메뉴 건너뛰기




Volumn 46, Issue 10, 2003, Pages 1989-1996

Synthesis and biological evaluation of thiol-based inhibitors of glutamate carboxypeptidase II: Discovery of an orally active GCP II inhibitor

Author keywords

[No Author keywords available]

Indexed keywords

2 (3 MERCAPTOPROPYL)PENTANEDIOIC ACID; 2 (HYDROXYPENTAFLUOROPHENYLMETHYLPHOSPHINOYLMETHYL)PENTANEDIOIC ACID; 2 (PHOSPHONOMETHYL)PENTANEDIOIC ACID; 5 MERCAPTOPENTANOIC ACID; CARBENE; ENZYME INHIBITOR; GAMMA GLUTAMYL HYDROLASE; GLUTAMATE CARBOXYPEPTIDASE II INHIBITOR; GLUTARIC ACID DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; PROPIONIC ACID; THIOL DERIVATIVE; UNCLASSIFIED DRUG; VALERIC ACID DERIVATIVE; ZINC;

EID: 0038748474     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm020515w     Document Type: Article
Times cited : (100)

References (33)
  • 1
    • 0033851295 scopus 로고    scopus 로고
    • L-glutamate as a central neurotransmitter: Looking back
    • Watkins, J. C. L-Glutamate as a central neurotransmitter: Looking back. Biochem. Soc. Trans. 2000, 28, 297-309.
    • (2000) Biochem. Soc. Trans. , vol.28 , pp. 297-309
    • Watkins, J.C.1
  • 5
    • 0034192772 scopus 로고    scopus 로고
    • NAALADase inhibitors: A novel approach to glutamate regulation
    • Whelan, J. NAALADase inhibitors: A novel approach to glutamate regulation. Drug Discovery Today 2000, 5, 171-172.
    • (2000) Drug Discovery Today , vol.5 , pp. 171-172
    • Whelan, J.1
  • 7
    • 0025291108 scopus 로고
    • Competitive inhibition of N-acetylated-alpha-linked acidic dipeptidase activity by N-acetyl-L-aspartyl-beta-linked L-glutamate
    • Serval, V.; Barbeito, L.; Pittaluga, A.; Cheramy, A.; Lavielle, S.; Glowinski, J. Competitive inhibition of N-acetylated-alpha-linked acidic dipeptidase activity by N-acetyl-L-aspartyl-beta-linked L-glutamate. J. Neurochem. 1990, 55, 39-46.
    • (1990) J. Neurochem. , vol.55 , pp. 39-46
    • Serval, V.1    Barbeito, L.2    Pittaluga, A.3    Cheramy, A.4    Lavielle, S.5    Glowinski, J.6
  • 8
    • 0025035762 scopus 로고
    • Synthesis of acyclic and dehydroaspartic acid analogues of Ac-Asp-Glu-OH and their inhibition of rat brain N-acetylated α-linked acidic dipeptidase (NAALA dipeptidase)
    • Subasinghe, N.; Schulte, M.; Chan, M. Y.; Roon, R. J.; Koerner, J. F.; Johnson, R. L. Synthesis of acyclic and dehydroaspartic acid analogues of Ac-Asp-Glu-OH and their inhibition of rat brain N-acetylated α-linked acidic dipeptidase (NAALA dipeptidase). J. Med. Chem. 1990, 33, 2734-2744.
    • (1990) J. Med. Chem. , vol.33 , pp. 2734-2744
    • Subasinghe, N.1    Schulte, M.2    Chan, M.Y.3    Roon, R.J.4    Koerner, J.F.5    Johnson, R.L.6
  • 9
    • 0034624744 scopus 로고    scopus 로고
    • Dual function glutamate-related ligands: Discovery of a novel, potent inhibitor of glutamate carboxypeptidase II possessing mGluR3 agonist activity
    • Nan, F.; Bzdega, T.; Pshenichkin, S.; Wroblewski, J. T.; Wroblewska, B.; Neale, J. H.; Kozikowski, A. P. Dual function glutamate-related ligands: discovery of a novel, potent inhibitor of glutamate carboxypeptidase II possessing mGluR3 agonist activity. J. Med. Chem. 2000, 43, 772-774.
    • (2000) J. Med. Chem. , vol.43 , pp. 772-774
    • Nan, F.1    Bzdega, T.2    Pshenichkin, S.3    Wroblewski, J.T.4    Wroblewska, B.5    Neale, J.H.6    Kozikowski, A.P.7
  • 11
    • 0035695735 scopus 로고    scopus 로고
    • Inhibition of glutamate carboxypeptidase II by phosphonamidothionate derivatives of glutamic acid
    • Rodriguez, C. E.; Lu, H.; Martinez, A. R.; Hu, Y.; Brunelle, A.; Berkman, C. E. Inhibition of glutamate carboxypeptidase II by phosphonamidothionate derivatives of glutamic acid. J. Enzyme Inhib. 2001, 16, 359-365.
    • (2001) J. Enzyme Inhib. , vol.16 , pp. 359-365
    • Rodriguez, C.E.1    Lu, H.2    Martinez, A.R.3    Hu, Y.4    Brunelle, A.5    Berkman, C.E.6
  • 12
    • 0037135992 scopus 로고    scopus 로고
    • Phosphonate and phosphinate analogues of N-Acylated gamma-glutamylglutamate. Potent inhibitors of glutamate carboxypeptidase II
    • Tsukamoto, T.; Flanary, J. M.; Rojas, C.; Slusher, B. S.; Valiaeva, N.; Coward, J. K. Phosphonate and phosphinate analogues of N-Acylated gamma-glutamylglutamate. Potent inhibitors of glutamate carboxypeptidase II. Bioorg. Med. Chem. Lett. 2002, 12, 2189-2192.
    • (2002) Bioorg. Med. Chem. Lett. , vol.12 , pp. 2189-2192
    • Tsukamoto, T.1    Flanary, J.M.2    Rojas, C.3    Slusher, B.S.4    Valiaeva, N.5    Coward, J.K.6
  • 13
    • 0030053446 scopus 로고    scopus 로고
    • Design, synthesis, and biological activity of a potent inhibitor of the neuropeptidase N-acetylated α-linked acidic dipeptidase
    • Jackson, P. F.; Cole, D. C.; Slusher, B. S.; Stetz, S. L.; Ross, L. E.; Donzanti, B. A.; Trainor, D. A. Design, synthesis, and biological activity of a potent inhibitor of the neuropeptidase N-acetylated α-linked acidic dipeptidase. J. Med. Chem. 1996, 39, 619-622.
    • (1996) J. Med. Chem. , vol.39 , pp. 619-622
    • Jackson, P.F.1    Cole, D.C.2    Slusher, B.S.3    Stetz, S.L.4    Ross, L.E.5    Donzanti, B.A.6    Trainor, D.A.7
  • 14
    • 0036853992 scopus 로고    scopus 로고
    • Kinetics and inhibition ofglutamate carboxypeptidase II using a microplate assay
    • Rojas, C.; Frazier, S. T.; Flanary, J.; Slusher, B. S. Kinetics and inhibition ofglutamate carboxypeptidase II using a microplate assay. Anal. Biochem. 2002, 310, 50-54.
    • (2002) Anal. Biochem. , vol.310 , pp. 50-54
    • Rojas, C.1    Frazier, S.T.2    Flanary, J.3    Slusher, B.S.4
  • 17
    • 0343844454 scopus 로고    scopus 로고
    • Prodrugs of phosphates, phosphonates, and phosphinates
    • Krise, J. P.; Stella, V. J. Prodrugs of phosphates, phosphonates, and phosphinates. Adv. Drug Delivery Rev. 1996, 19, 287-310.
    • (1996) Adv. Drug Delivery Rev. , vol.19 , pp. 287-310
    • Krise, J.P.1    Stella, V.J.2
  • 18
    • 0032828165 scopus 로고    scopus 로고
    • Design of angiotensin converting enzyme inhibitors
    • Cushman, D. W.; Ondetti, M. A. Design of angiotensin converting enzyme inhibitors. Nat. Med. 1999, 5, 1110-1113.
    • (1999) Nat. Med. , vol.5 , pp. 1110-1113
    • Cushman, D.W.1    Ondetti, M.A.2
  • 19
    • 0033017628 scopus 로고    scopus 로고
    • Preparation of carboxythioalactones and their active derivatives
    • Garbiras, B. J.; Stephen, M. Preparation of Carboxythioalactones and Their Active Derivatives. Synthesis 1999, 270-274.
    • (1999) Synthesis , pp. 270-274
    • Garbiras, B.J.1    Stephen, M.2
  • 20
    • 0038521833 scopus 로고    scopus 로고
    • 2-Mercaptomethylglutaric acid derivatives. U.S. Patent 4, 927, 966
    • Kalman, T. I. 2-Mercaptomethylglutaric acid derivatives. U.S. Patent 4, 927, 966.
    • Kalman, T.I.1
  • 21
    • 0037131338 scopus 로고    scopus 로고
    • Facile synthesis of α-substituted acrylate esters
    • Hin, B.; Majer, P.; Tsukamoto, T. Facile Synthesis of α-Substituted Acrylate Esters. J. Org. Chem. 2002, 67, 7365-7368.
    • (2002) J. Org. Chem. , vol.67 , pp. 7365-7368
    • Hin, B.1    Majer, P.2    Tsukamoto, T.3
  • 22
    • 0025358901 scopus 로고
    • Inhibition of γ-butyrobetaine hydroxylase by cyclopropyl-substituted γ-butyrobetaines
    • Petter, R. C.; Banerjee, S.; Englard, S. Inhibition of γ-Butyrobetaine Hydroxylase by Cyclopropyl-Substituted γ-Butyrobetaines. J. Org. Chem. 1990, 55, 3088-3097.
    • (1990) J. Org. Chem. , vol.55 , pp. 3088-3097
    • Petter, R.C.1    Banerjee, S.2    Englard, S.3
  • 23
    • 0024832316 scopus 로고
    • A short large scale synthesis of (±) sarkomycin esters
    • Amri, H.; Rambaud, M.; Villieras, J. A short large scale synthesis of (±) sarkomycin esters. Tetrahedron Lett. 1989, 30, 7381-7382.
    • (1989) Tetrahedron Lett. , vol.30 , pp. 7381-7382
    • Amri, H.1    Rambaud, M.2    Villieras, J.3
  • 24
    • 0017584729 scopus 로고
    • Design of potent competitive inhibitors of angiotensin-converting enzyme. Carboxyalkanoyl and mercaptoalkanoyl amino acids
    • Cushman, D. W.; Cheung, H. S.; Sabo, E. F.; Ondetti, M. A. Design of potent competitive inhibitors of angiotensin-converting enzyme. Carboxyalkanoyl and mercaptoalkanoyl amino acids. Biochemistry 1977, 16, 5484-5491.
    • (1977) Biochemistry , vol.16 , pp. 5484-5491
    • Cushman, D.W.1    Cheung, H.S.2    Sabo, E.F.3    Ondetti, M.A.4
  • 26
    • 0030940306 scopus 로고    scopus 로고
    • Structure of membrane glutamate carboxypeptidase
    • Rawlings, N. D.; Barrett, A. J. Structure of membrane glutamate carboxypeptidase. Biochim. Biophys. Acta 1997, 1339, 247-252.
    • (1997) Biochim. Biophys. Acta , vol.1339 , pp. 247-252
    • Rawlings, N.D.1    Barrett, A.J.2
  • 27
    • 0034934693 scopus 로고    scopus 로고
    • Design of NAALADase inhibitors: A novel neuroprotective strategy
    • Jackson, P. F.; Slusher, B. S. Design of NAALADase inhibitors: A novel neuroprotective strategy. Curr. Med. Chem. 2001, 8, 949-957.
    • (2001) Curr. Med. Chem. , vol.8 , pp. 949-957
    • Jackson, P.F.1    Slusher, B.S.2
  • 29
    • 0037068438 scopus 로고    scopus 로고
    • Molecular modeling of the interactions of glutamate carboxypeptidase II with its potent NAAG-based inhibitors
    • Rong, S. B.; Zhang, J.; Neale, J. H.; Wroblewski, J. T.; Wang, S.; Kozikowski, A. P. Molecular modeling of the interactions of glutamate carboxypeptidase II with its potent NAAG-based inhibitors. J. Med. Chem. 2002, 45, 4140-4152.
    • (2002) J. Med. Chem. , vol.45 , pp. 4140-4152
    • Rong, S.B.1    Zhang, J.2    Neale, J.H.3    Wroblewski, J.T.4    Wang, S.5    Kozikowski, A.P.6
  • 31
    • 0023895875 scopus 로고
    • A peripheral mononeuropathy in rat that produces disorders of pain sensation like those seen in man
    • Bennett, G. J.; Xie, Y. K. A peripheral mononeuropathy in rat that produces disorders of pain sensation like those seen in man. Pain 1988, 33, 87-107.
    • (1988) Pain , vol.33 , pp. 87-107
    • Bennett, G.J.1    Xie, Y.K.2
  • 32
    • 0036488137 scopus 로고    scopus 로고
    • Substrate specificity, inhibition and enzymological analysis of recombinant human glutamate carboxypeptidase II
    • Barinka, C.; Rinnova, M.; Sacha, P.; Rojas, C.; Majer, P.; Slusher, B. S.; Konvalinka, J. Substrate specificity, inhibition and enzymological analysis of recombinant human glutamate carboxypeptidase II. J. Neurochem. 2002, 80, 477-487.
    • (2002) J. Neurochem. , vol.80 , pp. 477-487
    • Barinka, C.1    Rinnova, M.2    Sacha, P.3    Rojas, C.4    Majer, P.5    Slusher, B.S.6    Konvalinka, J.7


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.