Purines Bearing Phenanthroline or Bipyridine Ligands and Their Ru^II Complexes in Position 8 as Model Compounds for Electrochemical DNA Labeling – Synthesis, Crystal Structure, Electrochemistry, Quantum Chemical Calculations, Cytostatic and Antiviral Activity

Abstract

A series of ethynyl-or (4-boronophenyl)bipyridines and -phenanthrolines were prepared as versatile building blocks for attachment of bidentate N-ligands to other molecules via cross-coupling reactions. Their complexation with Ru(bpy) 2 -Cl 2 gave the corresponding Ru II complexes. 9-Benzyladenine derivatives bearing the bipyridine or phenanthroline complexes in position 8, attached via a conjugate acetylene or phenylene linker were prepared by cross-coupling reactions of the ethynyl-or 4-boronophenylbipyridines and -phenanthrolines with 9-benzyl-8-bromoadenine. Their complexation with Ru(bpy) 2 Cl 2 afforded the corresponding Ru complexes as model compounds for electrochemical DNA labeling. The same compounds were also prepared directly by crosscoupling of 9-benzyl-8-bromoadenine with Ru complexes of the alkynes and boronic acids. Both approaches are compared in terms of potential applications for labeling of nucleic

Two sensors based on π-extended TTF: synthesis and high selectivity for copper(II)

“…The synthesis method is similar to the literature 23 . 5 (300mg, 0.815mmol), bis(pinacolato)diboron (414mg, 1.630mmol) were combined in anhydrous dioxane.…”

Mononuclear ruthenium(II) and rhodium(III) complexes with S-[4-(2,2:6′,2″-terpyridin-4′-yl)phenoxy]butyl ethanethioate and 4′-[4-(1,2-dithiolane-3-yl)butylcarboxy)phenyl]-2,2′:6′,2″-terpyridine: Synthesis, electrochemistry, antibacterial activity and catalytical application

“…Observed patterns of the spectra and values of the molar absorption coefficients for rhodium(III) complexes 5,9,11,13 are typical for the coordination compounds with the octahedral or slightly distorted octahedral ligand environment of the central ion Rh 3+ [35]. Absorption bands in the UV region (315-335 nm) are ascribed to ligand localized transitions, mainly the p ?…”

“…The possibility of tpy complexes interaction with the DNA molecules seems to allow them to combine cytotoxicity with antiviral properties. Ruthenium complexes, containing a purine [11] or 7-deaza-2 0 -deoxoadenozine [12] ligands, as well as bis-terpyridine complexes exhibited a considerable cytostatic effect and activity against the hepatitis C virus (HCV).…”

“…2.3.8. (S-[4-(2,2:6 0 ,2 00 -terpyridin-4 0 -yl)phenoxy]butyl ethanethioate)(phenantroline)chloro rhodium(III) dihexafluorophosphate, [Rh(phen)(Tpy-C 6 H 4 -O(CH 2 ) 4 -SCOCH 3 )Cl](PF 6 ) 2(11) The mixture of fac/mer-[RhCl 3 (phen)(CH 3 OH)]Á2H 2 O (1.15 eq.) and terpyridine(3)(1 eq.)…”

Pd-catalyzed allylic substitution of purin-8-yl(allyl) acetate: Route to (E)-alkenylpurines

“…Especially, various guanine/guanosine and adenine/adenosine derivatives bearing C 8 -sp 2 -carbon substituents have been prepared and studied as fluorescent/photosensitive [1][2][3][4][5] and electrochemical 6,7 marks in order to found a tool for the analysis of DNA or RNAs sequences. In addition, self-assebly of 8-aryl-2′-deoxyguanosine induced by the complexation of metal cations such as K + or Na + to dendrimers and oligomers was described 8 .…”