메뉴 건너뛰기




Volumn 139, Issue 2, 2006, Pages 157-170

Myeloperoxidase-derived 2-chlorohexadecanal forms Schiff bases with primary amines of ethanolamine glycerophospholipids and lysine

Author keywords

Electrospray ionization mass spectrometry; Endothelial cells; Fatty aldehyde; Phosphatidylethanolamine; Plasmenylcholine; Reactive chlorinating species

Indexed keywords

2 CHLOROHEXADECANAL; ALDEHYDE DERIVATIVE; CYANOBOROHYDRIDE SODIUM; HYDROCHLORIC ACID; LYSINE; MYELOPEROXIDASE; ORGANOBORON DERIVATIVE; PHOSPHATIDYLETHANOLAMINE; PHOSPHOLIPASE D; PLASMALOGEN; SCHIFF BASE; UNCLASSIFIED DRUG;

EID: 31844454656     PISSN: 00093084     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chemphyslip.2005.12.003     Document Type: Article
Times cited : (31)

References (39)
  • 1
    • 0035968168 scopus 로고    scopus 로고
    • Reactive chlorinating species produced by myeloperoxidase target the vinyl ether bond of plasmalogens: Identification of 2-chlorohexadecanal
    • C.J. Albert, J.R. Crowley, F.F. Hsu, A.K. Thukkani, and D.A. Ford Reactive chlorinating species produced by myeloperoxidase target the vinyl ether bond of plasmalogens: identification of 2-chlorohexadecanal J. Biol. Chem. 276 2001 23733 23741
    • (2001) J. Biol. Chem. , vol.276 , pp. 23733-23741
    • Albert, C.J.1    Crowley, J.R.2    Hsu, F.F.3    Thukkani, A.K.4    Ford, D.A.5
  • 2
    • 70449246528 scopus 로고
    • Phosphorus assay in column chromatography
    • G.R. Bartlett Phosphorus assay in column chromatography J. Biol. Chem. 234 1959 466 468
    • (1959) J. Biol. Chem. , vol.234 , pp. 466-468
    • Bartlett, G.R.1
  • 4
    • 33845261493 scopus 로고
    • A rapid method of total lipid extraction and purification
    • E.G. Bligh, and W.J. Dyer A rapid method of total lipid extraction and purification Can. J. Biochem. Physiol. 37 1959 911 917
    • (1959) Can. J. Biochem. Physiol. , vol.37 , pp. 911-917
    • Bligh, E.G.1    Dyer, W.J.2
  • 5
    • 0035196175 scopus 로고    scopus 로고
    • Role of 4-hydroxynonenal in modification of cytochrome c oxidase in ischemia/reperfused rat heart
    • J. Chen, G.I. Henderson, and G.L. Freeman Role of 4-hydroxynonenal in modification of cytochrome c oxidase in ischemia/reperfused rat heart J. Mol. Cell. Cardiol. 33 2001 1919 1927
    • (2001) J. Mol. Cell. Cardiol. , vol.33 , pp. 1919-1927
    • Chen, J.1    Henderson, G.I.2    Freeman, G.L.3
  • 6
    • 0028088672 scopus 로고
    • Phospholipid subclass-specific alterations in the kinetics of ion transport across biologic membranes
    • X. Chen, and R.W. Gross Phospholipid subclass-specific alterations in the kinetics of ion transport across biologic membranes Biochemistry 33 1994 13769 13774
    • (1994) Biochemistry , vol.33 , pp. 13769-13774
    • Chen, X.1    Gross, R.W.2
  • 7
    • 0032444930 scopus 로고    scopus 로고
    • Selective hydrolysis of plasmalogens in endothelial cells following thrombin stimulation
    • M.H. Creer, and J. McHowat Selective hydrolysis of plasmalogens in endothelial cells following thrombin stimulation Am. J. Physiol. 275 1998 C1498 C1507
    • (1998) Am. J. Physiol. , vol.275
    • Creer, M.H.1    McHowat, J.2
  • 8
    • 0028292033 scopus 로고
    • Myeloperoxidase, a catalyst for lipoprotein oxidation, is expressed in human atherosclerotic lesions
    • A. Daugherty, J.L. Dunn, D.L. Rateri, and J.W. Heinecke Myeloperoxidase, a catalyst for lipoprotein oxidation, is expressed in human atherosclerotic lesions J. Clin. Invest. 94 1994 437 444
    • (1994) J. Clin. Invest. , vol.94 , pp. 437-444
    • Daugherty, A.1    Dunn, J.L.2    Rateri, D.L.3    Heinecke, J.W.4
  • 9
    • 0032921371 scopus 로고    scopus 로고
    • Formation of 4-hydroxy-2-nonenal-modified proteins in ischemic rat heart
    • P. Eaton, J.M. Li, D.J. Hearse, and M.J. Shattock Formation of 4-hydroxy-2-nonenal-modified proteins in ischemic rat heart Am. J. Physiol. 276 1999 H935 H943
    • (1999) Am. J. Physiol. , vol.276
    • Eaton, P.1    Li, J.M.2    Hearse, D.J.3    Shattock, M.J.4
  • 10
    • 0024672061 scopus 로고
    • Plasmenylethanolamine is the major storage depot for arachidonic acid in rabbit vascular smooth muscle and is rapidly hydrolyzed after angiotensin II stimulation
    • D.A. Ford, and R.W. Gross Plasmenylethanolamine is the major storage depot for arachidonic acid in rabbit vascular smooth muscle and is rapidly hydrolyzed after angiotensin II stimulation Proc. Natl. Acad. Sci. U.S.A. 86 1989 3479 3483
    • (1989) Proc. Natl. Acad. Sci. U.S.A. , vol.86 , pp. 3479-3483
    • Ford, D.A.1    Gross, R.W.2
  • 11
    • 0021336890 scopus 로고
    • High plasmalogen and arachidonic acid content of canine myocardial sarcolemma: A fast atom bombardment mass spectroscopic and gas chromatography-mass spectroscopic characterization
    • R.W. Gross High plasmalogen and arachidonic acid content of canine myocardial sarcolemma: a fast atom bombardment mass spectroscopic and gas chromatography-mass spectroscopic characterization Biochemistry 23 1984 158 165
    • (1984) Biochemistry , vol.23 , pp. 158-165
    • Gross, R.W.1
  • 12
    • 0021910784 scopus 로고
    • Identification of plasmalogen as the major phospholipid constituent of cardiac sarcoplasmic reticulum
    • R.W. Gross Identification of plasmalogen as the major phospholipid constituent of cardiac sarcoplasmic reticulum Biochemistry 24 1985 1662 1668
    • (1985) Biochemistry , vol.24 , pp. 1662-1668
    • Gross, R.W.1
  • 13
    • 0032579194 scopus 로고    scopus 로고
    • The selective activation of the cardiac sarcolemmal sodium-calcium exchanger by plasmalogenic phosphatidic acid produced by phospholipase D
    • C.C. Hale, E.G. Ebeling, F.F. Hsu, and D.A. Ford The selective activation of the cardiac sarcolemmal sodium-calcium exchanger by plasmalogenic phosphatidic acid produced by phospholipase D FEBS Lett. 422 1998 247 251
    • (1998) FEBS Lett. , vol.422 , pp. 247-251
    • Hale, C.C.1    Ebeling, E.G.2    Hsu, F.F.3    Ford, D.A.4
  • 14
    • 0017240322 scopus 로고
    • Studies on the chlorinating activity of myeloperoxidase
    • J.E. Harrison, and J. Schultz Studies on the chlorinating activity of myeloperoxidase J. Biol. Chem. 251 1976 1371 1374
    • (1976) J. Biol. Chem. , vol.251 , pp. 1371-1374
    • Harrison, J.E.1    Schultz, J.2
  • 15
    • 0034672422 scopus 로고    scopus 로고
    • Elevated levels of protein-bound p-hydroxyphenylacetaldehyde, an amino-acid-derived aldehyde generated by myeloperoxidase, are present in human fatty streaks, intermediate lesions and advanced atherosclerotic lesions
    • S.L. Hazen, J.P. Gaut, J.R. Crowley, F.F. Hsu, and J.W. Heinecke Elevated levels of protein-bound p-hydroxyphenylacetaldehyde, an amino-acid-derived aldehyde generated by myeloperoxidase, are present in human fatty streaks, intermediate lesions and advanced atherosclerotic lesions Biochem. J. 352 2000 693 699
    • (2000) Biochem. J. , vol.352 , pp. 693-699
    • Hazen, S.L.1    Gaut, J.P.2    Crowley, J.R.3    Hsu, F.F.4    Heinecke, J.W.5
  • 17
    • 0034615999 scopus 로고    scopus 로고
    • P-hydroxyphenylacetaldehyde, an aldehyde generated by myeloperoxidase, modifies phospholipid amino groups of low-density lipoprotein in human atherosclerotic intima
    • J.I. Heller, J.R. Crowley, S.L. Hazen, D.M. Salvay, P. Wagner, S. Pennathur, and J.W. Heinecke p-hydroxyphenylacetaldehyde, an aldehyde generated by myeloperoxidase, modifies phospholipid amino groups of low-density lipoprotein in human atherosclerotic intima J. Biol. Chem. 275 2000 9957 9962
    • (2000) J. Biol. Chem. , vol.275 , pp. 9957-9962
    • Heller, J.I.1    Crowley, J.R.2    Hazen, S.L.3    Salvay, D.M.4    Wagner, P.5    Pennathur, S.6    Heinecke, J.W.7
  • 18
    • 0030810619 scopus 로고    scopus 로고
    • Isolation of animal cell mutants defective in long-chain fatty aldehyde dehydrogenase sensitivity to fatty aldehydes and Schiff's base modification of phospholipids: Implications for Sjogren-Larsson syndrome
    • P.F. James, and R.A. Zoeller Isolation of animal cell mutants defective in long-chain fatty aldehyde dehydrogenase sensitivity to fatty aldehydes and Schiff's base modification of phospholipids: implications for Sjogren-Larsson syndrome J. Biol. Chem. 272 1997 23532 23539
    • (1997) J. Biol. Chem. , vol.272 , pp. 23532-23539
    • James, P.F.1    Zoeller, R.A.2
  • 19
    • 0031042499 scopus 로고    scopus 로고
    • Plasmalogens and oxidative stress: Evidence against a major role of plasmalogens in protection against the superoxide anion radical
    • G.A. Jansen, and R.J. Wanders Plasmalogens and oxidative stress: evidence against a major role of plasmalogens in protection against the superoxide anion radical J. Inhib. Met. Dis. 20 1997 85 94
    • (1997) J. Inhib. Met. Dis. , vol.20 , pp. 85-94
    • Jansen, G.A.1    Wanders, R.J.2
  • 21
    • 10644253777 scopus 로고    scopus 로고
    • 2-Chlorohexadecanal derived from hypochlorite-modified high-density lipoprotein-associated plasmalogen is a natural inhibitor of endothelial nitric oxide biosynthesis
    • G. Marsche, R. Heller, G. Fauler, A. Kovacevic, A. Nuszkowski, W. Graier, W. Sattler, and E. Malle 2-Chlorohexadecanal derived from hypochlorite-modified high-density lipoprotein-associated plasmalogen is a natural inhibitor of endothelial nitric oxide biosynthesis Arterio. Thromb. Vasc. Biol. 24 2004 2302 2306
    • (2004) Arterio. Thromb. Vasc. Biol. , vol.24 , pp. 2302-2306
    • Marsche, G.1    Heller, R.2    Fauler, G.3    Kovacevic, A.4    Nuszkowski, A.5    Graier, W.6    Sattler, W.7    Malle, E.8
  • 22
    • 0023711006 scopus 로고
    • Disappearance of plasmalogens from membranes of animal cells subjected to photosensitized oxidation
    • O.H. Morand, R.A. Zoeller, and C.R. Raetz Disappearance of plasmalogens from membranes of animal cells subjected to photosensitized oxidation J. Biol. Chem. 263 1988 11597 11606
    • (1988) J. Biol. Chem. , vol.263 , pp. 11597-11606
    • Morand, O.H.1    Zoeller, R.A.2    Raetz, C.R.3
  • 23
    • 8544251150 scopus 로고
    • The acid ionization constant of HOCl from 5 to 35
    • J.C. Morris The acid ionization constant of HOCl from 5 to 35 J. Phys. Chem. 70 1966 3798 3805
    • (1966) J. Phys. Chem. , vol.70 , pp. 3798-3805
    • Morris, J.C.1
  • 24
    • 0034659164 scopus 로고    scopus 로고
    • Myeloperoxidase-generated oxidants and atherosclerosis
    • E.A. Podrez, H.M. Abu-Soud, and S.L. Hazen Myeloperoxidase-generated oxidants and atherosclerosis Free Radic. Biol. Med. 28 2000 1717 1725
    • (2000) Free Radic. Biol. Med. , vol.28 , pp. 1717-1725
    • Podrez, E.A.1    Abu-Soud, H.M.2    Hazen, S.L.3
  • 25
    • 0023622336 scopus 로고
    • Fatty alcohol metabolism in cultured human fibroblasts. Evidence for a fatty alcohol cycle
    • W.B. Rizzo, D.A. Craft, A.L. Dammann, and M.W. Phillips Fatty alcohol metabolism in cultured human fibroblasts. Evidence for a fatty alcohol cycle J. Biol. Chem. 262 1987 17412 17419
    • (1987) J. Biol. Chem. , vol.262 , pp. 17412-17419
    • Rizzo, W.B.1    Craft, D.A.2    Dammann, A.L.3    Phillips, M.W.4
  • 26
    • 0033661740 scopus 로고    scopus 로고
    • Pathways and mechanisms of N-acylethanolamine biosynthesis: Can anandamide be generated selectively?
    • H.H.O. Schmid Pathways and mechanisms of N-acylethanolamine biosynthesis: can anandamide be generated selectively? Chem. Phys. Lipids 108 2000 71 87
    • (2000) Chem. Phys. Lipids , vol.108 , pp. 71-87
    • Schmid, H.H.O.1
  • 27
  • 28
    • 0021910761 scopus 로고
    • Oxidant membrane injury by the neutrophil myeloperoxidase system II. Injury by stimulated neutrophils and protection by lipid-soluble antioxidants
    • S.M. Sepe, and R.A. Clark Oxidant membrane injury by the neutrophil myeloperoxidase system II. Injury by stimulated neutrophils and protection by lipid-soluble antioxidants J. Immunol. 134 1985 1896 1901
    • (1985) J. Immunol. , vol.134 , pp. 1896-1901
    • Sepe, S.M.1    Clark, R.A.2
  • 29
    • 0035890031 scopus 로고    scopus 로고
    • Plasmalogen degradation by oxidative stress: Production and disappearance of specific fatty aldehydes and fatty alpha-hydroxyaldehydes
    • S. Stadelmann-Ingrand, S. Favreliere, B. Fauconneau, G. Mauco, and C. Tallineau Plasmalogen degradation by oxidative stress: production and disappearance of specific fatty aldehydes and fatty alpha-hydroxyaldehydes Free Radic. Biol. Med. 31 2001 1263 1271
    • (2001) Free Radic. Biol. Med. , vol.31 , pp. 1263-1271
    • Stadelmann-Ingrand, S.1    Favreliere, S.2    Fauconneau, B.3    Mauco, G.4    Tallineau, C.5
  • 30
    • 3042545925 scopus 로고    scopus 로고
    • Evidence for the reactivity of fatty aldehydes released from oxidized plasmalogens with phosphatidylethanolamine to form Schiff base adducts in rat brain homogenates
    • S. Stadelmann-Ingrand, R. Pontcharraud, and B. Fauconneau Evidence for the reactivity of fatty aldehydes released from oxidized plasmalogens with phosphatidylethanolamine to form Schiff base adducts in rat brain homogenates Chem. Phys. Lipids 131 2004 93 105
    • (2004) Chem. Phys. Lipids , vol.131 , pp. 93-105
    • Stadelmann-Ingrand, S.1    Pontcharraud, R.2    Fauconneau, B.3
  • 31
    • 0025690273 scopus 로고
    • Selective deacylation of arachidonate-containing ethanolamine-linked phosphoglycerides in stimulated human neutrophils
    • T.G. Tessner, D.G. Greene, and R.L. Wykle Selective deacylation of arachidonate-containing ethanolamine-linked phosphoglycerides in stimulated human neutrophils J. Biol. Chem. 265 1990 21032 21038
    • (1990) J. Biol. Chem. , vol.265 , pp. 21032-21038
    • Tessner, T.G.1    Greene, D.G.2    Wykle, R.L.3
  • 32
    • 0141592466 scopus 로고    scopus 로고
    • Myeloperoxidase-derived reactive chlorinating species from human monocytes target plasmalogens in low density lipoprotein
    • A.K. Thukkani, C.J. Albert, K.R. Wildsmith, M.C. Messner, B.D. Martinson, F.F. Hsu, and D.A. Ford Myeloperoxidase-derived reactive chlorinating species from human monocytes target plasmalogens in low density lipoprotein J. Biol. Chem. 278 2003 36365 36372
    • (2003) J. Biol. Chem. , vol.278 , pp. 36365-36372
    • Thukkani, A.K.1    Albert, C.J.2    Wildsmith, K.R.3    Messner, M.C.4    Martinson, B.D.5    Hsu, F.F.6    Ford, D.A.7
  • 33
    • 0037040239 scopus 로고    scopus 로고
    • Reactive chlorinating species produced during neutrophil activation target tissue plasmalogens: Production of the chemoattractant 2-chlorohexadecanal
    • A.K. Thukkani, F.F. Hsu, J.R. Crowley, R.B. Wysolmerski, C.J. Albert, and D.A. Ford Reactive chlorinating species produced during neutrophil activation target tissue plasmalogens: production of the chemoattractant 2-chlorohexadecanal J. Biol. Chem. 277 2002 3842 3849
    • (2002) J. Biol. Chem. , vol.277 , pp. 3842-3849
    • Thukkani, A.K.1    Hsu, F.F.2    Crowley, J.R.3    Wysolmerski, R.B.4    Albert, C.J.5    Ford, D.A.6
  • 34
    • 19344371455 scopus 로고    scopus 로고
    • Neutrophil-mediated accumulation of 2-ClHDA during myocardial infarction: 2-ClHDA-mediated myocardial injury
    • A.K. Thukkani, B.D. Martinson, C.J. Albert, G.A. Vogler, and D.A. Ford Neutrophil-mediated accumulation of 2-ClHDA during myocardial infarction: 2-ClHDA-mediated myocardial injury Am. J. Physiol. 288 2005 H2955 H2964
    • (2005) Am. J. Physiol. , vol.288
    • Thukkani, A.K.1    Martinson, B.D.2    Albert, C.J.3    Vogler, G.A.4    Ford, D.A.5
  • 35
    • 0348049466 scopus 로고    scopus 로고
    • Identification of alpha-chloro fatty aldehydes and unsaturated lysophosphatidylcholine molecular species in human atherosclerotic lesions
    • A.K. Thukkani, J. McHowat, F.F. Hsu, M.L. Brennan, S.L. Hazen, and D.A. Ford Identification of alpha-chloro fatty aldehydes and unsaturated lysophosphatidylcholine molecular species in human atherosclerotic lesions Circulation 108 2003 3128 3133
    • (2003) Circulation , vol.108 , pp. 3128-3133
    • Thukkani, A.K.1    McHowat, J.2    Hsu, F.F.3    Brennan, M.L.4    Hazen, S.L.5    Ford, D.A.6
  • 36
    • 0034659147 scopus 로고    scopus 로고
    • Role of reactive aldehyde in cardiovascular diseases
    • K. Uchida Role of reactive aldehyde in cardiovascular diseases Free Radic. Biol. Med. 28 2000 1685 1696
    • (2000) Free Radic. Biol. Med. , vol.28 , pp. 1685-1696
    • Uchida, K.1
  • 37
    • 0027946778 scopus 로고
    • Michael addition-type 4-hydroxy-2-nonenal adducts in modified low-density lipoproteins: Markers for atherosclerosis
    • K. Uchida, S. Toyokuni, K. Nishikawa, S. Kawakishi, H. Oda, H. Hiai, and E.R. Stadtman Michael addition-type 4-hydroxy-2-nonenal adducts in modified low-density lipoproteins: markers for atherosclerosis Biochemistry 33 1994 12487 12494
    • (1994) Biochemistry , vol.33 , pp. 12487-12494
    • Uchida, K.1    Toyokuni, S.2    Nishikawa, K.3    Kawakishi, S.4    Oda, H.5    Hiai, H.6    Stadtman, E.R.7
  • 39
    • 0023782245 scopus 로고
    • A possible role for plasmalogens in protecting animal cells against photosensitized killing
    • R.A. Zoeller, O.H. Morand, and C.R. Raetz A possible role for plasmalogens in protecting animal cells against photosensitized killing J. Biol. Chem. 263 1988 11590 11596
    • (1988) J. Biol. Chem. , vol.263 , pp. 11590-11596
    • Zoeller, R.A.1    Morand, O.H.2    Raetz, C.R.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.