Synthesis and screening of a library of Re/Tc-based amyloid probes derived from β-breaker peptides

Bioconjugate Chemistry

Volumn 19, Issue 5, 2008, Pages 1087-1094

  Stephenson, Karin A ^a   Reid, Leslie C ^a   Zubieta, Jon ^b   Babich, John W ^c   Kung, Mei Ping ^d   Kung, Hank F ^d   Valliant, John F ^a  

^a MCMASTER UNIVERSITY   (Canada)

^b SYRACUSE UNIVERSITY   (United States)

^c A Subsidiary of Lantheus Holdings   (United States)

^d UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; BIOSYNTHESIS; GLYCOPROTEINS; PROBES; RHENIUM COMPOUNDS;

AMINO ACID DERIVATIVES; AMINO-ACIDS; AMYLOID PLAQUES; CARRIER PROTEINS; D-AMINO ACIDS; DEVELOPMENT AND APPLICATIONS; METALLOPEPTIDES; MONOMERICS; RE COMPLEX; SYNTHESISED;

PEPTIDES;

AMYLOID; AMYLOID BETA PROTEIN; BIOTIN; COLLAGEN FIBRIL; CYSTEINE; HISTIDINE; PEPTIDE; PEPTIDE LIBRARY; QUINOLINE DERIVATIVE; QUINOLONE; RHENIUM COMPLEX; TECHNETIUM 99M; THIOFLAVINE;

ARTICLE; CHEMICAL STRUCTURE; CONJUGATION; CONTROLLED STUDY; FIBER; NONHUMAN; PEPTIDE SYNTHESIS; PROTEIN STABILITY;

EID: 44349184299     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc800001g     Document Type: Article

References (34)

1. Bachurin, S. O. (2002) Medicinal chemistry approaches for the treatment and prevention of Alzheimer's disease. Med. Res. Rev. 23, 48-88.
2. Mattson, M. P. (2004) Pathways towards and away from Alzheimer's disease. Nature 430, 631-639.
3. 111In chelation, conjugation to poly(ethylene glycol)-biotin linkers, and autora-diography with Alzheimer's disease brain sections. Bioconjugate Chem. 11, 380-386.
4. Soto, C. (1999) Plaque busters: strategies to inhibit amyloid formation in Alzheimer's disease. Mol. Med. Today 5, 343-350.
5. Geula, C., Wu, C. K., Saroff, D., Lorenzo, A., Yuan, M., and Yankner, B. A. (1998) Aging renders the brain vulnerable to amyloid β-protein neurotoxicity. Nat. Med. 4, 827-831.
6. Hardy, J., and Selkoe, D. J. (2002) The amyloid hypothesis of Alzheimer's disease: progress and problems on the road to therapeutics. Science 297, 353-356.
7. Pitschke, M., Prior, R., Haupt, M., and Riesner, D. (1998) Detection of single amyloid β-protein aggregates in the cerebrospinal fluid of Alzheimer's patients by fluorescence correlation spectroscopy. Nat. Med. 4, 832-834.
8. Verhoeff, N. P., Wilson, A. A., Takeshita, S., Trop, L., Hussey, D., Singh, K., Kung, H. F., Kung, M.-P., and Houle, S. (2004) In vivo imaging of Alzheimer disease β-amyloid with [11C]SB-13 PET. Am. J. Geriatr. Psychiatry 12, 584-595.
9. Klunk, W. E., Engler, H., Nordberg, A., Wang, Y., Blomqvist, G., Holt, D. P., Bergstrom, M., Savitcheva, I., Huang, G.-f., Estrada, S., Ausen, B., Debnath, M. L., Barletta, J., Price, J. C., Sandell, J., Lopresti, B. J., Wall, A., Koivisto, P., Antoni, G., Mathis, C. A., and Langstrom, B. (2004) Imaging brain amyloid in Alzheimer's disease with Pittsburgh Compound-B. Ann. Neurol. 55, 306-319.
10. Qu, W., Kung, M.-P., Hou, C., Oya, S., and Kung, H. F. (2007) Quick assembly of 1,4-diphenyltriazoles as probes targeting β-amyloid aggregates in Alzheimer's disease. J. Med. Chem. 50, 3380-3387.
11. Qu, W., Kung, M.-P., Hou, C., Benedum, T. E., and Kung, H. F. (2007) Novel styrylpyridines as probes for SPECT imaging of amyloid plaques. J. Med. Chem. 50, 2157-2165.
12. Chandra, R., Oya, S., Kung, M.-P., Hou, C., Jin, L.-W., and Kung, H. F. (2007) New diphenylacetylenes as probes for positron emission tomographic imaging of amyloid plaques. J. Med. Chem. 50, 2415-2423.
13. Maggio, J. E., Stimson, E. R., Ghilardi, J. R., Allen, C. J., Dahl, C. E., Whitcomb, D. C., Vigna, S. R., Vinters, H. V., Labenski, M. E., and Mantyh, P. W. (1992) Reversible in vitro growth of Alzheimer disease β-amyloid plaques by deposition of labeled amyloid peptide. Proc. Natl. Acad. Sci. U.S.A. 89, 5462-5466.
14. Wu, D., Yang, J., and Pardridge, W. M. (1997) Drug targeting of a peptide radiopharmaceutical through the primate blood-brain barrier in vivo with a monoclonal antibody to the human insulin receptor. J. Clin. Invest. 100, 1804-1812.
15. 1-40/vector complex. Proc. Natl. Acad. Sci. U.S.A. 92, 10227-10231.
16. Chalifour, R. J., McLaughlin, R. W., Lavoie, L., Morissette, C., Tremblay, N., Boule, M., Sarazin, D. S., Lacombe, D., Tremblay, P., and Gervais, F. (2003) Stereoselective interactions of peptide inhibitors with the β-amyloid peptide. J. Biol. Chem. 278, 34874-34881.
17. Zhang, G., Leibowitz, M. J., Sinko, P. J., and Stein, S. (2003) Multiple-peptide conjugates for binding β-amyloid plaques of Alzheimer's disease. Bioconjugate Chem. 14, 86-92.
18. Gazit, E. (2002) Mechanistic studies of the process of amyloid fibrils formation by the use of peptide fragments and analogues: implications for the design of fibrillization inhibitors. Curr. Med. Chem. 9, 1725-1735.
19. Gordon, D. J., Sciarretta, K. L., and Meredith, S. C. (2001) Inhibition of 102-amyloid(40) fibrillogenesis and disassembly of β-amyloid(40) fibrils by short β-amyloid congeners containing N-methyl amino acids at alternate residues. Biochemistry 40, 8237-8245.
20. Soto, C., Kindy, M. S., Baumann, M., and Frangione, B. (1996) Inhibition of Alzheimer's amyloidosis by peptides that prevent β-sheet conformation. Biochem. Biophys. Res. Commun. 226, 672-680.
21. Soto, C., Sigurdsson, E. M., Morelli, L., Kumar, R. A., Castano, E. M., and Frangione, B. (1998) β-Sheet breaker peptides inhibit fibrillogenesis in a rat brain model of amyloidosis: Implications for Alzheimer's therapy. Nat. Med. 4, 822-826.
22. Findeis, M. A., Musso, G. M., Arico-Muendel, C. C., Benjamin, H. W., Hundal, A. M., Lee, J.-J., Chin, J., Kelley, M., Wakefield, J., Hayward, N. J., and Molineaux, S. M. (1999) Modified-peptide inhibitors of amyloid β-peptide polymerization. Biochemistry 38, 6791-6800.
23. Chan, W. C., and White, P. D. (2000) FMOC Solid-Phase Peptide Synthesis, A Practical Approach, Oxford University Press, New York.
24. Li, D., and Elbert, D. L. (2002) The kinetics of the removal of the N-methyltrityl (mtt) group during synthesis of branched peptides. J. Pept. Res. 60, 300-303.
25. Poduslo, J. F., Curran, G. L., Kumar, A., Frangione, B., and Soto, C. (1999) Beta-sheet breaker peptide inhibitor of Alzheimer's amyloidogenesis with increased blood-brain barrier permeability and resistance to proteolytic degradation in plasma. J. Neurobiol. 39, 371-382.
26. Mathis, C. A., Wang, Y., and Klunk, W. E. (2004) Imaging β-amyloid plaques and neurofibrillary tangles in the aging human brain. Curr. Pharm. Des. 10, 1469-1492.
27. LeVine, H. I. (1993) Thioflavine T interaction with synthetic Alzheimer's disease β-amyloid peptides: Detection of amyloid aggregation in solution. Protein Sci. 2, 404-410.
28. Adessi, C., Frossard, M.-J., Boissard, C., Fraga, S., Bieler, S., Ruckle, T., Vilbois, F., Robinson, S. M., Mutter, M., Banks, W. A., and Soto, C. (2003) Pharmacological profiles of peptide drug candidates for the treatment of Alzheimer's disease. J. Biol. Chem. 278, 13905-13911.
29. Hetenyi, C., Kortvelyesi, T., and Penke, B. (2002) Mapping of possible binding sequences of two β-sheet breaker peptides on β-amyloid peptide of Alzheimer's disease. Bioorg. Med. Chem. 10, 1587-1593.
30. 99mTc-aquaion labels peptide to an unprecedented high specific activity. J. Nucl. Med. 40, 1913-1917.
31. - in aqueous solution and its reaction with a bifunctional ligand. J. Am. Chem. Soc. 120, 7987-7988.
32. + (M=Re, Tc) directed towards radiopharmaceutical application. Coord. Chem. Rev. 190-192, 901-919.
33. +. J. Am. Chem. Soc. 123, 3135-3136.
34. Jaouen, G., Top, S., Vessieres, A., and Alberto, R. (2000) New paradigms for synthetic pathways inspired by bioorganometallic chemistry. J. Organomet. Chem. 600, 23-26.