The Potent Inhibitory Effect of a Naproxen-Appended Cobalt(III)-Cyclam Complex on Cancer Stem Cells

ChemBioChem

Volumn 17, Issue 18, 2016, Pages 1713-1718

  Cressey, Paul B ^a   Eskandari, Arvin ^a   Bruno, Peter M ^b   Lu, Chunxin ^a   Hemann, Michael T ^b   Suntharalingam, Kogularamanan ^a  

^a KING'S COLLEGE LONDON   (United Kingdom)

^b MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

antitumour agents; bioinorganic chemistry; cancer; cobalt; cox inhibition

Indexed keywords

CISPLATIN; COBALT COMPLEX; CYCLAM DERIVATIVE; CYCLOOXYGENASE 2; NAPROXEN; NAVELBINE; PACLITAXEL; SALINOMYCIN; ANTINEOPLASTIC AGENT; COBALT; CYCLOOXYGENASE 2 INHIBITOR; ORGANOMETALLIC COMPOUND;

ARTICLE; CANCER STEM CELL; CELL VIABILITY; CONTROLLED STUDY; CYTOTOXICITY; DNA DAMAGE; DRUG EFFECT; DRUG POTENCY; ENZYME INHIBITION; HUMAN; HUMAN CELL; HYPOXIA; IC50; PRIORITY JOURNAL; CELL PROLIFERATION; CHEMISTRY; CONFORMATION; DOSE RESPONSE; DRUG EFFECTS; DRUG SCREENING; METABOLISM; PATHOLOGY; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TUMOR CELL LINE;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL PROLIFERATION; COBALT; CYCLOOXYGENASE 2; CYCLOOXYGENASE 2 INHIBITORS; DNA DAMAGE; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MOLECULAR CONFORMATION; NAPROXEN; NEOPLASTIC STEM CELLS; ORGANOMETALLIC COMPOUNDS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84994638564     PISSN: 14394227     EISSN: 14397633     Source Type: Journal    
DOI: 10.1002/cbic.201600368     Document Type: Article

References (67)

1. L. V. Nguyen, R. Vanner, P. Dirks, C. J. Eaves, Nat. Rev. Cancer 2012, 12, 133–143.
2. D. R. Pattabiraman, R. A. Weinberg, Nat. Rev. Drug Discovery 2014, 13, 497–512.
3. M. Dean, T. Fojo, S. Bates, Nat. Rev. Cancer 2005, 5, 275–284;
4. J. N. Rich, Cancer Res. 2007, 67, 8980–8984.
5. K. Chen, Y.-h. Huang, J.-l. Chen, Acta. Pharmacol. Sin. 2013, 34, 732–740;
6. Y.-x. Feng, E. S. Sokol, C. A. Del Vecchio, S. Sanduja, J. H. L. Claessen, T. A. Proia, D. X. Jin, F. Reinhardt, H. L. Ploegh, Q. Wang, P. B. Gupta, Cancer Discovery 2014, 4, 702–715;
7. R. Lamb, H. Harrison, J. Hulit, D. L. Smith, M. P. Lisanti, F. Sotgia, Oncotarget 2014, 5, 11029–11037.
8. A. Albini, A. Bruno, C. Gallo, G. Pajardi, D. M. Noonan, K. Dallaglio, Connect. Tissue Res. 2015, 56, 414–425;
9. K. Kise, Y. Kinugasa-Katayama, N. Takakura, Adv. Drug Deliv. Rev. 2016, 99B, 197–205.
10. J. M. Heddleston, Z. Li, J. D. Lathia, S. Bao, A. B. Hjelmeland, J. N. Rich, Br. J. Cancer 2010, 102, 789–795;
11. J. M. Heddleston, Z. Li, R. E. McLendon, A. B. Hjelmeland, J. N. Rich, Cell Cycle 2009, 8, 3274–3284;
12. Z. Li, S. Bao, Q. Wu, H. Wang, C. Eyler, S. Sathornsumetee, Q. Shi, Y. Cao, J. Lathia, R. E. McLendon, A. B. Hjelmeland, J. N. Rich, Cancer Cell 2009, 15, 501–513;
13. A. Soeda, M. Park, D. Lee, A. Mintz, A. Androutsellis-Theotokis, R. D. McKay, J. Engh, T. Iwama, T. Kunisada, A. B. Kassam, I. F. Pollack, D. M. Park, Oncogene 2009, 28, 3949–3959;
14. J. Zhang, L. Li, J. Biol. Chem. 2008, 283, 9499–9503.
15. Z. Li, J. N. Rich, Curr. Top. Microbiol. Immunol. 2010, 345, 21–30.
16. K. C. Duggan, M. J. Walters, J. Musee, J. M. Harp, J. R. Kiefer, J. A. Oates, L. J. Marnett, J. Biol. Chem. 2010, 285, 34950–34959;
17. O. Laneuville, D. K. Breuer, D. L. Dewitt, T. Hla, C. D. Funk, W. L. Smith, J. Pharmacol. Exp. Ther. 1994, 271, 927–934.
18. B. Annabi, C. Laflamme, A. Sina, M.-P. Lachambre, R. Béliveau, J. Neuroinflammation 2009, 6, 8;
19. K.-H. Chen, C.-C. Hsu, W.-S. Song, C.-S. Huang, C.-C. Tsai, C.-D. Kuo, H.-S. Hsu, T.-H. Tsai, C.-Y. Tsai, L.-C. Woung, S.-H. Chiou, K.-H. Lu, Y.-W. Chen, Childs Nerv. Syst. 2010, 26, 1605–1612;
20. D. Kanojia, W. Zhou, J. Zhang, C. Jie, P.-K. Lo, Q. Wang, H. Chen, Proteomics 2012, 12, 3407–3415;
21. K. Liao, B. Xia, Q.-Y. Zhuang, M.-J. Hou, Y.-J. Zhang, B. Luo, Y. Qiu, Y.–F. Gao, X.-J. Li, H.-F. Chen, W.-H. Ling, C.-Y. He, Y.-J. Huang, Y.-C. Lin, Z.-N. Lin, Theranostics 2015, 5, 302–321;
22. V. Sharma, D. Dixit, S. Ghosh, E. Sen, Neurochem. Int. 2011, 59, 567–571;
23. B. Singh, K. R. Cook, L. Vincent, C. S. Hall, C. Martin, A. Lucci, J. Surg. Res. 2011, 168, e39–49.
24. J. N. Boodram, I. J. McGregor, P. M. Bruno, P. B. Cressey, M. T. Hemann, K. Suntharalingam, Angew. Chem. Int. Ed. 2016, 55, 2845–2850;
25. Angew. Chem. 2016, 128, 2895–2900;
26. C. M. Moon, J.-H. Kwon, J. S. Kim, S.-H. Oh, K. J. Lee, J. J. Park, S. P. Hong, J. H. Cheon, T. I. Kim, W. H. Kim, Int. J. Cancer 2014, 134, 519–529.
27. K. Yamada in Interrelations between Essential Metal Ions and Human Diseases, Vol. 13 (Eds.: A. Sigel, H. Sigel, R. K. O. Sigel), Springer, Netherlands, 2013, pp. 295–320.
28. M. D. Hall, T. W. Failes, N. Yamamoto, T. W. Hambley, Dalton Trans. 2007, 3983–3990;
29. M. C. Heffern, N. Yamamoto, R. J. Holbrook, A. L. Eckermann, T. J. Meade, Curr. Opin. Chem. Biol. 2013, 17, 189–196;
30. C. R. Munteanu, K. Suntharalingam, Dalton Trans. 2015, 44, 13796–13808.
31. G.-O. Ahn, K. J. Botting, A. V. Patterson, D. C. Ware, M. Tercel, W. R. Wilson, Biochem. Pharmacol. 2006, 71, 1683–1694;
32. P. D. Bonnitcha, B. J. Kim, R. K. Hocking, J. K. Clegg, P. Turner, S. M. Neville, T. W. Hambley, Dalton Trans. 2012, 41, 11293–11304;
33. J. Y.-C. Chang, G.-L. Lu, R. J. Stevenson, P. J. Brothers, G. R. Clark, K. J. Botting, D. M. Ferry, M. Tercel, W. R. Wilson, W. A. Denny, D. C. Ware, Inorg. Chem. 2013, 52, 7688–7698;
34. J. Y.-C. Chang, R. J. Stevenson, G.-L. Lu, P. J. Brothers, G. R. Clark, W. A. Denny, D. C. Ware, Dalton Trans. 2010, 39, 11535–11550;
35. T. W. Failes, C. Cullinane, C. I. Diakos, N. Yamamoto, J. G. Lyons, T. W. Hambley, Chem. Eur. J. 2007, 13, 2974–2982;
36. B. J. Kim, T. W. Hambley, N. S. Bryce, Chem. Sci. 2011, 2, 2135–2142;
37. G.-L. Lu, R. J. Stevenson, J.-Y. Chang, P. J. Brothers, D. C. Ware, W. R. Wilson, W. A. Denny, M. Tercel, Bioorg. Med. Chem. 2011, 19, 4861–4867;
38. J. B. J. Milbank, R. J. Stevenson, D. C. Ware, J. Y. C. Chang, M. Tercel, G.-O. Ahn, W. R. Wilson, W. A. Denny, J. Med. Chem. 2009, 52, 6822–6834;
39. A. K. Renfrew, N. S. Bryce, T. Hambley, Chem. Eur. J. 2015, 21, 15224–15234;
40. A. K. Renfrew, N. S. Bryce, T. W. Hambley, Chem. Sci. 2013, 4, 3731–3739;
41. N. Yamamoto, S. Danos, P. D. Bonnitcha, T. W. Failes, E. J. New, T. W. Hambley, J. Biol. Inorg. Chem. 2008, 13, 861–871;
42. N. Yamamoto, A. K. Renfrew, B. J. Kim, N. S. Bryce, T. W. Hambley, J. Med. Chem. 2012, 55, 11013–11021.
43. M. Ahmad, M. Afzal, S. Tabassum, B. Kalińska, J. Mrozinski, P. K. Bharadwaj, Eur. J. Med. Chem. 2014, 74, 683–693;
44. S. S. Massoud, R. S. Perkins, F. R. Louka, W. Xu, A. Le Roux, Q. Dutercq, R. C. Fischer, F. A. Mautner, M. Handa, Y. Hiraoka, G. L. Kreft, T. Bortolotto, H. Terenzi, Dalton Trans. 2014, 43, 10086–10103;
45. N. Shahabadi, S. Kashanian, F. Darabi, Eur. J. Med. Chem. 2010, 45, 4239–4245;
46. W. Xu, J. A. Craft, P. R. Fontenot, M. Barens, K. D. Knierim, J. H. Albering, F. A. Mautner, S. S. Massoud, Inorg. Chim. Acta 2011, 373, 159–166.
47. C. Angelé-Martínez, C. Goodman, J. Brumaghim, Metallomics 2014, 6, 1358–1381;
48. M. A. Husain, Z. Yaseen, S. U. Rehman, T. Sarwar, M. Tabish, FEBS J. 2013, 280, 6569–6580;
49. S. Roy, S. Roy, S. Saha, R. Majumdar, R. R. Dighe, E. D. Jemmis, A. R. Chakravarty, Dalton Trans. 2011, 40, 1233–1242.
50. P. B. Gupta, T. T. Onder, G. Jiang, K. Tao, C. Kuperwasser, R. A. Weinberg, E. S. Lander, Cell 2009, 138, 645–659.
51. I. Morita, M. Schindler, M. K. Regier, J. C. Otto, T. Hori, D. L. DeWitt, W. L. Smith, J. Biol. Chem. 1995, 270, 10902–10908.
52. G. Dontu, W. M. Abdallah, J. M. Foley, K. W. Jackson, M. F. Clarke, M. J. Kawamura, M. S. Wicha, Genes Dev. 2003, 17, 1253–1270.
53. N. C. Turner, A. N. J. Tutt, Breast Cancer Res. 2012, 14, 115, and references therein.
54. T. Yi, E. Papadopoulos, P. R. Hagner, G. Wagner, J. Biol. Chem. 2013, 288, 18732–18742.
55. H. Jiang, J. R. Pritchard, R. T. Williams, D. A. Lauffenburger, M. T. Hemann, Nat. Chem. Biol. 2011, 7, 92–100;
56. J. R. Pritchard, P. M. Bruno, L. A. Gilbert, K. L. Capron, D. A. Lauffenburger, M. T. Hemann, Proc. Natl. Acad. Sci. USA 2013, 110, E170–E179;
57. J. R. Pritchard, P. M. Bruno, M. T. Hemann, D. A. Lauffenburger, Mol. Biosyst. 2013, 9, 1604–1619.
58. J.-Y. Ahn, J. K. Schwarz, H. Piwnica-Worms, C. E. Canman, Cancer Res. 2000, 60, 5934–5936;
59. S. Burma, B. P. Chen, M. Murphy, A. Kurimasa, D. J. Chen, J. Biol. Chem. 2001, 276, 42462–42467;
60. S. Matsuoka, G. Rotman, A. Ogawa, Y. Shiloh, K. Tamai, S. J. Elledge, Proc. Natl. Acad. Sci. USA 2000, 97, 10389–10394;
61. R. Melchionna, X.-B. Chen, A. Blasina, C. H. McGowan, Nat. Cell Biol. 2000, 2, 762–765;
62. E. P. Rogakou, D. R. Pilch, A. H. Orr, V. S. Ivanova, W. M. Bonner, J. Biol. Chem. 1998, 273, 5858–5868.
63. W. P. Roos, A. D. Thomas, B. Kaina, Nat. Rev. Cancer 2016, 16, 20–33.
64. X.-H. Liu, D. P. Rose, Cancer Res. 1996, 56, 5125–5127;
65. R. A. Soslow, A. J. Dannenberg, D. Rush, B. M. Woerner, K. N. Khan, J. Masferrer, A. T. Koki, Cancer 2000, 89, 2637–2645.
66. A. Nassar, A. Radhakrishnan, I. A. Cabrero, G. Cotsonis, C. Cohen, Appl. Immunohistochem. Mol. Morphol. 2007, 15, 255–259.
67. B. Singh, J. A. Berry, A. Shoher, V. Ramakrishnan, A. Lucci, Int. J. Oncol. 2005, 26, 1393–1399.