Nucleic Acid Intercalators and Avidin Probes Derived from Luminescent Cyclometalated Iridium(III)–Dipyridoquinoxaline and –Dipyridophenazine Complexes

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Abstract
Six luminescent cyclometalated iridium(III)–dipyridoquinoxaline and –dipyridophenazine complexes [Ir(ppy)2(N‐N)](PF6) (Hppy=2‐phenylpyridine; N‐N=dipyrido[3,2‐f:2′,3′‐h]quinoxaline, dpq (1); 2‐n‐butylamidodipyrido[3,2‐f:2′,3′‐h]quinoxaline, dpqa (2); 2‐((2‐biotinamido)ethyl)amidodipyrido[3,2‐f:2′,3′‐h]quinoxaline, dpqB (3); dipyrido[3,2‐a:2′,3′‐c]phenazine, dppz (4); benzo[i]dipyrido[3,2‐a:2′,3′‐c]phenazine, dppn (5); 11‐((2‐biotinamido)ethyl)amidodipyrido[3,2‐a:2′,3′‐c]phenazine, dppzB (6)) have been designed as luminescent intercalators for DNA and probes for avidin. The structure of complex 4 has been studied by X‐ray crystallography. The photophysical and electrochemical properties of the complexes have also been investigated. The binding of these complexes to double‐stranded calf thymus DNA and synthetic double‐stranded oligonucleotides poly(dA)⋅poly(dT) and poly(dG)⋅poly(dC) has been investigated by spectroscopic titrations. The interactions between the two biotin‐containing complexes and avidin have been studied by 4′‐hydroxyazobenzene‐2‐carboxylic acid (HABA) assays and emission titrations.

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