메뉴 건너뛰기




Volumn 19, Issue 28, 2012, Pages 4885-4893

Protocatechuic acid alkyl esters: Hydrophobicity as a determinant factor for inhibition of NADPH oxidase

Author keywords

Hydrogen peroxide; Hypochlorous acid; Myeloperoxidase; NADPH oxidase; Neutrophils; Oxidative burst; Peripheral blood mononuclear cells; Protocatechuic acid; Protocatechuic acid alkyl esters; Superoxide anion

Indexed keywords

1,1 DIPHENYL 2 PICRYLHYDRAZYL; BUTYL PROTOCATECHUATE; CARBON; DECYL PROTOCATECHUATE; HEPTYL PROTOCATECHUATE; HYPOCHLOROUS ACID; MYELOPEROXIDASE; OXYGEN; PEROXY RADICAL; PROTOCATECHUIC ACID; PROTOCATECHUIC ACID ALKYL ESTER; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE OXIDASE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE OXIDASE INHIBITOR; SUPEROXIDE; UNCLASSIFIED DRUG;

EID: 84870423567     PISSN: 09298673     EISSN: 1875533X     Source Type: Journal    
DOI: 10.2174/092986712803341557     Document Type: Article
Times cited : (25)

References (46)
  • 3
    • 0038396303 scopus 로고    scopus 로고
    • Correlation of antimutagenic activity and suppression of CYP1A with the lipophilicity of alkyl gallates and other phenolic compounds
    • Feng, Q.; Kumagai, T.; Nakamura, Y.; Uchida, K.; Osawa, T. Correlation of antimutagenic activity and suppression of CYP1A with the lipophilicity of alkyl gallates and other phenolic compounds. Mutat. Res., 2003, 537(1), 101-108.
    • (2003) Mutat. Res. , vol.537 , Issue.1 , pp. 101-108
    • Feng, Q.1    Kumagai, T.2    Nakamura, Y.3    Uchida, K.4    Osawa, T.5
  • 4
    • 1542377352 scopus 로고    scopus 로고
    • Antibacterial activity of akylgallates against Bacillus subtilis
    • Kubo, I.; Fujita, K.; Nihei, K.; Nihei, A. Antibacterial activity of akylgallates against Bacillus subtilis. J. Agric. Food Chem., 2004, 52(5), 1072-1076.
    • (2004) J. Agric. Food Chem. , vol.52 , Issue.5 , pp. 1072-1076
    • Kubo, I.1    Fujita, K.2    Nihei, K.3    Nihei, A.4
  • 6
    • 77952117239 scopus 로고    scopus 로고
    • Inhibitory effect of gallic acid and its esters on 2,2′-azobis(2 amidinopropane)hydrochloride (AAPH)-induced hemolysis and depletion of intracellular glutathione in erythrocytes
    • Ximenes, V.F.; Lopes, M.G.; Petrônio, M.S.; Regasini, L.O.; Silva, D.H.; da Fonseca, L.M. Inhibitory effect of gallic acid and its esters on 2,2′-azobis(2 amidinopropane)hydrochloride (AAPH)-induced hemolysis and depletion of intracellular glutathione in erythrocytes. J. Agric. Food Chem., 2010, 58(9), 5355-5362.
    • (2010) J. Agric. Food Chem. , vol.58 , Issue.9 , pp. 5355-5362
    • Ximenes, V.F.1    Lopes, M.G.2    Petrônio, M.S.3    Regasini, L.O.4    Silva, D.H.5    Da Fonseca, L.M.6
  • 7
    • 15944372262 scopus 로고    scopus 로고
    • And assembly of the NADPH oxidase: A structural perspective
    • Groemping, Y.; Rittinger, K. Activation and assembly of the NADPH oxidase: a structural perspective. Biochem. J., 2005, 386(3), 401-416.
    • (2005) Biochem. J. , vol.386 , Issue.3 , pp. 401-416
    • Groemping, Y.1    Activation, R.K.2
  • 8
    • 65349157681 scopus 로고    scopus 로고
    • Compartmentalization of redox signaling through NADPH oxidase-derived ROS
    • Ushio-Fukai, M. Compartmentalization of redox signaling through NADPH oxidase-derived ROS. Antioxid. Redox Signal, 2009, 11(6), 1289-1299.
    • (2009) Antioxid. Redox Signal , vol.11 , Issue.6 , pp. 1289-1299
    • Ushio-Fukai, M.1
  • 10
    • 84855438807 scopus 로고    scopus 로고
    • Rotenone activates phagocyte NADPH oxidase by binding to its membrane subunit gp91phox
    • Zhou, H.; Zhang, F.; Chen, S.H.; Zhang, D.; Wilson, B.; Hong, J.S.; Gao, H.M. Rotenone activates phagocyte NADPH oxidase by binding to its membrane subunit gp91phox. Free Radic. Biol. Med., 2012, 52(2), 303-313.
    • (2012) Free Radic. Biol. Med. , vol.52 , Issue.2 , pp. 303-313
    • Zhou, H.1    Zhang, F.2    Chen, S.H.3    Zhang, D.4    Wilson, B.5    Hong, J.S.6    Gao, H.M.7
  • 11
    • 84857538385 scopus 로고    scopus 로고
    • NADPH oxidase expression in active multiple sclerosis lesions in relation to oxidative tissue damage and mitochondrial injury
    • Fischer, M.T.; Sharma, R.; Lim, J.L.; Haider, L.; Frischer, J.M.; Drexhage, J.; Mahad, D.; Bradl, M.; van Horssen, J.; Lassmann, H. NADPH oxidase expression in active multiple sclerosis lesions in relation to oxidative tissue damage and mitochondrial injury. Brain, 2012, 135(3), 886-899.
    • (2012) Brain , vol.135 , Issue.3 , pp. 886-899
    • Fischer, M.T.1    Sharma, R.2    Lim, J.L.3    Haider, L.4    Frischer, J.M.5    Drexhage, J.6    Mahad, D.7    Bradl, M.8    Van Horssen, J.9    Lassmann, H.10
  • 12
    • 84859220356 scopus 로고    scopus 로고
    • NADPH oxidase is involved in H2O2-induced differentiation of human promyelocyticleukaemia HL-60 cells
    • Lin, C.; Wang, H. NADPH oxidase is involved in H2O2-induced differentiation of human promyelocyticleukaemia HL-60 cells. Cell Biol. Int., 2012, 36(4), 391-395.
    • (2012) Cell Biol. Int. , vol.36 , Issue.4 , pp. 391-395
    • Lin, C.1    Wang, H.2
  • 13
    • 84857550948 scopus 로고    scopus 로고
    • The Nox family of NADPH oxidases: Friend or foe of the vascular system?
    • Takac, I.; Schröder, K.; Brandes, R.P. The Nox family of NADPH oxidases: friend or foe of the vascular system? Curr. Hypertens. Rep., 2012, 14(1), 70-78.
    • (2012) Curr. Hypertens. Rep. , vol.14 , Issue.1 , pp. 70-78
    • Takac, I.1    Schröder, K.2    Brandes, R.P.3
  • 14
    • 79957890939 scopus 로고    scopus 로고
    • Combating oxidative stress in vascular disease: NADPH oxidases as therapeutic targets
    • Drummond, G.R.; Selemidis, S.; Griendling, K.K.; Sobey, C.G. Combating oxidative stress in vascular disease: NADPH oxidases as therapeutic targets. Nat. Rev. Drug Discov., 2011, 10(6), 453-471.
    • (2011) Nat. Rev. Drug Discov. , vol.10 , Issue.6 , pp. 453-471
    • Drummond, G.R.1    Selemidis, S.2    Griendling, K.K.3    Sobey, C.G.4
  • 16
    • 38549156600 scopus 로고    scopus 로고
    • Apocynin NADPH oxidase, and vascular cells: A complex matter
    • Touyz, R.M. Apocynin, NADPH oxidase, and vascular cells: a complex matter. Hypertension, 2008,51(2), 172-174.
    • (2008) Hypertension , vol.51 , Issue.2 , pp. 172-174
    • Touyz, R.M.1
  • 19
    • 84858956376 scopus 로고    scopus 로고
    • Scavenging of NADPH oxidase-derived superoxide anions improves depressed baroreflex sensitivity in spontaneously hypertensive rats
    • Guimarães, D.D.; Carvalho, C.C.; Braga, V.A. Scavenging of NADPH Oxidase-derived Superoxide Anions Improves Depressed Baroreflex Sensitivity in Spontaneously Hypertensive Rats. Clin Exp Pharmacol. Physiol., 2012, 1440-1681.
    • (2012) Clin Exp Pharmacol. Physiol. , pp. 1440-1681
    • Guimarães, D.D.1    Carvalho, C.C.2    Braga, V.A.3
  • 20
    • 84855555390 scopus 로고    scopus 로고
    • Protective effect of apocynin, a NADPH-oxidase inhibitor, against contrast-induced nephropathy in the diabetic rats: A comparison with N-acetylcysteine
    • Ahmad, A.; Mondello, S.; Di Paola, R.; Mazzon, E.; Esposito, E.; Catania, M.A.; Italiano, D.; Mondello, P.; Aloisi, C.; Cuzzocrea, S. Protective effect of apocynin, a NADPH-oxidase inhibitor, against contrast-induced nephropathy in the diabetic rats: a comparison with N-acetylcysteine. Eur. J. Pharmacol., 2012, 674(2-3), 397-406.
    • (2012) Eur. J. Pharmacol. , vol.674 , Issue.2-3 , pp. 397-406
    • Ahmad, A.1    Mondello, S.2    Di Paola, R.3    Mazzon, E.4    Esposito, E.5    Catania, M.A.6    Italiano, D.7    Mondello, P.8    Aloisi, C.9    Cuzzocrea, S.10
  • 21
    • 78651267346 scopus 로고    scopus 로고
    • Effect of Apocynin, an inhibitor of NADPH oxidase, in the inflammatory process induced by an experimental model of spinal cord injury
    • Impellizzeri, D.; Mazzon, E.; Esposito, E.; Paterniti, I.; Bramanti, P.; Cuzzocrea, S. Effect of Apocynin, an inhibitor of NADPH oxidase, in the inflammatory process induced by an experimental model of spinal cord injury. Free Radic. Res., 2011, 45(2), 221-236.
    • (2011) Free Radic. Res. , vol.45 , Issue.2 , pp. 221-236
    • Impellizzeri, D.1    Mazzon, E.2    Esposito, E.3    Paterniti, I.4    Bramanti, P.5    Cuzzocrea, S.6
  • 23
    • 0036365787 scopus 로고    scopus 로고
    • A comparison of whole blood neutrophil chemiluminescence measured with cuvette and microtitre plate luminometers
    • Lojek, A.; Kubala, L.; CÍZOVÁ, H.; CÍZ, M. A comparison of whole blood neutrophil chemiluminescence measured with cuvette and microtitre plate luminometers. Luminescence, 2002, 17(1) 1-4.
    • (2002) Luminescence , vol.17 , Issue.1 , pp. 1-4
    • Lojek, A.1    Kubala, L.2    Cízová, H.3    Cíz, M.4
  • 24
    • 0023289451 scopus 로고
    • Atomic physicochemical parameters for threedimensional-structure-directed quantitative structureactivity relationships. 2. Modeling dispersive and hydrophobic interactions
    • Ghose, A.K.; Crippen, G.M. Atomic physicochemical parameters for threedimensional-structure-directed quantitative structureactivity relationships. 2. Modeling dispersive and hydrophobic interactions. J. Chem. Inf. Comput. Sci., 1987, 27, 21-35.
    • (1987) J. Chem. Inf. Comput. Sci. , vol.27 , pp. 21-35
    • Ghose, A.K.1    Crippen, G.M.2
  • 26
    • 4944250546 scopus 로고    scopus 로고
    • A pyranine based procedure for evaluation of the total antioxidant potential (TRAP) of polyphenols. A comparison with closely related methodologies
    • Campos, A.M.; Sotomayor, C.P.; Pino, E.; Lissi, E. A pyranine based procedure for evaluation of the total antioxidant potential (TRAP) of polyphenols. A comparison with closely related methodologies. Biol. Res., 2004, 37, 287-292.
    • (2004) Biol. Res. , vol.37 , pp. 287-292
    • Campos, A.M.1    Sotomayor, C.P.2    Pino, E.3    Lissi, E.4
  • 27
    • 0016178453 scopus 로고
    • Single-step separation of red blood cells. Granulocytes and mononuclear leukocytes on discontinuous density gradients of Ficoll-Hypaque
    • English, D.; Andersen, B.R. Single-step separation of red blood cells. Granulocytes and mononuclear leukocytes on discontinuous density gradients of Ficoll-Hypaque. J. Immunol. Methods, 1974, 5(3), 249-252.
    • (1974) J. Immunol. Methods , vol.5 , Issue.3 , pp. 249-252
    • English, D.1    Andersen, B.R.2
  • 28
    • 51149102710 scopus 로고    scopus 로고
    • Trypan blue exclusion test of cell viability
    • Appendix 3:Appendix 3B
    • Strober, W. Trypan blue exclusion test of cell viability. Curr. Protoc. Immunol., Appendix 3:Appendix 3B, 2001.
    • (2001) Curr. Protoc. Immunol.
    • Strober, W.1
  • 29
    • 79956158020 scopus 로고    scopus 로고
    • 4-fluoro-2-methoxyphenol, an apocynin analog with enhanced inhibitory effect on leukocyte oxidant production and phagocytosis
    • de Almeida, A.C.; Marques, O.C.; Arslanian, C.; Condino-Neto, A.; Ximenes, V.F. 4-fluoro-2-methoxyphenol, an apocynin analog with enhanced inhibitory effect on leukocyte oxidant production and phagocytosis. Eur. J. Pharmacol., 2011, 660(2-3), 445-453.
    • (2011) Eur. J. Pharmacol. , vol.660 , Issue.2-3 , pp. 445-453
    • De Almeida, A.C.1    Marques, O.C.2    Arslanian, C.3    Condino-Neto, A.4    Ximenes, V.F.5
  • 30
    • 0034697387 scopus 로고    scopus 로고
    • Superoxide produced by activated neutrophils efficiently reduces the tetrazolium salt, WST-1 to produce a soluble formazan: A simple colorimetric assay for measuring respiratory burst activation and for screening anti-inflammatory agents
    • Tan, A.S.; Berridge, M.V. Superoxide produced by activated neutrophils efficiently reduces the tetrazolium salt, WST-1 to produce a soluble formazan: a simple colorimetric assay for measuring respiratory burst activation and for screening anti-inflammatory agents. J. Immunol. Methods, 2000, 238(1-2), 59-68.
    • (2000) J. Immunol. Methods , vol.238 , Issue.1-2 , pp. 59-68
    • Tan, A.S.1    Berridge, M.V.2
  • 31
    • 72449125795 scopus 로고    scopus 로고
    • Serotonin as a physiological substrate for myeloperoxidase and its superoxide-dependent oxidation to cytotoxic tryptamine-4,5-dione
    • Ximenes, V.F.; Maghzal, G.J.; Turner, R.; Kato, Y.; Winterbourn, C.C.; Kettle, A.J. Serotonin as a physiological substrate for myeloperoxidase and its superoxide-dependent oxidation to cytotoxic tryptamine-4,5-dione. Biochem J., 2009, 425(1), 285-293.
    • (2009) Biochem J. , vol.425 , Issue.1 , pp. 285-293
    • Ximenes, V.F.1    Maghzal, G.J.2    Turner, R.3    Kato, Y.4    Winterbourn, C.C.5    Kettle, A.J.6
  • 32
    • 0025082043 scopus 로고
    • Free radical initiators as source of water- or lipid-soluble peroxyl radicals
    • Niki, E. Free radical initiators as source of water- or lipid-soluble peroxyl radicals. Methods Enzymol., 1990, 186, 100-108.
    • (1990) Methods Enzymol. , vol.186 , pp. 100-108
    • Niki, E.1
  • 35
    • 0017850071 scopus 로고
    • The effect of phorbol myristate acetate on the metabolism and ultrastructure of human alveolar macrophage
    • Hoidal, J.R.; Repine, J.E.; Beall, G.D.; Rasp, F.L. Jr.; White, J.G. The Effect of Phorbol Myristate Acetate on the Metabolism and Ultrastructure of Human Alveolar Macrophage. Am. J. Pathol., 1978, 91(3), 469-482.
    • (1978) . Am. J. Pathol. , vol.91 , Issue.3 , pp. 469-482
    • Hoidal, J.R.1    Repine, J.E.2    Beall, G.D.3    Rasp Jr., F.L.4    White, J.G.5
  • 37
    • 33746866753 scopus 로고    scopus 로고
    • DPPH (=22-Diphenyl-1-picrylhydrazyl) radical-scavenging reaction of protocatechuic acid (=3,4-dihydroxybenzoic acid): Difference in reactivity between acids and their esters
    • Saito, S.; Kawabata, J. DPPH (=2,2-Diphenyl-1-picrylhydrazyl) Radical-Scavenging Reaction of Protocatechuic Acid (=3,4-Dihydroxybenzoic Acid): Difference in Reactivity between Acids and Their Esters. Helvetica Chimica Acta, 2006, 89(7), 1395-1407.
    • (2006) Helvetica Chimica Acta , vol.89 , Issue.7 , pp. 1395-1407
    • Saito, S.1    Kawabata, J.2
  • 38
    • 77953145782 scopus 로고    scopus 로고
    • Structure-property-activity relationship of phenolic acids and derivatives. Protocatechuic acid alkyl esters
    • Reis, B.; Martins, M.; Barreto, B.; Milhazes, N.; Garrido, E.M.; Silva, P.; Garrido, J.; Borge, F. Structure-property-activity relationship of phenolic acids and derivatives. Protocatechuic acid alkyl esters. J. Agric. Food Chem., 2010, 58(11), 6986-6993.
    • (2010) J. Agric. Food Chem. , vol.58 , Issue.11 , pp. 6986-6993
    • Reis, B.1    Martins, M.2    Barreto, B.3    Milhazes, N.4    Garrido, E.M.5    Silva, P.6    Garrido, J.7    Borge, F.8
  • 39
    • 84856717179 scopus 로고    scopus 로고
    • Trimerhydroxylatedquinone derived from apocynin targets cysteine residues of p47phox preventing the activation of human vascular NADPH oxidase
    • Mora-Pale, M.; Kwon, S.J.; Linhardt, R.J.; Dordick, J.S. Trimerhydroxylatedquinone derived from apocynin targets cysteine residues of p47phox preventing the activation of human vascular NADPH oxidase. Free Radic. Biol. Med., 2012, 52(5), 962-969.
    • (2012) Free Radic. Biol. Med. , vol.52 , Issue.5 , pp. 962-969
    • Mora-Pale, M.1    Kwon, S.J.2    Linhardt, R.J.3    Dordick, J.S.4
  • 41
    • 79952133271 scopus 로고    scopus 로고
    • Lipid oxidation by hypochlorous acid: Chlorinated lipids in atherosclerosis and myocardial ischemia
    • Ford, D.A. Lipid oxidation by hypochlorous acid: chlorinated lipids in atherosclerosis and myocardial ischemia. Clin. Lipidol., 2010, 5(6), 835-852.
    • (2010) Clin. Lipidol. , vol.5 , Issue.6 , pp. 835-852
    • Ford, D.A.1
  • 43
    • 37549011857 scopus 로고    scopus 로고
    • Mono-O-methylated flavanols and other flavonoids as inhibitors of endothelial NADPH oxidase
    • Steffen, Y.; Gruber, C.; Schewe, T.; Sies, H. Mono-O-methylated flavanols and other flavonoids as inhibitors of endothelial NADPH oxidase. Arch. Biochem. Biophys., 2008, 469(2), 209-219.
    • (2008) Arch. Biochem. Biophys. , vol.469 , Issue.2 , pp. 209-219
    • Steffen, Y.1    Gruber, C.2    Schewe, T.3    Sies, H.4
  • 44
    • 80955135026 scopus 로고    scopus 로고
    • Administration of rosmarinic acid reduces cardiopathology and blood pressure through inhibition of p22phox NADPH oxidase in fructose-fed hypertensive rats
    • Karthik, D.; Viswanathan, P.; Anuradha, C.V. Administration of rosmarinic acid reduces cardiopathology and blood pressure through inhibition of p22phox NADPH oxidase in fructose-fed hypertensive rats. Cardiovasc. Pharmacol., 2011, 58(5), 514-521.
    • (2011) Cardiovasc. Pharmacol. , vol.58 , Issue.5 , pp. 514-521
    • Karthik, D.1    Viswanathan, P.2    Anuradha, C.V.3
  • 45
    • 34250720665 scopus 로고    scopus 로고
    • The reactivity of ortho-methoxy-substituted catechol radicals with sulfhydryl groups: Contribution for the comprehension of the mechanism of inhibition of NADPH oxidase by apocynin
    • Kanegae, M.P.; da Fonseca, L.M.; Brunetti, I.L.; Silva, S.O.; Ximenes, V.F. The reactivity of ortho-methoxy-substituted catechol radicals with sulfhydryl groups: contribution for the comprehension of the mechanism of inhibition of NADPH oxidase by apocynin. Biochem. Pharmacol., 2007, 74(3), 457-464.
    • (2007) Biochem. Pharmacol. , vol.74 , Issue.3 , pp. 457-464
    • Kanegae, M.P.1    Da Fonseca, L.M.2    Brunetti, I.L.3    Silva, S.O.4    Ximenes, V.F.5
  • 46
    • 0025783709 scopus 로고
    • The use of diphenyleneiodonium and its analogues to investigate the role of the NADPH oxidase in the tumoricidal activity of macrophages in vitro
    • Hancock, J.T.; White, J.I.; Jones, O.T.; Silver, I.A. The use of diphenyleneiodonium and its analogues to investigate the role of the NADPH oxidase in the tumoricidal activity of macrophages in vitro. Free Radic. Biol. Med., 1991, 11(1), 25-29.
    • (1991) Free Radic. Biol. Med. , vol.11 , Issue.1 , pp. 25-29
    • Hancock, J.T.1    White, J.I.2    Jones, O.T.3    Silver, I.A.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.