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Volumn 51, Issue 22, 2008, Pages 7057-7060

Discovery of boronic acids as novel and potent inhibitors of fatty acid amide hydrolase

Author keywords

[No Author keywords available]

Indexed keywords

ACYLGLYCEROL LIPASE; BENZENEBORONIC ACID; BORONIC ACID DERIVATIVE; FATTY ACID AMIDASE;

EID: 56749107455     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm801051t     Document Type: Article
Times cited : (57)

References (43)
  • 1
    • 0029904838 scopus 로고    scopus 로고
    • Molecular characterization of an enzyme that degrades neuromodulatory fatty-acid amides
    • Cravatt, B. F.; Giang, D. K.; Mayfield, S. P.; Boger, D. L.; Lerner, R. A.; Gilula, N. B. Molecular characterization of an enzyme that degrades neuromodulatory fatty-acid amides. Nature 1996, 384, 83-87.
    • (1996) Nature , vol.384 , pp. 83-87
    • Cravatt, B.F.1    Giang, D.K.2    Mayfield, S.P.3    Boger, D.L.4    Lerner, R.A.5    Gilula, N.B.6
  • 2
    • 0030903752 scopus 로고    scopus 로고
    • Molecular characterization of human and mouse fatty ccid amide hydrolases
    • Giang, D. K.; Cravatt, B. F. Molecular characterization of human and mouse fatty ccid amide hydrolases. Proc. Natl. Acad. Sci. U.S.A. 1997, 4, 2238-2242.
    • (1997) Proc. Natl. Acad. Sci. U.S.A , vol.4 , pp. 2238-2242
    • Giang, D.K.1    Cravatt, B.F.2
  • 5
    • 0028970517 scopus 로고    scopus 로고
    • Sugiura, T.; Kondo, S.; Sukawaga, A.; Nakane, S.; Shinoda, A; Itoh, K.; Yamasita, A.; Waku, K. 2-Arachidonoylglycerol: a possible endogenous cannabinoid receptor ligand in brain. Biochem. Biophys. Res. Commun. 1995, 215, 89-97.
    • Sugiura, T.; Kondo, S.; Sukawaga, A.; Nakane, S.; Shinoda, A; Itoh, K.; Yamasita, A.; Waku, K. 2-Arachidonoylglycerol: a possible endogenous cannabinoid receptor ligand in brain. Biochem. Biophys. Res. Commun. 1995, 215, 89-97.
  • 6
    • 0024263922 scopus 로고
    • Determination and characterization of a cannabinoid receptor in rat brain
    • Devane, W. A., 3rd; Johnson, M. R.; Melvin, L. S.; Howlett, A. C. Determination and characterization of a cannabinoid receptor in rat brain. Mol. Pharmacol. 1988, 34, 605-613.
    • (1988) Mol. Pharmacol , vol.34 , pp. 605-613
    • Devane 3rd, W.A.1    Johnson, M.R.2    Melvin, L.S.3    Howlett, A.C.4
  • 7
    • 0025325535 scopus 로고
    • Structure of cannabinoid receptor and functional expression of the cloned cDNA
    • Matsuda, L. A.; Lolait, S. J.; Brownstein, M. J.; Young, A. C.; Bonner, T. I. Structure of cannabinoid receptor and functional expression of the cloned cDNA. Nature 1990, 346, 561-564.
    • (1990) Nature , vol.346 , pp. 561-564
    • Matsuda, L.A.1    Lolait, S.J.2    Brownstein, M.J.3    Young, A.C.4    Bonner, T.I.5
  • 8
    • 0027515373 scopus 로고
    • Molecular characterization of a peripheral receptor for cannabinoids
    • Munro, S.; Thomas, K. L.; Abu-Shaar, M. Molecular characterization of a peripheral receptor for cannabinoids. Nature 1993, 365, 61-65.
    • (1993) Nature , vol.365 , pp. 61-65
    • Munro, S.1    Thomas, K.L.2    Abu-Shaar, M.3
  • 9
    • 0030870722 scopus 로고    scopus 로고
    • A second endogenous cannabinoid that modulates long-term potentiation
    • Stella, N.; Schweitzer, P.; Piomelli, D. A second endogenous cannabinoid that modulates long-term potentiation. Nature 1997, 388, 773-778.
    • (1997) Nature , vol.388 , pp. 773-778
    • Stella, N.1    Schweitzer, P.2    Piomelli, D.3
  • 10
    • 0033614020 scopus 로고    scopus 로고
    • Evidence that the cannabinoid CB1 receptor is a 2-arachidonoylglycerol receptor. Structure-activity relationship of 2-arachidonoylglycerol, ether-linked analogues, and related compounds
    • Sugiura, T.; Kodaka, T.; Nakane, S.; Miyahita, T.; Kondo, S.; Suhara, Y.; Takayama, H.; Waku, K.; Seki, C.; Baba, N.; Ishima, Y. Evidence that the cannabinoid CB1 receptor is a 2-arachidonoylglycerol receptor. Structure-activity relationship of 2-arachidonoylglycerol, ether-linked analogues, and related compounds. J. Biol. Chem. 1999, 274, 2794-2801.
    • (1999) J. Biol. Chem , vol.274 , pp. 2794-2801
    • Sugiura, T.1    Kodaka, T.2    Nakane, S.3    Miyahita, T.4    Kondo, S.5    Suhara, Y.6    Takayama, H.7    Waku, K.8    Seki, C.9    Baba, N.10    Ishima, Y.11
  • 11
    • 23444432920 scopus 로고    scopus 로고
    • The endocannabinoid system: Drag targets, lead compounds, and potential therapeutic applications
    • Lambert, D. M.; Fowler, C. J. The endocannabinoid system: drag targets, lead compounds, and potential therapeutic applications. J. Med. Chem. 2005, 48, 5059-5087.
    • (2005) J. Med. Chem , vol.48 , pp. 5059-5087
    • Lambert, D.M.1    Fowler, C.J.2
  • 13
    • 37149013708 scopus 로고    scopus 로고
    • A comprehensive profile of brain enzymes that hydrolyze the endocannabinoid 2-arachidonoylglycerol
    • Blankman, J. L.; Simon, G. M.; Cravatt, B. F. A comprehensive profile of brain enzymes that hydrolyze the endocannabinoid 2-arachidonoylglycerol. Chem. Biol. 2007, 14, 1309-1311.
    • (2007) Chem. Biol , vol.14 , pp. 1309-1311
    • Blankman, J.L.1    Simon, G.M.2    Cravatt, B.F.3
  • 17
    • 0042832959 scopus 로고    scopus 로고
    • Arachidonylsulfonyl derivatives as cannabinoid CB1 receptor and fatty Acid amide hydrolase inhibitors
    • Segall, Y.; Quistad, G. B.; Nomura, D. K.; Casida, J. E. Arachidonylsulfonyl derivatives as cannabinoid CB1 receptor and fatty Acid amide hydrolase inhibitors. Bioorg. Med. Chem. Lett. 2003, 13, 3301-3303.
    • (2003) Bioorg. Med. Chem. Lett , vol.13 , pp. 3301-3303
    • Segall, Y.1    Quistad, G.B.2    Nomura, D.K.3    Casida, J.E.4
  • 22
    • 4644354869 scopus 로고    scopus 로고
    • Reversible inhibitors of fatty acid amide hydrolase that promote analgesia: Evidence for an unprecented combination of potency and selectivity
    • Lichtman, A. H.; Leung, D.; Shelton, C.; Saghatelian, A.; Hardouin, C.; Boger, D. L.; Cravatt, B. F. Reversible inhibitors of fatty acid amide hydrolase that promote analgesia: evidence for an unprecented combination of potency and selectivity. J. Pharmacol. Exp. Ther. 2004, 311, 441-448.
    • (2004) J. Pharmacol. Exp. Ther , vol.311 , pp. 441-448
    • Lichtman, A.H.1    Leung, D.2    Shelton, C.3    Saghatelian, A.4    Hardouin, C.5    Boger, D.L.6    Cravatt, B.F.7
  • 23
    • 34548131105 scopus 로고    scopus 로고
    • Design, synthesis, and in vitro evaluation of carbamate derivatives of 2-benzoxazolyl- and 2-benzothiazolyl-(3-hydroxyphenyl)-methanones as novel fatty acid amide hydrolase inhibitors
    • Myllymäki, M. J.; Saario, S. M.; Kataja, A.; Castillo-Melendez, J. A.; Nevalainen, T.; Juvonen, R. O.; Järvinen, T.; Koskinen, A. M. P. Design, synthesis, and in vitro evaluation of carbamate derivatives of 2-benzoxazolyl- and 2-benzothiazolyl-(3-hydroxyphenyl)-methanones as novel fatty acid amide hydrolase inhibitors. J. Med. Chem. 2007, 50, 4236-4242.
    • (2007) J. Med. Chem , vol.50 , pp. 4236-4242
    • Myllymäki, M.J.1    Saario, S.M.2    Kataja, A.3    Castillo-Melendez, J.A.4    Nevalainen, T.5    Juvonen, R.O.6    Järvinen, T.7    Koskinen, A.M.P.8
  • 24
    • 56749169026 scopus 로고    scopus 로고
    • WO Patent 087569
    • Sit, S.-Y.; Xie, K. WO Patent 087569, 2002.
    • (2002)
    • Sit, S.-Y.1    Xie, K.2
  • 27
    • 27144431754 scopus 로고    scopus 로고
    • Inhibitors of fatty acid amide hydrolase reduce carrageenan-induced hind paw inflammation in pentobarbital-treated mice: Comparison with indomethacin and possible involvement of cannabinoid receptors
    • Holt, S.; Comelli, F.; Costa, B.; Fowler, C. J. Inhibitors of fatty acid amide hydrolase reduce carrageenan-induced hind paw inflammation in pentobarbital-treated mice: comparison with indomethacin and possible involvement of cannabinoid receptors. Br. J. Pharmacol. 2005, 146, 467-476.
    • (2005) Br. J. Pharmacol , vol.146 , pp. 467-476
    • Holt, S.1    Comelli, F.2    Costa, B.3    Fowler, C.J.4
  • 28
    • 34250750792 scopus 로고    scopus 로고
    • The fatty acid amide hydrolase inhibitor URB597 (cyclohexylcarbamic acid 3′-carbamoylbiphenyl-3-yl ester) reduces neuropathic pain after oral administration in mice
    • Russo, R.; Loverne, J.; La Rana, G.; Compton, T. R.; Parrot, J.; Duranti, A.; Tontini, A.; Mor, M.; Tarzia, G.; Calignano, A.; Piomelli, D. The fatty acid amide hydrolase inhibitor URB597 (cyclohexylcarbamic acid 3′-carbamoylbiphenyl-3-yl ester) reduces neuropathic pain after oral administration in mice. J. Pharmacol. Exp. Ther. 2007, 322, 236-242.
    • (2007) J. Pharmacol. Exp. Ther , vol.322 , pp. 236-242
    • Russo, R.1    Loverne, J.2    La Rana, G.3    Compton, T.R.4    Parrot, J.5    Duranti, A.6    Tontini, A.7    Mor, M.8    Tarzia, G.9    Calignano, A.10    Piomelli, D.11
  • 29
    • 33845799619 scopus 로고    scopus 로고
    • Analgesic effects of fatty acid amide hydrolase inhibition in a rat model of neuropathic pain
    • Jhaveri, M. D.; Richardson, D.; Kendall, D. A.; Barret, D. A.; Chapman, V. Analgesic effects of fatty acid amide hydrolase inhibition in a rat model of neuropathic pain. J. Neurosci. 2006, 26, 13318-13327.
    • (2006) J. Neurosci , vol.26 , pp. 13318-13327
    • Jhaveri, M.D.1    Richardson, D.2    Kendall, D.A.3    Barret, D.A.4    Chapman, V.5
  • 31
    • 1542346866 scopus 로고    scopus 로고
    • Monoglyceride lipase-like enzymatic activity is responsible for hydrolysis of 2-arachidonoylglycerol in rat cerebellar membranes
    • Saario, S. M.; Savinainen, J. R.; Laitinen, J. T.; Järvinen, T.; Niemi, R. Monoglyceride lipase-like enzymatic activity is responsible for hydrolysis of 2-arachidonoylglycerol in rat cerebellar membranes. Biochem. Pharmacol. 2004, 67, 1381-1387.
    • (2004) Biochem. Pharmacol , vol.67 , pp. 1381-1387
    • Saario, S.M.1    Savinainen, J.R.2    Laitinen, J.T.3    Järvinen, T.4    Niemi, R.5
  • 32
    • 0017295234 scopus 로고
    • Purification and some properties of a monoglycerol-hydrolyzing enzyme of rat adipose tissue
    • Tornqvist, H.; Belfrage, P. Purification and some properties of a monoglycerol-hydrolyzing enzyme of rat adipose tissue. J. Biol. Chem. 1976, 251, 813-819.
    • (1976) J. Biol. Chem , vol.251 , pp. 813-819
    • Tornqvist, H.1    Belfrage, P.2
  • 33
    • 24944508307 scopus 로고    scopus 로고
    • Characterization of the sulfhydryl-sensitive site in the enzyme responsible for hydrolysis of 2-arachidonoyl-glycerol in rat cerebellar membranes
    • Saario, S. M.; Salo, O. M. H.; Nevalainen, T.; Poso, A.; Laitinen, J. T.; Järvinen, T.; Niemi, R. Characterization of the sulfhydryl-sensitive site in the enzyme responsible for hydrolysis of 2-arachidonoyl-glycerol in rat cerebellar membranes. Chem. Biol. 2005, 12, 649-659.
    • (2005) Chem. Biol , vol.12 , pp. 649-659
    • Saario, S.M.1    Salo, O.M.H.2    Nevalainen, T.3    Poso, A.4    Laitinen, J.T.5    Järvinen, T.6    Niemi, R.7
  • 34
    • 0037405256 scopus 로고    scopus 로고
    • Boronic acid compounds as potential pharmaceutical agents
    • Yang, W.; Gao, X.; Wang, B. Boronic acid compounds as potential pharmaceutical agents. Med. Res. Rev. 2003, 23, 346-368.
    • (2003) Med. Res. Rev , vol.23 , pp. 346-368
    • Yang, W.1    Gao, X.2    Wang, B.3
  • 36
    • 0033607236 scopus 로고    scopus 로고
    • Fatty acid hydrolase competitively degrades bioactive amides and esters through a nonconventinal catalytic mechanism
    • Patricelli, M. P.; Cravatt, B. F. Fatty acid hydrolase competitively degrades bioactive amides and esters through a nonconventinal catalytic mechanism. Biochemistry 1999, 38, 14125-14130.
    • (1999) Biochemistry , vol.38 , pp. 14125-14130
    • Patricelli, M.P.1    Cravatt, B.F.2
  • 37
    • 0033520099 scopus 로고    scopus 로고
    • Chemical and mutagenic investigations of fatty acid amide hydrolase: Evidence for a family of serine hydrolases with distinct catalytic properties
    • Patricelli, M. P.; Lovato, M. A.; Cravatt, B. F. Chemical and mutagenic investigations of fatty acid amide hydrolase: evidence for a family of serine hydrolases with distinct catalytic properties. Biochemistry 1999, 38, 9804-9812.
    • (1999) Biochemistry , vol.38 , pp. 9804-9812
    • Patricelli, M.P.1    Lovato, M.A.2    Cravatt, B.F.3
  • 38
    • 2242490907 scopus 로고    scopus 로고
    • Structural adaptations in a membrane enzyme that terminates endocannabinoid signaling
    • Bracey, M. H.; Hanson, M. A.; Masuda, K. R.; Stevens, R. C.; Cravatt, B. F. Structural adaptations in a membrane enzyme that terminates endocannabinoid signaling. Science 2002, 298, 1793-1796.
    • (2002) Science , vol.298 , pp. 1793-1796
    • Bracey, M.H.1    Hanson, M.A.2    Masuda, K.R.3    Stevens, R.C.4    Cravatt, B.F.5
  • 39
    • 33746718652 scopus 로고    scopus 로고
    • Fatty acid amide inhibitors from virtual screening of the endocannabinoid system
    • Saario, S. M.; Poso, A.; Juvonen, R. O.; Järvinen, T.; SaIo, O. M. H. Fatty acid amide inhibitors from virtual screening of the endocannabinoid system. J. Med. Chem. 2006, 49, 4650-4656.
    • (2006) J. Med. Chem , vol.49 , pp. 4650-4656
    • Saario, S.M.1    Poso, A.2    Juvonen, R.O.3    Järvinen, T.4    SaIo, O.M.H.5
  • 40
    • 84889487088 scopus 로고
    • Structure, Properties, and Preparation of Boronic Acid Derivatives. Overview of Their Reactions and Applications
    • 1st ed, Hall, D. G, Eds, Wiley-VCH: Weinheim, Germany
    • Hall, D. G. Structure, Properties, and Preparation of Boronic Acid Derivatives. Overview of Their Reactions and Applications. In Boronic Acids, 1st ed.; Hall, D. G., Eds.; Wiley-VCH: Weinheim, Germany, 1995; pp 1-99.
    • (1995) Boronic Acids , pp. 1-99
    • Hall, D.G.1
  • 42
    • 33845923661 scopus 로고    scopus 로고
    • Elucidation of hydrolysis mechanisms for fatty acid amide hydrolase and its Lys142Ala variant via QM/MM simulations
    • Tubert-Brohman, I.; Acevedo, O.; Jorgensen, W. L. Elucidation of hydrolysis mechanisms for fatty acid amide hydrolase and its Lys142Ala variant via QM/MM simulations. J. Am. Chem. Soc. 2006, 128, 16904-16913.
    • (2006) J. Am. Chem. Soc , vol.128 , pp. 16904-16913
    • Tubert-Brohman, I.1    Acevedo, O.2    Jorgensen, W.L.3
  • 43
    • 37349122437 scopus 로고    scopus 로고
    • Identification of productive inhibitor binding orientation in fatty acid amide hydrolase (FAAH) by QM/MM mechanistic modelling
    • Lodola, A.; Mor, M.; Rivara, S.; Christov, C.; Tarzia, G.; Piomelli, D.; Mulholland, A. J. Identification of productive inhibitor binding orientation in fatty acid amide hydrolase (FAAH) by QM/MM mechanistic modelling. Chem. Commun. 2008, 2, 214-216.
    • (2008) Chem. Commun , vol.2 , pp. 214-216
    • Lodola, A.1    Mor, M.2    Rivara, S.3    Christov, C.4    Tarzia, G.5    Piomelli, D.6    Mulholland, A.J.7


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