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Water-Soluble Rhenium Phosphine Complexes Incorporating the Ph2C(X) Motif (X = O–, NH–): Structural and Cytotoxicity Studies

Alshamrani, Abdullah F.; Prior, Timothy J.; Burke, Benjamin P.; Roberts, David P.; Archibald, Stephen J.; Higham, Lee J.; Stasiuk, Graeme; Redshaw, Carl

Authors

Abdullah F. Alshamrani

Benjamin P. Burke

David P. Roberts

Lee J. Higham

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Professor Carl Redshaw C.Redshaw@hull.ac.uk
Professor of Inorganic Materials Chemistry and REF Lead for Chemistry



Abstract

Reaction of [ReOCl3(PPh3)2] or [ReO2I(PPh3)2] with 2,2′-diphenylglycine (dpgH2) in refluxing ethanol afforded the air-stable complex [ReO(dpgH)(dpg)(PPh3)] (1). Treatment of [ReO(OEt)I2(PPh3)2] with 1,2,3-triaza-7-phosphaadamantane (PTA) afforded the complex [ReO(OEt)I2(PTA)2] (2). Reaction of [ReOI2(PTA)3] with dpgH2 led to the isolation of the complex [Re(NCPh2)I2(PTA)3]·0.5EtOH (3·0.5EtOH). A similar reaction but using [ReOX2(PTA)3] (X = Cl, Br) resulted in the analogous halide complexes [Re(NCPh2)Cl2(PTA)3]·2EtOH (4·2EtOH) and [Re(NCPh2)(PTA)3Br2]·1.6EtOH (5·1.6EtOH). Using benzilic acid (2,2′-diphenylglycolic acid, benzH) with 2 afforded the complex [ReO(benz)2(PTA)][PTAH]·EtOH (6·EtOH). The potential for the formation of complexes using radioisotopes with relatively short half-lives suitable for nuclear medicine applications by developing conditions for [Re(NCPh2)(dpg)I(PTA)3] (7)[ReO4]− in a 4 h time scale was investigated. A procedure for the technetium analog of complex [Re(NCPh2)I2(PTA)3] (3) from 99mTc[TcO4]− was then investigated. The molecular structures of 1–7 are reported; complexes 3–7 have been studied using in vitro cell assays (HeLa, HCT116, HT-29, and HEK 293) and were found to have IC50 values in the range of 29–1858 μM.

Journal Article Type Article
Publication Date Jan 27, 2020
Journal Inorganic Chemistry
Print ISSN 0020-1669
Electronic ISSN 1520-510X
Publisher American Chemical Society
Peer Reviewed Peer Reviewed
APA6 Citation Alshamrani, A. F., Prior, T. J., Burke, B. P., Roberts, D. P., Archibald, S. J., Higham, L. J., …Redshaw, C. (2020). Water-Soluble Rhenium Phosphine Complexes Incorporating the Ph2C(X) Motif (X = O–, NH–): Structural and Cytotoxicity Studies. Inorganic chemistry, https://doi.org/10.1021/acs.inorgchem.9b03239
DOI https://doi.org/10.1021/acs.inorgchem.9b03239
Keywords Physical and Theoretical Chemistry; Inorganic Chemistry; Rhenium; Ligands; Crystal structure; Ethanol Mixtures