomerase in the TRAP assay, and show potent senescence-based short-term anti-proliferative effects on MCF7 and A549 cancer cell lines, and localize in the nucleus and particularly the nucleolus of MCF7 cells.
ISSN:0960-894X
0968-0896
1464-3405
1464-3391
DOI:10.1016/j.bmcl.2008.01.050