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Review
. 2011 Jan 13;54(1):3-25.
doi: 10.1021/jm100020w. Epub 2010 Nov 15.

Organometallic anticancer compounds

Gilles Gasser  1 , Ingo Ott, Nils Metzler-Nolte
Affiliations
Free PMC article
Review

Organometallic anticancer compounds

Gilles Gasser et al. J Med Chem. .
Free PMC article
No abstract available

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Figures

Figure 1
Figure 1
Summary of the typical classes of organometallic compounds used in medicinal chemistry.
Scheme 1
Scheme 1. (Top Row) Classical Metallocenes with Parallel Cp Rings (Left) and Bent Metallocenes (Right) with the Medicinally Relevant Metals Indicated and (Bottom Row) Reversible Oxidation Chemistry of Ferrocene
Figure 2
Figure 2
Ferroquine (1) is presently the most advanced organometallic drug candidate and about to enter phase III clinical trials as an antimalarial drug.
Figure 3
Figure 3
Nucleoside analogue of ferrocene.
Figure 4
Figure 4
Tamoxifens and ferrocifens. The most active derivative of 5 with n = 4 is referred to as the ferrocifen.
Scheme 2
Scheme 2. Redox Activation of Ferrocifens as Proposed by Jaouen and Co-Workers
The ferrocene serves as a “redox antenna”. Following oxidation and proton abstraction a quinone methide is formed, which is readily attacked by nucleophiles at the positions indicated by arrows.
Figure 5
Figure 5
Titanocene Y (6) and the ansa-bridged derivatives titanocenes X (7) and Z (8).
Figure 6
Figure 6
Intracellular distribution of Mo (from Cp2MoCl2), Ti (from Cp2TiCl2), and K as shown by X-ray fluorescence microscopy. Reproduced from ref 102, with kind permission of Springer Science + Business Media.
Figure 7
Figure 7
(η6-Arene)ruthenium anticancer complexes.
Figure 8
Figure 8
RAPTA derivatives.
Figure 9
Figure 9
Ru arene enzyme inhibitors.
Figure 10
Figure 10
Ru arene chloroquinone antimalarial and antitumor agents.(136)
Figure 11
Figure 11
Structures of catalytically active organometallic anticancer complexes.
Figure 12
Figure 12
Ru arene anticancer complexes with redox-active diamine/diimmine ligands.
Figure 13
Figure 13
Os(II) arene anticancer compounds.
Figure 14
Figure 14
Triosmium clusters as potential inhibitors of telomerase enzyme. Ligand sites on Os denoted by (−) indicate CO ligands.
Figure 15
Figure 15
Examples of Rh(III), Ir(III), Rh(I), and Ir(I) cytotoxic organometallic compounds.
Figure 16
Figure 16
Cytotoxic Re organometallics.
Figure 17
Figure 17
Binding of ATP (left), staurosporine (middle), and ruthemium complexes (right) to the ATP-binding site of cyclin dependent kinase 2 (CDK2). The green area indicates a patch of high hydrophobicity. Adapted from refs (176) and (181).
Figure 18
Figure 18
Examples of Ru(II) organometallics as kinase inhibitors with their IC50 values. IC50 values were measured at 100 μM ATP if not indicated otherwise.
Figure 19
Figure 19
Schematic view of how the metal complex mimics the overall shape of staurosporine. Adapted from refs (177) and (182).
Figure 20
Figure 20
Metal NHC complexes.
Figure 21
Figure 21
Metal CO complexes.
Figure 22
Figure 22
Examples of Ru(II), Os(II), Rh(III), and Ir(III) organometallic porphyrin compounds.
Figure 23
Figure 23
Diarene ruthenium compound bridged by a ferrocene.(238)
Figure 24
Figure 24
Structure of the “complex-in-a-complex” cations [(acac)2MRu6(p-iPrC6H4Me)6(tpt)2(dhbq)3]6+ (66). Reproduced, with modification, with permission from Angewandte Chemie, International Edition.(242). Copyright 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
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