Design, synthesis, and evaluation of coumarin-based molecular probes for imaging of myelination

Journal of Medicinal Chemistry

Volumn 54, Issue 7, 2011, Pages 2331-2340

  Wang, Changning ^a   Wu, Chunying ^a   Zhu, Junqing ^a   Miller, Robert H ^a   Wang, Yanming ^a  

^a CASE WESTERN RESERVE UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 [4 (DIMETHYLAMINO)PHENYL] 7 (3 FLUOROPROPOXY) 2H CHROMEN 2 ONE; COUMARIN DERIVATIVE; FLUORESCENT DYE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DRUG DESIGN; DRUG SCREENING; DRUG SYNTHESIS; MOLECULAR PROBE; MOUSE; MYELINATION; NONHUMAN; POSITRON EMISSION TOMOGRAPHY; STRUCTURE ACTIVITY RELATION;

ANIMALS; CENTRAL NERVOUS SYSTEM; COUMARINS; DRUG DESIGN; DRUG EVALUATION, PRECLINICAL; MICE; MOLECULAR IMAGING; MOLECULAR PROBES; MYELIN SHEATH; STAINING AND LABELING; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 79953787899     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm101489w     Document Type: Article

References (30)

1. Compston, A.; Coles, A. Multiple sclerosis Lancet 2002, 359, 1221-1231 (Pubitemid 34304266)
2. Compston, A.; Coles, A. Multiple sclerosis Lancet 2008, 372, 1502-1517
3. Rosati, G. The prevalence of multiple sclerosis in the world: an update Neurol. Sci. 2001, 22, 117-139 (Pubitemid 33771279)
4. Ascherio, A.; Munger, K. L. Environmental risk factors for multiple sclerosis. Part I: the role of infection Ann. Neurol. 2007, 61, 288-299 (Pubitemid 46676728)
5. Lublin, F. D.; Reingold, S. C. Defining the clinical course of multiple sclerosis: results of an international survey. National Multiple Sclerosis Society (USA) Advisory Committee on Clinical Trials of New Agents in Multiple Sclerosis Neurology 1996, 46, 907-911
6. Liu, L.; Darnall, L.; Taofang, H.; Choi, K.; Lane, T. E.; Ransohoff, R. M. Myelin Repair Is Accelerated by Inactivating CXCR2 on Nonhematopoietic Cells J. Neurosci. 2010, 30, 9074-9083
7. Piaton, G.; Gould, R. M.; Lubetzki, C. Axon-oligodendrocyte interactions during developmental myelination, demyelination and repair J. Neurochem. 2010, 114, 1243-1260
8. Miller, R. H.; Sha, M. Dissecting demyelination Nat. Neurosci. 2007, 10, 1351-1354 (Pubitemid 350014684)
9. Matsas, R.; Lavdas, A. A.; Papastefanaki, F.; Thomaidou, D. Schwann Cell Transplantation for CNS Repair Curr. Med. Chem. 2008, 15, 151-160 (Pubitemid 351234618)
10. Peru, R. L.; Mandrycky, N.; Nait-Oumesmar, B.; Lu, Q. R. Paving the Axonal Highway: From Stem Cells to Myelin Repair Stem Cell Rev. 2008, 4, 304-318
11. Mozafari, S.; Sherafat, M. A.; Javan, M.; Mirnajafi-Zadeh, J.; Tiraihi, T. Visual evoked potentials and MBP gene expression imply endogenous myelin repair in adult rat optic nerve and chiasm following local lysolecithin induced demyelination Brain Res. 2010, 1351, 50-56
12. Nait-Oumesmar, B.; Picard-Riéra, N.; Kerninon, C.; Baron-Van Evercooren, A. The role of SVZ-derived neural precursors in demyelinating diseases: From animal models to multiple sclerosis J. Neurol. Sci. 2008, 265, 26-31
13. Franklin, R. J.; Hinks, G. L. Understanding CNS remyelination: clues from developmental and regeneration biology J. Neurosci. Res. 1999, 58, 207-213 (Pubitemid 29471422)
14. Stangel, M.; Hartung, H. P. Remyelinating strategies for the treatment of multiple sclerosis Prog. Neurobiol. 2002, 68, 361-376 (Pubitemid 36071512)
15. Polman, C. H.; Reingold, S. C.; Edan, G.; Filippi, M.; Hartung, H. P.; Kappos, L.; Lublin, F. D.; Metz, L. M.; McFarland, H. F.; O'Connor, P. W.; Sandberg-Wollheim, M.; Thompson, A. J.; Weinshenker, B. G.; Wolinsky, J. S. Diagnostic criteria for multiple sclerosis: 2005 revisions to the "McDonald Criteria Ann. Neurol. 2005, 58, 840-846 (Pubitemid 41746873)
16. Molyneux, P. D.; Barker, G. J.; Barkhof, F.; Beckmann, K.; Dahlke, F.; Filippi, M.; Ghazi, M.; Hahn, D.; MacManus, D.; Polman, C.; Pozzilli, C.; Kappos, L.; Thompson, A. J.; Wagner, K.; Yousry, T.; Miller, D. H. Clinical-MRI correlations in a European trial of interferon beta-1b in secondary progressive MS Neurology 2001, 57, 2191-2197 (Pubitemid 34016450)
17. Stankoff, B.; Wang, Y. M.; Bottlaender, M.; Aigrot, M. S.; Dolle, F.; Wu, C.; Feinstein, D.; Huang, G. F.; Semah, F.; Mathis, C. A.; Klunk, W.; Gould, R. M.; Lubetzki, C.; Zalc, B. Imaging of CNS myelin by positron emission tomography Proc. Natl. Acad. Sci. USA 2006, 103, 9304-9309 (Pubitemid 43902573)
18. Wu, C.; Tian, D.; Feng, Y.; Polak, P.; Wei, J.; Sharp, A.; Stankoff, B.; Lubetzki, C.; Zalc, B.; Mufson, E. J.; Gould, R. M.; Feinstein, D. L.; Wang, Y. A novel fluorescent probe that is brain permeable and selectively binds to myelin J. Histochem. Cytochem. 2006, 54, 997-1004 (Pubitemid 44298586)
19. Wu, C.; Wei, J.; Tian, D.; Feng, Y.; Miller, R. H.; Wang, Y. Molecular probes for imaging myelinated white matter in CNS J. Med. Chem. 2008, 51, 6682-6688
20. Caprariello, A. V.; Somoza, E.; Zhu, W.; Wang, C.; Miller, R. H. In vivo quantification of myelin changes in the vertebrate nervous system J. Neurosci. 2009, 29, 14663-14669
21. Wang, C.; Wu, C.; Zhu, J.; Popescu, D. C.; Macklin, W.; Miller, R. H.; Wang, Y. Longitudinal Near Infrared Imaging of Myelination. J. Neurosci. 2010, in press. DOI: 10.1523/JNEUROSCI.2698-10.2010.
22. Wu, C.; Wang, C.; Popescu, D. C.; Zhu, W.; Somoza, E.; Zhu, J.; Flask, C.; Miller, R. H.; Macklin, W.; Wang, Y. A novel PET marker for in vivo quantification of myelination Bioorg. Med. Chem. 2010, 18, 8592-8599
23. Wang, C.; Popescu, D. C.; Wu, C.; Zhu, J.; Macklin, W.; Wang, Y. In Situ fluorescence Imaging of Myelination J. Histochem. Cytochem. 2010, 58, 611-621
24. Casley-Smith, J. R. Benzopyrones in the treatment of lymphedema Int. Angiol. 1999, 18, 41976-41990
25. Luszczki, J. J.; Andres-Mach, M.; Cisowski, W.; Mazol, I.; Glowniak, K.; Czuczwar, S. J. Osthole suppresses seizures in the mouse maximal electroshock seizure model Eur. J. Pharmacol. 2009, 607, 107-109
26. Waxman, S. G.; Bangalore, L. Electrophysiologic consequences of myelination. In Lazzarini, R. A., Ed.; Myelin biology and disorders; Elsevier: London, 2004; Vol. 1, pp 117-143.
27. Podbielska, M.; Hogan, E. L. Molecular and immunogenic features of myelin lipids: incitants or modulators of multiple sclerosis Multiple Sclerosis 2009, 15, 1011-1029
28. Clasen, R. A.; Simon, R. G.; Scott, R.; Pandolfi, S.; Laihg, I.; Lesak, A. The staining of the myelin sheath byluxol dye techniques J. Neuropathol. Exp. Neurol. 1973, 32, 271-283
29. Dischino, D. D.; Welch, M. J.; Kilbourn, A.; Raichle, M. E. Relationship between lipophilicity and brain extraction of C-11-labeled radiopharmaceuticals J. Nucl. Med. 1983, 24, 1030-1038 (Pubitemid 14206457)
30. Hu, Y.; Doudevski, I.; Wood, D.; Moscarello, M.; Husted, C.; Genain, C.; Zasadzinski, J. A.; Israelachvili, J. Synergistic interactions of lipids and myelin basic protein Proc. Natl. Acad. Sci. USA 2004, 101, 13466-1347