Tricarbonylrhenium(I) complexes of phosphine-derivatized amines, amino acids and a model peptide: structures, solution behavior and cytotoxicity

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dc.contributor.authorZhang, Jianyong
dc.contributor.authorVittal, Jagadese J.
dc.contributor.authorHenderson, William
dc.contributor.authorWheaton, Jessica R.
dc.contributor.authorHall, Iris H.
dc.contributor.authorHor, T.S. Andy
dc.contributor.authorYan, Yaw Kai
dc.date.accessioned2009-11-19T23:17:05Z
dc.date.available2009-11-19T23:17:05Z
dc.date.issued2002
dc.description.abstractModified 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.en
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dc.identifier.citationZhang, J., Vittal, J. J., Henderson, W., Wheaton, J. R., Hall, I. H., Hor, T. S. A., & Yan, Y. K. (2002). Tricarbonylrhenium(I) complexes of phosphine-derivatized amines, amino acids and a model peptide: structures, solution behavior and cytotoxicity. Journal of Organometallic Chemistry, 650(1/2), 123-132.en
dc.identifier.doi10.1016/S0022-328X(02)01200-7en
dc.identifier.urihttps://hdl.handle.net/10289/3399
dc.language.isoen
dc.publisherElsevier Scienceen_NZ
dc.relation.isPartOfJournal of Organometallic Chemistryen_NZ
dc.rightsThis is an author’s accepted version of an article published in the Journal of Organometallic Chemistry. Copyright © 2002 Elsevier Science B.V. All rights reserved.en
dc.subjectchemistryen
dc.subjectamino acidsen
dc.titleTricarbonylrhenium(I) complexes of phosphine-derivatized amines, amino acids and a model peptide: structures, solution behavior and cytotoxicityen
dc.typeJournal Articleen
pubs.begin-page123en_NZ
pubs.elements-id27631
pubs.end-page132en_NZ
pubs.issue1-2en_NZ
pubs.volume650en_NZ
uow.identifier.article-noPII S0022-328X(02)01200-7en_NZ
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