Solid-Phase Synthesis and Photophysical Properties of DNA Labeled at the Nucleobase with Ru(bpy)₂(4-m-4‘-pa-bpy)²⁺

Abstract

A facile procedure for incorporating a Ru(diimine)(3)(2+) complex at the nucleobase in an oligonucleotide is reported that combines the advantages of Pd(0) cross-coupling and solid-phase DNA chemistries. These ruthenium-modified oligonucleotides form stable duplexes, and the favorable photophysical properties associated with the Ru(diimine)(3)(2+) complex are retained after site-specific covalent attachment.

Electron transfer dynamics of peptide‐derivatized RuII‐polypyridyl complexes on nanocrystalline metal oxide films

“…Solvents (Fisher Scientific), cis ‐Dichlorobis(2,2′‐bipyridine)ruthenium(II) dihydrate (Strem Chemicals), α‐ N ‐Fmoc‐lysine and α‐ N ‐Fmoc‐O‐benzyl‐ L ‐phosphoserine (Novabiochem), tetrakis(acetonitrile)copper(I) hexafluorophosphate, 2,2′‐bipyridine, 4,4′‐dimethyl‐2,2′‐bipyridine (Aldrich), and deuterated solvents (Cambridge Isotope Laboratories) were purchased from the corresponding supplier (in parentheses) and used without further purification. RuP , 4′‐methyl‐2,2′‐bipyridine‐4‐carboxaldehyde, 4′‐methyl‐2,2′‐bipyridine‐4‐carboxylic acid, and 4′‐methyl‐2,2′‐bipyridine‐4‐propargylamide were synthesized according to literature procedures 29–36…”

Luminescent Transition Metal Complexes as Biological Labels and Probes

“…33 cm -1 ) in the excited state, implying the localisation of the excited electron in the modified bipyridine unit that is directly linked to the uridine. This modified uridine has been incorporated into oligonucleotides by solid-phase synthesis [29]. The photophysical properties of the ruthenium(II)-labelled oligonucleotides and the duplexes formed with their complementary strands are similar to those of the original ruthenium(II) polypyridine complex.…”

“…Lo and co-workers synthesised a family of luminescent rhenium(I) polypyridine biotin complexes [Re(NˆN)(CO) 3 (py-spacer-biotin)] + (29) [67,68]. Upon irradiation, the complexes display orange to green triplet MLCT (dπ(Re) → π * (NˆN)) emission in fluid solutions at 298 K. The binding of the complexes to avidin has been studied by the standard HABA assay.…”

Ruthenium polypyridyl complex-containing bioconjugates

“…Thus, there is still place for the design, study and development of new bioconjugates, especially with uncommon biomolecules. We note that this review will not gather ruthenium-containing nucleotides and DNA conjugates [9,[33][34][35][36][37] since this was recently reviewed by our group. [38] We also note that Chao and co-workers recently reported a review on how to design metal complexes to target specific organelles.…”