Pharmacological and toxicological evaluation of 2-fluoro-3-(2(S)- azetidinylmethoxy)pyridine (2-F-A-85380), a ligand for imaging cerebral nicotinic acetylcholine receptors with positron emission tomography

Journal of Pharmacology and Experimental Therapeutics

Volumn 312, Issue 1, 2005, Pages 355-365

  Vaupel, D Bruce ^a   Tella, Srihari R ^b   Huso, David L ^c   Wagner III, Valentine O ^d   Mukhin, Alexey G ^a   Chefer, Svetlana I ^a   Horti, Andrew G ^a   London, Edythe D ^e   Koren, Andrei O ^e   Kimes, Alane S ^a  

^a NATIONAL INSTITUTE ON DRUG ABUSE   (United States)

^b GEORGETOWN UNIVERSITY MEDICAL CENTER   (United States)

^c JOHNS HOPKINS UNIVERSITY SCHOOL OF MEDICINE   (United States)

^d BioReliance   (United States)

^e UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 FLUORO 3 (2 AZETIDINYLMETHOXY)PYRIDINE F 18; HEXAMETHONIUM; MECAMYLAMINE; NICOTINE; NICOTINIC RECEPTOR; RADIOLIGAND; UNCLASSIFIED DRUG;

AMES TEST; ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BACTERIAL STRAIN; BLADDER WALL; BODY TEMPERATURE; BODY WEIGHT; CONTROLLED STUDY; CONVULSION; DIASTOLIC BLOOD PRESSURE; DOSIMETRY; DRUG MEGADOSE; DRUG SAFETY; ELECTROCARDIOGRAM; FEMALE; HEART MUSCLE CONTRACTILITY; HEART RATE; HISTOPATHOLOGY; LOCOMOTION; MALE; MOUSE; MUTAGENICITY; NONHUMAN; POSITRON EMISSION TOMOGRAPHY; PR INTERVAL; PRIORITY JOURNAL; QRS COMPLEX; QT INTERVAL; RADIATION EXPOSURE; RAT; RHESUS MONKEY; SYSTOLIC BLOOD PRESSURE; TONIC CLONIC SEIZURE;

ANIMALS; BEHAVIOR, ANIMAL; BLOOD PRESSURE; BODY TEMPERATURE; BODY WEIGHT; CARDIOVASCULAR SYSTEM; CEREBRAL CORTEX; CONVULSANTS; DOSE-RESPONSE RELATIONSHIP, DRUG; ELECTROCARDIOGRAPHY; FEMALE; FLUORINE RADIOISOTOPES; HEART RATE; MALE; MICE; MOTOR ACTIVITY; MYOCARDIAL CONTRACTION; POSITRON-EMISSION TOMOGRAPHY; PRIMATES; PYRIDINES; RATS; RATS, SPRAGUE-DAWLEY; RECEPTORS, NICOTINIC;

EID: 19944428892     PISSN: 00223565     EISSN: None     Source Type: Journal    
DOI: 10.1124/jpet.104.073999     Document Type: Article

References (39)

1. Abreo MA, Lin NH, Garvey DS, Gunn DE, Hettinger AM, Wasicak JT, Pavlik PA, Martin YC, Donnelly-Robert DL, Anderson DJ, et al. (1996) Novel 3-pyridyl ethers with subnanomolar affinity for central neuronal nicotinic acetylcholine receptors. J Med Chem 39:817-825.
2. 18F-fluoro-A-85380 in healthy volunteers. J Nucl Med 44:596-601.
3. Buchl SJ and Howard B (1997) Hematologic and serum biochemical and electrolyte values in clinically normal domestically bred rhesus monkeys (Macaca mulatta) according to age, sex and gravidity. Lab Anim Sci 47:528-533.
4. Cambridge D and Whiting WV (1986) Evaluation of the QA interval as an index of cardiac contractility in anaesthetized dogs: responses to changes in cardiac loading and heart rate. Cardiovasc Res 20:444-450.
5. 123I]iodo-A-85380 using single photon emission computed tomography. Life Sci 63:PL355-PL360.
6. 18F]fluoro-A-85380: a PET ligand for quantitative studies of nicotinic acetylcholine receptors. Proceedings of International Conference on Mathematics and Engineering Techniques in Medicine and Biological Sciences (MET-MBS'2000); 2000 Jun 26-29; Las Vegas, NV. Vol 2, pp. 409-415, CSREA Press, Las Vegas, NV.
7. Dhar S, Nagy F, McIntosh JM, and Sapru HN (2000) Receptor subtypes mediating depressor responses to microinjections of nicotine into medial NTS of the rat. Am J Physiol Regul Integr Camp Physiol 278:R132-R140.
8. 18F]fluoro-3-[2(S)-2- azetidinylmethoxy]pyridine, a highly potent radioligand for in vivo imaging central nicotine acetylcholine receptors. J Labelled Compd Radiopharm 41:451-463.
9. Driscoll P (1976) Inhalation of smoke from high- and low-nicotine cigarettes by guinea-pigs: behavioral and ECG effects, in Adverse Effects of Environmental Chemicals and Psychotropic Drugs: Neurophysiological and Behavioral Tests (Horvath M ed) vol 2, pp 241-256, Elsevier Scientific Publishing Co., New York.
10. 123I]5-I-A- 85380 in healthy human subjects. Eur J Nucl Med Mol Imaging 28:183-190.
11. Fuller GB, Hobson WC, Renquist DM, Port CD, and Chengelis CP (1992) Nonhuman primates, in Animal Models in Toxicology (Gad SC and Chengelis CP eds) pp 675-735, Marcel Dekker, Inc, New York.
12. Gelzer ARM and Ball HA (1997) Validation of a telemetry system for measurement of blood pressure, electrocardiogram and locomotor activity in beagle dogs. Clin Exp Hypertens 19:1135-1160.
13. Henningfield JE, Miyasato K, and Jasinski DR (1985) Abuse liability and pharmacodynamic characteristics of intravenous and inhaled nicotine. J Pharmacol Exp Ther 234:1-12.
14. Holladay MW, Bai H, Li Y, Lin NH, Daanen JF, Ryther KB, Wasicak JT, Kincaid JF, He Y, Hettinger AM, et al. (1998) Structure-activity studies related to ABT-594, a potent nonopioid analgesic agent: effect of pyridine and azetidine ring substitutions on nicotinic acetylcholine receptor binding affinity and analgesic activity in mice. Bioorg Med Chem Lett 9:2797-2802.
15. Hom GJ, Bach TJ, Carroll D, Forrest MJ, Mariano MA, Trainor CE, Wang PR, and Macintyre DE (1999) Comparison of cardiovascular parameters and/or serum chemistry and hematology profiles in conscious and anesthetized rhesus monkeys (Macaca mulatta). Contemp Top Lab Anim Sci 38:60-64.
16. 123/125I]iodo3-(2(S)-azetidinyknethoxy)pyridine: a radioligand for nicotinic acetylcholine receptors. Nucl Med Biol 26:175-182.
17. 18F]-A-85380). J Labelled Compd Radiopharm 41:309-318.
18. Khan IM, Taylor P, and Yaksh TL (1994a) Cardiovascular and behavioral responses to nicotinic agents administered intrathecally. J Pharmacol Exp Ther 270:150-158.
19. Khan IM, Taylor P, and Yaksh TL (1994b) Stimulatory pathways and sites of action of intrathecally administered nieotinie agents. J Pharmacol Exp Ther 271:1550-1557.
20. 18F]F-A-85380: PET imaging of brain nicotinic acetylcholine receptors and whole body distribution in humans. FASEB J 17:331-333.
21. Koren AO, Horti AG, Mukhin AG, Gundisch D, Kimes AS, Dannals RF, and London ED (1998) 2-, 5- and 6- Halo-3-(2(S)-azetidinylmethoxy)pyridines: synthesis, affinity for nicotinic acetylcholine receptors and molecular modeling. J Med Chem 41:3690-3698.
22. Kubo T and Misu Y (1981) Changes in arterial blood pressure after microinjections of nicotine into the dorsal area of the medulla oblongata of the rat. Neuropharmacology 20:521-524.
23. Litchfield JT and Wilcoxin F (1949) A simplified method of evaluating dose-effect experiments. J Pharmacol Exp Ther 96:99-113.
24. Maron DM and Ames BN (1983) Revised methods for the Salmonella mutagenicity test. Mutat Res 113:173-215.
25. Molina P, Ding YS, Carrol FI, Liant F, Volkow N, Kuhar M, Pappas N, King P, Abumrad N, and Fowler JS (1997) Fluoro-norchloroepibatidine: preclinical assessment of acute toxicity. Nucl Med Biol 24:743-747.
26. Mukhin AG, Gündisch D, Horti AG, Koren AO, Tamagnan G, Kimes AS, Chambers J, Vaupel DB, King SL, Picciottto MR, et al. (2000) 5-Iodo-A-85380, an α4β2 subtype-selective ligand for nicotinic acetylcholine receptors. Mol Pharmacol 57:643-649.
27. Musachio JL, Scheffel U, Finley PA, Zhan Y, Mochizuki T, Wagner HN Jr, and Dannals RF (1998) 5-[I-125/123]iodo-3(2(S)-azetidinlymethoxy)pyridine, a radioiodinated analogue of A-85380 for in vivo studies of central nicotinic acetylcholine receptors. Life Sci 22:PL351-PL357.
28. 18F]F-A-85380, a novel PET ligand for α4β2 nicotinic receptors. Soc Neurosci Abstr 26:627, 235.16.
29. Pourrias B, Porsolt RD, and Lacroix P (1999) QT interval prolongation by noncardiovascular drugs: a proposed assessment strategy. Drug Dev Res 47:55-62.
30. Rose JE, Behm FM, and Westman EC (2001) Acute effects of nicotine and mecamylamine on tobacco withdrawal symptoms, cigarette reward and ad lib smoking. Pharmacol Biochem Behav 68:187-197.
31. 2+ channel blocker AH-1058 in conscious dogs assessed by telemetry. Eur J Pharmacol 413:101-108.
32. Taylor P (2001) Agents acting at the neuromuscular junction and autonomic ganglia, in Goodman and Gilman's The Pharmacological Basis of Therapeutics (Hardman JG, Limbird LE, and Gilman AG eds), 10th ed, pp 193-213, McGraw-Hill, New York.
33. Tella SR (1996) Possible novel pharmacodynamic action of cocaine: cardiovascular and behavioral effects. Pharmacol Biochem Behav 54:343-354.
34. Tseng CJ, Appalsamy M, Robertson D, and Mosqueda-Garcia R (1993) Effects of nicotine on brain stem mechanisms of cardiovascular control. J Pharmacol Exp Ther 265:1511-1518.
35. Valette H, Dollé F, Bottlaender M, and Marzin D (2002) Fluoro-A-85380 demonstrated no mutagenic properties in in vivo rat micronucleus and Ames tests. Nucl Med Biol 29:849-853.
36. Vaupel DB, London ED, Horti AG, Koren AO, Mukhin AG, Chefer SI, Pavlova OA, Stratton M, Huso DL, Tella SR, et al. (2002) 2-[F-18]F-A-85380 acquires phase 1 approval as a radiotracer for imaging α4β2 nicotinic receptors in human PET studies (Abstract). Drug Alcohol Depend 66 (Suppl 1):S187.
37. 125I]5-I-A-85380, a nicotinic acetylcholine receptor radioligand. Neuroreport 9:2311-2317.
38. 123I]5-I-A-85380, a radioligand for in vivo imaging of cerebral neuronal nicotinic acetylcholine receptors in humans. Drug Dev Res 58:149-168.
39. Volle RL and Koelle GB (1965) Ganglionic stimulating and blocking drugs, in Goodman and Gilman's The Pharmacological Basis of Therapeutics (Goodman LS and Gilman A eds), 3rd ed, pp 578-595, Macmillan Company, New York.