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

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.

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, 59(4), 2367-2378. https://doi.org/10.1021/acs.inorgchem.9b03239

• Journal Article Type: Article
• Acceptance Date: Jan 13, 2020
• Online Publication Date: Jan 27, 2020
• Publication Date: Feb 17, 2020
• Deposit Date: Jan 27, 2020
• Publicly Available Date: Jan 28, 2021
• Journal: Inorganic chemistry
• Print ISSN: 0020-1669
• Electronic ISSN: 1520-510X
• Publisher: American Chemical Society
• Peer Reviewed: Peer Reviewed
• Volume: 59
• Issue: 4
• Pages: 2367-2378
• DOI: https://doi.org/10.1021/acs.inorgchem.9b03239
• Keywords: Rhenium; Ligands; Crystal structure; Ethanol; Mixtures
• Public URL: https://hull-repository.worktribe.com/output/3394214
• Publisher URL: https://pubs.acs.org/doi/abs/10.1021/acs.inorgchem.9b03239