Fully-automated radiosynthesis of the amyloid tracer [11C] PiB via direct [11C]CO2 fixation-reduction

Pablo Buccino1, Eduardo Savio1, Williams Porcal1,2
1Centro Uruguayo de Imagenología Molecular (CUDIM), Montevideo, Uruguay
2Departamento de Química Orgánica, Facultad de Química, Universidad de la República, Montevideo, Uruguay

Tóm tắt

Từ khóa


Tài liệu tham khảo

Boudjemeline M, Hopewell R, Rochon PL, Jolly D, Hammami I, Villeneuve S, Kostikov A. Highly efficient solid phase supported radiosynthesis of [11C] PiB using tC18 cartridge as a “3-in-1” production entity. J Label Compd Radiopharm. 2017;60(14):632–8.

Coenen HH, Gee AD, Adam M, Antoni G, Cutler CS, Fujibayashi Y, et al. Consensus nomenclature rules for radiopharmaceutical chemistry—Setting the record straight. Nucl Med Biol. 2017;55:v–xi.

Coliva A, Monterisi C, Apollaro A, Gatti D, Penso M, Gianolli L, et al. Synthesis optimization of 2-(4-N-[11C] methylaminophenyl)-6-hydroxybenzothiazole ([11C] PIB), β-amyloid PET imaging tracer for Alzheimer's disease diagnosis. Appl Radiat Isot. 2015;105:66–71.

Das S, Bobbink FD, Laurenczy G, Dyson PJ. Metal-free catalyst for the Chemoselective methylation of amines using carbon dioxide as a carbon source. Angew Chem Int Ed. 2014;53(47):12876–9.

Engler H, Santillo AF, Wang SX, Lindau M, Savitcheva I, Nordberg A, Lannfelt L, Långström B, Kilander L. In vivo amyloid imaging with PET in frontotemporal dementia. Eur J Nucl Med Mol Imaging. 2008;35(1):100–6.

Herholz K, Carter SF, Jones M. Positron emission tomography imaging in dementia. Br J Radiol. 2007;80(special_issue_2):S160–7.

Holschbach M, Schüller M. An on-line method for the preparation of nca [11CH3] trifluoromethanesulfonic acid methyl ester. Appl Radiat Isot. 1993;44(5):897–8.

Jacquet O, Das Neves Gomes C, Ephritikhine M, Cantat T. Recycling of carbon and silicon wastes: room temperature formylation of N–H bonds using carbon dioxide and polymethylhydrosiloxane. J Am Chem Soc. 2012;134(6):2934–7.

Jacquet O, Frogneux X, Gomes CDN, Cantat T. CO 2 as a C 1-building block for the catalytic methylation of amines. Chem Sci. 2013;4(5):2127–31.

Jewett DM. A simple synthesis of [11C] methyl triflate. Int J Rad Appl Instrum A Appl Radiat Isot. 1992;43(11):1383–5.

Jiang X, Wang C, Wei Y, Xue D, Liu Z, Xiao J. A general method for N-methylation of amines and nitro compounds with Dimethylsulfoxide. Chem Eur J. 2014;20(1):58–63.

Klunk WE, Engler H, Nordberg A, Wang Y, Blomqvist G, Holt DP, et al. Imaging brain amyloid in Alzheimer’s disease with Pittsburgh Compound-B. Ann Neurol. 2004;55(3):306–19.

Långström B, Kihlberg T, Bergström M, Antoni G, Björkman M, Forngren BH, et al. Compounds labelled with short-lived beta (+)-emitting radionuclides and some applications in life sciences. The importance of time as a parameter. Acta Chem Scand (Copenhagen, Denmark: 1989). 1999;53(9):651–69.

Li Y, Fang X, Junge K, Beller M. A general catalytic methylation of amines using carbon dioxide. Angew Chem. 2013;125(36):9747–50.

Liger F, Eijsbouts T, Cadarossanesaib F, Tourvieille C, Le Bars D, Billard T. Direct [11C] methylation of amines from [11C] CO2 for the synthesis of PET radiotracers. Eur J Org Chem. 2015;2015(29):6434–8.

Liu XF, Ma R, Qiao C, Cao H, He LN. Fluoride-catalyzed methylation of amines by reductive functionalization of CO2 with Hydrosilanes. Chem Eur J. 2016;22(46):16489–93.

Lv H, Xing Q, Yue C, Lei Z, Li F. Solvent-promoted catalyst-free N-formylation of amines using carbon dioxide under ambient conditions. Chem Commun. 2016;52(39):6545–8.

Mathis CA, Wang Y, Holt DP, Huang GF, Debnath ML, Klunk WE. Synthesis and evaluation of 11C-labeled 6-substituted 2-arylbenzothiazoles as amyloid imaging agents. J Med Chem. 2003;46(13):2740–54.

Nordberg A. PET imaging of amyloid in Alzheimer's disease. Lancet Neurol. 2004;3(9):519–27.

Nordberg A. Amyloid plaque imaging in vivo: current achievement and future prospects. Eur J Nucl Med Mol Imaging. 2008;35(1):46–50.

Philippe C, Haeusler D, Mitterhauser M, Ungersboeck J, Viernstein H, Dudczak R, Wadsak W. Optimization of the radiosynthesis of the Alzheimer tracer 2-(4-N-[11C] methylaminophenyl)-6-hydroxybenzothiazole ([11C] PIB). Appl Radiat Isot. 2011;69(9):1212–7.

Rabinovici GD, Jagust WJ. Amyloid imaging in aging and dementia: testing the amyloid hypothesis in vivo. Behav Neurol. 2009;21(1, 2):117–28.

Rotstein BH, Liang SH, Holland JP, Collier TL, Hooker JM, Wilson AA, Vasdev N. 11 CO 2 fixation: a renaissance in PET radiochemistry. Chem Commun. 2013;49(50):5621–9.

Savio E, García O, Trindade V, Buccino P, Giglio J, Balter H, Engler H. Improving production of 11C to achieve high specific labelled radiopharmaceuticals. AIP Conf Proc. 2012;1509:185–189.

Shekhar AC, Kumar AR, Sathaiah G, Paul VL, Sridhar M, Rao PS. Facile N-formylation of amines using Lewis acids as novel catalysts. Tetrahedron Lett. 2009;50(50):7099–101.

Solbach C, Uebele M, Reischl G, Machulla HJ. Efficient radiosynthesis of carbon-11 labelled uncharged Thioflavin T derivatives using [11C] methyl triflate for β-amyloid imaging in Alzheimer's disease with PET. Appl Radiat Isot. 2005;62(4):591–5.

Furniss BS, Hannaford AJ, Rogers V, Smith PWG, Tatchell AR. Vogel’s Textbook of Practical Organic Chemistry, Including Qualitative Organic Analysis. ELBS; 1978.

Wilson AA, Garcia A, Chestakova A, Kung H, Houle S. A rapid one-step radiosynthesis of the β-amyloid imaging radiotracer N-methyl-[11C] 2-(4′-methylaminophenyl)-6-hydroxybenzothiazole ([11C]-6-OH-BTA-1). J Label Compd Radiopharm. 2004;47(10):679–82.