Anticancer (hexacarbonyldicobalt)propargyl aryl ethers: Synthesis, antiproliferative activity, apoptosis induction, and effect on cellular oxidative stress

Journal of Inorganic Biochemistry

Volumn 119, Issue , 2013, Pages 28-37

  Schimler, Sydonie D ^a,b   Hall, David J ^a   Debbert, Stefan L ^a  

^a LAWRENCE UNIVERSITY   (United States)

^b UNIVERSITY OF MICHIGAN   (United States)

Author keywords

Organometallic medicinal chemistry; Oxidative stress

Indexed keywords

(HEXACARBONYLDICOBALT) 2 METHYL 3 BUTYN 2 YL 4 NITROPHENYL ETHER; (HEXACARBONYLDICOBALT) 3 BUTYNYL 4 NITROPHENYL ETHER; (HEXACARBONYLDICOBALT) N (4 NITROPHENYL)PROPARGYLAMINE; (HEXACARBONYLDICOBALT)PROPARGYL 4 ANISYL ETHER; (HEXACARBONYLDICOBALT)PROPARGYL 4 BROMOPHENYL ETHER; (HEXACARBONYLDICOBALT)PROPARGYL 4 CHLOROPHENYL ETHER; (HEXACARBONYLDICOBALT)PROPARGYL 4 CYANOPHENYL ETHER; (HEXACARBONYLDICOBALT)PROPARGYL 4 FLUOROPHENYL ETHER; (HEXACARBONYLDICOBALT)PROPARGYL 4 NITROPHENYL ETHER; (HEXACARBONYLDICOBALT)PROPARGYL 4 TOLYL ETHER; (HEXACARBONYLDICOBALT)PROPARGYL PHENYL ETHER; (HEXACARBONYLDICOBALT)PROPARGYL(4 NITROPHENYL)METHYL ETHER; 4 (PROPARGYLOXY)ACETANILIDE; 4 [(HEXACARBONYLDICOBALT)PROPARGYLOXY]ACETANILIDE; ANTINEOPLASTIC AGENT; COBALT DERIVATIVE; ETHYL 4 (PROPARGYLOXY)BENZOATE; ETHYL 4 [(HEXACARBONYLDICOBALT)PROPARGYLOXY]BENZOATE; PROPARGYL 4 ANISYL ETHER; PROPARGYL 4 BROMOPHENYL ETHER; PROPARGYL 4 CHLOROPHENYL ETHER; PROPARGYL 4 CYANOPHENYL ETHER; PROPARGYL 4 FLUOROPHENYL ETHER; PROPARGYL 4 NITROPHENYL ETHER; PROPARGYL 4 TOLYL ETHER; PROPARGYL PHENYL ETHER; UNCLASSIFIED DRUG;

ANTIPROLIFERATIVE ACTIVITY; APOPTOSIS; ARTICLE; CANCER INHIBITION; CONTROLLED STUDY; DRUG SCREENING; DRUG SYNTHESIS; FLOW CYTOMETRY; HUMAN; HUMAN CELL; IC 50; MITOCHONDRIAL PERMEABILITY; OXIDATIVE STRESS; S PHASE CELL CYCLE CHECKPOINT;

ALKYNES; ANTINEOPLASTIC AGENTS; APOPTOSIS; BREAST NEOPLASMS; CELL LINE, TUMOR; CELL MEMBRANE PERMEABILITY; CELL PROLIFERATION; COBALT; ETHERS; FEMALE; FLOW CYTOMETRY; GENTIAN VIOLET; HUMANS; INHIBITORY CONCENTRATION 50; OXIDATIVE STRESS; S PHASE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84869222731     PISSN: 01620134     EISSN: 18733344     Source Type: Journal    
DOI: 10.1016/j.jinorgbio.2012.10.014     Document Type: Article

References (51)

1. G. Jaouen, and N. Metzler-Nolte Medicinal Organometallic Chemistry 2010 Springer Berlin
2. G. Gasser, I. Ott, and N. Metzler-Nolte J. Med. Chem. 54 2011 3 25
3. E. Meggers Curr. Opin. Chem. Biol. 11 2007 287 292
4. S.H. van Rijt, and P.J. Sadler Drug Discov. Today 14 2009 1089 1097
5. M. Hogan, and M. Tacke G. Jaouen, N. Metzler-Nolte, Medicinal Organometallic Chemistry 2010 Springer Berlin 119 140
6. C. Biot, G. Glorian, L.A. Maciejewski, J.S. Brocard, O. Domarle, G. Blampain, P. Millet, A.J. Georges, H. Abessolo, D. Dive, and J. Lebibi J. Med. Chem. 40 1997 3715 3718
7. J.M. Rademaker-Lakhai, D. van den Bongard, D. Pluim, J.H. Beijnen, and J.H. Schellens Clin. Cancer Res. 10 2004 3717 3727
8. M.A. Jakupec, V.B. Arion, S. Kapitza, E. Reisner, A. Eichinger, M. Pongratz, B. Marian, N. Graf von Keyserlingk, and B.K. Keppler Int. J. Clin. Pharmacol. Ther. 43 2005 595 596
9. Y. Fu, A. Habtemariam, A.M. Pizarro, S.H. van Rijt, D.J. Healey, P.A. Cooper, S.D. Shnyder, G.J. Clarkson, and P.J. Sadler J. Med. Chem. 53 2010 8192 8196
10. J.L. Hickey, R.A. Ruhayel, P.J. Barnard, M.V. Baker, S. Berners-Price, and A. Filipovska J. Am. Chem. Soc. 130 2008 12570 12571
11. P.J. Barnard, M.V. Baker, S.J. Berners-Price, and D.A. Day J. Inorg. Biochem. 98 2004 1642 1647
12. K. Schmidt, M. Jung, R. Keilitz, B. Schnurr, and R. Gust Inorg. Chim. Acta 306 2000 6 16
13. M. Jung, D.E. Kerr, and P.D. Senter Arch. Pharm. (Weinheim) 330 1997 173 176
14. I. Ott, K. Schmidt, B. Kircher, P. Schumacher, T. Wiglenda, and R. Gust J. Med. Chem. 48 2005 622 629
15. I. Ott, B. Kircher, C.P. Bagowski, D.H. Vlecken, E.B. Ott, J. Will, K. Bensdorf, W.S. Sheldrick, and R. Gust Angew. Chem. Int. Ed Engl. 48 2009 1160 1163
16. I. Ott, B. Kircher, R. Dembinski, and R. Gust Expert Opin. Ther. Patents 18 2008 327 337
17. F. Dubar, J. Khalife, J. Brocard, D. Dive, and C. Biot Molecules 13 2008 2900 2907
18. E.A. Hilliard, A. Vessiéres, and G. Jaouen G. Jaouen, N. Metzler-Nolte, Medicinal Organometallic Chemistry 2010 Springer Berlin 81 117
19. M. Pal, K. Parasuraman, and K.R. Yeleswarapu Org. Lett. 5 2003 349 352
20. Q. Chen, Y. Cui, T. Zhang, J. Cao, and B. Han Biomacromolecules 11 2010 13 19
21. BioDataFit, Chang BioScience http://www.changbioscience.com/stat/ec50. html (accessed May 31, 2012)
22. B.M. Trost, and B.L. Ashfeld Org. Lett. 10 2008 1893 1896
23. O. Yamada, H. Matsumoto, T. Shimizu, United States Patent 2006/0041031 (2003).
24. D.J. McNamara, E.M. Berman, D.W. Fry, and L.M. Werbel J. Med. Chem. 33 1990 2045 2051
25. R.F. Lockwood, and K.M. Nicholas Tetrahedron Lett. 18 1977 4163 4165
26. B.J. Teobald Tetrahedron 58 2002 4133 4170
27. A.J. Atkin, S. Williams, P. Sawle, R. Motterlini, J.M. Lynam, and I.J.S. Fairlamb Dalton Trans. 2009 3653 3656
28. J.A. Bailey J. Chem. Educ. 88 2011 995 998
29. N. Zamzami, and G. Kroemer Curr. Biol. 13 2003 R71 R73
30. T. Ozben J. Pharm. Sci. 96 2007 2181 2196
31. S. Reuter, S.C. Gupta, M.M. Chaturvedi, and B.B. Aggarwal Free Radic. Biol. Med. 49 2010 1603 1616
32. S. Leonard, P.M. Gannett, Y. Rojanasakul, D. Schwegler-Berry, V. Castranova, V. Vallyathan, and X. Shi J. Inorg. Biochem. 70 1998 239 244
33. A. Gomes, E. Fernandes, J.L. Lima, and J. Biochem Biophys. Methods 65 2005 45 80
34. X. Chen, Z. Zhong, Z. Xu, L. Chen, and Y. Wang Free Radic. Res. 44 2010 587 604
35. G. Kroemer Curr. Med. Chem. 10 2003 1469 1472
36. G. Kroemer, L. Galluzzi, and C. Brenner Physiol. Rev. 87 2007 99 163
37. L. Galluzzi, N. Larochette, N. Zamzami, and G. Kroemer Oncogene 25 2006 4812 4830
38. G. Edsall N. Engl. J. Med. 211 1934 385 390
39. L. Galluzzi, N. Zamzami, T. de La Motte Rouge, C. Lemaire, C. Brenner, and G. Kroemer Apoptosis 12 2007 803 813
40. T.R. Johnson, B.E. Mann, J.E. Clark, R. Foresti, C.J. Green, and R. Motterlini Angew. Chem. Int. Ed Engl. 42 2003 3722 3729
41. R. Motterlini, J.E. Clark, R. Foresti, P. Sarathchandra, B.E. Mann, and C.J. Green Circ. Res. 90 2002 E17 E24
42. R. Motterlini, and L.E. Otterbein Nat. Rev. Drug Discov. 9 2010 728 743
43. C. Peers, and D.S. Steele J. Mol. Cell. Cardiol. 52 2012 359 365
44. M. Karlsson, T. Kurz, U.T. Brunk, S.E. Nilsson, and C.I. Frennesson Biochem. J. 428 2010 183 190
45. C. Biot, D. Taramelli, I. Forfar-Bares, L.A. Maciejewski, M. Boyce, G. Nowogrocki, J.S. Brocard, N. Basilico, P. Olliaro, and T.J. Egan Mol. Pharm. 2 2005 185 193
46. C. Biot, and D. Dive G. Jaouen, N. Metzler-Nolte, Bioorganic Chemistry and Malaria Medicinal Organometallic Chemistry vol. 32 2010 Springer Berlin 155 193
47. A. Nguyen, A. Vessières, E.A. Hillard, S. Top, P. Pigeon, and G. Jaouen Chim. Int. J. Chem. 61 2007 716 724
48. D. Osella, H. Mahboobi, D. Colangelo, G. Cavigiolio, A. Vessières, and G. Jaouen Inorg. Chim. Acta 358 2005 1993 1998
49. J.R. Kirshner, S. He, V. Balasubramanyam, J. Kepros, C.Y. Yang, M. Zhang, Z. Du, J. Barsoum, and J. Bertin Mol. Cancer Ther. 7 2008 2319 2327
50. K.J. Coe, Y. Jia, H.K. Ho, P. Rademacher, T.K. Bammler, R.P. Beyer, F.M. Farin, L. Woodke, S.R. Plymate, N. Fausto, and S.D. Nelson Chem. Res. Toxicol. 20 2007 1277 1290
51. I. Ott, and R. Gust Biometals 18 2005 171 177