Initial Evaluation of AF78: a Rationally Designed Fluorine-18-Labelled PET Radiotracer Targeting Norepinephrine Transporter.
Animals
Autoradiography
/ methods
Cell Line, Tumor
Fluorine Radioisotopes
/ chemistry
Male
Neuroblastoma
/ diagnostic imaging
Norepinephrine Plasma Membrane Transport Proteins
/ metabolism
Phenformin
/ analogs & derivatives
Positron-Emission Tomography
/ methods
Radiochemistry
/ methods
Radiopharmaceuticals
/ chemical synthesis
Rats
Rats, Wistar
Tissue Distribution
Norepinephrine transporter
Phenethylguanidine
Positron emission tomography
[18F]AF78
Journal
Molecular imaging and biology
ISSN: 1860-2002
Titre abrégé: Mol Imaging Biol
Pays: United States
ID NLM: 101125610
Informations de publication
Date de publication:
06 2020
06 2020
Historique:
pubmed:
25
7
2019
medline:
3
6
2021
entrez:
24
7
2019
Statut:
ppublish
Résumé
Taking full advantage of positron emission tomography (PET) technology, fluorine-18-labelled radiotracers targeting norepinephrine transporter (NET) have potential applications in the diagnosis and assessment of cardiac sympathetic nerve conditions as well as the delineation of neuroendocrine tumours. However, to date, none have been used clinically. Drawbacks of currently reported radiotracers include suboptimal kinetics and challenging radiolabelling procedures. We developed a novel fluorine-18-labelled radiotracer targeting NET, AF78, with efficient one-step radiolabelling based on the phenethylguanidine structure. Radiosynthesis of AF78 was undertaken, followed by validation in cell uptake studies, autoradiography, and in vivo imaging in rats. [ The new PET radiotracer [
Identifiants
pubmed: 31332629
doi: 10.1007/s11307-019-01407-5
pii: 10.1007/s11307-019-01407-5
pmc: PMC7250802
doi:
Substances chimiques
Fluorine Radioisotopes
0
Norepinephrine Plasma Membrane Transport Proteins
0
Radiopharmaceuticals
0
phenethylguanidine
538-69-2
Phenformin
DD5K7529CE
Fluorine-18
GZ5I74KB8G
Types de publication
Evaluation Study
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
602-611Références
Werner RA, Chen X, Hirano M, Rowe SP, Lapa C, Javadi MS, Higuchi T (2018) SEPCT vs. PET in cardiac innervation imaging: clash of the titans. Clin Transl Imaging 6:293–303
doi: 10.1007/s40336-018-0289-4
Chen X, Werner RA, Javadi MS, Maya Y, Decker M, Lapa C, Herrmann K, Higuchi T (2015) Radionuclide imaging of neurohormonal system of the heart. Theranostics 5:545–585
doi: 10.7150/thno.10900
Kobayashi R, Chen X, Werner RA, Lapa C, Javadi MS, Higuchi T (2017) New horizon in cardiac innervation imaging: introduction of novel
doi: 10.1007/s00259-017-3828-8
Parati G, Esler M (2012) The human sympathetic nervous system: its relevance in hypertension and heart failure. Eur Heart J 33:1058–1066
doi: 10.1093/eurheartj/ehs041
Fukuda K, Kanazawa H, Aizawa Y, Ardell JL, Shivkumar K (2015) Cardiac innervation and sudden cardiac death. Circ Res 116:2005–2019
doi: 10.1161/CIRCRESAHA.116.304679
Franciosi S, Perry FKG, Roston TM, Armstrong KR, Claydon VE, Sanatani S (2017) The role of the autonomic nervous system in arrhythmias and sudden cardiac death. Auton Neurosci 205:1–11
doi: 10.1016/j.autneu.2017.03.005
Pandit-Taskar N, Modak S (2017) Norepinephrine transporter as a target for imaging and therapy. J Nucl Med 58(Suppl 2):39S–53S
doi: 10.2967/jnumed.116.186833
Goldstein DS, Eisenhofer G, Dunn BB, Armando I, Lenders J, Grossman E, Holmes C, Kirk KL, Bacharach S, Adams R, Herscovitch P, Kopin IJ (1993) Positron emission tomographic imaging of cardiac sympathetic innervation using 6-[
doi: 10.1016/0735-1097(93)90786-Z
Goldstein DS, Katzper M, Linares O, Kopin IJ (2002) Kinetic model for the fate of 6-[
doi: 10.1007/s002100100426
Zhang H, Huang R, Pillarsetty N, Thorek DLJ, Vaidyanathan G, Serganova I, Blasberg RG, Lewis JS (2014) Synthesis and evaluation of
doi: 10.1007/s00259-013-2558-9
Pandit-Taskar N, Zanzonico P, Staton KD, Carrasquillo JA, Reidy-Lagunes D, Lyashchenko S, Burnazi E, Zhang H, Lewis JS, Blasberg R, Larson SM, Weber WA, Modak S (2018) Biodistribution and dosimetry of
doi: 10.2967/jnumed.117.193169
Higuchi T, Yousefi BH, Kaiser F, Gartner F, Rischpler C, Reder S, Yu M, Robinson S, Schwaiger M, Nekolla SG (2013) Assessment of the
doi: 10.2967/jnumed.112.104232
Werner RA, Rischpler C, Onthank D, Lapa C, Robinson S, Samnick S, Javadi M, Schwaiger M, Nekolla SG, Higuchi T (2015) Retention kinetics of the
doi: 10.2967/jnumed.115.158493
Chen X, Werner RA, Lapa C, Nose N, Hirano M, Javadi MS, Robinson S, Higuchi T (2018) Subcellular storage and release mode of the novel
doi: 10.1186/s13550-018-0365-9
Raffel DM, Jung YW, Gildersleeve DL, Sherman PS, Moskwa JJ, Tluczek LJ, Chen W (2007) Radiolabeled phenethylguanidines: novel imaging agents for cardiac sympathetic neurons and adrenergic tumors. J Med Chem 50:2078–2088
doi: 10.1021/jm061398y
Jang KS, Jung YW, Gu G, Koeppe RA, Sherman PS, Quesada CA, Raffel DM (2013) 4-[
doi: 10.1021/jm400770g
Sinusas AJ, Lazewatsky J, Brunetti J, Heller G, Srivastava A, Liu YH, Sparks R, Puretskiy A, Lin SF, Crane P, Carson RE, Lee LV (2014) Biodistribution and radiation dosimetry of LMI1195: first-in-human study of a novel
doi: 10.2967/jnumed.114.140137
Jung YW, Jang KS, Gu G, Koeppe RA, Sherman PS, Quesada CA, Raffel DM (2017) [
doi: 10.1021/acschemneuro.7b00051
Raffel DM, Jung YW, Koeppe RA et al (2018) First-in-human studies of [
doi: 10.1161/CIRCIMAGING.118.007965
Rischpler C, Fukushima K, Isoda T, Javadi MS, Dannals RF, Abraham R, Wahl R, Bengel FM, Higuchi T (2013) Discrepant uptake of the radiolabeled norepinephrine analogues hydroxyephedrine (HED) and metaiodobenzylguanidine (MIBG) in rat hearts. Eur J Nucl Med Mol Imaging 40:1077–1083
doi: 10.1007/s00259-013-2393-z
Jang KS, Jung YW, Sherman PS, Quesada CA, Gu G, Raffel DM (2013) Synthesis and bioevaluation of [
doi: 10.1016/j.bmcl.2013.01.106
Nilsson BL, Overman LE (2006) Concise synthesis of guanidine-containing heterocycles using the Biginelli reaction. J Organomet Chem 71:7706–7714
doi: 10.1021/jo061199m
Hu B, Vavere AL, Neumann KD et al (2015) A practical, automated synthesis of meta-[
doi: 10.1021/acschemneuro.5b00202
Brockway AJ, Grove CI, Mahoney ME, Shaw JT (2015) Synthesis of the diaryl ether cores common to chrysophaentins a, E, and F. Tetrahedron Lett 56:3396–3401
doi: 10.1016/j.tetlet.2015.01.073
Crouch RD, Mitten JV, Span AR, Dai HG (1997) A mild, convenient, non-acidic conversion of enol ethers into alcohols using hg(OAc)
doi: 10.1016/S0040-4039(96)02449-5
Yu M, Bozek J, Lamoy M, Kagan M, Benites P, Onthank D, Robinson SP (2012) LMI1195 PET imaging in evaluation of regional cardiac sympathetic denervation and its potential role in antiarrhythmic drug treatment. Eur J Nucl Med Mol Imaging 39:1910–1919
doi: 10.1007/s00259-012-2204-y
Vaidyanathan G, McDougald D, Koumarianou E, Choi J, Hens M, Zalutsky MR (2015) Synthesis and evaluation of 4-[
doi: 10.1016/j.nucmedbio.2015.04.005
Woo SK, Moon BS, Kim BS, Kim MH, Lee YJ, Jung JH, Lee KC, Seo Y, Kim W, Lim SM, Lee BC, Kim SE (2018) Feasibility of myocardial PET imaging using a benzylguanidine analog: meta-(3-[
doi: 10.1016/j.nucmedbio.2018.04.005
Yu M, Bozek J, Lamoy M, Guaraldi M, Silva P, Kagan M, Yalamanchili P, Onthank D, Mistry M, Lazewatsky J, Broekema M, Radeke H, Purohit A, Cdebaca M, Azure M, Cesati R, Casebier D, Robinson SP (2011) Evaluation of LMI1195, a novel
doi: 10.1161/CIRCIMAGING.110.962126
Yamaguchi A, Hanaoka H, Higuchi T, Tsushima Y (2018) Radiolabeled (4-fluoro-3-iodobenzyl)guanidine improves imaging and targeted radionuclide therapy of norepinephrine transporter-expressing tumors. J Nucl Med 59:815–821
doi: 10.2967/jnumed.117.201525
Iversen LL, Salt PJ, Wilson HA (1972) Inhibition of catecholamine uptake in the isolated rat heart by haloalkylamines related to phenoxybenzamine. Br J Pharmacol 46:647–657
doi: 10.1111/j.1476-5381.1972.tb06890.x
Werner RA, Chen X, Rowe SP et al (2019) Recent paradigm shifts in molecular cardiac imaging-establishing precision cardiology through novel 18F-labeled PET radiotracers. Trends Cardiovasc Med. https://doi.org/10.1016/j.tcm.2019.02.007
doi: 10.1016/j.tcm.2019.02.007
Aikawa T, Naya M, Obara M, Oyama-Manabe N, Manabe O, Magota K, Ito YM, Katoh C, Tamaki N (2017) Regional interaction between myocardial sympathetic denervation, contractile dysfunction, and fibrosis in heart failure with preserved ejection fraction:
doi: 10.1007/s00259-017-3760-y
Hiroshima Y, Manabe O, Naya M, Tomiyama Y, Magota K, Obara M, Aikawa T, Oyama-Manabe N, Yoshinaga K, Hirata K, Kroenke M, Tamaki N, Katoh C (2017) Quantification of myocardial blood flow with
Wong KK, Raffel DM, Bohnen NI, Altinok G, Gilman S, Frey KA (2017) 2-year natural decline of cardiac sympathetic innervation in idiopathic Parkinson disease studies with
doi: 10.2967/jnumed.116.176891
Fallavollita JA, Heavey BM, Luisi AJ Jr, Michalek SM, Baldwa S, Mashtare TL Jr, Hutson AD, deKemp RA, Haka MS, Sajjad M, Cimato TR, Curtis AB, Cain ME, Canty JM Jr (2014) Regional myocardial sympathetic denervation predicts the risk of sudden cardiac arrest in ischemic cardiomyopathy. J Am Coll Cardiol 63:141–149
doi: 10.1016/j.jacc.2013.07.096
Gaertner FC, Wiedemann T, Yousefi BH, Lee M, Repokis I, Higuchi T, Nekolla SG, Yu M, Robinson S, Schwaiger M, Pellegata NS (2013) Preclinical evaluation of
doi: 10.2967/jnumed.113.119966
Zelt J, Renaud J, Mielniczuk L, et al. (2018) Fluorine-18 LMI1195 positron emission tomography provides accurate measure of cardiac sympathetic innervation compared to carbon-11 hydroxyephedrine. 71(Suppl 11), DOI: https://doi.org/10.1016/S0735-1097(18)32023-0
doi: 10.1016/S0735-1097(18)32023-0