Divergent synthesis of multifunctional molecular probes to elucidate the enzyme specificity of dipeptidic γ-secretase inhibitors

ACS Chemical Biology

Volumn 2, Issue 6, 2007, Pages 408-418

  Fuwa, Haruhiko ^a   Takahashi, Yasuko ^d   Konno, Yu ^a   Watanabe, Naoto ^d   Miyashita, Hiroyuki ^d   Sasaki, Makoto ^a   Natsugaril, Hideaki ^c,d   Kan, Toshiyuki ^b,d   Fukuyama, Tohru ^d   Tomita, Taisuke ^d   Iwatsubo, Takeshi ^d  

^a TOHOKU UNIVERSITY   (Japan)

^b UNIVERSITY OF SHIZUOKA   (Japan)

^c TEIKYO UNIVERSITY   (Japan)

^d UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 CHLORO 3 (3,4 DICHLOROPHENYL) 1 ISOPROPYL 4 METHYLIMIDAZOLIUM CHLORIDE; ALKYNE; AZIDE; BIOTIN; CAPROLACTAM DERIVATIVE; COPPER ION; GAMMA SECRETASE; GAMMA SECRETASE INHIBITOR; LY 411575; PRESENILIN 1; PROTEINASE; SIGNAL PEPTIDASE; UNCLASSIFIED DRUG; PROTEINASE INHIBITOR; SECRETASE;

AMINO TERMINAL SEQUENCE; ANIMAL CELL; ARTICLE; CATALYSIS; CONTROLLED STUDY; DRUG POTENCY; DRUG PROTEIN BINDING; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG TARGETING; ENZYME INHIBITOR COMPLEX; ENZYME INHIBITOR INTERACTION; ENZYME SPECIFICITY; HELA CELL; HUMAN; HUMAN CELL; MOLECULAR PROBE; MOUSE; NONHUMAN; PHOTOACTIVATION; PHOTOAFFINITY LABELING; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS; ANIMAL; BIOSYNTHESIS; CHEMISTRY; COMPARATIVE STUDY; DRUG ANTAGONISM; DRUG EFFECT; METABOLISM; PHYSIOLOGY;

AMYLOID PRECURSOR PROTEIN SECRETASES; ANIMALS; HELA CELLS; HUMANS; MOLECULAR PROBES; PRESENILIN-1; PROTEASE INHIBITORS; SUBSTRATE SPECIFICITY;

EID: 34547597126     PISSN: 15548929     EISSN: None     Source Type: Journal    
DOI: 10.1021/cb700073y     Document Type: Article

References (50)

1. Tomita, T., and Iwatsubo, T. (2006) γ-Secretase as a therapeutic target for treatment of Alzheimer's disease, Curr. Pharm. Des. 12, 661-670.
2. Roy, M., Pear, W.S., and Aster, J.C. (2007) The multifaceted role of notch in cancer, Curr. Opin. Genet. Dev. 17, 52-59.
3. Weihofen, A., Binns, K., Lemberg, M.K., Ashman, K., and Martoglio, B. (2002) Identification of signal peptide peptidase, a presenilin-type aspartic protease, Science 296, 2215-2218.
4. Grigorenko, A. P., Moliaka, Y. K., Soto, M. C., Mello, C. C., and Rogaev, E. I. (2004) The Caenorhabditis elegans IMPAS gene, imp-2, is essential for development and is functionally distinct from related presenilins, Proc. Natl. Acad. Sci. U.S.A. 101, 14955-14960.
5. Casso, D. J., Tanda, S., Biehs, B., Martoglio, B., and Komberg, T. B. (2005) Drosophila signal peptide peptidase is an essential protease for larval development, Genetic 170, 139-148.
6. Krawitz, P., Haffner, C., Fluhrer, R., Steiner, H., Schmid, B., and Haass, C. (2005) Differential localization and identification of a critical aspartate suggest non-redundant proteolytic functions of the presenilin homologues SPPL2b and SPPL3, J. Biol. Chem. 280, 39515-39523.
7. Friedmann, E., Hauben, E., Maylandt, K., Schleeger, S., Vreugde, S., Lichtenthaler, S. F., Kuhn, P. H., Stauffer, D., Rovelli, G., and Martoglio, B. (2006) SPPL2a and SPPL2b promote intramembrane proteolysis of TNFα in activated dendritic cells to trigger IL-12 production, Nat. Cell Biol. 8, 843-848.
8. McLauchlan, J., Lemberg, M. K., Hope, G., and Martoglio, B. (2002) Intramembrane proteolysis promotes trafficking of hepatitis C virus core protein to lipid droplets, EMBO J. 21, 3980-3988.
9. Weihofen, A., Lemberg, M. K., Friedmann, E., Rueeger, H., Schmitz, A., Paganetti, P., Rovelli, G., and Martoglio, B. (2003) Targeting presenilin type aspartic protease signal peptide peptidase with γ-secretase inhibitors, J. Biol. Chem. 278, 16528-16533.
10. Nyborg, A. C., Jansen, K., Ladd, T. B., Fauq, A., and Golde, T. E. (2004) A signal peptide peptidase (SPP) reporter activity assay based on the cleavage of type II membrane protein substrates provides further evidence for an inverted orientation of the SPP active site relative to presenilin, J. Biol. Chem. 279, 43148-43156.
11. Dev, K. K., Chatterjee, S., Osinde, M., Stauffer, D., Morgan, H., Kobialko, M., Dengler, U., Rueeger, H., Martoglio, B., and Rovelli, G. (2006) Signal peptide peptidase dependent cleavage of type II transmembrane substrates releases intracellular and extracellular signals, Eur J Pharmacol. 540, 10-17.
12. Seiffert, D., Bradley, J. D., Rominger, C. M., Rominger, D. H., Yang. F., Meredith, J. E., Jr., Wang, Q., Roach, A. H., Thompson, L. A., Spitz, S. M., Higaki, J. N., Prakash, S. R., Combs, A. P., Copeland, R. A., Arneric, S. P., Hartig, P. R., Robertson, D. W., Cordell, B., Stern, A. M., Olson, R. E., and Zaczek, R. (2000) Presenilin-1 and -2 are molecular targets for γ-secretase inhibitors, J. Biol. Chem. 275, 34086-34091.
13. Morohashi, Y., Kan, T., Tominari, Y., Fuwa, H., Okamura, Y., Watanabe, N., Sato, C., Natsugari, H., Fukuyama, T., Iwatsubo, T., and Tomita, T. (2006) Carboxyl-terminal fragment of presenilin is the molecular target of γ-secretase-specific dipeptidic inhibitor DAPT (N- i N-(3,5-difluorophenacetyl)-L-alanyl]-S-phenylglycine t-butyl ester), J. Biol. Chem. 281, 14670-14676.
14. Tian, G., Sobotka-Briner, C. D., Zysk, J., Liu, X., Birr, C., Sylvester, M. A., Edwards, P. D., Scott, C. D., and Greenberg, B. D. (2002) Linear non-competitive inhibition of solubilized human γ-secretase by pepstatin A methylester, L685458, sulfonamides, and benzodiazepines. J. Biol. Chem. 277, 31499-31505.
15. Tian, G., Ghanekar, S. V., Aharony, D., Shenvi, A. B., Jacobs, R. T., Liu, X., and Greenberg, B. D. (2003) The mechanism of γ-secretase: multiple inhibitor binding sites for transition state analogs and small molecule inhibitors, J. Biol. Chem. 278, 28968-28975.
16. Clarke, E. E., Churcher, I., Ellis, S., Wrigley, J. D., Lewis, H. D., Harrison, T., Shearman, M. S., and Beher, D. (2006) Intra- or intercomplex binding to the γ-secretase enzyme a model to differentiate inhibitor classes, J. Biol. Chem. 281, 31279-31289.
17. Hofmann, K., and Kiso, Y. (1976) An approach to the targeted attachment of peptides and proteins to solid supports, Proc. Natl. Acad. Sci. U.S.A. 73, 3516-3518.
18. Dormán, G., and Prestwich, G. D. (1994) Benzophenone photophores in biochemistry, Biochemistry 33, 5661-5673.
19. Kotzyba-Hibert, F., Kapfer, I., and Goeldner, M. (1995) Recent trends in photoaffinity-labeling, Angew. Chem., Int. Ed. Engl. 34, 1296-1312.
20. Dormán, G., and Prestwich, G. D. (2000) Using photolabile ligands in drug discovery and development, Trends Biotechnol. 18, 64-77.
21. Kan, T., Tominari, Y., Morohashi, Y., Natsugari, H., Tomita, T., Iwatsubo, T., and Fukuyama, T. (2003) Solid-phase synthesis of photoaffinity probes. highly efficient incorporation of biotin-tag and cross-linking groups, Chem. Commun. 17, 2244-2245.
22. Kan, T., Tominari, Y., Rikimaru, K., Morohashi, Y., Natsugari, H., Tomita, T., Iwatsubo, T., and Fukuyama, T. (2004) Parallel synthesis of DAPT derivatives and their γ-secretase-inhibitory acitivity, Bioorg. Med. Chem. Lett. 14, 1983-1985.
23. Rostovtsev, V. V., Green, L. G., Fokin, V. V., and Sharpless. K. B. (2002) A stepwise Huisgen cycloaddition process: copper(l)-catalyzed regioselective "ligation" of azides and terminal alkynes, Angew. Chem., Int. Ed. 41, 2596-2599.
24. Tornøe, C. W., Christensen, C., and Meldal, M. (2002) Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific Cu(l)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides, J. Org. Chem. 67, 3057-3064.
25. Hatanaka, Y., Kempin, U., and Park, J.-J. (2000) One-step synthesis of biotinyl photoprobes from unprotected carbohydrates, J. Org. Chem. 65, 5639-5643.
26. Wang, J., Uttamchandani, M., Li, J., Hu, M., and Yao, S. Q. (2006) "Click" synthesis of small molecule probes for activity-based finger-printing of matrix metalloproteases, Chem. Commun. 3783-3785.
27. Inverarity, I. A., and Hulme, A. N. (2007) Marked small molecule libraries: a truncated approach to molecular probe design, Org. Biomol. Chem. 5, 636-643.
28. Hashimoto, M., Hatanaka, Y., Yang, J., Dhesi, J., and Holman, G. D. (2001) Synthesis of biotinylated bis(D-glucose) derivatives for glucose transporter photoaffinity labeling, Carbohydrate Res. 331, 119-127.
29. Hashimoto, M., Kanaoka, Y., and Hatanaka, Y. (1997) A versatile approach for functionalization of 3-aryl-3-trifluoromethyldiazirine photophor, Heterocycles 46, 119-122.
30. Hatanaka, Y., Hashimoto, M., Kurihara, H., Nakayama, H., and Kanaoka, Y. (1994) Novel family of aromatic diazirines for photoaffinity-labeling, J. Org. Chem. 59, 383-387.
31. Egbertson, M. S., Chang, C. T.-C., Duggan, M. E., Gould, R. J., Halczenko, W., Hartman, G. D., Laswell, W. L., Lynch, J. J., Lynch, R. J., Manno, P. D., Naylor, A. M., Prugh, J. D., Ramjit, D. R., Sitko, G. R., Smith, R. S., Turchi, L. M., and Zhang, G. (1994) Non-peptide fibrinogen receptor antagonists. 2. optimization of a tyrosine template as a mimic for Arg-Gly-Asp, J. Med. Chem. 37, 2537-2551.
32. Hatanaka, Y., Hashimoto, M., and Kanaoka, Y. (1994) A novel biotinylated heterobifunctional cross-linking reagent bearing an aromatic diazirine, Bioorg. Med. Chem. 2, 1367-1373.
33. Fang, K., Hashimoto, M., Jockusch, S., Turro, N. J., and Nakanishi, K. (1998) A bifunctional photoaffinity probe for ligand/receptor interaction studies, J. Am. Chem. Soc. 120, 8543-8544.
34. Li, H. Y., Liu, Y., Fang, K., and Nakanishi, K. (1999) A simple photoaffinity-labeling protocol, Chem. Commun. 365-366.
35. Hashimoto, M., Okamoto, S., Nabeta, K., and Hatanaka, Y. (2004) Enzyme cleavable and biotinylated photoaffinity ligand with diazirine, Bioorg. Med. Chem. Lett. 14, 2447-2450.
36. Park, J.-J., Sadakane, Y., Masuda, K., Tomohiro, T., Nakano, T., and Hatanaka, Y. (2005) Synthesis of diazirinyl photoprobe carrying a novel cleavable biotin, ChemBioChem 6, 814-818.
37. Butcher, J. W., Liverton, N. J., Selnick, H. G., Elliot, J. M., Smith, G. R., Tebben, A. J., Pribush, D. A., Wai, J. S., and Claremon, D. A. (1996) Preparation of 3-amino-1,4-benzodiazepin-2-ones via direct azidation with trisyl azide, Tetrahedron Lett. 37, 6685-6688.
38. Fuwa, H., Okamura, Y., Morohashi, Y., Tomita, T., Iwatsubo, T., Kan, T., Fukuyama, T., and Natsugari, H. (2004) Highly efficient synthesis of medium-sized ring lactams via Staudinger-Aza-Wittig reaction of ω-azido pentafluorophenyl ester: synthesis and biological evaluation of LY411575 analogues, Tetrahedron Lett. 45, 2323-2326.
39. Wang, Q., Chan, T. R., Hilgraf, R., Fokin, V. V., Sharpless, K. B., and Finn, M. G. (2003) Bioconjugation by copper(l)-catalyzed azide-alkyne [3 + 2] cycloaddition, J. Am. Chem. Soc. 125, 3192-3193.
40. Takahashi, Y., Hayashi, I., Tominari, Y., Rikimaru, K., Morohashi, Y., Kan, T., Natsugari, H., Fukuyama, T., Tomita, T., and Iwatsubo, T. (2003) Sulindac sulfide is a noncompetitive γ-secretase inhibitor that preferentially reduces Aβ42 generation, J. Biol. Chem. 278, 18664-18670.
41. Zhao, G., Tan, J., Mao, G., Cui, M. Z., and Xu, X. (2007) The same γ-secretase accounts for the multiple intramembrane cleavages of APP, J. Neurochem. 100, 1234-1246.
42. Nyborg, A. C., Kornilova, A. Y., Jansen, K., Ladd, T. B., Wolfe, M. S., and Golde, T. E. (2004) Signal peptide peptidase forms a homodimer that is labeled by an active site-directed γ-secretase inhibitor, J. Biol. Chem. 279, 15153-15160.
43. Nyborg, A. C., Ladd, T. B., Jansen, K., Kukar, T., and Golde. T. E. (2006) Intramembrane proteolytic cleavage by human signal peptide peptidase like 3 and malaria signal peptide peptidase, FASEB J. 20, 1671-1679.
44. Fujii, T., Manabe, Y., Sugimoto, T., and Ueda, M. (2005) Detection of 210 kDa receptor protein for a leaf-movement factor by using novel photoaffinity probes, Tetrahedron 61, 7874-7893.
45. Kan, T., Kita, Y., Morohashi, Y., Tominari, Y., Hosoda, S., Tomita, T., Natsugari, H., Iwatsubo, T., and Fukuyama, T. (2007) Convenient synthesis of photoaffinity probes and evaluation of their abilities, Org. Lett. 9, 2055-2058.
46. Takahashi, Y., Fuwa, H., Kaneko, A., Sasaki, M., Yokoshima, S., Koizumi, H., Takebe, T., Kan, T., Iwatsubo, T., Tomita, T., Natsugari, H., and Fukuyama, T. (2006) Novel γ-secretase inhibitors discovered by library screening of in-house synthetic natural product intermediates, Bioorg. Med. Chem. Lett. 16, 3813-3816.
47. Fuwa, H., Hiromoto, K., Takahashi, Y., Yokoshima, S., Kan, T., Fukuyama, T., Iwatsubo, T., Tomita, T., and Natsugari, H. (2006) Synthesis of biotinylated photoaffinity probes based on arylsulfonamide γ-secretase inhibitors, Bioorg. Med. Chem. Lett. 16, 4184-4189.
48. Tomita, T., Takikawa, R., Koyama, A., Morohashi, Y., Takasugi, N., Saido, T. C., Maruyama, K., and Iwatsubo, T. (1999) C Terminus of presenilin is required for overproduction of amyloidogenic Aβ42 through stabilization and endoproteolysis of presenilin, J. Neurosci. 19, 10627-10634.
49. Hayashi, I., Urano, Y., Fukuda, R., Isoo, N., Kodama, T., Hamakubo, T., Tomita, T., and Iwatsubo, T. (2004) Selective reconstitution and recovery of functional γ-secretase complex on budded baculovirus particles, J. Biol. Chem. 279, 38040-38046.
50. Ogura, T., Mio, K., Hayashi, I., Miyashita, H., Fukuda, R., Kopan, R., Kodama, T., Hamakubo, T., Iwatsubo, T., Tomita, T., and Sato, C. (2006) Three-dimensional structure of the γ-secretase complex, Biochem. Biophys. Res. Commun. 343, 525-534.