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Volumn 46, Issue 9, 2003, Pages 1661-1669

Aromatic reduced amide bond peptidomimetics as selective inhibitors of neuronal nitric oxide synthase

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; DIPEPTIDE; GUANIDINE DERIVATIVE; N [4 AMINO 5 [2 (2 AMINOETHYL)PHENYLAMINO]PENTYL] N' NITROGUANIDINE; NITRIC OXIDE SYNTHASE INHIBITOR; UNCLASSIFIED DRUG;

EID: 0344088452     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0202932     Document Type: Article
Times cited : (47)

References (34)
  • 1
    • 0028125721 scopus 로고
    • Nitric oxide; a new paradigm for second messengers
    • Kerwin, J. F., Jr.; Lancaster, J. R. Jr. Nitric Oxide; A New Paradigm for Second Messengers. Med. Res. Rev. 1994, 14, 23-74.
    • (1994) Med. Res. Rev. , vol.14 , pp. 23-74
    • Kerwin J.F., Jr.1    Lancaster J.R., Jr.2
  • 2
    • 0026071876 scopus 로고
    • Calmodulin dependent endothelium-derived relaxing factor/nitric oxide synthase activity is present in the particulate and cytosolic fractions of bovine aortic endothelial cells
    • Forstermann, U.; Pollock, J. S.; Schmidt, H. H. H. W.; Heller, M.; Murad, F. Calmodulin Dependent Endothelium-Derived Relaxing Factor/Nitric Oxide Synthase Activity is Present in the Particulate and Cytosolic Fractions of Bovine Aortic Endothelial Cells. Prot. Natl. Acad. Sci. U.S.A. 1991, 88, 1788-1792.
    • (1991) Prot. Natl. Acad. Sci. U.S.A. , vol.88 , pp. 1788-1792
    • Forstermann, U.1    Pollock, J.S.2    Schmidt, H.H.H.W.3    Heller, M.4    Murad, F.5
  • 5
    • 0028064948 scopus 로고
    • Approaches toward selective inhibition of nitric oxide synthase
    • Marletta, M. A. Approaches Toward Selective Inhibition of Nitric Oxide Synthase. J. Med. Chem. 1994, 37, 1899-1907.
    • (1994) J. Med. Chem. , vol.37 , pp. 1899-1907
    • Marletta, M.A.1
  • 6
    • 0028863627 scopus 로고
    • Molecular mechanism and therapeutic strategies related to nitric oxide
    • Moncada, S.; Higgs, E. A. Molecular Mechanism 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
  • 8
    • 0030694038 scopus 로고    scopus 로고
    • Biosynthesis and action of nitric oxide in mammalian cells
    • (b) Mayer, B.; Hemmens, B. Biosynthesis and Action of Nitric Oxide in Mammalian Cells. Trends Biochem. Sci. 1997, 22, 477-481.
    • (1997) Trends Biochem. Sci. , vol.22 , pp. 477-481
    • Mayer, B.1    Hemmens, B.2
  • 10
    • 0029073807 scopus 로고
    • The role of peroxynitrite in nitric oxide-mediated toxicity
    • Crow, J. P.; Beckman, J. S. The Role of Peroxynitrite in Nitric Oxide-Mediated Toxicity. Curr. Top. Microbiol. Immunol. 1995, 196, 57-73.
    • (1995) Curr. Top. Microbiol. Immunol. , vol.196 , pp. 57-73
    • Crow, J.P.1    Beckman, J.S.2
  • 12
    • 0032133353 scopus 로고    scopus 로고
    • Design of isoform-selective inhibitors of nitric oxide synthase
    • Babu, B. R.; Griffith, O. W. Design of Isoform-Selective Inhibitors of nitric oxide synthase. Curr. Opin. Chem. Biol. 1998, 2, 491-500.
    • (1998) Curr. Opin. Chem. Biol. , vol.2 , pp. 491-500
    • Babu, B.R.1    Griffith, O.W.2
  • 13
    • 0030773013 scopus 로고    scopus 로고
    • Selective inhibition of neuronal nitric oxide synthase by Nω-nitroarginine- and phenylalanine-containing dipeptides and dipeptide esters
    • Silverman, R. B.; Huang, H.; Marletta, M. A.; Martesek, P. Selective Inhibition of Neuronal Nitric Oxide Synthase by Nω-Nitroarginine- and Phenylalanine-Containing Dipeptides and Dipeptide Esters. J. Med. Chem. 1997, 40, 2813-2817.
    • (1997) J. Med. Chem. , vol.40 , pp. 2813-2817
    • Silverman, R.B.1    Huang, H.2    Marletta, M.A.3    Martesek, P.4
  • 14
    • 0033549862 scopus 로고    scopus 로고
    • Nω- nitroarginine-containing dipeptide amides. Potent and highly selective inhibitors of neuronal nitric oxide synthase
    • Huang, H; Martasek, P.; Roman, L. J.; Masters, B. S. S.; Silverman, R. B. Nω- Nitroarginine-Containing Dipeptide Amides. Potent and Highly Selective Inhibitors of Neuronal Nitric Oxide Synthase. J. Med. Chem. 1999, 42, 3147-3153.
    • (1999) J. Med. Chem. , vol.42 , pp. 3147-3153
    • Huang, H.1    Martasek, P.2    Roman, L.J.3    Masters, B.S.S.4    Silverman, R.B.5
  • 15
    • 0027184034 scopus 로고
    • Selective inhibitor of constitutive nitric oxide synthase by NG-nitroarginine
    • Furfine, E. S.; Harmon, M. F.; Paith, J. E.; Garvey, E. P. Selective Inhibitor of Constitutive Nitric Oxide Synthase by NG-Nitroarginine. Biochemistry 1993, 32, 8512-8517.
    • (1993) Biochemistry , vol.32 , pp. 8512-8517
    • Furfine, E.S.1    Harmon, M.F.2    Paith, J.E.3    Garvey, E.P.4
  • 16
    • 0025737852 scopus 로고
    • Inhibition of the release of endothelium-derived relaxing factor in vitro and in vivo by dipeptides containing NG-nitro-L-arginine
    • Thiemermann, C.; Mustafa, M.; Mester, P. A.; Mitchell, J. A.; Hecker, M.; Vane, J. R. Inhibition of the release of endothelium-derived relaxing factor in vitro and in vivo by dipeptides containing NG-nitro-L-arginine. Br. J. Pharmacol. 1991, 104, 31-38.
    • (1991) Br. J. Pharmacol. , vol.104 , pp. 31-38
    • Thiemermann, C.1    Mustafa, M.2    Mester, P.A.3    Mitchell, J.A.4    Hecker, M.5    Vane, J.R.6
  • 17
    • 0026060469 scopus 로고
    • On the substrate specificity of nitric oxide synthase
    • Hecker, M.; Walsh, D. T.; Vane, J. R. On the substrate specificity of nitric oxide synthase. FEBS Lett. 1991, 294, 221-224.
    • (1991) FEBS Lett. , vol.294 , pp. 221-224
    • Hecker, M.1    Walsh, D.T.2    Vane, J.R.3
  • 20
    • 0034706017 scopus 로고    scopus 로고
    • ENDOR spectroscopic evidence for the geometry of binding of retro-inverso-Nω- nitroarginine-containing dipeptide amides to neuronal nitric oxide synthase
    • Tierney, D. L.; Huang, H.; Martasek, P.; Roman, L. J.; Silverman, R. B.; Hoffman, B. M. ENDOR Spectroscopic Evidence for the Geometry of Binding of retro-inverso-Nω- Nitroarginine-Containing Dipeptide Amides to Neuronal Nitric Oxide Synthase. J. Am. Chem. Soc. 2000, 122, 7869-7875.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 7869-7875
    • Tierney, D.L.1    Huang, H.2    Martasek, P.3    Roman, L.J.4    Silverman, R.B.5    Hoffman, B.M.6
  • 21
    • 0035797359 scopus 로고    scopus 로고
    • Reduced amide bond peptidomimetics. N- (4S)-[4-amino-5-(2-amino-alkylamino)-pentyl]-N′-nitroguanidines, potent and highly selective inhibitors of neuronal nitric oxide synthase
    • Hah, J.-M.; Roman, L. J.; Martasek, P.; Silverman, R. B. Reduced Amide Bond Peptidomimetics. N- (4S)-[4-Amino-5-(2-amino-alkylamino)-pentyl]-N′-nitroguanidines, Potent and Highly Selective Inhibitors of Neuronal Nitric Oxide Synthase. J. Med. Chem. 2001, 44, 2667-2670.
    • (2001) J. Med. Chem. , vol.44 , pp. 2667-2670
    • Hah, J.-M.1    Roman, L.J.2    Martasek, P.3    Silverman, R.B.4
  • 22
    • 0029972959 scopus 로고    scopus 로고
    • Novel and general method for the preparation of peptidyl argininals
    • Tamura, S. Y.; Semple, J. E.; Ardecky, R. J. Novel and General Method for the Preparation of Peptidyl Argininals. Tetrahedron Lett. 1996, 37, 4109-4112.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 4109-4112
    • Tamura, S.Y.1    Semple, J.E.2    Ardecky, R.J.3
  • 23
    • 0016835544 scopus 로고
    • A new method to synthesize α-aminoaldehydes
    • Ito, A.; Takahashi, R.; Baba, Y. A New Method to Synthesize α-Aminoaldehydes. Chem. Pharm. Bull. 1975, 23, 3081-3087.
    • (1975) Chem. Pharm. Bull. , vol.23 , pp. 3081-3087
    • Ito, A.1    Takahashi, R.2    Baba, Y.3
  • 24
    • 0030060780 scopus 로고    scopus 로고
    • Synthesis and characterization of photolabile chlorine precursors as reversible inhibitors of cholinesterases: Release of choline in the microsecond time range
    • Peng, L.; Goeldner, M. Synthesis and Characterization of Photolabile Chlorine Precursors as Reversible Inhibitors of Cholinesterases: Release of Choline in the Microsecond Time Range. J. Org. Chem. 1996, 61, 185-191.
    • (1996) J. Org. Chem. , vol.61 , pp. 185-191
    • Peng, L.1    Goeldner, M.2
  • 25
    • 0021364661 scopus 로고
    • Selective reduction of aromatic nitro compounds with stannous chloride in non acidic and non aqueous medium
    • Bellamy, F. D.; Ou, K. Selective Reduction of Aromatic Nitro Compounds with Stannous Chloride in Non Acidic and Non Aqueous Medium. Tetrahedron Lett. 1984, 25, 839-842.
    • (1984) Tetrahedron Lett. , vol.25 , pp. 839-842
    • Bellamy, F.D.1    Ou, K.2
  • 26
    • 53349112702 scopus 로고
    • N-tert-butoxycarbonyl-α,ω-alkanediamines from α,ω-alkanediamines
    • Krapcho, A. P.; Kuell, C. S. N-tert-Butoxycarbonyl-α,ω-Alkanediamines from α,ω-Alkanediamines. Synth. Commun. 1990, 20, 2559-2564.
    • (1990) Synth. Commun. , vol.20 , pp. 2559-2564
    • Krapcho, A.P.1    Kuell, C.S.2
  • 27
    • 77049143386 scopus 로고
    • Determination of enzyme-inhibitor constants
    • Dixon, M. Determination of enzyme-inhibitor constants. Biochem. J. 1953, 55, 170-171.
    • (1953) Biochem. J. , vol.55 , pp. 170-171
    • Dixon, M.1
  • 28
    • 0015972948 scopus 로고
    • Simple graphical method for determining the inhibition constants of mixed, uncompetitive, and noncompetitive inhibitors
    • Cornish-Bowden, A. Simple graphical method for determining the inhibition constants of mixed, uncompetitive, and noncompetitive inhibitors. Biochem. J. 1974, 137, 143-144.
    • (1974) Biochem. J. , vol.137 , pp. 143-144
    • Cornish-Bowden, A.1
  • 29
    • 0026323665 scopus 로고
    • Purification of the inducible murine macrophage nitric oxide synthase
    • Hevel, J. M.; White, K. A.; Marletta, M. Purification of the Inducible Murine Macrophage Nitric Oxide Synthase. J. Biol. Chem. 1991, 266, 22789-22791.
    • (1991) J. Biol. Chem. , vol.266 , pp. 22789-22791
    • Hevel, J.M.1    White, K.A.2    Marletta, M.3
  • 31
    • 0029048347 scopus 로고
    • Neuronal nitric oxide synthase. Expression in Escherichia coli, irreversible inhibition by phenyldiazene, and active site topology
    • Gerber, N. C.; Montelloano, P. R. Neuronal nitric oxide synthase. Expression in Escherichia coli, irreversible inhibition by phenyldiazene, and active site topology. J. Biol. Chem. 1995, 270, 17991-17996.
    • (1995) J. Biol. Chem. , vol.270 , pp. 17991-17996
    • Gerber, N.C.1    Montelloano, P.R.2
  • 33
    • 0028245391 scopus 로고
    • Nitric oxide synthase assays
    • Hevel, J. M.; Marletta, M. Nitric Oxide Synthase Assays. Methods Enzymol. 1994, 133, 250-258.
    • (1994) Methods Enzymol. , vol.133 , pp. 250-258
    • Hevel, J.M.1    Marletta, M.2
  • 34
    • 0003518480 scopus 로고
    • John Wiley and Sons: New York
    • Segel, I. H. Enzyme Kinetics; John Wiley and Sons: New York, 1975; p 105.
    • (1975) Enzyme Kinetics , pp. 105
    • Segel, I.H.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.