Synthesis of distamycin A polyamides targeting G-quadruplex DNA

A number of amide-linked oligopyrroles based on distamycin molecules have been synthesized by solid-state methods, and their interactions with a human intramolecular G-quadruplex have been measured by a melting procedure. Several of these molecules show an enhanced ratio of quadruplex vs. duplex DNA...

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Bibliographic Details
Published inOrganic & biomolecular chemistry Vol. 4; no. 18; pp. 3479 - 3488
Main Authors Moore, Michael J. B., Cuenca, Francisco, Searcey, Mark, Neidle, Stephen
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 01.01.2006
Subjects
Chemistry
Chemistry, Organic
Dimerization
Distamycins - chemical synthesis
Distamycins - chemistry
DNA - chemistry
Fluorescence Resonance Energy Transfer
G-Quadruplexes
Humans
Models, Molecular
Nylons - chemical synthesis
Nylons - chemistry
Physical Sciences
Science & Technology
Thermodynamics
CELLS
MINOR-GROOVE RECOGNITION
HUMAN TELOMERASE INHIBITION
LIGANDS
SOLID-PHASE SYNTHESIS
ANTITUMOR POLYCYCLIC ACRIDINES
BIOLOGICAL-ACTIVITY
SENESCENCE
IMIDAZOLE
BINDING
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Summary:A number of amide-linked oligopyrroles based on distamycin molecules have been synthesized by solid-state methods, and their interactions with a human intramolecular G-quadruplex have been measured by a melting procedure. Several of these molecules show an enhanced ratio of quadruplex vs. duplex DNA binding compared to distamycin itself, including one with a 2,5-disubstituted pyrrole group. Quadruplex affinity increases with the number of pyrrole groups, and it is suggested that this is consistent with a mixed groove/G-quartet stacking binding mode.
ISSN:1477-0520
1477-0539
DOI:10.1039/b607707b