Metabolic and electrochemical mechanisms of dimeric naphthoquinones cytotoxicity in breast cancer cells

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 23, 2011, Pages 7057-7062

  Emadi, Ashkan ^a,c   Le, Anne ^a   Harwood, Cynthia J ^b   Stagliano, Kenneth W ^c   Kamangar, Farin ^d   Ross, Ashley E ^a   Cooper, Charles R ^a   Dang, Chi V ^a   Karp, Judith E ^a   Vuica Ross, Milena ^a  

^a JOHNS HOPKINS UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b PURDUE UNIVERSITY   (United States)

^c Illinois Institute of Technology   (United States)

^d MORGAN STATE UNIVERSITY   (United States)

Author keywords

Anticancer agents; Cytotoxicity; Dimeric naphthoquinones; Oxidative stress; Tumor metabolism

Indexed keywords

1,4 NAPHTHOQUINONE DERIVATIVE; ADENOSINE TRIPHOSPHATE; DIMER; OXYGEN; REACTIVE OXYGEN METABOLITE;

ARTICLE; BREAST CANCER; CANCER CELL; CELL STRAIN MCF 7; CELL STRAIN MDA 453; CONTROLLED STUDY; CYCLIC POTENTIOMETRY; DRUG CYTOTOXICITY; DRUG STRUCTURE; ELECTROCHEMICAL ANALYSIS; GROWTH INHIBITION; IC 50; MITOCHONDRIAL RESPIRATION; OXIDATION REDUCTION REACTION; OXIDATIVE PHOSPHORYLATION; OXIDATIVE STRESS; OXYGEN CONSUMPTION; SEMI EMPIRICAL MOLECULAR ORBITAL CALCULATION;

BREAST NEOPLASMS; CELL GROWTH PROCESSES; CELL LINE, TUMOR; FEMALE; HUMANS; NAPHTHOQUINONES; OXIDATIVE STRESS; REACTIVE OXYGEN SPECIES;

EID: 80655132881     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.10.005     Document Type: Article

References (30)

1. A. Jemal, R. Siegel, J. Xu, and E. Ward CA Cancer J. Clin. 60 2008 277
2. K.W. Stagliano, A. Emadi, Z. Lu, H.C. Malinakova, B. Twenter, M. Yu, L.E. Holland, A.M. Rom, J.S. Harwood, R. Amin, A.A. Johnson, and Y. Pommier Bioorg. Med. Chem. 14 2006 5651
3. A.E. Ross, A. Emadi, L. Marchionni, P.J. Hurley, B.W. Simons, E.M. Schaeffer, and M. Vuica-Ross BJU Int. 108 2011 447
4. A. Emadi, A.E. Ross, K.M. Cowan, Y.M. Fortenberry, and M. Vuica-Ross PLoS One 5 2010 e10846
5. C.V. Dang Mol. Cell Biol. 30 2010 1300
6. W.H. Koppenol, P.L. Bounds, and C.V. Dang Nat. Rev. Cancer 11 2011 325
7. S. Mazurek, A. Michel, and E. Eigenbrodt J. Biol. Chem. 272 1997 4941
8. A. Emadi, J.S. Harwood, S. Kohanim, and K.W. Stagliano Org. Lett. 4 2002 521
9. I.T. Crosby, M.L. Rose, M.P. Collis, P.J. de Bruyn, P.L.C. Keep, and A.D. Robertson Australian J. Chem. 61 2008 768
10. I.T. Crosby, D.G. Bourke, E.D. Jones, P.J. de Bruyn, D. Rhodes, N. Vandegraaff, S. Cox, J.A. Coates, and A.D. Robertson Bioorg. Med. Chem. 18 2010 6442
11. A. Le, C.R. Cooper, A.M. Gouw, R. Dinavahi, A. Maitra, L.M. Deck, R.E. Royer, D.L. Vander Jagt, G.L. Semenza, and C.V. Dang Proc. Natl. Acad. Sci. U.S.A. 107 2010 2037
12. H.N. Kung, J.R. Marks, and J.T. Chi PLoS Genet. 7 2011 e1002229
13. J. Koyama, I. Morita, N. Kobayashi, T. Osakai, H. Hotta, J. Takayasu, H. Nishino, and H. Tokuda Cancer Lett. 201 2003 25
14. J. Koyama, I. Morita, N. Kobayashi, T. Osakai, H. Hotta, J. Takayasu, H. Nishino, and H. Tokuda Cancer Lett. 212 2004 1
15. J. Koyama, I. Morita, N. Kobayashi, T. Osakai, H. Nishino, and H. Tokuda Cancer Lett. 225 2005 193
16. S.S. Pan, and H. Gonzalez Mol. Pharmacol. 37 1990 966
17. H.Q. Wu, Z.S. Huang, X.Z. Bu, Y.D. Shen, Z.L. Zhang, B.F. Xie, Z.C. Liu, L.Q. Gu, and A.S. Chan Eur. J. Med. Chem. 40 2005 1341
18. N.A. El Maali, and H. Berg Electroanalysis 8 1996 808
19. M. Aguilar-Martinez, N.A. Macias-Ruvalcaba, J.A. Bautista-Martinez, M. Gomez, F.J. Gonzalez, and I. Gonzale Curr. Org. Chem. 8 2004 1721
20. P.W. Crawford, E. Carlos, J.C. Ellegood, C.C. Cheng, Q. Dong, D.F. Liu, and Y.L. Luo Electrochimica 41 1996 2399
21. P.H. Rieger Electrochemistry 1994 Chapman and Hall New York
22. V. Stefanou, D. Matiadis, G. Melagraki, A. Afantitis, G. Athanasellis, O. Igglessi-Markopoulou, V. McKee, and J. Markopoulos Molecules 16 2011 384
23. R. Benigni Chem. Rev. 105 2005 1767
24. G. Cavelier, and L.M. Amzel Proteins Struct. Funct. Genet. 43 2001 420
25. Emadi, A. Department of Biological, Chemical and Physical Sciences, Illinois Institute of Technology 2004, PhD.
26. T. Mosmann J. Immunol. Methods 65 1983 55
27. A.J. Cunningham, and A.L. Underwood Biochemistry 6 1967 266
28. P.A.L. Ferraz, F.C. de Abreu, A.V. Pinto, V. Glezer, J. Tonholo, and M.O.F. Goulart J. Electroanal. Chem. 507 2001 275
29. J.J.P. Stewart J. Comp. Chem. 10 1989 221
30. Gaussian03; Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery Jr, J. A.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. 2004.