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2019, Number 4

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Gac Med Mex 2019; 155 (4)

El ácido valproico como agente sensibilizador al tratamiento anticáncer

Luna-Palencia GR, Correa-Basurto J, Vásquez-Moctezuma I

Language: Spanish
References: 49
Page: 417-422
PDF size: 149.96 Kb.


ABSTRACT

Valproic acid is an antiepileptic drug with more than 50 years of clinical use. In the past decade, its anticancer effects were discovered. Analyses in groups of patients who used this drug for years have shown that it decreases the frequency of head and neck cancer. Recent studies show the anticancer effect of combining valproic acid with chemotherapy, biological therapy and antioxidant systems inhibitors, with exceptional results. In this review, we analyze the metabolism of valproic acid and its application against cancer.


REFERENCES

  1. Frazee LA, Foraker KC. Use of intravenous valproic acid for acute migraine. Ann Pharmacother. 2008;42:403-407.

  2. Rosenberg G. The mechanisms of action of valproate in neuropsychiatric disorders: can we see the forest for the trees? Cell Mol Life Sci. 2007; 64:2090-2103.

  3. Hanahan D, Weinberg RA. Hallmarks of cancer: the next generation. Cell. 2011;144 646-674.

  4. Dawson MA, Kouzarides T. Cancer epigenetics: from mechanism to therapy. Cell. 2012;150:12-27.

  5. Tessarz P, Kouzarides T. Histone core modifications regulating nucleosome structure and dynamics. Nat Rev Mol Cell Biol. 2014;15:703-708.

  6. Robey RW, Chakraborty AR, Basseville A, Luchenko V, Bahr J, Zhirong Zhan Z, et al. Histone deacetylase inhibitors: emerging mechanisms of resistance. Mol Pharm. 2011;8:2021-2031.

  7. Dawson MA, Kouzarides T. Cancer epigenetics: from mechanism to therapy. Cell. 2012;150:12-27.

  8. Seto E, Yoshida M. Erasers of histone acetylation: the histone deacetylase enzymes. Cold Spring Harb Perspect Biol. 2014;6:a018713.

  9. Choudhary C, Kumar C, Gnad F, Nielsen ML, Rehman M, Walther TC, et al. Lysine acetylation targets protein complexes and co-regulates major cellular functions. Science. 2009;325:834-840.

  10. Delcuve GP, Khan DH, Davie JR. Roles of histone deacetylases in epigenetic regulation: emerging paradigms from studies with inhibitors. Clinical Epigenetics. 2012;4:5.

  11. De-Ruijter AJM, Van-Gennip AH, Caron HN, Kemp S, Van Kuilenburg AB. Histone deacetylases (HDACs): characterization of the classical HDAC family. Biochem. J. 2003;370:737-749.

  12. Dejligbjerg M, Grauslund M, Litman T, Collins L, Qian X, Jeffers M, et al. Differential effects of class I isoform histone deacetylase depletion and enzymatic inhibition by belinostat or valproic acid in HeLa cells. Mol Cancer. 2008;7:70.

  13. Witt O, Deubzer HE, Lodrini M, Milde T, Oehme I. Targeting histone deacetylases in neuroblastoma. Curr Pharm Des. 2009;15:436-447.

  14. Silva MF, Aires CC, Lui PB, Ruiter JP, IJlst L, Durán M, et al. Valproic acid metabolism and its effects on mitochondrial fatty acid oxidation: a review. J Inherit Metab Dis. 2008;31:205-216.

  15. Puri AS, Sharma BC, Khan EM, Saraswat VA. Fatal fulminant hepatic failure due to sodium valproate in an adolescent. Indian Pediatr. 1994;31:207-210.

  16. Ho PC, Abbott FS, Zanger UM, Chang TK. Influence of CYP2C9 genotypes on the formation of a hepatotoxic metabolite of valproic acid in human liver microsomes. Pharmacogenomics J. 2003;3:335-342.

  17. Kiang TK, Ho PC, Anari MR, Tong V, Abbott FS, Chang TK. Contribution of CYP2C9, CYP2A6, and CYP2B6 to valproic acid metabolism in hepatic microsomes from individuals with the CYP2C9*1/*1 genotype. Toxicol Sci. 2006;94:261-271.

  18. Sedeque AJM, Fisher MB, Korzekwa KR, González FJ, Rettie AE. Human CYP2C9 and CYP2A6 mediate formation of the hepatotoxin 4-ene-valproic acid. J Pharmacol Exp Ther. 1997;283:698-703.

  19. Fantin VR, Richon VM. Mechanisms of resistance to histone deacetylase inhibitors and their therapeutic implications. Clin Cancer Res. 2007; 13:7237-7242.

  20. Olsen EA, Kim YH, Kuzel TM, Pacheco TR, Foss FM, Parker S, et al. Phase IIb multicenter trial of vorinostat in patients with persistent, progressive, or treatment refractory cutaneous T-cell lymphoma. J Clin Oncol. 2007;25:3109-3115.

  21. Bassett SA, Barnett MP. The role of dietary histone deacetylases (HDACs) inhibitors in health and disease. Nutrients. 2014;6:4273-4301.

  22. McGraw AL. Romidepsin for the treatment of T-cell lymphomas. Am J Health Syst Pharm. 2013;70:1115-1122.

  23. Garnock-Jones KP. Panobinostat: first global approval. Drugs. 2015; 75:695-704.

  24. Mercurio C, Minucci S, Pelicci PG. Histone deacetylases and epigenetic therapies of hematological malignancies. Pharmacol Res. 2010;62:18-34.

  25. Ghosh SK, Perrine SP, Williams RM, Faller DV. Histone deacetylase inhibitors are potent inducers of gene expression in latent EBV and sensitize lymphoma cells to nucleoside antiviral agents. Blood. 2012; 119:1008-1017.

  26. Fraga MF, Ballestar E, Villar-Garea A, Boix-Chornet G, Espada J, Schotta G, et al. Loss of acetylation at Lys16 and trimethylation at Lys20 of histone H4 is a common hallmark of human cancer. Nat Genet. 2005; 3:391-400.

  27. Thurn KT, Thomas S, Moore A, Munster PN. Rational therapeutic combinations with histone deacetylase inhibitors for the treatment of cancer. Future Oncol. 2011;7:263-283.

  28. Kirschbaum MH. Histone deacetylase inhibitors and Hodgkin´s lymphoma. Lancet Oncol. 2011;12:1178-1179.

  29. Zapotocky M, Mejstrikova E, Smetana K, Stary J, Trka J, Starkova J. Valproic acid triggers differentiation and apoptosis in AML1/ETO-positive leukemic cells specifically. Cancer Lett. 2012;319:144-153.

  30. Iacomino G, Medici MC, Russo GL. Valproic acid sensitizes K562 erythroleukemia cells to TRAIL/Apo2L-induced apoptosis. Anticancer Res. 2008;28:855-864.

  31. Göttlicher M, Minucci S, Zhu P, Krämer OH, Schimpf A, Giavara S, et al. Valproic acid defines a novel class of HDAC inhibitors inducing differentiation of transformed cells. EMBO J. 2001;20:6969-6978.

  32. Phiel CJ, Zhang F, Huang EY, Guenther MG, Lazar MA, Klein PS. Histone deacetylase is a direct target of valproic acid, a potent anticonvulsant, mood stabilizer, and teratogen. J Biol Chem. 2001;276:36734-36741.

  33. Khan N, Jeffers M, Kumar S, Hackett C, Boldog F, Khramtsov N, et al. Determination of the class and isoform selectivity of small-molecule histone deacetylase inhibitors. Biochem J. 2008;409:581-589.

  34. Bermúdez-Lugo JA, Perez-Gonzalez O, Rosales-Hernández MC, Ilizaliturri- Flores I, Trujillo-Ferrara J, Correa-Basurto J. Exploration of the valproic acid binding site on histone deacetylase 8 using docking and molecular dynamic simulations. J Mol Model. 2012;18:2301-2310.

  35. Münster P, Marchion D, Bicaku E, Lacevic M, Kim J, Centeno B, et al. Clinical and biological effects of valproic acid as a histone deacetylase inhibitor on tumor and surrogate tissues: phase I/II trial of valproic acid and epirubicin/FEC. Clin Cancer Res. 2009;15:2488-2496.

  36. Mohammed TA, Holen KD, Jaskula-Sztul R, Mulkerin DR, Lubner SJ, Schelman WR, et al. A pilot phase II study of valproic acid for treatment of low-grade neuroendocrine carcinoma. Oncologist. 2011;16:835-843.

  37. Kuendgen A, Knipp S, Fox F, Strupp C, Hildebrandt B, Steidl C, et al. Results of a phase 2 study of valproic acid alone or in combination with all-trans retinoic acid in 75 patients with myelodysplastic syndrome and relapsed or refractory acute myeloid leukemia. Ann Hematol. 2005; 84:61-66.

  38. Pilatrino C, Cilloni D, Messa E, Morotti A, Giugliano E, Pautasso M, et al. Increase in platelet count in older, poor-risk patients with acute myeloid leukemia or myelodysplastic syndrome treated with valproic acid and all-trans retinoic acid. Cancer. 2005;104:101-109.

  39. Fenaux P, Mufti GJ, Hellstrom-Lindberg E, Santini V, Finelli C, Giagounidis A, et al. Efficacy of azacitidine compared with that of conventional care regimens in the treatment of higher-risk myelodysplastic syndromes: a randomised, open-label, phase III study. Lancet Oncol. 2009; 10:223-232.

  40. Fenaux P, Mufti GJ, Hellström-Lindberg E, Santini V, Gattermann N, Germing U, et al. Azacitidine prolongs overall survival compared with conventional care regimens in elderly patients with low bone marrow blast count acute myeloid leukemia. J Clin Oncol. 2010;28:562-569.

  41. Raffoux E, Cras A, Recher C, Boëlle PY, De Labarthe A, Turlure P, et al. Phase 2 clinical trial of 5-azacitidine, valproic acid, and all-trans retinoic acid in patients with high-risk acute myeloid leukemia or myelodysplastic syndrome. Oncotarget. 2010;1:34-42.

  42. Münster P, Marchion D, Bicaku E, Schmitt M, Lee JH, DeConti R, et al. Phase I trial of histone deacetylase inhibition by valproic acid followed by the topoisomerase II inhibitor epirubicin in advanced solid tumors: a clinical and translational study. J Clin Oncol. 2007;25:1979-1985.

  43. Scherpereel A, Berghmans T, Lafitte JJ, Colinet B, Richez M, Bonduelle Y, et al. Valproate-doxorubicin: promising therapy for progressing mesothelioma. A phase II study. Eur Respir J. 2011;37:129-135.

  44. Daud AI, Dawson J, DeConti RC, Bicaku E, Marchion D, Bastien S, et al. Potentiation of a topoisomerase I inhibitor, karenitecin, by the histone deacetylase inhibitor valproic acid in melanoma: translational and phase I/II clinical trial. Clin Cancer Res. 2009;15:2479-2487.

  45. Coronel J, Cetina L, Pacheco I, Trejo-Becerril C, González-Fierro A, De la Cruz-Hernández E, et al. A double-blind, placebo-controlled, randomized phase III trial of chemotherapy plus epigenetic therapy with hydralazine valproate for advanced cervical cancer. Preliminary results. Med Oncol. 2011;28:S540-S546.

  46. Juengel E, Dauselt A, Makarević J, Wiesner C, Tsaur I, Bartsch G, et al. Acetylation of histone H3 prevents resistance development caused by chronic mTOR inhibition in renal cell carcinoma cells. Cancer Lett. 2012;324:83-90.

  47. Kang H, Gillespie TW, Goodman M, Brodie SA, Brandes M, Ribeiro M, et al. Long-term use of valproic acid in US veterans is associated with a reduced risk of smoking-related cases of head and neck cancer. Cancer. 2014;120:1394-1400.

  48. Luna-Palencia GR, Martínez-Ramos F, Vásquez-Moctezuma I, Fragoso- Vázquez MJ, Mendieta-Wejebe JE, Padilla-Martínez II, et al. Three amino acid derivatives of valproic acid: design, synthesis, theoretical and experimental evaluation as anticancer agents. Anticancer Agents Med Chem. 2014;14:984-993.

  49. Prestegui-Martel B, Bermúdez-Lugo JA, Chávez-Blanco A, Dueñas-González A, García-Sánchez JR, Pérez-González OA, et al. N-(2-hydroxyphenyl)- 2-propylpentanamide, a valproic acid aryl derivative designed in silico with improved anti-proliferative activity in HeLa, rhabdomyosarcoma and breast cancer cells. J Enzyme Inhib Med Chem. 2016;31:140-149




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