Literature DB >> 23673726

11CO2 fixation: a renaissance in PET radiochemistry.

Benjamin H Rotstein1, Steven H Liang, Jason P Holland, Thomas Lee Collier, Jacob M Hooker, Alan A Wilson, Neil Vasdev.   

Abstract

Carbon-11 labelled carbon dioxide is the cyclotron-generated feedstock reagent for most positron emission tomography (PET) tracers using this radionuclide. Most carbon-11 labels, however, are installed using derivative reagents generated from [(11)C]CO2. In recent years, [(11)C]CO2 has seen a revival in applications for the direct incorporation of carbon-11 into functional groups such as ureas, carbamates, oxazolidinones, carboxylic acids, esters, and amides. This review summarizes classical [(11)C]CO2 fixation strategies using organometallic reagents and then focuses on newly developed methods that employ strong organic bases to reversibly capture [(11)C]CO2 into solution, thereby enabling highly functionalized labelled compounds to be prepared. Labelled compounds and radiopharmaceuticals that have been translated to the clinic are highlighted.

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Year:  2013        PMID: 23673726      PMCID: PMC5604310          DOI: 10.1039/c3cc42236d

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  52 in total

1.  Rapid carbon-11 radiolabelling for PET using microfluidics.

Authors:  Philip W Miller; Hélène Audrain; Dirk Bender; Andrew J deMello; Antony D Gee; Nicholas J Long; Ramon Vilar
Journal:  Chemistry       Date:  2010-12-03       Impact factor: 5.236

Review 2.  The cannabinoid system and its pharmacological manipulation--a review, with emphasis upon the uptake and hydrolysis of anandamide.

Authors:  Christopher J Fowler
Journal:  Fundam Clin Pharmacol       Date:  2006-12       Impact factor: 2.748

Review 3.  Synthesis of 11C, 18F, 15O, and 13N radiolabels for positron emission tomography.

Authors:  Philip W Miller; Nicholas J Long; Ramon Vilar; Antony D Gee
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

4.  Discovery of PF-04457845: A Highly Potent, Orally Bioavailable, and Selective Urea FAAH Inhibitor.

Authors:  Douglas S Johnson; Cory Stiff; Scott E Lazerwith; Suzanne R Kesten; Lorraine K Fay; Mark Morris; David Beidler; Marya B Liimatta; Sarah E Smith; David T Dudley; Nalini Sadagopan; Shobha N Bhattachar; Stephen J Kesten; Tyzoon K Nomanbhoy; Benjamin F Cravatt; Kay Ahn
Journal:  ACS Med Chem Lett       Date:  2011-02-10       Impact factor: 4.345

5.  11C-labelled phosgene: an improved procedure and synthesis device.

Authors:  C Crouzel; D Roeda; M Berridge; R Knipper; D Comar
Journal:  Int J Appl Radiat Isot       Date:  1983-11

6.  No-carrier-added synthesis of [1-11C]pyruvic acid.

Authors:  M R Kilbourn; M J Welch
Journal:  Int J Appl Radiat Isot       Date:  1982-05

7.  A simplified and improved synthesis of [11C]phosgene with iron and iron (III) oxide.

Authors:  Ken-ichi Nishijima; Yuji Kuge; Koh-ichi Seki; Kazue Ohkura; Noriko Motoki; Kotaro Nagatsu; Akira Tanaka; Eriko Tsukamoto; Nagara Tamaki
Journal:  Nucl Med Biol       Date:  2002-04       Impact factor: 2.408

8.  Transition-metal-catalyzed C-C bond formation through the fixation of carbon dioxide.

Authors:  Kun Huang; Chang-Liang Sun; Zhang-Jie Shi
Journal:  Chem Soc Rev       Date:  2011-03-08       Impact factor: 54.564

9.  11C-GR103545, a radiotracer for imaging kappa-opioid receptors in vivo with PET: synthesis and evaluation in baboons.

Authors:  Peter S Talbot; Raj Narendran; Eduardo R Butelman; Yiyun Huang; Kim Ngo; Mark Slifstein; Diana Martinez; Marc Laruelle; Dah-Ren Hwang
Journal:  J Nucl Med       Date:  2005-03       Impact factor: 10.057

Review 10.  State of art in 11C labelled radiotracers synthesis.

Authors:  M Allard; E Fouquet; D James; M Szlosek-Pinaud
Journal:  Curr Med Chem       Date:  2008       Impact factor: 4.530

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  37 in total

1.  Radiosynthesis of (11)C-Levetiracetam: A Potential Marker for PET Imaging of SV2A Expression.

Authors:  Hancheng Cai; Thomas J Mangner; Otto Muzik; Ming-Wei Wang; Diane C Chugani; Harry T Chugani
Journal:  ACS Med Chem Lett       Date:  2014-08-19       Impact factor: 4.345

Review 2.  Considerations in the Development of Reversibly Binding PET Radioligands for Brain Imaging.

Authors:  Victor W Pike
Journal:  Curr Med Chem       Date:  2016       Impact factor: 4.530

Review 3.  (11)C[double bond, length as m-dash]O bonds made easily for positron emission tomography radiopharmaceuticals.

Authors:  Benjamin H Rotstein; Steven H Liang; Michael S Placzek; Jacob M Hooker; Antony D Gee; Frédéric Dollé; Alan A Wilson; Neil Vasdev
Journal:  Chem Soc Rev       Date:  2016-08-22       Impact factor: 54.564

4.  Recent applications of a single quadrupole mass spectrometer in 11C, 18F and radiometal chemistry.

Authors:  Thomas L Collier; Kenneth Dahl; Nickeisha A Stephenson; Jason P Holland; Adam Riley; Steven H Liang; Neil Vasdev
Journal:  J Fluor Chem       Date:  2018-03-05       Impact factor: 2.050

5.  High-Yielding Automated Convergent Synthesis of No-Carrier-Added [11C-Carbonyl]-Labeled Amino Acids Using the Strecker Reaction.

Authors:  Junhao Xing; Allen F Brooks; Dylan Fink; Huibin Zhang; Morand R Piert; Peter J H Scott; Xia Shao
Journal:  Synlett       Date:  2016-11-07       Impact factor: 2.454

Review 6.  Chemistry for Positron Emission Tomography: Recent Advances in 11 C-, 18 F-, 13 N-, and 15 O-Labeling Reactions.

Authors:  Xiaoyun Deng; Jian Rong; Lu Wang; Neil Vasdev; Lei Zhang; Lee Josephson; Steven H Liang
Journal:  Angew Chem Int Ed Engl       Date:  2019-01-14       Impact factor: 15.336

7.  [11C]Cyanation of arylboronic acids in aqueous solutions.

Authors:  Longle Ma; Michael S Placzek; Jacob M Hooker; Neil Vasdev; Steven H Liang
Journal:  Chem Commun (Camb)       Date:  2017-06-05       Impact factor: 6.222

8.  Radiosynthesis and ex vivo evaluation of [(11)C-carbonyl]carbamate- and urea-based monoacylglycerol lipase inhibitors.

Authors:  Justin W Hicks; Jun Parkes; Junchao Tong; Sylvain Houle; Neil Vasdev; Alan A Wilson
Journal:  Nucl Med Biol       Date:  2014-05-10       Impact factor: 2.408

9.  Kinetic modeling of the monoamine oxidase B radioligand [¹¹C]SL25.1188 in human brain with high-resolution positron emission tomography.

Authors:  Pablo M Rusjan; Alan A Wilson; Laura Miler; Ian Fan; Romina Mizrahi; Sylvain Houle; Neil Vasdev; Jeffrey H Meyer
Journal:  J Cereb Blood Flow Metab       Date:  2014-02-12       Impact factor: 6.200

10.  Synthesis and pharmacokinetic study of a 11C-labeled cholesterol 24-hydroxylase inhibitor using 'in-loop' [11C]CO2 fixation method.

Authors:  Zhen Chen; Jiahui Chen; Natalia Mast; Jian Rong; Xiaoyun Deng; Tuo Shao; Hualong Fu; Qingzhen Yu; Jiyun Sun; Yihan Shao; Lee Josephson; Thomas Lee Collier; Irina Pikuleva; Steven H Liang
Journal:  Bioorg Med Chem Lett       Date:  2020-03-06       Impact factor: 2.823

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