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Volumn 52, Issue 8, 2009, Pages 2443-2453

Design and synthesis of 2-amino-4-methylpyridine analogues as inhibitors for inducible nitric oxide synthase and in vivo evaluation of [ 18f]6-(2-fluoropropyl)-4-methyl-pyridin-2-amine as a potential PET tracer for inducible nitric oxide synthase

Author keywords

[No Author keywords available]

Indexed keywords

6 (2 FLUOROPROPYL) 4 METHYLPYRIDIN 2 AMINE F 18; 6 (3 FLUOROPROPYL) 4 METHYLPYRIDIN 2 AMINE; 6 (4 FLUOROBUTYL) 4 METHYLPYRIDIN 2 AMINE; ACTIN; AMINE; ENDOTHELIAL NITRIC OXIDE SYNTHASE; INDUCIBLE NITRIC OXIDE SYNTHASE; LIPOPOLYSACCHARIDE; NEURONAL NITRIC OXIDE SYNTHASE; NITRIC OXIDE SYNTHASE INHIBITOR; PICOLINE DERIVATIVE; TRACER; UNCLASSIFIED DRUG;

EID: 65249117571     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm801556h     Document Type: Article
Times cited : (43)

References (45)
  • 1
    • 22944434894 scopus 로고    scopus 로고
    • Modulation of prostaglandin biosynthesis by nitric oxide and nitric oxide donors
    • For the latest reviews, see: a
    • For the latest reviews, see: (a) Mollace, V.; Muscoli, C.; Masini, E.; Cuzzocrea, S.; Salvemini, D. Modulation of prostaglandin biosynthesis by nitric oxide and nitric oxide donors. Pharmacol. Rev. 2005, 57 , 217-252.
    • (2005) Pharmacol. Rev , vol.57 , pp. 217-252
    • Mollace, V.1    Muscoli, C.2    Masini, E.3    Cuzzocrea, S.4    Salvemini, D.5
  • 2
    • 0035425503 scopus 로고    scopus 로고
    • Nitric oxide synthases: Structure, function and inhibition
    • (b) Alderton, W. K.; Cooper, C. E.; Knowles, R. G. Nitric oxide synthases: structure, function and inhibition. Biochem. J. 2001, 357 , 593-615.
    • (2001) Biochem. J , vol.357 , pp. 593-615
    • Alderton, W.K.1    Cooper, C.E.2    Knowles, R.G.3
  • 3
    • 0032930417 scopus 로고    scopus 로고
    • Mammalian nitric oxide synthases
    • (a) Stuehr, D. J. Mammalian nitric oxide synthases. Biochim. Biophys. Acta 1999, 1411 , 217-230.
    • (1999) Biochim. Biophys. Acta , vol.1411 , pp. 217-230
    • Stuehr, D.J.1
  • 4
    • 0027325255 scopus 로고
    • Nitric oxide synthase structure and mechanism
    • (b) Marietta, M. A. Nitric oxide synthase structure and mechanism. J. Biol. Chem. 1993, 268 , 12231-12234.
    • (1993) J. Biol. Chem , vol.268 , pp. 12231-12234
    • Marietta, M.A.1
  • 6
    • 0035425503 scopus 로고    scopus 로고
    • Nitric oxide synthases: Structure, function and inhibition
    • (b) Alderton, W. K.; Cooper, C. E.; Knowles, R. G. Nitric oxide synthases: structure, function and inhibition. Biochem. J. 2001, 357 , 593-615.
    • (2001) Biochem. J , vol.357 , pp. 593-615
    • Alderton, W.K.1    Cooper, C.E.2    Knowles, R.G.3
  • 7
    • 0026629902 scopus 로고
    • Nitric oxide as a secretory product of mammalian cells
    • Nathan, C. Nitric oxide as a secretory product of mammalian cells. FASEB J. 1992, 6 , 3051-3064.
    • (1992) FASEB J , vol.6 , pp. 3051-3064
    • Nathan, C.1
  • 8
    • 0032928083 scopus 로고    scopus 로고
    • Nitric oxide in septic shock
    • (a) Titheradge, M. A. Nitric oxide in septic shock. Biochim. Biophys. Acta 1999, 1411 , 437-455.
    • (1999) Biochim. Biophys. Acta , vol.1411 , pp. 437-455
    • Titheradge, M.A.1
  • 9
    • 0032948112 scopus 로고    scopus 로고
    • Inhibition of nitric oxide synthase as a potential therapeutic target
    • (b) Hobbs, A. J.; Higgs, A.; Moncada, S. Inhibition of nitric oxide synthase as a potential therapeutic target. Annu. Rev. Pharmacol. Toxicol. 1999, 39 , 191-220.
    • (1999) Annu. Rev. Pharmacol. Toxicol , vol.39 , pp. 191-220
    • Hobbs, A.J.1    Higgs, A.2    Moncada, S.3
  • 10
    • 0036883907 scopus 로고    scopus 로고
    • Blocking NO synthesis: How, where and why?
    • (c) Vallance, P.; Leiper, J. Blocking NO synthesis: how, where and why? Nat. Rev. Drug Discovery 2002, 1 , 939-950.
    • (2002) Nat. Rev. Drug Discovery , vol.1 , pp. 939-950
    • Vallance, P.1    Leiper, J.2
  • 12
    • 0342723791 scopus 로고    scopus 로고
    • Nitric oxide in the pathogenesis of vascular disease
    • (e) Li, H.; Förstermann, U. Nitric oxide in the pathogenesis of vascular disease. J. Pathol. 2000, 190, 244-254.
    • (2000) J. Pathol , vol.190 , pp. 244-254
    • Li, H.1    Förstermann, U.2
  • 14
    • 23044511645 scopus 로고    scopus 로고
    • Inducible nitric oxide synthase (iNOS) in tumor biology: The two sides of the same coin
    • Lechner, M.; Lirk, P.; Rieder, J. Inducible nitric oxide synthase (iNOS) in tumor biology: the two sides of the same coin. Semin. Cancer Biol. 2005, 15 , 277-289.
    • (2005) Semin. Cancer Biol , vol.15 , pp. 277-289
    • Lechner, M.1    Lirk, P.2    Rieder, J.3
  • 15
    • 0029078058 scopus 로고
    • S -Alkvl-L-thiocitrullines. Potent stereoselective inhibitors of nitric oxide svnthase with strong pressor activity in vivo
    • (a) Narayanan, K.; Spack, L.; McMillan, K.; Kilbourn, R. G.; Hayward, M. A.; Masters, B. S.; Griffith, O. W. S -Alkvl-L-thiocitrullines. Potent stereoselective inhibitors of nitric oxide svnthase with strong pressor activity in vivo. J. Biol. Chem. 1995, 270 , 11103-11110.
    • (1995) J. Biol. Chem , vol.270 , pp. 11103-11110
    • Narayanan, K.1    Spack, L.2    McMillan, K.3    Kilbourn, R.G.4    Hayward, M.A.5    Masters, B.S.6    Griffith, O.W.7
  • 16
    • 0028173010 scopus 로고
    • N6 - (Iminoethyl) lysine:a selective inhibitor of inducible nitric oxide synthase
    • (b) Moore, W. M.; Webber, R. K.; Jerome, G. M.; Tjoeng, F. S.; Misko, T. P.; Currie, M. G. L-N6 - (Iminoethyl) lysine:a selective inhibitor of inducible nitric oxide synthase. J. Med. Chem. 1994, 37 , 3886-3888.
    • (1994) J. Med. Chem , vol.37 , pp. 3886-3888
    • Moore, W.M.1    Webber, R.K.2    Jerome, G.M.3    Tjoeng, F.S.4    Misko, T.P.5    Currie, M.G.L.6
  • 18
    • 0025804605 scopus 로고
    • Identification of N -iminoethyl-L-ornithine as an irreversible inhibitor of nitric oxide synthase in phagocytic cells
    • (d) McCall, T. B.; Feelisch, M.; Palmer, R. M.; Moncada, S. Identification of N -iminoethyl-L-ornithine as an irreversible inhibitor of nitric oxide synthase in phagocytic cells. Br. J. Pharmacol. 1991, 102 , 234-238.
    • (1991) Br. J. Pharmacol , vol.102 , pp. 234-238
    • McCall, T.B.1    Feelisch, M.2    Palmer, R.M.3    Moncada, S.4
  • 19
    • 0027967765 scopus 로고
    • Potent and selective inhibition of human nitric oxide synthases. Selective inhibition of neuronal nitric oxide synthase by S -methyl-L-thiocitruHine and S -ethyl- L-thiocitrulline
    • (e) Furfine, E. S.; Harmon, M. F.; Paith, J. E.; Knowles, R. G.; Salter, M.; Kiff, R. J.; Duffy, C.; Hazelwood, R.; Oplinger, J. A.; Garvey, E. P. Potent and selective inhibition of human nitric oxide synthases. Selective inhibition of neuronal nitric oxide synthase by S -methyl-L-thiocitruHine and S -ethyl- L-thiocitrulline. J. Biol. Chem. 1994, 269 , 26677-26683.
    • (1994) J. Biol. Chem , vol.269 , pp. 26677-26683
    • Furfine, E.S.1    Harmon, M.F.2    Paith, J.E.3    Knowles, R.G.4    Salter, M.5    Kiff, R.J.6    Duffy, C.7    Hazelwood, R.8    Oplinger, J.A.9    Garvey, E.P.10
  • 20
    • 0029078058 scopus 로고
    • S -Alkvl-L-thiocitrullines. Potent stereoselective inhibitors of nitric oxide synthase with strong pressor activity in vivo
    • (f) Narayanan, K.; Spack, L.; McMillan, K.; Kilbourn, R. G.; Hayward, M. A.; Masters, B. S.; Griffith, O. W. S -Alkvl-L-thiocitrullines. Potent stereoselective inhibitors of nitric oxide synthase with strong pressor activity in vivo. J. Biol. Chem. 1995, 270 , 11103-11110.
    • (1995) J. Biol. Chem , vol.270 , pp. 11103-11110
    • Narayanan, K.1    Spack, L.2    McMillan, K.3    Kilbourn, R.G.4    Hayward, M.A.5    Masters, B.S.6    Griffith, O.W.7
  • 21
    • 0028848015 scopus 로고
    • Isothioureas: Potent inhibitors of nitric oxide synthases with variable isoform selectivity
    • (g) Southan, G. J.; Szabo, C.; Thiemermann, C. Isothioureas: potent inhibitors of nitric oxide synthases with variable isoform selectivity. Br. J. Pharmacol. 1995, 114 , 510-516.
    • (1995) Br. J. Pharmacol , vol.114 , pp. 510-516
    • Southan, G.J.1    Szabo, C.2    Thiemermann, C.3
  • 22
    • 0034689418 scopus 로고    scopus 로고
    • Young, R. J.; Beams, R. M.; Carter, K.; Clark, H. A.; Coe, D. M.; Chambers, C. L.; Davies, P. I.; Dawson, J.; Drysdale, M. J.; Franzman, K. W.; French, C.; Hodgson, S. T.; Hodson, H. F.; Kleanthous, S.; Rider, P.; Sanders, D.; Sawyer, D. A.; Scott, K. J.; Shearer, B. G.; Stacker, R.; Smith, S.; Tackley, M. C.; Knowles, R. G. Inhibition of inducible nitric oxide synthase by acetamidine derivatives of heterosubstituted lysine and homolysine. Bioogs. Med. Chem. Lett. 2000, 10, 597-600.
    • (a) Young, R. J.; Beams, R. M.; Carter, K.; Clark, H. A.; Coe, D. M.; Chambers, C. L.; Davies, P. I.; Dawson, J.; Drysdale, M. J.; Franzman, K. W.; French, C.; Hodgson, S. T.; Hodson, H. F.; Kleanthous, S.; Rider, P.; Sanders, D.; Sawyer, D. A.; Scott, K. J.; Shearer, B. G.; Stacker, R.; Smith, S.; Tackley, M. C.; Knowles, R. G. Inhibition of inducible nitric oxide synthase by acetamidine derivatives of heterosubstituted lysine and homolysine. Bioogs. Med. Chem. Lett. 2000, 10, 597-600.
  • 23
    • 0031040613 scopus 로고    scopus 로고
    • 1400W is a slow, tight binding, and highly selective inhibitor of inducible nitric oxide synthase in vitro and in vivo
    • (b) Garvey, E. P.; Oplinger, J. A.; Furfine, E. S.; Kiff, R. J.; Laszlo, F.; Whittle, B. J.; Knowles, R. G. 1400W is a slow, tight binding, and highly selective inhibitor of inducible nitric oxide synthase in vitro and in vivo. J. Biol. Chem. 1997, 272 , 4959-4963.
    • (1997) J. Biol. Chem , vol.272 , pp. 4959-4963
    • Garvey, E.P.1    Oplinger, J.A.2    Furfine, E.S.3    Kiff, R.J.4    Laszlo, F.5    Whittle, B.J.6    Knowles, R.G.7
  • 24
    • 30044444530 scopus 로고    scopus 로고
    • The novel imidazopyridine 2-[2- (4-methoxy-pyridin-2-yl) -ethyrj-3H -imidazo[4, 5-b ]pyridine (BYK191023) is a highly selective inhibitor of the inducible nitric oxide synthase
    • (c) Strub, A.; Ulrich, W. R.; Hesslinger, C.; Eltze, M.; Fuchss, T.; Strassner, J.; Strand, S.; Lehner, M. D.; Boer, R. The novel imidazopyridine 2-[2- (4-methoxy-pyridin-2-yl) -ethyrj-3H -imidazo[4, 5-b ]pyridine (BYK191023) is a highly selective inhibitor of the inducible nitric oxide synthase. Mol. Pharmacol. 2006, 69 , 328-337.
    • (2006) Mol. Pharmacol , vol.69 , pp. 328-337
    • Strub, A.1    Ulrich, W.R.2    Hesslinger, C.3    Eltze, M.4    Fuchss, T.5    Strassner, J.6    Strand, S.7    Lehner, M.D.8    Boer, R.9
  • 25
    • 0035938426 scopus 로고    scopus 로고
    • 3, 4- Dihydro-1-isoquinolinamines: A novel class of nitric oxide synthase inhibitors with a range of isoform selectivity and potency
    • (d) Beaton, H.; Hamley, P.; Nicholls, D. J.; Tinker, A. C.; Wallace, A. V. 3, 4- Dihydro-1-isoquinolinamines: a novel class of nitric oxide synthase inhibitors with a range of isoform selectivity and potency. Bioorg. Med. Chem. Lett. 2001, 11 , 1023-1026.
    • (2001) Bioorg. Med. Chem. Lett , vol.11 , pp. 1023-1026
    • Beaton, H.1    Hamley, P.2    Nicholls, D.J.3    Tinker, A.C.4    Wallace, A.V.5
  • 28
    • 0030798573 scopus 로고    scopus 로고
    • Analgesic activity of 2-amino-4-methylpyridine, a novel NO synthase inhibitor
    • (b) Pettipher, E. R.; Hibbs, T. A.; Smith, M. A.; Griffiths, R. J. Analgesic activity of 2-amino-4-methylpyridine, a novel NO synthase inhibitor. Inflamm. Res. 1997, 46 , S135-S136.
    • (1997) Inflamm. Res , vol.46
    • Pettipher, E.R.1    Hibbs, T.A.2    Smith, M.A.3    Griffiths, R.J.4
  • 31
    • 0030447489 scopus 로고    scopus 로고
    • 183pF]fluoroethyl) isothiourea, as potential positron emission tomography tracers. J. Med. Chem. 1996, 39 , 5110-5118.
    • 183pF]fluoroethyl) isothiourea, as potential positron emission tomography tracers. J. Med. Chem. 1996, 39 , 5110-5118.
  • 32
    • 65249104387 scopus 로고    scopus 로고
    • 18F]FFDI), a potential PET radiotracer for the inducible nitric oxide synthase
    • 18F]FFDI), a potential PET radiotracer for the inducible nitric oxide synthase. Curr. Radiopharm. 2008, 1, 49-53.
    • (2008) Curr. Radiopharm , vol.1 , pp. 49-53
    • Tian, H.1    Lee, Z.2
  • 33
    • 3042530042 scopus 로고    scopus 로고
    • Synthesis and evaluation of a fluorine-18 labeled antisense oligonucleotide as a potential PET tracer for iNOS mRNA expression
    • (c) de Vries, E. F.; Vroegh, J.; Dijkstra, G.; Moshage, H.; Elsinga, P. H.; Jansen, P. L.; Vaalburg, W. Synthesis and evaluation of a fluorine-18 labeled antisense oligonucleotide as a potential PET tracer for iNOS mRNA expression. Nucl. Med. Biol. 2004, 31 , 605-612.
    • (2004) Nucl. Med. Biol , vol.31 , pp. 605-612
    • de Vries, E.F.1    Vroegh, J.2    Dijkstra, G.3    Moshage, H.4    Elsinga, P.H.5    Jansen, P.L.6    Vaalburg, W.7
  • 34
    • 33947317747 scopus 로고
    • Carbonyl olefination reaction using silyl-substituted organomet al.lic compounds
    • Peterson, D. J. Carbonyl olefination reaction using silyl-substituted organomet al.lic compounds. J. Org. Chem. 1968, 33 , 780-784.
    • (1968) J. Org. Chem , vol.33 , pp. 780-784
    • Peterson, D.J.1
  • 35
    • 0032877782 scopus 로고    scopus 로고
    • Pharmacological modulation of nitric oxide synthesis by mechanism-based inactivators and related inhibitors
    • Bryk, R.; Wolff, D. J. Pharmacological modulation of nitric oxide synthesis by mechanism-based inactivators and related inhibitors. Pharmacol. Ther. 1999, 84 , 157-178.
    • (1999) Pharmacol. Ther , vol.84 , pp. 157-178
    • Bryk, R.1    Wolff, D.J.2
  • 36
    • 41149177030 scopus 로고    scopus 로고
    • BYK191023 (2-[2- (4-methoxy-pyridin-2-yl) -ethyl]-3h -imidazo[4, 5- b ]pyridine) is an NADPH- and time-dependent irreversible inhibitor of inducible nitric-oxide synthase
    • Tiso, M.; Strub, A.; Hesslinger, C.; Kenney, C. T.; Boer, R.; Stuehr, D. J. BYK191023 (2-[2- (4-methoxy-pyridin-2-yl) -ethyl]-3h -imidazo[4, 5- b ]pyridine) is an NADPH- and time-dependent irreversible inhibitor of inducible nitric-oxide synthase. Mol. Pharmacol. 2008, 73 , 1244- 1253.
    • (2008) Mol. Pharmacol , vol.73 , pp. 1244-1253
    • Tiso, M.1    Strub, A.2    Hesslinger, C.3    Kenney, C.T.4    Boer, R.5    Stuehr, D.J.6
  • 37
    • 0345707647 scopus 로고    scopus 로고
    • Speyer, C. L.; Neff, T. A.; Warner, R. L.; Guo, R. F.; Sarma, J. V.; Riedemann, N. C.; Murphy, M. E.; Murphy, H. S.; Ward, P. A. Regulatory effects of iNOS on acute lung inflammatory responses in mice. Am. J. Pathol. 2003, 163 , 2319-2328. (a) Liu, S. F.; Adcock, I. M.; Old, R. W.; Barnes, P. J.; Evans, T. W. Differential regulation of the constitutive and inducible nitric oxide synthase mRNA by lipopolysaccharide treatment in vivo in the rat. Crit. Care Med. 1996, 24 , 1219-1225.
    • Speyer, C. L.; Neff, T. A.; Warner, R. L.; Guo, R. F.; Sarma, J. V.; Riedemann, N. C.; Murphy, M. E.; Murphy, H. S.; Ward, P. A. Regulatory effects of iNOS on acute lung inflammatory responses in mice. Am. J. Pathol. 2003, 163 , 2319-2328. (a) Liu, S. F.; Adcock, I. M.; Old, R. W.; Barnes, P. J.; Evans, T. W. Differential regulation of the constitutive and inducible nitric oxide synthase mRNA by lipopolysaccharide treatment in vivo in the rat. Crit. Care Med. 1996, 24 , 1219-1225.
  • 38
    • 0028072244 scopus 로고
    • Immunochemical localization of inducible nitric oxide synthase in endotoxin-treated rats
    • (b) Buttery, L. D.; Evans, T. J.; Springall, D. R.; Carpenter, A.; Cohen, J.; Polak, J. M. Immunochemical localization of inducible nitric oxide synthase in endotoxin-treated rats. Lab Invest. 1994, 7 , 755-764.
    • (1994) Lab Invest , vol.7 , pp. 755-764
    • Buttery, L.D.1    Evans, T.J.2    Springall, D.R.3    Carpenter, A.4    Cohen, J.5    Polak, J.M.6
  • 39
    • 5144221249 scopus 로고    scopus 로고
    • Lung, spleen, and kidney are the major places for inducible nitric oxide synthase expression in endotoxic shock: Role of p38 mitogen-activated protein kinase in signal transduction of inducible nitric oxide synthase expression
    • (c) Kan, W.; Zhao, K. S.; Jiang, Y.; Yan, W.; Huang, Q.; Wang, J.; Qin, Q.; Huang, X.; Wang, S. Lung, spleen, and kidney are the major places for inducible nitric oxide synthase expression in endotoxic shock: role of p38 mitogen-activated protein kinase in signal transduction of inducible nitric oxide synthase expression. Shock 2004, 21 , 281-287.
    • (2004) Shock , vol.21 , pp. 281-287
    • Kan, W.1    Zhao, K.S.2    Jiang, Y.3    Yan, W.4    Huang, Q.5    Wang, J.6    Qin, Q.7    Huang, X.8    Wang, S.9
  • 40
    • 0028863627 scopus 로고
    • Molecular mechanisms and therapeutic strategies related to nitric oxide
    • Moncada, S.; Higgs, E. A. Molecular mechanisms and therapeutic strategies related to nitric oxide. FASEB J. 1995, 9 , 1319-1330.
    • (1995) FASEB J , vol.9 , pp. 1319-1330
    • Moncada, S.1    Higgs, E.A.2
  • 41
    • 0026612638 scopus 로고
    • Effects of NG-nitro-L-arginine and L-arginine on regional cerebral blood flow in the cat
    • (a) Kovách, A. G.; Szabó, C.; Benyó, Z.; Csáki, C.; Greenberg, J. H.; Reivich, M. Effects of NG-nitro-L-arginine and L-arginine on regional cerebral blood flow in the cat. J. Physiol. 1992, 449 , 183-196.
    • (1992) J. Physiol , vol.449 , pp. 183-196
    • Kovách, A.G.1    Szabó, C.2    Benyó, Z.3    Csáki, C.4    Greenberg, J.H.5    Reivich, M.6
  • 42
    • 85047677246 scopus 로고
    • Importance of basal nitric oxide synthesis in regulation of myocardial blood flow
    • (b) Benyó, Z.; Kiss, G.; Szabó, C.; Csáki, C.; Kovách, A. G. Importance of basal nitric oxide synthesis in regulation of myocardial blood flow. Cardiouasc. Res. 1991, 25 , 700-703.
    • (1991) Cardiouasc. Res , vol.25 , pp. 700-703
    • Benyó, Z.1    Kiss, G.2    Szabó, C.3    Csáki, C.4    Kovách, A.G.5
  • 45
    • 0141776480 scopus 로고    scopus 로고
    • Newman, Melvin, S.; Waltcher, I.; Ginsberg, H. F. The synthesis and reduction of some polyfunctional acetylene compounds. J. Org. Chem. 1952, 17 , 962-970.
    • Newman, Melvin, S.; Waltcher, I.; Ginsberg, H. F. The synthesis and reduction of some polyfunctional acetylene compounds. J. Org. Chem. 1952, 17 , 962-970.


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