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Volumn 144, Issue 1, 1999, Pages 79-90

Novel reversible, irreversible and fluorescent inhibitors of platelet- activating factor acetylhydrolase as mechanistic probes

Author keywords

Fluorescence; Inhibitors; Macrophages; Platelet activating factor acetylhydrolase

Indexed keywords

1 ALKYL 2 ACETYLGLYCEROPHOSPHOCHOLINE ESTERASE; 1 O DECYLOXY [10 (4 PYRENIL)BUTOXY] 2 DESOXY 2 AMINO CARBAMOYLMETHYL GLYCERO 3 PHOSPHOCHOLINE; 1 O HEXADECYL 2 DESOXY 2 AMINOMETHYLCARBAMOYL 2 METHYL GLYCERO 3 PHOSPHOCHOLINE; ETHER PHOSPHOLIPID; GLYCEROL; PHOSPHATIDYLCHOLINE; UNCLASSIFIED DRUG;

EID: 0032974586     PISSN: 00219150     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0021-9150(99)00034-9     Document Type: Article
Times cited : (6)

References (48)
  • 1
    • 0019789918 scopus 로고
    • A specific acetylhydrolase for 1-alkyl-2-acetyl-sn-glycero-3-phosphocholine (a hypotensive and platelet-activating lipid)
    • Blank M.C., Lee T.C., Fitzgerald V., Snyder F. A specific acetylhydrolase for 1-alkyl-2-acetyl-sn-glycero-3-phosphocholine (a hypotensive and platelet-activating lipid). J Biol Chem. 256:1981;175-178.
    • (1981) J Biol Chem , vol.256 , pp. 175-178
    • Blank, M.C.1    Lee, T.C.2    Fitzgerald, V.3    Snyder, F.4
  • 2
    • 0021075355 scopus 로고
    • Human serum acid-labile factor is an acylhydrolase that inactivates platelet-activating factor
    • Farr R.S., Wardlow M.L., Cox C.P., Meng K.E., Greene D.E. Human serum acid-labile factor is an acylhydrolase that inactivates platelet-activating factor. Fed Proc Fed Am Soc Exp Biol. 42:1983;3120-3122.
    • (1983) Fed Proc Fed Am Soc Exp Biol , vol.42 , pp. 3120-3122
    • Farr, R.S.1    Wardlow, M.L.2    Cox, C.P.3    Meng, K.E.4    Greene, D.E.5
  • 3
    • 0023180687 scopus 로고
    • Human plasma platelet-activating factor acetylhydrolase: Purification and properties
    • Stafforini D.M., McIntyre T.M., Prescott S.M. Human plasma platelet-activating factor acetylhydrolase: purification and properties. J Biol Chem. 262:1987;4223-4230.
    • (1987) J Biol Chem , vol.262 , pp. 4223-4230
    • Stafforini, D.M.1    McIntyre, T.M.2    Prescott, S.M.3
  • 6
    • 0023278621 scopus 로고
    • Human plasma platelet-activating factor acetylhydrolase: Association with lipoprotein particles and role in the degradation of platelet-activating factor
    • Stafforini D.M., McIntyre T.M., Carter M.E., Prescott S.M. Human plasma platelet-activating factor acetylhydrolase: association with lipoprotein particles and role in the degradation of platelet-activating factor. J Biol Chem. 262:1987;4215-4222.
    • (1987) J Biol Chem , vol.262 , pp. 4215-4222
    • Stafforini, D.M.1    McIntyre, T.M.2    Carter, M.E.3    Prescott, S.M.4
  • 7
    • 0029620828 scopus 로고
    • Enhanced association of platelet activating factor acetylhydrolase with Lipoprotein(a) in comparison to low density lipoprotein
    • Blencowe C., Hermetter A., Kostner G.M., Deigner H.P. Enhanced association of platelet activating factor acetylhydrolase with Lipoprotein(a) in comparison to low density lipoprotein. J Biol Chem. 270:1995;31151-31157.
    • (1995) J Biol Chem , vol.270 , pp. 31151-31157
    • Blencowe, C.1    Hermetter, A.2    Kostner, G.M.3    Deigner, H.P.4
  • 8
    • 0029986601 scopus 로고    scopus 로고
    • Purification, properties, sequencing, and cloning of a lipoprotein-associated, serine-dependent phospholipase involved in the oxidative modification of low-density lipoproteins
    • Tew D.G., Southan C., Rice S.Q., Lawrence G.M., Li H., Boyd H.F., Moores K., Gloger I.S., Macphee C.H. Purification, properties, sequencing, and cloning of a lipoprotein-associated, serine-dependent phospholipase involved in the oxidative modification of low-density lipoproteins. Arterioscler Thromb Vasc Biol. 16:1996;591-599.
    • (1996) Arterioscler Thromb Vasc Biol , vol.16 , pp. 591-599
    • Tew, D.G.1    Southan, C.2    Rice, S.Q.3    Lawrence, G.M.4    Li, H.5    Boyd, H.F.6    Moores, K.7    Gloger, I.S.8    MacPhee, C.H.9
  • 9
    • 0024536159 scopus 로고
    • An oxidized derivative of phosphatidylcholine is a substrate for the platelet-activating factor acetylhydrolase from human plasma
    • Stremler K.E., Stafforini D.M., Prescott S.M., Zimmerman G.A., McIntyre T.M. An oxidized derivative of phosphatidylcholine is a substrate for the platelet-activating factor acetylhydrolase from human plasma. J Biol Chem. 264:1989;5331-5334.
    • (1989) J Biol Chem , vol.264 , pp. 5331-5334
    • Stremler, K.E.1    Stafforini, D.M.2    Prescott, S.M.3    Zimmerman, G.A.4    McIntyre, T.M.5
  • 10
    • 0025908558 scopus 로고
    • Human plasma PAF acetylhydrolase: Oxidatively fragmented phospholipids as substrates
    • Stremler K.E., Stafforini D.M., Prescott S.M., McIntyre T.M. Human plasma PAF acetylhydrolase: oxidatively fragmented phospholipids as substrates. J Biol Chem. 266:1991;11095-11103.
    • (1991) J Biol Chem , vol.266 , pp. 11095-11103
    • Stremler, K.E.1    Stafforini, D.M.2    Prescott, S.M.3    McIntyre, T.M.4
  • 11
    • 0025783171 scopus 로고
    • Oxidatively fragmented phosphatidylcholines activate human neutrophils through the receptor for platelet-activating factor
    • Smiley P.L., Stremler K.E., Prescott S.M., Zimmerman G.A., McIntyre T.M. Oxidatively fragmented phosphatidylcholines activate human neutrophils through the receptor for platelet-activating factor. J Biol Chem. 266:1991;11104-11110.
    • (1991) J Biol Chem , vol.266 , pp. 11104-11110
    • Smiley, P.L.1    Stremler, K.E.2    Prescott, S.M.3    Zimmerman, G.A.4    McIntyre, T.M.5
  • 13
    • 0027027667 scopus 로고
    • The platelet-activating factor acetylhydrolase from human plasma prevents oxidative modifications of low-density lipoprotein
    • Stafforini D.M., Zimmerman G.A., McIntyre T.M., Prescott S.M. The platelet-activating factor acetylhydrolase from human plasma prevents oxidative modifications of low-density lipoprotein. Trans Assoc Am Physicians. 105:1992;44-63.
    • (1992) Trans Assoc Am Physicians , vol.105 , pp. 44-63
    • Stafforini, D.M.1    Zimmerman, G.A.2    McIntyre, T.M.3    Prescott, S.M.4
  • 17
    • 0030614354 scopus 로고    scopus 로고
    • 2 superfamily of a signal transduction enzymes
    • 2 superfamily of a signal transduction enzymes. TIBS. 22:1997;1-2.
    • (1997) TIBS , vol.22 , pp. 1-2
    • Dennis, E.A.1
  • 19
    • 0020523662 scopus 로고
    • Inactivation of 1-alkyl-2-acetyl-sn-glycero-3-phosphocholine by a plasma acetylhydrolase: Higher activities in hypertensive rats
    • Blank M.L., Hall M. N., Cress E.A., Snyder F. Inactivation of 1-alkyl-2-acetyl-sn-glycero-3-phosphocholine by a plasma acetylhydrolase: higher activities in hypertensive rats. Biochem Biophys Res Commun. 113:1983;666-671.
    • (1983) Biochem Biophys Res Commun , vol.113 , pp. 666-671
    • Blank, M.L.1    Hall, M.N.2    Cress, E.A.3    Snyder, F.4
  • 20
    • 0024521694 scopus 로고
    • Hydrolysis of phosphatidylcholine during LDL oxidation is mediated by platelet-activating factor acetylhydrolase
    • Steinbrecher U.P., Pritchard P.H. Hydrolysis of phosphatidylcholine during LDL oxidation is mediated by platelet-activating factor acetylhydrolase. J Lipid Res. 30:1989;305-315.
    • (1989) J Lipid Res , vol.30 , pp. 305-315
    • Steinbrecher, U.P.1    Pritchard, P.H.2
  • 21
    • 0030041824 scopus 로고    scopus 로고
    • Pefabloc, 4-[2-aminoethyl]benzenesulfonyl fluoride, is a new, potent nontoxic and irreversible inhibitor of PAF-degrading acetylhydrolase
    • Dentan C., Tselepis A.D., Chapman M.J., Ninio E. Pefabloc, 4-[2-aminoethyl]benzenesulfonyl fluoride, is a new, potent nontoxic and irreversible inhibitor of PAF-degrading acetylhydrolase. Biochem Biophys Acta. 1299:1996;353-357.
    • (1996) Biochem Biophys Acta , vol.1299 , pp. 353-357
    • Dentan, C.1    Tselepis, A.D.2    Chapman, M.J.3    Ninio, E.4
  • 22
    • 73649151319 scopus 로고
    • Esters of methanesulfonic acid as irreversible inhibitors of acetylcholinesterase
    • Kitz R., Wilson I.B. Esters of methanesulfonic acid as irreversible inhibitors of acetylcholinesterase. J Biol Chem. 237:1962;3245-3249.
    • (1962) J Biol Chem , vol.237 , pp. 3245-3249
    • Kitz, R.1    Wilson, I.B.2
  • 23
    • 33845261493 scopus 로고
    • A rapid method of total lipid extraction and purification
    • Bligh E.G., Dyer W.J. 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
  • 24
    • 0017155490 scopus 로고
    • Establishment and characterization of a hystolytic lymphoma cell-line (U937)
    • Sundström C., Nilson K. Establishment and characterization of a hystolytic lymphoma cell-line (U937). Int J Cancer. 17:1976;565-577.
    • (1976) Int J Cancer , vol.17 , pp. 565-577
    • Sundström, C.1    Nilson, K.2
  • 25
    • 0029992293 scopus 로고    scopus 로고
    • Stimulation of mitogen activated protein kinase by LDL and oxLDL in human U-937 macrophage-like cell
    • Deigner H.P., Claus R. Stimulation of mitogen activated protein kinase by LDL and oxLDL in human U-937 macrophage-like cell. FEBS Lett. 385:1996;149-153.
    • (1996) FEBS Lett , vol.385 , pp. 149-153
    • Deigner, H.P.1    Claus, R.2
  • 26
    • 0028986701 scopus 로고
    • Metabolism and distribution of intramolecular excimer-forming dipyrenebutanoyl glycerophospholipids in human fibroblasts. Marked resistance to metabolic degradation
    • Kasurinen J., Somerharju P. Metabolism and distribution of intramolecular excimer-forming dipyrenebutanoyl glycerophospholipids in human fibroblasts. Marked resistance to metabolic degradation. Biochemistry. 34:1995;2049-2057.
    • (1995) Biochemistry , vol.34 , pp. 2049-2057
    • Kasurinen, J.1    Somerharju, P.2
  • 27
    • 0030939509 scopus 로고    scopus 로고
    • Modified low density lipoprotein delivers substrate for ceramide formation and stimulates the sphingomyelin-ceramide pathway in human macrophages
    • Kinscherf R., Claus R., Deigner H.P., Nauen O., Gehrke C., Hermetter A., Rußwurm S., Daniel V., Hack V., Metz J. Modified low density lipoprotein delivers substrate for ceramide formation and stimulates the sphingomyelin-ceramide pathway in human macrophages. FEBS Lett. 405:1997;55-59.
    • (1997) FEBS Lett , vol.405 , pp. 55-59
    • Kinscherf, R.1    Claus, R.2    Deigner, H.P.3    Nauen, O.4    Gehrke, C.5    Hermetter, A.6    Rußwurm, S.7    Daniel, V.8    Hack, V.9    Metz, J.10
  • 28
    • 0020067240 scopus 로고
    • A new method for the stereospecific synthesis of ether phospholipids. Preparation of the amide analog of platelet-activating factor and related derivatives
    • Chandrakumar N.S., Hajdu J. A new method for the stereospecific synthesis of ether phospholipids. Preparation of the amide analog of platelet-activating factor and related derivatives. Tetrahedron Lett. 23:1982;1043-1046.
    • (1982) Tetrahedron Lett , vol.23 , pp. 1043-1046
    • Chandrakumar, N.S.1    Hajdu, J.2
  • 29
    • 0001076388 scopus 로고
    • Stereospecific synthesis of ether phospholipids. Preparation of 1-alkyl-2-(acylamino)-2-desoxyglycero-phosphocholines
    • Chandrakumar N.S., Hajdu J. Stereospecific synthesis of ether phospholipids. Preparation of 1-alkyl-2-(acylamino)-2-desoxyglycero-phosphocholines. J Org Chem. 59:1983;1197-1202.
    • (1983) J Org Chem , vol.59 , pp. 1197-1202
    • Chandrakumar, N.S.1    Hajdu, J.2
  • 30
    • 0026609357 scopus 로고
    • Rapid synthesis of 2-desoxy-2-amino-3-phosphocholine-glycerinic-acid-alkylester, 1-alkyl-1-desoxy- And 1-O-alkyl-2-desoxy-2-amino-sn-glycero-3-phosphocholines, -3-phospho-N,N′-dimethyletha-nolamine and -3-phospho-Fmoc-serine-methylester
    • Deigner H.P., Fyrnys B. Rapid synthesis of 2-desoxy-2-amino-3-phosphocholine-glycerinic-acid-alkylester, 1-alkyl-1-desoxy- and 1-O-alkyl-2-desoxy-2-amino-sn-glycero-3-phosphocholines, -3-phospho-N,N′-dimethyletha-nolamine and -3-phospho-Fmoc-serine-methylester. Chem Phys Lipids. 61:1992;199-208.
    • (1992) Chem Phys Lipids , vol.61 , pp. 199-208
    • Deigner, H.P.1    Fyrnys, B.2
  • 31
    • 0027954245 scopus 로고
    • 32P] labelled 1-O-alkyl-2-desoxy-2-amino-sn-glycero-3-phosphocholines
    • 32P] labelled 1-O-alkyl-2-desoxy-2-amino-sn-glycero-3-phosphocholines. J Labelled Compd Rad. 34:1993;185-189.
    • (1993) J Labelled Compd Rad , vol.34 , pp. 185-189
    • Deigner, H.P.1    Fyrnys, B.2
  • 32
    • 33845376479 scopus 로고
    • Evidence for hemiketals as intermediates in the inactivation of serine proteinases with halomethyl ketones
    • McMurray J.S., Dyckes D.F. Evidence for hemiketals as intermediates in the inactivation of serine proteinases with halomethyl ketones. Biochemistry. 25:1986;2298-2301.
    • (1986) Biochemistry , vol.25 , pp. 2298-2301
    • McMurray, J.S.1    Dyckes, D.F.2
  • 34
    • 0000682257 scopus 로고
    • The mechanism of the alkaline hydrolysis of p-nitrophenyl N-methylcarbamate
    • Bender M.L., Homer R.B. The mechanism of the alkaline hydrolysis of p-nitrophenyl N-methylcarbamate. J Org Chem. 30:1965;3975-3978.
    • (1965) J Org Chem , vol.30 , pp. 3975-3978
    • Bender, M.L.1    Homer, R.B.2
  • 35
    • 84943887467 scopus 로고
    • The establishment of a carbanion mechanism for ester hydrolysis and the unimportance of electrostatic effects of (substituents on the rates of hydroxide ion attack at the ester carbonyl group
    • Bruice T.C., Holmquist B. The establishment of a carbanion mechanism for ester hydrolysis and the unimportance of electrostatic effects of (substituents on the rates of hydroxide ion attack at the ester carbonyl group. J Am Chem Soc. 90:1986;7136-7138.
    • (1986) J Am Chem Soc , vol.90 , pp. 7136-7138
    • Bruice, T.C.1    Holmquist, B.2
  • 40
    • 0019882446 scopus 로고
    • Potent platelet stimulating activity of enantiomers of acetyl glyceryl ether phosphorylcholine and its methoxy analogues
    • Hanahan D.J., Munder P.G., Satouchi K., McManus L.M., Pinckard R.N. Potent platelet stimulating activity of enantiomers of acetyl glyceryl ether phosphorylcholine and its methoxy analogues. Biochem Biophys Res Comm. 99:1981;183-188.
    • (1981) Biochem Biophys Res Comm , vol.99 , pp. 183-188
    • Hanahan, D.J.1    Munder, P.G.2    Satouchi, K.3    McManus, L.M.4    Pinckard, R.N.5
  • 42
    • 0000410557 scopus 로고
    • Defining the dimensions of the catalytic site of phospholipase A2 using amide substrate analogues
    • Yu L., Dennis E.A. Defining the dimensions of the catalytic site of phospholipase A2 using amide substrate analogues. J Am Chem Soc. 114:1992;8757-8763.
    • (1992) J Am Chem Soc , vol.114 , pp. 8757-8763
    • Yu, L.1    Dennis, E.A.2
  • 43
    • 0029963898 scopus 로고    scopus 로고
    • Degradation of pyrene-labelled phospholipids by lysosomal phospholipases in vitro
    • Lusa S., Myllärniemi M., Volomen K., Vauhkonen M., Somerharju P. Degradation of pyrene-labelled phospholipids by lysosomal phospholipases in vitro. Biochem J. 315:1996;947-952.
    • (1996) Biochem J , vol.315 , pp. 947-952
    • Lusa, S.1    Myllärniemi, M.2    Volomen, K.3    Vauhkonen, M.4    Somerharju, P.5
  • 45
    • 0027401890 scopus 로고
    • The platelet-activating factor acetylhydrolase from human erythrocytes. Purification and properties
    • Stafforini D.M., Rollins E.N., Prescott S.M., McIntyre T.M. The platelet-activating factor acetylhydrolase from human erythrocytes. Purification and properties. J Biol Chem. 268:1993;3857-3865.
    • (1993) J Biol Chem , vol.268 , pp. 3857-3865
    • Stafforini, D.M.1    Rollins, E.N.2    Prescott, S.M.3    McIntyre, T.M.4
  • 46
    • 0025908898 scopus 로고
    • Peptidyl (acyloxy)methyl ketones and the quiescent affinity label concept: The departing group as a variable structural element in the design of inactivators of cysteine proteinases
    • Krantz A.L., Copp L., Coles P.J., Smith R.A., Heard S.B. Peptidyl (acyloxy)methyl ketones and the quiescent affinity label concept: The departing group as a variable structural element in the design of inactivators of cysteine proteinases. Biochemistry. 30:1991;4678-4687.
    • (1991) Biochemistry , vol.30 , pp. 4678-4687
    • Krantz, A.L.1    Copp, L.2    Coles, P.J.3    Smith, R.A.4    Heard, S.B.5
  • 48
    • 0029926948 scopus 로고    scopus 로고
    • The energetics of hydrogen bonds in model systems: Implications for enzymatic catalysis
    • Shan S.O., Loh S., Herschlag D. The energetics of hydrogen bonds in model systems: implications for enzymatic catalysis. Science. 272:1996;97-101.
    • (1996) Science , vol.272 , pp. 97-101
    • Shan, S.O.1    Loh, S.2    Herschlag, D.3


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