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Synthesis and crystal structure of cis-diammineplatinum α-pyridone blue

Barton, J. K. and Rabinowitz, H. N. and Szalda, D. J. and Lippard, S. J. (1977) Synthesis and crystal structure of cis-diammineplatinum α-pyridone blue. Journal of the American Chemical Society, 99 (8). pp. 2827-2829. ISSN 0002-7863. http://resolver.caltech.edu/CaltechAUTHORS:20170707-154241416

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Abstract

The blue compounds formed from aqueous solutions of platinum(II) in the presence of amides have been a subject of study since the original report of “Platinblau” in 1908.[1-3] Recent interest in these complexes was sparked by the discovery that aquated products of the antitumor drug cis-dichlorodiammineplatinum(II) undergo a slow reaction with polyuracil, uracil, thymine, and related pyrimidines (1) to form blue complexes. [4] The platinum pyrimidine blues have antitumor activity of their own [4,5] and are useful electron microscopic stains for DNA.[6] Attempts to crystallize these blue complexes have been largely unsuccessful because they are oligomeric mixtures of varying degrees of hydrolytic instability.[7] With synthetic insights provided by the detailed studies of Lerner [7] and the choice of α-pyridone (2) as the amide ligand [8], we have obtained a crystalline platinum blue and determined its structure by x-ray crystallography.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja00450a085DOIArticle
http://pubs.acs.org/doi/pdf/10.1021/ja00450a085PublisherArticle
ORCID:
AuthorORCID
Barton, J. K.0000-0001-9883-1600
Additional Information:© 1977 American Chemical Society. Received February 2, 1977. This work was supported by National Institutes of Health Research Grant No. CA-15826 and by a National Research Service Award (to D.J.S.) No. CA-05806, both from the National Cancer Institute. We also thank the National Science Foundation for a Predoctoral Fellowship to J. K. B., Engelhard Industries for a generous loan of K_2PtCl_4, and P. Aisen for advice about integrating the electron spin resonance spectrum.
Funders:
Funding AgencyGrant Number
NIHCA-15826
NIH Predoctoral FellowshipCA-05806
NSF Predoctoral FellowshipUNSPECIFIED
Engelhard IndustriesUNSPECIFIED
Record Number:CaltechAUTHORS:20170707-154241416
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20170707-154241416
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:78874
Collection:CaltechAUTHORS
Deposited By: Donna Wrublewski
Deposited On:10 Jul 2017 17:03
Last Modified:10 Jul 2017 17:03

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