N-[18F]fluoroethylpiperidinyl, N-[18F]fluoroethylpiperidinemethyl and N-[18F]fluoroethylpyrrolidinyl esters as radiotracers for acetylcholinesterase

Nuclear Medicine and Biology

Volumn 30, Issue 5, 2003, Pages 491-500

  Shao, Xia ^a   Butch, Elizabeth R ^b   Kilbourn, Michael R ^a   Snyder, Scott E ^a  

^a UNIVERSITY OF MICHIGAN HEALTH SYSTEM   (United States)

^b EASTERN MICHIGAN UNIVERSITY   (United States)

Author keywords

Acetylcholinesterase; Alzheimer's disease; Emission computed; Fluorine 18; Tomography

Indexed keywords

ACETYLCHOLINESTERASE; BRAIN ENZYME; CHOLINESTERASE; FUNCTIONAL GROUP; METHYL GROUP; N FLUOROETHYL 2 PIPERIDINEMETHYLACETATE F 18; N FLUOROETHYL 2 PIPERIDINEMETHYLPROPIONATE F 18; N FLUOROETHYL 3 PYRROLIDINYLACETATE F 18; N FLUOROETHYL 4 PIPERIDINYLACETATE F 18; N FLUOROETHYL 4 PIPERIDINYLPROPIONATE F 18; PIPERIDINE DERIVATIVE; PYRROLIDINE DERIVATIVE; TRACER; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BLOOD; CONTROLLED STUDY; DRUG DISTRIBUTION; DRUG METABOLISM; DRUG SCREENING; DRUG SELECTIVITY; DRUG SYNTHESIS; ENZYMATIC DEGRADATION; ENZYME ACTIVITY; FEMALE; IN VITRO STUDY; MALE; MOUSE; NONHUMAN; POSITRON EMISSION TOMOGRAPHY; RAT; TIME;

EID: 0038771226     PISSN: 09698051     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0969-8051(03)00031-3     Document Type: Article

References (29)

1. Beckett A.H., Harper N.J., Clitherow J.W. The importance of stereoisomerism in muscarinic activity. J. Pharm. Pharmacol. 15:1963;362-371.
2. Bierer L.M., Haroutunian V., Gabriel S., Knoott P.J., Carlin L.S., Purohit D.P., Perl D.P., Schmeidler J., Kanof P., Davis K.L. Neurochemical correlates of dementia severity in Alzheimer's disease relative importance of cholinergic deficits . J. Neurochem. 64:1995;749-760.
3. Frey K.A., Koeppe R.A., Kilbourn M.R., Snyder S.E., Kuhl D.E. PET quantification of cortical acetylcholinesterase inhibition in monkey and human. J. Nucl. Med. 38:1997;146P.
4. Irie T., Fukushi K., Akimoto Y., Tamagami H., Nozaki T. Design and evaluation of radioactive acetylcholine analogs for mapping brain acetylcholinesterase (AChE) in vivo. Nucl. Med. Biol. 21:1884;801-808.
5. Irie T., Fukushi K., Ikota N., Namba H., Iyo M., Nagatsuka S. Radioactive N-methylpiperidyl-3-esters for in vivo measurement of acetylcholinesterase (AChE) in the brain optical resolution, enzymatic properties and in vivo response . J. Lab. Comp. Radiopharm. 37:1997;214-216.
6. Irie T., Fukushi K., Namba H., Iyo M., Tamagami H., Hagatsuka S.-I., Ikota N. Brain acetylcholinesterase activity validation of a PET tracer in rat model of Alzheimer's disease . J. Nucl. Med. 37:1996;649-655.
7. Iyo M., Namba H., Fukushi K., Shinotoh H., Hagatsuka S., Suhara T., Sudo Y., Suzuki K., Irie T. Measurement of acetylcholinesterase by positron emission tomography in the brains of healthy controls and patients with Alzheimer's disease. Lancet. 349:1997;1805-1809.
8. Kadner S.S., Katz J., Berliner B.A., Levitz M., Finlay T.H. Hormonally sensitive esterase activity in the mouse uterus results from uptake of plasma esterase. Endocrinology. 115:1984;2406-2417.
9. S.S. Kadner, J. Katz, M. Levitz, T.H. Finlay, The 65-kDa phorbol-diester hydrolase in mouse plasma is esterase 1 and is immunologically distinct from the 56-kDa phorbol-diester hydrolase in mouse liver, 260 (1985) 15604-15609.
10. Kikuchi T., Fukushi K., Ikota N., Ueda T., Nagatsuka S., Arano Y., Irie T. Synthesis of piperidinyl and pyrrolidinyl butyrates for potential in vivo measurement of cerebral butyrylcholinesterase activity. J. Lab. Comp. Radiopharm. 44:2001;31-41.
11. 11C]PMP). Synapse. 22:1996;123-131.
12. 11C]Methylpiperidine esters as acetylcholinesterase substrates an in vivo structure-activity study . Nucl. Med. Biol. 25:1998;755-760.
13. Kilbourn M.R., Sherman P.S., Snyder S.E. Simplified methods for in vivo measurement of acetylcholinesterase activity in rodent brain. Nucl. Med. Biol. 26:1999;543-550.
14. Koeppe R.A., Frey K.A., Snyder S.E., Kilbourn M.R., Kuhl D.E. Evaluation of two distinct kinetic analyses for use PMP an irreversible tracer for mapping AChE activity . J. Cereb. Blood Flow Metab. 17:1997;S329.
15. 11C]methylpiperidin-4-yl propionate (PMP) to constrain or not to constrain? J. Nucl. Med. 38:1997;198P.
16. 11C]methylpiperidin-4-yl propionate Alternatives for analysis of an irreversible positron emission tomography tracer for measurement of acetylcholinesterase activity in human brain . J. Cereb. Blood Flow Metab. 1:1999;1150-1163.
17. Kuhl D.E., Koeppe R.A., Minoshima S., Snyder S.E., Ficaro E.P., Foster N.L., Frey F.A., Kilbourn M.R. In vivo mapping of cerebral acetylcholinesterase activity in aging and Alzheimer's disease. Neurology. 52:1999;691-699.
18. Kuhl D.E., Minoshima S., Frey F.A., Foster N.L., Kilbourn M.R., Koeppe R.A. Limited donepezil inhibition of acetylcholinesterase measured with positron emission tomography in living Alzheimer cerebral cortex. Ann Neurol. 48:2000;391-395.
19. Mannhold R., Rekker R.F. The hydrophobic fragmental constant approach for calculating log P in octanol/water and aliphatic hydrocarbon/water systems. Perspect. Drag Discov. Des. 18:2000;1-18.
20. Namba H., Irie T., Fukushi K., Iyo M. In vivo measurement of acetylcholinesterase activity in the brain with a radioactive acetylcholine analog. Brain Res. 667:1994;278-282.
21. Namba H., Iyo M., Fukushi K., Shinotoh H., Hagatsuka S., Suhara T., Sudo Y., Suzuki K., Irie T. Human cerebral acetylcholinesterase activity measured with positron emission tomography procedure, normal values and effect of age . Eur. J. Nucl. Med. 26:1999;135-143.
22. Otto J., Ronai A., Deimling O.V. Purification and characterization of esterase 1F, the albumin esterase of the house mouse. Eur. J. Biochem. 116:1981;285-291.
23. Shao, X., Lisi, J.M., Butch, E.R., Kilbourn, M.R., Snyder, S.E. N-Methylpiperidinemethyl, N-methylpyrrolidinyl, N-methylpyrrolidinemethyl esters as PET radiotracers for acetylcholinesterase activity, Nucl. Med. Biol. in press.
24. Shinotoh H., Namba H., Fukushi K., Nagatsuka S.-L., Tanaka N., Aotsuka A., Tanada S., Irie T. Brain acetylcholinesterase activity in Alzheimer's disease measuredby positron emission tomography. Alzheimer Dis. Assoc. Disord. 14:2000;S114-S118.
25. 11C]PMP) for in vivo measurements of acetylcholinesterase activity. Nucl. Med. Biol. 25:2000;751-754.
26. Snyder S.E., Bryan T., Gunupudi N., Butch E.R., Kilbourn M.R. Do in vitro enzyme kinetics predict in vivo radiotracer kinetics? Gjedde A. Physiological Imaging of the Brain with PET. 2000;105-108 Academic Press, San Diego, CA.
27. Snyder S.E., Gunupudi N., Sherman P.S., Butch E.R., Skaddan M.B., Kilbourn M.R., Koeppe R.A., Kuhl D.E. Radiolabeled cholinesterase substrates in vitro methods for determining structure-activity relationships and identification of a positron emission tomography radiopharmaceutical for in vivo measurement of butyrylcholinesterase activity . J. Cereb. Blood Flow Metab. 21:2001;132-143.
28. Volkow N.D., Ding Y.S., Fowler J.S., Gatly S.J. Imaging brain cholinergic activity with positron emission tomography its role in the evaluation of cholinergic treatments in Alzheimer's dementia . Biol. Psychiatry. 49:2001;211-220.
29. 18F]FEtP4A, a promising PET tracer for mapping acetylcholinesterase in vivo. Nucl. Med. Biol. 29:2002;463-468.