Literature DB >> 20965741

Automated radiochemical synthesis of [18F]FBEM: a thiol reactive synthon for radiofluorination of peptides and proteins.

Dale O Kiesewetter1, Orit Jacobson, Lixin Lang, Xiaoyuan Chen.   

Abstract

The automated radiochemical synthesis of N-[2-(4-[(18)F]fluorobenzamido)ethyl]maleimide ([(18)F]FBEM, IUPAC name: N-maleoylethyl-4-[(18)F]fluorobenzamide), a prosthetic group for radiolabeling the free sulfhydryl groups of peptides and proteins, is herein described. 4-[(18)F]fluorobenzoic acid was first prepared by nucleophilic displacement of a trimethylammonium moiety on a pentamethylbenzyl benzoate ester with [(18)F]fluoride. In the second step the ester was cleaved under acidic conditions. Finally, 4-[(18)F]fluorobenzoic acid was coupled to N-(2-aminoethyl)maleimide using diethylcyanophosphate and diisopropylethyl amine. Following high-performance liquid chromatography (HPLC) purification, [(18)F]FBEM was obtained in 17.3±7.1% yield (not decay corrected) in approximately 95 min. Isolation from the HPLC eluate and preparation for subsequent use, which was conducted manually, required an additional 10-15 min. The measured specific activity for three batches was 181.3, 251.6, and 351.5 GBq/μmol at the end of bombardment (EOB). Published by Elsevier Ltd.

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Year:  2010        PMID： 20965741      PMCID： PMC3010425          DOI： 10.1016/j.apradiso.2010.09.023

Source DB:  PubMed          Journal:  Appl Radiat Isot        ISSN： 0969-8043            Impact factor:   1.513


  12 in total

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3.  A thiol-reactive 18F-labeling agent, N-[2-(4-18F-fluorobenzamido)ethyl]maleimide, and synthesis of RGD peptide-based tracer for PET imaging of alpha v beta 3 integrin expression.

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4.  Labeling of low-density lipoproteins using the 18F-labeled thiol-reactive reagent N-[6-(4-[18F]fluorobenzylidene)aminooxyhexyl]maleimide.

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5.  Automated synthesis of 18F analogue of paclitaxel (PAC): [18F]Paclitaxel (FPAC).

Authors:  Joseph D Kalen; Jerry I Hirsch; Karen A Kurdziel; William C Eckelman; Dale O Kiesewetter
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6.  Synthesis of N-succinimidyl 4-[18F]fluorobenzoate, an agent for labeling proteins and peptides with 18F.

Authors:  Ganesan Vaidyanathan; Michael R Zalutsky
Journal:  Nat Protoc       Date:  2006       Impact factor: 13.491

7.  Direct one-step 18F-labeling of peptides via nucleophilic aromatic substitution.

Authors:  Jessica Becaud; Linjing Mu; Mylène Karramkam; Pius A Schubiger; Simon M Ametamey; Keith Graham; Timo Stellfeld; Lutz Lehmann; Sandra Borkowski; Dietmar Berndorff; Ludger Dinkelborg; Ananth Srinivasan; René Smits; Beate Koksch
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Authors:  Tatsushi Toyokuni; Joseph C Walsh; Alan Dominguez; Michael E Phelps; Jorge R Barrio; Sanjiv S Gambhir; Nagichettiar Satyamurthy
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Authors:  Dale O Kiesewetter; Gabriela Krämer-Marek; Ying Ma; Jacek Capala
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  26 in total

1.  PET of insulinoma using ¹⁸F-FBEM-EM3106B, a new GLP-1 analogue.

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Journal:  Mol Pharm       Date:  2011-08-19       Impact factor: 4.939

Review 2.  18 F-Labeling of Sensitive Biomolecules for Positron Emission Tomography.

Authors:  Hema S Krishnan; Longle Ma; Neil Vasdev; Steven H Liang
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3.  3-18F-fluoropropane-1-thiol and 18F-PEG4-1-thiol: Versatile prosthetic groups for radiolabeling maleimide functionalized peptides.

Authors:  Orit Jacobson; Zhantong Wang; Guocan Yu; Ying Ma; Xiaoyuan Chen; Dale O Kiesewetter
Journal:  Bioorg Med Chem       Date:  2019-08-05       Impact factor: 3.641

4.  Automatic concentration and reformulation of PET tracers via microfluidic membrane distillation.

Authors:  Philip H Chao; Jeffery Collins; Joseph P Argus; Wei-Yu Tseng; Jason T Lee; R Michael van Dam
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5.  Advances in immuno-positron emission tomography: antibodies for molecular imaging in oncology.

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6.  Automated radiosynthesis of [18F]FBEM, a sulfhydryl site specific labeling agent for peptides and proteins.

Authors:  Keunpoong Lim; Jim Ropchan; Dale O Kiesewetter; Xiaoyuan Chen; Yiyun Huang
Journal:  Appl Radiat Isot       Date:  2018-07-29       Impact factor: 1.513

7.  N-Succinimidyl 4-[(18)F]-fluoromethylbenzoate-labeled dimeric RGD peptide for imaging tumor integrin expression.

Authors:  Weihua Li; Lixin Lang; Gang Niu; Ning Guo; Ying Ma; Dale O Kiesewetter; Baozhong Shen; Xiaoyuan Chen
Journal:  Amino Acids       Date:  2011-12-31       Impact factor: 3.520

8.  Production of diverse PET probes with limited resources: 24 18F-labeled compounds prepared with a single radiosynthesizer.

Authors:  Jeffrey Collins; Christopher M Waldmann; Christopher Drake; Roger Slavik; Noel S Ha; Maxim Sergeev; Mark Lazari; Bin Shen; Frederick T Chin; Melissa Moore; Saman Sadeghi; Michael E Phelps; Jennifer M Murphy; R Michael van Dam
Journal:  Proc Natl Acad Sci U S A       Date:  2017-10-10       Impact factor: 11.205

9.  Rapid synthesis of maleimide functionalized fluorine-18 labeled prosthetic group using "radio-fluorination on the Sep-Pak" method.

Authors:  Falguni Basuli; Xiang Zhang; Elaine M Jagoda; Peter L Choyke; Rolf E Swenson
Journal:  J Labelled Comp Radiopharm       Date:  2018-05-01       Impact factor: 1.921

10.  18F-labeled anti-human CD20 cys-diabody for same-day immunoPET in a model of aggressive B cell lymphoma in human CD20 transgenic mice.

Authors:  Kirstin A Zettlitz; Richard Tavaré; Wen-Ting K Tsai; Reiko E Yamada; Noel S Ha; Jeffrey Collins; R Michael van Dam; John M Timmerman; Anna M Wu
Journal:  Eur J Nucl Med Mol Imaging       Date:  2018-11-19       Impact factor: 9.236
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