Synthesis of an I-123 analog of A-85380 and preliminary SPECT imaging of nicotinic receptors in baboon

Musachio, John L.; Villemagne, Victor L.; Scheffel, Ursula A.; Dannals, Robert F.; Dogan, A.Semih; Yokoi, Fuji; Wong, Dean F.

doi:10.1016/s0969-8051(98)00101-2

Cited by 67Radiopharmaceutical Chemistry and ApplicationsNicotinic Acetylcholine Receptors StudyChemical Reactions and Isotopes

Synthesis of an I-123 analog of A-85380 and preliminary SPECT imaging of nicotinic receptors in baboon

Open access

Musachio, John L., Villemagne, Victor L., Scheffel, Ursula A., Dannals, Robert F., Dogan, A.Semih, Yokoi, Fuji, Wong, Dean F.·1999·Nuclear Medicine and Biology

DOI 10.1016/s0969-8051(98)00101-2

Open this paper in CoChat — free account Open PDF

Abstract

A radiosynthetic method to prepare the nicotinic acetylcholine receptor radioligand (S)-5-[123I]iodo-3-(2-azetidinylmethoxy)pyridine, 5-IA, has been developed. The two-step sequence produced [123I]-5-IA in high radiochemical yield (52%), high radiochemical purity (98%), and high specific radioactivities (> 8,500 mCi/mumol). Preliminary single photon emission computed tomography studies with [123I]-5-IA in baboon demonstrated the appropriate regional localization for a high-affinity nicotinic radioprobe (thalamus > frontal cortex > cerebellum). Pretreatment with cytisine blocked [123I]-5-IA uptake in all brain regions (78-59% reduction), demonstrating the specificity of the radiotracer.

The claims and statistics of this paper haven’t been checked yet.

Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.

Integrity signals

Registry

Crossref · 10.1016/s0969-8051(98)00101-2

Cites

29 of 29 references verified0 citation errors · 0 not checkable

Statistics

Claims the paper makes

The claims and statistics of this paper haven’t been checked yet.

Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.

Claims other papers make about this one

Each is checked against this paper’s own text: does it say what the citing paper says it does?

[123I]5-IA is a radioligand that has specificity for the agonist binding site on β2*-nAChRs.
“With the recent development of [ 123 I]5-IA-85380 ([ 123 I]5-IA), a radioligand that has specificity for the agonist binding site on ␤ 2 *- nAChRs (Musachio et al., 1998(Musachio et al., , 1999;;Horti et al., 1999)”
From Human Tobacco Smokers in Early Abstinence Have Higher Levels of β2* Nicotinic Acetylcholine Receptors than Nonsmokers (2006) · cites this paper as Musachio et al., 1999
The Discussion (page not provided) describes [123I]5-IA as a highly specific probe for central nAChRs and reports that the agonist cytisine blocked its uptake in baboon brain. It does not establish specificity for the agonist binding site on β2*-nAChRs; it says only that radioiodinated 5-IA might be more selective for the α4β2 subtype. (LLM, conf=0.86)
Experimental — accuracy not yet measured
The recent development and use of [123I]5-I-A as a SPECT radioligand allows unparalleled access to β2*-nAChRs in vivo in the human brain.
“The recent development and use of [123I]5-I-A ([123I]-5-iodo-3-[2(S)-2-azetidinylmethoxy] pyridine) as a SPECT radioligand to quantify β2*-nAChRs in vivo in the human brain now allows unparalleled access to this system in vivo (23–25).”
From Persistent β 2 *-Nicotinic Acetylcholinergic Receptor Dysfunction in Major Depressive Disorder (2012) · cites this paper as [23]

Self-check

Percentages, sums and reported differences re-computed from the paper’s own numbers.

The self-check needs the paper’s full text.

The mesolimbic dopaminergic system is implicated in the reinforcing effects of nicotine
Corrigall, W. A., Franklin, K. B. J., Coen, K. M., & Clarke, P. B. S. (1992) · Psychopharmacology · doi:10.1007/bf02245149 · Cited by 829 · see citing works
Nicotinic acetylcholine binding sites in Alzheimer's disease
Whitehouse, P. J., Martino, A. M., Antuono, P., Lowenstein, P. R., Coyle, J. T., Price, D. L., & Kellar, K. J. (1986) · Brain Research · doi:10.1016/0006-8993(86)90819-x · Cited by 485 · see citing works
Broad-Spectrum, Non-Opioid Analgesic Activity by Selective Modulation of Neuronal Nicotinic Acetylcholine Receptors
Bannon, A. W., Decker, M. W., Holladay, M. W., Curzon, P., Donnelly‐Roberts, D. L., Puttfarcken, P. S., Bitner, R. S., Díaz, Á., Dickenson, A. H., Porsolt, R. D., et al. (1998) · Science · doi:10.1126/science.279.5347.77 · Cited by 368 · see citing works
Characterization of l ‐[3H]Nicotine Binding in Human Cerebral Cortex: Comparison Between Alzheimer's Disease and the Normal
Flynn, D. D., & Mash, D. C. (1986) · Journal of Neurochemistry · doi:10.1111/j.1471-4159.1986.tb13113.x · Cited by 284 · see citing works
Nicotinic and muscarinic subtypes in the human brain: Changes with aging and dementia
Nordberg, A. K., Alafuzoff, I. I., & Winblad, B. G. (1992) · Journal of Neuroscience Research · doi:10.1002/jnr.490310115 · Cited by 270 · see citing works
Novel 3-Pyridyl Ethers with Subnanomolar Affinity for Central Neuronal Nicotinic Acetylcholine Receptors
Abreo, M. A., Lin, N., Garvey, D. S., Gunn, D., Hettinger, A.-M., Wasicak, J. T., Pavlik, P. A., Martin, Y. C., Donnelly‐Roberts, D. L., Anderson, D. J., et al. (1996) · Journal of Medicinal Chemistry · doi:10.1021/jm9506884 · Cited by 232 · see citing works
Kinetic Analysis of Regional (S)(-)11C-Nicotine Binding in Normal and Alzheimer Brains In Vivo Assessment Using Positron Emission Tomography
Nordberg, A. K., Lundqvist, H., Hartvig, P., Lilja, A., & Långström, B. (1995) · Alzheimer Disease & Associated Disorders · doi:10.1097/00002093-199505000-00006 · Cited by 212 · see citing works
Epibatidine and ABT 418 reveal selective losses of α4β2 nicotinic receptors in Alzheimer brains
Berglund, U. W., & Nordberg, A. K. (1995) · Neuroreport · doi:10.1097/00001756-199511270-00033 · Cited by 148 · see citing works
A-85380 [3-(2(S)-azetidinylmethoxy) pyridine]: In Vitro pharmacological properties of a novel, high affinity α4β2 nicotinic acetylcholine receptor ligand
Sullivan, J. P., Donnelly‐Roberts, D. L., Briggs, C. A., Anderson, D. J., Gopalakrishnan, M., Piattoni-Kaplan, M., Campbell, J. E., McKenna, D. G., Molinari, E., Hettinger, A.-M., et al. (1996) · Neuropharmacology · doi:10.1016/0028-3908(96)84644-2 · Cited by 137 · see citing works
Identification and Initial Structure−Activity Relationships of (R)-5-(2-Azetidinylmethoxy)-2-chloropyridine (ABT-594), a Potent, Orally Active, Non-Opiate Analgesic Agent Acting via Neuronal Nicotinic Acetylcholine Receptors
Holladay, M. W., Wasicak, J. T., Lin, N., et al. (1998) · Journal of Medicinal Chemistry · doi:10.1021/jm9706224 · Cited by 131 · see citing works
PET studies of the uptake of (S)- and (R)-[11C]nicotine in the human brain: difficulties in visualizing specific receptor binding in vivo
Nybäck, H., Halldin, C., Åhlin, A., Curvall, M., & Eriksson, L. I. (1994) · Psychopharmacology · doi:10.1007/bf02244748 · Cited by 108 · see citing works
Nicotinic binding sites in cerebral cortex and hippocampus in alzheimer's dementia
London, E. D., Ball, M. J., & Waller, S. B. (1989) · Neurochemical Research · doi:10.1007/bf00964952 · Cited by 93 · see citing works
[125I]IPH, an Epibatidine Analog, Binds with High Affinity to Neuronal Nicotinic Cholinergic Receptors
Dávila‐García, M. I., Musachio, J. L., Perry, D. C., Xiao, Y., Horti, A. G., London, E. D., Dannals, R. F., & Kellar, K. J. (1997) · Journal of Pharmacology and Experimental Therapeutics · doi:10.1016/s0022-3565(24)36785-0 · Cited by 90 · see citing works
Self-citation
Chapter 30 Attempts to visualize nicotinic receptors in the brain of monkey and man by positron emission tomography
Nybäck, H., Nordberg, A. K., Långström, B., Halldin, C., Hartvig, P., Åhlin, A., Cg, S., & Sedvall, G. (1989) · Progress in brain research · doi:10.1016/s0079-6123(08)62490-5 · Cited by 88 · see citing works
Anatomical atlas of the baboon's brain in the orbito-meatal plane used in experimental positron emission tomography
RICHE, D., Hantraye, P., Guibert, B., Naquet, R., Loc’h, C., Maziere, B., & Mazière, M. (1988) · Brain Research Bulletin · doi:10.1016/0361-9230(88)90058-5 · Cited by 74 · see citing works
Fluoro-norchloroepibatidine: Preclinical assessment of acute toxicity
Molina, P. E., Ding, Y., Carroll, F. I., Liang, F., Volkow, N. D., Pappas, N. R., Kuhar, M. J., Abumrad, N. N., Gatley, S. J., & Fowler, J. S. (1997) · Nuclear Medicine and Biology · doi:10.1016/s0969-8051(97)00120-0 · Cited by 63 · see citing works
Synthesis of a radiotracer for studying nicotinic acetylcholine receptors: 2-[18F]fluoro-3-(2(S)-azetidinylmethoxy)pyridine (2-[18F]A-85380)
Horti, A. G., Koren, A. O., Ravert, H. T., Musachio, J. L., Mathews, W. B., London, E. D., & Dannals, R. F. (1998) · Journal of Labelled Compounds and Radiopharmaceuticals · doi:10.1002/(sici)1099-1344(199804)41:4 · Cited by 59 · see citing works
Self-citation
Imaging nicotinic acetylcholine receptors with fluorine-18-FPH, an epibatidine analog.
Villemagne, V. L., Horti, A. G., Scheffel, U., Ravert, H. T., Finley, P. A., Clough, D. J., London, E. D., Wagner, H. N., & Dannals, R. F. (1997) · PubMed · Cited by 58 · see citing works
Self-citation
5-[I- ]Iodo-3(2(S)-azetidinylmethoxy)pyridine, a radioiodinated analog of A-85380 for in vivo studies of central nicotinic acetylcholine receptors
Musachio, J. L., Scheffel, U., Finley, P. A., Zhan, Y., Mochizuki, T., Wagner, H. N., & Dannals, R. F. (1998) · Life Sciences · doi:10.1016/s0024-3205(98)00180-5 · Cited by 57 · see citing works
Self-citation
Synthesis and structure-activity relationships of pyridine-modified analogs of 3-[2-((S)-pyrrolidinyl)methoxy]pyridine, A-84543, a potent nicotinic acetylcholine receptor agonist
Lin, N., Gunn, D., Li, Y., et al. (1998) · Bioorganic & Medicinal Chemistry Letters · doi:10.1016/s0960-894x(98)00019-5 · Cited by 40 · see citing works
Comparison of two fluorine-18 labeled benzamide derivatives that bind reversibly to dopamine D2 receptors: In vitro binding studies and positron emission tomography
Mach, R. H., Nader, M. A., Ehrenkaufer, R. L., Line, S. W., Smith, C. R., Luedtke, R. R., Kung, M., Kung, H. F., Huston-Lyons, D., & Morton, T. E. (1996) · Synapse · doi:10.1002/(sici)1098-2396(199612)24:4 · Cited by 30 · see citing works
Pharmacological evaluation of [11C]A-84543: An enantioselective ligand for in vivo studies of neuronal nicotinic acetylcholine receptors
Kassiou, M., Scheffel, U., Ravert, H. T., et al. (1998) · Life Sciences · doi:10.1016/s0024-3205(98)00240-9 · Cited by 29 · see citing works
Self-citation
Synthesis of a radioiodinated analog of epibatidine: (±)-exo-2-(2-iodo-5-pyridyl)-7-azabicyclo[2.2.1]heptane for in vitro and in vivo studies of nicotinic acetylcholine receptors
Musachio, J. L., Horti, A. G., London, E. D., & Dannals, R. F. (1997) · Journal of Labelled Compounds and Radiopharmaceuticals · doi:10.1002/(sici)1099-1344(199701)39:1 · Cited by 26 · see citing works
Self-citation
Synthesis and Characterization of Radioiodinated (S)-5-Iodonicotine: A New Ligand for Potential Imaging of Brain Nicotinic Cholinergic Receptors by Single Photon Emission Computed Tomography.
Saji, H., Watanabe, A., Magata, Y., Ohmomo, Y., Kiyono, Y., Yamada, Y., Iida, Y., Yonekura, Y., Konishi, J., & Yokoyama, A. (1997) · Chemical and Pharmaceutical Bulletin · doi:10.1248/cpb.45.284 · Cited by 20 · see citing works
Nicotine receptor mapping
Gr�nwald, F., Biersack, H.-J., & Kuschinsky, W. (1996) · European Journal of Nuclear Medicine and Molecular Imaging · doi:10.1007/bf01084381 · Cited by 18 · see citing works
Oxidative stress induces age-dependent changes in lymphocyte protein synthesis and second messenger levels
López-Hellín, J., García‐Arumí, E., & Schwartz, S. (1998) · Life Sciences · doi:10.1016/s0024-3205(98)00231-8 · Cited by 16 · see citing works
Synthesis of [3H2]-(R,R)-1,2-diaminocyclohexaneoxalatoplatinum(II), [3H2]-Oxaliplatin
Burgos, A., & Ellames, G. J. (1998) · Journal of Labelled Compounds and Radiopharmaceuticals · doi:10.1002/(sici)1099-1344(199805)41:5 · Cited by 8 · see citing works
Synthesis and biodistribution of radioiodinated‐5‐iodonicotine
Chan, S.-H., Basmadjian, G. P., Marten, D. F., et al. (1983) · Journal of Labelled Compounds and Radiopharmaceuticals · doi:10.1002/jlcr.2580200813 · Cited by 8 · see citing works
Comparing long-term depression with pharmacologically induced synaptic attenuations in young rat hippocampi
Xiao, M., Niu, Y., & Wigstr�m, H. (1997) · Synapse · doi:10.1002/(sici)1098-2396(199708)26:4 · Cited by 8 · see citing works

Flagged first, then by citations

Sorted by citations

Human Tobacco Smokers in Early Abstinence Have Higher Levels of β2* Nicotinic Acetylcholine Receptors than Nonsmokers
Staley, J. K., Krishnan-Sarin, S., Cosgrove, K. P., Krantzler, E., Frohlich, E., Perry, E., Dubin, J. A., Estok, K., Brenner, E., Baldwin, R. M., et al. (2006) · The Journal of Neuroscience · doi:10.1523/jneurosci.0546-06.2006 · Cited by 223 · see citing works
“With the recent development of [ 123I]5-IA-85380 ([ 123I]5-IA), a radioligand that has specificity for the agonist binding site on 2*- nAChRs (Musachio et al., 1998, 1999; Horti et al., 1999), it is now possible to measure this site in living smokers during acute abstinence from smoking and to…”
5-Iodo-A-85380, an α4β2 Subtype-Selective Ligand for Nicotinic Acetylcholine Receptors
Mukhin, A. G., Gündisch, D., Horti, A. G., Koren, A. O., Tamagnan, G., Kimes, A. S., Chambers, J., Vaupel, D. B., King, S. L., Picciotto, M. R., et al. (2000) · Molecular Pharmacology · doi:10.1124/mol.57.3.642 · Cited by 173 · see citing works
Sazetidine-A, A Novel Ligand That Desensitizes α4β2 Nicotinic Acetylcholine Receptors without Activating Them
Xiao, Y., Fan, H., Musachio, J. L., Wei, Z.-L., Chellappan, S. K., Kozikowski, A. P., & Kellar, K. J. (2006) · Molecular Pharmacology · doi:10.1124/mol.106.027318 · Cited by 141 · see citing works
Self-citation
Persistent β 2 *-Nicotinic Acetylcholinergic Receptor Dysfunction in Major Depressive Disorder
Saricicek, A., Esterlis, I., Maloney, K. H., Mineur, Y. S., Ruf, B. M., Muralidharan, A., Chen, J. I., Cosgrove, K. P., Kerestes, R., Ghose, S., et al. (2012) · American Journal of Psychiatry · doi:10.1176/appi.ajp.2012.11101546 · Cited by 118 · see citing works
In vivo imaging of nicotinic receptor upregulation following chronic (−)-nicotine treatment in baboon using SPECT
Kassiou, M., Eberl, S., Meikle, S. R., Birrell, A., Constable, C., Fulham, M. J., Wong, D. F., & Musachio, J. L. (2001) · Nuclear Medicine and Biology · doi:10.1016/s0969-8051(00)00206-7 · Cited by 58 · see citing works
Self-citation
Influence of acetylcholine levels on the binding of a SPECT nicotinic acetylcholine receptor ligand [123I]5‐I‐A‐85380
Fujita, M., Al‐Tikriti, M. S., Tamagnan, G., Zoghbi, S. S., Bozkurt, A., Baldwin, R. M., & Innis, R. B. (2003) · Synapse · doi:10.1002/syn.10194 · Cited by 24 · see citing works

Authors: Musachio, J. L., Villemagne, V. L., Scheffel, U. A., Dannals, R. F., Dogan, A. S., Yokoi, F., & Wong, D. F.
Affiliations: Johns Hopkins University (US)
Corresponding author: Musachio, John L.
ORCID: Villemagne, Victor L.
Wong, Dean F.
Venue: Nuclear Medicine and Biology
Publisher: Elsevier BV
Published: 1999-02
Volume: 26
Issue: 2
Pages: 201-207
ISSN: 0969-8051 (ISSN-L)
DOI: 10.1016/s0969-8051(98)00101-2
OpenAlex: W2072961809
Cited by: 67
References: 29
Citations by year: 2019: 1 · 2018: 2 · 2015: 1 · 2014: 1 · 2013: 2 · 2012: 4
FWCI: 5.76
Type: journal article
Language: en
Open access: hybrid
doi.org
Licence: cc-by-nc-nd
www.elsevier.com/tdm/userlicense/1.0/ (tdm)
www.elsevier.com/legal/tdmrep-license (tdm)
creativecommons.org/licenses/by-nc-nd/4.0/ (vor, 373 d)
Locations: Nuclear Medicine and Biology (publishedVersion, cc-by-nc-nd)
PubMed (publishedVersion)
Funders: National Cancer Institute (CA 77349, HD 24448)
U.S. Public Health Service
Topics: Health Sciences › Medicine › Radiology, Nuclear Medicine and Imaging › Radiopharmaceutical Chemistry and Applications
Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Nicotinic Acetylcholine Receptors Study
Life Sciences › Pharmacology, Toxicology and Pharmaceutics › Pharmaceutical Science › Chemical Reactions and Isotopes
Keywords: nicotinic acetylcholine receptors, radioligand synthesis, iodine-123, SPECT imaging, baboons, cytisine, thalamus, frontal cortex, cerebellum
MeSH terms: Animals, Azetidines, Brain, Iodine Radioisotopes, Male, Papio, Radiochemistry, Radioligand Assay, Receptors, Nicotinic, Molecular Structure, Tomography, Emission-Computed, Single-Photon, Rats, Sprague-Dawley, Rats

About these checks

Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.

Statistics and arithmetic are recomputed, not judged.

Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.

What counts as a claim ›How we measure confidence ›How we check this ›

Are you an author, or do you see a problem with this page? Request a review

Synthesis of an I-123 analog of A-85380 and preliminary SPECT imaging of nicotinic receptors in baboon

Abstract

Integrity signals

Claims the paper makes

Claims other papers make about this one

Self-check

Cites

Cited by

Related

Record

About these checks