255
Views
41
CrossRef citations to date
0
Altmetric
Original

Reaction of para-hydroxybenzoic acid esters with singlet oxygen in the presence of glutathione produces glutathione conjugates of hydroquinone, potent inducers of oxidative stress

, , , , &
Pages 233-240 | Received 15 Aug 2005, Published online: 07 Jul 2009

References

  • Soni MG, Taylor SL, Greenberg NA, Burdock GA. Evaluation of the health aspects of methyl paraben: A review of the published literature. Food Chem Toxicol 2002; 40: 1335–1373
  • Soni MG, Burdock GA, Taylor SL, Greenberg NA. Safety assessment of propyl paraben: A review of the published literature. Food Chem Toxicol 2001; 39: 513–532
  • Soni MG, Carabin IG, Burdock GA. Safety assessment of esters of p-hydroxybenzoic acid (parabens). Food Chem Toxicol 2005; 43: 985–1015
  • Farber GA. Prolonged erythema after chemical peel. Dermatol Surg 1998; 24: 934–935
  • Halliwell B, Gutteridge JMC. Free radicals in biology and medicine3rd. Oxford University Press, New York 1999
  • Arakane K, Ryu A, Hayashi C, Masunaga T, Shinmoto K, Mashiko S, Nagano T, Hirobe M. Singlet oxygen (1Δg) generation from coproporphyrin in propionibacterium acnes on irradiation. Biochem Biophys Res Commun 1996; 223: 578–582
  • Yasui H, Sakurai H. Chemiluminescent detection and imaging of reactive oxygen species in live mouse skin exposed to UVA. Biochem Biophys Res Commun 2000; 269: 131–136
  • Takeshita K, Takajo T, Hirata H, Ono M, Utsumi H. In vivo oxygen radical generation in the skin of the protoporphyria model mouse with visible light exposure: An L-band ESR study. J Invest Dermatol 2004; 122: 1463–1470
  • Briviba K, Devasagayam TPA, Sies H, Steenken S. Selective para hydroxylation of phenol and aniline by singlet molecular oxygen. Chem Res Toxicol 1993; 6: 548–553
  • Lau SS, Hill BA, Highet RJ, Monks TJ. Sequential oxidation and glutathione addition to 1,4-benzoquinone: Correlation of toxicity with increased glutathione substitution. Mol Pharmacol 1988; 34: 829–836
  • Wolff SP. Ferrous ion oxidation in presence of ferric ion indicator xylenol orange for measurement of hydroperoxides. Methods Enzymol 1994; 233: 182–189
  • Merkel PB, Kearns DR. Radiationless decay of singlet molecular oxygen in solution. An experimental and theoretical study of electronic-to-vibrational energy transfer. J Am Chem Soc 1972; 94: 7244–7253
  • Murata M, Tsujikawa M, Kawanishi S. Oxidative DNA damage by minor metabolites of toluene may lead to carcinogenesis and reproductive dysfunction. Biochem Biophys Res Commun 1999; 261: 478–483
  • Weber TJ, Huang Q, Monks TJ, Lau SS. Differential regulation of redox responsive transcription factors by the nephrocarcinogen 2,3,5-tris(glutathione-S-yl)hydroquinone. Chem Res Toxicol 2001; 14: 814–821
  • Ramachandiran S, Huang Q, Dong J, Lau SS, Monks TJ. Mitogen-activated protein kinases contribute to reactive oxygen species-induced cell death in renal proximal tubule epithelial cells. Chem Res Toxicol 2002; 15: 1635–1642
  • Finley KT. The addition and substitution chemistry of quinones. The chemistry of the quinonoid compounds, S Patai. John Wiley and Sons, New York 1974; 2: 877–1144
  • Bolton JL, Trush MA, Penning TM, Dryhurst G, Monks TJ. Role of quinones in toxicology. Chem Res Toxicol 2000; 13: 135–160
  • Monks TJ, Lau SS. Commentary: Renal transport processes and glutathione conjugate-mediated nephrotoxicity. Drug Metab Dispos 1987; 15: 437–441
  • Saito I, Kato S, Matsuura T. Photoinduced reactions. XL Addition of singlet oxygen to monocyclic aromatic ring. Tetrahedron Lett 1970; 3: 239–242
  • Thomas MJ, Foote CS. Chemistry of singlet oxygen XXVI. Photooxygenation of phenols. Photochem Photobiol 1978; 27: 683–693
  • Machado AEH, Gomes AJ, Campos CMF, Terrones MGH, Perez DS, Ruggiero R, Castellan A. Photoreactivity of lignin model compounds in the photobleaching of chemical pulps 2. Study of the degradation of 4-hydroxy-3-methoxy-benzaldehyde and two lignin fragments induced by singlet oxygen. J Photochem Photobiol A: Chem 1997; 110: 99–106
  • Kalyanaraman B, Ramanujam S, Singh RJ, Joseph J, Feix JB. Formation of 2,5-dihydroxybenzoic acid during the reaction between singlet oxygen (1O2) and salicylic acid: Analysis by ESR oximetry and HPLC with electrochemical detection. J Am Chem Soc 1993; 115: 4007–4012
  • Gerdes R, Wohrle D, Spiller W, Schneider G, Schnurpfeil G, Schulz-Ekloff G. Photo-oxidation of phenol and monochlorophenols in oxygen-saturated aqueous solutions by different photosensitizers. J Photochem Photobiol A: Chem 1997; 111: 65–74
  • Stücker M, Struk A, Altmeyer P, Herde M, Baumgärtl H, Lübbers DW. The cutaneous uptake of atmospheric oxygen contributes significantly to the oxygen supply of human dermis and epidermis. J Physiol 2002; 538(3)985–994
  • Connor MJ, Wheeler LA. Depletion of cutaneous glutathione by ultraviolet radiation. Photochem Photobiol 1987; 46: 239–245
  • Fuchs J, Zollner TM, Kaufmann R, Podda M. Redox-modulated pathways in inflammatory skin diseases. Free Radic Biol Med 2001; 30: 337–353
  • Sander CS, Chang H, Salzmann S, Muller CSL, Ekanayake-Mudiyanselage S, Elsner P, Thiele JJ. Photoaging is associated with protein oxidation in human skin in vivo. J Invest Dermatol 2002; 118: 618–625

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.