Crystal structure of NS-134 in complex with bovine cathepsin B: a two-headed epoxysuccinyl inhibitor extends along the entire active-site cleft

Stern I, Schaschke N, Moroder L, Turk D (2004)
BIOCHEMICAL JOURNAL 381(2): 511-517.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
Download
Es wurden keine Dateien hochgeladen. Nur Publikationsnachweis!
DOI
Autor*in
Stern, I; Schaschke, NorbertUniBi; Moroder, L; Turk, D
Einrichtung
Fakultät für Chemie > Organische Chemie III
Erscheinungsjahr
2004
Zeitschriftentitel
BIOCHEMICAL JOURNAL
Band
381
Ausgabe
2
Seite(n)
511-517
ISSN
0264-6021
eISSN
1470-8728
Page URI
https://pub.uni-bielefeld.de/record/2403774

Zitieren

Stern I, Schaschke N, Moroder L, Turk D. Crystal structure of NS-134 in complex with bovine cathepsin B: a two-headed epoxysuccinyl inhibitor extends along the entire active-site cleft. BIOCHEMICAL JOURNAL. 2004;381(2):511-517.
Stern, I., Schaschke, N., Moroder, L., & Turk, D. (2004). Crystal structure of NS-134 in complex with bovine cathepsin B: a two-headed epoxysuccinyl inhibitor extends along the entire active-site cleft. BIOCHEMICAL JOURNAL, 381(2), 511-517. https://doi.org/10.1042/bj20040237
Stern, I, Schaschke, Norbert, Moroder, L, and Turk, D. 2004. “Crystal structure of NS-134 in complex with bovine cathepsin B: a two-headed epoxysuccinyl inhibitor extends along the entire active-site cleft”. BIOCHEMICAL JOURNAL 381 (2): 511-517.
Stern, I., Schaschke, N., Moroder, L., and Turk, D. (2004). Crystal structure of NS-134 in complex with bovine cathepsin B: a two-headed epoxysuccinyl inhibitor extends along the entire active-site cleft. BIOCHEMICAL JOURNAL 381, 511-517.
Stern, I., et al., 2004. Crystal structure of NS-134 in complex with bovine cathepsin B: a two-headed epoxysuccinyl inhibitor extends along the entire active-site cleft. BIOCHEMICAL JOURNAL, 381(2), p 511-517.
I. Stern, et al., “Crystal structure of NS-134 in complex with bovine cathepsin B: a two-headed epoxysuccinyl inhibitor extends along the entire active-site cleft”, BIOCHEMICAL JOURNAL, vol. 381, 2004, pp. 511-517.
Stern, I., Schaschke, N., Moroder, L., Turk, D.: Crystal structure of NS-134 in complex with bovine cathepsin B: a two-headed epoxysuccinyl inhibitor extends along the entire active-site cleft. BIOCHEMICAL JOURNAL. 381, 511-517 (2004).
Stern, I, Schaschke, Norbert, Moroder, L, and Turk, D. “Crystal structure of NS-134 in complex with bovine cathepsin B: a two-headed epoxysuccinyl inhibitor extends along the entire active-site cleft”. BIOCHEMICAL JOURNAL 381.2 (2004): 511-517.

16 Zitationen in Europe PMC

Daten bereitgestellt von Europe PubMed Central.

Selective targeting of tumor and stromal cells by a nanocarrier system displaying lipidated cathepsin B inhibitor.
Mikhaylov G, Klimpel D, Schaschke N, Mikac U, Vizovisek M, Fonovic M, Turk V, Turk B, Vasiljeva O., Angew Chem Int Ed Engl 53(38), 2014
PMID: 24975267
Foot-and-mouth disease virus leader proteinase: structural insights into the mechanism of intermolecular cleavage.
Steinberger J, Grishkovskaya I, Cencic R, Juliano L, Juliano MA, Skern T., Virology 468-470(), 2014
PMID: 25240326
Expression characterization and activity analysis of a cathepsin B from Pacific abalone Haliotis discus hannai.
Qiu R, Liu X, Hu YH, Sun BG., Fish Shellfish Immunol 34(5), 2013
PMID: 23473863
E-64c-hydrazide: a lead structure for the development of irreversible cathepsin C inhibitors.
Radzey H, Rethmeier M, Klimpel D, Grundhuber M, Sommerhoff CP, Schaschke N., ChemMedChem 8(8), 2013
PMID: 23780739
Foot and mouth disease leader protease (Lbpro): Investigation of prime side specificity allows the synthesis of a potent inhibitor.
Nogueira Santos JA, Assis DM, Gouvea IE, Júdice WA, Izidoro MA, Juliano MA, Skern T, Juliano L., Biochimie 94(3), 2012
PMID: 22085639
Collagenolytic activities of the major secreted cathepsin L peptidases involved in the virulence of the helminth pathogen, Fasciola hepatica.
Robinson MW, Corvo I, Jones PM, George AM, Padula MP, To J, Cancela M, Rinaldi G, Tort JF, Roche L, Dalton JP., PLoS Negl Trop Dis 5(4), 2011
PMID: 21483711
Inhibition of cathepsin L by epoxysuccinyl peptides simultaneously addressing active-site and remote-site regions.
Schaschke N, Assfalg-Machleidt I, Machleidt W., Chembiochem 9(11), 2008
PMID: 18551692
Peptidyl epoxides extended in the P' direction as cysteine protease inhibitors: effect on affinity and mechanism of inhibition.
Perlman N, Hazan M, Shokhen M, Albeck A., Bioorg Med Chem 16(19), 2008
PMID: 18789705
(2S,3S)-Oxirane-2,3-dicarboxylic acid: a privileged platform for probing human cysteine cathepsins.
Schaschke N., J Biotechnol 129(2), 2007
PMID: 17339064
Design, synthesis, and evaluation of in vivo potency and selectivity of epoxysuccinyl-based inhibitors of papain-family cysteine proteases.
Sadaghiani AM, Verhelst SH, Gocheva V, Hill K, Majerova E, Stinson S, Joyce JA, Bogyo M., Chem Biol 14(5), 2007
PMID: 17524981
Cathepsin B is essential for regeneration of scratch-wounded normal human epidermal keratinocytes.
Büth H, Luigi Buttigieg P, Ostafe R, Rehders M, Dannenmann SR, Schaschke N, Stark HJ, Boukamp P, Brix K., Eur J Cell Biol 86(11-12), 2007
PMID: 17651862
Chemical tools for activity-based proteomics.
Hagenstein MC, Sewald N., J Biotechnol 124(1), 2006
PMID: 16442651
The cathepsins contribute to life and death in the placenta.
Luft FC., J Mol Med (Berl) 84(4), 2006
PMID: 16557397
Quantitative evaluation of each catalytic subsite of cathepsin B for inhibitory activity based on inhibitory activity-binding mode relationship of epoxysuccinyl inhibitors by X-ray crystal structure analyses of complexes.
Watanabe D, Yamamoto A, Tomoo K, Matsumoto K, Murata M, Kitamura K, Ishida T., J Mol Biol 362(5), 2006
PMID: 16950396
Solid-phase synthesis of double-headed epoxysuccinyl activity-based probes for selective targeting of papain family cysteine proteases.
Verhelst SH, Bogyo M., Chembiochem 6(5), 2005
PMID: 15776409
Multiple cathepsin B isoforms in schistosomula of Trichobilharzia regenti: identification, characterisation and putative role in migration and nutrition.
Dvorák J, Delcroix M, Rossi A, Vopálenský V, Pospísek M, Sedinová M, Mikes L, Sajid M, Sali A, McKerrow JH, Horák P, Caffrey CR., Int J Parasitol 35(8), 2005
PMID: 15950230

42 References

Daten bereitgestellt von Europe PubMed Central.

On the size of the active site in proteases. I. Papain.
Schechter I, Berger A., Biochem. Biophys. Res. Commun. 27(2), 1967
PMID: 6035483
Design of potent and selective human cathepsin K inhibitors that span the active site.
Thompson SK, Halbert SM, Bossard MJ, Tomaszek TA, Levy MA, Zhao B, Smith WW, Abdel-Meguid SS, Janson CA, D'Alessio KJ, McQueney MS, Amegadzie BY, Hanning CR, DesJarlais RL, Briand J, Sarkar SK, Huddleston MJ, Ijames CF, Carr SA, Garnes KT, Shu A, Heys JR, Bradbeer J, Zembryki D, Lee-Rykaczewski L, James IE, Lark MW, Drake FH, Gowen M, Gleason JG, Veber DF., Proc. Natl. Acad. Sci. U.S.A. 94(26), 1997
PMID: 9405598
Novel epoxysuccinyl peptides. Selective inhibitors of cathepsin B, in vitro.
Murata M, Miyashita S, Yokoo C, Tamai M, Hanada K, Hatayama K, Towatari T, Nikawa T, Katunuma N., FEBS Lett. 280(2), 1991
PMID: 2013328
Binding mode of CA074, a specific irreversible inhibitor, to bovine cathepsin B as determined by X-ray crystal analysis of the complex.
Yamamoto A, Hara T, Tomoo K, Ishida T, Fujii T, Hata Y, Murata M, Kitamura K., J. Biochem. 121(5), 1997
PMID: 9192742
Crystal structure of human procathepsin X: a cysteine protease with the proregion covalently linked to the active site cysteine.
Sivaraman J, Nagler DK, Zhang R, Menard R, Cygler M., J. Mol. Biol. 295(4), 2000
PMID: 10656802
Increased expression of mature cathepsin B in aging rat liver.
Keppler D, Walter R, Perez C, Sierra F., Cell Tissue Res. 302(2), 2000
PMID: 11131129
E-64 analogues as inhibitors of cathepsin B. On the role of the absolute configuration of the epoxysuccinyl group.
Schaschke N, Assfalg-Machleidt I, Machleidt W, Turk D, Moroder L., Bioorg. Med. Chem. 5(9), 1997
PMID: 9354234
Protein folding and association: insights from the interfacial and thermodynamic properties of hydrocarbons.
Nicholls A, Sharp KA, Honig B., Proteins 11(4), 1991
PMID: 1758883
Surface cathepsin B protects cytotoxic lymphocytes from self-destruction after degranulation.
Balaji KN, Schaschke N, Machleidt W, Catalfamo M, Henkart PA., J. Exp. Med. 196(4), 2002
PMID: 12186841
Cathepsin B in osteoblasts.
Aisa MC, Beccari T, Costanzi E, Maggio D., Biochim. Biophys. Acta 1621(2), 2003
PMID: 12726991
Structure of rat procathepsin B: model for inhibition of cysteine protease activity by the proregion.
Cygler M, Sivaraman J, Grochulski P, Coulombe R, Storer AC, Mort JS., Structure 4(4), 1996
PMID: 8740363
Cathepsin B, Cathepsin H, and cathepsin L.
Barrett AJ, Kirschke H., Meth. Enzymol. 80 Pt C(), 1981
PMID: 7043200
Crystal structure of human osteoclast cathepsin K complex with E-64.
Zhao B, Janson CA, Amegadzie BY, D'Alessio K, Griffin C, Hanning CR, Jones C, Kurdyla J, McQueney M, Qiu X, Smith WW, Abdel-Meguid SS., Nat. Struct. Biol. 4(2), 1997
PMID: 9033588
Stimulation of angiogenesis through cathepsin B inactivation of the tissue inhibitors of matrix metalloproteinases.
Kostoulas G, Lang A, Nagase H, Baici A., FEBS Lett. 455(3), 1999
PMID: 10437790
Crystal structure of a papain-E-64 complex.
Varughese KI, Ahmed FR, Carey PR, Hasnain S, Huber CP, Storer AC., Biochemistry 28(3), 1989
PMID: 2713367
Beta-cyclodextrin/epoxysuccinyl peptide conjugates: a new drug targeting system for tumor cells.
Schaschke N, Assfalg-Machleidt I, Machleidt W, Lassleben T, Sommerhoff CP, Moroder L., Bioorg. Med. Chem. Lett. 10(7), 2000
PMID: 10762052
How to measure and predict the molar absorption coefficient of a protein.
Pace CN, Vajdos F, Fee L, Grimsley G, Gray T., Protein Sci. 4(11), 1995
PMID: 8563639
Significance of cathepsin B accumulation in synovial fluid of rheumatoid arthritis.
Hashimoto Y, Kakegawa H, Narita Y, Hachiya Y, Hayakawa T, Kos J, Turk V, Katunuma N., Biochem. Biophys. Res. Commun. 283(2), 2001
PMID: 11327703
Structure of human procathepsin L reveals the molecular basis of inhibition by the prosegment.
Coulombe R, Grochulski P, Sivaraman J, Menard R, Mort JS, Cygler M., EMBO J. 15(20), 1996
PMID: 8896443
The crystal structure of human procathepsin K.
LaLonde JM, Zhao B, Janson CA, D'Alessio KJ, McQueney MS, Orsini MJ, Debouck CM, Smith WW., Biochemistry 38(3), 1999
PMID: 9893980
Cathepsin B and its role(s) in cancer progression.
Podgorski I, Sloane BF., Biochem. Soc. Symp. (70), 2003
PMID: 14587299
Epoxysuccinyl peptide-derived affinity labels for cathepsin B.
Schaschke N, Assfalg-Machleidt I, Lassleben T, Sommerhoff CP, Moroder L, Machleidt W., FEBS Lett. 482(1-2), 2000
PMID: 11018529
Crystal structures of human procathepsin B at 3.2 and 3.3 Angstroms resolution reveal an interaction motif between a papain-like cysteine protease and its propeptide.
Turk D, Podobnik M, Kuhelj R, Dolinar M, Turk V., FEBS Lett. 384(3), 1996
PMID: 8617355
Cell-surface cathepsin B: understanding its functional significance.
Cavallo-Medved D, Sloane BF., Curr. Top. Dev. Biol. 54(), 2003
PMID: 12696754
Crystal structure of cathepsin B inhibited with CA030 at 2.0-A resolution: A basis for the design of specific epoxysuccinyl inhibitors.
Turk D, Podobnik M, Popovic T, Katunuma N, Bode W, Huber R, Turk V., Biochemistry 34(14), 1995
PMID: 7718586
Presence of cathepsin B in the human pancreatic secretory pathway and its role in trypsinogen activation during hereditary pancreatitis.
Kukor Z, Mayerle J, Kruger B, Toth M, Steed PM, Halangk W, Lerch MM, Sahin-Toth M., J. Biol. Chem. 277(24), 2002
PMID: 11932257
Bovine stefin C, a new member of the stefin family.
Turk B, Krizaj I, Kralj B, Dolenc I, Popovic T, Bieth JG, Turk V., J. Biol. Chem. 268(10), 1993
PMID: 8463267
Inhibition mechanism of cathepsin L-specific inhibitors based on the crystal structure of papain-CLIK148 complex.
Tsuge H, Nishimura T, Tada Y, Asao T, Turk D, Turk V, Katunuma N., Biochem. Biophys. Res. Commun. 266(2), 1999
PMID: 10600517
Crystal structure of an actinidin-E-64 complex.
Varughese KI, Su Y, Cromwell D, Hasnain S, Xuong NH., Biochemistry 31(22), 1992
PMID: 1606141
Crystal structure of papain-E64-c complex. Binding diversity of E64-c to papain S2 and S3 subsites.
Kim MJ, Yamamoto D, Matsumoto K, Inoue M, Ishida T, Mizuno H, Sumiya S, Kitamura K., Biochem. J. 287 ( Pt 3)(), 1992
PMID: 1445241
Structure based development of novel specific inhibitors for cathepsin L and cathepsin S in vitro and in vivo.
Katunuma N, Murata E, Kakegawa H, Matsui A, Tsuzuki H, Tsuge H, Turk D, Turk V, Fukushima M, Tada Y, Asao T., FEBS Lett. 458(1), 1999
PMID: 10518923
Raster3D: photorealistic molecular graphics.
Merritt EA, Bacon DJ., Meth. Enzymol. 277(), 1997
PMID: 18488322
The relative importance of cysteine peptidases in osteoarthritis.
Lang A, Horler D, Baici A., J. Rheumatol. 27(8), 2000
PMID: 10955340
Unraveling the role of proteases in cancer.
Koblinski JE, Ahram M, Sloane BF., Clin. Chim. Acta 291(2), 2000
PMID: 10675719
Crystallization and preliminary X-ray study of the cathepsin B complexed with CA074, a selective inhibitor.
Yamamoto A, Kaji T, Tomoo K, Ishida T, Inoue M, Murata M, Kitamura K., J. Mol. Biol. 227(3), 1992
PMID: 1404397
The refined 2.15 A X-ray crystal structure of human liver cathepsin B: the structural basis for its specificity.
Musil D, Zucic D, Turk D, Engh RA, Mayr I, Huber R, Popovic T, Turk V, Towatari T, Katunuma N., EMBO J. 10(9), 1991
PMID: 1868826
Apoptotic pathways: involvement of lysosomal proteases.
Turk B, Stoka V, Rozman-Pungercar J, Cirman T, Droga-Mazovec G, Oresic K, Turk V., Biol. Chem. 383(7-8), 2002
PMID: 12437086
Lysosomal cysteine proteases: more than scavengers.
Turk B, Turk D, Turk V., Biochim. Biophys. Acta 1477(1-2), 2000
PMID: 10708852
Substrate/propeptide-derived endo-epoxysuccinyl peptides as highly potent and selective cathepsin B inhibitors.
Schaschke N, Assfalg-Machleidt I, Machleidt W, Moroder L., FEBS Lett. 421(1), 1998
PMID: 9462845
Refined x-ray structure of papain.E-64-c complex at 2.1-A resolution.
Yamamoto D, Matsumoto K, Ohishi H, Ishida T, Inoue M, Kitamura K, Mizuno H., J. Biol. Chem. 266(22), 1991
PMID: 1860874
Rapid automated molecular replacement by evolutionary search.
Kissinger CR, Gehlhaar DK, Fogel DB., Acta Crystallogr. D Biol. Crystallogr. 55(Pt 2), 1999
PMID: 10089360
Novel epoxysuccinyl peptides. A selective inhibitor of cathepsin B, in vivo.
Towatari T, Nikawa T, Murata M, Yokoo C, Tamai M, Hanada K, Katunuma N., FEBS Lett. 280(2), 1991
PMID: 2013329
Export

Markieren/ Markierung löschen
Markierte Publikationen

Open Data PUB

Web of Science

Dieser Datensatz im Web of Science®
Quellen

PMID: 15084146
PubMed | Europe PMC

Suchen in

Google Scholar