Syntheses of Two Potential Ligands for Tc-99m Labeling as Diagnosis Agents of Alzheimer's Disease†
Zhi-Ping Zhuang
Department of Radiology, University of Pennsylvania, Room 305, 3700 Market Street, Philadelphia, Pennsylvania, 19104, USA
Search for more papers by this authorMei-Ping Kung
Department of Radiology, University of Pennsylvania, Room 305, 3700 Market Street, Philadelphia, Pennsylvania, 19104, USA
Search for more papers by this authorMasahiro Ono
Department of Radiology, University of Pennsylvania, Room 305, 3700 Market Street, Philadelphia, Pennsylvania, 19104, USA
Search for more papers by this authorCatherine Hou
Department of Radiology, University of Pennsylvania, Room 305, 3700 Market Street, Philadelphia, Pennsylvania, 19104, USA
Search for more papers by this authorHank F. Kung
Department of Pharmacology, University of Pennsylvania, Room 305, 3700 Market Street, Philadelphia, Pennsylvania, 19104, USA
Search for more papers by this authorZhi-Ping Zhuang
Department of Radiology, University of Pennsylvania, Room 305, 3700 Market Street, Philadelphia, Pennsylvania, 19104, USA
Search for more papers by this authorMei-Ping Kung
Department of Radiology, University of Pennsylvania, Room 305, 3700 Market Street, Philadelphia, Pennsylvania, 19104, USA
Search for more papers by this authorMasahiro Ono
Department of Radiology, University of Pennsylvania, Room 305, 3700 Market Street, Philadelphia, Pennsylvania, 19104, USA
Search for more papers by this authorCatherine Hou
Department of Radiology, University of Pennsylvania, Room 305, 3700 Market Street, Philadelphia, Pennsylvania, 19104, USA
Search for more papers by this authorHank F. Kung
Department of Pharmacology, University of Pennsylvania, Room 305, 3700 Market Street, Philadelphia, Pennsylvania, 19104, USA
Search for more papers by this authorDedicated to Professor ZHOU Wei-Shan on the occasion of his 80th birthday.
Abstract
Two types of ligands-biphenyl and stilbene derivatives, which can be labeled with Tc-99m for the diagnosis of Alzheimer's disease (AD) have been synthesized successfully. The key steps in these two syntheses involved Suzuki reaction and Wittig reaction respectively. The new discovered debromination reaction may be expanded to the compounds with double or triple bond adjacent to the carbon atom bearing the bromine atoms. These types of syntheses provide a route to a series of biphenyl and stilbene derivatives that will benefit the search of new imaging agents for AD.
References
- 1 Xia, W; Ray, W. J.; Ostaszewski, B. L.; Rahmati, T; Kimberly, W. T.; Wolfe, M. S.; Zhang, J; Goate, A. M.; Selkoe, D. J., Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 9299.
- 2 Schenk, D; Barbour, R; Dunn, W; Gordon, G; Grajeda, H; Guido, T; Hu, K; Huang, J; Johnson-Wood, K; Khan, K; Kholodenko, D; Lee, M; Liao, Z; Lieberburg, I; Motter, L; Soriano, F; Shopp, G; Vasquez, N; Vandevert, C; Walker, S; Wogulis, M; Yednock, T; Games, D; Seubert, P., Nature 1999, 400, 173.
- 3 Schenk, D. B.; Seubert, P; Lieberburg, I; Wallace, J., Arch. Neurol. 2000, 57, 934.
- 4 Sherman, M. S.; Beher, D; Clarke, E. E.; Lewis, H. D.; Harrison, T; Hunt, P; Nadin, A; Smith, A. L.; Stevenson, G; Castro, J. L., Biochemistry 2000, 39, 8698.
- 5 Ghosh, A. K.; Shin, D; Downs, D; Keolsch, G; Lin, X; Ermolieff, J; Tang, J., J. Am. Chem. Soc. 2000, 122, 3522.
- 6 Skovronsky, D. M.; Lee, V. M., Trends Pharmacol. Sci. 2000, 21, 161.
- 7 Moore, C. L.; Leatherwood, D. D.; Diehl, T. S.; Selkoe, D. J.; Wolfe, M. S., J. Med. Chem. 2000, 43, 3434.
- 8 Vassar, R; Bennett, B. D.; Babu-Khan, S; Mendiaz, E. A., Science 1999, 286, 735.
- 9 Wolfe, M. S.; Citron, M; Diehl, T. S.; Xia, W; Donkor, I. O.; Selkoe, D., J. Med. Chem. 1998, 41, 6.
- 10 Selkoe, D. J., Nat. Biotechnol. 2000, 18, 823.
- 11 Ashbum, T. T.; Han, H; McGuinness, B. F.; Lansbury, P. T. Jr., Chem. Biol. 1996, 3, 351.
- 12 Han, G; Cho, C.-G; Lansbury, P. T. Jr., J. Am. Chem. Soc. 1996, 118, 4506.
- 13 Klunk, W. E.; Debnath, M. L.; Pettegrew, J. W., Biol. Psychiatry 1994, 35, 611.
- 14 Klunk, W. E.; Debnath, M. L.; Pettegrew, J. W., Neurobiol. Aging 1995, 16, 541.
- 15 Styren, S. D.; Hamilton, R. L.; Styren, G. C.; Klunk, W. E., J. Histochem. Cytochem. 2000, 48, 1223.
- 16 Mathis, C. A.; Mahmood, K; Debnath, M. L.; Klunk, W. E., J. Labelled Compd. Radiopharm. 1997, 39, 894.
- 17 Lorenzo, A; Yankner, B. A., Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 12243.
- 18 Zhen, W; Han, H; Anguiano, M; Lemere, C. A.; Cho, C. G.; Lansbury, P. T. Jr., J. Med. Chem. 1992, 42, 2805.
- 19 Dezutter, N. A.; Dom, R. J.; De Groot, T. J.; Bormans, G. M.; Verbruggen, A. M., Eur. J. Nucl. Med. 1999, 26, 1396.
- 20 Dezutter, N. A.; De Groot, T. J.; Busson, R. H.; Janssen, G. A.; Verbruggen, A. M., J. Labelled Compd. Radiopharm. 1999, 42, 309.
- 21 Agdeppa, E. D.; Kepe, V; Flores-Torres, S; Liu, J; Satyamurthy, N; Petric, A; Vinters, H. V.; Huang, S. C.; Barrio, J. R., J. Nucl. Med. Abstract book supplement 2001, 42, 65P (abstract).
- 22 Agdeppa, E. D.; Kepe, V; Shoghi-Jadid, K; Satyamurthy, N; Small, G. W.; Petric, A; Vinters, H. V.; Huang, S. C.; Barrio, J. R., J. Nucl. Med. 2001, 42, S 65P (abstract).
- 23
Agdeppa, E. D.;
Kepe, V;
Liu, J;
Shoghi-Jadid, K;
Satyamurthy, N;
Small, G. W.;
Petric, A;
Vinters, H. V.;
Huang, S. C.;
Barrio, J. R.,
J. Labelled Compd. Radiopharm.
2001,
44,
S242
10.1002/jlcr.2580440184 Google Scholar
- 24 Mathis, C. A.; Holt, D. P.; Wang, G.-F; Debnath, M. L.; Bacskai, B. J.; Hyman, B. T.; Klunk, W. E., J. Nucl. Med. 2001, 42, 252 P (abstract).
- 25
Mathis, C. A.;
Holt, D. P.;
Wang, G.-F;
Debnath, M. L.;
Klunk, W. E.,
J. Labelled Compd. Radiopharm.
2001,
44,
S26
10.1002/jlcr.2580440110 Google Scholar
- 26(a) Klunk, W. E.; Huang, Y; Huang, G.-F; Debnath, M. L.; Holt, D. P.; Mathis, C. A., Life Sci. 2001, 69, 1471. (b) Klunk, W. E.; Mathis, C. A.; Huang, Y; Huang, G.-F; Holt, D. P.; Debnath, M. L.; Engler, H; Nordberg, A; Blomqvist, G; Bergstrm, M; Estrada, S; Barletta, J; Sandell, J; Antoni, G; Lngstrm, B., 32nd Annual Meeting, Soc. for Neuroscience, Abstract, No. 228.9. Orlando, Florida, U.S.A. 2002.
- 27 Zhuang, Z.-P; Kung, M.-P; Hou, C; Skovronsky, D; Gur, T. L.; Trojanowski, J. Q.; Lee, V. M.-Y; Kung, H. F., J. Med. Chem. 2001, 44, 1905.
- 28 Skovronsky, D; Zhang, B; Kung, M.-P; Kung, H. F.; Trojanowski, J. Q.; Lee, V. M.-Y., Proc. Nad. Acad. Sci. U.S.A. 2000, 97, 7609.
- 29 Sanath, M; Plossl, K; Kung, M.-P; Stevenson, D. A.; Liable-Sands, L. M.; Rheingold, A. L.; Kung, H. F., J. Am. Chem. Soc. 1995, 117, 11037.
- 30 Kung, H. F.; Lee, C. W.; Zhuang, Z.-P; Kung, M.-P; Hou, C; Plossl, K., J. Am. Chem. Soc. 2001, 123, 12740.
- 31 Unpublished work.
- 32 Vanuti, M. C.; Stephenson, R. A.; Alvarez, R; Bruno, J. J.; Strosberg, A. M., J. Med. Chem. 1988, 31, 2136.
- 33 Frankel, M; Gertner, D; Jakobson, H; Zilkha, A., J. Chem. Soc. 1960, 1390.
- 34 Oya, S; Plossl, K; Kung, M.-P; Stevenson, A; Kung, H. F., Nucl. Med. Biol. 1998, 25, 135.
- 35 Diwu, Z; Beachdel, C; Klaubert, D. H., Tetrahedron Lett. 1998, 39, 4987.
- 36 Bottin-Strzalko, T; Seyden-Penne, J., Bull. Soc. Chim. Fr. 1984. 161.