메뉴 건너뛰기




Volumn 55, Issue 8, 2012, Pages 3792-3803

Structure-activity relationship of nonacidic quinazolinone inhibitors of human microsomal prostaglandin synthase 1 (mPGES 1)

Author keywords

[No Author keywords available]

Indexed keywords

AF 3442; FR 20; ICOSANOID; MF 63; PF 9184; PROSTAGLANDIN SYNTHASE; PROSTAGLANDIN SYNTHASE INHIBITOR; QUINAZOLINONE DERIVATIVE; UNCLASSIFIED DRUG; YS 121;

EID: 84860294771     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm201687d     Document Type: Article
Times cited : (53)

References (45)
  • 1
    • 0034692689 scopus 로고    scopus 로고
    • Regulation of prostaglandin E2 biosynthesis by inducible membrane-associated prostaglandin E2 synthase that acts in concert with cyclooxygenase-2
    • Murakami, M.; Naraba, H.; Tanioka, T.; Semmyo, N.; Nakatani, Y.; Kojima, F.; Ikeda, T.; Fueki, M.; Ueno, A.; Oh, S.; Kudo, I. Regulation of prostaglandin E2 biosynthesis by inducible membrane-associated prostaglandin E2 synthase that acts in concert with cyclooxygenase-2 J. Biol. Chem. 2000, 275, 32783-32792
    • (2000) J. Biol. Chem. , vol.275 , pp. 32783-32792
    • Murakami, M.1    Naraba, H.2    Tanioka, T.3    Semmyo, N.4    Nakatani, Y.5    Kojima, F.6    Ikeda, T.7    Fueki, M.8    Ueno, A.9    Oh, S.10    Kudo, I.11
  • 4
    • 0242321826 scopus 로고    scopus 로고
    • Microsomal prostaglandin E synthase-1 is the central switch during immune-induced pyresis
    • DOI 10.1038/nn1137
    • Engblom, D.; Saha, S.; Engstrom, L.; Westman, M.; Audoly, L. P.; Jakobsson, P. J.; Blomqvist, A. Microsomal prostaglandin E synthase-1 is the central switch during immune-induced pyresis Nature Neurosci. 2003, 6, 1137-1138 (Pubitemid 37346030)
    • (2003) Nature Neuroscience , vol.6 , Issue.11 , pp. 1137-1138
    • Engblom, D.1    Saha, S.2    Engstrom, L.3    Westman, M.4    Audoly, L.P.5    Jakobsson, P.-J.6    Blomqvist, A.7
  • 6
    • 84860309503 scopus 로고    scopus 로고
    • Microsomal prostaglandin e synthase-1 in rheumatic diseases
    • Korotkova, M.; Jakobsson, P. J. Microsomal prostaglandin E synthase-1 in rheumatic diseases Front. Pharmacol. 2011, 1
    • (2011) Front. Pharmacol. , pp. 1
    • Korotkova, M.1    Jakobsson, P.J.2
  • 7
    • 68449096860 scopus 로고    scopus 로고
    • Nonsteroidal anti-inflammatory drugs: A critical review on current concepts applied to reduce gastrointestinal toxicity
    • Abdel-Tawab, M.; Zettl, H.; Schubert-Zsilavecz, M. Nonsteroidal anti-inflammatory drugs: a critical review on current concepts applied to reduce gastrointestinal toxicity Curr. Med. Chem. 2009, 16, 2042-2063
    • (2009) Curr. Med. Chem. , vol.16 , pp. 2042-2063
    • Abdel-Tawab, M.1    Zettl, H.2    Schubert-Zsilavecz, M.3
  • 8
    • 34548795534 scopus 로고    scopus 로고
    • Microsomal prostaglandin E2 synthase: A safer target than cyclooxygenases?
    • Timmers, L.; Pasterkamp, G.; de Kleijn, D. P. Microsomal prostaglandin E2 synthase: a safer target than cyclooxygenases? Mol. Interventions 2007, 7 (195-199) 180
    • (2007) Mol. Interventions , vol.7 , Issue.195-199 , pp. 180
    • Timmers, L.1    Pasterkamp, G.2    De Kleijn, D.P.3
  • 9
    • 80255132934 scopus 로고    scopus 로고
    • Prostaglandin E(2) produced by microsomal prostaglandin e synthase-1 regulates the onset and the maintenance of wakefulness
    • Takemiya, T. Prostaglandin E(2) produced by microsomal prostaglandin E synthase-1 regulates the onset and the maintenance of wakefulness Neurochem. Int. 2011, 59, 922-924
    • (2011) Neurochem. Int. , vol.59 , pp. 922-924
    • Takemiya, T.1
  • 10
    • 77953526527 scopus 로고    scopus 로고
    • Microsomal prostaglandin e synthase-1 and 5-lipoxygenase: Potential drug targets in cancer
    • Radmark, O.; Samuelsson, B. Microsomal prostaglandin E synthase-1 and 5-lipoxygenase: potential drug targets in cancer J. Intern. Med. 2010, 268, 5-14
    • (2010) J. Intern. Med. , vol.268 , pp. 5-14
    • Radmark, O.1    Samuelsson, B.2
  • 11
    • 33746068237 scopus 로고    scopus 로고
    • Is mPGES-1 a promising target for pain therapy?
    • DOI 10.1016/j.tips.2006.06.001, PII S0165614706001490
    • Scholich, K.; Geisslinger, G. Is mPGES-1 a promising target for pain therapy? Trends Pharmacol. Sci. 2006, 27, 399-401 (Pubitemid 44069583)
    • (2006) Trends in Pharmacological Sciences , vol.27 , Issue.8 , pp. 399-401
    • Scholich, K.1    Geisslinger, G.2
  • 12
    • 79551708807 scopus 로고    scopus 로고
    • Use of nonsteroidal antiinflammatory drugs: Is there a change in patient risk profile after withdrawal of rofecoxib?
    • Rahme, E.; Roussy, J. P.; Lafrance, J. P.; Nedjar, H.; Morin, S. Use of nonsteroidal antiinflammatory drugs: is there a change in patient risk profile after withdrawal of rofecoxib? J. Rheumatol. 2011, 38, 195-202
    • (2011) J. Rheumatol. , vol.38 , pp. 195-202
    • Rahme, E.1    Roussy, J.P.2    Lafrance, J.P.3    Nedjar, H.4    Morin, S.5
  • 13
    • 79551717207 scopus 로고    scopus 로고
    • Aspirin: Antiinflammatory drug of choice in 2011?
    • Tiliakos, A. M.; Conn, D. L. Aspirin: antiinflammatory drug of choice in 2011? J. Rheumatol. 2011, 38, 185-187
    • (2011) J. Rheumatol. , vol.38 , pp. 185-187
    • Tiliakos, A.M.1    Conn, D.L.2
  • 14
    • 80054927472 scopus 로고    scopus 로고
    • Identification and development of mPGES-1 inhibitors: Where we are at?
    • Chang, H. H.; Meuillet, E. J. Identification and development of mPGES-1 inhibitors: where we are at? Future Med. Chem. 2011, 3, 1909-1934
    • (2011) Future Med. Chem. , vol.3 , pp. 1909-1934
    • Chang, H.H.1    Meuillet, E.J.2
  • 15
    • 70349101232 scopus 로고    scopus 로고
    • Anti-inflammatory and analgesic activity of a novel inhibitor of microsomal prostaglandin e synthase-1 expression
    • Guerrero, M. D.; Aquino, M.; Bruno, I.; Riccio, R.; Terencio, M. C.; Paya, M. Anti-inflammatory and analgesic activity of a novel inhibitor of microsomal prostaglandin E synthase-1 expression Eur. J. Pharmacol. 2009, 620, 112-119
    • (2009) Eur. J. Pharmacol. , vol.620 , pp. 112-119
    • Guerrero, M.D.1    Aquino, M.2    Bruno, I.3    Riccio, R.4    Terencio, M.C.5    Paya, M.6
  • 18
    • 53849098967 scopus 로고    scopus 로고
    • MF63 [2-(6-chloro-1 H -phenanthro[9,10- d ]imidazol-2-yl)- isophthalonitrile], a selective microsomal prostaglandin e synthase-1 inhibitor, relieves pyresis and pain in preclinical models of inflammation
    • Xu, D.; Rowland, S. E.; Clark, P.; Giroux, A.; Cote, B.; Guiral, S.; Salem, M.; Ducharme, Y.; Friesen, R. W.; Methot, N.; Mancini, J.; Audoly, L.; Riendeau, D. MF63 [2-(6-chloro-1 H -phenanthro[9,10- d ]imidazol-2-yl)- isophthalonitrile], a selective microsomal prostaglandin E synthase-1 inhibitor, relieves pyresis and pain in preclinical models of inflammation J. Pharmacol. Exp. Ther. 2008, 326, 754-763
    • (2008) J. Pharmacol. Exp. Ther. , vol.326 , pp. 754-763
    • Xu, D.1    Rowland, S.E.2    Clark, P.3    Giroux, A.4    Cote, B.5    Guiral, S.6    Salem, M.7    Ducharme, Y.8    Friesen, R.W.9    Methot, N.10    Mancini, J.11    Audoly, L.12    Riendeau, D.13
  • 19
    • 79957492550 scopus 로고    scopus 로고
    • Identification of 2-mercaptohexanoic acids as dual inhibitors of 5-lipoxygenase and microsomal prostaglandin E(2) synthase-1
    • Greiner, C.; Zettl, H.; Koeberle, A.; Pergola, C.; Northoff, H.; Schubert-Zsilavecz, M.; Werz, O. Identification of 2-mercaptohexanoic acids as dual inhibitors of 5-lipoxygenase and microsomal prostaglandin E(2) synthase-1 Bioorg. Med. Chem. 2011, 19, 3394-3401
    • (2011) Bioorg. Med. Chem. , vol.19 , pp. 3394-3401
    • Greiner, C.1    Zettl, H.2    Koeberle, A.3    Pergola, C.4    Northoff, H.5    Schubert-Zsilavecz, M.6    Werz, O.7
  • 20
    • 79960188500 scopus 로고    scopus 로고
    • Discovery and Biological Evaluation of a Novel Class of Dual Microsomal Prostaglandin E(2) Synthase-1/5-lipoxygenase Inhibitors Based on 2-[(4,6-Diphenethoxypyrimidin-2-yl)thio]hexanoic Acid
    • Hieke, M.; Greiner, C.; Dittrich, M.; Reisen, F.; Schneider, G.; Schubert-Zsilavecz, M.; Werz, O. Discovery and Biological Evaluation of a Novel Class of Dual Microsomal Prostaglandin E(2) Synthase-1/5-lipoxygenase Inhibitors Based on 2-[(4,6-Diphenethoxypyrimidin-2-yl)thio]hexanoic Acid J. Med. Chem. 2011, 54, 4490-4507
    • (2011) J. Med. Chem. , vol.54 , pp. 4490-4507
    • Hieke, M.1    Greiner, C.2    Dittrich, M.3    Reisen, F.4    Schneider, G.5    Schubert-Zsilavecz, M.6    Werz, O.7
  • 23
    • 78650176358 scopus 로고    scopus 로고
    • Arzanol, a prenylated heterodimeric phloroglucinyl pyrone, inhibits eicosanoid biosynthesis and exhibits anti-inflammatory efficacy in vivo
    • Bauer, J.; Koeberle, A.; Dehm, F.; Pollastro, F.; Appendino, G.; Northoff, H.; Rossi, A.; Sautebin, L.; Werz, O. Arzanol, a prenylated heterodimeric phloroglucinyl pyrone, inhibits eicosanoid biosynthesis and exhibits anti-inflammatory efficacy in vivo Biochem. Pharmacol. 2011, 81, 259-268
    • (2011) Biochem. Pharmacol. , vol.81 , pp. 259-268
    • Bauer, J.1    Koeberle, A.2    Dehm, F.3    Pollastro, F.4    Appendino, G.5    Northoff, H.6    Rossi, A.7    Sautebin, L.8    Werz, O.9
  • 24
    • 77249100287 scopus 로고    scopus 로고
    • Nonacidic inhibitors of human microsomal prostaglandin synthase 1 (mPGES 1) identified by a multistep virtual screening protocol
    • Rörsch, F.; Wobst, I.; Zettl, H.; Schubert-Zsilavecz, M.; Grosch, S.; Geisslinger, G.; Schneider, G.; Proschak, E. Nonacidic inhibitors of human microsomal prostaglandin synthase 1 (mPGES 1) identified by a multistep virtual screening protocol J. Med. Chem. 2010, 53, 911-915
    • (2010) J. Med. Chem. , vol.53 , pp. 911-915
    • Rörsch, F.1    Wobst, I.2    Zettl, H.3    Schubert-Zsilavecz, M.4    Grosch, S.5    Geisslinger, G.6    Schneider, G.7    Proschak, E.8
  • 26
    • 33745238704 scopus 로고    scopus 로고
    • Cyclooxygenase-2 (COX-2) - Independent anticarcinogenic effects of selective COX-2 inhibitors
    • DOI 10.1093/jnci/djj206
    • Grösch, S.; Maier, T. J.; Schiffmann, S.; Geisslinger, G. Cyclooxygenase-2 (COX-2)-independent anticarcinogenic effects of selective COX-2 inhibitors J. Natl. Cancer Inst. 2006, 98, 736-747 (Pubitemid 43983297)
    • (2006) Journal of the National Cancer Institute , vol.98 , Issue.11 , pp. 736-747
    • Grosch, S.1    Maier, T.J.2    Schiffmann, S.3    Geisslinger, G.4
  • 28
    • 62149139731 scopus 로고    scopus 로고
    • Setting up a 2D-LC/MS/MS method for the rapid quantitation of the prostanoid metabolites 6-oxo-PGF(1alpha) and TXB2 as markers for hemostasis assessment
    • Casetta, B.; Vecchione, G.; Tomaiuolo, M.; Margaglione, M.; Grandone, E. Setting up a 2D-LC/MS/MS method for the rapid quantitation of the prostanoid metabolites 6-oxo-PGF(1alpha) and TXB2 as markers for hemostasis assessment J. Mass. Spectrom. 2009, 44, 346-352
    • (2009) J. Mass. Spectrom. , vol.44 , pp. 346-352
    • Casetta, B.1    Vecchione, G.2    Tomaiuolo, M.3    Margaglione, M.4    Grandone, E.5
  • 30
    • 0023177955 scopus 로고
    • Leukotrienes and lipoxins: Structures, biosynthesis, and biological effects
    • Samuelsson, B.; Dahlen, S. E.; Lindgren, J. A.; Rouzer, C. A.; Serhan, C. N. Leukotrienes and lipoxins: structures, biosynthesis, and biological effects Science 1987, 237, 1171-1176 (Pubitemid 17131222)
    • (1987) Science , vol.237 , Issue.4819 , pp. 1171-1176
    • Samuelsson, B.1    Dahlen, S.-E.2    Lindgren, J.A.3
  • 31
    • 0022637743 scopus 로고
    • Arachidonic acid metabolism in bovine alveolar macrophages: Effect of calcium ionophore on lipoxygenase products
    • Taylor, S. M.; Liggitt, H. D.; Laegreid, W. W.; Silflow, R.; Leid, R. W. Arachidonic acid metabolism in bovine alveolar macrophages. Effect of calcium ionophore on lipoxygenase products Inflammation 1986, 10, 157-165 (Pubitemid 16117387)
    • (1986) Inflammation , vol.10 , Issue.2 , pp. 157-165
    • Taylor, S.M.1    Liggitt, H.D.2    Laegreid, W.W.3
  • 32
    • 33947369029 scopus 로고    scopus 로고
    • Zileuton: Clinical implications of 5-Lipoxygenase inhibition in severe airway disease
    • DOI 10.1111/j.1742-1241.2007.01320.x
    • Berger, W.; De Chandt, M. T.; Cairns, C. B. Zileuton: clinical implications of 5-lipoxygenase inhibition in severe airway disease Int. J. Clin. Pract. 2007, 61, 663-676 (Pubitemid 46449830)
    • (2007) International Journal of Clinical Practice , vol.61 , Issue.4 , pp. 663-676
    • Berger, W.1    De Chandt, M.T.M.2    Cairns, C.B.3
  • 35
    • 70349263442 scopus 로고    scopus 로고
    • The anti-inflammatory effects of prostaglandins
    • Scher, J. U.; Pillinger, M. H. The anti-inflammatory effects of prostaglandins J. Invest. Med. 2009, 57, 703-708
    • (2009) J. Invest. Med. , vol.57 , pp. 703-708
    • Scher, J.U.1    Pillinger, M.H.2
  • 38
    • 27744605174 scopus 로고    scopus 로고
    • Prostaglandin F2alpha produced by inducible cyclooxygenase may contribute to the resolution of inflammation
    • Colville-Nash, P. R.; Gilroy, D. W.; Willis, D.; Paul-Clark, M. J.; Moore, A. R.; Willoughby, D. A. Prostaglandin F2alpha produced by inducible cyclooxygenase may contribute to the resolution of inflammation Inflammopharmacology 2005, 12 (473-476) 477-480
    • (2005) Inflammopharmacology , vol.12 , Issue.473-476 , pp. 477-480
    • Colville-Nash, P.R.1    Gilroy, D.W.2    Willis, D.3    Paul-Clark, M.J.4    Moore, A.R.5    Willoughby, D.A.6
  • 39
    • 78649706279 scopus 로고    scopus 로고
    • The effect of plasma protein binding on in vivo efficacy: Misconceptions in drug discovery
    • Smith, D. A.; Di, L.; Kerns, E. H. The effect of plasma protein binding on in vivo efficacy: misconceptions in drug discovery Nature Rev. Drug Discovery 2010, 9, 929-939
    • (2010) Nature Rev. Drug Discovery , vol.9 , pp. 929-939
    • Smith, D.A.1    Di, L.2    Kerns, E.H.3
  • 41
    • 0037178121 scopus 로고    scopus 로고
    • A general and efficient copper catalyst for the amidation of aryl halides
    • DOI 10.1021/ja0260465
    • Klapars, A.; Huang, X.; Buchwald, S. L. A general and efficient copper catalyst for the amidation of aryl halides J. Am. Chem. Soc. 2002, 124, 7421-7428 (Pubitemid 34670450)
    • (2002) Journal of the American Chemical Society , vol.124 , Issue.25 , pp. 7421-7428
    • Klapars, A.1    Huang, X.2    Buchwald, S.L.3
  • 42
    • 0017184389 scopus 로고
    • A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding
    • Bradford, M. M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding Anal. Biochem. 1976, 72, 248-254
    • (1976) Anal. Biochem. , vol.72 , pp. 248-254
    • Bradford, M.M.1
  • 43
    • 0033755897 scopus 로고    scopus 로고
    • Coordinate up- and down-regulation of glutathione-dependent prostaglandin e synthase and cyclooxygenase-2 in A549 cells. Inhibition by NS-398 and leukotriene C4
    • Thoren, S.; Jakobsson, P. J. Coordinate up- and down-regulation of glutathione-dependent prostaglandin E synthase and cyclooxygenase-2 in A549 cells. Inhibition by NS-398 and leukotriene C4 Eur. J. Biochem. 2000, 267, 6428-6434
    • (2000) Eur. J. Biochem. , vol.267 , pp. 6428-6434
    • Thoren, S.1    Jakobsson, P.J.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.