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Title: Synthesis, photophysics, electrochemistry, and protein-binding studies of luminescent rhenium(I) polypyridine indole and biotin complexes
Other Titles: Ju fa guang xing lai duo bi ding yin duo ji sheng wu su luo he wu zhi he cheng, guang wu li, dian hua xue ji dan bai jie he zhi yan jiu
具發光性錸多吡啶吲哚及生物素絡合物之合成, 光物理, 電化學及蛋白結合之研究
Authors: Sze, Ka Shing (施加誠)
Department: Dept. of Biology and Chemistry
Degree: Master of Philosophy
Issue Date: 2007
Publisher: City University of Hong Kong
Subjects: Luminescent probes
Notes: CityU Call Number: TP248.25.L85 S94 2007
Includes bibliographical references (leaves 160-172)
Thesis (M.Phil.)--City University of Hong Kong, 2007
ix, 172 leaves : ill. ; 30 cm.
Type: Thesis
Abstract: A series of luminescent rhenium(I) dipyridoquinoxaline indole complexes [Re(N–N)(CO)3(py-spacer-indole)](CF3SO3) (N–N = dipyrido[3,2-f:2’,3’-h]quinoxaline (dpq), 2-(n-butylamido)dipyrido[3,2-f:2’,3’-h]quinoxaline (dpqa); py-spacer-indole = N-(3-pyridoyl)tryptamine (py-3-CONHC2H4-indole), N-(N-(3-pyridoyl)-6-aminohexanoyl)tryptamine (py-3-CONHC5H10CONHC2H4-indole)) and their indole-free counterparts [Re(N–N)(CO)3(py-3-CONH-Et)](CF3SO3) (N–N = dpq, dpqa; py-3-CONH-Et = N-ethyl-(3-pyridyl)formamide) have been synthesized and characterized. All the complexes exhibited triplet metal-to-ligand charge-transfer (3MLCT) (dπ(Re) → π*(diimine)) emission in fluid solutions at 298 K and in alcohol glass at 77 K. The emission quantum yields of the complexes were reduced upon changing the solvent from CH2Cl2 to aqueous buffer. The reduction for the dpqa complexes was much more significant compared to that for the dpq complexes due to the hydrogen-bonding interactions of the amide substituent of the dpqa ligand with water molecules. The interactions of these rhenium(I) complexes with indole-binding proteins including bovine serum albumin (BSA) and tryptophanase (TPase) have been studied by emission titrations and inhibition assays, respectively. The first class of luminescent biotinylating reagents that are derived from rhenium(I) polypyridine complexes [Re(N–N)(CO)3(py-biotin-NCS)](PF6) (N–N = 3,4,7,8-tetramethyl-1,10-phenanthroline (Me4-phen), 4,7-diphenyl-1,10-phenanthroline (Ph2-phen); py-biotin-NCS = 3-isothiocyanato-5-(N-((2-biotinamido)ethyl)aminocarbonyl)pyridine) including a biotin unit and an isothiocyanate moiety have been synthesized from the precursor amine complexes [Re(N–N)(CO)3(py-biotin-NH2)](PF6) (N–N = Me4-phen, Ph2-phen; py-biotin-NH2 = 3-amino-5-(N-((2-biotinamido)ethyl)aminocarbonyl)pyridine). To investigate the amine-specific reactivity of the isothiocyanate complexes, they have been reacted with a model substrate ethylamine, resulting in the formation of the thiourea complexes [Re(N–N)(CO)3(py-biotin-TU-Et)](PF6) (N–N = Me4-phen, Ph2-phen; py-biotin-TU-Et = 3-ethylthioureidyl-5-(N-((2-biotinamido)ethyl)aminocarbonyl)pyridine). All the rhenium(I) complexes have been characterized and their photophysical and electrochemical properties have been studied. The avidin-binding properties of the thiourea complexes have been examined by 4’-hydroxyazobenzene-2-carboxylic acid (HABA) assays and emission titrations. Additionally, BSA has been biotinylated with the isothiocyanate complexes. The emission and avidin-binding properties of the resultant rhenium-BSA bioconjugates have been investigated.
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