Montagner, Diego and Gandin, Valentina and Marzano, Cristina and Longato, Bruno
(2011)
Synthesis, characterization and cytotoxic properties of platinum(II) complexes containing the nucleosides adenosine and cytidine.
Journal of Inorganic Biochemistry, 105.
pp. 919-926.
ISSN 0162-0134
Abstract
Cytidine (cyt) and adenosine (ado) react with cis-[L2Pt(μ-OH)]2(NO3)2 (L = PMe3, PPh3) in various solvents to give the nucleoside complexes cis-[L2Pt{cyt(− H),N3N4}]3(NO3)3 (L = PMe3, 1), cis-[L2Pt{cyt(− H),N4}(cyt,N3)]NO3 (L = PPh3, 2), cis-[L2Pt{ado(− H),N1N6}]2(NO3)2 (L = PMe3, 3) and cis-[L2Pt{ado(− H),N6N7}]NO3 (L = PPh3, 4). When the condensation reaction is carried out in solution of nitriles (RCN, R = Me, Ph) the amidine derivatives cis-[(PPh3)2PtNH=C(R){cyt(− 2H)}]NO3 (R = Me, 5a; R = Ph, 5b) and cis-[(PPh3)2PtNH=C(R){ado(− 2H)}]NO3 (R = Me, 6a: R = Ph, 6b) are quantitatively formed. The coordination mode of these nucleosides, characterized in solution by multinuclear NMR spectroscopy and mass spectrometry, is similar to that previously observed for the nucleobases 1-methylcytosine (1-MeCy) and 9-methyladenine (9-MeAd). The cytotoxic properties of the new complexes, and those of the nucleobase analogs, cis-[(PPh3)2PtNH=C(R){1-MeCy(− 2H)}]NO3 (R = Me, 7a: R = Ph, 7b), cis-[(PPh3)2PtNH=C(R){9-MeAd(− 2H)}]NO3 (R = Me, 8a: R = Ph, 8b) have been investigated in a wide panel of human cancer cells. Interestingly, whereas the Pt(II) nucleoside complexes (1–4) did not show appreciable cytotoxicity, the corresponding amidine derivatives (7a, 7b, 8a, 8b, 5b, and 6b) exhibited a significant in vitro antitumor activity.
Item Type: |
Article
|
Keywords: |
Nucleosides complexes of platinum(II);
Cytidine;
Adenosine;
Nitrile insertion;
Cytotoxicity; |
Academic Unit: |
Faculty of Science and Engineering > Chemistry |
Item ID: |
7049 |
Identification Number: |
https://doi.org/10.1016/j.jinorgbio.2011.03.009 |
Depositing User: |
Diego Montagner
|
Date Deposited: |
23 Mar 2016 12:01 |
Journal or Publication Title: |
Journal of Inorganic Biochemistry |
Publisher: |
Elsevier |
Refereed: |
Yes |
URI: |
|
Use Licence: |
This item is available under a Creative Commons Attribution Non Commercial Share Alike Licence (CC BY-NC-SA). Details of this licence are available
here |
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