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Metal-based anticancer agents: targeting androgen-dependent and androgen-independent prostate and COX-positive pancreatic cancer cells by phenanthrenequinone semicarbazone and its metal complexes

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Abstract

A planar, polycyclic and aromatic hydrocarbon ligand, namely 9,10-phenanthrenequinone semicarbazone, and its transition metal complexes have been synthesized and structurally characterized. The in vitro antiproliferative activity of these compounds against five human cancer cell lines revealed that they were effective against androgen receptor-positive/negative prostate cancer cells as well as COX-positive pancreatic BxPC-3 cancer cell line. The driving force behind such antiproliferative activity seems to be the up-regulated COX expression in these cells, which was amenable for targeting through metal complexation. These structural motifs can, therefore, serve as a starting point for developing novel cytotoxic agents against the growing number of prostate and pancreatic cancers.

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References

  1. Siegel R, Ward E, Brawley O, Jemal A (2011) CA Cancer J Clin 62:10–29

    Article  Google Scholar 

  2. Pienta K, Bradley D (2006) Clin Cancer Res 12:1665–1671

    Article  CAS  Google Scholar 

  3. Stanway S, Purohit A, Woo L, Sufi S, Vigushin D, Ward R, Wilson R, Stanczyk F, Dobbs N, Kulinskaya E (2006) Clin Cancer Res 12:1585–1592

    Article  CAS  Google Scholar 

  4. Mizokami A, Koh E, Fujita H, Maeda Y, Egawa M, Koshida K, Honma S, Keller E, Namiki M (2004) Cancer Res 64:765–771

    Article  CAS  Google Scholar 

  5. Bracarda S, de Cobelli O, Greco C, Prayer-Galetti T, Valdagni R, Gatta G, de Braud F, Bartsch G (2005) Crit Rev Oncol Hematol 56:379–396

    Article  Google Scholar 

  6. Donovan MJ, Osman I, Khan FM, Vengrenyuk Y, Capodieci P, Koscuiszka M, Anand A, Cordon-Cardo C, Costa J, Scher HI (2010) BJU Int 105:462–467

    Article  CAS  Google Scholar 

  7. O’Neill GP, Ford-Hutchinson AW (1993) FEBS Lett 330:156–160

    Google Scholar 

  8. Gupta S, Srivastava M, Ahmad N, Bostwick DG, Mukhtar H (2000) Prostate 42:73–78

    Article  CAS  Google Scholar 

  9. Yoshimura R, Sano H, Masuda C, Kawamura M, Tsubouchi Y, Chargui J, Yoshimura N, Hla T, Wada S (2000) Cancer 89:589–596

    Article  CAS  Google Scholar 

  10. Madaan S, Abel PD, Chaudhary KS, Hewitt R, Stott MA, Stamp GW, Lalani EN (2000) BJU Int 86:736–741

    Article  CAS  Google Scholar 

  11. Hermanova M, Trna J, Nenutil R, Dite P, Kala Z (2008) Eur J Gastroenterol Hepatol 20:732–739

    Article  CAS  Google Scholar 

  12. Xu L, Li YM, Yu CH, Li L, Liu YS, Zhang BF, Fang J, Zhou Q, Hu Y, Gao HJ (2006) Hepatobiliary Pancreat Dis Int 5:138–142

    CAS  Google Scholar 

  13. Ahmed F, Adsule S, Ali AS, Banerjee S, Ali S, Kulkarni S, Padhye S, Sarkar FH (2007) Int J Cancer 120:734–742

    Article  CAS  Google Scholar 

  14. Sarkar FH, Adsule S, Li Y, Padhye S (2007) Mini Rev Med Chem 7:599–608

    Article  CAS  Google Scholar 

  15. Kovács A, Vasas A, Hohmann J (2008) Phytochemistry 69:1084–1110

    Article  Google Scholar 

  16. Ju JH, Yang JS, Li J, Xiao PG (2000) Chin Chem Lett 11:37–38

    CAS  Google Scholar 

  17. Chen Y, Liu Y, Jiang J, Zhang Y, Yin B (2008) Food Chem 11:111–112

    Google Scholar 

  18. Lee CL, Chang FR, Yen MH, Yu D, Liu YN, Bastow KF, Morris-Natschke SL, Wu YC, Lee KH (2009) J Nat Prod 72:210–213

    Article  CAS  Google Scholar 

  19. Kuo CT, Hsu MJ, Chen BC, Chen CC, Teng CM, Pan SL, Lin CH (2008) Toxicol Lett 177:48–58

    Article  CAS  Google Scholar 

  20. Yang KC, Uen YH, Suk FM, Liang YC, Wang YJ, Ho YS, Li IH, Lin SY (2005) World J Gastroenterol 11:3040–3045

    CAS  Google Scholar 

  21. Chen TH, Pan SL, Guh JH, Chen CC, Huang YT, Pai HC, Teng CM (2008) Naunyn Schmiedebergs Arch Pharmacol 378:447–457

    Article  CAS  Google Scholar 

  22. Sánchez-Duffhues G, Calzado MA, de Vinuesa AG, Appendino G, Fiebich BL, Loock U, Lefarth-Risse A, Krohn K, Muñoz E (2009) Biochem Pharmacol 77:1401–1409

    Article  Google Scholar 

  23. Flowers-Geary L, Bleczinki W, Harvey RG, Penning TM (1996) Chem Biol Interact 99:55–72

    Article  CAS  Google Scholar 

  24. Matsunaga T, Arakaki M, Kamiya T, Haga M, Endo S, El-Kabbani O, Hara A (2010) Toxicology 268:191–197

    Article  CAS  Google Scholar 

  25. Powell AK (1951) Br J Cancer 5:264–272

    Article  CAS  Google Scholar 

  26. Murugkar A, Unnikrishnan B, Padhye S, Bhonde R, Teat S, Triantafillou E, Sinn E (1999) Met Based Drugs 6:177–182

    Article  CAS  Google Scholar 

  27. West DX, Liberta AE, Padhye SB, Chikate RC, Sonawane PB, Kumbhar AS, Yerande RG (1993) Coord Chem Rev 123:49–71

    Article  CAS  Google Scholar 

  28. Padhyé SB, Kauffman GB (1985) Coord Chem Rev 63:127–160

    Article  Google Scholar 

  29. Kalinowski DS, Quach P, Richardson DR (2009) Future Med Chem 1:1143–1151

    Article  CAS  Google Scholar 

  30. Lobana TS, Sharma R, Bawa Ga, Khanna S (2009) Coord Chem Rev 253:977–1055

    Article  CAS  Google Scholar 

  31. Dutta S, Padhye S, Priyadarsini KI, Newton C (2005) Bioorg Med Chem Lett 15:2738–2744

    Article  CAS  Google Scholar 

  32. Padhye S, Afrasiabi Z, Sinn E, Fok J, Mehta K, Rath N (2005) Inorg Chem 44:1154–1156

    Article  CAS  Google Scholar 

  33. Peters ZJ, Nykamp JA, Passaperuma K, Carlson JC, DeWitte-Orr SJ, Greenberg BM, Bols NC (2007) Reprod Toxicol 23:513–520

    Article  CAS  Google Scholar 

  34. Ahmad A, Wang Z, Kong D, Ali R, Ali S, Banerjee S, Sarkar FH (2011) Breast Cancer Res Treat 126:15–25

    Article  CAS  Google Scholar 

  35. Bruker (2002) SMART. Bruker AXS Inc., Madison

    Google Scholar 

  36. Bruker (2008) SAINT and SADABS. Bruker AXS Inc., Madison

    Google Scholar 

  37. Sheldrick GM (2008) Acta Cryst A64:112–122

    Google Scholar 

  38. Spek AL (2005) PLATON, a multipurpose crystallographic tool. Utrecht University, Utrecht

    Google Scholar 

  39. Akinchan NT, Akinchan R, West DX, Yang YH (1994) Transition Met Chem 19:135–140

    Article  CAS  Google Scholar 

  40. Chandra S, Gupta LK (2005) Spectrochim Acta A 61:269–275

    Article  Google Scholar 

  41. Mishra N, Mohapatra B, Guru S (1979) J Inorg Nucl Chem 41:408–410

    Article  CAS  Google Scholar 

  42. Rodríguez-Argüelles MC, Mosquera-Vázquez S, Sanmartín-Matalobos J, García-Deibe AM, Pelizzi C, Zani F (2010) Polyhedron 29:864–870

    Article  Google Scholar 

  43. Saleh AA, Khalil SME, Eid MF, El-Ghamry MA (2003) J Coord Chem 46:467–480

    Article  Google Scholar 

  44. West DX, Carlson CS, Galloway CP, Liberta AE, Daniels CR (1990) Transition Met Chem 15:91–95

    Article  CAS  Google Scholar 

  45. Seleem HS, El-Shetary BA, Khalil SME, Mostafa M, Shebl M (2005) J Coord Chem 58:479–493

    Article  CAS  Google Scholar 

  46. Ismail TMA, Saleh AA (2000) Egypt J Chem 43:227–235

    CAS  Google Scholar 

  47. Labisbal E, Sousa A, Castineiras A, Garacıa-Vazquez JA, Romero J, West DX (2000) Polyhedron 19:1255–1262

    Article  CAS  Google Scholar 

  48. Satpathy KC, Mishra R, Jal BB (1986) J Indian Chem Soc 68:377–379

    Google Scholar 

  49. König E (1971) Struct Bond (Berlin) 9:175–212

    Article  Google Scholar 

  50. Afrasiabi Z, Sinn E, Lin W, Ma Y, Campana C, Padhye S (2005) J Inorg Biochem 99:1526–1531

    Article  CAS  Google Scholar 

  51. Dutta S, Peng SM, Bhattacharya S (2000) Inorg Chem 39:2231–2234

    Article  CAS  Google Scholar 

  52. Goodman JH, Reibenspies N, Goswami S, Jurisson MY (1997) J Am Chem Soc 119:4955–4963

    Article  CAS  Google Scholar 

  53. Blake AJ, Gould RO, Halcrow MA, Schröeder M (1993) J Chem Soc Dalton Trans 19:2909–2920

    Google Scholar 

  54. Matsuzaki SY, Gotoh M, Kuboyama A (1987) Mol Cryst Liq Cryst 142:127–139

    Article  CAS  Google Scholar 

  55. Jouad EM, Allian M, Khan MA, Bouet GM (2005) Polyhedron 24:327–332

    Article  CAS  Google Scholar 

  56. Pal I, Dutta S, Basuli F, Goverdhan S, Peng S, Lee G, Bhattacharya S (2003) Inorg Chem 42:4338–4345

    Article  CAS  Google Scholar 

  57. Basuli F, Peng S, Bhattacharya S (2001) Inorg Chem 40:1126–1133

    Article  CAS  Google Scholar 

  58. Padhye S, Dandawate P, Yusufi M, Ahmad A, Sarkar FH (2012) Med Res Rev 32:1131–1158

    Article  CAS  Google Scholar 

  59. Chen J, Huang YW, Liu G, Afrasiabi Z, Sinn E, Padhye S, Ma Y (2004) Toxicol Appl Pharmacol 197:40–48

    Article  CAS  Google Scholar 

  60. Chikate RC, Padhye SB (2007) Spectrochim Acta A Mol Biomol Spectrosc 66:1091–1096

    Article  Google Scholar 

  61. Gokhale NH, Shirisha K, Padhye SB, Croft SL, Kendrick HD, Mckee V (2006) Bioorg Med Chem Lett 16:430–432

    Article  CAS  Google Scholar 

  62. Gokhale NH, Padhye SB, Croft SL, Kendrick HD, Davies W, Anson CE, Powell AK (2003) J Inorg Biochem 95:249–258

    Article  CAS  Google Scholar 

  63. Liguori PF, Valentini A, Palma M, Bellusci A, Bernardini S, Ghedini M, Panno ML, Pettinari C, Marchetti F, Crispini A, Pucci D (2010) Dalton Trans 39:4205–4212

    Article  CAS  Google Scholar 

  64. Ambike V, Adsule S, Ahmed F, Wang Z, Afrasiabi Z, Sinn E, Sarkar F, Padhye S (2007) J Inorg Biochem 101:1517–1524

    Article  CAS  Google Scholar 

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Acknowledgments

S.P. and A.V. are thankful to Mr. P. A. Inamdar and Dr. E. M. Khan for their keen interest and encouragement.

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Correspondence to Zahra Afrasiabi or Subhash Padhye.

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Afrasiabi, Z., Almudhafar, R., Xiao, D. et al. Metal-based anticancer agents: targeting androgen-dependent and androgen-independent prostate and COX-positive pancreatic cancer cells by phenanthrenequinone semicarbazone and its metal complexes. Transition Met Chem 38, 665–673 (2013). https://doi.org/10.1007/s11243-013-9735-3

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