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Synthesis, characterization, and reaction pathways for the formation of a GMP adduct of a cytotoxic thiocyanato ruthenium arene complex
Wang, Fuyi1,3; Habtemariam, Abraha2,3; van der Geer, Erwin P. L.3; Deeth, Robert J.2; Gould, Robert3; Parsons, Simon3; Sadler, Peter J.2,3
2009-09-01
Source PublicationJOURNAL OF BIOLOGICAL INORGANIC CHEMISTRY
ISSN0949-8257
Volume14Issue:7Pages:1065-1076
AbstractThe organoruthenium complex [(eta(6)-hmb)Ru(en)(Cl)][PF(6)] (hmb is hexamethylbenzene, en is ethylenediamine) undergoes facile aquation and then reacts with KSCN in unbuffered solution to give the S-coordinated thiocyanato product [(eta(6)-hmb)Ru(en)(S-SCN)](+) which slowly converts to the thermodynamically favored N-bound complex [(eta(6)-hmb)Ru(en)(N-NCS)](+) (1 (+)). Complex 1 was synthesized and characterized by X-ray crystallography and mass spectrometry. Despite its lack of hydrolysis over 24 h, complex 1 exhibits moderate cytotoxicity (IC(50) 24 mu M) towards the human ovarian cancer cell line A2780, comparable with that of the chlorido analogue which is thought to be activated (towards potential target DNA) via a rapid aquation (Wang et. al. in Proc Natl Acad Sci USA 102:18269-18274, 2005). Detailed kinetic studies suggest that complex 1 binds to guanosine 5'-monophosphate (GMP) through direct N7 substitution of the N-bound SCN ligand. In the presence of a high concentration of chloride (104 mM), however, complex 1 may bind partly to GMP via Cl substitution.
KeywordOrganometallic Ruthenium Thiocyanate Ligand Anticancer Agents Gmp
DOI10.1007/s00775-009-0549-x
Indexed BySCI
Language英语
WOS IDWOS:000269912600007
PublisherSPRINGER
Citation statistics
Cited Times:4[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.iccas.ac.cn/handle/121111/67128
Collection中国科学院化学研究所
Corresponding AuthorWang, Fuyi
Affiliation1.Chinese Acad Sci, Inst Chem, Beijing Natl Lab Mol Sci, Beijing 100190, Peoples R China
2.Univ Warwick, Dept Chem, Coventry CV4 7AL, W Midlands, England
3.Univ Edinburgh, Sch Chem, Edinburgh EH9 3JJ, Midlothian, Scotland
Recommended Citation
GB/T 7714
Wang, Fuyi,Habtemariam, Abraha,van der Geer, Erwin P. L.,et al. Synthesis, characterization, and reaction pathways for the formation of a GMP adduct of a cytotoxic thiocyanato ruthenium arene complex[J]. JOURNAL OF BIOLOGICAL INORGANIC CHEMISTRY,2009,14(7):1065-1076.
APA Wang, Fuyi.,Habtemariam, Abraha.,van der Geer, Erwin P. L..,Deeth, Robert J..,Gould, Robert.,...&Sadler, Peter J..(2009).Synthesis, characterization, and reaction pathways for the formation of a GMP adduct of a cytotoxic thiocyanato ruthenium arene complex.JOURNAL OF BIOLOGICAL INORGANIC CHEMISTRY,14(7),1065-1076.
MLA Wang, Fuyi,et al."Synthesis, characterization, and reaction pathways for the formation of a GMP adduct of a cytotoxic thiocyanato ruthenium arene complex".JOURNAL OF BIOLOGICAL INORGANIC CHEMISTRY 14.7(2009):1065-1076.
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