Syntheses and biological evaluation of 18F-labeled 3-(1-benzyl- piperidin-4-yl)-1-(1-methyl-1H-indol-3-yl)propan-1-ones for in vivo mapping of acetylcholinesterase

Nuclear Medicine and Biology

Volumn 27, Issue 3, 2000, Pages 263-267

  Choe, Yearn Seong ^a   Oh, Seung Jun ^a   Shim, Insop ^a   Naruto, Shunji ^b   Chi, Dae Yoon ^c   Kim, Sang Eun ^a   Lee, Kyung Han ^a   Choi, Yong ^a   Kim, Byung Tae ^a  

^a Samsung Medical Center   (South Korea)

^b DAIICHI SANKYO CO   (Japan)

^c Inha University   (South Korea)

Author keywords

18F; Acetylcholinesterase; Acetylcholinesterase inhibitor; Alzheimer's disease

Indexed keywords

3 [1 (3 FLUOROMETHYLBENZYL) PIPERIDIN 4 YL] 1 (1 METHYL 1H INDOLE 3 YL)PROPAN 1 ONE; 3 [1 (4 FLUOROBENZYL)PIPERIDIN 4 YL] 1 (1 METHYL 1H INDOLE 3 YL)PROPAN 1 ONE; 3 [1 (4 FLUOROMETHYLBENZYL) PIPERIDIN 4 YL] 1 (1 METHYL 1H INDOLE 3 YL)PROPAN 1 ONE; ACETYLCHOLINESTERASE; CHOLINESTERASE INHIBITOR; FLUORINE 18; UNCLASSIFIED DRUG;

ALZHEIMER DISEASE; ANIMAL EXPERIMENT; ARTICLE; CHOLINERGIC SYSTEM; CHOLINESTERASE INHIBITION; DEMENTIA; ENZYME INHIBITION; ISOTOPE LABELING; MALE; MOUSE; NONHUMAN; POSITRON EMISSION TOMOGRAPHY; RADIOACTIVITY; SINGLE PHOTON EMISSION COMPUTER TOMOGRAPHY; TISSUE DISTRIBUTION;

ACETYLCHOLINESTERASE; ANIMALS; BIOTRANSFORMATION; BRAIN; BRAIN MAPPING; CHOLINESTERASE INHIBITORS; DRUG STABILITY; FLUORINE RADIOISOTOPES; INDOLES; MALE; MICE; MICE, INBRED ICR; PIPERIDINES; RADIOPHARMACEUTICALS; TISSUE DISTRIBUTION;

EID: 0011719537     PISSN: 09698051     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0969-8051(00)00086-X     Document Type: Article

References (17)

1. 11C]Physostigmine . J. Labelled Compd. Radiopharm. 33:1993;277-284.
2. 11C]methoxy-3-[2-[1-(phenylmethyl)-4-piperidinyl]ethyl]-1,2- benzisoxazole as an in vivo radioligand for acetylcholinesterase. Nucl. Med. Biol. 26:1999;99-103.
3. 18F]fluoromethylbenzylation of amides and amines . Appl. Radiat. Isot. 49:1998;73-77.
4. Davies P., Maloney A.J.F. Selective loss of central cholinergic neurons in Alzheimer's disease. Lancet. 2:1976;1403.
5. 11C]6-dimethoxy-1-oxoindan-2-yl)methyl]piperidine A promising ligand for visualization of acetylcholinesterase by PET . J. Labelled Compd. Radiopharm. 42S:1999;434-436.
6. Geula C., Mesulam M.M. Cholinergic systems and related neuropathological predilection patterns in Alzheimer disease. Terry R.D., Katzman R., Bick K.L. Alzheimer Disease. 1994;263-291 Raven Press, New York.
7. Gordon M.N., Finch C.E. Topochemical localization of choline acetyltransferase and acetylcholinesterase in mouse brain. Brain Res. 308:1984;364-368.
8. 18F]GBR-13119 . J. Labelled Compd. Radiopharm. 27:1989;823-833.
9. 18F production. Int. J. Appl. Radiat. Isot. 35:1984;599-602.
10. 18F]Fluorodonepezil . J. Labelled Compd. Radiopharm. 42S:1999;617-619.
11. Mulholland G.K., Sugimoto H., Jewett D.M., Kilbourn M.R. Simple preparation of a novel C-11 acetylcholinesterase inhibitor. J. Nucl. Med. 30S:1989;822P.
12. Musachio J.L., Flesher J.E., Scheffel U., Stathis M., Dannals R.F., Ravert H.T., Mathews W.B., Pomper M.G., Frost J.J. Carbon-11 labeling of CP-126,998 A radiotracer for in vivo studies of acetylcholinesterase . J. Nucl. Med. 37S:1996;41P.
13. Oh S.J., Choe Y.S., Shim I., Kim S.E., Chi D.Y., Naruto S., Choi Y., Ha H.J., Kim B.-T. Radiochemical syntheses and biological evaluation of acetylcholinesterase inhibitors, F-18 labeled indole derivatives. J. Nucl. Med. 39S:1998;229P.
14. Pappata S., Tavitian B., Traykov L., Jobert A., Dalger A., Mangin J.F., Crouzel C., Di Giamberardino L. In vivo imaging of human cerebral acetylcholinesterase. J. Neurochem. 67:1996;876-879.
15. 11C]-sarin. J. Labelled Compd. Radiopharm. 28:1990;645-651.
16. Sugimoto H., Iimura Y., Yamanishi Y., Yamatsu K. Synthesis and structure-activity relationship of acetylcholinesterase inhibitors 1-Benzyl-4-[(5,6-dimethoxy-1-oxoindan-2-yl)methyl]piperidine hydrochloride and related compounds . J. Med. Chem. 38:1995;4821-4829.
17. 11C]methyl-tetrahydroaminoacridine (methyl-tacrine) in baboon brain. Eur. J. Pharmacol. 236:1993;229-238.