Distance dependent interhelical couplings of organic rods incorporated in DNA 4-helix bundles

Casper S. Andersen, Martin M. Knudsen, Rahul Chhabra, Yan Liu, Hao Yan, Kurt V. Gothelf

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

The synthesis of a conjugated linear organic module containing terminal salicylaldehyde groups and a central activated ester, designed for conjugation to amino-modified oligonucleotides, is presented. The organic module has a phenylene-ethynylene backbone and is highly fluorescent. It is conjugated to oligonucleotide sequences and incorporated into specific locations in a well-defined DNA 4-helix bundle (4-HB). The DNA-nanostructure offers precise location control of the organic modules which allows for selective interhelical coupling reactions. In this study, metal-salen formation as well as dihydrazone formation are used to covalently interlink the organic modules. Both coupling reactions are highly dependent on the distances between the organic modules in the 4-HB. Neighboring modules dimerize easier, whereas more distanced modules are less prone to react, even when the linkers are extended. The dimeric products are characterized by denaturing polyacrylamide gel electrophoresis (PAGE), high performance liquid chromatography (HPLC), and matrix assisted laser desorption/absorption ionization time-of-flight (MALDI TOF) mass spectrometry.

Original languageEnglish
Pages (from-to)1538-1546
Number of pages9
JournalBioconjugate Chemistry
Volume20
Issue number8
DOIs
Publication statusPublished - 2009

Fingerprint

Oligonucleotides
DNA
Nanostructures
High performance liquid chromatography
Polyacrylates
Electrophoresis
Ionization
Mass spectrometry
Polyacrylamide Gel Electrophoresis
Desorption
Mass Spectrometry
Esters
Lasers
Gels
Metals
High Pressure Liquid Chromatography
disalicylaldehyde ethylenediamine
salicylaldehyde
polyacrylamide gels

ASJC Scopus subject areas

  • Biotechnology
  • Bioengineering
  • Organic Chemistry
  • Pharmaceutical Science
  • Biomedical Engineering
  • Pharmacology

Cite this

Distance dependent interhelical couplings of organic rods incorporated in DNA 4-helix bundles. / Andersen, Casper S.; Knudsen, Martin M.; Chhabra, Rahul; Liu, Yan; Yan, Hao; Gothelf, Kurt V.

In: Bioconjugate Chemistry, Vol. 20, No. 8, 2009, p. 1538-1546.

Research output: Contribution to journalArticle

Andersen, Casper S. ; Knudsen, Martin M. ; Chhabra, Rahul ; Liu, Yan ; Yan, Hao ; Gothelf, Kurt V. / Distance dependent interhelical couplings of organic rods incorporated in DNA 4-helix bundles. In: Bioconjugate Chemistry. 2009 ; Vol. 20, No. 8. pp. 1538-1546.
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