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Chemistry. 2013 Nov 18;19(47):15924-32. doi: 10.1002/chem.201301776. Epub 2013 Oct 8.

Cyclometalated iridium(III) complexes with deoxyribose substituents.

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  • 1Department of Chemistry, Case Western Reserve University, 10900 Euclid Avenue, Cleveland Ohio 44106 (USA).

Abstract

Fundamental study of enzymatic nucleoside transport suffers for lack of optical probes that can be tracked noninvasively. Nucleoside transporters are integral membrane glycoproteins that mediate the salvage of nucleosides and their passage across cell membranes. The substrate recognition site is the deoxyribose sugar, often with little distinction among nucleobases. Reported here are nucleoside analogues in which emissive, cyclometalated iridium(III) complexes are "clicked" to C-1 of deoxyribose in place of canonical nucleobases. The resulting complexes show visible luminescence at room temperature and 77 K with microsecond-length triplet lifetimes. A representative complex is crystallographically characterized. Transport and luminescence are demonstrated in cultured human carcinoma (KB3-1) cells.

Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

KEYWORDS:

click chemistry; fluorescent probes; iridium; metalation; nucleobases

[PubMed - indexed for MEDLINE]
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