Cytotoxic effects of dillapiole on MDA-MB-231 cells involve the induction of apoptosis through the mitochondrial pathway by inducing an oxidative stress while altering the cytoskeleton network

Biochimie

Volumn 99, Issue 1, 2014, Pages 195-207

  Ferreira, Adilson Kleber ^a   De Sá Júnior, Paulo Luiz ^a   Pasqualoto, Kerly Fernanda Mesquita ^a   De Azevedo, Ricardo Alexandre ^a   Câmara, Diana Aparecida Dias ^a   Costa, André Santos ^a   Figueiredo, Carlos Rogério ^b   Matsuo, Alisson Leonardo ^b   Massaoka, Mariana Hiromi ^b   Auada, Aline Vivian Vatti ^a   Lebrun, Ivo ^a   Damião, Mariana Celestina Frojuello Costa Bernstorff ^c   Tavares, Maurício Temotheo ^c   Magri, Fátima Maria Motter ^d   Kerkis, Irina ^a   Parise Filho, Roberto ^a,c  

^a INSTITUTO BUTANTAN   (Brazil)

^b FEDERAL UNIVERSITY OF SÃO PAULO   (Brazil)

^c UNIVERSITY OF SÃO PAULO   (Brazil)

^d MACKENZIE PRESBYTERIAN UNIVERSITY   (Brazil)

Author keywords

Antitumoral; Apoptosis; Cell cycle; Dillapiole; Molecular modeling; Piper aduncum; ROS

Indexed keywords

ANTITUMORAL; APOPTOSIS; CELL CYCLE; DILLAPIOLE; MOLECULAR MODELING; PIPER ADUNCUM; ROS;

ALLYL COMPOUNDS; ANTINEOPLASTIC AGENTS, PHYTOGENIC; APOPTOSIS; CALCIUM SIGNALING; CASPASE 3; CELL MOVEMENT; CELL SURVIVAL; CYTOSKELETON; DIOXOLES; DRUG SCREENING ASSAYS, ANTITUMOR; ELECTRON TRANSPORT COMPLEX IV; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HUMANS; MCF-7 CELLS; MEMBRANE POTENTIAL, MITOCHONDRIAL; MITOCHONDRIA; MOLECULAR DYNAMICS SIMULATION; OXIDATIVE STRESS; PIPER; PLANT EXTRACTS;

EID: 84894033242     PISSN: 03009084     EISSN: 61831638     Source Type: Journal    
DOI: 10.1016/j.biochi.2013.12.008     Document Type: Article

References (50)

1. A. Jemal, R. Siegel, E. Ward, T. Murray, J. Xu, and M.J. Thun Cancer statistics CA Cancer J. Clin. 57 2007 43 66
2. J.T. Ribeiro, L.T. Macedo, G. Curigliano, L. Fumagalli, M. Locatelli, M. Dalton, A. Quintela, J.B. Carvalheira, S. Manunta, L. Mazzarella, J. Brollo, and A. Goldhirsch Cytotoxic drugs for patients with breast cancer in the era of targeted treatment: back to the future? Ann. Oncol. 23 2012 547 555
3. J.J. Jobsen, J. Van-der-Palen, M. Brinkhuis, F. Ong, and H. Struikmans Sequence of radiotherapy and chemotherapy in breast cancer after breast-conserving surgery Int. J. Radiat. Oncol. Biol. Phys. 82 2012 e811 817 10.1016/j.ijrobp.2011.11.020
4. P.G. Tsoutsou, Y. Belkacemi, J. Gligorov, A. Kuten, H. Boussen, N. Bese, and M.I. Koukourakis Optimal sequence of implied modalities in the adjuvant setting of breast cancer treatment: an update on issues to consider Oncologist 15 2010 1169 1178
5. G. Llaverias, C. Danilo, I. Mercier, K. Daumer, F. Capozza, T.M. Williams, F. Sotgia, M.P. Lisanti, and P.G. Frank Role of cholesterol in the development and progression of breast cancer Am. J. Pathol. 178 2011 402 412 10.1016/j.ajpath.2010.11.005
6. J. Gao, W.A. Morgan, A. Sanchez-Medina, and O. Corcoran The ethanol extract of Scutellaria baicalensis and the active compounds induce cell cycle arrest and apoptosis including upregulation of p53 and Bax in human lung cancer cells Toxicol. Appl. Pharmacol. 254 2011 221 228
7. J.W. Li, and J.C. Vederas Drug discovery and natural products: end of an era or an endless frontier? Science 325 2009 161 165
8. T.G. Yunker The Piperaceae of Brazil: I-Piper-group I, II, III, IV Hohenia 2 1972 19 366
9. V.S. Parmar, S.C. Jain, K.S. Bisht, R. Jain, P. Taneja, A. Jha, O.D. Tyagi, A.K. Prasad, J. Wengel, C.E. Olsen, and P.M. Boll Phytochemistry of the genus Piper Phytochemistry 46 1997 597 673
10. R.R.P. Almeida, R.N.P. Souto, C.N. Bastos, M.H.L. da Silva, and J.G.S. Maia Chemical variation in Piper aduncum and biological properties of its dillapiole-rich essential oil Chem. Biodivers. 6 2009 1427 1434
11. C.B. Bernard, H.G. Krishnamurty, D. Chauret, T. Durst, B.J.R. Philogène, P. Sánchez-Vindas, C. Hasbun, L. Poveda, L. San Román, and J.T. Arnason Insecticidal defenses of Piperaceae from the neotropics J. Chem. Ecol. 21 1995 801 813
12. J.W. Lorder, and R.H. Neam Constituents from Piper banksii Phytochemistry 11 1972 2645 2646
13. A.P. Martins, L. Salgueiro, R. Vila, F. Tomi, S.C. Igueral, J. Casanova, A.P. Cunha, and T. Adzet Essential oils from four Piper species Phytochemistry 49 1998 2019 2023
14. O. Ekundayo, I. Laakso, R.M. Adegbola, B. Oguntimein, A. Sofowora, and R. Hiltunen Essential oil constituents of Ashanti pepper (Piper guineense) fruits (berries) J. Agric. Food Chem. 36 1988 880 882
15. J.W. Loder, A. Moorhouse, and G.B. Russell Tumour inhibitory plants. Amides of Piper novae-hollandiae (Piperaceae) Aust. J. Chem. 22 1969 1531 1538
16. L.S. Ramos, M.L. Silva, A.I.R. Luz, M.G.B. Zoghbi, and J.G.S. Maia Essential oil of Piper marginatum J. Nat. Prod. 49 1986 712 741
17. R. Parise-Filho, K.F.M. Pasqualoto, F.M.M. Magri, A.K. Ferreira, B.A.V.G. Da-Silva, M.C.F.C.B. Damião, M.T. Tavares, R.A. Azevedo, A.V.V. Auada, M.C. Polli, and C.A. Brandt Dillapiole as antileishmanial agent: discovery, cytotoxic activity and preliminary sar studies of dillapiole analogues Arch. Pharm. 345 2012 934 944
18. R. Parise-Filho, M. Pastrello, C.E.P. Camerlingo, G.J. Silva, L.A. Agostinho, T. Souza, F.M.M. Magri, R.R. Ribeiro, C.A. Brandt, and M.C. Polli The anti-inflammatory activity of dillapiole and some semisynthetic analogues Pharm. Biol. 49 2011 1173 1179
19. M.J.C. Araújo, C.A.G. Câmara, F.S. Born, M.M. Moraes, and C.A. Badji Acaricidal activity and repellency of essential oil from Piper aduncum and its components against Tetranychus urticae Exp. Appl. Acarol. 57 2012 139 155
20. E.H.A. Andrade, L.M.M. Carreira, M.H.L. Silva, J.D. Silva, C.N. Bastos, P.J.C. Sousa, E.F. Guimarães, and J.G.S. Maia Variability in essential-oil composition of Piper marginatum sensu lato Chem. Biodivers. 5 2008 197 208
21. 1 compounds from Piper lenticellosum J. Nat. Prod. 49 1986 690 691
22. C.B. Bernard, H.G. Krishinamurty, D. Chauret, T. Durst, B.J.R. Philogene, P. Sanchés-Vindas, C. Hasbaun, L. Poveda, L.S. Roman, and J.T. Arnason Inseticidal defenses of Piperaceae from the neotropics J. Chem. Ecol. 21 1995 801 814
23. M. Fazolin, J.L.V. Estrela, V. Catani, M.S. Lima, and M.R. Alécio Toxicidade do óleo de Piper aduncum L. a adultos de Cerotoma tingomarianus Bechyné (Coleóptera: Chrysomelidae) Neotrop. Entomol. 34 2005 485 489
24. V.A. Facundo, A.S.P. Silveira, and S.M. Morais Constituents of Piper alatabacum Trel & Yuncker (Piperaceae) Biochem. Syst. Ecol. 33 2005 753 756
25. F.S. Yu, J.S. Yang, C.S. Yu, C.C. Lu, J.H. Chiang, C.W. Lin, and J.G. Chung Safrole induces apoptosis in human oral cancer HSC-3 cells J. Dent. Res. 90 2011 168 174
26. C.S. Yu, A.C. Huang, J.S. Yang, C.C. Yu, C.C. Lin, H.K. Chung, Y.P. Huang, F.S. Chueh, and J.G. Chung Safrole induces G0/G1 phase arrest via inhibition of cyclin E and provokes apoptosis through endoplasmic reticulum stress and mitochondrion-dependent pathways in human leukemia HL-60, cells Anticancer Res. 32 2012 1671 1679
27. P. Ala, and D.S.C. Yang 6-[1-(4-Ethoxyphenyl)ethyl]-5-methoxy-1,3- benzodioxole Acta Crystallogr. C51 1995 1917 1919
28. M.J.S. Dewar, E.G. Zoebisch, E.F. Healy, and J.J.P. Stewart AM1: a new general purpose quantum mechanical molecular model J. Am. Chem. Soc. 107 1985 3903 3909
29. D. Doherty MOLSIM: Molecular Mechanics and Dynamics Simulation Software - User's Guide, Version 3.2 2002 The Chem21 Group Inc. Lake Forest, IL
30. C.M. Breneman, and K.B. Wiberg Determining atom-centered monopoles from molecular electrostatic potentials. The need for high sampling density in formamide conformational analysis J. Comput. Chem. 11 1990 361 373
31. A.D. Becke A new mixing of Hartree-Fock and local density-functional theories J. Chem. Phys. 98 1993 1372 1377
32. M.A. Robb, J.R. Cheeseman, J.A. Montgomery, T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomas, E.V. Baron, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari., J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, J.A. Pople, Gaussian, Inc., Wallingford CT, 2004.
33. GaussView for Windows, version 5.0 2000 2008 Gaussian, Inc. Pittsburgh, PA
34. V.N. Viswanadhan, A.K. Ghose, G.R. Revankar, and R.K. Robins Atomic physicochemical parameters for three-dimensional-structure-directed quantitative structure-activity relationships. 2. Modeling dispersive and hydrophobic interactions J. Chem. Inf. Comput. Sci. 29 1989 163 172
35. Marvin Beans 5.8.0 Software - Calculator Plugins 2012 Chemaxon, Ltd. Budapeste 1037, Hungary
36. R. Emmadi, and E.L. Wiley Evaluation of resection margins in breast conservation therapy: the pathology perspective-past, present, and future Int. J. Surg. Oncol. 2012 2012 1 9
37. T. Fukutomi Clinical practice and outcome of breast-conserving treatment: the effectiveness of preoperative systemic chemotherapy Breast Cancer 13 2006 147 151
38. G.V. Park, Y. Choi, Y.S. Kim, H.K. Lee, D. Kim, and D.Y. Hur ROS and ERK1/2-mediated caspase-9 activation increases XAF1 expression in dexamethasone-induced apoptosis of EBV-transformed B cells Int. J. Oncol. 43 2013 29 38
39. J. Montero, C. Dutta, D. Van-Bodegom, D. Weinstock, and A. Letai p53 regulates a non-apoptotic death induced by ROS Cell Death Differ. 2013 10.1038/cdd.2013.52
40. Y.C. Ye, H.J. Wang, L. Yu, S. Tashiro, S. Onodera, and T. Ikejima RIP1-mediated mitochondrial dysfunction and ROS production contributed to tumor necrosis factor alpha-induced L929 cell necroptosis and autophagy Int. Immunopharmacol. 14 2012 674 682
41. A. Tinari, A.M. Giammarioli, V. Manganelli, L. Ciarlo, and W. Malorni Analyzing morphological and ultrastructural features in cell death Meth. Enzymol. 442 2008 1 26
42. M. Yu, A. Bardia, B.S. Wittner, S.L. Stott, M.E. Smas, D.T. Ting, S.J. Isakoff, J.C. Ciciliano, M.N. Wells, A.M. Shah, K.F. Concannon, M.C. Donaldson, L.V. Sequist, E. Brachtel, D. Sgroi, J. Baselga, S. Ramaswamy, M. Toner, D.A. Haber, and S. Maheswaran Circulating breast tumor cells exhibit dynamic changes in epithelial and mesenchymal composition Science 339 2013 580 584
43. D.X. Nguyen, P.D. Bos, and J. Massagué Metastasis: from dissemination to organ-specific colonization Nat. Rev. Cancer 9 2009 274 284
44. 2-induced necrosis by PKC and AMP-activated kinase signaling in primary cultured hepatocytes Am. J. Physiol. Cell Physiol. 295 2008 c50 63
45. A. Ciucci, P. Gianferretti, R. Piva, T. Guyot, T.J. Snape, S.M. Roberts, and M.G. Santoro Induction of apoptosis in estrogen receptor-negative breast cancer cells by natural and synthetic cyclopentenones: role of the IkappaB kinase/nuclear factor-kappaB pathway Mol. Pharmacol. 70 2006 1812 1821
46. A.K. Ferreira, V.W. Freitas, D. Levy, J.L. Ruiz, S.P. Bydlowski, R.E. Rici, O.M. Filho, G.O. Chierice, and D.A. Maria Anti-angiogenic and anti-metastatic activity of synthetic phosphoethanolamine PLoS One 2013 10.1371/journal.pone.0057937
47. 2+ and apoptosis Cell Calcium 52 2012 36 43
48. 2+: a control point for apoptosis Science 300 2003 135 139
49. Q. Hu, D. Wu, W. Chen, Z. Yan, and Y. Shi Proteolytic processing of Caspase-9 zymogen is required for apoptosome-mediated activation of Caspase-9 J. Biol. Chem. 288 2013 15142 15147
50. S. Yuan, and C.W. Akey Apoptosome structure, assembly, and procaspase activation Structure 21 2013 501 515