메뉴 건너뛰기




Volumn 5, Issue 1, 2009, Pages 91-106

Structure-activity relationships of anthraquinone derivatives derived from bromaminic acid as inhibitors of ectonucleoside triphosphate diphosphohydrolases (E-NTPDases)

Author keywords

Anthraquinone; E NTPDase; Inhibitor; Reactive blue 2; Synthesis

Indexed keywords


EID: 60449095619     PISSN: 15739538     EISSN: 15739546     Source Type: Journal    
DOI: 10.1007/s11302-008-9103-5     Document Type: Article
Times cited : (61)

References (52)
  • 1
    • 34248576759 scopus 로고    scopus 로고
    • Physiology and pathophysiology of purinergic neurotransmission
    • Burnstock G (2007) Physiology and pathophysiology of purinergic neurotransmission. Physiol Rev 87:659-797
    • (2007) Physiol Rev , vol.87 , pp. 659-797
    • Burnstock, G.1
  • 2
    • 0033152549 scopus 로고    scopus 로고
    • Two novel families of ectonucleotidases: Molecular structures, catalytic properties and a search for function
    • Zimmermann H (1999) Two novel families of ectonucleotidases: Molecular structures, catalytic properties and a search for function. Trends Pharmacol Sci 20:231-236
    • (1999) Trends Pharmacol Sci , vol.20 , pp. 231-236
    • Zimmermann, H.1
  • 4
    • 0033766981 scopus 로고    scopus 로고
    • Extracellular metabolism of ATP and other nucleotides
    • Zimmermann H (2000) Extracellular metabolism of ATP and other nucleotides. Naunyn Schmiedebergs Arch Pharmacol 362:299-309
    • (2000) Naunyn Schmiedebergs Arch Pharmacol , vol.362 , pp. 299-309
    • Zimmermann, H.1
  • 5
    • 33747410178 scopus 로고    scopus 로고
    • Ectonucleotidases in the nervous system
    • Zimmermann H (2006) Ectonucleotidases in the nervous system. Novartis Found Symp 276:113-128
    • (2006) Novartis Found Symp , vol.276 , pp. 113-128
    • Zimmermann, H.1
  • 6
    • 0035033156 scopus 로고    scopus 로고
    • Ectonucleotidases: Some recent developments and a note on nomenclature
    • Zimmermann H (2001) Ectonucleotidases: Some recent developments and a note on nomenclature. Drug Devt Res 52:44-56
    • (2001) Drug Devt Res , vol.52 , pp. 44-56
    • Zimmermann, H.1
  • 7
    • 33745047764 scopus 로고    scopus 로고
    • Molecular cloning and characterization of expressed human ectonucleoside triphosphate diphosphohydrolase 8 (E-NTPDase8) and its soluble extracellular domain
    • Knowles AF, Li C (2006) Molecular cloning and characterization of expressed human ectonucleoside triphosphate diphosphohydrolase 8 (E-NTPDase8) and its soluble extracellular domain. Biochemistry 45:7323-7333
    • (2006) Biochemistry , vol.45 , pp. 7323-7333
    • Knowles, A.F.1    Li, C.2
  • 9
    • 0033575280 scopus 로고    scopus 로고
    • CD39-L4 is a secreted human apyrase, specific for the hydrolysis of nucleoside diphosphates
    • Mulero JJ, Yeung G, Nelken ST, Ford JE (1999) CD39-L4 is a secreted human apyrase, specific for the hydrolysis of nucleoside diphosphates. J Biol Chem 274:20064-20067
    • (1999) J Biol Chem , vol.274 , pp. 20064-20067
    • Mulero, J.J.1    Yeung, G.2    Nelken, S.T.3    Ford, J.E.4
  • 10
    • 0042928440 scopus 로고    scopus 로고
    • Purification and characterization of NTPDase1 (ecto-apyrase) and NTPDase2 (ecto-ATPase) from porcine brain cortex synaptosomes
    • Kukulski F, Komoszynski M (2003) Purification and characterization of NTPDase1 (ecto-apyrase) and NTPDase2 (ecto-ATPase) from porcine brain cortex synaptosomes. Eur J Biochem 270:3447-3454
    • (2003) Eur J Biochem , vol.270 , pp. 3447-3454
    • Kukulski, F.1    Komoszynski, M.2
  • 11
    • 0034831210 scopus 로고    scopus 로고
    • The C-terminal cysteine-rich region dictates specific catalytic properties in chimeras of the ectonucleotidases NTPDase1 and NTPDase2
    • Heine P, Braun N, Sevigny J, Robson SC, Servos J, Zimmermann H (2001) The C-terminal cysteine-rich region dictates specific catalytic properties in chimeras of the ectonucleotidases NTPDase1 and NTPDase2. Eur J Biochem 268:364-373
    • (2001) Eur J Biochem , vol.268 , pp. 364-373
    • Heine, P.1    Braun, N.2    Sevigny, J.3    Robson, S.C.4    Servos, J.5    Zimmermann, H.6
  • 12
    • 33845702620 scopus 로고    scopus 로고
    • The structure of the nucleoside triphosphate diphosphydrolases (NTPDases) as revealed by mutagenic and computational modelin analyses
    • Kirley TL, Crawford PA, Smith TM (2006) The structure of the nucleoside triphosphate diphosphydrolases (NTPDases) as revealed by mutagenic and computational modelin analyses. Purinergic Signalling 2:379-389
    • (2006) Purinergic Signalling , vol.2 , pp. 379-389
    • Kirley, T.L.1    Crawford, P.A.2    Smith, T.M.3
  • 13
    • 0033563017 scopus 로고    scopus 로고
    • Functional characterization of rat ecto-ATPase and ecto-ATP diphosphohydrolase after heterologous expression in CHO cells
    • Heine P, Braun N, Heilbronn A, Zimmermann H (1999) Functional characterization of rat ecto-ATPase and ecto-ATP diphosphohydrolase after heterologous expression in CHO cells. Eur J Biochem 262:102-107
    • (1999) Eur J Biochem , vol.262 , pp. 102-107
    • Heine, P.1    Braun, N.2    Heilbronn, A.3    Zimmermann, H.4
  • 14
    • 0038070596 scopus 로고    scopus 로고
    • Determination of native oligomeric state and substrate specificity of rat NTPDase1 and NTPDase2 after heterologous expression in Xenopus oocytes
    • Failer BU, Aschrafi A, Schmalzing G, Zimmermann H (2003) Determination of native oligomeric state and substrate specificity of rat NTPDase1 and NTPDase2 after heterologous expression in Xenopus oocytes. Eur J Biochem 270:1802-1809
    • (2003) Eur J Biochem , vol.270 , pp. 1802-1809
    • Failer, B.U.1    Aschrafi, A.2    Schmalzing, G.3    Zimmermann, H.4
  • 15
    • 33846436678 scopus 로고    scopus 로고
    • The E-NTPDase family of ectonucleotidases: Structure-function relationships and pathophysiological significance
    • Robson SC, Sévigny J, Zimmermann H (2006) The E-NTPDase family of ectonucleotidases: Structure-function relationships and pathophysiological significance. Purinergic Signalling 2:409-430
    • (2006) Purinergic Signalling , vol.2 , pp. 409-430
    • Robson, S.C.1    Sévigny, J.2    Zimmermann, H.3
  • 16
    • 0037089425 scopus 로고    scopus 로고
    • Differential catalytic properties and vascular topography of murine nucleoside triphosphate diphosphohydrolase 1 (NTPDase1) and NTPDase2 have implications for thromboregulation
    • Sévigny J, Sundberg C, Braun N, Guckelberger O, Csizmadia E, Qawi I, Imai M, Zimmermann H, Robson SC (2002) Differential catalytic properties and vascular topography of murine nucleoside triphosphate diphosphohydrolase 1 (NTPDase1) and NTPDase2 have implications for thromboregulation. Blood 99:801-2809
    • (2002) Blood , vol.99 , pp. 801-2809
    • Sévigny, J.1    Sundberg, C.2    Braun, N.3    Guckelberger, O.4    Csizmadia, E.5    Qawi, I.6    Imai, M.7    Zimmermann, H.8    Robson, S.C.9
  • 18
    • 36849092887 scopus 로고    scopus 로고
    • The ectonucleotidases alkaline phosphatase and nucleoside triphosphate diphosphohydrolase 2 are associated with subsets of progenitor cell populations in the mouse embryonic, postnatal and adult neurogenic zones
    • Langer D, Ikehara Y, Takebayashi H, Hawkes R, Zimmermann H (2007) The ectonucleotidases alkaline phosphatase and nucleoside triphosphate diphosphohydrolase 2 are associated with subsets of progenitor cell populations in the mouse embryonic, postnatal and adult neurogenic zones. Neuroscience 150:863-879
    • (2007) Neuroscience , vol.150 , pp. 863-879
    • Langer, D.1    Ikehara, Y.2    Takebayashi, H.3    Hawkes, R.4    Zimmermann, H.5
  • 19
    • 0141540462 scopus 로고    scopus 로고
    • Enzymatic and transcriptional regulation of human ecto-ATPase/E-NTPDase 2
    • Knowles AF, Chiang W-C (2003) Enzymatic and transcriptional regulation of human ecto-ATPase/E-NTPDase 2. Arch Biochem Biophys 418:217-227
    • (2003) Arch Biochem Biophys , vol.418 , pp. 217-227
    • Knowles, A.F.1    Chiang, W.-C.2
  • 20
    • 33846677010 scopus 로고    scopus 로고
    • Nucleotide metabolizing ecto-enzymes in Walker 256 tumor cells: Molecular identification, kinetic characterization and biochemical properties
    • Buffon A, Ribeiro VB, Wink MR, Casali EA, Sarkis JJ (2007) Nucleotide metabolizing ecto-enzymes in Walker 256 tumor cells: Molecular identification, kinetic characterization and biochemical properties. Life Sci 80:950-958
    • (2007) Life Sci , vol.80 , pp. 950-958
    • Buffon, A.1    Ribeiro, V.B.2    Wink, M.R.3    Casali, E.A.4    Sarkis, J.J.5
  • 21
    • 31144457368 scopus 로고    scopus 로고
    • Immunolocalization of ecto-nucleoside triphosphate for modulation of multiple homeostatic systems including feeding and sleep-wake behaviours
    • Belcher SM, Zsarnovszky A, Crawford PA, Hemani H, Spurling L, Kirley TL (2006) Immunolocalization of ecto-nucleoside triphosphate for modulation of multiple homeostatic systems including feeding and sleep-wake behaviours. Neuroscience 137:1331-1346
    • (2006) Neuroscience , vol.137 , pp. 1331-1346
    • Belcher, S.M.1    Zsarnovszky, A.2    Crawford, P.A.3    Hemani, H.4    Spurling, L.5    Kirley, T.L.6
  • 22
    • 33746611096 scopus 로고    scopus 로고
    • Noise-induced up-regulation of NTPDase3 expression in the rat cochlea: Implications for auditory transmission and cochlear protection
    • Vlajkovic SM, Vinayagamoorthy A, Thorne PR, Robson SC, Wang CJ, Housley GD (2006) Noise-induced up-regulation of NTPDase3 expression in the rat cochlea: Implications for auditory transmission and cochlear protection. Brain Res 1104:55-63
    • (2006) Brain Res , vol.1104 , pp. 55-63
    • Vlajkovic, S.M.1    Vinayagamoorthy, A.2    Thorne, P.R.3    Robson, S.C.4    Wang, C.J.5    Housley, G.D.6
  • 24
    • 0030221110 scopus 로고    scopus 로고
    • Modulation of purinergic neurotransmission by ecto-ATPase
    • Kennedy C, Westfall TD, Sneddon P (1996) Modulation of purinergic neurotransmission by ecto-ATPase. Semin Neurosci 8:195-199
    • (1996) Semin Neurosci , vol.8 , pp. 195-199
    • Kennedy, C.1    Westfall, T.D.2    Sneddon, P.3
  • 25
    • 0033392249 scopus 로고    scopus 로고
    • Inhibition of rat parotid ecto-ATPase activity
    • Dowd FJ, Li LS, Zeng W (1999) Inhibition of rat parotid ecto-ATPase activity. Arch Oral Biol 44:1055-1062
    • (1999) Arch Oral Biol , vol.44 , pp. 1055-1062
    • Dowd, F.J.1    Li, L.S.2    Zeng, W.3
  • 26
    • 1642456586 scopus 로고    scopus 로고
    • Effect of the ecto-ATPase inhibitor, ARL 67156, on the bovine chromaffin cell response to ATP
    • Drakulich DA, Spellmon C, Hexum TD (2004) Effect of the ecto-ATPase inhibitor, ARL 67156, on the bovine chromaffin cell response to ATP. Eur J Pharmacol 485:137-140
    • (2004) Eur J Pharmacol , vol.485 , pp. 137-140
    • Drakulich, D.A.1    Spellmon, C.2    Hexum, T.D.3
  • 27
    • 29744434583 scopus 로고    scopus 로고
    • A capillary electrophoresis method for the characterization of ecto-nucleoside triphosphate diphosphohydrolases (NTPDases) and the analysis of inhibitors by in-capillary enzymatic microreaction
    • Iqbal J, Vollmayer P, Braun N, Zimmermann H, Müller CE (2005) A capillary electrophoresis method for the characterization of ecto-nucleoside triphosphate diphosphohydrolases (NTPDases) and the analysis of inhibitors by in-capillary enzymatic microreaction. Purinergic Signalling 1:349-358
    • (2005) Purinergic Signalling , vol.1 , pp. 349-358
    • Iqbal, J.1    Vollmayer, P.2    Braun, N.3    Zimmermann, H.4    Müller, C.E.5
  • 28
    • 34548319100 scopus 로고    scopus 로고
    • Specificity of the ecto-ATPase inhibitor ARL 67156 on human and mouse ectonucleotidases
    • Lévesque SA, Lavoie EG, Lecka J, Bigonnesse F, Sévigny J (2007) Specificity of the ecto-ATPase inhibitor ARL 67156 on human and mouse ectonucleotidases. Br J Pharmacol 152:141-150
    • (2007) Br J Pharmacol , vol.152 , pp. 141-150
    • Lévesque, S.A.1    Lavoie, E.G.2    Lecka, J.3    Bigonnesse, F.4    Sévigny, J.5
  • 29
    • 0034214125 scopus 로고    scopus 로고
    • Novel inhibitors of nucleoside triphosphate diphosphohydrolases: Chemical synthesis and biochemical and pharmacological characterizations
    • Gendron FP, Halbfinger E, Fischer B, Duval M, D'Orléans-Juste P, Beaudoin AR (2000) Novel inhibitors of nucleoside triphosphate diphosphohydrolases: Chemical synthesis and biochemical and pharmacological characterizations. J Med Chem 43:2239-2247
    • (2000) J Med Chem , vol.43 , pp. 2239-2247
    • Gendron, F.P.1    Halbfinger, E.2    Fischer, B.3    Duval, M.4    D'Orléans-Juste, P.5    Beaudoin, A.R.6
  • 31
    • 1242340484 scopus 로고    scopus 로고
    • Characterization of an ectonucleoside triphosphate diphosphohydrolase 1 activity in alkaline phosphatase-depleted rat osseous membranes: Possible functional involvement in the calcification process
    • Demenis MA, Furriel RP, Leone FA (2003) Characterization of an ectonucleoside triphosphate diphosphohydrolase 1 activity in alkaline phosphatase-depleted rat osseous membranes: Possible functional involvement in the calcification process. Biochem Biophys Acta 1646:216-225
    • (2003) Biochem Biophys Acta , vol.1646 , pp. 216-225
    • Demenis, M.A.1    Furriel, R.P.2    Leone, F.A.3
  • 32
    • 0028148845 scopus 로고
    • Pharmacological analysis of ecto-ATPase inhibition: Evidence for combined enzyme inhibition and receptor antagonism in P2X-purinoceptor ligands
    • Crack BE, Beukers MW, McKechnie KC, Ijzerman AP, Leff P (1994) Pharmacological analysis of ecto-ATPase inhibition: Evidence for combined enzyme inhibition and receptor antagonism in P2X-purinoceptor ligands. Br J Pharmacol 113:1432-1438
    • (1994) Br J Pharmacol , vol.113 , pp. 1432-1438
    • Crack, B.E.1    Beukers, M.W.2    McKechnie, K.C.3    Ijzerman, A.P.4    Leff, P.5
  • 33
    • 0029658866 scopus 로고    scopus 로고
    • P2-purinoceptor antagonists: III. Blockade of P2-purinoceptor subtypes and ecto-nucleotidases by compounds related to suramin
    • Bültmann R, Wittenburg H, Pause B, Kurz G, Nickel P, Starke K (1996) P2-purinoceptor antagonists: III. Blockade of P2-purinoceptor subtypes and ecto-nucleotidases by compounds related to suramin. Naunyn Schmiedebergs Arch Pharmacol 354:498-504
    • (1996) Naunyn Schmiedebergs Arch Pharmacol , vol.354 , pp. 498-504
    • Bültmann, R.1    Wittenburg, H.2    Pause, B.3    Kurz, G.4    Nickel, P.5    Starke, K.6
  • 34
    • 0029658871 scopus 로고    scopus 로고
    • P2-purinoceptor antagonists: II. Blockade of P2-purinoceptor subtypes and ecto-nucleotidases by compounds related to Evans blue and trypan blue
    • Wittenburg H, Bültmann R, Pause B, Ganter C, Kurz G, Starke K (1996) P2-purinoceptor antagonists: II. Blockade of P2-purinoceptor subtypes and ecto-nucleotidases by compounds related to Evans blue and trypan blue. Naunyn Schmiedebergs Arch Pharmacol 354:491-497
    • (1996) Naunyn Schmiedebergs Arch Pharmacol , vol.354 , pp. 491-497
    • Wittenburg, H.1    Bültmann, R.2    Pause, B.3    Ganter, C.4    Kurz, G.5    Starke, K.6
  • 35
    • 0029554726 scopus 로고
    • Inhibition of purified chicken gizzard smooth muscle ecto-ATPase by P2 purinoceptor antagonists
    • Stout JG, Kirley TL (1995) Inhibition of purified chicken gizzard smooth muscle ecto-ATPase by P2 purinoceptor antagonists. Biochem Mol Biol Int 36:927-934
    • (1995) Biochem Mol Biol Int , vol.36 , pp. 927-934
    • Stout, J.G.1    Kirley, T.L.2
  • 36
    • 0028884840 scopus 로고
    • Reactive red 2: A P2y-selective purinoceptor antagonist and an inhibitor of ecto-nucleotidase
    • Bültmann R, Starke K (1995) Reactive red 2: A P2y-selective purinoceptor antagonist and an inhibitor of ecto-nucleotidase. Naunyn Schmiedebergs Arch Pharmacol 352:477-482
    • (1995) Naunyn Schmiedebergs Arch Pharmacol , vol.352 , pp. 477-482
    • Bültmann, R.1    Starke, K.2
  • 37
    • 0031930227 scopus 로고    scopus 로고
    • P2-receptor antagonists: IV. Blockade of P2-receptor subtypes and ecto-nucleotidases by compounds related to reactive blue 2
    • Tuluc F, Bültmann R, Glänzel M, Frahm AW, Starke K (1998) P2-receptor antagonists: IV. Blockade of P2-receptor subtypes and ecto-nucleotidases by compounds related to reactive blue 2. Naunyn Schmiedebergs Arch Pharmacol 357:111-120
    • (1998) Naunyn Schmiedebergs Arch Pharmacol , vol.357 , pp. 111-120
    • Tuluc, F.1    Bültmann, R.2    Glänzel, M.3    Frahm, A.W.4    Starke, K.5
  • 39
    • 0030474864 scopus 로고    scopus 로고
    • Inhibition of ecto-ATPase by PPADS, suramin and reactive blue in endothelial cells, C6 glioma cells and RAW 264.7 macrophages
    • Chen BC, Lee CM, Lin WW (1996) Inhibition of ecto-ATPase by PPADS, suramin and reactive blue in endothelial cells, C6 glioma cells and RAW 264.7 macrophages. Br J Pharmacol 119:1628-1634
    • (1996) Br J Pharmacol , vol.119 , pp. 1628-1634
    • Chen, B.C.1    Lee, C.M.2    Lin, W.W.3
  • 40
    • 33750523406 scopus 로고    scopus 로고
    • Polyoxometalates - A new class of potent ecto-nucleoside triphosphate diphosphohydrolase (NTPDase) inhibitors
    • Müller CE, Iqbal J, Baqi Y, Zimmermann H, Röllich A, Stephan H (2006) Polyoxometalates - a new class of potent ecto-nucleoside triphosphate diphosphohydrolase (NTPDase) inhibitors. Bioorg Med Chem Lett 16:5943-5947
    • (2006) Bioorg Med Chem Lett , vol.16 , pp. 5943-5947
    • Müller, C.E.1    Iqbal, J.2    Baqi, Y.3    Zimmermann, H.4    Röllich, A.5    Stephan, H.6
  • 43
    • 34249874596 scopus 로고    scopus 로고
    • Role of P2 purinergic receptors in synaptic transmission under normoxic and ischaemic conditions in the CA1 region of rat hippocampal slices
    • Coppi E, Pugliese AM, Stephan H, Müller CE, Pedata F (2007) Role of P2 purinergic receptors in synaptic transmission under normoxic and ischaemic conditions in the CA1 region of rat hippocampal slices. Purinergic Signalling 3:203-219
    • (2007) Purinergic Signalling , vol.3 , pp. 203-219
    • Coppi, E.1    Pugliese, A.M.2    Stephan, H.3    Müller, C.E.4    Pedata, F.5
  • 46
    • 34147103330 scopus 로고    scopus 로고
    • Rapid and efficient microwave-assisted copper(0)-catalyzed Ullmann coupling reaction
    • Baqi Y, Müller CE (2007) Rapid and efficient microwave-assisted copper(0)-catalyzed Ullmann coupling reaction. Org Lett 9:1271-1274
    • (2007) Org Lett , vol.9 , pp. 1271-1274
    • Baqi, Y.1    Müller, C.E.2
  • 47
    • 37049167376 scopus 로고
    • The effect of alkyl groups on the properties of anthraquinone and fluorescein dyes
    • DOI 10.1039/JR9360001838
    • Harris RM, Mariott GJ, Smith JC (1936) The effect of alkyl groups on the properties of anthraquinone and fluorescein dyes. J Chem Soc 1838-1842. DOI 10.1039/JR9360001838
    • (1936) J Chem Soc , pp. 1838-1842
    • Harris, R.M.1    Mariott, G.J.2    Smith, J.C.3
  • 48
    • 17144445333 scopus 로고    scopus 로고
    • Members of the acid blue 129 family as potent and selective P2Y-receptor antagonists
    • Glänzel M, Bültmann R, Starke K, Frahm AW (2003) Members of the acid blue 129 family as potent and selective P2Y-receptor antagonists. Drug Dev Res 59:63-71
    • (2003) Drug Dev Res , vol.59 , pp. 63-71
    • Glänzel, M.1    Bültmann, R.2    Starke, K.3    Frahm, A.W.4
  • 49
    • 85021566586 scopus 로고
    • Acidic derivatives of anthraquinone. I. Influence of substituents in the phenylamine radical of anthraquinone derivatives on their properties
    • Bessubetz MK, Rozina VS (1948) Acidic derivatives of anthraquinone. I. Influence of substituents in the phenylamine radical of anthraquinone derivatives on their properties. Zh Prikl Khim 21:1152-1161
    • (1948) Zh Prikl Khim , vol.21 , pp. 1152-1161
    • Bessubetz, M.K.1    Rozina, V.S.2
  • 50
    • 60449099215 scopus 로고
    • Anthraquinone derivatives
    • I.G. Farbenindustrie AG French Patent FR 751236 19330829
    • I.G. Farbenindustrie AG (1933) Anthraquinone derivatives. French Patent FR 751236 19330829
    • (1933)
  • 52
    • 23844501100 scopus 로고    scopus 로고
    • Cloning and characterization of the ecto-nucleotidase NTPDase3 from rat brain: Predicted secondary structure and relation to other members of the E-NTPDase family and actin
    • Vorhoff T, Zimmermann H, Pelletier J, Sévigny J, Braun N (2005) Cloning and characterization of the ecto-nucleotidase NTPDase3 from rat brain: Predicted secondary structure and relation to other members of the E-NTPDase family and actin. Purinergic Signalling 1:259-270
    • (2005) Purinergic Signalling , vol.1 , pp. 259-270
    • Vorhoff, T.1    Zimmermann, H.2    Pelletier, J.3    Sévigny, J.4    Braun, N.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.