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Zeitschrift für Naturforschung B

A Journal of Chemical Sciences

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1H-[1,2,4]Triazolo[4,3-a]pyridin-4-ium and 3H-[1,2,4]triazolo[4,3-a]quinolin-10-ium derivatives as new intercalating agents for DNA

Marian Hebenbrock
  • Westfälische Wilhelms-Universität Münster, Institut für Anorganische und Analytische Chemie, Corrensstraße 28/30, 48149 Münster, Germany
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  • Westfälische Wilhelms-Universität Münster, Institut für Anorganische und Analytische Chemie, Corrensstraße 28/30, 48149 Münster, Germany, Phone: +49 251 83 36006
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Published Online: 2018-08-11 | DOI: https://doi.org/10.1515/znb-2018-0089

Abstract

Two new cationic DNA intercalators, 3-phenyl-1-(6-phenylpyridin-2-yl)-1H-[1,2,4]triazolo[4,3-a]pyridin-4-ium (1a)+ and 1-phenyl-3-(6-phenylpyridin-2-yl)-3H-[1,2,4]triazolo[4,3-a]quinolin-10-ium (1b)+, were synthesized from 2-chloropyridine and 2-chloroquinoline, respectively, in a four-step procedure. Generation of the hydrazine, followed by condensation with an aldehyde to give a hydrazone and subsequent Buchwald-Hartwig amination gave a mixture of E- and Z-configured N,N-functionalized hydrazones. Finally, oxidative cyclisation gave rise to the formation of the cationic DNA intercalators, whose molecular structures were determined by single-crystal X-ray diffraction analysis of the hexafluorophosphate and tribromide salt of (1a)+ and (1b)+, respectively. The intercalative binding of (1a)PF6 and (1b)PF6 to ctDNA was confirmed by means of UV, CD and luminescence spectroscopy, determination of the DNA melting temperature and by rheology measurements.

Graphical Abstract

Keywords: DNA; intercalator

Dedicated to: Professor Werner Uhl on the occasion of his 65th birthday.

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About the article

Received: 2018-05-11

Accepted: 2018-05-13

Published Online: 2018-08-11


Citation Information: Zeitschrift für Naturforschung B, 20180089, ISSN (Online) 1865-7117, ISSN (Print) 0932-0776, DOI: https://doi.org/10.1515/znb-2018-0089.

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