Mechanism of inhibition of human cytochrome P450 1A1 and 1B1 by piceatannol

Biomolecules and Therapeutics

Volumn 16, Issue 4, 2008, Pages 336-342

  Chae, Ah Reum ^a   Shim, Jae Ho ^a   Chun, Young Jin ^a  

^a Chung Ang University   (South Korea)

Author keywords

Cytochrome P450; Enzyme inhibition; Piceatannol; Resveratrol

Indexed keywords

ALPHA NAPHTHOFLAVONE; CYTOCHROME P450 1A1; CYTOCHROME P450 1A2; CYTOCHROME P450 1B1; PICEATANNOL; PROTEIN KINASE B; RECOMBINANT ENZYME; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE FERRIHEMOPROTEIN REDUCTASE; RESVERATROL;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CARCINOMA CELL; CHEMOPROPHYLAXIS; COMPETITIVE INHIBITION; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG EFFECT; DRUG MECHANISM; DRUG SELECTIVITY; ENZYME ACTIVITY; ENZYME INHIBITION; ESCHERICHIA COLI; HUMAN; HUMAN CELL; HUMAN CELL CULTURE; IC 50; PROSTATE CARCINOMA; PROTEIN EXPRESSION; SIGNAL TRANSDUCTION;

ESCHERICHIA COLI; VITACEAE;

EID: 69549095795     PISSN: 19769148     EISSN: None     Source Type: Journal    
DOI: 10.4062/biomolther.2008.16.4.336     Document Type: Article

References (36)

1. Altomare, D. A. and Testa, J. R. (2005). Perturbations of the AKT signaling pathway in human cancer. Oncogene 24, 7455-7464. (Pubitemid 41637985)
2. Aziz, M. H., Nihal, M., Fu, V. X., Jarrard, D. F. and Ahmad, N. (2006). Resveratrol-caused apoptosis of human prostate carcinoma LNCaP cells is mediated via modulation of phosphatidylinositol 3′-kinase/Akt pathway and Bcl-2 family proteins. Mol. Cancer Ther. 5, 1335-1341. (Pubitemid 43881327)
3. Benistant, C., Chapuis, H. and Roche, S. (2000). A specific function for phosphatidylinositol 3-kinase alpha (p85 alphap110 alpha) in cell survival and for phosphatidylinositol 3- kinase beta (p85 α-p110 α) in de novo DNA synthesis of human colon carcinoma cells. Oncogene 19, 5083-5090. (Pubitemid 30826952)
4. Burke, M. D., Thompson, S., Elcombe, C. R., Halpert, J., Haaparanta, T. and Mayer, R. T. (1985). Ethoxy-, pentoxy- and benzyloxyphenoxazones and homologues: a series of substrates to distinguish between different induced cytochromes P-450. Biochem. Pharmacol. 34, 3337-3345. (Pubitemid 16215699)
5. Cecchinato, V., Chiaramonte, R., Nizzardo, M., Cristofaro, B., Basile, A., Sherbet, G. V. and Comi, P. (2007). Resveratrol-induced apoptosis in human T-cell acute lymphoblastic leukaemia MOLT-4 cells. Biochem. Pharmacol. 74, 1568-1574. (Pubitemid 47614962)
6. Chang, T. K., Lee, W. B. and Ko, H. H. (2000). Trans-resveratrol modulates the catalytic activity and mRNA expression of the procarcinogen- activating human cytochrome P450 1B1. Can. J. Physiol. Pharmacol. 78, 874-881. (Pubitemid 30951343)
7. Chun, Y. J., Kim, M. Y. and Guengerich, F. P. (1999). Resveratrol is a selective human cytochrome P450 1A1 inhibitor. Biochem. Biophys. Res. Commun. 262, 20-24.
8. Chun, Y. J. and Kim, S. (2003). Discovery of cytochrome P450 1B1 inhibitors as new anti-cancer agents. Med. Res. Rev. 23, 657-668.
9. Chun, Y. J., Kim, S., Kim, D., Lee, S. K. and Guengerich, F. P. (2001a). A new selective and potent inhibitor of human cytochrome P450 1B1 and its application to antimutagenesis. Cancer Res. 61, 8164-8170. (Pubitemid 33091608)
10. Chun, Y. J., Lee, S.K. and Kim, M. Y. (2005). Modulation of human cytochrome P450 1B1 expression by 2,4,3′,5′-tetramethoxystilbene. Drug Metab. Dispos. 33, 1771-1776. (Pubitemid 41697260)
11. Chun, Y. J., Ryu, S. Y., Jeong, T. C. and Kim, M. Y. (2001b). Mechanism based inhibition of human cytochrome P450 1A1 by rhapontigenin. Drug Metab. Dispos. 29, 389-393. (Pubitemid 32275551)
12. Ferrigni, N. R., McLaughlin, J. L., Powell, R. G. and Smith, C. R. (1984). Isolation of piceatannol as the antileukemic principle from the seeds of euphorbia lagascae. J. Nat. Prod. 47, 347-352.
13. Fleming, I., Fisslthaler, B. and Busse, R. (1995). Calcium signaling in endothelial cells involves activation of tyrosine kinases and leads to activation of MAP kinases. Circ. Res. 76, 522-529.
14. Gardai, S. J., Hildeman, D. A., Frankel, S. K., Whitlock, B. B., Frasch, S. C., Borregaard, N., Marrack, P., Bratton, D. L. and Henson, P. M. (2004). Phosphorylation of Bax Ser184 by Akt regulates its activity and apoptosis in neutrophils. J. Biol. Chem. 279, 21085-21095. (Pubitemid 38656511)
15. Geahlen, R. L. and McLaughlin, J. L. (1989). Piceatannol (3,4,3′,5′-tetrahydroxy-trans-stilbene) is a naturally occurring protein-tyrosine kinase inhibitor. Biochem. Biophys. Res. Commun. 165, 241-245.
16. Gross, A., McDonnell, J. M. and Korsmeyer, S. J. (1999). Bcl-2 family members and the mitochondria in apoptosis. Genes Dev. 13, 1899-1911. (Pubitemid 29407357)
17. Guengerich, F. P., Martin, M. V., Guo, Z. and Chun, Y. J. (1996). Purification of functional recombinant P450s from bacteria. Methods Enzymol. 272, 35-44. (Pubitemid 26299865)
18. Guengerich, F. P. and Shimada, T. (1991). Oxidation of toxic and carcinogenic chemicals by human cytochrome P-450 enzymes. Chem. Res. Toxicol. 4,381-407.
19. Hsieh, T., Juan, G., Darzynkiewicz, Z. and Wu, J. M. (1999). Resveratrol increases nitric oxide synthase, induces accumulation of p53 and p21(WAF1/CIP1), and suppresses cultured bovine pulmonary artery endothelial cell proliferation by perturbing progression through S and G2. Cancer Res. 59, 2596-2601. (Pubitemid 29269105)
20. Johnson, N. C., Dan, H. C., Cheng, J. Q. and Kruk, P. A. (2004). BRCA1 185delAG mutation inhibits Akt-dependent, IAP-mediated caspase 3 inactivation in human ovarian surface epithelial cells. Exp. Cell Res. 298, 9-16.
21. Kadlubar, F. F. and Hammons, G. J. (1987). The role of cytochrome P-450 in the metabolism of chemical carcinogens. In: Mammalian cytochromes P-450. Boca Raton: CRC Press; 1987. pp 81-130.
22. Kennedy, S. G., Wagner, A. J., Conzen, S. D., Jordan, J., Bellacosa, A., Tsichlis, P. N. and Hay, N. (1997). The PI3-kinase/Akt signaling pathway delivers an anti-apoptotic signal. Genes Dev. 11, 701-713. (Pubitemid 27157159)
23. Lee, S. K., Kim, Y., Kim, M. Y., Chun, Y. J. and Kim, S. (2004). Potent inhibition of recombinant human cytochrome P-450 1A1 by pentamethoxystilbene. J. Toxicol. Environ. Health Part A 67, 1987-2000. (Pubitemid 39488868)
24. Lee, S. H., Ryu, S. Y., Kim, H. B., Kim, M. Y. and Chun, Y. J. (2002). Induction of apoptosis by 3,4′-dimethoxy-5-hydroxystilbene in human promyeloid leukemic HL-60 cells. Planta Med. 68, 123-127. (Pubitemid 34169403)
25. Li, Y., Liu, J. Y., Liu, X. P., Xing, K. F., Wang Y., Li, F. Y. and Yao, L. (2006). Resveratrol-induced cell inhibition of growth and apoptosis in MCF7 human breast cancer cells are associated with modulation of phosphorylated Akt and caspase-9. Appl. Biochem. Biotechnol. 135,181-192. (Pubitemid 46252778)
26. Omura, T. and Sato, R. (1964). The carbon-monoxide binding pigment of liver microsomes. J. Biol. Chem. 239, 2370-2378.
27. Peters, J. D., Furlong, M. T., Asai, D. J., Harrison, M. L. and Geahlen, R. L. (1996). Syk, activated by cross-linking the Bcell antigen receptor, localises to the cytosol where it interacts with and phosphorylates a-tubulin on tyrosine. J. Biol. Chem. 271, 4755-4762.
28. Parikh, A., Gillam, E. M. and Guengerich, F. P. (1997). Drug metabolism by Escherichia coli expressing human cytochromes P450. Nat. Biotechnol. 15, 784-788. (Pubitemid 27329483)
29. So, K. S., Oh, J. E., Han, J. H., Jung, H. K., Lee, Y. S., Kim, S. H., Chun, Y. J. and Kim, M. Y. (2008). Induction of apoptosis by a stilbene analog involves Bax translocation regulated by p38 MAPK and Akt. Arch. Pharm. Res. 31, 438-444.
30. Su., L. and David, M. (2000). Distinct mechanisms of STAT phosphorylation via the interferon-a/b receptor, selective inhibition of STAT3 and STAT5 by piceatannol. J. Biol. Chem. 275, 12661-12666.
31. Surh, Y. J., Hurh, Y. J., Kang, J. Y., Lee, E., Kong, G. and Lee, S. J. (1999). Resveratrol, an antioxidant present in red wine, induces apoptosis in human promyelocytic leukemia (HL-60) cells. Cancer Lett. 140, 1-10. (Pubitemid 29251307)
32. Tsan, M. F., White, J. E., Maheshwari, J. G., Bremner, T. A. and Sacco, J. (2000). Resveratrol induces Fas signalling-independent apoptosis in THP-1 human monocytic leukemia cells. Brit. J. Haematol. 109, 405-412.
33. Tsuruta, F., Masuyama, N. and Gotoh Y. (2002). The phosphatidylinositol 3-kinase (PI3K)-Akt pathway suppresses Bax translocation to mitochondria. J. Biol. Chem. 277, 14040-14047. (Pubitemid 34968013)
34. Wrighton, S. A. and Stevens, J. C. (1992). The human hepatic cytochrome P450 involved in drug metabolism. Crit. Rev. Toxicol. 22,1-21.
35. Zha, J., Harada, H., Yang, E., Jockel, J. and Korsmeyer, S. J. (1996). Serine phosphorylation of death agonist BAD in response to survival factor results in binding to 14-3-3- not Bcl-XL. Cell 87, 619-628. (Pubitemid 26386936)
36. Zhou, H., Li, X. M., Meinkoth, J. and Pittman, R. N. (2000). Akt regulates cell survival and apoptosis at a postmitochondrial level. J. Cell. Biol. 151, 483-494. (Pubitemid 30828129)