PMID: 11902898Mar 21, 2002Paper

Organometallic ruthenium(II) diamine anticancer complexes: arene-nucleobase stacking and stereospecific hydrogen-bonding in guanine adducts

Journal of the American Chemical Society
Haimei ChenPeter J Sadler

Abstract

Organometallic ruthenium(II) arene anticancer complexes of the type [(eta(6)-arene)Ru(II)(en)Cl][PF(6)] (en = ethylenediamine) specifically target guanine bases of DNA oligomers and form monofunctional adducts (Morris, R., et al. J. Med. Chem. 2001). We have determined the structures of monofunctional adducts of the "piano-stool" complexes [(eta(6)-Bip)Ru(II)(en)Cl][PF(6)] (1, Bip = biphenyl), [(eta(6)-THA)Ru(II)(en)Cl][PF(6)] (2, THA = 5,8,9,10-tetrahydroanthracene), and [(eta(6)-DHA)Ru(II)(en)Cl][PF(6)] (3, DHA = 9,10-dihydroanthracene) with guanine derivatives, in the solid state by X-ray crystallography, and in solution using 2D [(1)H,(1)H] NOESY and [(1)H,(15)N] HSQC NMR methods. Strong pi-pi arene-nucleobase stacking is present in the crystal structures of [(eta(6)-C(14)H(14))Ru(en)(9EtG-N7)][PF(6)](2).(MeOH) (6) and [(eta(6)-C(14)H(12))Ru(en)(9EtG-N7)][PF(6)](2).2(MeOH) (7) (9EtG = 9-ethylguanine). The anthracene outer ring (C) stacks over the purine base at distances of 3.45 A for 6 and 3.31 A for 7, with dihedral angles of 3.3 degrees and 3.1 degrees, respectively. In the crystal structure of [(eta(6)-biphenyl)Ru(en)(9EtG-N7)][PF(6)](2).(MeOH) (4), there is intermolecular stacking between the pendant phenyl ring and th...Continue Reading

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Citations

Mar 10, 2010·Cancer Chemotherapy and Pharmacology·Emmanuel S Antonarakis, Ashkan Emadi
Mar 1, 2005·Journal of Biological Inorganic Chemistry : JBIC : a Publication of the Society of Biological Inorganic Chemistry·Fuyi WangPeter J Sadler
Apr 7, 2010·Journal of Biological Inorganic Chemistry : JBIC : a Publication of the Society of Biological Inorganic Chemistry·Lukas K FilakBernhard K Keppler
Mar 20, 2009·Journal of the American Society for Mass Spectrometry·Jonathan P WilliamsPeter J Sadler
Aug 6, 2013·Journal of Inorganic Biochemistry·Xuesong WangWeihong Du
Aug 15, 2013·Journal of Inorganic Biochemistry·Yu LinShaoxiang Xiong
Mar 31, 2011·Accounts of Chemical Research·Hong-Ke Liu, Peter J Sadler
Mar 23, 2013·Inorganic Chemistry·Aimee J GambleAdrian C Whitwood
Mar 30, 2011·Journal of Medicinal Chemistry·Zhe LiuPeter J Sadler
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Nov 29, 2005·Dalton Transactions : an International Journal of Inorganic Chemistry·Ioannis BratsosEnzo Alessio
Sep 30, 2005·Chemical Communications : Chem Comm·Yaw Kai YanPeter J Sadler
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Sep 18, 2009·Dalton Transactions : an International Journal of Inorganic Chemistry·Teresa GianferraraEnzo Alessio
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Jan 21, 2012·Metallomics : Integrated Biometal Science·Kui WuPeter J Sadler
Dec 15, 2005·Proceedings of the National Academy of Sciences of the United States of America·Fuyi WangPeter J Sadler
Mar 26, 2003·Proceedings of the National Academy of Sciences of the United States of America·Jan Reedijk
Dec 6, 2003·Proceedings of the National Academy of Sciences of the United States of America·Haimei ChenPeter J Sadler
Jun 6, 2009·Journal of Biological Inorganic Chemistry : JBIC : a Publication of the Society of Biological Inorganic Chemistry·Fuyi WangPeter J Sadler
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Apr 7, 2005·Current Opinion in Chemical Biology·Leigh Jk Boerner, Jeffrey M Zaleski

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