Issue 32, 2009

Oligopyridine–ruthenium(ii)–amino acid conjugates: synthesis, characterization, DNA binding properties and interactions with the oligonucleotide duplex d(5′-CGCGCG-3′)2

Abstract

Diastereomeric oligopyridine–ruthenium(II)amino acid conjugated complexes of the general formulas Λ- and Δ-[Ru(bpy)2(4,4′(CO2Y)2-bpy)]2+, where Y = L-AlaCONH2, L-LysCONH2, L-HisCONH2, L-TyrCONH2), were synthesized and characterized. Their binding properties with ct-DNA and the oligonucleotide duplex d(5′CGCGCG-3′)2, by means of circular dichroism (CD), NMR spectroscopy and DNA thermal denaturation (Tm) curves were studied. CD and Tm data indicate that all diastereomeric complexes bind to the DNA major groove, Δ-diastereomers in a similar manner, while Λ-diastereomers in dependence of the nature of the amino acid. NMR studies of d(5′CGCGCG-3′)2, and the complexes Δ-1, Δ-2, Λ-1 and Λ-2 indicate that Δ-1 and Δ-2 were bound having the ancillary bpy ligands towards the DNA groove, while the corresponding Λ-1 and Λ-2 were orientated in a similar way, facing the ligand 4,4′(CO2Y)2bpy towards the DNA major groove. Photoinduced DNA cleavage was observed in all cases studied, which take place through singlet oxygen production. Δ-4 and Λ-4 show the lower photoinduced cleavage yield, probably because the singlet oxygen (1O2) oxidizes not only the DNA phosporodiesteric bonds but the tyrosine's phenolic OH bond as well.

Graphical abstract: Oligopyridine–ruthenium(ii)–amino acid conjugates: synthesis, characterization, DNA binding properties and interactions with the oligonucleotide duplex d(5′-CGCGCG-3′)2

Article information

Article type
Paper
Submitted
11 Mar 2009
Accepted
18 May 2009
First published
30 Jun 2009

Dalton Trans., 2009, 6403-6415

Oligopyridineruthenium(II)amino acid conjugates: synthesis, characterization, DNA binding properties and interactions with the oligonucleotide duplex d(5′-CGCGCG-3′)2

K. Triantafillidi, K. Karidi, J. Malina and A. Garoufis, Dalton Trans., 2009, 6403 DOI: 10.1039/B904951G

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