Cancer Letters
Volume 243, Issue 2 , Pages 235-245 , 18 November 2006

Biochemical basis of 4-hydroxyanisole induced cell toxicity towards B16-F0 melanoma cells

Received 20 August 2005 ,Revised 6 October 2005 ,Accepted 27 November 2005.

References 

  1. Riley PA. Hydroxyanisole depigmentation: in vitro studies. J. Pathol. 1969;97:193–206
  2. Naish S, Cooksey CJ, Riley PA. Initial mushroom tyrosinase-catalyzed oxidation product of 4-hydroxyanisole is 4-methoxyorthobenzoquinone. Pigment Cell Res. 1988;1:379–381
  3. Naish S, Holden JL, Cooksey CJ, Riley PA. Major primary cytotoxic product of 4-hydroxyanisole oxidation by mushroom tyrosinase is 4-methoxyorthobenzoquinone. Pigment Cell Res. 1988;1:382–385
  4. Moridani MY, Cheon SS, Khan S, O'Brien PJ. Metabolic activation of 4-hydroxyanisole by isolated rat hepatocytes. Drug Metab. Dispos. 2002;30:1063–1069
  5. Land EJ, Cooksey CJ, Riley PA. Reaction kinetics of 4-methoxy ortho benzoquinone in relation to its mechanism of cytotoxicity: a pulse radiolysis study. Biochem. Pharmacol. 1990;39:1133–1135
  6. Morgan BDG. Recent results of a clinical pilot study of intra-arterial 4-hydroxyanisole chemotherapy in malignant melanoma,. In:  Riley PA editors. Hydroxyanisole: Recent Advances in Anti-Melanoma Therapy. England: IRL Press; 1984;p. 233–241
  7. Moridani MY, Scobie H, Jamshidzadeh A, Salehi P, O'Brien PJ. Caffeic acid, chlorogenic acid, and dihydrocaffeic acid metabolism: glutathione conjugate formation. Drug Metab. Dispos. 2001;29:1432–1439
  8. Sudhar PS, Armstrong DA. Redox potential of some sulfur containing radicals. J. Phys. Chem. 1990;94:5915–5917
  9. Galati G, Chan T, Wu B, O'Brien PJ. Glutathione-dependent generation of reactive oxygen species by the peroxidase-catalyzed redox cycling of flavonoids. Chem. Res. Toxicol. 1999;12:521–525
  10. O'Brien PJ. Radical formation during the peroxidase-catalysed metabolism of carcinogens and xenobiotics: the reactivity of these radicals with GSH, DNA and unsaturated lipid. Free Radic. Biol. Med. 1988;4:169–183
  11. Stoyanovsky DA, Goldman R, Claycamp HG, Kagan VE. Phenoxyl radical-induced thiol-dependent generation of reactive oxygen species: implications for benzene toxicity. Arch. Biochem. Biophys. 1995;317:315–323
  12. Rao R, Fischer V, Mason RP. Glutathione and ascorbate reduction of the acetaminophen radical formed by peroxidase. J. Biol. Chem. 1990;265:844–847
  13. Weis M, Rundgren M, Nelson S, Moldeus P. Peroxidase-catalysed oxidation of 3,5-dimethylacetaminophen causes cell death by selective protein thiol modification in isolated hepatocytes. Chem. Biol. Interact. 1996;100:255–265
  14. Nakamura M, Yamazaki I, Ohtaki S, Nakamura S. Characterisation of one- and two-electron oxidations of glutathione coupled with lactoperoxidase and thyroid peroxidase reactions. J. Biol. Chem. 1986;261:13923–13927
  15. Ellman GL. Tissue sulfhydryl groups. Arch. Biochem. Biophys. 1959;82:70–77
  16. Gergel D, Cederbaum AI. 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
  17. Moridani MY, Moore M, Bartsch RA, 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
  18. 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
  19. Moridani MY, Cheon SS, Khan S, O'Brien P. Metabolic activation of 3-hydroxyanisole by isolated rat hepatocytes. Chem. Biol. Interact. 2003;142:317–333
  20. Preusch PC, Siegel D, Gibson NW, Ross D. A note on the inhibition of DTdiaphorase by dicumarol. Free Radic. Biol. Med. 1991;11:77–80
  21. Khan S, O'Brien PJ. 1-Bromoheptane as a new potent nontoxic glutathione depletory in isolated rat hepatocytes. Biochem. Biophys. Res. Commun. 1991;179:436–441
  22. Siraki AG, O'Brien PJ. Prooxidant activity of free radicals derived from phenol-containing neurotransmitters. Toxicology. 2002;177:81–90
  23. Doherty MD, Cohen GM, Gant TW, Naish S, Riley PA. Metabolism of 1-naphthol by tyrosinase. Biochem. Pharmacol. 1985;34:3167–3172
  24. Naish-Byfield S, Cooksey CJ, Latter AM, Johnson CI, Riley PA. In vitro assessment of the structure-activity relationship of tyrosinase-dependent cytotoxicity of a series of substituted phenols. Melanoma Res. 1991;1:273–287
  25. Moridani MY, Siraki A, O'Brien PJ. Quantitative structure toxicity relationships for phenols in isolated rat hepatocytes. Chem. Biol. Interact. 2003;145:213–223
  26. Moridani MY, Siraki A, Chevaldina T, Scobie H, O'Brien PJ. Quantitative structure toxicity relationships for catechols in isolated rat hepatocytes. Chem. Biol. Interact. 2004;147:297–307
  27. Moridani MY, Galati G, O'Brien PJ. Comparative quantitative structure toxicity relationships for flavonoids evaluated in isolated rat hepatocytes and HeLa tumor cells. Chem. Biol. Interact. 2002;139:251–264

PII: S0304-3835(05)01039-6

doi: 10.1016/j.canlet.2005.11.046

Cancer Letters
Volume 243, Issue 2 , Pages 235-245 , 18 November 2006