Solid-Phase Synthesis of Styryl Dyes and their Application as Amyloid Sensors†
Qian Li
Department of Chemistry, New York University, New York, NY 10003, USA, Fax: (+1) 212-995-4203
Search for more papers by this authorJun-Seok Lee
Department of Chemistry, New York University, New York, NY 10003, USA, Fax: (+1) 212-995-4203
Search for more papers by this authorChanki Ha
Department of Chemical & Materials Engineering, Arizona State University, Tempe, AZ 85287-6006, USA, Fax: (+1) 480-965-0037
Search for more papers by this authorChan Beum Park Prof. Dr.
Department of Chemical & Materials Engineering, Arizona State University, Tempe, AZ 85287-6006, USA, Fax: (+1) 480-965-0037
Search for more papers by this authorGuang Yang
Skirball Institute of Biomolecular Medicine, New York University School of Medicine, 540 First Avenue, New York, NY 10016-6481, USA, Fax: (+1) 212-263-8214
Search for more papers by this authorWen Biao Gan Prof. Dr.
Skirball Institute of Biomolecular Medicine, New York University School of Medicine, 540 First Avenue, New York, NY 10016-6481, USA, Fax: (+1) 212-263-8214
Search for more papers by this authorYoung-Tae Chang Prof. Dr.
Department of Chemistry, New York University, New York, NY 10003, USA, Fax: (+1) 212-995-4203
Search for more papers by this authorQian Li
Department of Chemistry, New York University, New York, NY 10003, USA, Fax: (+1) 212-995-4203
Search for more papers by this authorJun-Seok Lee
Department of Chemistry, New York University, New York, NY 10003, USA, Fax: (+1) 212-995-4203
Search for more papers by this authorChanki Ha
Department of Chemical & Materials Engineering, Arizona State University, Tempe, AZ 85287-6006, USA, Fax: (+1) 480-965-0037
Search for more papers by this authorChan Beum Park Prof. Dr.
Department of Chemical & Materials Engineering, Arizona State University, Tempe, AZ 85287-6006, USA, Fax: (+1) 480-965-0037
Search for more papers by this authorGuang Yang
Skirball Institute of Biomolecular Medicine, New York University School of Medicine, 540 First Avenue, New York, NY 10016-6481, USA, Fax: (+1) 212-263-8214
Search for more papers by this authorWen Biao Gan Prof. Dr.
Skirball Institute of Biomolecular Medicine, New York University School of Medicine, 540 First Avenue, New York, NY 10016-6481, USA, Fax: (+1) 212-263-8214
Search for more papers by this authorYoung-Tae Chang Prof. Dr.
Department of Chemistry, New York University, New York, NY 10003, USA, Fax: (+1) 212-995-4203
Search for more papers by this authorWe thank BeadTech Inc., Korea, for technical support of this work.
Graphical Abstract
The combinatorial approach: A library of fluorescent styryl dyes (320 compounds) was prepared by solid-phase chemistry. The dyes were screened for their detection of amyloid aggregates, which are associated with diseases such as Alzheimer's, and two of the 320 compounds screened, 2C40 and 2E10, showed promise as brain-imaging agents (see microscopy image).
Supporting Information
Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2004/z461600_s.pdf or from the author.
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
References
- 1 Fluorescent Chemosensors for Ion and Molecule Recognition (Ed.: ), American Chemical Society, Washington DC, 1992.
- 2W. Rettig, B. Strehmel, J. Schrader, H. Seifert, Applied Fluorescence in Chemistry, Biology, and Medicine, Springer, Berlin, 1999.
10.1007/978-3-642-59903-3 Google Scholar
- 3J. R. Lakowicz, Principles of Fluorescence Spectroscopy, Klewer Academic/Plenum Publishers, New York, 1999.
10.1007/978-1-4757-3061-6 Google Scholar
- 4K. C. Nicolaou, R. Hanko, W. Hartwig, Handbook of Combinatorial Chemistry: Drugs, Catalysts, Materials, Wiley-VCH, Weinheim, 2002.
10.1002/3527603034 Google Scholar
- 5S. Miertus, G. Fassina, Combinatorial Chemistry and Technology: Principles, Methods, and Applications, Book News, New York, 1999.
- 6J. C. Loren, J. S. Siegel, Angew. Chem. 2001, 113, 776–779;
10.1002/1521-3757(20010216)113:4<776::AID-ANGE7760>3.0.CO;2-P Google ScholarAngew. Chem. Int. Ed. 2001, 40, 754–757.10.1002/1521-3773(20010216)40:4<754::AID-ANIE7540>3.0.CO;2-T CAS PubMed Web of Science® Google Scholar
- 7M. S. Schiedel, C. A. Briehn, P. Bauerle, Angew. Chem. 2001, 113, 4813–4816;
10.1002/1521-3757(20011217)113:24<4813::AID-ANGE4813>3.0.CO;2-T Google ScholarAngew. Chem. Int. Ed. 2001, 40, 4677–4680.10.1002/1521-3773(20011217)40:24<4677::AID-ANIE4677>3.0.CO;2-U CAS PubMed Web of Science® Google Scholar
- 8A. M. Song, J. H. Zhang, K. S. Lam, J. Comb. Chem. 2004, 6, 112–120.
- 9J. M. Gao, C. Strassler, D. Tahmassebi, E. T. Kool, J. Am. Chem. Soc. 2002, 124, 11 590–11 591.
- 10O. Lavastre, I. Illitchev, G. Jegou, P. H. Dixneuf, J. Am. Chem. Soc. 2002, 124, 5278–5279.
- 11G. R. Rosania, J. W. Lee, L. Ding, H. S. Yoon, Y. T. Chang, J. Am. Chem. Soc. 2003, 125, 1130–1131.
- 12J. D. Sipe, A. S. Cohen, J. Struct. Biol. 2000, 130, 88–98.
- 13J. W. Kelly, Curr. Opin. Struct. Biol. 1996, 6, 11–17.
- 14R. M. Murphy, Annu. Rev. Biomed. Eng. 2002, 4, 155–174.
- 15C. M. Clark, Neurodegenerative Dementias: Clinical Features and Pathological Mechanisms, McGraw–Hill, New York, 2000.
- 16T. A. Bayer, O. Wirths, K. Majtenyi, T. Hartmann, G. Multhaup, K. Beyreuther, C. Czech, Brain Pathol. 2001, 11, 1–11.
- 17J. Hardy, D. J. Selkoe, Science 2002, 297, 353–356.
- 18J. D. Harper, S. S. Wong, C. M. Lieber, P. T. Lansbury, Chem. Biol. 1997, 4, 119–125.
- 19J. D. Harper, P. T. Lansbury, Annu. Rev. Biochem. 1997, 66, 385–407.
- 20G. T. Westermark, K. H. Johnson, P. Westermark, Methods Enzymol. 1999, 309, 3–25.
- 21B. Urbanc, L. Cruz, R. Le, J. Sanders, K. H. Ashe, K. Duff, H. E. Stanley, M. C. Irizarry, B. T. Hyman, Proc. Natl. Acad. Sci. USA 2002, 99, 13 990–13 995.
- 22A. Arora, C. Ha, C. B. Park, FEBS Lett. 2004, 564, 121–125.
- 23L. Nielsen, R. Khurana, A. Coats, S. Frokjaer, J. Brange, S. Vyas, V. N. Uversky, A. L. Fink, Biochemistry 2001, 40, 6036–6046.
- 24A. Ahmad, I. S. Millett, S. Doniach, V. N. Uversky, A. L. Fink, Biochemistry 2003, 42, 11 404–11 416.
- 25G. Bitan, M. D. Kirkitadze, A. Lomakin, S. S. Vollers, G. B. Benedek, D. B. Teplow, Proc. Natl. Acad. Sci. USA 2003, 100, 330–335.
- 26R. H. Christie, B. J. Bacskai, W. R. Zipfel, R. M. Williams, S. T. Kajdasz, W. W. Webb, B. T. Hyman, J. Neurosci. 2001, 21, 858–864.