Fluorescent substrates useful as high throughput screening tools for ADAM9

Combinatorial Chemistry and High Throughput Screening

Volumn 13, Issue 4, 2010, Pages 358-365

  Moss, Marcia L ^a   Rasmussen, Fred H ^a   Nudelman, Raphael ^b   Dempsey, Peter J ^c   Williams, Jason ^d  

^a BioZyme Inc   (United States)

^b TEVA PHARMACEUTICALS   (Israel)

^c UNIVERSITY OF MICHIGAN   (United States)

^d NATIONAL INSTITUTE OF ENVIRONMENTAL HEALTH SCIENCES   (United States)

Author keywords

ADAM10; ADAM12; ADAM17; ADAM8; ADAM9; CD23; Disintegrin; Fluorescent; FRET; GI254023; GM6001; Inhibitor; Metalloproteinase; Substrate; TACE; TGF alpha; TMI 1

Indexed keywords

6 CARBOXYFLUORESCEIN; ADAM 9 PROTEIN; ADAM PROTEIN; BETACELLULIN; CD23 ANTIGEN; FLUORESCENT DYE; IMMUNOGLOBULIN E; METALLOPROTEINASE INHIBITOR; PEPTIDE; PEPTIDE DERIVATIVE; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG;

ARTICLE; FLUORESCENCE RESONANCE ENERGY TRANSFER; HIGH THROUGHPUT SCREENING; IC 50; PRIORITY JOURNAL; TURNOVER TIME;

ADAM PROTEINS; BODY FLUIDS; FLUORESCENCE RESONANCE ENERGY TRANSFER; FLUORESCENT DYES; HYDROLYSIS; MEMBRANE PROTEINS; RECOMBINANT PROTEINS; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION;

EID: 77950809514     PISSN: 13862073     EISSN: None     Source Type: Journal    
DOI: 10.2174/138620710791054259     Document Type: Article

References (42)

1. Roghani, M.; Becherer, J.D.; Moss, M.L.; Atherton, R.E.; Erdjument-Bromage, H.; Arribas, J.; Blackburn, R.K.; Weskamp, G.; Tempst, P.; Blobel, C.P. Metalloprotease-disintegrin MDC9: intracellular maturation and catalytic activity. J. Biol. Chem., 1999, 274(6), 3531-3540. (Pubitemid 29077194)
2. Wolfsberg, T.G.; Straight, P.D.; Gerena, R.L.; Huovila, A.P.; Primakoff, P.; Myles, D.G.; White, J.M. ADAM, a widely distributed and developmentally regulated gene family encoding membrane proteins with a disintegrin and metalloprotease domain. Dev. Biol., 1995, 169(1), 378-383.
3. Blobel, C.P. ADAMs: key components in EGFR signalling and development. Nat. Rev. Mol. Cell Biol., 2005, 6(1), 32-43.
4. Moss, M.L.; Bartsch J.W. Therapeutic benefits from targeting of ADAM family members. Biochemistry, 2004, 43(23), 7227-7235.
5. Murphy, G. The ADAMs: signalling scissors in the tumour microenvironment. Nat. Rev. Cancer, 2008, 8(12), 929-941.
6. Moss, M.L.; Sklair-Tavron, L.; Nudelman, R. Drug insight: tumor necrosis factor-converting enzyme as a pharmaceutical target for rheumatoid arthritis. Nat. Clin. Pract. Rheumatol., 2008, 4(6), 300-309. (Pubitemid 351791441)
7. Weskamp, G.; Ford, J.W.; Sturgill, J.; Martin, S.; Docherty, A.J.; Swendeman, S.; Broadway, N.; Hartmann, D.; Saftig, P.; Umland, S.; Sehara-Fujisawa, A.; Black, R.A.; Ludwig, A.; Becherer, J.D.; Conrad, D.H.; Blobel, C.P. ADAM10 is a principal 'sheddase' of the low-affinity immunoglobulin E receptor CD23. Nat. Immunol., 2006, 7(12), 1293-1298. (Pubitemid 46111250)
8. Lemieux, G.A.; Blumenkron, F.; Yeung, N.; Zhou, P.; Williams, J.; Grammer, A.C.; Petrovich, R.; Lipsky, P.E.; Moss, M.L.; Werb, Z. The low affinity IgE receptor (CD23) is cleaved by the metalloproteinase ADAM10. J. Biol. Chem., 2007, 282(20), 14836-14844. (Pubitemid 47093331)
9. Fourie, A.M.; Coles, F.; Moreno, V.; Karlsson, L. Catalytic activity of ADAM8, ADAM15, and MDC-L (ADAM28) on synthetic peptide substrates and in ectodomain cleavage of CD23. J. Biol. Chem., 2003, 278(33), 30469-30477. (Pubitemid 36994550)
10. Ludwig, A.; Hundhausen, C.; Lambert, M.H.; Broadway, N.; Andrews, R.C.; Bickett, D.M.; Leesnitzer, M.A.; Becherer, J.D. Metalloproteinase inhibitors for the disintegrin-like metallopro-teinases ADAM10 and ADAM17 that differentially block constitutive and phorbol ester-inducible shedding of cell surface mole-cules. Comb. Chem. High Throughput Screen., 2005, 8(2), 161-171. (Pubitemid 40388743)
11. Asakura, M.; Kitakaze, M.; Takashima, S.; Liao, Y.; Ishikura, F.; Yoshinaka, T.; Ohmoto, H.; Node, K.; Yoshino, K.; Ishiguro, H.; Asanuma, H.; Sanada, S.; Matsumura, Y.; Takeda, H.; Beppu, S.; Tada, M.; Hori, M.; Higashiyama, S. Cardiac hypertrophy is inhibited by antagonism of ADAM12 processing of HB-EGF: metalloproteinase inhibitors as a new therapy. Nat. Med., 2002, 8(1), 35-40. (Pubitemid 34101726)
12. Togashi, N.; Ura, N.; Higashiura, K.; Murakami, H.; Shimamoto, K. Effect of TNF-alpha-converting enzyme inhibitor on insulin resistance in fructose-fed rats. Hypertension, 2002, 39(2 Pt 2), 578-580. (Pubitemid 34165186)
13. Gelling, R.W.; Yan, W.; Al-Noori, S.; Pardini, A.; Morton, G.J.; Ogimoto, K.; Schwartz, M.W.; Dempsey, P.J. Deficiency of TNFalpha converting enzyme (TACE/ADAM17) causes a lean, hypermetabolic phenotype in mice. Endocrinology, 2008, 149(12), 6053-6064.
14. Serino, M.; Menghini, R.; Fiorentino, L.; Amoruso, R.; Mauriello, A.; Lauro, D.; Sbraccia, P.; Hribal, M. L.; Lauro, R.; Federici, M. Mice heterozygous for tumor necrosis factor-alpha converting enzyme are protected from obesity-induced insulin resistance and diabetes. Diabetes, 2007, 56(10), 2541-2546. (Pubitemid 47523261)
15. Sunnarborg, S.W.; Hinkle, C.L.; Stevenson, M.; Russell, W.E.; Raska, C.S.; Peschon, J.J.; Castner, B.J.; Gerhart, M.J.; Paxton, R.J.; Black, R.A.; Lee, D.C. Tumor necrosis factor-alpha converting enzyme (TACE) regulates epidermal growth factor receptor ligand availability. J. Biol. Chem., 2002, 277(15), 12838-12845. (Pubitemid 34952648)
16. Peschon, J.J.; Slack, J.L.; Reddy, P.; Stocking, K.L.; Sunnarborg, S.W.; Lee, D.C.; Russell, W.E.; Castner, B.J.; Johnson, R.S.; Fitzner, J.N.; Boyce, R.W.; Nelson, N.; Kozlosky, C.J.; Wolfson, M.F.; Rauch, C.T.; Cerretti, D.P.; Paxton, R.J.; March, C.J.; Black, R.A. An essential role for ectodomain shedding in mammalian development. Science, 1998, 282(5392), 1281-1284. (Pubitemid 28524483)
17. Sahin, U.; Weskamp, G.; Kelly, K.; Zhou, H.M.; Higashiyama, S.; Peschon, J.; Hartmann, D.; Saftig, P.; Blobel, C.P. Distinct roles for ADAM10 and ADAM17 in ectodomain shedding of six EGFR ligands. J. Cell Biol., 2004, 164(5), 769-779. (Pubitemid 38282960)
18. Sanderson, M.P.; Erickson, S.N.; Gough, P.J.; Garton, K.J.; Wille, P.T.; Raines, E.W.; Dunbar, A.J.; Dempsey, P. J. ADAM10 mediates ectodomain shedding of the betacellulin precursor activated by p-aminophenylmercuric acetate and extracellular calcium influx. J. Biol. Chem., 2005, 280(3), 1826-1837.
19. Hinkle, C.L.; Sunnarborg, S.W.; Loiselle, D.; Parker, C.E.; Stevenson, M.; Russell, W.E.; Lee, D.C. Selective roles for tumor necrosis factor alpha-converting enzyme/ADAM17 in the shedding of the epidermal growth factor receptor ligand family: the juxtamembrane stalk determines cleavage efficiency. J. Biol. Chem., 2004, 279(23), 24179-24188. (Pubitemid 38725278)
20. Yan, Y.; Shirakabe, K.; Werb, Z. The metalloprotease Kuzbanian (ADAM10) mediates the transactivation of EGF receptor by G protein-coupled receptors. J. Cell Biol., 2002, 158(2), 221-226.
21. Peduto, L.; Reuter, V.E.; Shaffer, D.R.; Scher, H.I.; Blobel, C.P. Critical function for ADAM9 in mouse prostate cancer. Cancer Res., 2005, 65(20), 9312-9319. (Pubitemid 41507998)
22. Gould, H.J.; Sutton, B.J. IgE in allergy and asthma today. Nat. Rev. Immunol., 2008, 8(3), 205-217.
23. Hartmann, D.; de Strooper, B.; Serneels, L.; Craessaerts, K.; Herreman, A.; Annaert, W.; Umans, L.; Lubke, T.; Lena Illert, A.; von Figura, K.; Saftig, P.The disintegrin/metalloprotease ADAM 10 is essential for Notch signalling but not for alpha-secretase activity in fibroblasts. Hum Mol. Genet., 2002, 11(21), 2615-2624. (Pubitemid 35174691)
24. Weskamp, G.; Cai, H.; Brodie, T.A.; Higashyama, S.; Manova, K.; Ludwig, T.; Blobel, C.P. Mice lacking the metalloprotease-disintegrin MDC9 (ADAM9) have no evident major abnormalities during development or adult life. Mol. Cell Biol., 2002, 22(5), 1537-1544. (Pubitemid 34150789)
25. Garcia-Echeverria C.; Rich, D.H. New intramolecularly quenched fluorogenic peptide substrates for the study of the kinetic specificity of papain. FEBS Lett., 1992, 297(1-2), 100-102.
26. Matayoshi, E.D.; Wang, G.T.; Krafft, G.A.; Erickson, J. Novel fluorogenic substrates for assaying retroviral proteases by resonance energy transfer. Science, 1990, 247(4945), 954-958. (Pubitemid 20081658)
27. Beekman, B.; Drijfhout, J.W.; Ronday, H.K.; TeKoppele, J.M. Fluorogenic MMP activity assay for plasma including MMPs complexed to alpha 2-macroglobulin. Ann. NY Acad. Sci., 1999, 878, 150-158. (Pubitemid 29353567)
28. Chersi, A.; Ferracuti, S.; Falasca, G.; Butler, R.H.; Fruci, D. Assembly and selective "in synthesis" labeling of quenched fluorogenic protease substrates. Anal. Biochem., 2006, 357(2), 194-199. (Pubitemid 44415698)
29. Levin, J.I.; Chen, J.M.; Laakso, L.M.; Du, M.; Du, X.; Venkatesan, A.M.; Sandanayaka, V.; Zask, A.; Xu, J.; Xu, W.; Zhang, Y.; Skotnicki, J.S. Acetylenic TACE inhibitors. Part 2: SAR of six-membered cyclic sulfonamide hydroxamates. Bioorg. Med. Chem. Lett., 2005, 15(19), 4345-4349. (Pubitemid 41188016)
30. Steward, W.P.; Thomas, A.L. Marimastat: the clinical development of a matrix metalloproteinase inhibitor. Expert Opin. Investig. Drugs, 2000, 9(12), 2913-2922.
31. Williams, J.W.; Morrison, J.F. The kinetics of reversible tight-binding inhibition. Methods Enzymol., 1979, 63, 437-467.
32. Moss, M.L.; Rasmussen, F.H. Fluorescent substrates for the proteinases ADAM17, ADAM10, ADAM8, and ADAM12 useful for high throughput inhibitor screening. Anal. Biochem., 2007, 366(2), 144-148.
33. Liu, P.C.; Liu, X.; Li, Y.; Covington, M.; Wynn, R.; Huber, R.; Hillman, M.; Yang, G.; Ellis, D.; Marando, C.; Katiyar, K.; Bradley, J.; Abremski, K.; Stow, M.; Rupar, M.; Zhuo, J.; Li, Y.L.; Lin, Q.; Burns, D.; Xu, M.; Zhang, C.; Qian, D.Q.; He, C.; Sharief, V.; Weng, L.; Agrios, C.; Shi, E.; Metcalf, B.; Newton, R.; Friedman, S.; Yao, W., Scherle, P.; Hollis, G.; Burn, T.C. Identification of ADAM10 as a major source of HER2 ectodomain sheddase activity in HER2 overexpressing breast cancer cells. Cancer Biol. Ther., 2006, 5(6), 657-664. (Pubitemid 44024721)
34. Zhang, Y.; Hegen, M.; Xu, J.; Keith, J.C.; Jr.; Jin, G.; Du, X.; Cummons, T.; Sheppard, B.J.; Sun, L.; Zhu, Y.; Rao, V.R.; Wang, Q.; Xu, W.; Cowling, R.; Nickerson-Nutter, C. L.; Gibbons, J.; Skotnicki, J.; Lin, L.L.; Levin, J. Identification and characterization of 4-[[4-(2-butynyloxy)phenyl]sulfonyl]-N- hydroxy-2,2-dimethyl-(3S)thiomorpho linecarboxamide (TMI-1), a novel dual tumor necrosis factor-alpha-converting enzyme/matrix metalloprotease inhibitor for the treatment of rheumatoid arthritis. J Pharmacol. Exp. Ther., 2004, 309(1), 348-355. (Pubitemid 38393148)
35. Grobelny D.; Poncz L.; Galardy R.E. Inhibition of human skin fibroblast collagenase, thermolysin, and Pseudomonas aeruginosa elastase by peptide hydroxamic acids. Biochemistry, 1992, 31(31), 7152-7154.
36. Gijbels K.; Galardy R.E.; Steinman L. Reversal of experimental autoimmune encephalomyelitis with a hydroxamate inhibitor of matrix metalloproteases. J. Clin. Invest., 1994, 94(6), 2177-2182. (Pubitemid 24379586)
37. Rasmussen, F.H.; Yeung, N.; Kiefer, L.; Murphy, G.; Lopez-Otin, C.; Vitek, M.P.; Moss, M.L. Use of a multiple-enzyme/multiple-reagent assay system to quantify activity levels in samples containing mixtures of matrix metalloproteinases. Biochemistry. 2004, 43(11), 2987-2995. (Pubitemid 38352249)
38. Pories, S.E.; Zurakowski, D.; Roy, R.; Lamb, C.C.; Raza, S.; Exarhopoulos, A.; Scheib, R.G.; Schumer, S.; Lenahan, C.; Borges, V.; Louis, G.W.; Anand, A.; Isakovich, N.; Hirshfield-Bartek, J.; Wewer, U.; Lotz, M.M.; Moses, M.A. Urinary metalloproteinases: noninvasive biomarkers for breast cancer risk assessment. Cancer Epidemiol. Biomarkers Prev., 2008, 5, 1034-1042.
39. Frohlich, C.; Albrechtsen, R.; Dyrskjot, L.; Rudkjaer, L.; Orntoft, T.F.; Wewer, U.M. Molecular profiling of ADAM12 in human bladder cancer. Clin. Cancer Res., 2006, 12(24), 7359-7368. (Pubitemid 46095409)
40. Schlomann, U.; Wildeboer, D.; Webster, A.; Antropova, O.; Zeuschner, D.; Knight, C.G.; Docherty, A.J.; Lambert, M.; Skelton, L.; Jockusch, H.; Bartsch, J.W. The metalloprotease disintegrin ADAM8. Processing by autocatalysis is required for proteolytic activity and cell adhesion. J. Biol. Chem., 2002, 277(50), 48210-48219. (Pubitemid 35470772)
41. Mazzocca, A.; Coppari, R.; De Franco, R.; Cho, J.Y.; Libermann, T.A.; Pinzani, M.; Toker, A. A secreted form of ADAM9 promotes carcinoma invasion through tumor-stromal interactions. Cancer Res., 2005, 65(11), 4728-4738. (Pubitemid 40740809)
42. Tousseyn, T.; Thathiah, A.; Jorissen, E.; Raemaekers, T.; Konietzko, U.; Reiss, K.; Maes, E.; Snellinx, A.; Serneels, L.; Nyabi, O.; Annaert, W.; Saftig, P.; Hartmann, D.; De Strooper, B. ADAM10, the rate-limiting protease of regulated intramembrane proteolysis of Notch and other proteins, is processed by ADAMS-9, ADAMS-15, and the gamma-secretase. J. Biol. Chem., 2009, 284(17), 11738-11747.