Aminoferrocene-based prodrugs activated by reactive oxygen species

Journal of Medicinal Chemistry

Volumn 55, Issue 2, 2012, Pages 924-934

  Hagen, Helen ^a   Marzenell, Paul ^a   Jentzsch, Elmar ^a   Wenz, Frederik ^b   Veldwijk, Marlon R ^b   Mokhir, Andriy ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

^b University Medicine Mannheim   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

4 [(FERROCENYLAMINOCARBONYL)OXYMETHYL] 2 MEHYLPHENYLBORONIC ACID PINACOL ESTER; 4 [[[(FERROCENYLAMINO)CARBONYL]OXY]METHYL] 2 FLUOROPHENYLBORONIC ACID PINACOL ESTER; 4 [[[(FERROCENYLAMINO)CARBONYL]OXY]METHYL]PHENYLBORONIC ACID PINACOL ESTER; 4 [[[(N BENZYL N FERROCENYLAMINO)CARBONYL]OXY]METHYL] 2 PHENYLBORONIC ACID PINACOL ESTER; 4 [[[(N ETHYL N FERROCENYLAMINO)CARBONYL]OXY]METHYL] 2 PHENYLBORONIC ACID PINACOL ESTER; ANTINEOPLASTIC AGENT; FERROCENE DERIVATIVE; FERROUS ION; HYDROGEN PEROXIDE; HYDROXYL RADICAL; PRODRUG; REACTIVE OXYGEN METABOLITE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; ASTROCYTOMA CELL; CANCER CELL CULTURE; CANCER CELL DESTRUCTION; CATALYSIS; CELL MEMBRANE PERMEABILITY; CELL STRAIN HL 60; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYTOTOXICITY; DRUG DECOMPOSITION; DRUG EFFICACY; DRUG SYNTHESIS; FIBROBLAST; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; IRON KINETICS; OXIDATIVE STRESS;

ANTINEOPLASTIC AGENTS; BORONIC ACIDS; CELL ADHESION; CELL LINE, TUMOR; CELL MEMBRANE PERMEABILITY; CELL SURVIVAL; COORDINATION COMPLEXES; DRUG SCREENING ASSAYS, ANTITUMOR; FERROUS COMPOUNDS; HUMANS; HYDROGEN PEROXIDE; HYDROXYL RADICAL; INDOLEQUINONES; IRON; MATRIX METALLOPROTEINASE INHIBITORS; OXIDATIVE STRESS; PRODRUGS; REACTIVE OXYGEN SPECIES; STRUCTURE-ACTIVITY RELATIONSHIP; TUMOR MICROENVIRONMENT;

EID: 84856400292     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm2014937     Document Type: Article

References (45)

1. Jung, Y.; Lippard, S. J. Direct cellular responses to platinum-induced DNA damage Chem. Rev. 2007, 107, 1387-1407 (Pubitemid 46864967)
2. Galmarini, C. M.; Mackey, J. R.; Dumontet, G. Nucleoside analogues and nucleobases in cancer treatment Lancet Oncol. 2002, 3, 415-424 (Pubitemid 36958272)
3. Halliwell, B. Oxidative stress and cancer: have we moved forward? Biochem. J. 2007, 401, 1-11 (Pubitemid 46115897)
4. Engel, R. H.; Evens, A. M. Oxidative stress and apoptosis: a new treatment paradigm in cancer Front. Biosci. 2006, 11, 300-312 (Pubitemid 43253493)
5. Finkel, T. Oxidant signals and oxidative stress Curr. Opin. Cell Biol. 2003, 15, 247-254 (Pubitemid 36332201)
6. Schumacker, P. T. Reactive oxygen species in cancer cells: live by the sword, die by the sword Cancer Cell 2006, 10, 175-176 (Pubitemid 44311072)
7. 2 gradients across biomembranes FEBS Lett. 2000, 475, 121-126 (Pubitemid 30365063)
8. Szatrowski, T. P.; Nathan, C. F. Production of large amounts of hydrogen peroxide by human tumor cells Cancer Res. 1991, 51, 794-798
9. O'Donnell-Tormey, J.; DeBoer, C. J.; Nathan, C. F. Resistance of human tumor cells in vitro to oxidative cytolysis J. Clin. Invest. 1985, 76, 80-86 (Pubitemid 15240420)
10. Stone, J. R. An assessment of proposed mechanisms for sensing hydrogen peroxide in mammalian systems Arch. Biochem. Biophys. 2004, 422, 119-124 (Pubitemid 38169357)
11. Davison, K.; Mann, K. K.; Miller, W. H. Arsenic trioxide: mechanisms of action Semin. Hematol. 2002, 39 (Suppl. I) 3-7
12. Dorr, R. T.; Liddil, J. D.; Soble, M. J. Cytotoxic effects of glutathione-synthesis inhibition by L-buthionine-(S,R)-sulfoximine on human and murine tumor cells Invest. New Drugs 1986, 4, 305-313 (Pubitemid 17047198)
13. Renschler, M. F. The emerging role of reactive oxygen species in cancer therapy Eur. J. Cancer 2004, 40, 1934-1940 (Pubitemid 39094687)
14. Trachootham, D.; Zhou, Y.; Zhang, H.; Demizu, Y.; Chen, Z.; Pelicano, H.; Chiao, P. J.; Achanta, G.; Arlinghaus, R. B.; Liu, J.; Huang, P. Selective killing of oncogenically transformed cells through a ROS-mediated mechanism by β-phenylethyl isothiocyanate Cancer Cell 2006, 10, 241-252 (Pubitemid 44311067)
15. Hulsman, N.; Medema, J. P.; Bos, C.; Jongejan, A.; Leurs, R.; Smit, M. J.; de Esch, I. J. P.; Richel, D.; Wijtmans, M. Chemical insights in the concept of hybrid drugs: the antitumor effect of nitric oxide-donating aspirin involves a quinone methide but not nitric oxide nor aspirin J. Med. Chem. 2007, 50, 2424-2431 (Pubitemid 46799254)
16. Magda, D.; Lepp, C.; Gerasimchuk, N. N.; Lee, I.; Sessler, J. L.; Lin, A.; Bioglow, J. E.; Miller, R. A. Redox cycling by motexafin gadolinium enhances cellular response to ionizing radiation by forming reactive oxygen species Int. J. Radiat. Oncol., Biol., Phys. 2001, 51, 1025-1036 (Pubitemid 33026434)
17. Köpf-Maier, P.; Köpf, H.; Neuse, E. W. J. Ferricenium complexes: a new type of water-soluble antitumor agent Cancer Res. Clin. Oncol. 1984, 108, 336-340 (Pubitemid 15211814)
18. Köpf-Maier, P.; Köpf, H. Non-platinum group metal antitumor agents. History, current status, and perspectives Chem. Rev. 1987, 1137-1152
19. van Staveren, D. R.; Metzler-Nolte, N. Bioorganometallic chemistry of ferrocene Chem. Rev. 2004, 104, 5931-5985 (Pubitemid 40034049)
20. Dougan, S. J.; Habtemariam, A.; McHale, S. E.; Parsons, S.; Sadler, P. J. Catalytic organometallic anticancer complexes Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 11628-11633
21. Totter, J. R. Spontaneous cancer and its possible relationship to oxygen metabolism Proc. Natl. Acad. Sci. U.S.A. 1980, 77, 1763-1767 (Pubitemid 10089551)
22. Beckman, K. B.; Ames, B. N. Oxidative decay of DNA J. Biol. Chem. 1997, 272, 19633-19636 (Pubitemid 27340047)
23. Hamels, D.; Dansette, P. M.; Hillard, E. A.; Top, S.; Vessieres, A.; Herson, P.; Jaouen, G.; Mansuy, D. Ferrocenyl quinone methides as strong antiproliferative agents: formation by metabolic and chemical oxidation of ferrocenyl phenols Angew. Chem., Int. Ed. 2009, 48, 9124-9126
24. Jaouen, G.; Top, S.; Vessieres, A. Organometallics targeted to specific biological sites: the development of new therapies. In Bioorganometallics; Jaouen, G., Ed.; Wiley-VCH: Weinheim, Germany, 2006; p 65.
25. Hillard, E. A.; Vessieres, A.; Thouin, L.; Jaouen, G.; Amatore, C. Ferrocene-mediated proton-coupled electron transfer in a series of ferrocifen-type breast-cancer drug candidates Angew. Chem., Int. Ed. 2006, 45, 285-290 (Pubitemid 43017528)
26. (a) Khosrow, K.; Rigas, B. The mechanism of action of nitric oxide-donating aspirin Biochem. Biophys. Res. Commun. 2007, 358, 1096-1101 (Pubitemid 46829001)
27. Wlassoff, W. A.; Albright, C. D.; Sivashinski, M. S.; Ivanova, A.; Appelbaum, J. G.; Salganik, R. I. Hydrogen peroxide overproduced in breast cancer cells can serve as an anticancer prodrug generating apoptosis-stimulating hydroxyl radicals under the effect of tamoxifen-ferrocene conjugate J. Pharm. Pharmacol. 2007, 59, 1549-1553 (Pubitemid 350057459)
28. Pigeon, P.; Top, S.; Vessières, A.; Huchè, M.; Görmen, M.; El Arbi, M.; Plamont, M.-A.; McGlinchey, M. J.; Jaouen, G. A new series of ferrocifen derivatives, bearing two aminoalkyl chains, with strong antiproliferative effects on breast cancer cells New J. Chem. 2011, 35, 2212-2218
29. Charkoudian, L. K.; Pham, D. M.; Franz, K. J. A pro-chelator triggered by hydrogen peroxide inhibits iron-promoted hydroxyl radical formation J. Am. Chem. Soc. 2006, 128, 12424-12425 (Pubitemid 44476626)
30. Wei, Y.; Guo, M. Hydrogen peroxide triggered prochelator activation, subsequent metal chelation, and attenuation of the Fenton reaction Angew. Chem., Int. Ed. 2007, 46, 4722-4725 (Pubitemid 46997471)
31. Major Jourden, J. L.; Cohen, S. M. Hydrogen peroxide activated matrix metalloproteinase inhibitors: a prodrug approach Angew. Chem., Int. Ed. 2010, 49, 6795-6797
32. Folk, D. S.; Franz, K. J. A prochelator activated by β-secretase inhibits Aβ aggregation and suppresses copper-induced reactive oxygen species formation J. Am. Chem. Soc. 2010, 132, 4994-4995
33. Schugar, H.; Green, D. E.; Bowen, M. L.; Scott, L. E.; Storr, T.; Bohmerle, K.; Thomas, F.; Allen, D. D.; Lockman, P. R.; Merkel, M.; Thompson, K. H.; Orvig, C. Combating Alzheimer's disease with multifunctional molecules designed for metal passivation Angew. Chem., Int. Ed. 2007, 46, 1716-1718 (Pubitemid 46991786)
34. McDonnell, S. O.; Hall, M. J.; Allen, L. T.; Byrne, A.; Gallagher, W. M.; O'Shea, D. F. Supramolecular photonic therapeutic agents J. Am. Chem. Soc. 2005, 127, 16360-16361 (Pubitemid 41740363)
35. Goldstein, S.; Meyerstein, D.; Czapski, G. The Fenton reagents Free Radical Biol. Med. 1993, 15, 435-445 (Pubitemid 23283560)
36. Trachootham, D.; Alexandre, J.; Huang, P. Targeting cancer cells by ROS-mediated mechanisms: a radical therapeutic approach? Nat. Rev. Drug Discovery 2009, 8, 579-591
37. Zheng, N.; Armstrong, J. D.; Eng, K. K.; Keller, J.; Liu, T.; Purick, R.; Lynch, J.; Hartner, F. W.; Volante, R. P. A convergent asymmetric synthesis of a growth hormone secretagogue Tetrahedron: Asymmetry 2003, 14, 3435-3446 (Pubitemid 37412466)
38. Heinze, K.; Schlenker, M. Main chain ferrocenyl amides from 1-amino-1′-carboxyferrocene Eur. J. Inorg. Chem. 2004, 2974-2988
39. Knox, G. R.; Pauson, P. L. 903. Ferrocene derivatives. Part XI. Azoferrocenes J. Chem. Soc. 1961, 4615-4618
40. The IUPAC Stability Constants Database; SCQuery Vn 4.06/4.045, Academic Software: Sourby Old Farm, Timble, Otley, Yorks, LS21 2PW, UK.
41. Britton, W. E.; Kashyap, R.; El-Hashash, M.; El-Kady, M. The anomalous electrochemistry of the ferrocenylamines Organometallics 1986, 5, 1029-1031
42. Sohn, Y. S.; Hendrickson, D. N.; Grey, H. B. Electronic structure of metallocenes J. Am. Chem. Soc. 1971, 93, 3603-3612
43. Dutta, S.; Mokhir, A. An autocatalytic, chromogenic and fluorogenic photochemical reaction controlled by nucleic acids Chem. Commun. 2011, 47 (4) 1243-1245
44. Wimmer, M. A.; Goldbach, H. E. A miniaturized curcumin method for the determination of boron in solutions and biological samples J. Plant Nutr. Soil Sci. 1999, 162, 15-18 (Pubitemid 129712726)
45. Ma, Y.; Liu, Z.; Hider, R. C; Petrat, F. Determination of the labile iron pool of human lymphocytes using the fluorescent probe, CP655 Anal. Chem. Insights 2007, 2, 61-67