메뉴 건너뛰기




Volumn 67, Issue 3, 2005, Pages 640-647

Structural determinants of arylacetic acid nonsteroidal anti-inflammatory drugs necessary for binding and activation of the prostaglandin D2 receptor CRTH2

Author keywords

[No Author keywords available]

Indexed keywords

2 DESMETHYLINDOMETHACIN; 4 BROMO BENZYL INDOMETHACIN; 5 HYDROXYINDOLEACETIC ACID; 5 HYDROXYTRYPTOPHAN; 5' O DESMETHYL INDOMETHACIN; ARYLACETIC ACID DERIVATIVE; CHEMOATTRACTANT; CYCLIC AMP; DICLOFENAC; G PROTEIN COUPLED RECEPTOR; INDOLE DERIVATIVE; INDOLEACETIC ACID; INDOMETACIN; INDOMETHACIN AMIDE; INDOMETHACIN METHYL ESTER; NONSTEROID ANTIINFLAMMATORY AGENT; PROSTAGLANDIN D2; PROSTAGLANDIN RECEPTOR; PROSTAGLANDIN SYNTHASE INHIBITOR; RAMATROBAN; SEROTONIN; SULINDAC SULFIDE; TRYPTOPHAN; UNCLASSIFIED DRUG; ZOMEPIRAC;

EID: 14944363741     PISSN: 0026895X     EISSN: None     Source Type: Journal    
DOI: 10.1124/mol.104.007971     Document Type: Article
Times cited : (28)

References (40)
  • 1
    • 0031026413 scopus 로고    scopus 로고
    • Substitution of charged amino acid residues in transmembrane regions 6 and 7 affect ligand binding and signal transduction of the prostaglandin EP3 receptor
    • Audoly L and Breyer RM (1997) Substitution of charged amino acid residues in transmembrane regions 6 and 7 affect ligand binding and signal transduction of the prostaglandin EP3 receptor. Mol Pharmacol 51:61-68.
    • (1997) Mol Pharmacol , vol.51 , pp. 61-68
    • Audoly, L.1    Breyer, R.M.2
  • 2
    • 0023821185 scopus 로고
    • The release of prostaglandin D2 from human skin in vivo and in vitro during immediate allergic reactions
    • Barr RM, Koro O, Francis DM, Black AK, Numata T, and Greaves MW (1988) The release of prostaglandin D2 from human skin in vivo and in vitro during immediate allergic reactions. Br J Pharmacol 94:773-780.
    • (1988) Br J Pharmacol , vol.94 , pp. 773-780
    • Barr, R.M.1    Koro, O.2    Francis, D.M.3    Black, A.K.4    Numata, T.5    Greaves, M.W.6
  • 3
    • 0015861774 scopus 로고
    • Relationship between the inhibition constant (K1) and the concentration of inhibitor which causes 50 per cent inhibition (I50) of an enzymatic reaction
    • Cheng Y and Prusoff WH (1973) Relationship between the inhibition constant (K1) and the concentration of inhibitor which causes 50 per cent inhibition (I50) of an enzymatic reaction. Biochem Pharmacol 22:3099-3108.
    • (1973) Biochem Pharmacol , vol.22 , pp. 3099-3108
    • Cheng, Y.1    Prusoff, W.H.2
  • 4
    • 0019856442 scopus 로고
    • Effect of indomethacin on the binding of the chemotactic peptide formyl-Met-Leu-Phe on human polymorphonuclear leukocytes
    • Cost H, Gespach C, and Abita JP (1981) Effect of indomethacin on the binding of the chemotactic peptide formyl-Met-Leu-Phe on human polymorphonuclear leukocytes. FEBS Lett 132:85-88.
    • (1981) FEBS Lett , vol.132 , pp. 85-88
    • Cost, H.1    Gespach, C.2    Abita, J.P.3
  • 7
    • 0141992805 scopus 로고    scopus 로고
    • Three-dimensional models for beta-adrenergic receptor complexes with agonists and antagonists
    • Furse KE and Lybrand TP (2003) Three-dimensional models for beta-adrenergic receptor complexes with agonists and antagonists. J Med Chem 46:4450-4462.
    • (2003) J Med Chem , vol.46 , pp. 4450-4462
    • Furse, K.E.1    Lybrand, T.P.2
  • 8
    • 0027138232 scopus 로고
    • Cellular signaling: New insights into the action of the plant growth hormone auxin
    • Goldsmith MH (1993) Cellular signaling: new insights into the action of the plant growth hormone auxin. Proc Natl Acad Sci USA 90:11442-11445.
    • (1993) Proc Natl Acad Sci USA , vol.90 , pp. 11442-11445
    • Goldsmith, M.H.1
  • 9
    • 0037251708 scopus 로고    scopus 로고
    • Inflammatory cells in asthma: Mechanisms and implications for therapy
    • Hamid Q, Tulic MK, Liu MC, and Moqbel R (2003) Inflammatory cells in asthma: mechanisms and implications for therapy. J Allergy Clin Immunol 111:S5-S12; discussion S12-S17.
    • (2003) J Allergy Clin Immunol , vol.111
    • Hamid, Q.1    Tulic, M.K.2    Liu, M.C.3    Moqbel, R.4
  • 10
    • 0037622765 scopus 로고    scopus 로고
    • Expression and molecular pharmacology of the mouse CRTH2 Receptor
    • Hata AN, Zent R, Breyer MD, and Breyer RM (2003) Expression and molecular pharmacology of the mouse CRTH2 Receptor. J Pharmacol Exp Ther 306:463-470.
    • (2003) J Pharmacol Exp Ther , vol.306 , pp. 463-470
    • Hata, A.N.1    Zent, R.2    Breyer, M.D.3    Breyer, R.M.4
  • 12
    • 0036467346 scopus 로고    scopus 로고
    • Cutting edge: Agonistic effect of indomethacin on a prostaglandin D(2) receptor, CRTH2
    • Hirai H, Tanaka K, Takano S, Ichimasa M, Nakamura M, and Nagata K (2002) Cutting edge: agonistic effect of indomethacin on a prostaglandin D(2) receptor, CRTH2. J Immunol 168:981-985.
    • (2002) J Immunol , vol.168 , pp. 981-985
    • Hirai, H.1    Tanaka, K.2    Takano, S.3    Ichimasa, M.4    Nakamura, M.5    Nagata, K.6
  • 13
    • 0035862329 scopus 로고    scopus 로고
    • Prostaglandin D2 selectively induces chemotaxis in T helper type 2 cells, eosinophils and basophils via seven-transmembrane receptor CRTH2
    • Hirai H, Tanaka K, Yoshie O, Ogawa K, Kenmotsu K, Takamori Y, Ichimasa M, Sugamura K, Nakamura M, Takano S, et al. (2001) Prostaglandin D2 selectively induces chemotaxis in T helper type 2 cells, eosinophils and basophils via seven-transmembrane receptor CRTH2. J Exp Med 193:255-261.
    • (2001) J Exp Med , vol.193 , pp. 255-261
    • Hirai, H.1    Tanaka, K.2    Yoshie, O.3    Ogawa, K.4    Kenmotsu, K.5    Takamori, Y.6    Ichimasa, M.7    Sugamura, K.8    Nakamura, M.9    Takano, S.10
  • 14
    • 0034681109 scopus 로고    scopus 로고
    • Biochemically based design of cyclooxygenase-2 (COX-2) inhibitors: Facile conversion of nonsteroidal antiinflammatory drugs to potent and highly selective COX-2 inhibitors
    • Kalgutkar AS, Crews BC, Rowlinson SW, Marnett AB, Kozak KR, Remmel RP, and Marnett LJ (2000a) Biochemically based design of cyclooxygenase-2 (COX-2) inhibitors: facile conversion of nonsteroidal antiinflammatory drugs to potent and highly selective COX-2 inhibitors. Proc Natl Acad Sci USA 97:925-930.
    • (2000) Proc Natl Acad Sci USA , vol.97 , pp. 925-930
    • Kalgutkar, A.S.1    Crews, B.C.2    Rowlinson, S.W.3    Marnett, A.B.4    Kozak, K.R.5    Remmel, R.P.6    Marnett, L.J.7
  • 15
    • 0034721194 scopus 로고    scopus 로고
    • Ester and amide derivatives of the nonsteroidal antiinflammatory drug, indomethacin, as selective cyclooxygenase-2 inhibitors
    • Kalgutkar AS, Marnett AB, Crews BC, Remmel RP, and Marnett LJ (2000b) Ester and amide derivatives of the nonsteroidal antiinflammatory drug, indomethacin, as selective cyclooxygenase-2 inhibitors. J Med Chem 43:2860-2870.
    • (2000) J Med Chem , vol.43 , pp. 2860-2870
    • Kalgutkar, A.S.1    Marnett, A.B.2    Crews, B.C.3    Remmel, R.P.4    Marnett, L.J.5
  • 16
    • 0031013395 scopus 로고    scopus 로고
    • Peroxisome proliferator-activated receptors alpha and gamma are activated by indomethacin and other non-steroidal anti-inflammatory drugs
    • Lehmann JM, Lenhard JM, Oliver BB, Ringold GM, and Kliewer SA (1997) Peroxisome proliferator-activated receptors alpha and gamma are activated by indomethacin and other non-steroidal anti-inflammatory drugs. J Biol Chem 272:3406-3410.
    • (1997) J Biol Chem , vol.272 , pp. 3406-3410
    • Lehmann, J.M.1    Lenhard, J.M.2    Oliver, B.B.3    Ringold, G.M.4    Kliewer, S.A.5
  • 18
    • 1642357433 scopus 로고    scopus 로고
    • Crystal structures of prostaglandin D(2) 11-ketoreductase (AKR1C3) in complex with the nonsteroidal anti-inflammatory drugs flufenamic acid and indomethacin
    • Levering AL, Ride JP, Bunce CM, Desmond JC, Cummings SM, and White SA (2004) Crystal structures of prostaglandin D(2) 11-ketoreductase (AKR1C3) in complex with the nonsteroidal anti-inflammatory drugs flufenamic acid and indomethacin. Cancer Res 64:1802-1810.
    • (2004) Cancer Res , vol.64 , pp. 1802-1810
    • Levering, A.L.1    Ride, J.P.2    Bunce, C.M.3    Desmond, J.C.4    Cummings, S.M.5    White, S.A.6
  • 19
    • 0034671926 scopus 로고    scopus 로고
    • Characterization of the binding site on the formyl peptide receptor using three receptor mutants and analogs of Met-Leu-Phe and Met-Met-Trp-Leu-Leu
    • Mills JS, Miettinen HM, Cummings D, and Jesaitis AJ (2000) Characterization of the binding site on the formyl peptide receptor using three receptor mutants and analogs of Met-Leu-Phe and Met-Met-Trp-Leu-Leu. J Biol Chem 275:39012-39017.
    • (2000) J Biol Chem , vol.275 , pp. 39012-39017
    • Mills, J.S.1    Miettinen, H.M.2    Cummings, D.3    Jesaitis, A.J.4
  • 20
    • 0021995184 scopus 로고
    • Some nonsteroidal antiinflammatory drugs inhibit the generation of superoxide anions by activated polymorphs by blocking ligand-receptor interactions
    • Minta JO and Williams MD (1985) Some nonsteroidal antiinflammatory drugs inhibit the generation of superoxide anions by activated polymorphs by blocking ligand-receptor interactions. J Rheumatol 12:751-757.
    • (1985) J Rheumatol , vol.12 , pp. 751-757
    • Minta, J.O.1    Williams, M.D.2
  • 22
    • 0032829392 scopus 로고    scopus 로고
    • CRTH2, an orphan receptor of T-helper-2-cells, is expressed on basophils and eosinophils and responds to mast cell-derived factor(s)
    • Nagata K, Hirai H, Tanaka K, Ogawa K, Aso T, Sugamura K, Nakamura M, and Takano S (1999a) CRTH2, an orphan receptor of T-helper-2-cells, is expressed on basophils and eosinophils and responds to mast cell-derived factor(s). FEBS Lett 459:195-199.
    • (1999) FEBS Lett , vol.459 , pp. 195-199
    • Nagata, K.1    Hirai, H.2    Tanaka, K.3    Ogawa, K.4    Aso, T.5    Sugamura, K.6    Nakamura, M.7    Takano, S.8
  • 24
    • 0029665029 scopus 로고    scopus 로고
    • Effects of thromboxane A2 receptor antagonist (Bay u 3405) on nasal symptoms after antigen challenge in sensitized guinea pigs
    • Narita S, Asakura K, and Kataura A (1996) Effects of thromboxane A2 receptor antagonist (Bay u 3405) on nasal symptoms after antigen challenge in sensitized guinea pigs. Int Arch Allergy Immunol 109:161-166.
    • (1996) Int Arch Allergy Immunol , vol.109 , pp. 161-166
    • Narita, S.1    Asakura, K.2    Kataura, A.3
  • 25
    • 0029068823 scopus 로고
    • Selective coupling of prostaglandin E receptor EP3D to Gi and Gs through interaction of α-carboxylic acid of agonist and arginine residue of seventh transmembrane domain
    • Negishi M, Irie A, Sugimoto Y, Namba T, and Ichikawa A (1995) Selective coupling of prostaglandin E receptor EP3D to Gi and Gs through interaction of α-carboxylic acid of agonist and arginine residue of seventh transmembrane domain. J Biol Chem 270:16122-16127.
    • (1995) J Biol Chem , vol.270 , pp. 16122-16127
    • Negishi, M.1    Irie, A.2    Sugimoto, Y.3    Namba, T.4    Ichikawa, A.5
  • 26
    • 0023234590 scopus 로고
    • Diclofenac binding to human polymorphonuclear neutrophils: Effect on respiratory burst and N-formylated peptide binding
    • Perianin A, Gougerot-Pocidalo MA, Giroud JP, and Hakim J (1987) Diclofenac binding to human polymorphonuclear neutrophils: effect on respiratory burst and N-formylated peptide binding. Biochem Pharmacol 36:2609-2615.
    • (1987) Biochem Pharmacol , vol.36 , pp. 2609-2615
    • Perianin, A.1    Gougerot-Pocidalo, M.A.2    Giroud, J.P.3    Hakim, J.4
  • 27
    • 10644285687 scopus 로고    scopus 로고
    • Molecular basis of the time-dependent inhibition of cyclooxygenases by indomethacin
    • Prusakiewicz JJ, Felts AS, Mackenzie BS, and Marnett LJ (2004) Molecular basis of the time-dependent inhibition of cyclooxygenases by indomethacin. Biochemistry 43:15439-15445
    • (2004) Biochemistry , vol.43 , pp. 15439-15445
    • Prusakiewicz, J.J.1    Felts, A.S.2    Mackenzie, B.S.3    Marnett, L.J.4
  • 29
    • 0024553236 scopus 로고
    • Effects of non-steroidal anti-inflammatory drugs on isolated human polymorphonuclear leukocytes (PMN): Chemotaxis, superoxide production, degranulation and N-formyl-L-methionyl-L-leucyl-L-phenylalanine (FMLP) receptor binding
    • Shelly J and Hoff SF (1989) Effects of non-steroidal anti-inflammatory drugs on isolated human polymorphonuclear leukocytes (PMN): chemotaxis, superoxide production, degranulation and N-formyl-L-methionyl-L-leucyl-L- phenylalanine (FMLP) receptor binding. Gen Pharmacol 20:329-334.
    • (1989) Gen Pharmacol , vol.20 , pp. 329-334
    • Shelly, J.1    Hoff, S.F.2
  • 30
    • 14944345070 scopus 로고
    • Synthesis and biological activity of some indomethacin analogs
    • Garattini S and Dukes MNG eds Excerpta Medica Foundation, Milan, Italy
    • Shen TY (1964) Synthesis and biological activity of some indomethacin analogs, in International Symposium on Non-Steroidal Anti-Inflammatory Drugs (Garattini S and Dukes MNG eds) pp 13-20, Excerpta Medica Foundation, Milan, Italy.
    • (1964) International Symposium on Non-Steroidal Anti-Inflammatory Drugs , pp. 13-20
    • Shen, T.Y.1
  • 32
    • 0022525558 scopus 로고
    • Effects of ibuprofen on chemotactic peptide-receptor binding and granulocyte response
    • Skubitz KM and Hammerschmidt DE (1986) Effects of ibuprofen on chemotactic peptide-receptor binding and granulocyte response. Biochem Pharmacol 35:3349-3354.
    • (1986) Biochem Pharmacol , vol.35 , pp. 3349-3354
    • Skubitz, K.M.1    Hammerschmidt, D.E.2
  • 34
    • 0037382497 scopus 로고    scopus 로고
    • An orally bioavailable small molecule antagonist of CRTH2, ramatroban (BAY u3405), inhibits prostaglandin D2-induced eosinophil migration in vitro
    • Sugimoto H, Shichijo M, Iino T, Manabe Y, Watanabe A, Shimazaki M, Gantner F, and Bacon KB (2003) An orally bioavailable small molecule antagonist of CRTH2, ramatroban (BAY u3405), inhibits prostaglandin D2-induced eosinophil migration in vitro. J Pharmacol Exp Ther 305:347-352.
    • (2003) J Pharmacol Exp Ther , vol.305 , pp. 347-352
    • Sugimoto, H.1    Shichijo, M.2    Iino, T.3    Manabe, Y.4    Watanabe, A.5    Shimazaki, M.6    Gantner, F.7    Bacon, K.B.8
  • 38
    • 0020031939 scopus 로고
    • Inhibition by nonsteroidal antiinflammatory drugs of luminol-dependent human-granulocyte chemiluminescence and [3H]FMLP binding. Effect of sulindac sulfide, indomethacin metabolite and optical enantiomers (+) and (-) MK830
    • Van Dyke K, Peden D, Van Dyke C, Jones G, Castranova V, and Ma J (1982) Inhibition by nonsteroidal antiinflammatory drugs of luminol-dependent human-granulocyte chemiluminescence and [3H]FMLP binding. Effect of sulindac sulfide, indomethacin metabolite and optical enantiomers (+) and (-) MK830. Inflammation 6:113-125.
    • (1982) Inflammation , vol.6 , pp. 113-125
    • Van Dyke, K.1    Peden, D.2    Van Dyke, C.3    Jones, G.4    Castranova, V.5    Ma, J.6
  • 39
    • 0027267429 scopus 로고
    • Determination of indomethacin, its metabolites and their glucuronides in human plasma and urine by means of direct gradient high-performance liquid chromatographic analysis. Preliminary pharmacokinetics and effect of probenecid
    • Vree TB, van den Biggelaar-Martea M, and Verwey-van Wissen CP (1993) Determination of indomethacin, its metabolites and their glucuronides in human plasma and urine by means of direct gradient high-performance liquid chromatographic analysis. Preliminary pharmacokinetics and effect of probenecid. J Chromatogr 616:271-282.
    • (1993) J Chromatogr , vol.616 , pp. 271-282
    • Vree, T.B.1    Van Den Biggelaar-Martea, M.2    Verwey-van Wissen, C.P.3
  • 40
    • 0033575760 scopus 로고    scopus 로고
    • Malignant transformation and antineoplastic actions of nonsteroidal antiinflammatory drugs (NSAIDs) on cyclooxygenase-null embryo fibroblasts
    • Zhang X, Morham SG, Langenbach R, and Young DA (1999) Malignant transformation and antineoplastic actions of nonsteroidal antiinflammatory drugs (NSAIDs) on cyclooxygenase-null embryo fibroblasts. J Exp Med 190:451-459.
    • (1999) J Exp Med , vol.190 , pp. 451-459
    • Zhang, X.1    Morham, S.G.2    Langenbach, R.3    Young, D.A.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.