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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 and Jens Müller EMAIL logo
Published/Copyright: August 11, 2018
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Zeitschrift für Naturforschung B
From the journal Zeitschrift für Naturforschung B Volume 73 Issue 11

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.

Keywords: DNA; intercalator

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

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Received: 2018-05-11
Accepted: 2018-05-13
Published Online: 2018-08-11
Published in Print: 2018-11-27

©2018 Walter de Gruyter GmbH, Berlin/Boston

Articles in the same Issue

  1. Frontmatter
  2. In this Issue
  3. Preface
  4. Congratulations to Bernt Krebs
  5. Structural and IR-spectroscopic characterization of pyridinium acesulfamate, a monoclinic twin
  6. Cationic tri(ferrocenecarbonitrile)silver(I)
  7. Ternary indides RE3T2In4 (RE=Dy–Tm; T=Pd, Ir)
  8. Mixing SbIII and GeIV occupancy in the polyoxovanadate {V14E8} archetype
  9. Biolabeling with cobaltocinium tags
  10. Formation of di- and polynuclear Mn(II) thiocyanate pyrazole complexes in solution and in the solid state
  11. Hydrothermal synthesis and structure determination of a new calcium iron ruthenium hydrogarnet
  12. 7-Methyl-6-furylpurine forms dinuclear metal complexes with N3,N9 coordination
  13. Structural and magnetic investigations of the pseudo-ternary RE2TAl3 series (RE=Sc, Y, La–Nd, Sm, Gd–Lu; T=Ru, Rh, Ir) – size dependent formation of two different structure types
  14. A new stacking variant of Na2Pt(OH)6
  15. Alkali chalcogenido ortho manganates(II) A6MnQ4 (A=Rb, Cs; Q=S, Se, Te)
  16. Studie über den Einfluss des Fluorierungsgrades an einem tetradentaten C^N*N^C-Luminophor auf die photophysikalischen Eigenschaften seiner Platin(II)-Komplexe und deren Aggregation
  17. Hydrothermal growth mechanism of SnO2 nanorods in aqueous HCl
  18. Preface
  19. Congratulations to Werner Uhl
  20. The stannides REIr2Sn4 (RE=La, Ce, Pr, Nd, Sm)
  21. 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
  22. Functionalization of 1,3-diphosphacyclobutadiene cobalt complexes via Si–P bond insertion
  23. A new aspect of the “pseudo water” concept of bis(trimethylsilyl)carbodiimide – “pseudohydrates” of aluminum
  24. (NH4)InB8O14 – a high-pressure borate combining BO3 groups with corner- and edge-sharing BO4 tetrahedra
  25. Two series of rare earth metal-rich ternary aluminium transition metallides – RE6Co2Al (RE=Sc, Y, Nd, Sm, Gd–Tm, Lu) and RE6Ni2.25Al0.75 (RE=Y, Gd–Tm, Lu)
  26. Alkylaluminum, -gallium, -magnesium, and -zinc monophenolates with bulky substituents
  27. Note
  28. Synthesis and crystal structure of the copper silylamide cluster compound [Cu9{MesSi(NPh)3}2 (PhCO2)3]
https://doi.org/10.1515/znb-2018-0089
Keywords for this article
DNA; intercalator

Articles in the same Issue

  1. Frontmatter
  2. In this Issue
  3. Preface
  4. Congratulations to Bernt Krebs
  5. Structural and IR-spectroscopic characterization of pyridinium acesulfamate, a monoclinic twin
  6. Cationic tri(ferrocenecarbonitrile)silver(I)
  7. Ternary indides RE3T2In4 (RE=Dy–Tm; T=Pd, Ir)
  8. Mixing SbIII and GeIV occupancy in the polyoxovanadate {V14E8} archetype
  9. Biolabeling with cobaltocinium tags
  10. Formation of di- and polynuclear Mn(II) thiocyanate pyrazole complexes in solution and in the solid state
  11. Hydrothermal synthesis and structure determination of a new calcium iron ruthenium hydrogarnet
  12. 7-Methyl-6-furylpurine forms dinuclear metal complexes with N3,N9 coordination
  13. Structural and magnetic investigations of the pseudo-ternary RE2TAl3 series (RE=Sc, Y, La–Nd, Sm, Gd–Lu; T=Ru, Rh, Ir) – size dependent formation of two different structure types
  14. A new stacking variant of Na2Pt(OH)6
  15. Alkali chalcogenido ortho manganates(II) A6MnQ4 (A=Rb, Cs; Q=S, Se, Te)
  16. Studie über den Einfluss des Fluorierungsgrades an einem tetradentaten C^N*N^C-Luminophor auf die photophysikalischen Eigenschaften seiner Platin(II)-Komplexe und deren Aggregation
  17. Hydrothermal growth mechanism of SnO2 nanorods in aqueous HCl
  18. Preface
  19. Congratulations to Werner Uhl
  20. The stannides REIr2Sn4 (RE=La, Ce, Pr, Nd, Sm)
  21. 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
  22. Functionalization of 1,3-diphosphacyclobutadiene cobalt complexes via Si–P bond insertion
  23. A new aspect of the “pseudo water” concept of bis(trimethylsilyl)carbodiimide – “pseudohydrates” of aluminum
  24. (NH4)InB8O14 – a high-pressure borate combining BO3 groups with corner- and edge-sharing BO4 tetrahedra
  25. Two series of rare earth metal-rich ternary aluminium transition metallides – RE6Co2Al (RE=Sc, Y, Nd, Sm, Gd–Tm, Lu) and RE6Ni2.25Al0.75 (RE=Y, Gd–Tm, Lu)
  26. Alkylaluminum, -gallium, -magnesium, and -zinc monophenolates with bulky substituents
  27. Note
  28. Synthesis and crystal structure of the copper silylamide cluster compound [Cu9{MesSi(NPh)3}2 (PhCO2)3]
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