Abstract
A novel spectrofluorometric method, using 2-(2-pyridyliminomethyl)phenol as a fluorescent probe, was developed for the determination of superoxide anion radical (O2 •−) and superoxide dismutase activity (SOD). The new fluorescent probe was synthesized and characterized with elemental analysis and IR spectra. It was oxidized by O2 •− to form a less fluorescence product. Based on this reaction, a spectrofluorometric method was proposed and successfully used to determine superoxide anion radicals and SOD activity. The effects of interferences were studied. The reaction was simple, precise and sensitive. It was applied to determine SOD activity in garlic, papaya and spinach successfully.
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Keaney JJF, Vita JA (1995) Atherosclerosis, oxidative stress, and antioxidant protection in endothelium-derived relaxing factor action. Prog Cardiovasc Dis 38(2):129–154. doi:10.1016/S0033-0620(05)80003-9
Ali S, Choudhary MI, Rahman AU (2008) Superoxide anion radical, an important target for the discovery of antioxidants. Atheroscler Suppl 9(1):268. doi:10.1016/S1567-5688(08)71081-X
McCabe DR, Maher TJ, Acworth IN (1997) Improved method for the estimation of hydroxyl free radical levels in vivo based on liquid chromatography with electrochemical detection. J Chromatogr B Analyt Technol Biomed Life Sci 691:23–32. doi:10.1016/S0378-4347(96)00416-1
Cao SL, Zhan HY, Fu SY, Chen LH (2007) Regulation of superoxide anion radical during the oxygen delignification process. Chin J Chem Eng 15(1):132–137. doi:10.1016/S1004-9541(07)60046-9
Lonneke CW, Jos CSK, Edwin JCM, Jacob JB (2008) Discriminative protection against hydroxyl and superoxide anion radicals by quercetin in human leucocytes in vitro. Toxicol In Vitro 22(2):301–307. doi:10.1016/j.tiv.2007.09.002
Tang B, Zhang L, Hu JX, Li P, Zhang H, Zhao YX (2004) Indirect determination of superoxide anion radical in the plant of red sage based on vanillin-8-aminoquinoline with fluorescence. Anal Chim Acta 502(1):125–131. doi:10.1016/j.aca.2003.09.052
Herath AMC, Gamini Rajapakse RM, Karunarathne V, Wicramasinghe A (2006) Electrochemical investigation of superoxide anion scavenging ability of 1,2,3-triketohydrindene hydrate in aprotic solvents. Electrochim Acta 51(14):2890–2897. doi:10.1016/j.electacta.2005.03.094
Er TK, Tsai SM, Wu SH, Chiang W, Lin HC, Lin SF, Wu SH, Tsai LY, Liu TZ (2007) Antioxidant status and superoxide anion radical generation in acute myeloid leukemia. Clin Biochem 40(13–14):1015–1019. doi:10.1016/j.clinbiochem.2007.05.013
Beauchamp C, Fridovich I (1971) Superoxide dismutase: improved assays and an assay applicable to acrylamide gels. Anal Biochem 44(1):276–287. doi:10.1016/0003-2697(71)90370-8
Martínez R (2007) Effects of ultraviolet radiation on protein content, respiratory electron transport system (ETS) activity and superoxide dismutase (SOD) activity of Antarctic plankton. Polar Biol 30:1159–1172. doi:10.1007/s00300-007-0273-3
Lenaerts I, Braeckman BP, Matthijssens F, Vanfleteren JR (2002) A high-throughput microtiter plate assay for superoxide dismutase based on lucigenin chemiluminescence. Anal Biochem 311(1):90–92. doi:10.1016/S0003-2697(02)00397-4
Gao RM, Yuan ZB, Zhao ZQ, Gao XR (1998) Mechanism of pyrogallol autoxidation and determination of superoxide dismutase enzyme activity. Bioelectrochem Bioenerg 45(1):41–45. doi:10.1016/S0302-4598(98)00072-5
Shirakawa E, Yoshida H, Takaya H (1997) An iminophosphine-palladium catalyst for cross-coupling of aryl halides with organostannanes. Tetrahedron Lett 38(21):3759–3762. doi:10.1016/S0040-4039(97)00747-8
Zhang ZJ (2003) Synthesis and characterization of heterocyclic Schiff base containing nitrogen. J Jinzhou Norm Coll 24(4):51–52
Tang B, Zhang L, Zhang LL (2004) Study and application of flow injection spectrofluorimetry with a fluorescent probe of 2-(2-pyridil)-benzothiazoline for superoxide anion radicals. Anal Biochem 326(2):176–182. doi:10.1016/j.ab.2003.11.023
Yuan ZB, Gao RM (1997) Kinetics and mechanism of pyrogallol autoxidation. Chem J Chin Univ 18(9):1438–1441
Magnani L, Gaydou EM, Hubaud JC (2000) Spectrophotometric measurement of antioxidant properties of flavones and flavonols against superoxide anion. Anal Chim Acta 411(1–2):209–216. doi:10.1016/S0003-2670(00)00717-0
Brik ME (1995) Oxidation of secondary amines to nitroxides with oxone in aqueous buffered solution. Tetrahedron Lett 36(31):5519–5522
Rozantzev EG, Krinitzkaya LA (1965) Free iminoxyl radicals in the hydrogenated pyrrole series. Tetrahedron 21(2):491–497. doi:10.1016/S0040-4020(01)82219-5
Xu SH, Hang H, Li YP (2001) Study and improvement on the pyrogallol autoxidation assay method for SOD activity assay. Chemistry (Easton) 64(8):516–519
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Ma, S., Mu, W., Gao, J. et al. Spectroscopic Study of 2-(2-pyridyliminomethyl)phenol as a Novel Fluorescent Probe for Superoxide Anion Radicals and Superoxide Dismutase Activity. J Fluoresc 19, 487–493 (2009). https://doi.org/10.1007/s10895-008-0437-8
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DOI: https://doi.org/10.1007/s10895-008-0437-8