Insights into the mechanisms underlying the antiproliferative potential of a Co(II) coordination compound bearing 1,10-phenanthroline-5,6-dione: DNA and protein interaction studies

详细信息    查看全文

• 作者：Daniel V. Luís (1)
  Joana Silva (1)
  Ana Isabel Tomaz (2)
  Rodrigo F. M. de Almeida (3)
  Miguel Larguinho (1)
  Pedro V. Baptista (1)
  Luísa M. D. R. S. Martins (4) (5)
  Telma F. S. Silva (4)
  Pedro M. Borralho (6) (7)
  Cecília M. P. Rodrigues (6) (7)
  António S. Rodrigues (8)
  Armando J. L. Pombeiro (4)
  Alexandra R. Fernandes (1) (4) (9)
  
• 关键词：Cobalt ; 1 ; 10 ; Phenanthroline ; 5 ; 6 ; dione ; Apoptosis ; DNA cleavage ; Human serum albumin
• 刊名：Journal of Biological Inorganic Chemistry
• 出版年：2014
• 出版时间：August 2014
• 年：2014
• 卷：19
• 期：6
• 页码：787-803
• 全文大小：1,286 KB
• 参考文献：1. Hannon MJ (2007) Pure Appl Chem 2243-261
  2. Meggers E (2009) Chem Commun 1001-010. doi:10.1039/b813568a
  3. Zhang CX, Lippard SJ (2003) Curr Opin Chem Biol 7:481-89 CrossRef
  4. Cantero G, Pastor N, Mateos S, Campanella C, Cortes F (2006) Mutat Res 599:160-66. doi:10.1016/j.mrfmmm.2006.02.006 CrossRef
  5. Zeglis BM, Pierre VC, Barton JK (2007) Chem Commun 4565-579. doi:10.1039/b710949k
  6. Williams NH, Takasaki B, Wall M, Chin J (1999) Acc Chem Res 32:485-93 CrossRef
  7. Jiang Q, Xiao N, Shi PF, Zhu YG, Guo ZJ (2007) Coord Chem Rev 251:1951-972. doi:10.1016/j.ccr.2007.02.013 CrossRef
  8. Pasini A, Zunino F (1987) Angew Chem Int Ed Engl 26:615-24. doi:10.1002/anie.198706151 CrossRef
  9. Barton JK (1986) Science 233:727-34 CrossRef
  10. Wang J, Cai X, Rivas G, Shiraishi H, Farias PA, Dontha N (1996) Anal Chem 68:2629-634 CrossRef
  11. Wheate NJ, Brodie CR, Collins JG, Kemp S, Aldrich-Wright JR (2007) Mini Rev Med Chem 7(6):627-48 CrossRef
  12. Cusumano M, Di Pietro ML, Giannetto A (2006) Inorg Chem 45:230-35. doi:10.1021/ic050880o CrossRef
  13. Liu HK, Sadler PJ (2011) Acc Chem Res 44(5):349-59. doi:10.1021/ar100140e
  14. Dhar S, Senapati D, Das PK, Chattopadhyay P, Nethaji M, Chakravarty AR (2003) J Am Chem Soc 125:12118-2124. doi:10.1021/ja036681q CrossRef
  15. Patra AK, Dhar S, Nethaji M, Chakravarty AR (2003) Chem Commun 1562-563
  16. Reddy PA, Santra BK, Nethaji M, Chakravarty AR (2004) J Inorg Biochem 98:377-86 CrossRef
  17. Ranford JD, Sadler PJ, Tocher DA (1993) J Chem Soc Dalton Trans 3393-399. doi:10.1039/DT9930003393
  18. Bruijnincx PC, Sadler PJ (2008) Curr Opin Chem Biol 12:197-06. doi:10.1016/j.cbpa.2007.11.013 CrossRef
  19. Gabbiani C (2009) Proteins as possible targets for antitumor metal complexes. Biophysical studies of their interactions. Firenze University Press, Florence
  20. Hernandes MZ, Pontes FJ de S, Coelho LCD, Moreira DRM, Pereira VRA, Leite ACL (2010) Curr Med Chem 17:3739-750
  21. Pessoa JC, Tomaz I (2010) Curr Med Chem 17:3701-738 CrossRef
  22. US Food and Drug Administration (2006) Requirements on content and format of labeling for human prescription drug and biological products, section 12: clinical pharmacology, subsection 12.3: pharmacokinetics, p?262. http://www.fda.gov/OHRMS/DOCKETS/98fr/00n-1269-nfr0001-03.pdf
  23. Colmenarejo G (2003) Med Res Rev 23:275-01. doi:10.1002/med.10039 CrossRef
  24. Kratz F (2008) J Control Release 132:171-83. doi:10.1016/j.jconrel.2008.05.010 CrossRef
  25. Maeda H (2010) Bioconjug Chem 21:797-02. doi:10.1021/bc100070g CrossRef
  26. Silva TFS, Smoleński P, Martins LMDRS, Guedes da Silva MFC, Fernandes AR, Luis D, Silva A, Santos S, Borralho PM, Rodrigues CMP, Pombeiro AJL (2013) Eur J Inorg Chem 2013:3651-658. doi:10.1002/ejic.201300197 CrossRef
  27. Silva A, Luis D, Santos S, Silva J, Mendo AS, Coito L, Silva TF, da Silva MF, Martins LM, Pombeiro AJ, Borralho PM, Rodrigues CM, Cabral MG, Videira PA, Monteiro C, Fernandes AR (2013) Drug Metab Drug Interact 28:167-76. doi:10.1515/dmdi-2013-0015
  28. Heintz RA, Smith JA, Szalay PS, Weisgerber A, Dunbar KR (2002) In: Coucouvanis D (ed) Inorganic synthesis, vol 33. Wiley, New York, pp 75-07
  29. Silva TFS, Martins LMDRS, Guedes da Silva MFC, Fernandes AR, Silva A, Borralho PM, Santos S, Rodrigues CMP, Pombeiro AJL (2012) Dalton Trans 41:12888-2897. doi:10.1039/C2DT11577H CrossRef
  30. Schmittgen TD, Livak KJ (2008) Nat Protoc 3:1101-108 CrossRef
  31. Li Y, Liu J, Li Q (2010) Mol Carcinog 49:566-81. doi:10.1002/mc.20623
  32. Rahman KW, Li Y, Wang Z, Sarkar SH, Sarkar FH (2006) Cancer Res 66:4952-960. doi:10.1158/0008-5472.CAN-05-3918 CrossRef
  33. Kanakis CD, Tarantilis PA, Polissiou MG, Diamantoglou S, Tajmir-Riahi HA (2007) Cell Biochem Biophys 49:29-6 CrossRef
  34. Conde J, Larguinho M, Cordeiro A, Raposo LR, Costa PM, Santos S, Diniz MS, Fernandes AR, Baptista PV (2014) Nanotoxicology 8:521-32
  35. Jakusch T, Hollender D, Enyedy EA, Gonzalez CS, Montes-Bayon M, Sanz-Medel A, Costa Pessoa J, Tomaz I, Kiss T (2009) Dalton Trans 2428-437. doi:10.1039/B817748A
  36. Valeur B (2001) Molecular fluorescence. Wiley-VCH, Weinheim, pp 155-99
  37. Hampton MB, Orrenius S (1997) FEBS Lett 414:552-56 CrossRef
  38. Dosa PI, Ward T, Castro RE, Rodrigues CM, Steer CJ (2013) ChemMedChem 8:1002-011. doi:10.1002/cmdc.201300059 CrossRef
  39. Takaki K, Higuchi Y, Hashii M, Ogino C, Shimizu N (2013) J Biosci Bioeng. doi:10.1016/j.jbiosc.2013.06.003
  40. Tang HL, Yuen KL, Tang HM, Fung MC (2009) Br J Cancer 100:118-22. doi:10.1038/sj.bjc.6604802 CrossRef
  41. Xie X, Wang S, Wong TC, Fung M (2013) Cancer Cell Int 13:63 CrossRef
  42. Amaral JD, Castro RE, Steer CJ, Rodrigues CM (2009) Trends Mol Med 15:531-41. doi:10.1016/j.molmed.2009.09.005 CrossRef
  43. Amaral JD, Castro RE, Sola S, Steer CJ, Rodrigues CM (2007) J Biol Chem 282:34250-4259. doi:10.1074/jbc.M704075200 CrossRef
  44. Taguchi T, Kato Y, Baba Y, Nishimura G, Tanigaki Y, Horiuchi C, Mochimatsu I, Tsukuda M (2004) Oncol Rep 11:421-26
  45. Gartel AL, Tyner AL (2002) Mol Cancer Ther 1:639-49
  46. Ramakrishnan S, Suresh E, Riyasdeen A, Akbarsha MA, Palaniandavar M (2011) Dalton Trans 40:3245-256. doi:10.1039/c0dt01360a CrossRef
  47. Karidi K, Garoufis A, Tsipis A, Hadjiliadis N, den Dulk H, Reedijk J (2005) Dalton Trans 1176-187. doi:10.1039/b418838a4
  48. Babu MSS, Reddy KH, Krishna PG (2007) Polyhedron 26:572-80. doi:10.1016/j.poly.2006.08.026 CrossRef
  49. Modica-Napolitano JS, Aprille JR (2001) Adv Drug Deliv Rev 49:63-0 CrossRef
  50. Obe G, Johannes C, Ritter S (2010) Mutat Res 701:3-1. doi:10.1016/j.mrgentox.2010.05.010 CrossRef
  51. Jung Y, Lippard J (2007) Chem Rev 107:1387-407 CrossRef
  52. Matos CP, Valente A, Marques F, Ad?o P, Paula Robalo M, de Almeida RFM, Pessoa JC, Santos I, Helena Garcia M, Tomaz AI (2013) Inorg Chim Acta 394:616-26. doi:10.1016/j.ica.2012.09.026 CrossRef
  53. Demoro B, de Almeida RFM, Marques F, Matos CP, Otero L, Costa Pessoa J, Santos I, Rodriguez A, Moreno V, Lorenzo J, Gambino D, Tomaz AI (2013) Dalton Trans 42:7131-146. doi:10.1039/C3DT00028A CrossRef
  54. Rohacova J, Marin ML, Miranda MA (2010) J Phys Chem B 114:4710-716. doi:10.1021/jp911114n CrossRef
  55. Honore B, Pedersen AO (1989) Biochem J 258:199-04
  56. Loura LM, de Almeida RF, Coutinho A, Prieto M (2003) Chem Phys Lipids 122:77-6 CrossRef
  
• 作者单位：Daniel V. Luís (1)
  Joana Silva (1)
  Ana Isabel Tomaz (2)
  Rodrigo F. M. de Almeida (3)
  Miguel Larguinho (1)
  Pedro V. Baptista (1)
  Luísa M. D. R. S. Martins (4) (5)
  Telma F. S. Silva (4)
  Pedro M. Borralho (6) (7)
  Cecília M. P. Rodrigues (6) (7)
  António S. Rodrigues (8)
  Armando J. L. Pombeiro (4)
  Alexandra R. Fernandes (1) (4) (9)
  
  1. Departamento Ciências da Vida, Faculdade de Ciências e Tecnologia, Universidade Nova de Lisboa, 2829-516, Caparica, Portugal
  2. Centro de Ciências Moleculares e Materiais, Faculdade de Ciências, Universidade de Lisboa, Campo Grande, 1749-016, Lisbon, Portugal
  3. Centro de Química e Bioquímica, Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade de Lisboa, 1749-016, Lisbon, Portugal
  4. Centro de Química Estrutural, Complexo I, Instituto Superior Técnico, Universidade de Lisboa, Lisbon, Portugal
  5. Area Departamental de Engenharia Química, ISEL, Lisbon, Portugal
  6. Departamento de Bioquímica e Biologia Humana, Faculdade de Farmácia, Universidade de Lisboa, Lisbon, Portugal
  7. Research Institute for Medicines and Pharmaceutical Sciences (iMed.UL), Faculdade de Farmácia, Universidade de Lisboa, Lisbon, Portugal
  8. Centro de Investiga??o em Genética Molecular e Humana, Departamento de Genética, Faculdade de Ciências Médicas, Universidade Nova de Lisboa, Lisbon, Portugal
  9. Faculdade de Engenharia, Universidade Lusófona de Humanidades e Tecnologias, Lisbon, Portugal
  
• ISSN：1432-1327

文摘

The very high antiproliferative activity of [Co(Cl)(H2O)(phendione)2][BF4] (phendione is 1,10-phenanthroline-5,6-dione) against three human tumor cell lines (half-maximal inhibitory concentration below?1?μM) and its slight selectivity for the colorectal tumor cell line compared with healthy human fibroblasts led us to explore the mechanisms of action underlying this promising antitumor potential. As previously shown by our group, this complex induces cell cycle arrest in S?phase and subsequent cell death by apoptosis and it also reduces the expression of proteins typically upregulated in tumors. In the present work, we demonstrate that [Co(Cl)(phendione)2(H2O)][BF4] (1) does not reduce the viability of nontumorigenic breast epithelial cells by?more than?85?% at 1?μM, (2) promotes the upregulation of proapoptotic Bax and cell-cycle-related p21, and (3) induces release of lactate dehydrogenase, which is partially reversed by ursodeoxycholic acid. DNA interaction studies were performed to uncover the genotoxicity of the complex and demonstrate that even though it displays K b (±?standard error of the mean) of (3.48 ±?0.03)?×?105?M? and is able to produce double-strand breaks in a concentration-dependent manner, it does not exert any clastogenic effect ex vivo, ruling out DNA as a major cellular target for the complex. Steady-state and time-resolved fluorescence spectroscopy studies are indicative of a strong and specific interaction of the complex with human serum albumin, involving one binding site, at a distance of?approximately 1.5?nm for the Trp214 indole side chain with log K b?~4.7, thus suggesting that this complex can be efficiently transported by albumin in the blood plasma.