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Volumn 45, Issue 23, 2002, Pages 5005-5022

Identification of potent and selective small-molecule inhibitors of caspase-3 through the use of extended tethering and structure-based drug design

Author keywords

[No Author keywords available]

Indexed keywords

CASPASE 3 INHIBITOR; SMALL MOLECULE TRANSPORT AGENT;

EID: 0037038325     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm020230j     Document Type: Article
Times cited : (120)

References (50)
  • 1
    • 0343433408 scopus 로고    scopus 로고
    • Cysteine proteases and their inhibitors
    • Otto, H.; Schirmeister, T. Cysteine proteases and their inhibitors. Chem. Rev. 1997, 97, 133-171.
    • (1997) Chem. Rev. , vol.97 , pp. 133-171
    • Otto, H.1    Schirmeister, T.2
  • 2
    • 0034628448 scopus 로고    scopus 로고
    • Protease inhibitors: Current status and future prospects
    • Leung, D.; Abbenante, G.; Fairlie, D. P. Protease inhibitors: Current status and future prospects. J. Med. Chem. 2000, 43, 305-341.
    • (2000) J. Med. Chem. , vol.43 , pp. 305-341
    • Leung, D.1    Abbenante, G.2    Fairlie, D.P.3
  • 3
    • 0034618635 scopus 로고    scopus 로고
    • Caspases as targets for antiinflammatory and anti-apoptotic drug discovery
    • Talanian, R. V.; Brady, K. D.; Cryns, V. L. Caspases as targets for antiinflammatory and anti-apoptotic drug discovery. J. Med. Chem. 2000, 43, 3351-3371.
    • (2000) J. Med. Chem. , vol.43 , pp. 3351-3371
    • Talanian, R.V.1    Brady, K.D.2    Cryns, V.L.3
  • 5
    • 0032078217 scopus 로고    scopus 로고
    • Caspases: Key mediators of apoptosis
    • Thornberry, N. A. Caspases: Key mediators of apoptosis. Chem. Biol. 1998, 5, R97-R103.
    • (1998) Chem. Biol. , vol.5
    • Thornberry, N.A.1
  • 10
    • 0034641918 scopus 로고    scopus 로고
    • The biochemistry of apoptosis
    • Hengartner, M. O. The biochemistry of apoptosis. Nature 2000, 407, 770-776.
    • (2000) Nature , vol.407 , pp. 770-776
    • Hengartner, M.O.1
  • 11
    • 0000191650 scopus 로고
    • Interleukin-1b converting enzyme: Biology and the chemistry of inhibitors
    • Ator, M. A.; Dolle, R. E. Interleukin-1b converting enzyme: Biology and the chemistry of inhibitors. Curr. Pharm. Des. 1995, 1, 191-210.
    • (1995) Curr. Pharm. Des. , vol.1 , pp. 191-210
    • Ator, M.A.1    Dolle, R.E.2
  • 12
    • 0001488060 scopus 로고    scopus 로고
    • Emerging therapeutic targets in caspase-dependent disease
    • McBride, C. B.; McPhail, L. T.; Steeves, J. D. Emerging Therapeutic targets in caspase-dependent disease. Emerging Ther. Targets 1999, 3, 391-411.
    • (1999) Emerging Ther. Targets , vol.3 , pp. 391-411
    • McBride, C.B.1    McPhail, L.T.2    Steeves, J.D.3
  • 13
    • 0033815948 scopus 로고    scopus 로고
    • Neuronal apoptosis as a therapeutic target in neurodegenerative disease
    • Larner, A. J. Neuronal apoptosis as a therapeutic target in neurodegenerative disease. Exp. Opin. Ther. Pat. 2000, 10, 1493-1518.
    • (2000) Exp. Opin. Ther. Pat. , vol.10 , pp. 1493-1518
    • Larner, A.J.1
  • 14
    • 0034641932 scopus 로고    scopus 로고
    • From bench to clinic with apoptosis-based therapeutic agents
    • and references therein
    • Nicholson, D. W. From bench to clinic with apoptosis-based therapeutic agents. Nature 2000, 407, 810-816 and references therein.
    • (2000) Nature , vol.407 , pp. 810-816
    • Nicholson, D.W.1
  • 15
    • 0036463649 scopus 로고    scopus 로고
    • Apoptosis-based therapies
    • Reed, J. C. Apoptosis-based therapies. Nat. Rev. Drug Discovery 2002, 1, 111-121.
    • (2002) Nat. Rev. Drug Discovery , vol.1 , pp. 111-121
    • Reed, J.C.1
  • 17
    • 0035980006 scopus 로고    scopus 로고
    • Evidence that inhibition of cathepsin-B contributes to the neuroprotective properties of caspase inhibitor tyr-val-ala-asp-chloromethyl ketone
    • Gray, J.; Haran, M. M.; Schneider, K.; Vesce, S.; Ray, A. M.; Owen, D.; White, I. R.; Cutler, P.; Davis, J. B. Evidence that inhibition of cathepsin-B contributes to the neuroprotective properties of caspase inhibitor tyr-val-ala-asp-chloromethyl ketone. J. Biol. Chem. 2001, 276, 32750-32755.
    • (2001) J. Biol. Chem. , vol.276 , pp. 32750-32755
    • Gray, J.1    Haran, M.M.2    Schneider, K.3    Vesce, S.4    Ray, A.M.5    Owen, D.6    White, I.R.7    Cutler, P.8    Davis, J.B.9
  • 19
    • 0011091079 scopus 로고    scopus 로고
    • Idun Pharmaceuticals, Inc. (Substituted) Acyl Dipeptidyl Inhibitors of the ICE/ced-3 Family of Cysteine Proteases. WO0023421, 2000
    • Idun Pharmaceuticals, Inc. (Substituted) Acyl Dipeptidyl Inhibitors of the ICE/ced-3 Family of Cysteine Proteases. WO0023421, 2000.
  • 20
    • 0011156166 scopus 로고    scopus 로고
    • Merck Frosst Canada and Co. Nicotinyl Aspartyl Ketones as Inhibitors of Caspase-3. WO0127085 A1, 2001
    • Merck Frosst Canada and Co. Nicotinyl Aspartyl Ketones as Inhibitors of Caspase-3. WO0127085 A1, 2001.
  • 21
    • 0033520777 scopus 로고    scopus 로고
    • General solid-phase method for the preparation of mechanism-based cysteine protease inhibitors
    • Lee, A.; Huang, L.; Ellman, J. A. General solid-phase method for the preparation of mechanism-based cysteine protease inhibitors. J. Am. Chem. Soc. 1999, 121, 9907-9914.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 9907-9914
    • Lee, A.1    Huang, L.2    Ellman, J.A.3
  • 23
    • 0030480485 scopus 로고    scopus 로고
    • Synthesis and angiotensin II receptor antagonistic activities of benzimidazole derivatives bearing acidic heterocycles as novel tetrazole bioisosteres
    • Kohara, Y.; Kubo, K.; Imamiya, E.; Wada, T.; Inada, Y.; Naka, T. Synthesis and angiotensin II receptor antagonistic activities of benzimidazole derivatives bearing acidic heterocycles as novel tetrazole bioisosteres. J. Med. Chem. 1996, 39, 5228-5235.
    • (1996) J. Med. Chem. , vol.39 , pp. 5228-5235
    • Kohara, Y.1    Kubo, K.2    Imamiya, E.3    Wada, T.4    Inada, Y.5    Naka, T.6
  • 24
    • 0028871612 scopus 로고
    • A new asymmetric synthesis of (S)-dolaphenin and its heteroaromatic congeners utilizing (+)-2-Hydroxy-3-pinanone and (-)-3-Hydroxy-2-caranone as chiral auxiliaries
    • Irako, N.; Hamada, Y.; Shioiri, T. A new asymmetric synthesis of (S)-dolaphenin and its heteroaromatic congeners utilizing (+)-2-Hydroxy-3-pinanone and (-)-3-Hydroxy-2-caranone as chiral auxiliaries. Tetrahedron 1995, 51, 12731-12744.
    • (1995) Tetrahedron , vol.51 , pp. 12731-12744
    • Irako, N.1    Hamada, Y.2    Shioiri, T.3
  • 25
    • 0000302622 scopus 로고
    • Synthesis of two new thiazole-containing oligopeptides as potential DNA minor groove binding analogues of netropsin
    • Plouvier, B.; Bailly, C.; Houssin, R.; Henichart, J.-P. Synthesis of two new thiazole-containing oligopeptides as potential DNA minor groove binding analogues of netropsin. Heterocycles 1991, 32, 693-701.
    • (1991) Heterocycles , vol.32 , pp. 693-701
    • Plouvier, B.1    Bailly, C.2    Houssin, R.3    Henichart, J.-P.4
  • 26
    • 0003382062 scopus 로고
    • Facile synthesis of polyfunctionally substituted pyridines from ethoxycarbonylmalonaldehyde
    • Torii, S.; Inokuchi, T.; Kubota, M. A. Facile synthesis of polyfunctionally substituted pyridines from ethoxycarbonylmalonaldehyde. Synthesis 1986, 400-402.
    • (1986) Synthesis , pp. 400-402
    • Torii, S.1    Inokuchi, T.2    Kubota, M.A.3
  • 27
    • 0014384744 scopus 로고
    • Syntheses of 2-acylaminoacetamidine and 3-acylaminopropionamidine derivatives
    • Ueda, T.; Okamoto, Y.; Tsuji, T.; Muraoka, M. Syntheses of 2-acylaminoacetamidine and 3-acylaminopropionamidine derivatives. Chem. Pharm. Bull. 1968, 16, 2355-2361.
    • (1968) Chem. Pharm. Bull. , vol.16 , pp. 2355-2361
    • Ueda, T.1    Okamoto, Y.2    Tsuji, T.3    Muraoka, M.4
  • 28
    • 0000073369 scopus 로고
    • Researches on pyrimidines. CXL. Pyrimidines from carbethoxymalonic aldehyde
    • Dyer, E.; Johnson, T. Researches on pyrimidines. CXL. pyrimidines from carbethoxymalonic aldehyde. J. Am. Chem. Soc. 1934, 56, 222-225.
    • (1934) J. Am. Chem. Soc. , vol.56 , pp. 222-225
    • Dyer, E.1    Johnson, T.2
  • 30
    • 0011085150 scopus 로고    scopus 로고
    • Lombardino, J. G.; Harbert, C. A. Antiinflammatory and immunoregulatory pyrimidines, their method of use and pharmaceutical compositions. U. S. Patent 4,246,263, 1981
    • Lombardino, J. G.; Harbert, C. A. Antiinflammatory and immunoregulatory pyrimidines, their method of use and pharmaceutical compositions. U. S. Patent 4,246,263, 1981.
  • 31
    • 0030581367 scopus 로고    scopus 로고
    • Optically active 2H-azepines: Synthesis and rearrangement into their 3H-isomers
    • Hamprecht, D.; Josten, J.; Steglich, W. Optically active 2h-Azepines: Synthesis and rearrangement into their 3H-isomers. Tetrahedron 1996, 52, 10883-10902.
    • (1996) Tetrahedron , vol.52 , pp. 10883-10902
    • Hamprecht, D.1    Josten, J.2    Steglich, W.3
  • 32
    • 0030880683 scopus 로고    scopus 로고
    • Convenient preparations of tert-butyl esters and ethers from tert-butyl alcohol
    • Wright, S. W.; Hageman, D. L.; Wright, A. S.; McClure, L. D. Convenient preparations of tert-butyl esters and ethers from tert-butyl alcohol. Tetrahedron Lett. 1997, 38, 7345-7348.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 7345-7348
    • Wright, S.W.1    Hageman, D.L.2    Wright, A.S.3    McClure, L.D.4
  • 33
    • 85082949923 scopus 로고
    • A convenient preparation of tert-butyl esters
    • Widmer. U. A convenient preparation of tert-butyl esters. Synthesis 1983, 135-136.
    • (1983) Synthesis , pp. 135-136
    • Widmer, U.1
  • 34
    • 0011150136 scopus 로고    scopus 로고
    • Vertex Pharmaceuticals, Inc. Inhibitors of Interleukin-1β Converting Enzyme. U. S. Patent 6,103,711, 2000
    • Vertex Pharmaceuticals, Inc. Inhibitors of Interleukin-1β Converting Enzyme. U. S. Patent 6,103,711, 2000.
  • 35
    • 0027729682 scopus 로고
    • Phenylalkyl ketones as potent reversible inhibitors of interleukin-1β converting enzyme
    • Mjalli, A. M.; Chapman, K. T.; MacCoss, M.; Thornberry, N. A. Phenylalkyl ketones as potent reversible inhibitors of interleukin-1β converting enzyme. Bioorg. Med. Chem. Lett. 1993, 3, 2689-2692.
    • (1993) Bioorg. Med. Chem. Lett. , vol.3 , pp. 2689-2692
    • Mjalli, A.M.1    Chapman, K.T.2    MacCoss, M.3    Thornberry, N.A.4
  • 36
    • 0033036804 scopus 로고    scopus 로고
    • A catalytic mechanism for caspase-1 for bimodal inhibition of caspase-1 by activated aspartic ketones
    • Brady, K. D.; Giegel, D. A.; Grinnell, C.; Lunney, E.; Talanian, R. V.; Wong, W.; Walker, N. A catalytic mechanism for caspase-1 and for bimodal inhibition of caspase-1 by activated aspartic ketones. Bioorg. Med. Chem. 1999, 7, 621-631.
    • (1999) Bioorg. Med. Chem. , vol.7 , pp. 621-631
    • Brady, K.D.1    Giegel, D.A.2    Grinnell, C.3    Lunney, E.4    Talanian, R.V.5    Wong, W.6    Walker, N.7
  • 43
    • 0037571112 scopus 로고    scopus 로고
    • Merck molecular force field. I. Basis, form, scope, parametrization and performance of MMFF94
    • Halgren, T. A.; Merck molecular force field. I. Basis, form, scope, parametrization and performance of MMFF94. J. Comput. Chem. 1996, 17, 490.
    • (1996) J. Comput. Chem. , vol.17 , pp. 490
    • Halgren, T.A.1
  • 45
    • 0001398008 scopus 로고    scopus 로고
    • How well does a restrained electrostatic potential (RESP) model perform in calculating conformational energies of organic and biological molecules?
    • Wang, J.; Cieplak, P.; Kollman, P. How well does a restrained electrostatic potential (RESP) model perform in calculating conformational energies of organic and biological molecules? J. Comput. Chem. 2000, 21, 1049-1074.
    • (2000) J. Comput. Chem. , vol.21 , pp. 1049-1074
    • Wang, J.1    Cieplak, P.2    Kollman, P.3
  • 46
    • 0033213239 scopus 로고    scopus 로고
    • The finer things in X-ray diffraction data collection
    • Pflugrath, J. W. The finer things in X-ray diffraction data collection. Acta Crystallogr. 1999, D55, 1718-1725.
    • (1999) Acta Crystallogr. , vol.D55 , pp. 1718-1725
    • Pflugrath, J.W.1
  • 48
    • 0028103275 scopus 로고
    • CCP4. Programs for protein crystallography
    • CCP4. Programs for protein crystallography. Acta Crystallogr. 1994, D50, 760-763.
    • (1994) Acta Crystallogr. , vol.D50 , pp. 760-763
  • 49
    • 84889120137 scopus 로고
    • Improved methods for binding protein models in electron density maps and the location of errors in these models
    • Jones, T. A.; Zou, J. Y.; Cowan, S. W.; Kjeldgaard, M. Improved methods for binding protein models in electron density maps and the location of errors in these models. Acta Crystallogr. 1991, A47, 110-119.
    • (1991) Acta Crystallogr. , vol.A47 , pp. 110-119
    • Jones, T.A.1    Zou, J.Y.2    Cowan, S.W.3    Kjeldgaard, M.4
  • 50
    • 84920325457 scopus 로고
    • AMoRe: An automated package for molecular replacement
    • Navaza, J. AMoRe: An automated package for molecular replacement. Acta Crystallogr. 1994, D50, 157-163.
    • (1994) Acta Crystallogr. , vol.D50 , pp. 157-163
    • Navaza, J.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.