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The contrasting chemistry and cancer cell cytotoxicity of bipyridine and bipyridinediol ruthenium(II) arene complexes
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Bugarcic, Tijana, Habtemariam, Abraha, Stepankova, Jana, Heringova, Pavla, Kasparkova, Jana, Deeth, Robert J., Johnstone, Russell D. L., Prescimone, Alessandro, Parkin, Andrew, Parsons, S. (Simon), Brabec, V. (Viktor) and Sadler, P. J. (2008) The contrasting chemistry and cancer cell cytotoxicity of bipyridine and bipyridinediol ruthenium(II) arene complexes. Inorganic Chemistry, Vol.47 (No.24). pp. 11470-11486. doi:10.1021/ic801361m ISSN 0020-1669.
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Official URL: http://dx.doi.org/10.1021/ic801361m
Abstract
The synthesis and characterization of ruthenium(II) arene complexes [(eta(6)-arene)Ru(N,N)Cl](0/+), where N,N = 2,2'-bipyridine (bipy), 2,2'-bipyridine-3,3'-diol (bipy(OH)(2)) or deprotonated 2,2'-bipyridine-3,3'-diol (bipy(OH)O) as N,N-chelating ligand, arene = benzene (bz), indan (ind), biphenyl (bip), rho-terphenyl (rho-terp), tetrahydronaphthalene (thn), tetrahydroanthracene (tha) or dihydroanthracene (dha), are reported, including the X-ray crystal structures of [(eta(6)-tha)Ru(bipy)Cl][PF6] (1), [(eta(6)-tha)Ru(bipy(OH)O)Cl] (2) and [(eta(6)-ind)Ru(bipy(OH)(2))Cl][PF6] (8). Complexes 1 and 2 exibit CH (arene)/pi (bipy or bipy(OH)O) interactions. In the X-ray structure of protonated complex 8, the pyridine rings are twisted (by 17.31 degrees). In aqueous solution (pH = 2-10), only deprotonated (bipy(OH)0) forms are present. Hydrolysis of the complexes was relatively fast in aqueous solution (t1/2 = 4-15 min, 310 K). When the arene is biphenyl, initial aquation of the complexes is followed by partial arene loss. Complexes with arene = tha, thn, dha, ind and rho-terp, and deprotonated bipyridinediol (bipy(OH)O) as chelating ligands, exhibited significant cytotoxicity toward A2780 human ovarian and A549 human lung cancer cells. Complexes [(eta(6)-bip)Ru(bipy(OH)O)Cl] (7) and [(eta(6)-bz)Ru(bipy(OH)O)Cl] (5) exhibited moderate cytotoxicity toward A2780 cells, but were inactive toward A549 cells. These activity data can be contrasted with those of the parent bipyridine complex [(eta(6)-tha)Ru(bipy)Cl][PF6] (1) which is inactive toward both A2780 ovarian and A549 lung cell lines. DFT calculations suggested that hydroxylation and methylation of the bipy ligand have little effect on the charge on Ru. The active complex [(eta(6)-tha)Ru(bipy(OH)O)Cl] (2) binds strongly to 9-ethyl-guanine (9-EtG). The X-ray crystal structure of the adduct [(eta(6)-tha)Ru(bipy(OH)O)(9-EtG-N7)][PF6] shows intramolecular CH (arene)/pi (bipy(OH)O) interactions and DFT calculations suggested that these are more stable than arene/9-EtG pi-pi interactions. However [(eta(6)-ind)Ru(bipy(OH)(2))Cl][PF6] (8) and [(eta(6-)ind)Ru(bipy)Cl][PF6] (16) bind only weakly to DNA. DNA may therefore not be the major target for complexes studied here.
Item Type: | Journal Article | ||||
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Subjects: | Q Science > QD Chemistry | ||||
Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | ||||
Library of Congress Subject Headings (LCSH): | Cell-mediated cytotoxicity, Cancer cells, Aromatic compounds | ||||
Journal or Publication Title: | Inorganic Chemistry | ||||
Publisher: | American Chemical Society | ||||
ISSN: | 0020-1669 | ||||
Official Date: | 15 December 2008 | ||||
Dates: |
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Volume: | Vol.47 | ||||
Number: | No.24 | ||||
Number of Pages: | 17 | ||||
Page Range: | pp. 11470-11486 | ||||
DOI: | 10.1021/ic801361m | ||||
Status: | Peer Reviewed | ||||
Publication Status: | Published | ||||
Access rights to Published version: | Restricted or Subscription Access | ||||
Funder: | Czech Republic. Ministerstvo Å¡kolstvÃ, mládeže a tÄ›lovýchovy [Czech Republic. Ministry of Education, Youth, and Sport], Akademie vÄ›d ÄŒeské republiky [Academy of Sciences of the Czech Republic] (ASCR), Ministerstvo zdravotnictvà České republiky [Ministry of Health of the Czech Republic] (MZCR) | ||||
Grant number: | LC06030 (MSMT), 6198959216 (MSMT), ME08017 (MSMT), OC08003 (MSMT), 1QS500040581 (ASCR), KAN200200651 (ASCR), AV0Z50040507 (ASCR), AV0Z50040702 (ASCR), IAA400040803 (ASCR), NR8562-4/2005 (MZCR) |
Data sourced from Thomson Reuters' Web of Knowledge
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