Tröger's base scaffold in racemic and chiral fashion as a spacer for bisdistamycin formation. Synthesis and DNA binding study

‘Head-to-head’ oligo- N-methylpyrrole peptide dimers linked by a methano[1,5]diazocin scaffold are presented in racemic as well as chiral fashion. Their DNA binding activities were assayed on calf thymus DNA, poly(dA-dT) 2, and poly(dC-dG) 2 by NMR and ECD spectroscopies, and fluorescence probe disp...

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Bibliographic Details
Published in:Tetrahedron 2006-09, Vol.62 (36), p.8591-8600
Main Authors: Valík, Martin, Malina, Jaroslav, Palivec, Lukáš, Foltýnová, Jarmila, Tkadlecová, Marcela, Urbanová, Marie, Brabec, Viktor, Král, Vladimír
Format: Article
Language:English
Subjects:
Dissymmetry factor
Distamycin dimer
Enantioselective binding
Tröger's base
VCD
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Summary:‘Head-to-head’ oligo- N-methylpyrrole peptide dimers linked by a methano[1,5]diazocin scaffold are presented in racemic as well as chiral fashion. Their DNA binding activities were assayed on calf thymus DNA, poly(dA-dT) 2, and poly(dC-dG) 2 by NMR and ECD spectroscopies, and fluorescence probe displacement assay. The presented dimers prefer AT sequences, but show higher affinity to poly(dC-dG) 2 than distamycin A. The (4 R,9 R) configuration of methanodiazocin bridge was found to be better suited for interaction with ct-DNA and poly(dA-dT) 2 than (4 S,9 S) configuration. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2006.06.056