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Luminescent Polypyridinerhenium(I) Bis‐Biotin Complexes as Crosslinkers for Avidin
Author(s) -
Louie ManWai,
HoChuen Lam Marco,
KamWing Lo Kenneth
Publication year - 2009
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.200900518
Subject(s) - chemistry , avidin , bipyridine , luminescence , biotin , hela , fluorescence , pyridine , rhenium , medicinal chemistry , inorganic chemistry , crystallography , biochemistry , physics , optoelectronics , quantum mechanics , crystal structure , cell
Two novel luminescent polypyridinerhenium(I) bis‐biotin complexes [Re(NN)(CO) 3 (pyridine)](CF 3 SO 3 ) {NN = 4,4′‐bis{[2‐(biotinamido)ethyl]aminocarbonyl}‐2,2′‐bipyridine, bpyC2B2 ( 1 ), 4,4′‐bis[(2‐{[6‐(biotinamido)hexanoyl]amino}ethyl)aminocarbonyl]‐2,2′‐bipyridine, bpyC2C6B2 ( 2 )} and their biotin‐free counterpart [NN = 4,4′‐bis( n ‐butylaminocarbonyl)‐2,2′‐bipyridine, bpyC4 ( 3 )] have been synthesized and characterized. Upon irradiation, all the complexes exhibited triplet metal‐to‐ligand charge‐transfer ( 3 MLCT) emission in fluid solutions at room temperature and alcohol glass at 77 K. The avidin‐binding properties of the bis‐biotin complexes 1 and 2 have been studied by 4′‐hydroxyazobenzene‐2‐carboxylic acid (HABA) assays, emission titrations, and dissociation assays. The potential use of the complexes as signal amplifiers for heterogeneous recognition assays has been demonstrated using avidin‐coated microspheres and one of the complexes. Additionally, the cytotoxicity of these rhenium(I) complexes towards the human cervix epithelioid carcinoma (HeLa) cell line has been evaluated by 3‐(4,5‐dimethyl‐2‐thiazolyl)‐2,5‐diphenyltetrazolium bromide (MTT) assays. Furthermore, the cellular uptake of the complexes has been examined by laser‐scanning confocal microscopy. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)