메뉴 건너뛰기




Volumn 19, Issue 11, 2013, Pages 1257-1265

Nitro-fatty acids: Formation, redox signaling, and therapeutic potential

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA SYNUCLEIN; ANGIOTENSIN 1 RECEPTOR; ANTIINFLAMMATORY AGENT; ANTIOXIDANT; APOLIPOPROTEIN; ARACHIDONIC ACID; FATTY ACID; GLYCERALDEHYDE 3 PHOSPHATE; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; INDUCIBLE NITRIC OXIDE SYNTHASE; INTERCELLULAR ADHESION MOLECULE 1; KELCH LIKE ECH ASSOCIATED PROTEIN 1; LIPOPROTEIN; MONOCYTE CHEMOTACTIC PROTEIN 1; NITRIC OXIDE; NITROGEN DIOXIDE; NITROGEN OXIDE; OXIDOREDUCTASE; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR ALPHA; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR DELTA; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR GAMMA; PEROXYNITRITE; PEROXYNITROUS ACID; PROSTAGLANDIN SYNTHASE; PROTEIN KINASE C; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE OXIDASE; TRANSCRIPTION FACTOR NRF2; UNCOUPLING PROTEIN 2; UNSATURATED FATTY ACID; VASCULAR CELL ADHESION MOLECULE 1;

EID: 84884753555     PISSN: 15230864     EISSN: 15577716     Source Type: Journal    
DOI: 10.1089/ars.2012.5023     Document Type: Review
Times cited : (45)

References (73)
  • 1
    • 33746882132 scopus 로고    scopus 로고
    • Modulation of nitrated lipid signaling by multidrug resistance protein 1 (MRP1): Glutathione conjugation and MRP1-mediated efflux inhibit nitrolinoleic acid-induced, PPARγ-dependent transcription activation
    • DOI 10.1021/bi0605639
    • Alexander RL, Bates DJ, Wright MW, King SB, and Morrow CS. Modulation of nitrated lipid signaling by multidrug resistance protein 1 (MRP1): glutathione conjugation and mrp1-mediated efflux inhibit nitrolinoleic acid-induced, ppargamma-dependent transcription activation. Biochemistry 45: 7889-7896, 2006. (Pubitemid 44185506)
    • (2006) Biochemistry , vol.45 , Issue.25 , pp. 7889-7896
    • Alexander, R.L.1    Bates, D.J.P.2    Wright, M.W.3    King, S.B.4    Morrow, C.S.5
  • 2
    • 0036437097 scopus 로고    scopus 로고
    • Peroxynitrite formation from biochemical and cellular fluxes of nitric oxide and superoxide
    • DOI 10.1016/S0076-6879(02)59198-9
    • Alvarez MN, Trujillo M, and Radi R. Peroxynitrite formation from biochemical and cellular fluxes of nitric oxide and superoxide. Methods Enzymol 359: 353-366, 2002. (Pubitemid 35387036)
    • (2002) Methods in Enzymology , vol.359 , pp. 353-366
    • Alvarez, M.N.1    Trujillo, M.2    Radi, R.3
  • 6
    • 2942595951 scopus 로고    scopus 로고
    • Biological nitration of arachidonic acid
    • DOI 10.2174/1570161043476465
    • Balazy M and Poff CD. Biological nitration of arachidonic acid. Curr Vasc Pharmacol 2: 81-93, 2004. (Pubitemid 38855017)
    • (2004) Current Vascular Pharmacology , vol.2 , Issue.1 , pp. 81-93
    • Balazy, M.1    Poff, C.D.2
  • 9
    • 23044495623 scopus 로고    scopus 로고
    • Reactivity of peroxynitrite and nitric oxide with LDL
    • DOI 10.1080/15216540500137701
    • Botti H, Trostchansky A, Batthyany C, and Rubbo H. Reactivity of peroxynitrite and nitric oxide with LDL. IUBMB Life 57: 407-412, 2005. (Pubitemid 41073122)
    • (2005) IUBMB Life , vol.57 , Issue.6 , pp. 407-412
    • Botti, H.1    Trostchansky, A.2    Batthyany, C.3    Rubbo, H.4
  • 10
    • 0347753275 scopus 로고    scopus 로고
    • Regulation of superoxide anion production by NADPH oxidase in monocytes/macrophages: Contributions to atherosclerosis
    • DOI 10.1161/01.ATV.0000097769.47306.12
    • Cathcart MK. Regulation of superoxide anion production by NADPHoxidase inmonocytes/macrophages: contributions to atherosclerosis. Arterioscler Thromb Vasc Biol 24: 23-28, 2004. (Pubitemid 38082407)
    • (2004) Arteriosclerosis, Thrombosis, and Vascular Biology , vol.24 , Issue.1 , pp. 23-28
    • Cathcart, M.K.1
  • 11
    • 0037032025 scopus 로고    scopus 로고
    • Nitrolinoleate inhibits superoxide generation, degranulation, and integrin expression by human neutrophils: Novel antiinflammatory properties of nitric oxide-derived reactive species in vascular cells
    • DOI 10.1161/01.RES.0000032114.68919.EF
    • Coles B, Bloodsworth A, Clark SR, Lewis MJ, Cross AR, Freeman BA, and O'Donnell VB. Nitrolinoleate inhibits superoxide generation, degranulation, and integrin expression by human neutrophils: novel antiinflammatory properties of nitric oxide-derived reactive species in vascular cells. Circ Res 91: 375-381, 2002. (Pubitemid 35034204)
    • (2002) Circulation Research , vol.91 , Issue.5 , pp. 375-381
    • Coles, B.1    Bloodsworth, A.2    Clark, S.R.3    Lewis, M.J.4    Cross, A.R.5    Freeman, B.A.6    O'Donnell, V.B.7
  • 14
    • 68749091158 scopus 로고    scopus 로고
    • Cul3-mediated Nrf2 ubiquitination antioxidant response element (ARE) activation are dependent on the partial molar volume at position 151 of Keap1
    • Eggler AL, Small E, Hannink M, and Mesecar AD. Cul3-mediated Nrf2 ubiquitination and antioxidant response element (ARE) activation are dependent on the partial molar volume at position 151 of Keap1. Biochem J 422: 171-180, 2009.
    • (2009) Biochem J. , vol.422 , pp. 171-180
    • Eggler, A.L.1    Small, E.2    Hannink, M.3    Mesecar, A.D.4
  • 16
    • 0032757252 scopus 로고    scopus 로고
    • The heme oxygenase pathway its interaction with nitric oxide in the control of cellular homeostasis
    • Foresti R and Motterlini R. The heme oxygenase pathway and its interaction with nitric oxide in the control of cellular homeostasis. Free Radic Res 31: 459-475, 1999.
    • (1999) Free Radic Res , vol.31 , pp. 459-475
    • Foresti, R.1    Motterlini, R.2
  • 17
    • 0028205948 scopus 로고
    • The reaction of low levels of nitrogen dioxide with methyl linoleate in the presence and absence of oxygen
    • Gallon AA and Pryor WA. The reaction of low levels of nitrogen dioxide with methyl linoleate in the presence and absence of oxygen. Lipids 29: 171-176, 1994. (Pubitemid 24085944)
    • (1994) Lipids , vol.29 , Issue.3 , pp. 171-176
    • Gallon, A.A.1    Pryor, W.A.2
  • 20
    • 0029024408 scopus 로고
    • The antioxidant effect of spermine NONOate in human low-density lipoprotein
    • Goss SP, Hogg N, and Kalyanaraman B. The antioxidant effect of spermine NONOate in human low-density lipoprotein. Chem Res Toxicol 8: 800-806, 1995.
    • (1995) Chem Res Toxicol , vol.8 , pp. 800-806
    • Goss, S.P.1    Hogg, N.2    Kalyanaraman, B.3
  • 21
    • 0030845236 scopus 로고    scopus 로고
    • The effect of nitric oxide release rates on the oxidation of human low density lipoprotein
    • DOI 10.1074/jbc.272.34.21647
    • Goss SP, Hogg N, and Kalyanaraman B. The effect of nitric oxide release rates on the oxidation of human low density lipoprotein. J Biol Chem 272: 21647-21653, 1997. (Pubitemid 27374043)
    • (1997) Journal of Biological Chemistry , vol.272 , Issue.34 , pp. 21647-21653
    • Goss, S.P.A.1    Hogg, N.2    Kalyanaraman, B.3
  • 22
    • 84857833776 scopus 로고    scopus 로고
    • Cell signalling by reactive lipid species: New concepts molecular mechanisms
    • Higdon A, Diers AR, Oh JY, Landar A, and Darley-Usmar VM. Cell signalling by reactive lipid species: new concepts and molecular mechanisms. Biochem J 442: 453-464, 2012.
    • (2012) Biochem J. , vol.442 , pp. 453-464
    • Higdon, A.1    Diers, A.R.2    Oh, J.Y.3    Landar, A.4    Darley-Usmar, V.M.5
  • 23
    • 24744453945 scopus 로고    scopus 로고
    • Specific patterns of electrophile adduction trigger Keap1 ubiquitination and Nrf2 activation
    • DOI 10.1074/jbc.M503346200
    • Hong F, Sekhar KR, Freeman ML, and Liebler DC. Specific patterns of electrophile adduction trigger Keap1 ubiquitination and Nrf2 activation. J Biol Chem 280: 31768-31775, 2005. (Pubitemid 41291926)
    • (2005) Journal of Biological Chemistry , vol.280 , Issue.36 , pp. 31768-31775
    • Hong, F.1    Sekhar, K.E.2    Freeman, M.L.3    Liebler, D.C.4
  • 26
    • 0034700236 scopus 로고    scopus 로고
    • Permeation of phospholipid membranes by peroxynitrite
    • Khairutdinov RF, Coddington JW, and Hurst JK. Permeation of phospholipid membranes by peroxynitrite. Biochemistry 39: 14238-14249, 2000.
    • (2000) Biochemistry , vol.39 , pp. 14238-14249
    • Khairutdinov, R.F.1    Coddington, J.W.2    Hurst, J.K.3
  • 28
    • 77950896739 scopus 로고    scopus 로고
    • NADPH oxidases: Functions pathologies in the vasculature
    • Lassegue B and Griendling KK. NADPH oxidases: functions and pathologies in the vasculature. Arterioscler Thromb Vasc Biol 30: 653-661, 2010.
    • (2010) Arterioscler Thromb Vasc Biol , vol.30 , pp. 653-661
    • Lassegue, B.1    Griendling, K.K.2
  • 30
    • 41249083049 scopus 로고    scopus 로고
    • Molecular evolution of Keap1. Two Keap1molecules with distinctive intervening region structures are conserved among fish
    • Li L, KobayashiM, KanekoH,Nakajima-Takagi Y, Nakayama Y, and Yamamoto M. Molecular evolution of Keap1. Two Keap1molecules with distinctive intervening region structures are conserved among fish. J Biol Chem283: 3248-3255, 2008.
    • (2008) J. Biol Chem , vol.283 , pp. 3248-3255
    • Li, L.1    Kobayashim2    Kanekohnakajima-Takagi, Y.3    Nakayama, Y.4    Yamamoto, M.5
  • 32
  • 33
    • 0141794273 scopus 로고    scopus 로고
    • Cholesteryl nitrolinoleate, a nitrated lipid present in human blood plasma and lipoproteins
    • DOI 10.1194/jlr.M200467-JLR200
    • Lima ES, Di Mascio P, and Abdalla DS. Cholesteryl nitrolinoleate, a nitrated lipid present in human blood plasma and lipoproteins. J Lipid Res 44: 1660-1666, 2003. (Pubitemid 37185876)
    • (2003) Journal of Lipid Research , vol.44 , Issue.9 , pp. 1660-1666
    • Lima, E.S.1    Di Mascio, P.2    Abdalla, D.S.P.3
  • 35
    • 84874662091 scopus 로고    scopus 로고
    • Biology of nitrogen oxides in the gastrointestinal tract
    • [Epub ahead of print]; DOI: 10.1136/gutjnl.2011.301649
    • Lundberg JO and Weitzberg E. Biology of nitrogen oxides in the gastrointestinal tract. Gut 2012 [Epub ahead of print]; DOI: 10.1136/gutjnl.2011.301649.
    • (2012) Gut
    • Lundberg, J.O.1    Weitzberg, E.2
  • 36
    • 0034665857 scopus 로고    scopus 로고
    • The productive conformation of arachidonic acid bound to prostaglandin synthase
    • Malkowski MG, Ginell SL, Smith WL, and Garavito RM. The productive conformation of arachidonic acid bound to prostaglandin synthase. Science 289: 1933-1937, 2000.
    • (2000) Science , vol.289 , pp. 1933-1937
    • Malkowski, M.G.1    Ginell, S.L.2    Smith, W.L.3    Garavito, R.M.4
  • 37
    • 0033551847 scopus 로고    scopus 로고
    • Arachidonic acid oxygenation by COX-1 COX-2. Mechanisms of catalysis inhibition
    • Marnett LJ, Rowlinson SW, Goodwin DC, Kalgutkar AS, and Lanzo CA. Arachidonic acid oxygenation by COX-1 and COX-2. Mechanisms of catalysis and inhibition. J Biol Chem 274: 22903-22906, 1999.
    • (1999) J. Biol Chem , vol.274 , pp. 22903-22906
    • Marnett, L.J.1    Rowlinson, S.W.2    Goodwin, D.C.3    Kalgutkar, A.S.4    Lanzo, C.A.5
  • 39
    • 67449149911 scopus 로고    scopus 로고
    • Mitochondrial nitroalkene formation mild uncoupling in ischaemic preconditioning: Implications for cardioprotection
    • Nadtochiy SM, Baker PR, Freeman BA, and Brookes PS. Mitochondrial nitroalkene formation and mild uncoupling in ischaemic preconditioning: implications for cardioprotection. Cardiovasc Res 82: 333-340, 2009.
    • (2009) Cardiovasc Res , vol.82 , pp. 333-340
    • Nadtochiy, S.M.1    Baker, P.R.2    Freeman, B.A.3    Brookes, P.S.4
  • 40
    • 0035910611 scopus 로고    scopus 로고
    • Interactions between nitric oxide and lipid oxidation pathways: Implications for vascular disease
    • O'Donnell VB and Freeman BA. Interactions between nitric oxide and lipid oxidation pathways: implications for vascular disease. Circ Res 88: 12-21, 2001. (Pubitemid 32064077)
    • (2001) Circulation Research , vol.88 , Issue.1 , pp. 12-21
    • O'Donnell, V.B.1    Freeman, B.A.2
  • 43
    • 0032701646 scopus 로고    scopus 로고
    • Myeloperoxidase-generated reactive nitrogen species convert LDL into an atherogenic form in vitro
    • Podrez EA, Schmitt D, Hoff HF, and Hazen SL. Myeloperoxidase-generated reactive nitrogen species convert LDL into an atherogenic form in vitro. J Clin Invest 103: 1547-1560, 1999.
    • (1999) J. Clin Invest , vol.103 , pp. 1547-1560
    • Podrez, E.A.1    Schmitt, D.2    Hoff, H.F.3    Hazen, S.L.4
  • 44
    • 0025874048 scopus 로고
    • Peroxynitrite-induced membrane lipid peroxidation: The cytotoxic potential of superoxide nitric oxide
    • Radi R, Beckman JS, Bush KM, and Freeman BA. Peroxynitrite-induced membrane lipid peroxidation: the cytotoxic potential of superoxide and nitric oxide. Arch Biochem Biophys 288: 481-487, 1991.
    • (1991) Arch Biochem Biophys , vol.288 , pp. 481-487
    • Radi, R.1    Beckman, J.S.2    Bush, K.M.3    Freeman, B.A.4
  • 45
  • 46
    • 0037898985 scopus 로고    scopus 로고
    • Mechanism of free radical oxygenation of polyunsaturated fatty acids by cyclooxygenases
    • Rouzer CA and Marnett LJ. Mechanism of free radical oxygenation of polyunsaturated fatty acids by cyclooxygenases. Chem Rev 103: 2239-2304, 2003.
    • (2003) Chem Rev , vol.103 , pp. 2239-2304
    • Rouzer, C.A.1    Marnett, L.J.2
  • 47
    • 43149088997 scopus 로고    scopus 로고
    • Nitric oxide diffusion across low density lipoprotein inhibition of lipid oxidation-dependent chemiluminescence
    • Rubbo H, Batthyány C, Freeman BA, Radi R, and Denicola A. Nitric oxide diffusion across low density lipoprotein and inhibition of lipid oxidation-dependent chemiluminescence. Nitric Oxide 2: 117, 1998.
    • (1998) Nitric Oxide , vol.2 , pp. 117
    • Rubbo, H.1    Batthyány, C.2    Freeman, B.A.3    Radi, R.4    Denicola, A.5
  • 48
    • 0028793450 scopus 로고
    • Nitric oxide inhibition of lipoxygenasedependent liposome low-density lipoprotein oxidation: Termination of radical chain propagation reactions formation of nitrogen-containing oxidized lipid derivatives
    • Rubbo H, Parthasarathy S, Barnes S, Kirk M, Kalyanaraman B, and Freeman BA. Nitric oxide inhibition of lipoxygenasedependent liposome and low-density lipoprotein oxidation: termination of radical chain propagation reactions and formation of nitrogen-containing oxidized lipid derivatives. Arch Biochem Biophys 324: 15-25, 1995.
    • (1995) Arch Biochem Biophys , vol.324 , pp. 15-25
    • Rubbo, H.1    Parthasarathy, S.2    Barnes, S.3    Kirk, M.4    Kalyanaraman, B.5    Freeman, B.A.6
  • 49
    • 0028151406 scopus 로고
    • Nitric oxide regulation of superoxide peroxynitrite-dependent lipid peroxidation. Formation of novel nitrogen-containing oxidized lipid derivatives
    • Rubbo H, Radi R, Trujillo M, Telleri R, Kalyanaraman B, Barnes S, Kirk M, and Freeman BA. Nitric oxide regulation of superoxide and peroxynitrite- dependent lipid peroxidation. Formation of novel nitrogen-containing oxidized lipid derivatives. J Biol Chem 269: 26066-26075, 1994.
    • (1994) J. Biol Chem , vol.269 , pp. 26066-26075
    • Rubbo, H.1    Radi, R.2    Trujillo, M.3    Telleri, R.4    Kalyanaraman, B.5    Barnes, S.6    Kirk, M.7    Freeman, B.A.8
  • 58
    • 0031587784 scopus 로고    scopus 로고
    • The formation of some antigenic epitopes in oxidized human low-density lipoprotein is inhibited by nitric oxide
    • DOI 10.1006/bbrc.1997.6148
    • Seccia M, Perugini C, and Bellomo G. The formation of some antigenic epitopes in oxidized human low-density lipoprotein is inhibited by nitric oxide. Biochem Biophys Res Commun 232: 613-617, 1997. (Pubitemid 27214044)
    • (1997) Biochemical and Biophysical Research Communications , vol.232 , Issue.3 , pp. 613-617
    • Seccia, M.1    Perugini, C.2    Bellomo, G.3
  • 59
    • 0033791318 scopus 로고    scopus 로고
    • Cyclooxygenases: Structural cellular molecular biology
    • Smith WL, DeWitt DL, and Garavito RM. Cyclooxygenases: structural, cellular, and molecular biology. Annu Rev Biochem 69: 145-182, 2000.
    • (2000) Annu Rev Biochem , vol.69 , pp. 145-182
    • Smith, W.L.1    Dewitt, D.L.2    Garavito, R.M.3
  • 60
    • 0036669774 scopus 로고    scopus 로고
    • The enzymology of prostaglandin endoperoxide H synthases-1-2
    • Smith WL and Song I. The enzymology of prostaglandin endoperoxide H synthases-1 and-2. Prostaglandins Other Lipid Mediat 68-69: 115-128, 2002.
    • (2002) Prostaglandins Other Lipid Mediat , vol.68-69 , pp. 115-128
    • Smith, W.L.1    Song, I.2
  • 61
    • 63849101712 scopus 로고    scopus 로고
    • Nitrooleic acid an endogenous product of nitrative stress activates nociceptive sensory nerves via the direct activation of TRPA1
    • Taylor-Clark TE, Ghatta S, Bettner W, and Undem BJ. Nitrooleic acid, an endogenous product of nitrative stress, activates nociceptive sensory nerves via the direct activation of TRPA1. Mol Pharmacol 75: 820-829, 2009.
    • (2009) Mol Pharmacol , vol.75 , pp. 820-829
    • Taylor-Clark, T.E.1    Ghatta, S.2    Bettner, W.3    Undem, B.J.4
  • 62
    • 0035890228 scopus 로고    scopus 로고
    • Formation of lipid-protein adducts in low-density lipoprotein by fluxes of peroxynitrite and its inhibition by nitric oxide
    • DOI 10.1006/abbi.2001.2583
    • Trostchansky A, Batthyany C, Botti H, Radi R, Denicola A, and Rubbo H. Formation of lipid-protein adducts in lowdensity lipoprotein by fluxes of peroxynitrite and its inhibition by nitric oxide. Arch Biochem Biophys 395: 225-232, 2001. (Pubitemid 33078257)
    • (2001) Archives of Biochemistry and Biophysics , vol.395 , Issue.2 , pp. 225-232
    • Trostchansky, A.1    Batthyany, C.2    Botti, H.3    Radi, R.4    Denicola, A.5    Rubbo, H.6
  • 64
    • 33847649954 scopus 로고    scopus 로고
    • Interactions between nitric oxide and peroxynitrite during prostaglandin endoperoxide H synthase-1 catalysis: A free radical mechanism of inactivation
    • DOI 10.1016/j.freeradbiomed.2007.01.009, PII S0891584907000160
    • Trostchansky A, O'Donnell VB, Goodwin DC, Landino LM, Marnett LJ, Radi R, and Rubbo H. Interactions between nitric oxide and peroxynitrite during prostaglandin endoperoxide H synthase-1 catalysis: a free radical mechanism of inactivation. Free Radic Biol Med 42: 1029-1038, 2007. (Pubitemid 46356900)
    • (2007) Free Radical Biology and Medicine , vol.42 , Issue.7 , pp. 1029-1038
    • Trostchansky, A.1    O'Donnell, V.B.2    Goodwin, D.C.3    Landino, L.M.4    Marnett, L.J.5    Radi, R.6    Rubbo, H.7
  • 66
    • 70349257172 scopus 로고    scopus 로고
    • Nitrofatty acids occur in human plasma in the picomolar range: A targeted nitro-lipidomics G.C.-M.S./M.S study
    • Tsikas D, Zoerner AA, Mitschke A, and Gutzki FM. Nitrofatty acids occur in human plasma in the picomolar range: a targeted nitro-lipidomics GC-MS/MS study. Lipids 44: 855-865, 2009.
    • (2009) Lipids , vol.44 , pp. 855-865
    • Tsikas, D.1    Zoerner, A.A.2    Mitschke, A.3    Gutzki, F.M.4
  • 67
    • 0037207124 scopus 로고    scopus 로고
    • The cyclooxygenase reaction mechanism
    • DOI 10.1021/bi026938h
    • van der Donk WA, Tsai AL, and Kulmacz RJ. The cyclooxygenase reaction mechanism. Biochemistry 41: 15451-15458, 2002. (Pubitemid 36062450)
    • (2002) Biochemistry , vol.41 , Issue.52 , pp. 15451-15458
    • Van Der Donk, W.A.1    Tsai, A.-L.2    Kulmacz, R.J.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.