298
Views
7
CrossRef citations to date
0
Altmetric
Original Articles

HPLC study on Fenton-reaction initiated oxidation of salicylic acid. Biological relevance of the reaction in intestinal biotransformation of salicylic acid

, , , , & ORCID Icon
Pages 1040-1051 | Received 15 Jun 2018, Accepted 21 Aug 2018, Published online: 12 Oct 2018

References

  • Essman WB, Wollman SB. Free radicals, central nervous system processes and brain functions. In: Das DK, Essman WB, editors. Oxygen radicals: systemic events and disease processes. Basel: Karger; 1990. p. 172–192.
  • Favier AE. How to demonstrate the occurrence of an oxidative stress in human? In: Favier AE, Cadet J, Kalyanaraman B, et al., editor. Analysis of free radicals in biological systems. Basel: Birkhauser Verlag; 1995. p. 99–117.
  • Sies H, editor. Antioxidants in disease mechanisms and therapy. vol 38. Adv Pharmacol. San Diego: Academic Press. 1997 p. 425–675.
  • Ziech D, Franco R, Georgakilas AG, et al. The role of reactive oxygen species and oxidative stress in environmental carcinogenesis and biomarker development. Chem Biol Interact. 2010;188(2):334–339.
  • Ghiselli A, Laurenti O, de Mattia G, et al. Salicylate hydroxylation as an early marker of in vivo oxidative stress in diabetic patients. Free Radic Biol Med. 1992;13(6):621–626.
  • Hiller KO, Hodd PL, Willson RL. Antiinflammatory drugs: protection of a bacterial virus as an in vitro biological measure of free radical activity. Chem Biol Interact. 1983;47(3):293–305.
  • Halliwell B, Kaur H, Ingelman-Sundberg M. Hydroxylation of salicylate as an assay for hydroxyl radicals: a cautionary note. Free Radic Biol Med. 1991;10(6):439–441.
  • Schrör K Acetylsalicylic acid. Weinheim: Wiley-VCH Press; 2009.
  • Mays DC, Sharp DE, Beach CA, et al. Improved method for the determination of aspirin and its metabolites in biological fluids by high-performance liquid chromatography: applications to human and animal studies. J Chromatogr. 1984;311(2):301–309.
  • Hutt AJ, Caldwell J, Smith RL. The metabolism of aspirin in man: a population study. Xenobiotica 1986;16(3):239–249.
  • Reidl U. Determination of acetylsalicylic acid and metabolites in biological fluids by high-performance liquid chromatography. J Chromatogr. 1983;272(2):325–331.
  • Grootveld M, Halliwell B. Aromatic hydroxylation as a potential measure of hydroxyl-radical formation in vivo. Identification of hydroxylated derivatives of salicylate in human body fluids. Biochem J. 1986;237(2):499–504.
  • Grootveld M, Halliwell B. 2,3-Dihydroxybenzoic acid is a product of human aspirin metabolism. Biochem Pharmacol. 1988;37(2):271–280.
  • Coudray C, Talla M, Martin S, et al. High-performance liquid chromatography-electrochemical determination of salicylate hydroxylation products as an in vivo marker of oxidative stress. Anal Biochem. 1995;227(1):101–111.
  • Ingelman-Sundberg M, Kaur H, Terelius Y, et al. Hydroxylation of salicylate by microsomal fractions and cytochrome P-450. Lack of production of 2,3-dihydroxybenzoate unless hydroxyl radical formation is permitted. Biochem J. 1991;276(3):753–757.
  • Kuzma M, Nyúl E, Mayer M, et al. HPLC analysis of in vivo intestinal absorption and oxidative metabolism of salicylic acid in the rat. Biomed Chromatogr. 2016;30(12):2044–2052.
  • Asmat U, Abad K, Ismail K. Diabetes mellitus and oxidative stress – a concise review. Saudi Pharm J. 2016;24(5):547–553.
  • Neyens E, Baeyens J. A review of classic Fenton’s peroxidation as an advanced oxidation technique. J Hazard Mater. 2003;98(1–3):33–50.
  • Kremer ML. Mechanism of the Fenton reaction. Evidence for a new intermediate. Phys Chem Chem Phys. 1999;1(15):3595–3605.
  • Nichela DA, Donadelli JA, Caram BF, et al. Iron cycling during the autocatalytic decomposition of benzoic acid derivatives by Fenton-like and photo-Fenton techniques. Appl Catal B Environ. 2015;170–171:312–321.
  • Arnold SM, Hickey WJ, Harris RF. Degradation of atrazine by Fenton’s reagent: condition optimisation and product quantification. Environ Sci Technol. 1995;29(8):2083–2089.
  • Oktavia B, Lim LW, Takeuchi T. Simultaneous determination of Fe(III) and Fe(II) ions via complexation with salicylic acid and 1,10-phenanthroline in microcolumn ion chromatography. Anal Sci. 2008;24(11):1487–1492.
  • Waqar D, Hussein W. Kinetics and mechanism of reduction of Fe(III) salicylate complex by hydroquinone. Pak J Pharm Sci. 2011;24(1):31–35.
  • Barbusiński K, Filipek K. Use of Fenton’s reagent for removal of pesticides from industrial wastewater. Pol J Environ Stud 2001;10:207–212.
  • Richmond R, Halliwell B, Chauhan J, et al. Superoxide-dependent formation of hydroxyl radicals: detection of hydroxyl radicals by the hydroxylation of aromatic compounds. Anal Biochem. 1981;118(2):328–335.
  • Luo X, Lehotay DC. Determination of hydroxyl radicals using salicylate as a trapping agent by gas chromatography-mass spectrometry. Clin Biochem. 1997;30(1):41–46.
  • Nguyen V, Bonds DV, Prokai L. Measurement of hydroxyl-radical formation in the rat striatum by in vivo microdialysis and GC-MS. Chromatographia. 2008;68(Suppl 1):s57–ss62.
  • Bakar SK, Niazi S. High-performance liquid chromatographic determination of aspirin and its metabolites in plasma and urine. J Pharm Sci. 1983;72(9):1020–1023.
  • O’Kruk RJ, Adams MA, Philp RB. Rapid and sensitive determination of acetylsalicylic acid and its metabolites using reversed-phase high-performance liquid chromatography. J Chromatogr. 1984;310(2):343–352.
  • Coudray C, Mangournet C, Bouhadjeb S, et al. Rapid high-performance liquid chromatographic assay for salicylic acid in plasma without solvent extraction. J Chromatogr Sci. 1996;34(4):166–173.
  • Yamamoto E, Takakuwa S, Kato T, et al. Sensitive determination of aspirin and its metabolites in plasma by LC-UV using on-line solid-phase extraction with methylcellulose-immobilized anion-exchange restricted access media. J Chromatogr B Analyt Technol Biomed Life Sci. 2007;846(1–2):132–138.
  • Bektaşoğlu B, Özyürek M, Güçlü K, et al. Hydroxyl radical detection with a salicylate probe using modified CUPRAC spectrophotometry and HPLC. Talanta. 2008;77(1):90–97.
  • Panchompoo J, Aldous L, Kabeshov M, et al. A green approach to Fenton chemistry: mono-hydroxylation of salicylic acid in aqueous medium by the electrogeneration of Fenton’s reagent. New J Chem. 2012;36(5):1265–1272.
  • Walling C. Fenton’s reagent revisited. Acc Chem Res. 1975;8(4):125–131.
  • Bojcsev S, Almási A, Simon H, et al. Investigation of drug metabolism in various segments of small intestine in the rat. Acta Physiol Hung. 2013;100(1):115–123.
  • Grant RD, Rizzardo E, Solomon DH. Reactions of hydroxyl radicals with polymerizable olefins. J Chem Soc, Perkin Trans 2. 1985;II(3):379–384.
  • Prousek J. Fenton chemistry in biology and medicine. Pure Appl Chem. 2007;79(12):2325–2338.
  • Cheng IF, Zhao CP, Amolins A, et al. A hypothesis for thein vivo antioxidant action of salicyclic acid. Biometals. 1996;9(3):285–290.
  • Barbusinski K. Fenton reaction controversy concerning the chemistry. Ecol Chem Eng S. 2009;16:347–358.
  • Graziano JH, Grady RW, Cerami A. The identification of 2, 3-dihydroxybenzoic acid as a potentially useful iron-chelating drug. J Pharmacol Exp Ther. 1974;190(3):570–575.
  • Exner M, Hermann M, Hofbauer R, et al. The salicylate metabolite gentisic acid, but not the parent drug, inhibits glucose autoxidation-mediated atherogenic modification of low density lipoprotein. FEBS Lett. 2000;470(1):47–50.
  • Fukui A, Naito Y, Handa O, et al. Acetyl salicylic acid induces damage to intestinal epithelial cells by oxidation-related modifications of ZO-1. Am J Physiol Gastrointest Liver Physiol. 2012;303(8):G927–G936.
  • Smecuol E, Pinto Sanchez MI, Suarez A, et al. Low-dose aspirin affects the small bowel mucosa: results of a pilot study with a multidimensional assessment. Clin Gastroenterol Hepatol. 2009;7(5):524–529.
  • Liu Y, Hunt CA. Studies of intestinal drug transport using an in silico epithelio-mimetic device. Biosystems. 2005;82(2):154–167.
  • Mitschke D, Reichel A, Fricker G, et al. Characterization of cytochrome P450 protein expression along the entire length of the intestine of male and female rats. Drug Metab Dispos. 2008;36(6):1039–1045.
  • Bojić M, Sedgeman CA, Nagy LD, et al. Aromatic hydroxylation of salicylic acid and aspirin by human cytochromes P450. Eur J Pharm Sci. 2015;73:49–56.
  • Brandes RP, Weissmann N, Schröder K. NADPH oxidases in cardiovascular disease. Free Radic Biol Med. 2010;49(5):687–706.
  • Brandes RP, Weissmann N, Schröder K. Nox family NADPH oxidases: molecular mechanisms of activation. Free Radic Biol Med. 2014;76:208–226.
  • Halliwell B, Grootveld M. The measurement of free radical reactions in humans. Some thoughts for future experimentation. FEBS Lett. 1987;213(1):9–14.

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.