메뉴 건너뛰기




Volumn 40, Issue 12, 1997, Pages 1906-1918

Dual inhibition of human leukocyte elastase and lipid peroxidation: In vitro and in vivo activities of azabicyclo[2.2.2]octane and perhydroindole derivatives

Author keywords

[No Author keywords available]

Indexed keywords

4 [[[[4 CHLORO 3 [[[[(4 HYDROXY 3,5 DI TERT BUTYLPHENYL) THIO]ACETYL]AMINO]SULFONYL]PHENYL]CARBONYL]AMINO] SULFONYL]BENZOYLVALYLPERHYDROINDOLE 2 CARBOXYLVALINE TRIFLUOROMETHYL KETONE; ELASTASE INHIBITOR; LEUKOCYTE ELASTASE; N [4 [(4 CHLOROPHENYLSULFONYL)AMINOCARBONYL]BENZOYL]VALYLPROLYLVALYL TRIFLUOROMETHYL KETONE; UNCLASSIFIED DRUG;

EID: 0030963186     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm960772z     Document Type: Article
Times cited : (10)

References (32)
  • 1
    • 0028282060 scopus 로고
    • Synthetic Inhibitors of Elastase
    • For a complete review on HLE and its synthetic inhibitors, see: Edwards, P. D.; Berstein, P. R. Synthetic Inhibitors of Elastase. Med. Res. Rev. 1994, 14, 127-194.
    • (1994) Med. Res. Rev. , vol.14 , pp. 127-194
    • Edwards, P.D.1    Berstein, P.R.2
  • 2
    • 0021919760 scopus 로고
    • Elastase and Emphysema. Current Assessment of the Protease-Antiprotease Hypothesis
    • Janoff, A. Elastase and Emphysema. Current Assessment of the Protease-Antiprotease Hypothesis. Am. Rev. Respir. Dis. 1985, 132, 417-433.
    • (1985) Am. Rev. Respir. Dis. , vol.132 , pp. 417-433
    • Janoff, A.1
  • 4
    • 0027302534 scopus 로고
    • Elastase and Oxygen Radicals: Synergistic Interactions
    • Hanley, M. E.; Repine, J. E. Elastase and Oxygen Radicals: synergistic Interactions. Agents Action 1993, Suppl. 42, 39-47.
    • (1993) Agents Action , Issue.42 SUPPL. , pp. 39-47
    • Hanley, M.E.1    Repine, J.E.2
  • 5
    • 34547384718 scopus 로고
    • Probucol, an oral hypocholesterolemic agent, inhibits acute tobacco smoking induced decrease in plasma antielastase activity and ferroxydase activity in rats
    • Elsevier: New York
    • Ishizaki, T.; Kishi, Y.; Sasaki, F.; Takahashi, H.; Ameshima, S.; Onishi, T.; Sakai, T.; Kasamatsu, A.; Nakai, T.; Miyabo, S. Probucol, an oral hypocholesterolemic agent, inhibits acute tobacco smoking induced decrease in plasma antielastase activity and ferroxydase activity in rats. Oxygen Radicals; Elsevier: New York, 1992; pp 573-576. Kim Seow, W.; Thong, Y. H.; Nelson, R. D.; Macfarlane, G. D.; Herzberg, M. C. Nicotine-induced Release of Elastase and Eicosanoids by Human Neutrophils. Inflammation 1994, 18, 119-127.
    • (1992) Oxygen Radicals , pp. 573-576
    • Ishizaki, T.1    Kishi, Y.2    Sasaki, F.3    Takahashi, H.4    Ameshima, S.5    Onishi, T.6    Sakai, T.7    Kasamatsu, A.8    Nakai, T.9    Miyabo, S.10
  • 6
    • 0028361915 scopus 로고
    • Nicotine-induced Release of Elastase and Eicosanoids by Human Neutrophils
    • Ishizaki, T.; Kishi, Y.; Sasaki, F.; Takahashi, H.; Ameshima, S.; Onishi, T.; Sakai, T.; Kasamatsu, A.; Nakai, T.; Miyabo, S. Probucol, an oral hypocholesterolemic agent, inhibits acute tobacco smoking induced decrease in plasma antielastase activity and ferroxydase activity in rats. Oxygen Radicals; Elsevier: New York, 1992; pp 573-576. Kim Seow, W.; Thong, Y. H.; Nelson, R. D.; Macfarlane, G. D.; Herzberg, M. C. Nicotine-induced Release of Elastase and Eicosanoids by Human Neutrophils. Inflammation 1994, 18, 119-127.
    • (1994) Inflammation , vol.18 , pp. 119-127
    • Kim Seow, W.1    Thong, Y.H.2    Nelson, R.D.3    Macfarlane, G.D.4    Herzberg, M.C.5
  • 7
    • 0029021239 scopus 로고
    • ICI 200 880
    • For a short review on ICI 200 880, see: Edwards, P. D. ICI 200 880. Drugs Future 1995, 20, 662-665.
    • (1995) Drugs Future , vol.20 , pp. 662-665
    • Edwards, P.D.1
  • 8
    • 0026404402 scopus 로고
    • Biochemistry and Pharmacology of ICI 200,880, a Synthetic Peptide Inhibitor of Human Neutrophil Elastase
    • Williams, J. C.; Stein, R. L.; Giles, R. E.; Krell, R. D. Biochemistry and Pharmacology of ICI 200,880, a Synthetic Peptide Inhibitor of Human Neutrophil Elastase. Ann. N. Y. Acad. Sci. 1991, 624, 230-243.
    • (1991) Ann. N. Y. Acad. Sci. , vol.624 , pp. 230-243
    • Williams, J.C.1    Stein, R.L.2    Giles, R.E.3    Krell, R.D.4
  • 12
    • 0029977323 scopus 로고    scopus 로고
    • New Prolyl endopeptidase inhibitors: In vitro and in vivo activities of azabicyclo[2.2.2]octane, azabicyclo[2.2.1]heptane, and perhydroindole derivatives
    • Portevin, B.; Benoist, A.; Rémond, G.; Hervé, Y.; Vincent, M.; Lepagnol, J.; De Nanteuil, G. New Prolyl endopeptidase inhibitors: in vitro and in vivo activities of azabicyclo[2.2.2]octane, azabicyclo[2.2.1]heptane, and perhydroindole derivatives. J. Med. Chem. 1996, 39, 2379-2391.
    • (1996) J. Med. Chem. , vol.39 , pp. 2379-2391
    • Portevin, B.1    Benoist, A.2    Rémond, G.3    Hervé, Y.4    Vincent, M.5    Lepagnol, J.6    De Nanteuil, G.7
  • 15
    • 0019956577 scopus 로고
    • Stereoselective Synthesis of new Perhydroindole Derivative of Chiral Iminoacid, a potent Inhibitor of Angiotensin Converting Enzyme
    • Vincent, M.; Rémond, G.; Portevin, B.; Serkiz, B.; Laubie, M. Stereoselective Synthesis of new Perhydroindole Derivative of Chiral Iminoacid, a potent Inhibitor of Angiotensin Converting Enzyme. Tetrahedron Lett. 1982, 23, 1677-1680.
    • (1982) Tetrahedron Lett. , vol.23 , pp. 1677-1680
    • Vincent, M.1    Rémond, G.2    Portevin, B.3    Serkiz, B.4    Laubie, M.5
  • 16
    • 0026440870 scopus 로고
    • Synthesis and Conformational Studies of Zabicipril (S 9650-3), a potent Inhibitor of Angiotensin Converting Enzyme
    • Vincent, M.; Pascard, C.; Césario, M.; Rémond, G.; Bouchet, J. P.; Charton, Y.; Laubie, M. Synthesis and Conformational Studies of Zabicipril (S 9650-3), a potent Inhibitor of Angiotensin Converting Enzyme. Tetrahedron Lett. 1992, 33, 7369-7372.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 7369-7372
    • Vincent, M.1    Pascard, C.2    Césario, M.3    Rémond, G.4    Bouchet, J.P.5    Charton, Y.6    Laubie, M.7
  • 18
    • 0025176920 scopus 로고
    • Synthesis of Peptidyl Fluoromethyl Ketones and Peptidyl α-Keto Esters as Inhibitors of Porcine Pancreatic Elastase, Human Neutrophil Elastase, and Rat and Human Neutrophil Cathepsin G
    • Peet, N. P.; Burkhart, J. P.; Angelastro, M. R.; Giroux, E. L.; Mehdi, S.; Bey, P.; Kolb, M.; Neises, B.; Schirlin, D. Synthesis of Peptidyl Fluoromethyl Ketones and Peptidyl α-Keto Esters as Inhibitors of Porcine Pancreatic Elastase, Human Neutrophil Elastase, and Rat and Human Neutrophil Cathepsin G. J. Med. Chem. 1990, 33, 394-407.
    • (1990) J. Med. Chem. , vol.33 , pp. 394-407
    • Peet, N.P.1    Burkhart, J.P.2    Angelastro, M.R.3    Giroux, E.L.4    Mehdi, S.5    Bey, P.6    Kolb, M.7    Neises, B.8    Schirlin, D.9
  • 19
    • 15444354692 scopus 로고    scopus 로고
    • Epimerization on the C-terminal valine for the two diastereomers of compound 14a was observed either in solution (pH and temperature dependent mechanism) or under solid form (temperature dependent mechanism)
    • Epimerization on the C-terminal valine for the two diastereomers of compound 14a was observed either in solution (pH and temperature dependent mechanism) or under solid form (temperature dependent mechanism).
  • 23
    • 15444339896 scopus 로고    scopus 로고
    • Trolox = 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid
    • Trolox = 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid.
  • 25
    • 15444338854 scopus 로고    scopus 로고
    • For the selectivity studies, compound 14a was evaluated on the following reptors: α1A, α1B, α2A, α2B, α2C, β1, β2, 5HT1A, 5HT1B, 5HT1D, 5HT2C, 5HT3, M1, M2, M3, NK1, NK2, D1, D2, D3, D4, A1, H1, and μ
    • For the selectivity studies, compound 14a was evaluated on the following reptors: α1A, α1B, α2A, α2B, α2C, β1, β2, 5HT1A, 5HT1B, 5HT1D, 5HT2C, 5HT3, M1, M2, M3, NK1, NK2, D1, D2, D3, D4, A1, H1, and μ.
  • 27
    • 0030009748 scopus 로고    scopus 로고
    • Nonpeptidic Inhibitors of Human Neutrophil Elastase. 7. Design, Synthesis, and in Vitro Activity of a Series of Pyrimidopyrimidine Trifluoromethyl Ketones
    • Edwards, P. D.; Andisik, D. W.; Strimpler, A. M.; Gomes, B.; Tuthill, P. A. Nonpeptidic Inhibitors of Human Neutrophil Elastase. 7. Design, Synthesis, and in Vitro Activity of a Series of Pyrimidopyrimidine Trifluoromethyl Ketones. J. Med. Chem. 1996, 39, 1112-1124.
    • (1996) J. Med. Chem. , vol.39 , pp. 1112-1124
    • Edwards, P.D.1    Andisik, D.W.2    Strimpler, A.M.3    Gomes, B.4    Tuthill, P.A.5
  • 28
    • 0019490262 scopus 로고
    • The Moderation of Elastase-induced Emphysema in the Hamster by Intratracheal Pretreatment or Post-treatment with Succinyl Alanyl Alanyl Prolyl Valine Chloromethyl Ketone
    • Stone, P. J.; Lucey, E. C.; Calore, J. D.; Snider, G. L.; Franzblau, C.; Castillo, M. J.; Powers, J. C. The Moderation of Elastase-induced Emphysema in the Hamster by Intratracheal Pretreatment or Post-treatment with Succinyl Alanyl Alanyl Prolyl Valine Chloromethyl Ketone. Am. Rev. Respir. Dis. 1981, 124, 56-59.
    • (1981) Am. Rev. Respir. Dis. , vol.124 , pp. 56-59
    • Stone, P.J.1    Lucey, E.C.2    Calore, J.D.3    Snider, G.L.4    Franzblau, C.5    Castillo, M.J.6    Powers, J.C.7
  • 29
    • 0021181956 scopus 로고
    • Similarities between Human and Rat Leucocyte Elastase and Cathepsin G
    • Virca, G. D.; Metz, G.; Schnebli, H. P. Similarities between Human and Rat Leucocyte Elastase and Cathepsin G. Eur. J. Biochem. 1984, 144, 1-9.
    • (1984) Eur. J. Biochem. , vol.144 , pp. 1-9
    • Virca, G.D.1    Metz, G.2    Schnebli, H.P.3
  • 30
    • 0017872475 scopus 로고
    • Microsomal lipid peroxidation
    • Fluscter, S., Pucher, L., Eds.; Academic Press: San Diego, CA
    • Nuege, J. A.; Aust, S. D. Microsomal lipid peroxidation. In Methods in Enzymology; Fluscter, S., Pucher, L., Eds.; Academic Press: San Diego, CA, 1987; Vol. 52, pp 302-310.
    • (1987) Methods in Enzymology , vol.52 , pp. 302-310
    • Nuege, J.A.1    Aust, S.D.2
  • 31
    • 33745026603 scopus 로고
    • The distribution and chemical composition of ultracentrifugally separated lipoproteines in human serum
    • Havel, R. J.; Eder, H. A.; Bragdon, J. H. The distribution and chemical composition of ultracentrifugally separated lipoproteines in human serum. J. Clin. Invest. 1955, 34, 1345-1353.
    • (1955) J. Clin. Invest. , vol.34 , pp. 1345-1353
    • Havel, R.J.1    Eder, H.A.2    Bragdon, J.H.3
  • 32
    • 84908879595 scopus 로고
    • Quantitative methods in the study of pulmonary pathology
    • Dunnill, M. S. Quantitative methods in the study of pulmonary pathology. Thorax 1962, 17, 320-328.
    • (1962) Thorax , vol.17 , pp. 320-328
    • Dunnill, M.S.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.