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Organometallic Half-Sandwich Iridium Anticancer Complexes
Open accessAbstract
The low-spin 5d(6) Ir(III) organometallic half-sandwich complexes [(η(5)-Cp(x))Ir(XY)Cl](0/+), Cp(x) = Cp*, tetramethyl(phenyl)cyclopentadienyl (Cp(xph)), or tetramethyl(biphenyl)cyclopentadienyl (Cp(xbiph)), XY = 1,10-phenanthroline (4-6), 2,2'-bipyridine (7-9), ethylenediamine (10 and 11), or picolinate (12-14), hydrolyze rapidly. Complexes with N,N-chelating ligands readily form adducts with 9-ethylguanine but not 9-ethyladenine; picolinate complexes bind to both purines. Cytotoxic potency toward A2780 human ovarian cancer cells increases with phenyl substitution on Cp*: Cp(xbiph) > Cp(xph) > Cp*; Cp(xbiph) complexes 6 and 9 have submicromolar activity. Guanine residues are preferential binding sites for 4-6 on plasmid DNA. Hydrophobicity (log P), cell and nucleus accumulation of Ir correlate with cytotoxicity, 6 > 5 > 4; they distribute similarly within cells. The ability to displace DNA intercalator ethidium bromide from DNA correlates with cytotoxicity and viscosity of Ir-DNA adducts. The hydrophobicity and intercalative ability of Cp(xph) and Cp(xbiph) make a major contribution to the anticancer potency of their Ir(III) complexes.
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Metadata
- Authors
- Liu, Z., Habtemariam, A., Pizarro, A. M., Fletcher, S. A., Kisova, A., Vrana, O., Salassa, L., Bruijnincx, P. C. A., Clarkson, G. J., Brabec, V., & Sadler, P. J.
- Venue
- Journal of Medicinal Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2011-03-28
- Volume
- 54
- Issue
- 8
- Pages
- 3011-3026
- ISSN
- 0022-2623 (ISSN-L)
- 1520-4804
- OpenAlex
- W2138236417
- Cited by
- 357
- References
- 49
- FWCI
- 9.24
- Type
- journal article
- Language
- en
- Open access
- green
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- Liu, Z., Habtemariam, A., Pizarro, A. M., Fletcher, S. A., Kisova, A., Vrana, O., Salassa, L., Bruijnincx, P. C. A., Clarkson, G. J., Brabec, V., & Sadler, P. J. (2011). Organometallic Half-Sandwich Iridium Anticancer Complexes. Journal of Medicinal Chemistry. https://doi.org/10.1021/jm2000932
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