Biochemical mechanism of Caffeic Acid Phenylethyl Ester (CAPE) selective toxicity towards melanoma cell lines

Chemico-Biological Interactions

Volumn 188, Issue 1, 2010, Pages 1-14

  Kudugunti, Shashi K ^a   Vad, Nikhil M ^a   Whiteside, Amanda J ^a   Naik, Bhakti U ^a   Yusuf, Mohd A ^a   Srivenugopal, Kalkunte S ^a   Moridani, Majid Y ^a  

^a TEXAS TECH UNIVERSITY HEALTH SCIENCES CENTER   (United States)

Author keywords

Caffeic acid; Cancer; CAPE; GSH; Melanoma; Quinone; SK MEL 28

Indexed keywords

1 BROMOHEPTANE; 4 HYDROXYPROPIONIC ACID DERIVATIVE; ASCORBIC ACID; CAFFEIC ACID; CAFFEIC ACID PHENETHYL ESTER; CHLOROGENIC ACID; CINNAMIC ACID; CYCLOSPORIN A; DICOUMAROL; DIHYDROCAFFEIC ACID; DIHYDROCINNAMIC ACID; FERULIC ACID; GLUTATHIONE; HEPTANE DERIVATIVE; HYDROCINNAMIC ACID DERIVATIVE; MESSENGER RNA; MONOPHENOL MONOOXYGENASE; PARA COUMARIC ACID; PROPIONIC ACID DERIVATIVE; QUINONE DERIVATIVE; REACTIVE OXYGEN METABOLITE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE; SHORT HAIRPIN RNA; TRIFLUOPERAZINE; UNCLASSIFIED DRUG; CAFFEIC ACID DERIVATIVE; NICOTINAMIDE ADENINE DINUCLEOTIDE; PHENETHYL ALCOHOL;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CANCER INHIBITION; CONTROLLED STUDY; CYTOTOXICITY; DRUG ANTAGONISM; DRUG POTENTIATION; DRUG TARGETING; ENZYME ACTIVITY; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; MALE; MELANOMA CELL; NONHUMAN; OXIDATION; OXIDATIVE STRESS; RAT; ANALOGS AND DERIVATIVES; ANIMAL; DRUG EFFECTS; ENZYMOLOGY; EXPERIMENTAL MELANOMA; METABOLISM; PATHOLOGY; SPRAGUE DAWLEY RAT; TOXICITY; TUMOR CELL LINE; ULTRAVIOLET SPECTROPHOTOMETRY;

ANIMALS; APOPTOSIS; ASCORBIC ACID; CAFFEIC ACIDS; CELL LINE, TUMOR; GLUTATHIONE; MALE; MELANOMA, EXPERIMENTAL; MONOPHENOL MONOOXYGENASE; NAD; PHENYLETHYL ALCOHOL; RATS; RATS, SPRAGUE-DAWLEY; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 77956173651     PISSN: 00092797     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cbi.2010.05.018     Document Type: Article

References (48)

1. Smit N.P., Peters K., Menko W., Westerhof W., Pavel S., Riley P.A. Cytotoxicity of a selected series of substituted phenols towards cultured melanoma cells. Melanoma Res. 1992, 2:295-304.
2. Saleem M., Maddodi N., Abu Zaid M., Khan N., bin Hafeez B., Asim M., et al. Lupeol inhibits growth of highly aggressive human metastatic melanoma cells in vitro and in vivo by inducing apoptosis. Clin. Cancer Res. 2008, 14:2119-2127.
3. Borden E.C. Melanoma 2007: current state and preview of the future. Semin. Oncol. 2007, 34:449-451.
4. Zheng Z.S., Xue G.Z., Grunberger D., Prystowsky J.H. Caffeic acid phenethyl ester inhibits proliferation of human keratinocytes and interferes with the EGF regulation of ornithine decarboxylase. Oncol. Res. 1995, 7:445-452.
5. Chen J.H., Ho C. Antioxidant activities of caffeic acid and its related hydroxycinnamic acid compounds. J. Agric. Food Chem. 1997, 45:2374.
6. Nagaoka T., Banskota A.H., Tezuka Y., Saiki I., Kadota S. Selective antiproliferative activity of caffeic acid phenethyl ester analogues on highly liver-metastatic murine colon 26-L5 carcinoma cell line. Bioorg. Med. Chem. 2002, 10:3351-3359.
7. Guarini L., Su Z.Z., Zucker S., Lin J., Grunberger D., Fisher P.B. Growth inhibition and modulation of antigenic phenotype in human melanoma and glioblastoma multiforme cells by caffeic acid phenethyl ester (CAPE). Cell Mol. Biol. 1992, 38:513-527.
8. Grunberger D., Banerjee R., Eisinger K., Oltz E.M., Efros L., Caldwell M., et al. Preferential cytotoxicity on tumor cells by caffeic acid phenethyl ester isolated from propolis. Experientia 1988, 44:230-232.
9. Lee Y.J., Liao P.H., Chen W.K., Yang C.Y. Preferential cytotoxicity of caffeic acid phenethyl ester analogues on oral cancer cells. Cancer Lett. 2000, 153:51-56.
10. Chen J.H., Shao Y., Huang M.T., Chin C.K., Ho C.T. Inhibitory effect of caffeic acid phenethyl ester on human leukemia HL-60 cells. Cancer Lett. 1996, 108:211-214.
11. Su Z.Z., Grunberger D., Fisher P.B. Suppression of adenovirus type 5 E1A-mediated transformation and expression of the transformed phenotype by caffeic acid phenethyl ester (CAPE). Mol. Carcinog. 1991, 4:231-242.
12. Kudugunti S.K., Vad N.M., Ekogbo E., Moridani M.Y. Efficacy of caffeic acid phenethyl ester (CAPE) in skin B16-F0 melanoma tumor bearing C57BL/6 mice. Invest New Drugs 2009, (Epub ahead of print).
13. Chen Y.M., Chavin W. Tyrosinase activity in a highly pigmented human melanoma and in negro skin. Proc. Soc. Exp. Biol. Med. 1974, 145:695-698.
14. Moridani M.Y. Biochemical basis of 4-hydroxyanisole induced cell toxicity towards B16-F0 melanoma cells. Cancer Lett. 2006, 243:235-245.
15. Thörneby-Andersson K., Sterner O., Hansson C. Tyrosinase-mediated formation of a reactive quinone from the depigmenting agents, 4-tert-butylphenol and 4-tert-butylcatechol. Pigment Cell Res. 2000, 13:33-38.
16. Vad N.M., Yount G., Moore D., Weidanz J., Moridani M.Y. Biochemical mechanism of acetaminophen (APAP) induced toxicity in melanoma cell lines. J. Pharm. Sci. 2009, 98:1409-1425.
17. Doherty M.D., Cohen G.M., Gant T.W., Naish S., Riley P.A. Metabolism of 1-naphthol by tyrosinase. Biochem. Pharmacol. 1985, 34:3167-3172.
18. Moridani M.Y., Cheon S.S., Khan S., O'Brien P.J. Metabolic activation of 4-hydroxyanisole by isolated rat hepatocytes. Drug Metab. Dispos. 2002, 30:1063-1069.
19. Ellman G.L. Tissue sulfhydryl groups. Arch. Biochem. Biophys. 1959, 82:70-77.
20. Moridani M.Y., Moore M., Bartsch R.A., Yang Y., Heibati-Sadati S. Structural toxicity relationship of 4-alkoxyphenols' cytotoxicity towards murine B16-F0 melanoma cell line. J. Pharm. Pharm. Sci. 2005, 8:348-360.
21. Dallner G. Isolation of microsomal subfractions by use of density gradients. Methods Enzymol. 1978, 52:71-82.
22. Krikun G., Cederbaum A.I. Increased microsomal oxidation of alcohols after pyrazole treatment and its similarities to the induction by ethanol consumption. Biochim. Biophys. Acta 1984, 801:131-137.
23. Moridani M.Y., Siraki A., O'Brien P.J. Quantitative structure toxicity relationships for phenols in isolated rat hepatocytes. Chem. Biol. Interact. 2003, 145:213-223.
24. Gergel D., Cederbaum A.I. Interaction of nitric oxide with 2-thio-5-nitrobenzoic acid: implications for the determination of free sulfhydryl groups by Ellman's reagent. Arch. Biochem. Biophys. 1997, 347:282-288.
25. Moldeus P., Hogberg J., Orrenius S. Isolation and use of liver cells. Methods Enzymol. 1978, 52:60-71.
26. Wu X., Zeng H., Zhang X., Zhao Y., Sha H., Ge X., et al. Phosphatase of regenerating liver-3 promotes motility and metastasis of mouse melanoma cells. Am. J. Pathol. 2004, 164:2039-2054.
27. Siraki A.G., Chan T.S., O'Brien P.J. Application of quantitative structure-toxicity relationships for the comparison of the cytotoxicity of 14 p-benzoquinone congeners in primary cultured rat hepatocytes versus PC12 cells. Toxicol. Sci. 2004, 81:148-159.
28. Preusch P.C., Siegel D., Gibson N.W., Ross D. A note on the inhibition of DT-diaphorase by dicoumarol. Free Radic. Biol. Med. 1991, 11:77-80.
29. Khan S., O'Brien P.J. 1-Bromoalkanes as new potent nontoxic glutathione depletors in isolated rat hepatocytes. Biochem. Biophys. Res. Commun. 1991, 179:436-441.
30. Broekemeier K.M., Pfeiffer D.R. Cyclosporin A-sensitive and insensitive mechanisms produce the permeability transition in mitochondria. Biochem. Biophys. Res. Commun. 1989, 163:561-566.
31. Wong A., Cavelier L., Collins-Schramm H.E., Seldin M.F., McGrogan M., Savontaus M.L., Cortopassi G.A. Differentiation-specific effects of LHON mutations introduced into neuronal NT2 cells. Hum. Mol. Genet. 2002, 11:443-448.
32. Johansen I.E. Intron insertion facilitates amplification of cloned virus cDNA in Escherichia coli while biological activity is reestablished after transcription in vivo. Proc. Natl. Acad. Sci. U.S.A. 1996, 93:12400-12405.
33. Vad N.M., Kudugunti S.K., Graber D., Bailey N., Srivenugopal K., Moridani M.Y. Efficacy of acetaminophen in skin B16-F0 melanoma tumor-bearing C57BL/6 mice. Int. J. Oncol. 2009, 35:193-204.
34. Shang X.J., Yao G., Ge J.P., Sun Y., Teng W.H., Huang Y.F. Procyanidin induces apoptosis and necrosis of prostate cancer cell line PC-3 in a mitochondrion-dependent manner. J. Androl. 2009, 30:122-126.
35. Vad N.M., Kandala P.K., Srivastava S.K., Moridani M.Y. Structure-toxicity relationship of phenolic analogs as anti-melanoma agents: an enzyme directed prodrug approach. Chem. Biol. Interact. 2010, 183:462-471.
36. Vad N.M., Yount G., Moridani M.Y. Biochemical mechanism of acetylsalicylic acid (Aspirin) selective toxicity toward melanoma cell lines. Melanoma Res. 2008, 18:386-399.
37. Passi S., Nazzaro-Porro M. Molecular basis of substrate and inhibitory specificity of tyrosinase: phenolic compounds. Br. J. Dermatol. 1981, 104:659-665.
38. Nakamura M., Yamazaki I., Kotani T., Ohtaki S. Thyroid peroxidase selects the mechanism of either 1- or 2-electron oxidation of phenols, depending on their substituents. J. Biol. Chem. 1985, 260:13546-13552.
39. Hirosaki K, Yamashita T., Wada I., Jin H.Y., Jimbow K. Tyrosinase and tyrosinase-related protein 1 require Rab7 for their intracellular transport. J. Invest. Dermatol. 2002, 119:475-480.
40. Kawai S., Yoshinari M., Matsumoto J., Kirinoki M., Aikawa M., Minami M., et al. Plasmodium coatneyi-infected erythrocytes bind to C32 amelanotic melanoma cells under static and flow conditions. J. Vet. Med. Sci. 2003, 65:375-380.
41. Riley P.A., Cooksey C.J., Johnson C.I., Land E.J., Latter A.M., Ramsden C.A. Melanogenesis-targeted anti-melanoma pro-drug development: effect of side-chain variations on the cytotoxicity of tyrosinase-generated ortho-quinones in a model screening system. Eur. J. Cancer 1997, 33:135-143.
42. Kim Y.J. Antimelanogenic and antioxidant properties of gallic acid. Biol. Pharm. Bull. 2007, 30:1052-1055.
43. Liu L., Hudgins W.R., Shack S., Yin M.Q., Samid D. Cinnamic acid: a natural product with potential use in cancer intervention. Int. J. Cancer 1995, 62:345-350.
44. Kuby S.A. Function of NADH(NADPH)-cytochrome c reductase. A Study of Enzymes: Mechanism of Enzyme Action 1990, 693-697. CRC Press, USA. S.A. Kuby (Ed.).
45. Estrela J.M., Ortega A., Obrador E. Glutathione in cancer biology and therapy. Crit. Rev. Clin. Lab. Sci. 2006, 43:143-481.
46. Ortega A.L., Carretero J., Obrador E., Gambini J., Asensi M., Rodilla V., et al. Tumor cytotoxicity by endothelial cells. Impairment of the mitochondrial system for glutathione uptake in mouse B16 melanoma cells that survive after in vitro interaction with the hepatic sinusoidal endothelium. J. Biol. Chem. 2003, 278:13888-13897.
47. Kern D.H., Shoemaker R.H., Hildebrand-Zanki S.U., Driscoll J.S. Structure-activity relationships defining the cytotoxicity of catechol analogues against human malignant melanoma. Cancer Res. 1988, 48:5178-5182.
48. Moridani M.Y., Scobie H., Jamshidzadeh A., Salehi P., O'Brien P.J. Caffeic acid, chlorogenic acid, and dihydrocaffeic acid metabolism: glutathione conjugate formation. Drug Metab. Dispos. 2001, 29:1432-1439.