Evaluation of nonionic nitroxyl lipids as potential organ-specific contrast agents for magnetic resonance imaging

Magnetic Resonance Imaging - Tập 10 - Trang 445-455 - 1992
Bernard Gallez1, Roger Demeure2, Rene Debuyst3, Dominique Leonard1, Fernand Dejehet3, Pierre Dumont1
1Department of Pharmaceutical Sciences, Laboratory of Medicinal Chemistry, Catholic University of Louvain, B-1200 Brussels, Belgium
2Department of Radiology, Cliniques Universitaires Saint-Luc, B-1200 Brussels, Belgium
3Laboratory of Inorganic, Analytical, and Nuclear Chemistry, Catholic University of Louvain, B-1348 Louvain-la-Neuve, Belgium

Tài liệu tham khảo

Carr, 1985, Contrast agents in magnetic resonance imaging, Clin. Radiol., 36, 561, 10.1016/S0009-9260(85)80234-8 Carr, 1985, The use of proton relaxation enhancers in magnetic resonance imaging, Magn. Reson. Imaging, 3, 17, 10.1016/0730-725X(85)90005-0 Lauffer, 1988, Iron-EHPG as an hepatobiliary MR contrast agent: Initial imaging and biodistribution studies, Nucl. Med. Biol., 15, 47 Kawamura, 1989, Gadolinium-phthalein complexone as a contrast agent for hepatobiliary MR imaging, J. Comput. Assist. Tomogr., 1, 67, 10.1097/00004728-198901000-00014 Brasch, 1983, Work in progress: Methods of contrast enhancement for NMR imaging and potential applications, Radiology, 147, 781, 10.1148/radiology.147.3.6342034 Lurie, 1988, Proton-electron double magnetic resonance imaging of free radical solutions, J. Magn. Reson., 76, 366 Lurie, 1989, Field-cycled proton-electron double-resonance imaging of free radicals in large aqueous samples, J. Magn. Reson., 84, 431 Swartz, 1985, Feasibility of measuring oxygen and redox metabolism in vivo NMR: Effect of paramagnetic materials and their cellular metabolism on relaxation times of protons of water and lipids, Period. Biol., 87, 175 Iannone, 1989, Metabolism of aqueous soluble nitroxides in hepatocytes: Effects of cell integrity, oxygen, and structure of nitroxides, Biochim. Biophys. Acta, 991, 90, 10.1016/0304-4165(89)90033-0 Swartz, 1986, Cellular metabolism of water soluble nitroxides: Effect on rate of reduction of cell/nitroxide ratio, oxygen concentrations and permeability of nitroxides, Biochim. Biophys. Acta, 888, 82, 10.1016/0167-4889(86)90073-X Chen, 1989, Effect of oxygen on the metabolism of nitroxide spin labels in cells, Biochemistry, 28, 2496, 10.1021/bi00432a022 Ehman, 1986, Diradical nitroxyl spin label contrast agents for magnetic resonance imaging. A comparison of relaxation effectiveness, Invest. Radiol., 21, 125, 10.1097/00004424-198602000-00008 Almen, 1985, Development of nonionic contrast media, Invest. Radiol., 20, S1 Grodd, 1987, Comparison of ionic and nonionic nitroxide spin labels for urographic enhancement in magnetic resonance imaging, Acta Radiol., 28, 593, 10.3109/02841858709177407 Bennett, 1990, Interactions of nitroxides with plasma and blood: Effect on 1T1 of water protons, Magn. Reson. Med., 14, 40, 10.1002/mrm.1910140106 Weichert, 1986, Potential tumor- or organ-imaging agents. Polyiodinated 2-substituted triacylglycerols as hepatographic agents, J. Med. Chem., 29, 1674, 10.1021/jm00159a019 Belfrage, 1964, The tissue distribution and metabolism in the rat of intravenously injected labeled fat emulsions, Acta Physiol. Scand., 62, 344, 10.1111/j.1748-1716.1964.tb10432.x Couet, 1985, Influence of chemical structure of nitroxyl spin labels on their reduction by ascorbic acid, Tetrahedron, 41, 1165, 10.1016/S0040-4020(01)96516-0 Keana, 1987, Nitroxides as potential contrast enhancing agents for MRI application: Influence of structure on the rate of reduction by rat hepatocytes, whole liver homogenate, subcellular fractions, and ascorbate, Magn. Reson. Med., 5, 525, 10.1002/mrm.1910050603 Couet, 1985, Factors affecting nitroxide reduction in ascorbate solution and tissue homogenates, Magn. Reson. Imaging, 3, 83, 10.1016/0730-725X(85)90012-8 Morrison, 1970, Mass spectrometry of piperidine nitroxides, a class of stable free radicals, Org. Mass Spectrom., 3, 353, 10.1002/oms.1210030310 Davies, 1974, Mass spectrometry of stable free radicals: Pyrrolidine nitroxides, Org. Mass Spectrom., 8, 43, 10.1002/oms.1210080106 Sosnovsky, 1989, Synthesis of nitroxyl (aminoxyl) labeled probes for studies of intracellular environment by EPR and MRI, J. Org. Chem., 54, 3667, 10.1021/jo00276a031 De Boer, 1963, Diazomethane, Collective Volume 4, 250 Press, 1986, 523 Brown, 1985, Effects of the operating magnetic field on potential NMR contrast agents, Magn. Reson. Imaging, 3, 3, 10.1016/0730-725X(85)90003-7 Isa, 1988, Solubilisation des cytochromes P-450 humains par diverses classes de détergents, J. Pharm. Belg., 43, 246 Cumps, 1977, Michaelis-Menten kinetic analysis of the hepatic microsomal benzpyrene hydroxylase from control, phenobarbital- and methyl-3-cholanthrene-treated rats, Chem.-Biol. Interactions, 16, 23, 10.1016/0009-2797(77)90151-X Kwan, 1979, Electron spin resonance study of coal by line width and line shape analysis, Anal. Chem., 51, 1225, 10.1021/ac50044a028 Goldberg, 1981, Chemical analysis by EPR, vol. 6, 1 Lorke, 1983, A new approach to practical acute testing, Arch. Toxicol., 54, 275, 10.1007/BF01234480 Baldassare, 1974, A spin-label study of energy-coupled active transport in Escherichia coli membrane vesicles, Biochemistry, 13, 5210, 10.1021/bi00722a025 Ehman, 1985, Enhanced MRI tumors utilizing a new nitroxyl spin label contrast agent, Magn. Reson. Imaging, 3, 89, 10.1016/0730-725X(85)90013-X Brasch, 1983, Work in progress: Nuclear magnetic resonance study of a paramagnetic nitroxide contrast agent for enhancement of renal structures in experimental animals, Radiology, 147, 773, 10.1148/radiology.147.3.6844613 Herfkens, 1981, Nuclear magnetic resonance imaging of the abnormal live rat and correlations with tissue characteristics, Radiology, 141, 211, 10.1148/radiology.141.1.7197379 Bennett, 1987, Effects of nitroxides on the magnetic field and temperature dependence of 1T1 of solvent water protons, Magn. Reson. Med., 4, 93, 10.1002/mrm.1910040202 Jacob, 1985, γ-Aminobutyric acid esters. 2. Synthesis, brain uptake, and pharmacological properties of lipid esters of γ-aminobutyric acid, J. Med. Chem., 28, 106, 10.1021/jm00379a019 Jacob, 1987, γ-Aminobutyric esters. 3. Synthesis, brain uptake, and pharmacological properties of C-18 glyceryl lipid esters of GABA with varying degree of unsaturation, J. Med. Chem., 30, 1573, 10.1021/jm00392a008 Jacob, 1990, Synthesis, brain uptake, and pharmacological properties of a glyceryl lipid containing GABA and the GABA-T inhibitor γ-vinyl-GABA, J. Med. Chem., 33, 733, 10.1021/jm00164a042 Mergen, 1991, Antiepileptic activity of 1,3-dihexadecanoylamino-2-valproyl-propan-2-ol, a prodrug of valproic acid endowed with a tropism for the CNS, J. Pharm. Pharmacol., 43, 815, 10.1111/j.2042-7158.1991.tb03491.x