The Library
Ruthenium(II) arene anticancer complexes with redox-active diamine ligands
Tools
Tools
Tools
Bugarcic, Tijana, Habtemariam, Abraha, Deeth, Robert J., Fabbiani, Francesca P. A., Parsons, S. (Simon) and Sadler, P. J. (2009) Ruthenium(II) arene anticancer complexes with redox-active diamine ligands. Inorganic Chemistry, Vol.48 (No.19). pp. 9444-9453. doi:10.1021/ic9013366
Research output not available from this repository, contact author.
Official URL: http://dx.doi.org/10.1021/ic9013366
Abstract
The synthesis and characterization of ruthenium(II) arene complexes of the general formula [(eta(6)-arene)Ru(XY)Z](+), where arene = p-cymene (p-cym), hexamethyl benzene (hmb), or biphenyl (bip), XY = o-phenylenediamine (o-pda), o-benzoquinonediimine (o-bqdi), or 4,5-dimethyl-o-phenylenediamine (dmpda), and Z = Cl, Br, or l, are reported (complexes 1-6). In addition, the X-ray crystal structures of [(eta(6)-p-cym)Ru(o-pda)Cl]PF6 (1) and [(eta(6)-hmb)Ru-(o-bqdi)Cl]PF6 (3PF(6)) are described. The Ru-N distances in 3PF(6) are significantly shorter [2.033(4) and 2.025(4) angstrom] compared to those in 1 [2.141(2) and 2.156(2) angstrom], All of the imine complexes (3-5) exhibit a characteristic broad H-1 NMR NH resonance at ca. delta 14-15. Complex 1 undergoes concomitant ligand-based oxidation and hydrolysis (38% after 24 h) in water. The oxidation also occurs in methanol. The iodido complex [(eta(6)-p-cym)Ru(o-bqdi)l]l (4) did not undergo hydrolysis, whereas the chlorido complex 3 showed relatively fast hydrolysis (t(1/2) = 7.5 min). Density functional theory calculations showed that the total bonding energy of 9-EtG in [(eta(6)-p-cym)Ru(o-pda)(9-EtG-N7)](2+) (1EtG) is 23.8 kJ/mol lower than that in [(eta(6)-p-cym)Ru(o-bqdi)(9-EtG-N7)](2+) (3EtG). The greater bonding energy is related to the contribution from strong hydrogen bonding between the NH proton of the chelating ligand and O6 of 9-EtG (1.69 angstrom). A loss of cytotoxic activity was observed upon oxidation of the amine ligand to an imine (e.g., IC50 = 11 mu M for 1 and IC50 > 100 mu M for 3, against A2780 ovarian cancer cells). The relationship between the cytotoxic activity and the solution and solid state structures of the imine and amine complexes is discussed.
| Item Type: | Journal Article | ||||
|---|---|---|---|---|---|
| Subjects: | Q Science > QD Chemistry R Medicine > RS Pharmacy and materia medica |
||||
| Divisions: | Faculty of Science > Chemistry | ||||
| Library of Congress Subject Headings (LCSH): | Cell-mediated cytotoxicity, Phenylenediamines, Ruthenium compounds -- Therapeutic use, Aromatic compounds -- Therapeutic use, Transition metal complexes -- Therapeutic use, Antineoplastic agents | ||||
| Journal or Publication Title: | Inorganic Chemistry | ||||
| Publisher: | American Chemical Society | ||||
| ISSN: | 0020-1669 | ||||
| Official Date: | 5 October 2009 | ||||
| Dates: |
|
||||
| Volume: | Vol.48 | ||||
| Number: | No.19 | ||||
| Number of Pages: | 10 | ||||
| Page Range: | pp. 9444-9453 | ||||
| DOI: | 10.1021/ic9013366 | ||||
| Status: | Peer Reviewed | ||||
| Publication Status: | Published | ||||
| Access rights to Published version: | Restricted or Subscription Access | ||||
| Funder: | Oncosence Ltd., Overseas Research Students Award Scheme (ORSAS), University of Edinburgh, University of Warwick |
Data sourced from Thomson Reuters' Web of Knowledge
Request changes or add full text files to a record
Repository staff actions (login required)
 |
View Item |
