Synthesis of a PET tau tracer [11C]PBB3 for imaging of Alzheimer’s disease

[Display omitted] The authentic standard PBB3 and its precursor N-desmethyl-PBB3 as well as TBS-protected N-desmethyl-PBB3 precursor for radiolabeling were synthesized from 5-bromo-2-nitropyridine, acrolein diethyl acetal, 6-methoxy-2-methylbenzothiazole, and diethylchlorophosphate with overall chem...

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Published in	Bioorganic & medicinal chemistry letters Vol. 25; no. 20; pp. 4587 - 4592
Main Authors	Wang, Min, Gao, Mingzhang, Xu, Zhidong, Zheng, Qi-Huang
Format	Journal Article
Language	English
Published	OXFORD Elsevier Ltd 15.10.2015 Elsevier
Subjects	[11C]PBB3 Alzheimer Disease - diagnosis Alzheimer Disease - metabolism Alzheimer’s disease (AD) Aminopyridines - chemical synthesis Aminopyridines - chemistry Benzothiazoles - chemical synthesis Benzothiazoles - chemistry Carbon Radioisotopes Chemistry Chemistry, Medicinal Chemistry, Organic Humans Life Sciences & Biomedicine Molecular Imaging Molecular Structure Pharmacology & Pharmacy Physical Sciences Positron emission tomography (PET) Positron-Emission Tomography Radiosynthesis Science & Technology tau Proteins - analysis Tau tracer Positron emission tomography (PET) Alzheimer’s disease (AD) Tau tracer [11C]PBB3 Radiosynthesis ROUTE RADIOLIGAND FULLY AUTOMATED SYNTHESIS ACROLEIN-DIETHYL-ACETAL NEUROFIBRILLARY PATHOLOGY Alzheimer's disease (AD) RADIOTRACERS PROBES [C-11]PBB3 1ST RADIOSYNTHESIS AGENTS CINNAMALDEHYDES [C]PBB3
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Abstract	[Display omitted] The authentic standard PBB3 and its precursor N-desmethyl-PBB3 as well as TBS-protected N-desmethyl-PBB3 precursor for radiolabeling were synthesized from 5-bromo-2-nitropyridine, acrolein diethyl acetal, 6-methoxy-2-methylbenzothiazole, and diethylchlorophosphate with overall chemical yield 1% in six steps, 2% in five steps, and 1% in six steps, respectively. [11C]PBB3 was prepared from either desmethyl-PBB3 or TBS-protected desmethyl-PBB3 with [11C]CH3OTf through N-[11C]methylation and isolated by HPLC combined with SPE in 20–25% and 15–20% radiochemical yield, respectively, based on [11C]CO2 and decay corrected to end of bombardment (EOB). The radiochemical purity was >99%, and the specific activity at EOB was 370–1110GBq/μmol with a total synthesis time of ∼40-min from EOB.
AbstractList	The authentic standard PBB3 and its precursor N-desmethyl-PBB3 as well as TBS-protected N-desmethyl-PBB3 precursor for radiolabeling were synthesized from 5-bromo-2-nitropyridine, acrolein diethyl acetal, 6-methoxy-2-methylbenzothiazole, and diethylchlorophosphate with overall chemical yield 1% in six steps, 2% in five steps, and 1% in six steps, respectively. [(11)C]PBB3 was prepared from either desmethyl-PBB3 or TBS-protected desmethyl-PBB3 with [(11)C]CH3OTf through N-[(11)C]methylation and isolated by HPLC combined with SPE in 20-25% and 15-20% radiochemical yield, respectively, based on [(11)C]CO2 and decay corrected to end of bombardment (EOB). The radiochemical purity was >99%, and the specific activity at EOB was 370-1110 GBq/μmol with a total synthesis time of ~40-min from EOB. [Display omitted] The authentic standard PBB3 and its precursor N-desmethyl-PBB3 as well as TBS-protected N-desmethyl-PBB3 precursor for radiolabeling were synthesized from 5-bromo-2-nitropyridine, acrolein diethyl acetal, 6-methoxy-2-methylbenzothiazole, and diethylchlorophosphate with overall chemical yield 1% in six steps, 2% in five steps, and 1% in six steps, respectively. [11C]PBB3 was prepared from either desmethyl-PBB3 or TBS-protected desmethyl-PBB3 with [11C]CH3OTf through N-[11C]methylation and isolated by HPLC combined with SPE in 20–25% and 15–20% radiochemical yield, respectively, based on [11C]CO2 and decay corrected to end of bombardment (EOB). The radiochemical purity was >99%, and the specific activity at EOB was 370–1110GBq/μmol with a total synthesis time of ∼40-min from EOB. The authentic standard PBB3 and its precursor N-desmethyl-PBB3 as well as TBS-protected N-desmethyl-PBB3 precursor for radiolabeling were synthesized from 5-bromo-2-nitropyridine, acrolein diethyl acetal, 6-methoxy-2-methylbenzothiazole, and diethylchlorophosphate with overall chemical yield 1% in six steps, 2% in five steps, and 1% in six steps, respectively. [C-11]PBB3 was prepared from either desmethyl-PBB3 or TBS-protected desmethyl-PBB3 with [C-11]CH3OTf through N-[C-11] methylation and isolated by HPLC combined with SPE in 20-25% and 15-20% radiochemical yield, respectively, based on [C-11]CO2 and decay corrected to end of bombardment (EOB). The radiochemical purity was > 99%, and the specific activity at EOB was 370-1110 GBq/mu mol with a total synthesis time of similar to 40-min from EOB. (C) 2015 Elsevier Ltd. All rights reserved.
Author	Xu, Zhidong Wang, Min Gao, Mingzhang Zheng, Qi-Huang
Author_xml	– sequence: 1 givenname: Min surname: Wang fullname: Wang, Min organization: Department of Radiology and Imaging Sciences, Indiana University School of Medicine, 1345 West 16th Street, Room 202, Indianapolis, IN 46202, USA – sequence: 2 givenname: Mingzhang surname: Gao fullname: Gao, Mingzhang organization: Department of Radiology and Imaging Sciences, Indiana University School of Medicine, 1345 West 16th Street, Room 202, Indianapolis, IN 46202, USA – sequence: 3 givenname: Zhidong surname: Xu fullname: Xu, Zhidong organization: Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of Ministry of Education, College of Chemistry and Environmental Science, Hebei University, Baoding, Hebei 071002, China – sequence: 4 givenname: Qi-Huang surname: Zheng fullname: Zheng, Qi-Huang email: qzheng@iupui.edu organization: Department of Radiology and Imaging Sciences, Indiana University School of Medicine, 1345 West 16th Street, Room 202, Indianapolis, IN 46202, USA
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Keywords	Positron emission tomography (PET) Alzheimer’s disease (AD) Tau tracer [11C]PBB3 Radiosynthesis ROUTE RADIOLIGAND FULLY AUTOMATED SYNTHESIS ACROLEIN-DIETHYL-ACETAL NEUROFIBRILLARY PATHOLOGY Alzheimer's disease (AD) RADIOTRACERS PROBES [C-11]PBB3 1ST RADIOSYNTHESIS AGENTS CINNAMALDEHYDES [C]PBB3
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Snippet	[Display omitted] The authentic standard PBB3 and its precursor N-desmethyl-PBB3 as well as TBS-protected N-desmethyl-PBB3 precursor for radiolabeling were... The authentic standard PBB3 and its precursor N-desmethyl-PBB3 as well as TBS-protected N-desmethyl-PBB3 precursor for radiolabeling were synthesized from...
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SubjectTerms	[11C]PBB3 Alzheimer Disease - diagnosis Alzheimer Disease - metabolism Alzheimer’s disease (AD) Aminopyridines - chemical synthesis Aminopyridines - chemistry Benzothiazoles - chemical synthesis Benzothiazoles - chemistry Carbon Radioisotopes Chemistry Chemistry, Medicinal Chemistry, Organic Humans Life Sciences & Biomedicine Molecular Imaging Molecular Structure Pharmacology & Pharmacy Physical Sciences Positron emission tomography (PET) Positron-Emission Tomography Radiosynthesis Science & Technology tau Proteins - analysis Tau tracer
Title	Synthesis of a PET tau tracer [11C]PBB3 for imaging of Alzheimer’s disease
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