메뉴 건너뛰기




Volumn 53, Issue 4, 2010, Pages 1509-1518

Studies of the synthesis of all stereoisomers of MG-132 proteasome inhibitors in the tumor targeting approach

Author keywords

[No Author keywords available]

Indexed keywords

2 FORMAMIDO 4 METHYLPENTYL ACETATE; 2 ISOCYANO 4 METHYLPENTYL ACETATE; ALDEHYDE; AMINO 4 METHYLPENTAN 1 OL LEUCINOL; BENZYLOXYCARBONYLLEUCYLLEUCYLLEUCINAL; CHYMOTRYPSIN; ISOCYANO 4 METHYLPENTYL ACETATE; N [1 (HYDROXYMETHYL) 3 METHYLBUTYL]FORMAMIDE; TRIPEPTIDE; TRYPSIN; UNCLASSIFIED DRUG;

EID: 77649210502     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm901619n     Document Type: Article
Times cited : (36)

References (40)
  • 1
    • 0032558514 scopus 로고    scopus 로고
    • Design, of novel tripeptides with macrophage migration-enhancing activity
    • Nunami, K.-i.; Yamada, M.; Shimizu, R. Design, of novel tripeptides with macrophage migration-enhancing activity. Bioorg, Med, Chem. Lett 1998, 8, 2517-2520.
    • (1998) Bioorg, Med, Chem. Lett , vol.8 , pp. 2517-2520
    • Nunami, K.-I.1    Yamada, M.2    Shimizu, R.3
  • 2
    • 0032987794 scopus 로고    scopus 로고
    • Solid-phase synthesis of irreversible human rhinovirus 3C protease inhibitors. Part 1: Optimization of tripeptides incorporating N-terminal amides
    • Dragovich, P. S.; Zhou, R.; Skalitzky, D. J.; Fuhrman, S. A.; Patick, A. K.; Ford, C. E.; James, W.; Meador, I.; Worland, S. T. Solid-phase synthesis of irreversible human rhinovirus 3C protease inhibitors. Part 1: Optimization of tripeptides incorporating N-terminal amides. Bioorz. Med. Chem., 1999, 7, 589-598.
    • (1999) Bioorz. Med. Chem. , vol.7 , pp. 589-598
    • Dragovich, P.S.1    Zhou, R.2    Skalitzky, D.J.3    Fuhrman, S.A.4    Patick, A.K.5    Ford, C.E.6    James, W.7    Meador, I.8    Worland, S.T.9
  • 4
    • 0030591853 scopus 로고    scopus 로고
    • Peptide inhibitors of IKB protease: Modification of the C-termini of Z-LLF-CHO
    • Suto, M. J.; Sullivan, R. W.; Ransone, L. J. Peptide inhibitors of IKB protease: modification of the C-termini of Z-LLF-CHO. Bioorg, Med, Chem, Lett. 1996, 6, 2925-2930.
    • (1996) Bioorg, Med, Chem, Lett. , vol.6 , pp. 2925-2930
    • Suto, M.J.1    Sullivan, R.W.2    Ransone, L.J.3
  • 8
    • 15044349908 scopus 로고    scopus 로고
    • Structure-based design of derivatives of tyropeptin A as the potent and selective inhibitors of mammalian 20S proteasome
    • DOI 10.1016/j.bmcl.2005.02.013
    • Momose, I.; Umezawa, Y.; Hirosawa, S.; Iinuma, H.; Ikeda, D. Structure-based design of derivatives of tyropeptin A as the potent and selective inhibitors of mammalian 20S proteasome. Bioorg. Med, Chem, Lett. 2005, 15, 1867-1871. (Pubitemid 40380749)
    • (2005) Bioorganic and Medicinal Chemistry Letters , vol.15 , Issue.7 , pp. 1867-1871
    • Momose, I.1    Umezawa, Y.2    Hirosawa, S.3    Iinuma, H.4    Ikeda, D.5
  • 10
    • 34250011799 scopus 로고    scopus 로고
    • The ubiquitin-proteasome sysytem and its role in inflammatory and autoimmune diseases
    • Wang, J.; Maldonado, M. A. The ubiquitin-proteasome sysytem and its role in inflammatory and autoimmune diseases. Cell. Mol. Immunol. 2006, 3, 255-261.
    • (2006) Cell. Mol. Immunol. , vol.3 , pp. 255-261
    • Wang, J.1    Maldonado, M.A.2
  • 11
    • 23044506681 scopus 로고    scopus 로고
    • The ubiquitin-proteasome pathway and its role in cancer
    • DOI 10.1200/JCO.2005.05.081
    • Mani, A.; Gelmann, E. P. The ubiquitin-proteasome pathway and its role in cancer. J. Clin. 2005, 23, 4776-4789. (Pubitemid 46224082)
    • (2005) Journal of Clinical Oncology , vol.23 , Issue.21 , pp. 4776-4789
    • Mani, A.1    Gelmann, E.P.2
  • 12
    • 0141987860 scopus 로고    scopus 로고
    • The ubiquitin proteasome system in neurodegenerative diseases: Sometimes the chicken, sometimes the egg
    • DOI 10.1016/S0896-6273(03)00606-8
    • Ciechanover, A.; Brundin, P. The ubiquitin proteasome system in neurodegenerative diseases: sometimes the chicken, sometimes the egg. Neuron 2003, 40, 427-446. (Pubitemid 37244106)
    • (2003) Neuron , vol.40 , Issue.2 , pp. 427-446
    • Ciechanover, A.1    Brundin, P.2
  • 13
    • 0347987907 scopus 로고    scopus 로고
    • The ubiquitin-proteasome system in cardiovascular diseases - A hypothesis extended
    • DOI 10.1016/j.cardiores.2003.09.033
    • Herrmann, J.; Ciechanover, A.; Lerman, L. O.; Lerman, A. The ubiquitin-proteasome system, in cardiovascular diseases: a hypothesis extended. Cardiovasc. Res. 2004, 61, 11-21. (Pubitemid 38056676)
    • (2004) Cardiovascular Research , vol.61 , Issue.1 , pp. 11-21
    • Herrmann, J.1    Ciechanover, A.2    Lerman, L.O.3    Lerman, A.4
  • 14
    • 33745187107 scopus 로고    scopus 로고
    • TMC-95-based inhibitor design provides evidence for the catalytic versatility of the proteasome
    • DOI 10.1016/j.chembiol.2006.04.005, PII S1074552106001451
    • Groll, M.; Gotz, M.; Kaiser, M.; Weyher, E.; Moroder, L. TMC95-based inhibitor design provides evidence for the catalytic versatility of the proteasome. Chem. Biol. 2006, 13, 607-614. (Pubitemid 43912453)
    • (2006) Chemistry and Biology , vol.13 , Issue.6 , pp. 607-614
    • Groll, M.1    Gotz, M.2    Kaiser, M.3    Weyher, E.4    Moroder, L.5
  • 16
    • 0033230405 scopus 로고    scopus 로고
    • Towards subunit-specific proteasome inhibitors: Synthesis and evaluation, of peptide α,β- Epoxyketones
    • Elofsson, M.; Splittgerber, U.; Myung, J.; Mohan, R.; Crews, C. M. Towards subunit-specific proteasome inhibitors: synthesis and evaluation, of peptide α,β- epoxyketones. Chem. Biol. 1999, 6, 811822.
    • (1999) Chem. Biol. , vol.6 , pp. 811822
    • Elofsson, M.1    Splittgerber, U.2    Myung, J.3    Mohan, R.4    Crews, C.M.5
  • 18
    • 2342667387 scopus 로고    scopus 로고
    • The development of proteasome inhibitors as anticancer drugs
    • DOI 10.1016/S1535-6108(04)00120-5, PII S1535610804001205
    • Adams, J. The development of proteasome inhibitors as anticancer drugs. Cancer Cell 2004, 5, 417-421. (Pubitemid 38610244)
    • (2004) Cancer Cell , vol.5 , Issue.5 , pp. 417-421
    • Adams, J.1
  • 19
    • 34447108737 scopus 로고    scopus 로고
    • Caspase-8 dependent osteosarcoma cell apoptosis induced by proteasome inhibitor MG132
    • DOI 10.1016/j.cellbi.2007.03.037, PII S106569950700100X
    • Yan, X.-B.; Yang, D.-S.; Gao, X.; Feng, J.; Shi, Z.-L.; Ye, Z. Caspase-8 dependent osteosarcoma cell apoptosis induced by proteasome inhibitor MG132. Cell Biol. Int. 2007, 31,1136. (Pubitemid 47030977)
    • (2007) Cell Biology International , vol.31 , Issue.10 , pp. 1136-1143
    • Yan, X.-B.1    Yang, D.-S.2    Gao, X.3    Feng, J.4    Shi, Z.-L.5    Ye, Z.6
  • 20
    • 52949120373 scopus 로고    scopus 로고
    • Inactivation of NF-kB by proteasome inhibition, contributes to increased, apoptosis induced, by histone deacetylase inhibitors in human breast cancer cell
    • Domingo-Domenech, J.; Pippa, R.; Tapia, M.; Gascon, P.; Bachs, O.; Bosh, M. Inactivation of NF-kB by proteasome inhibition, contributes to increased, apoptosis induced, by histone deacetylase inhibitors in human breast cancer cell. Breast Cancer Res. Treat. 2008, 112, 53-62.
    • (2008) Breast Cancer Res. Treat. , vol.112 , pp. 53-62
    • Domingo-Domenech, J.1    Pippa, R.2    Tapia, M.3    Gascon, P.4    Bachs, O.5    Bosh, M.6
  • 21
    • 26844545414 scopus 로고    scopus 로고
    • The proteasome inhibitor MG-132 sensitizes PC-3 protease cancer cells to ionizing radiation by a DNA-PK-dependent mechanism
    • Pajonk, F.; Ophoven, A. v.; Weissenberger, C.; McBride, W. H. The proteasome inhibitor MG-132 sensitizes PC-3 protease cancer cells to ionizing radiation by a DNA-PK-dependent mechanism. BMC Cancer 2005, 5, 76.
    • (2005) BMC Cancer , vol.5 , pp. 76
    • Pajonk, F.1    Ophoven, A.V.2    Weissenberger, C.3    McBride, W.H.4
  • 23
    • 57049160340 scopus 로고    scopus 로고
    • Inhibition of the ubiquitin-proteasome prevents glutamate transporter degradation and morphine tolerance
    • Yang, L.;Wang, S.;Lim, G.; Sung, B.; Zeng, Q.;Mao, J. Inhibition of the ubiquitin-proteasome prevents glutamate transporter degradation and morphine tolerance. Pain 2008, 140, 472-478.
    • (2008) Pain , vol.140 , pp. 472-478
    • Yang, L.1    Wang, S.2    Lim, G.3    Sung, B.4    Zeng, Q.5    Mao, J.6
  • 24
    • 77649199527 scopus 로고    scopus 로고
    • Inhibitors of the 26S proteolytic complex and the 20S proteasome contained
    • Therein. U.S. Patent 5693617
    • Stein, R. L.; Ma, Y.-T.; Brand, S. Inhibitors of the 26S Proteolytic Complex and the 20S Proteasome Contained. Therein. U.S. Patent 5693617, 1997.
    • (1997)
    • Stein, R.L.1    Ma, Y.-T.2    Brand, S.3
  • 25
    • 0034154193 scopus 로고    scopus 로고
    • UPS on Weinreb resin: A facile solid-phase route to aldehyde and ketone derivatives of "unnatural" amino acids and peptides
    • O'Donnell, M. J.; Drew, M. D.; Pottorf, R. S.; Scott, W. L. UPS on. Weinreb resin: a facile solid-phase route to aldehyde and ketone derivatives of "unnatural" amino acids and peptides. J. Comb. Chem. 2002, 2, 172-181.
    • (2002) J. Comb. Chem. , vol.2 , pp. 172-181
    • O'Donnell, M.J.1    Drew, M.D.2    Pottorf, R.S.3    Scott, W.L.4
  • 27
    • 0032537532 scopus 로고    scopus 로고
    • Peptidyl β-homo-aspartals: Specific inhibitors of interleukin-1β converting enzyme and its homologues (caspases)
    • DOI 10.1016/S0960-894X(98)00244-3, PII S0960894X98002443
    • Bajusz, S.; Fauszt, I.; Nemeth, K.; Barabas, E.; Juhasz, A.; Patthy, M. Peptidyl β-homo aspartals: specific inhibitors ofinterleukin-1β converting enzyme and its homologues (caspases). Bioorg, Med, Chem, Lett. 1998, 8, 1477-1482. (Pubitemid 28281408)
    • (1998) Bioorganic and Medicinal Chemistry Letters , vol.8 , Issue.12 , pp. 1477-1482
    • Bajusz, S.1    Fauszt, I.2    Nemeth, K.3    Barabas, E.4    Juhasz, A.5    Patthy, M.6
  • 29
    • 34250783607 scopus 로고    scopus 로고
    • Studies on the application of the Passerini reaction and enzymatic procedures to the synthesis of tripeptide mimetics
    • DOI 10.1016/j.tet.2007.05.044, PII S0040402007009064
    • Szymaŕski, W.; Zwolínska, M.; Ostaszewski, R. Studies on the application of the Passerini reaction and enzymatic procedures to the synthesis of tripeptide mimetics. Tetrahedron 2007, 63, 76A77653. (Pubitemid 46962647)
    • (2007) Tetrahedron , vol.63 , Issue.32 , pp. 7647-7653
    • Szymanski, W.1    Zwolinska, M.2    Ostaszewski, R.3
  • 30
    • 38749096301 scopus 로고    scopus 로고
    • Design and synthesis of cyclic RGD pentapeptoids by consecutive Ugi reactions
    • Vercillo, O. E.; Andrade, C. K. Z.; Wessjohann, L. A. Design and synthesis of cyclic RGD pentapeptoids by consecutive Ugi reactions. Org. Lett. 2008, 10, 205-208.
    • (2008) Org. Lett. , vol.10 , pp. 205-208
    • Vercillo, O.E.1    Andrade, C.K.Z.2    Wessjohann, L.A.3
  • 31
    • 0017787242 scopus 로고
    • Peptide synthesis using four-component condensation. (Ugi reaction)
    • Waki, M.; Meienhofer, J. Peptide synthesis using four-component condensation. (Ugi reaction); J. Am. Chem. Sac. 1977, 99, 60756082.
    • (1977) J. Am. Chem. Sac. , vol.99 , pp. 60756082
    • Waki, M.1    Meienhofer, J.2
  • 32
    • 57549111251 scopus 로고    scopus 로고
    • On the preparation of enantiomerically pure isonitriles from, amino ester and peptides
    • Zhu, J.; Wu, X.; Danishefsky, S. J. On the preparation of enantiomerically pure isonitriles from, amino ester and peptides. Tetrahedron Lett. 2009, 50, 577-579.
    • (2009) Tetrahedron Lett. , vol.50 , pp. 577-579
    • Zhu, J.1    Wu, X.2    Danishefsky, S.J.3
  • 33
    • 49849106782 scopus 로고    scopus 로고
    • α-Amino acids as acid components in the Passerini reaction: Influence of N-protection on the yield, and stereoselectivity
    • Berlozecki, S.; Szymański, W.; Ostaszewski, R. α-Amino acids as acid components in the Passerini reaction: influence of N-protection on the yield, and stereoselectivity. Tetrahedron 2008, 64, 9780.
    • (2008) Tetrahedron , vol.64 , pp. 9780
    • Berlozecki, S.1    Szymański, W.2    Ostaszewski, R.3
  • 34
    • 0034956176 scopus 로고    scopus 로고
    • A new strategy for the synthesis of cyclopeptides containing diaminoglutaric acid
    • DOI 10.1002/psc.306
    • Bayer, T.; Riemer, C.; Kessler, H. A new strategy for the synthesis of cyclopeptides containing diaminoglutaric acid. J. Peat Sci. 2001, 7, 250-261. (Pubitemid 32586584)
    • (2001) Journal of Peptide Science , vol.7 , Issue.5 , pp. 250-261
    • Bayer, T.1    Riemer, C.2    Kessler, H.3
  • 35
    • 64249089461 scopus 로고    scopus 로고
    • A new and general method for the synthesis of tripeptide aldehydes based on the multi-component Ugi reaction
    • Mroczkiewicz M.; Ostaszewski, R. A new and general method for the synthesis of tripeptide aldehydes based on the multi-component Ugi reaction. Tetrahedron 2009, 65, 4025-4034.
    • (2009) Tetrahedron , vol.65 , pp. 4025-4034
    • Mroczkiewicz, M.1    Ostaszewski, R.2
  • 36
    • 0035801852 scopus 로고    scopus 로고
    • Concise total synthesis of the prolyl endopeptidase inhibitor eurystatin A via a novel Passerini reaction-deprotection-acyl migration strategy
    • Owens, T. D.; Araldi,G.-L.; Nutt, R. F.; Semple, J. E. Concise total synthesis of the prolyl endopeptidase inhibitor eurystatin A via a novel Passerini reaction-deprotection-acyl migration strategy. Tetrahedron Lett 2001, 42, 6271-6274.
    • (2001) Tetrahedron Lett , vol.42 , pp. 6271-6274
    • Owens, T.D.1    Araldi, G.-L.2    Nutt, R.F.3    Semple, J.E.4
  • 37
    • 34447098178 scopus 로고    scopus 로고
    • Chemoenzymatic synthesis of enantiomerically enriched α-hydroxyamides
    • DOI 10.1016/j.molcatb.2007.04.007, PII S1381117707000896
    • Szymaŕiski, W.; Ostaszewski, R. Chemoenzymatic synthesis of enantiomerically enriched α-hydroxyamides. J. Mol, Catal. B: Enzym 2007, 47, 125-128. (Pubitemid 47031674)
    • (2007) Journal of Molecular Catalysis B: Enzymatic , vol.47 , Issue.3-4 , pp. 125-128
    • Szymanski, W.1    Ostaszewski, R.2
  • 38
    • 34249341153 scopus 로고    scopus 로고
    • The study on efficient hydrolases immobilization for the kinetic resolution of the α-acetoxyamides
    • DOI 10.1016/j.molcatb.2007.03.007, PII S1381117707000677
    • Koszelewski, D.; Redzej, A.; Ostaszewski, R. The study on efficient hydrolases immobilisation for the kinetic resolution of α-acetoxyamides. J. Mol, Catal. B: Enzym. 2007, 47, 51-57. (Pubitemid 46819153)
    • (2007) Journal of Molecular Catalysis B: Enzymatic , vol.47 , Issue.1-2 , pp. 51-57
    • Koszelewski, D.1    Redzej, A.2    Ostaszewski, R.3
  • 39
    • 0037401443 scopus 로고    scopus 로고
    • Assessment of proteasome activity in cell lysates and tissue homogenates using peptide substrates
    • Rodgers, K. J.; Dean, R. T. Assessment of proteasome activity in cell lysates and tissue homogenates using peptide substrates. Int. J. Biochem. Cell Biol. 2003, 35, 716-727.
    • (2003) Int. J. Biochem. Cell Biol. , vol.35 , pp. 716-727
    • Rodgers, K.J.1    Dean, R.T.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.