Synthesis of 11C-radiopharmaceuticals using direct fixation of [11C]carbon dioxide and [11C]carbon monoxide

Barrio, 1982, l-[4-11C]Aspartic acid, enzymatic synthesis myocardial uptake and metabolism, J. Med. Chem., 25, 93, 10.1021/jm00343a020 Barrio, 1983, l-[1-11C]Leucine, Routine synthesis by enzymatic resolution, J. Nucl. Med., 24, 515 Berger, 1980, Synthesis of carbon-11 labelled acetone, Int. J. Appl. Radiat Isot., 31, 577, 10.1016/0020-708X(80)90102-7 Berger, 1983, Synthesis of a β-blocker for heart visualization, [11C]Practolol, Int. J. Appl. Radiat Isot., 34, 1556, 10.1016/0020-708X(83)90295-8 Bolster, 1985, The preparation of carbon-11 labeled proline for positron emission tomography. Preliminary distribution studies in rats with Walker 256 carcinosarcoma, Int. J. Appl. Radiat. Isot., 36, 339, 10.1016/0020-708X(85)90272-8 Bolster, 1985, Synthesis of carbon-11 labelled ornithine and lysine. Preliminary accumulation studies in rats with Walter 256 carcinosarcoma, Int. J. Appl. Radiat. Isot., 36, 263, 10.1016/0020-708X(85)90082-1 Bolster, 1986, A new method for the labeling of peptides with carbon-11, 30 Bolster, 1986, The preparation of 11C-carboxylic labeled l-methionine for measuring protein synthesis in rats, 49 Brown, 1968, Reaction of carbon monoxide at atmospheric pressure with trialkyl-boranes in the presence of lithium trimethoxyaluminohydride. A convenient procedure for the conversion of olefins into aldehydes by hydroboration, J. Am. Chem. Soc., 90, 499, 10.1021/ja01004a055 Brown, 1969, Organoborane-carbon monoxide reactions. A new versatile approach to the synthesis of carbon structures, Acc. Chem. Res., 2, 65, 10.1021/ar50015a001 Brown, 1969, Reaction of β-alkyl-9-borabicyclo [3.3.1] nonanes with carbon monoxide in the presence of lithium trimethoxyaluminohydride, J. Am. Chem. Soc., 91, 2144, 10.1021/ja01036a068 Calvin, 1949, 262 Casey, 1981, Preparation and preliminary tissue studies of optically active 11C-D and l-phenylalanine, Int. J. Appl. Radiat. Isot., 32, 325, 10.1016/0020-708X(81)90093-4 Cohen, 1978, Enzymatic synthesis of (11C) pyruvic acid lactic acid and l-alanine, J. Nucl. Med., 19, 701 Cohen, 1980, Enzymatic synthesis of 11C-pyruvic acid and 11C-lactic acid, Int. J. Appl. Radiat. Isot., 31, 45, 10.1016/0020-708X(80)90229-X Dannals, 1985, Radiosynthesis of an opiate receptor binding radiotracer, [11C]carfentanil, Int. J. Appl. Radiat. Isot., 36, 303, 10.1016/0020-708X(85)90089-4 DeGrazia, 1975, Radioscintigraphic studies of 11C distribution in cats of 1-11C-ethanol, J. Nucl. Med., 16, 73 Dence, 1984, Remote system for production of carbon-11 labeled glucose via photosynthesis, J. Labelled Compd. Radiopharm., 21, 743, 10.1002/jlcr.2580210808 Ehrin, 1980, A convenient method for the preparation of 11C-labelled glucose, J. Labelled Compd. Radiopharm., 17, 453, 10.1002/jlcr.2580170316 Ehrin, 1983, [11C]Labeled glucose and its utilization in positron emission tomography, J. Nucl. Med., 24, 326 Elmaleh, 1984, Structure localization relationship of different chain length l-[11C]-labeled betamethyl fatty acids, J. Labelled Compd. Radiopharm., 21, 1203 Elmaleh, 1982, Beta-methyl [1-11C]heptadecanoic acid: A new myocardial metabolic tracer for positron emission tomography, J. Nucl. Med., 23, 169 Farde, 1986, Quantitative analysis of D2 dopamine receptor binding in the living human brain by PET., Science, 231, 258, 10.1126/science.2867601 Finn, 1984, Synthesis with isotopically labelled carbon. Methyl iodide formaldehyde and cyanide, Int. J. Appl. Radiat. Isot., 35, 323, 10.1016/0020-708X(84)90036-X Fowler, 1976, Carbon-11 labeled aliphatic amines in lung uptake and metabolism studies, potential for dynamic measurements In vivo, J. Pharmacol. Exp. Ther., 198, 456 Fowler, 1982 Fowler, 1986, 391 Gatley, 1979, Synthesis of 11C-hippuric acid from 11C-benzoic acid and glycine using rat-liver mitochondria, J. Labelled Compd. Radiopharm., 16, 182 Gatley, 1973, Relationship of chemical structure to in vivo scintigraphic distribution pattern of 11C-carboxylates, J. Nucl. Med., 14, 747 Gelbard, 1981, Biosynthetic methods for incorporating positron-emitting radionuclides into compounds of biomedical interest, J. Labelled Compd. Radiopharm., 18, 933, 10.1002/jlcr.2580180703 Goulding, 1973, Aspects of the preparation of carbon-11 labeled glucose, Int. J. Appl. Radiat. Isot., 24, 7, 10.1016/0020-708X(73)90052-5 Grierson, 1984, Solid phase synthesis of 11C-labelled compounds, J. Labelled Compd. Radiopharm., 21, 1174 Halldin, 1984, Asymmetric synthesis of l-[3-11C]phenylalanine using chiral hydrogenation catalysts, Int. J. Appl. Radiat. Isot., 35, 945, 10.1016/0020-708X(84)90207-2 Halldin, 1984, Synthesis of racemic[3-11C]phenyl-alanine [3-11C]DOPA, Int. J. Appl. Radiat. Isot., 35, 779, 10.1016/0020-708X(84)90086-3 Halldin, 1984, Synthesis of [11C]labelled aldehydes, Acta Chem. Scand. B., 38, 1, 10.3891/acta.chem.scand.38b-0001 Halldin, 1979, 11C-Labeled octanal and benzaldehyde, J. Labelled Compd. Radiopharm., 16, 435, 10.1002/jlcr.2580160309 Halldin, 1984, Synthesis of 2-or 3-11C-labeled aromatic amino acids, J. Labelled Compd. Radiopharm., 31, 1178 Hara, 1971, l-Aspartic acid-4-11C as a tumor scanning agent, J. Nucl. Med., 12, 361 Inoue, 1982 Iwata, 1979, A remote-controlled synthesis of 11C-iodomethane for the practical preparation of 11C-labelled radiopharmaceuticals, Int. J. Appl. Radiat. Isot., 30, 194, 10.1016/0020-708X(79)90134-0 Jewett, 1985, A captive solvent method for rapid radiosynthesis Application to the synthesis of [1-11C]palmitic acid, Int. J. Appl. Radiat. Isot., 36, 672, 10.1016/0020-708X(85)90011-0 Jewett, 1981, 407 Jewett, 1981, Preparation of carbon-11 labelled acetate palmitic acid for the study of myocardial metabolism by emission-computerized axial tomography, J. Radioanal. Chem., 64, 291, 10.1007/BF02518360 Jewett, 1982, [l-11C]Palmitic acid, improved radiopharmaceutical preparation, Int. J. Appl. Radiat. Isot., 33, 1471, 10.1016/0020-708X(82)90189-2 Kamen, 1951, Radioactive Tracers in Biology, 224 Kilbourn, 1982, No-carrier-added synthesis of [l-11C]pyruvic acid, Int. J. Appl. Radiat. Isot., 33, 359, 10.1016/0020-708X(82)90149-1 Kilbourn, 1983, Synthesis of carbon-11 labeled amides via carbonylation of lithium dialkylamides, 861 Kilbourn, 1984, Synthesis of dl-[3-11C]phenylalanine, Int. J. Appl. Radiat. Isot., 35, 603, 10.1016/0020-708X(84)90103-0 Halldin, 1979, 11C-Labeled octanal and benzaldehyde, J. Labelled Compd. Radiopharm., 16, 435, 10.1002/jlcr.2580160309 Knapp, 1985, 11C-Butanol for imaging of the blood-flow distribution in tumor-bearing animals, Eur. J. Nucl. Med., 10, 540, 10.1007/BF00252749 Kothari, 1985, l-[11C]Butanol: synthesis and development as a radiopharmaceutical for blood flow measurements, Int. J. Appl. Radiat Isot., 36, 412, 10.1016/0020-708X(85)90285-6 Kothari, 1985, 11C-Butanol for imaging of the blood-flow distribution in tumor-bearing animals, Eur. J. Nucl. Med., 10, 540 Landais, 1987, A new synthesis of carbon-11 labelled phosgene, Appl. Radiat. Isot., 38, 297, 10.1016/0883-2889(87)90042-6 Langstrom, 1976, The preparation of 11C-methyl iodide its use in the synthesis of 11C-methyl-l-methionine, Int. J. Appl. Radiat. Isot., 27, 357, 10.1016/0020-708X(76)90088-0 Langstrom, 1986, The synthesis of l-11C-labelled ethyl, propyl, butyl and isobutyl iodides and examples of alkylation reactions, Appl. Radiat. Isot., 37, 1141, 10.1016/0883-2889(86)90140-1 Lifton, 1971, Preparation of glucose labeled with 20-minute half-lived carbon-11, Radiat. Res., 45, 35, 10.2307/3573077 Linvi, 1982, Beta-methyl [l-11C]heptadecanoic acid: A new myocardial metabolic tracer for positron emission tomography, J. Nucl. Med., 23, 169 Machulla, 1976, Radioanalytical quality control of 11C 18F and 123I-labeled compounds and radiopharmaceuticals, J. Radioanal. Chem., 32, 381, 10.1007/BF02517513 Machulla, 1979, 11C-labelled radiopharmaceuticals Synthesis and high pressure liquid chro-matography of nicotinic-11C-acid amide, J. Labelled Compd. Radiopharm., 16, 287, 10.1002/jlcr.2580160208 Matsumoto, 1973, A new synthesis of α-amino acids, J. Org. Chem., 38, 2094, 10.1021/jo00951a030 Mullen, 1980, 243 Myers, 1985, Formamidines as precursors to α-amino carbanions and their application to asymmetric C-C bond-forming reactions, Aldrichim. Acta, 18, 59 Nahinsky, 1942, Tracer studies with radioactive carbon. The synthesis and oxidation of several three carbon acids, J. Am. Chem. Soc., 64, 2299, 10.1021/ja01262a023 Narayana, 1985, Organic synthesis via carbonylation of organometallic reagents with carbon monoxide, Synthesis, 253, 10.1055/s-1985-31170 Oberdorfer, 1985, A new procedure for the preparation of 11C-labelled methyl iodide, Int. J. Appl. Radiat. Isot., 36, 435, 10.1016/0020-708X(85)90205-4 Padgett, 1982, [l-11C]Palmitic acid, improved radiopharmaceutical preparation, Int. J. Appl. Radiat. Isot., 33, 1471, 10.1016/0020-708X(82)90189-2 Palmer, 1974, Biosynthetic preparation of 11C-labeled galactose glycerol mannitol, J. Labelled Compd. Radiopharm., 10, 627, 10.1002/jlcr.2590100412 Phelps, 1985, Positron emission tomography: Human brain function and biochemistry, Science, 228, 799, 10.1126/science.2860723 Pike, 1981, Preparation of 11C-labeled acetate for study of myocardial metabolism by emission computed axial tomography, J. Labelled Compd. Radiopharm., 18, 249 Pike, 1981, Preparation of carbon-11 labelled acetate palmitic acid for the study of myocardial metabolism by emission-computerized axial tomography, J. Radioanal. Chem., 64, 291, 10.1007/BF02518360 Pike, 1982, Preparation of [11C]acetate—an agent for the study of myocardial metabolism by positron emission tomography, Int. J. Appl. Radiat Isot., 33, 505, 10.1016/0020-708X(82)90003-5 Pike, 1984, The remotely-controlled preparation of a 11C-labeled radiopharmaceutical-[l-11C]acetate, Int. J. Appl. Radiat. Isot., 35, 623, 10.1016/0020-708X(84)90107-8 Pike, 1951, Radioactive Tracers in Biology, 224 Pike, 1973, Relationship of chemical structure to in vivo scintigraphic distribution pattern of 11C-carboxylates, J. Nucl. Med., 14, 747 Pike, 1981, Preparation of 11C-labeled acetate for study of myocardial metabolism by emission computed axial tomography, J. Labelled Compd. Radiopharm., 18, 249 Pike, 1982, Preparation of [11C]acetate—an agent for the study of myocardial metabolism by positron emission tomography, Int. J. Appl. Radiat Isot., 33, 505, 10.1016/0020-708X(82)90003-5 Poe, 1973, Myocardial extraction of various labeled fatty acids carboxylates, J. Nucl. Med., 14, 440 Raichle, 1976, Blood-brain barrier permeability of 11C labeled alcohols and 15O labeled water, Am. J. Physiol., 230, 543, 10.1152/ajplegacy.1976.230.2.543 Raichle, 1979, Quantitative in vivo autoradiography with positron emission tomography, Brain Res. Rev., 1, 47, 10.1016/0165-0173(79)90016-X Ram, 1984, Synthesis of 11C-amino acids using 11C-carbon dioxide for tomographic measurement of protein synthesis in the human brain Ram, 1984, A general procedure for mild rapid reduction of aliphatic and aromatic nitro compounds using ammonium formate as a catalytic hydrogen transfer agent, Tetrahedron Lett., 25, 3415, 10.1016/S0040-4039(01)91034-2 Ram, 1985, Rapid reductive carboxylation of secondary amines. A new synthesis of tertiary N-methylated amines, Tetrahedron Lett., 26, 5367, 10.1016/S0040-4039(00)98209-1 Ram, 1986, A facile synthesis of α-amino esters via reduction of a nitro esters using ammonium formate as a catalytic hydrogen transfer agent, Synthesis, 133, 10.1055/s-1986-31497 Ram, 1986, Rapid reductive-carboxylation of secondary amines. One pot synthesis of N′-(4-11C-methyl) imipramine, Appl. Radiat. Isot., 37, 391, 10.1016/0883-2889(86)90094-8 Ram, S.; Ehrenkaufer, R. E.; Unpublished results; 1987a. Ram, 1987, Synthesis of [11C]labeled dopamine (D1) antagonist 3-N-[11C]methyl benzazepines using [11C]CO2., J. Nucl. Med., 28, 625 Rautenstrauch, 1979, Carbonylation of lithium dialkylamides to give carboamoyllithiums, Angew. Chem. Int. Ed. Engl., 18, 83, 10.1002/anie.197900832 Reiffers, 1977, Rapid Synthesis and purification of carbon-11 labeled DOPA: a potential agent for brain studies, Int. J. Appl. Radiat. Isot., 28, 955, 10.1016/0020-708X(77)90060-6 Robinson, 1973, Biological dynamics of 18F 11C-labeled carboxylates and alcohols, J. Nucl. Med., 14, 446 Slegers, 1986, Synthesis of [1-11C]iodoethane for the preparation of [11C]ethyl labelled radiopharmaceuticals, 37, 279 Slegers, 1973, Myocardial extraction of various labeled fatty acids carboxylates, J. Nucl. Med., 14, 440 Slegers, 1973, Biological dynamics of 18F 11C-labeled carboxylates and alcohols, J. Nucl. Med., 14, 446 Slegers, 1975, Radioscintigraphic studies of 11C distribution in cats of 1-11C-ethanol, J. Nucl. Med., 16, 73 Slegers, 1976, Blood-brain barrier permeability of 11C labeled alcohols and 15O labeled water, Am. J. Physiol., 230, 543, 10.1152/ajplegacy.1976.230.2.543 Sneeden, 1969, 137 Spolter, 1975, Combined chemical and enzymatic synthesis of [11C]acetyl phosphate, J. Nucl. Med., 16, 572 Spolter, 1976, Enzymatic synthesis of [11C]citric acid, J. Nucl. Med., 17, 558 Spolter, 1979, Enzymatic synthesis of [11C]acetylcarnitine, J. Nucl. Med., 20, 662 Straatmann, 1973, The liquid Chromatographic purification of carbon-11 labeled glucose, Int. J. Appl. Radiat. Isot., 24, 234, 10.1016/0020-708X(73)90047-1 Tang, 1979, 11C-Labeled octanal and benzaldehyde, J. Labelled Compd. Radiopharm., 16, 435, 10.1002/jlcr.2580160309 Vaalburg, 1972, (Rapid synthesis of α-phenylglycine by carboxylation of α-lithiobenzylisocyanide, Synth. Comm., 2, 423, 10.1080/00397917208081791 Vaalburg, 1976, Preparation of carbon-11 labeled phenylalanine phenylglycine by a new amino acid synthesis, Int. J. Appl. Radiat. Isot., 27, 153, 10.1016/0020-708X(76)90126-5 Vaalburg, 1972, (Rapid synthesis of α-phenylglycine by carboxylation of α-lithiobenzylisocyanide, Synth. Comm., 2, 423, 10.1080/00397917208081791 Vaalburg, 1984, Carbon-11 labelled tyrosine for investigation of tumor metabolism by positron emission tomography, J. Labelled Compd. Radiopharm., 21, 1177 Vandewalle, 1985, Fully automatic microprocessor-controlled system for the production of 11CO211CH3I and 11C-labeled radio-pharmaceuticals, Int. J. Appl. Radiat. Isot., 36, 469, 10.1016/0020-708X(85)90211-X Wagner, 1986, Quantitative imaging of neuroreceptors in the living human brain, 16, 51 Washburn, 1982, Production of l-[1-11C]valine by HPLC resolution, J. Nucl. Med., 23, 29 Weimer, 1973, Development of fast syntheses of amino acids and fatty alcohols with carbon-11 Welch, 1981, 407 Welch, 1985, Remote system for production of carbon-11 labeled palmitic acid, J. Labelled Compd. Radiopharm., 20, 1087, 10.1002/jlcr.2580200906 Winstead, 1973, Relationship of chemical structure to in vivo scintigraphic distribution pattern of 11C-carboxylates, J. Nucl. Med., 14, 747 Winstead, 1942, Tracer studies with radioactive carbon. The synthesis and oxidation of several three carbon acids, J. Am. Chem. Soc., 64, 2299, 10.1021/ja01262a023 Wolf, 1971, The preparation of radiopharmaceuticals containing isotopes of short half life, Radioisotopy, 4, 499