Myelin imaging compound (MIC) enhanced magnetic resonance imaging of myelination

Journal of Medicinal Chemistry

Volumn 55, Issue 1, 2012, Pages 94-105

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

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

^b CASE WESTERN RESERVE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CONTRAST MEDIUM; GADOLINIUM; MYELIN IMAGING COMPOUND; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DEMYELINATION; DISEASE COURSE; KINETICS; MYELINATION; NONHUMAN; NUCLEAR MAGNETIC RESONANCE IMAGING; RAT;

ANIMALS; BRAIN; CONTRAST MEDIA; COORDINATION COMPLEXES; DEMYELINATING DISEASES; GADOLINIUM; INFUSIONS, INTRAVENTRICULAR; MAGNETIC RESONANCE IMAGING; MYELIN SHEATH; RATS; RATS, SPRAGUE-DAWLEY; STAINING AND LABELING;

EID: 84862954903     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm201010e     Document Type: Article

References (49)

1. Quarles, R. H.; MacKlin, W. B.; Morell, P. Myelin Formation, Structure and Biochemistry. In Basic Neurochemistry: Molecular, Cellular, and Medical Aspects; Siegel, G. J., Albers, R. W., Brady, S., Price, D., Eds.; Elsevier Academic: Burlington, MA, 2006; pp 51-72.
2. Hauw, J. J.; Delaere, P.; Seilhean, D.; Cornu, P. Morphology of demyelination in the human central nervous system J. Neuroimmunol. 1992, 40, 139-152
3. 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
4. Deloire-Grassin, M. S.; Brochet, B.; Quesson, B.; Delalande, C.; Dousset, V.; Canioni, P.; Petry, K. G. In vivo evaluation of remyelination in rat brain by magnetization transfer imaging J. Neurol. Sci. 2000, 178, 10-16
5. Dousset, V.; Grossman, R. I.; Ramer, K. N.; Schnall, M. D.; Young, L. H.; Gonzalez-Scarano, F.; Lavi, E.; Cohen, J. A. Experimental allergic encephalomyelitis and multiple sclerosis: lesion characterization with magnetization transfer imaging Radiology 1992, 182, 483-491
6. Henkelman, R. M.; Huang, X.; Xiang, Q. S.; Stanisz, G. J.; Swanson, S. D.; Bronskill, M. J. Quantitative interpretation of magnetization transfer Magn. Reson. Med. 1993, 29, 759-766
7. Morrison, C.; Henkelman, R. M. A model for magnetization transfer in tissues Magn. Reson. Med. 1995, 33, 475-482
8. Sled, J. G.; Pike, G. B. Quantitative interpretation of magnetization transfer in spoiled gradient echo MRI sequences J. Magn. Reson. 2000, 145, 24-36
9. Sled, J. G.; Pike, G. B. Quantitative imaging of magnetization transfer exchange and relaxation properties in vivo using MRI Magn. Reson. Med. 2001, 46, 923-931
10. Narayanan, S.; Francis Simon, J.; Sled John, G.; Santos, A. C.; Antel, S.; Levesque, I.; Brass, S.; Lapierre, Y.; Sappey-Marinier, D.; Pike, G. B.; Arnold Douglas, L. Axonal injury in the cerebral normal-appearing white matter of patients with multiple sclerosis is related to concurrent demyelination in lesions but not to concurrent demyelination in normal-appearing white matter NeuroImage 2006, 29, 637-642
11. Moore, G. R.; Leung, E.; MacKay, A. L.; Vavasour, I. M.; Whittall, K. P.; Cover, K. S.; Li, D. K.; Hashimoto, S. A.; Oger, J.; Sprinkle, T. J.; Paty, D. W. A pathology-MRI study of the short-T2 component in formalin-fixed multiple sclerosis brain Neurology 2000, 55, 1506-1510
12. Rovaris, M.; Filippi, M. Diffusion tensor MRI in multiple sclerosis J. Neuroimaging 2007, 17 (Suppl. 1) 27S-30S
13. van Zijl, P. C. M.; Nagae-Poetscher, L.; Mori, S. Quantitative Diffusion Imaging. In MR Imaging in White Matter Diseases of the Brain and Spinal Cord; Filippi, M.; Stefano, N. D.; Dousset, V.; McGowan, J. C., Eds.; Springer: New York, 2005; pp 63-81.
14. Bendszus, M.; Ladewig, G.; Jestaedt, L.; Misselwitz, B.; Solymosi, L.; Toyka, K.; Stoll, G. Gadofluorine M enhancement allows more sensitive detection of inflammatory CNS lesions than T2-w imaging: a quantitative MRI study Brain 2008, 131, 2341-2352
15. Wessig, C. Detection of blood-nerve barrier permeability by magnetic resonance imaging Methods Mol. Biol. 2011, 686, 267-271
16. Stankoff, B.; Wang, Y.; 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. U.S.A. 2006, 103, 9304-9309
17. 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
18. Wang, C.; Wu, C.; Popescu, D. C.; Zhu, J.; Macklin, W. B.; Miller, R. H.; Wang, Y. Longitudinal near-infrared imaging of myelination J. Neurosci. 2011, 31, 2382-2390
19. Wang, C.; Wu, C.; Zhu, J.; Miller, R. H.; Wang, Y. Design, synthesis, and evaluation of coumarin-based molecular probes for imaging of myelination J. Med. Chem. 2011, 54, 2331-2340
20. Wang, Y.; Wu, C.; 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. 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
22. Wu, C.; Wang, C.; Popescu, D. C.; Zhu, W.; Somoza, E. A.; Zhu, J.; Condie, A. G.; Flask, C. A.; 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. 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
24. Aime, S.; Anelli, P. L.; Botta, M.; Fedeli, F.; Grandi, M.; Paoli, P.; Uggeri, F. Synthesis, characterization, and 1/T1 NMRD profiles of gadolinium(III) complexes of monoamide derivatives of DOTA-like ligands. X-ray structure of the 10-[2-[[2-hydroxy-1-(hydroxymethyl)ethyl]amino]-1- [(phenylmethoxy)methyl]-2-oxoethyl]-1,4,7,10-tetraazacyclododecane-1,4, 7-triacetic acid-gadolinium(III) complex Inorg. Chem. 1992, 31, 2422-2428
25. Jurkin, D.; Gildehaus, F. J.; Wierczinski, B. Dissociation kinetics determination of yttrium(III)-polyaminocarboxylates using free-ion selective radiotracer extraction (FISRE) J. Labelled Compd. Radiopharm. 2009, 52, 33-40
26. Kumar, K.; Chang, C. A.; Francesconi, L. C.; Dischino, D. D.; Malley, M. F.; Gougoutas, J. Z.; Tweedle, M. F. Synthesis, stability, and structure of gadolinium(III) and yttrium(III) macrocyclic poly(amino carboxylates) Inorg. Chem. 1994, 33, 3567-3575
27. Frullano, L.; Wang, C.; Miller, R. H.; Wang, Y. A myelin-specific contrast agent for magnetic resonance imaging of myelination J. Am. Chem. Soc. 2011, 133, 1611-1613
28. Laurent, S.; Vander Elst, L.; Henoumont, C.; Muller, R. N. How to measure the transmetallation of a gadolinium complex Contrast Media Mol. Imaging 2010, 5, 305-308
29. Laurent, S.; Vander, L.; Copoix, F.; Muller, R. N. Stability of MRI paramagnetic contrast media: a proton relaxometric protocol for transmetalation assessment Invest. Radiol. 2001, 36, 115-122
30. Liu, X.; Byrne, R. H. Rare earth and yttrium phosphate solubilities in aqueous solution Geochim. Cosmochim. Acta 1997, 61, 1625-1633
31. de Sousa Paulo, L.; Livramento Joao, B.; Helm, L.; Merbach Andre, E.; Meme, W.; Doan, B.-T.; Beloeil, J.-C.; Prata Maria, I. M.; Santos Ana, C.; Geraldes Carlos, F. G. C.; Toth, E. In vivo MRI assessment of a novel GdIII-based contrast agent designed for high magnetic field applications Contrast Media Mol. Imaging 2008, 3, 78-85
32. Rohrer, M.; Bauer, H.; Mintorovitch, J.; Requardt, M.; Weinmann, H.-J. Comparison of magnetic properties of MRI contrast media solutions at different magnetic field strengths Invest. Radiol. 2005, 40, 715-724
33. Franklin, K. B. J.; Paxinos, G. The Mouse Brain in Stereotaxic Coordinates, 3 rd ed.; Elsevier Academic Press Inc.: San Diego, CA, 2007.
34. Ford, C. C.; Ceckler, T. L.; Karp, J.; Herndon, R. M. Magnetic resonance imaging of experimental demyelinating lesions Magn. Reson. Med. 1990, 14, 461-481
35. Paxinos, G.; Watson, C. The Rat Brain in Stereotaxic Coordinates, 6 th ed.; Elsevier Academic Press Inc.: San Diego, CA, 2007.
36. Schmidt, K., F.; Ziu, M.; Schmidt, N., Ole; Vaghasia, P.; Cargioli, T., G.; Doshi, S.; Albert, M., S.; Black, P. M., L.; Carroll, R. S.; Sun, Y. Volume reconstruction techniques improve the correlation between histological and in vivo tumor volume measurements in mouse models of human gliomas J. Neurooncol. 2004, 68, 207-215
37. Caravan, P.; Ellison, J. J.; McMurry, T. J.; Lauffer, R. B. Gadolinium(III) chelates as MRI contrast agents: structure, dynamics, and applications Chem. Rev. 1999, 99, 2293-2352
38. Behra-Miellet, J.; Gressier, B.; Brunet, C.; Dine, T.; Luyckx, M.; Cazin, M.; Cazin, J.-C. Free gadolinium and gadodiamide, a gadolinium chelate used in magnetic resonance imaging: evaluation of their in vitro effects on human neutrophil viability Methods Find. Exp. Clin. Pharmacol. 1996, 18, 437-442
39. Husztik, E.; Lazar, G.; Parducz, A. Electron microscopic study of Kupffer-cell phagocytosis blockade induced by gadolinium chloride Br. J. Exp. Pathol. 1980, 61, 624-630
40. Itoh, N.; Kawakita, M. Characterization of gadolinium(3+) and terbium(3+) binding sites on calcium-magnesium adenosine triphosphatase of sarcoplasmic reticulum J. Biochem. 1984, 95, 661-669
41. Spencer, A. J.; Wilson, S. A.; Batchelor, J.; Reid, A.; Rees, J.; Harpur, E. Gadolinium chloride toxicity in the rat Toxicol. Pathol. 1997, 25, 245-255
42. Biagi, B. A.; Enyeart, J. J. Gadolinium blocks low- and high-threshold calcium currents in pituitary cells Am. J. Physiol. 1990, 259, C515-C520
43. Lansman, J. B. Blockade of current through single calcium channels by trivalent lanthanide cations. Effect of ionic radius on the rates of ion entry and exit J. Gen. Physiol. 1990, 95, 679-696
44. Boyd Alan, S.; Zic John, A.; Abraham Jerrold, L. Gadolinium deposition in nephrogenic fibrosing dermopathy J. Am. Acad. Dermatol. 2007, 27-30
45. Vorobiov, M.; Basok, A.; Tovbin, D.; Shnaider, A.; Katchko, L.; Rogachev, B. Iron-mobilizing properties of the gadolinium-DTPA complex: clinical and experimental observations Nephrol., Dial., Transplant. 2003, 18, 884-887
46. Caravan, P.; Farrar, C. T.; Frullano, L.; Uppal, R. Influence of molecular parameters and increasing magnetic field strength on relaxivity of gadolinium- and manganese-based T1 contrast agents Contrast Media Mol. Imaging 2009, 4, 89-100
47. Allkemper, T.; Bremer, C.; Matuszewski, L.; Ebert, W.; Reimer, P. Contrast-enhanced blood-pool MR angiography with optimized iron oxides: effect of size and dose on vascular contrast enhancement in rabbits Radiology 2002, 223, 432-438
48. Josephson, L.; Lewis, J.; Jacobs, P.; Hahn, P. F.; Stark, D. D. The effects of iron oxides on proton relaxivity Magn. Reson. Imaging 1988, 6, 647-653
49. Pardridge, W. M. The blood-brain barrier: bottleneck in brain drug development NeuroRx 2005, 2, 3-14