Alkyne hexacarbonyl dicobalt complexes in medicinal chemistry and drug development

Expert Opinion on Therapeutic Patents

Volumn 18, Issue 3, 2008, Pages 327-337

  Ott, Ingo ^a   Kircher, Brigitte ^b   Dembinski, Roman ^c   Gust, Ronald ^a  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

^b INNSBRUCK MEDICAL UNIVERSITY   (Austria)

^c OAKLAND UNIVERSITY   (United States)

Author keywords

Alkyne complexes; Antitumor; Carbonylmetalloimmunoassay; Cobalt carbonyl complexes; Hexacarbonyl dicobalt

Indexed keywords

ACETYLSALICYLIC ACID DERIVATIVE; ALKYNE DERIVATIVE; ALKYNE HEXACARBONYL DICOBALT COMPLEX; ANTINEOPLASTIC AGENT; CARBAMAZEPINE; CARBON MONOXIDE; CARBOPLATIN; CISPLATIN; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; CYTOSTATIC AGENT; DIAGNOSTIC AGENT; ETHINYLESTRADIOL; ETHISTERONE; HORMONE DERIVATIVE; IMATINIB; LIGAND; NEUROPEPTIDE; NONSTEROID ANTIINFLAMMATORY AGENT; ORGANOMETALLIC COMPOUND; TRACER; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; CANCER CELL CULTURE; CELL GROWTH; CELL PROLIFERATION; CHEMICAL REACTION; CYTOTOXICITY; DATA BASE; DRUG MECHANISM; DRUG METABOLISM; DRUG POTENTIATION; DRUG STABILITY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; IC 50; INHIBITION KINETICS; INTERNET; LIPOPHILICITY; MEDICAL RESEARCH; MEDLINE; NONHUMAN; PHYSICAL CHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE; REVIEW;

EID: 42549112220     PISSN: 13543776     EISSN: None     Source Type: Journal    
DOI: 10.1517/13543776.18.3.327     Document Type: Review

References (76)

1. Galanski M, Jakupec MA, Keppler BK. Update of the preclinical situation of anticancer platinum complexes: novel design strategies and innovative analytical approaches. Curr Med Chem 2005;12:2075-94
2. Jakupec MA, Galanski M, Keppler BK. Tumour-inhibiting platinum complexes: state of the art and future perspectives. Rev Physiol Biochem Pharmacol 2003;146:1-53
3. Ott I, Gust R. Non-platinum complexes as anticancer drugs. Arch Pharm Chem Life Sci 2007;340:117-26
4. Meggers E. Exploring biologically relevant chemical apace with metal complexes. Curr Opin Chem Biol 2007;11:287-92
5. Hambley TW. Metal-based therapeutics. Science 2007;318:1392-3
6. Hartinger CG, Zorbas-Seifried S, Jakupec MA, et al. From bench to bedside: preclinical and early clinical development of the anticancer agent indazolium trans-[tetrachlorobis(1H-indazole) ruthenate(III)] (KP1019 or FFC14A). J Inorg Biochem 2006;100:891-904
7. Ware DC, Palmer BD, Wilson WR, et al. Hypoxia selective antitumor agents. 7. Metal complexes of aliphatic mustards as a new class of hypoxia-selective cytotoxins. Synthesis and evaluation of cobalt(III) complexes of bidentate mustards. J Med Chem 1993;36:1839-46
8. Ware DC, Palmer BD, Brothers BJ, et al. Bis-tropolonato derivatives of cobalt (III) complexes of aliphatic bidentate nitrogen mustards as potential hypoxia-selective cytotoxins. J Inorg Biochem 1997;68:215-24
9. Failes TW, Hambley TW. Models of hypoxia activated prodrugs: cobalt(III) complexes of hydroxamates. Dalton Trans 2006;1895-901
10. Failes TW, Cullinane C, Diakos CI. Studies of a cobalt(III) complex of the MMP inhibitor marimastat: a potential hypoxia-activated prodrug. Chem Eur J 2007;13(10):2974-82
11. Teicher BA, Jacobs JL, Cathcart CN, et al. Some complexes of cobalt(III) and iron(III) are radiosensitizers of hypoxic EMT6 cells. Radiat Res 1987;109(1):36-46
12. Ahn GO, Ware DC, Denny WA, Wilson WR. Optimization of the auxiliary ligand shell of cobalt(III) (8-hydroxyquinoline) complexes as model hypoxia-selective radiation-activated prodrugs. Radiat Res 2004;162(3):315-25
13. Ahn GO, Botting KJ, Patterson AV, et al. Rarliolytic and cellular reduction of a novel hypoxia-activated cobalt(III) prodrug of chloromethylbenzindoline DNA minor groove alkylator. Biochem Pharmacol 2006;71(12):1683-94
14. Hall MD, Failes TW, Yamamoto N, Hambley TW. Bioreductive activation and drug chaperoning in cobalt pharmaceuticals. Dalton Trans 2007;3983-90
15. 3]+ and recognized by the L-type amino acid transporter LAT1. J Am Chem Soc 2006;128:15996-7
16. 3]+ (M=99mTc, Re)-based complexes conjugated to acridine orange and bombesin. Chemistry 2007;13:3842-52
17. Smalley KSM, Contractor R, Haass N, et al. An organometallic protein kinase inhibitor pharmacologically activates p53 and induces apoptosis in human melanoma cells. Cancer Res 2007;67:209-17
18. Johnson TR, Mann BE, Clark JE, et al. Metal carbonyls: a new class of pharmaceuticals? Angew Chem Int Ed 2003;42:3722-9
19. Alberto R, Motterlini R. Chemistry and biological activities of CO-releasing molecules (CORMs) and transition metal complexes. Dalton Trans 2007;17:1651-60
20. Schlawe D, Majdalani A, Velcicky J, et al. Iron-containing nucleoside analogues with pronounced apoptosis-inducing activity. Angew Chem Int Ed Engl 2004;43:1731-4
21. Greenfield H, Sternberg HW, Friedel RA, et al. Acetylenic dicobalt hexacarbonyls. Organometallic compounds derived from alkynes and dicobalt octacarbonyl. J Am Chem Soc 1956;78:120-4
22. Green JR. Chemistry of propargyldicobalt cations: recent developments in the Nicholas and related reactions. Curr Org Chem 2001;5:809-26
23. 2Me(II) (292 K) and R=But(III) (200 K). Acta Cryst 1983;C39:1024-7
24. Schmidt K, Jung M, Keilitz R, et al. Acetylenehexcarbonyldicobalt complexes, a novel class of antitumor drugs. Inorg Chim Acta 2000;306:6-16
25. Omae I. Three characteristic reactions of organocobalt compounds in organic synthesis. Appl Organomet Chem 2007;21:318-44
26. Hyama T, Nishide K, Saimoto H, et al. Chem Abstr 1987;107:229145b
27. Jung M, Kerr DE, Senter PD. Bioorganometallic chemistry: synthesis and antitumor activity of cobalt carbonyl complexes. Arch Pharm 1997;330(6):173-6
28. Roth T, Eckert C, Fiebig HH, et al. Comparative action of cobalt carbonyl complexes on cancer cells using human tumor xenografts. Anticancer Res 2002;22(4):2281-4
29. Ott I, Kircher B, Gust R. Investigations on the effects of cobalt-alkyne complexes on leukemia and lymphoma cells: cytotoxicity and cellular uptake. J Inorg Biochem 2004;98:485-9
30. Ott I, Schmidt K, Kircher B, et al. Antitumor-active cabalt-alkyne complexes derived from acetylsalicylic acid: studies on the mode of drug action. J Med Chem 2005;48:622-9
31. Ott I, Koch T, Shorafa H, et al. Synthesis, cytotoxicity, cellular uptake and influence on eicosanoid metabolism of cobalt-alkyne modified fructoses in comparison to auranofin and the cytotoxic COX-inhibitor Co-ASS. Org Biomol Chem 2005;3:2282-6
32. Ott I, Abraham A, Schumacher P, et al. Synergistic and additive antiproliferative effects on human leukemia cell lines induced by combining acetylenehexacarbonyl dicobalt complexes with the tyrosine kinase inhibitor imatinib. J Inorg Biochem 2006;100:1903-6
33. Sergeant CD, Ott I, Sniady A, et al. Metallo-nucleosides: synthesis and biological evaluation of hexacarbonyl dicobalt 5-alkynyl-2′-deoxyuridines. Org Biomol Chem 2008;6:73-80
34. Ulrich CM, Bigler J, Potter JD, et al. Non-steroidal anti-inflammatory drugs for cancer prevention: promise, perils and pharmacogenetics. Nat Rev Cancer 2006;6:130-40
35. Ott I, Gust R. Stability, protein binding and thiol interaction studies on [2-acetoxy-(2-propynyl)benzoate]-hexacarbonyl dicobalt. Biometals 2005;18:171-7
36. Etheve-Quelquejieu M, Tranchier J-P, Rose-Munch F, et al. η6-(Arene) tricarbonylchromium and manganese complexes linked to 2′-deoxyuridine. Organometallics 2007;26:5727-30
37. Neukamm MA, Pinto A, Metzler-Nolte N. Synthesis and cytotoxicity of a cobaltcarbonyl-alkyne enkephalin bioconjugate. Chem Commun 2008;232-4
38. Jaouen G, Vessieres A, Top S, et al. Metal carbonyl fragments as a new class of markers in molecular biology. J Am Chem Soc 1985;107:4778-80
39. Salmain M, Vessieres A, Jaouen G, et al. Fourier transform infrared spectroscopic method for the quantitative trace analysis of transition metal carbonyl-labeled bioloigands. Anal Chem 1991;63:2323-9
40. Metzler-Nolte N. Labeling of biomolecules for medicinal applications: bioorganometallic chemistry at its best. Angew Chem Int Ed Engl 2001;40(6):1040-3
41. Philomin V, Vessieres A, Jaouen G. New applications of carbonylmetalloimmunoassay (CMIA): a nonradioisotopic approach to cortisol assay. J Immunol Methods 1994;171:201-10
42. Philomin V, Vessieres A. Gruselle M, et al. Synthesis of cobalt carbonyl complexes of cortisol and testosterone. Study of their recognition by specific polyclonal antibodies. Bioconjug Chem 1993;4(6):419-24
43. Salmain M, Vessieres A. Butler IS, et al. (N-Succinimidyl-4-pentynoate) hexacarbonyl dicobalt: a transition metal carbonyl complex having similar uses to the Bolton-Hunter reagent. Bioconjug Chem 1991;2:13-5
44. Varenne A, Vessieres A, Salmain M, et al. Production of specific antibodies and development of a non-isotopic immunoasaay for carbamazepine by carbonyl metallo-immunoassay (CMIA) method. J Immunol Methods 1995;186(2):195-204
45. Varenne A, Vessieres A, Salmain M, et al. Quantitative analysis of mixtures of metal-carbonyl complexes by Fourier transform infrared spectroscopy: application to the simultaneous double immunoassay of antiepileptic drugs by the noisotopic carbonyl metalloimmunoassay method. Anal Biochem 1996;242(2):172-9
46. Salmain M, Vessieres A, Varenne A, et al. A new application of bioorganometallics: the first simultaneous triple assay by the carbonylmetalloimmunoaasay (CMIA) method. J Organomet Chem 1999;589(1):92-7
47. Vessieres A, Salmain M, Brossier P, et al. Carbonylmetalloimmunoassay: a new application for Fourier transform infrared spectroscopy. J Pharm Biomed Anal 1999;21(3):625-33
48. Vasenne A, Salmain M, Brisson C, et al. Transition metal carbonyl labeling of proteins. A novel approach to a solid-phase two-site immunoassay using Fourier transform infrared spectroscopy. Bioconjug Chem 1992;3:471-6
49. Salmain M, Fischer-Durand N, Cavalier L, et al. Transition metal carbonyl labeling of biotin and avidin for use in solid-phase carbonyl metallo immunoassay. Bioconjug Chem 2002;13(3):693-8
50. Vessieres A, Top S, Vaillant C, et al. Estradiols modified by metal carbonyl clusters as suicide substrates for the study of receptor proteins: application to the estradiol receptor. Angew Chem Int Ed Engl 1992;31(6):753-5
51. Osella D, Galeotti F, Cavigioloi G, et al. The hexacarbonyl(ethyne)dicobalt unit: an androgen tag. Helvetica Chim Acta 2002;85:2918-25
52. Top S, El Hafa H, Vessieres A, et al. Novel estradiol derivatives labeled with Ru, W and Co complexes. Influence on hormone-receptor affinity of several organometallic groups at the 17α-position. Chem Eur J 2002;8(22):5241-9
53. Biotesys gmbh. Enzyme-linked immunoassay kit for identifying oxidized biomacromolecules, useful for early diagnosis of e.g. neurodegenerative disease, uses antibodies against dinitrophenylhydrazine for detecting carbonyl compounds. FR2856798 (2004)
54. Ire Celltarg SA. Affinity markers for hormonal steroid receptors, their use in hormonoradio therapy and as imaging agents of hormone-dependent cancers. EP345153 (1989)
55. Centre Nat Rech Scient. Organometallic complexes of estrogens and their application to the determination of hormone receptors. US4983646 (1991)
56. Centre Nat Rech Scient. Organometallic complexes of estrogens and their application to the determination of hormone receptors. US4656142 (1987)
57. Centre Nat Rech Scient. Organometallic complexes of estrogens and their use in the determination of hormone receptors. EP0105785 (1984)
58. Centre Nat Rech Scient. Organic metal complex of estrogen and application to hormone receptor determination. JP59080695 (1984)
59. Centre Nat Rech Scient. Organometallic complexes of estrogens and their use in the determination of hormone receptors. FR2533570 (1984)
60. Centre Nat Rech Scient. Organometallische Komplexe von Oestrogenen und ihre Anwendung fuer die Bestimmung von Hormonrezeptoren. AT32727T (1988)
61. Organometallic complexes of estrogens and use for the assay of hormone receptors. CA1234037 (1988)
62. Centre Nat Rech Scient. Organometallic oestrogen complexes and their use in the assay of the hormonal receptors. CA1220469 (1987)
63. Roussel Uclaf. Organometallic complexes of steroidal products with an affinity for progestogen and glucocorticoid receptors and their application to the assay of hormone receptors. FR2592047 (1987)
64. Centre Nat Rech Scient. Infrared immunological dosing. WO8807684 (1988)
65. Centre Nat Rech Scient. Dosage immunologique infrarouge. FR2613490 (1988)
66. Centre Nat Rech Scient. Infrared immunological dosing. EP308473 (1989)
67. Centre Nat Rech Scient. Cold marking of molecules of peptidic or proteinic nature. WO8910372 (1989)
68. Centre Nat Rech Scient. Marquage froid de molecules de nature peptidique ou proteique. FR2630547 (1989)
69. Centre Nat Rech Scient. Cold marking of molecules of peptidic or proteinic nature. EP412104 (1991)
70. Centre Nat Rech Scient. New types of cold bioprobes comprising a cluster of alcyne-carbonyle metal. WO8805439 (1988)
71. Centre Nat Rech Scient. New types of cold bioprobes comprising a cluster of alcyne-carbonyle metal. FR2610113 (1988)
72. Centre Nat Rech Scient. New types of cold bioprobes comprising a cluster of alcyne-carbonyle metal. EP299045 (1989)
73. JP01502663
74. Centre Nat Rech Scient. Cold marking of molecules of peptidic or proteinic nature. WO8910372 (1989)
75. Centre Nat Rech Scient. Marquage froid de molecules de nature peptidique ou proteique. FR2630547 (1989)
76. Debreczeni JE, Bullock AN, Atilla GE, et al. Ruthenium half-sandwich complexes bound to the protein kinase Pim-1. Angew Chem Int Ed 2006;45:1580-5