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Tricarbonylrhenium(I) complexes of phosphine-derivatized amines, amino acids and a model peptide: structures, solution behavior and cytotoxicity |
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| Authors: | Jianyong Zhang Jagadese J Vittal William Henderson Jessica R Wheaton Iris H Hall T S Andy Hor and Yaw Kai Yan |
| Institution: | a Department of Chemistry, Faculty of Science, National University of Singapore, 3 Science Drive 3, Kent Ridge, Singapore 117543, Singapore b Department of Chemistry, University of Waikato, Private Bag 3105, Hamilton, New Zealand c Division of Medicinal Chemistry, School of Pharmacy, University of North Carolina, Chapel Hill, NC 27599-7360, USA d Natural Sciences, National Institute of Education, Block 7 (Science), Nanyang Technological University, 1 Nanyang Walk, Singapore 637616, Singapore |
| Abstract: | Modified Mannich reactions of amines, amino acids and a model peptide with Ph2PH and CH2O gave bis(diphenylphosphinomethyl)amines (Ph2PCH2)2NR R=Ph (1), CH2CH2OH (2), CH2COOCH2Ph (3), CH2CONHCH2COOCH2Ph (4), CH2COOH (5)] and (Ph2PCH2)2NCH2CH2N(CH2PPh2)2 (6). Reaction with ReBr3(CO)3]2− under mild conditions led to ReBr(CO)3]{(Ph2PCH2)2NR} R=Ph (7), CH2CH2OH (8), CH2COOCH2Ph (9), CH2CONHCH2COOCH2Ph (10), CH2COOH (11)] and ReBr(CO)3(Ph2PCH2)2NCH2]2 (12). All new complexes have been characterized by NMR and IR spectroscopy and for 7, 9 and 10, single-crystal X-ray diffraction analyses. Electrospray mass spectrometric studies show that the rhenium–phosphine chelates are very stable, especially in neutral methanolic solution. Hydrolysis of the ester and amide linkages slowly occur in acidic and basic solutions over several weeks; displacement of the bromide ligand also occurs in basic medium. Cytotoxicity testing of 7–10 and 12 showed that all the complexes are active against specific tumor cell lines, especially MCF-7 breast cancer and HeLa-S3 suspended uterine carcinoma. |
| Keywords: | Rhenium(I) Carbonyl Bis(diphenylphosphinomethyl)amine Cytotoxicity Electrospray mass spectrometry |
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