[en] Four new tertiary amines: bis(3-N,N-dimethyl aminopropyl)selenide (PROMOSE), bis(3-N-(morpholino)propyl)selenide, N-methyl-selenomorpholine and N-phenyl-selenomorpholine structurally related to MOSE proposed by Kung and Blau, have been labeled through a radiochemical procedure suitable for both 75Se and 73Se. The radiochemical yields of the carrier added synthesis ranged between 64 and 85% for the four 75Se labelings and was 64% EOB time corrected for [73Se]PROMOSE. The chemical and radiochemical purities were higher than 99% after chromatographic purifications. The n-octanol/phosphate buffer partition coefficients (P) were measured at various pH (6.5-8) for each compound and the tissue distributions of PROMOSE in rats were also carried out. The experimental results showed a good correlation between the P = f(pH) function and the in vivo behaviour of the considered compound. PROMOSE was selected for further investigations as a brain pH indicator.
Research Center/Unit :
GIGA CRC (Cyclotron Research Center) In vivo Imaging-Aging & Memory - ULiège
Disciplines :
Radiology, nuclear medicine & imaging
Author, co-author :
Plenevaux, Alain ; Université de Liège - ULiège > Centre de recherches du cyclotron
Cantineau, Robert
Brihaye, Claude
Lemaire, Christian ; Université de Liège - ULiège > Centre de recherches du cyclotron
Christiaens, Léon
Guillaume, Marcel
Language :
English
Title :
Synthesis and tissue distribution of four Se-labeled tertiary amines, potential brain pH imaging agents.
Publication date :
1990
Journal title :
International Journal of Radiation Applications and Instrumentation. Part B, Nuclear Medicine and Biology
Arnold, Junck, Rottenberg (1985) In vivo measurement of regional brain and tumor pH using [14C]dimethyl-oxazolidinedione and quantitative autoradiography. J. Cereb. Blood Flow Metab. 5:369-375.
Budinger (1981) Revival of clinical nuclear medicine brain imaging. J. Nucl. Med. 22:1094-1097.
Buxton, Wechsler, Alpert, Ackerman, Elmaleh, Correia (1984) Measurement of brain pH using 11CO2 and positron emission tomography. J. Cereb. Blood Flow Metab. 4:8-16.
Cillufo, Anderson, Michenfelder, Sundt (1982) Cerebral blood flow, brain pH and oxidative metabolism in the cat during severe insulin induced hypoglycemia. J. Cereb. Blood Flow Metab. 2:337-346.
Cloutier, Watson, Rohrer, Smith (1973) Calculating the radiation dose to an organ. J Nucl Med 14:53-55.
Coffey, Cristy, Wagner (1981) Specified absorbed fraction for photon sources uniformly distributed in the heart chambers and heart wall of a heterogeneous phantom. J. Nucl. Med. 22:65-71.
Coleman, Drayer, Jaszczak (1982) Studying regional brain function: A challenge for SPECT. J. Nucl. Med. 23:266-270.
Dischino, Welch, Kilbourn, Raichle (1983) Relationship between lipophilicity and brain extraction of C-11-labeled radiopharmaceuticals. J. Nucl. Med. 24:1030-1038.
Eckerman, Cristy, Wagner (1980) Dosimetric evaluation of brain scanning agents. Proc. of 3rd Int. Radiopharm. Dosimetry Symp. , E.E. Watson, A.T. Schafke-Stelson, J.L. Coffey, R.J. Cloutier, Oak Ridge, HHS Publication FDA 81-8166, Department of Health and Human Services, Rockville, Md; 527-540.
Ginos, Tilbury, Haber, Rottenberg (1982) Synthesis of [2-11C]5, 5-dimethyl-2,4-oxazolidinedione for studies with positron tomography. J. Nucl. Med. 23:255-258.
Gladysz, Hornby, Garbe (1978) A convenient one-flask synthesis of dialkyl selenides and diselenides via lithium triethylborohydride reduction of Se. J. Org. Chem. 43:1204-1208.
Hill (1980) Single-photon emission computed tomography to study cerebral function in man. J. Nucl. Med. 21:1197-1199.
Holm, Andersen, Vorstrup, Lassen, Paulson, Holmes (1985) Dynamic SPECT of the brain using a lipophilic technetium-99m complex, PnAO. J. Nucl. Med. 26:1129-1134.
ICRP (1977) Recommendations of the International Commission on Radiobiological Protection. Publication 26 21-22.
Kearfott, Junck, Rottenberg (1983) C-11 Dimethyl-oxazolidinedione (DMO): biodistribution, radiation absorbed dose, and potential for PET measurement of regional brain pH: concise communication. J. Nucl. Med. 24:805-811.
Kim, Handa, Ishikawa, Hirai, Yoshida, Imadaka (1985) Brain tissue acidosis and changes of energy metabolism in mild incomplete ischemia-Topographical study. J. Cereb. Blood Flow Metab. 5:432-438.
Kocher Radioactive Decay Data Tables, J.S. Smith, Technical Information Center U.S. DOE, Springfield, Va; 1981.
Kogure, Busto, Schwartzman, Scheinberg (1980) The dissociation of cerebral blood flow, metabolism and function in the early stages of developing cerebral infarction. Ann. Neurol. 8:278-290.
Kuhl, Barrio, Huang (1982) Quantifying local cerebral blood flow by N-isopropyl-p-[123I]iodo-amphetamine (IMP) tomography. J. Nucl. Med. 23:196-203.
Kung, Blau (1980) Synthesis of selenium-75 labeled tertiary diamines: New brain imaging agents. J. Med. Chem. 23:1127-1130.
Kung, Blau (1980) Regional intracellular pH shift: A proposed new mechanism for radiopharmaceutical uptake in brain and other tissues. J. Nucl. Med. 21:147-152.
Kung, Tramposch, Blau (1983) A new brain perfusion imaging agent: [123I]HIPDM: N, N, N′- trimethyl-N′-[2-hydroxy-3-methyl-5-iodobenzyl]-1, 3-pro-panediamine. J. Nucl. Med. 24:66-72.
Kung, Molnar, Billings, Wicks, Blau (1984) Synthesis and biodistribution of neutral lipid-soluble Tc-99m complexes that cross the blood-brain-barrier. J. Nucl. Med. 25:326-332.
Loevinger, Berman (1976) A revised shema for calculating the absorbed dose from biologically distributed radio-nuclides. MIRD Pamphlet No. 1 , J. Nucl. Med., (revised 1976); 7-14.
Mabe, Blomqvist, Siesjö (1983) Intracellular pH in the brain following transient ischemia. J. Cereb. Blood Flow Metab. 3:109-114.
Meyer, Anderson, Sundt, Yaksh (1986) Intracellular brain pH, indicator tissue perfusion, electroencephalography, and histology in severe and moderate focal cortical ischemia in rabbit. J. Cereb. Blood Flow Metab. 6:71-78.
Oldendorf (1974) Lipid solubility and drug penetration of the blood-brain-barrier. (38444). Proc. Soc. Exp. Biol. Med. 147:813-816.
Oldendorf (1978) Need for new radiopharmaceuticals. J. Nucl. Med. 19:1182.
Pelligrino, Siesjö (1981) Regulation of extra- and intra-cellular pH in the brain in severe hypoglycemia. J. Cereb. Blood Flow Metab. 1:85-96.
Plenevaux, Guillaume, Brihaye, Cantineau (1990) Chemical processing for production of no-carrier added selenium-73 from germanium and arsenic targets and synthesis of l-2-amino-4-([73Se]methylseleno)butyric acid (l-[73Se]Selenomethionine). Appl. Radiat. Isot. , In press; 41.
Plum (1983) What causes infarction in ischemic brain? The Robert Wartenberg Lecture. Neurology 33:222-233.
Raichle, Grubb, Higgins (1979) Measurement of brain tissue carbon dioxide content in vivo by emission tomography. Brain Res. 166:413-417.
Rossotti, Rossotti The Determination of Stability Constants, McGraw-Hill, New York; 1961.
Rottenberg, Ginos, Kearfott, Junck, Conti, Dhawan (1982) Feasibility of measuring regional brain tissue pH using 11C-dimethyloxazolidine-dione and positron emission tomography. Preliminary observations in animals and man. Workshop on Time-of-Flight Tomography , IEEE Computer Society, Silver Spring, Md; 15-18.
Siesjö Brain Energy Metabolism, Wiley, Chichester; 1978.
Snyder, Ford, Warner (1978) Estimates of specific absorbed fraction for monoenergetic photon sources uniformly distributed in various organs of a heterogeneous phantom. MIRD Pamphlet No. 5 , J. Nucl. Med., (revised 1978); 16-17.
Syrota, Samson, Boullais (1985) Tomographic mapping of the brain intracellular pH and extracellular water space in stroke patients. J. Cereb. Blood Flow Metab. 5:358-368.
Tramposch, Kung, Blau (1983) Radioiodine-labeled N,N-dimethyl-N'-(2-hydroxy-3-alkyl-5-iodoben-zyl)-1,3-propanediamines for brain perfusion imaging. J. Med. Chem. 26:121-125.
Troutner, Volkert, Hoffman, Holmes (1984) A neutral lipophilic complex of Tc-99m with a multidentate amine oxime. Int. J. Appl. Radiat. Isot. 35:467-470.
Volkert, Hoffman, Seger, Troutner, Holmes (1984) 99mTc-propylene amine oxime (99mTc-PnAO), a potential brain radiopharmaceutical. Eur. J. Nucl. Med. 9:511-516.
Wicks, Kung, Ackerhalt, Steinback, Blau (1980) Radiation dose to humans from 75Se-MOSE pH shift brain imaging agent. Proc. 3rd Int. Radiopharm. Dosimetry Symp. , E.E. Watson, A.T. Schafke-Stelson, J.L. Coffey, R.J. Cloutier, Oak Ridge, HHS Publication FDA 81-8166, U.S. Department of Health and Human Services, Rockville, Md; 541-545.
