Literature DB >> 27008570

Site-Specific Radiofluorination of Biomolecules with 8-[(18)F]-Fluorooctanoic Acid Catalyzed by Lipoic Acid Ligase.

Christopher R Drake1, Natalia Sevillano2, Charles Truillet1, Charles S Craik2, Henry F VanBrocklin1, Michael J Evans1.   

Abstract

New methodologies for site-specifically radiolabeling proteins with (18)F are required to generate high quality radiotracers for preclinical and clinical applications with positron emission tomography. Herein, we report an approach by which we use lipoic acid ligase (LplA) to conjugate [(18)F]-fluorooctanoic acid to an antibody fragment bearing the peptide substrate of LplA. The mild conditions of the reaction preserve antibody immunoreactivity, and the efficiency of LplA allows for >90% yield even with very small amounts of peptidic precursor (1-10 nmol). These features are advantageous compared to the current gold standard in the field. Moreover, the methodology introduces a new application for an important tool in chemical biology.

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Year:  2016        PMID: 27008570      PMCID: PMC5712215          DOI: 10.1021/acschembio.6b00172

Source DB:  PubMed          Journal:  ACS Chem Biol        ISSN: 1554-8929            Impact factor:   5.100


  36 in total

1.  A fluorophore ligase for site-specific protein labeling inside living cells.

Authors:  Chayasith Uttamapinant; Katharine A White; Hemanta Baruah; Samuel Thompson; Marta Fernández-Suárez; Sujiet Puthenveetil; Alice Y Ting
Journal:  Proc Natl Acad Sci U S A       Date:  2010-06-07       Impact factor: 11.205

2.  Sonogashira cross-coupling reaction with 4-[18F]fluoroiodobenzene for rapid 18F-labelling of peptides.

Authors:  Jenilee D Way; Cody Bergman; Frank Wuest
Journal:  Chem Commun (Camb)       Date:  2015-03-04       Impact factor: 6.222

3.  Diels-Alder cycloaddition for fluorophore targeting to specific proteins inside living cells.

Authors:  Daniel S Liu; Anupong Tangpeerachaikul; Ramajeyam Selvaraj; Michael T Taylor; Joseph M Fox; Alice Y Ting
Journal:  J Am Chem Soc       Date:  2012-01-05       Impact factor: 15.419

4.  Optimization of a Pretargeted Strategy for the PET Imaging of Colorectal Carcinoma via the Modulation of Radioligand Pharmacokinetics.

Authors:  Brian M Zeglis; Christian Brand; Dalya Abdel-Atti; Kathryn E Carnazza; Brendon E Cook; Sean Carlin; Thomas Reiner; Jason S Lewis
Journal:  Mol Pharm       Date:  2015-08-31       Impact factor: 4.939

5.  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

6.  A pretargeted PET imaging strategy based on bioorthogonal Diels-Alder click chemistry.

Authors:  Brian M Zeglis; Kuntal K Sevak; Thomas Reiner; Priya Mohindra; Sean D Carlin; Pat Zanzonico; Ralph Weissleder; Jason S Lewis
Journal:  J Nucl Med       Date:  2013-05-24       Impact factor: 10.057

7.  Site-specific (18)F-labeling of the protein hormone leptin using a general two-step ligation procedure.

Authors:  Robert R Flavell; Paresh Kothari; Maya Bar-Dagan; Michael Synan; Shankar Vallabhajosula; Jeffrey M Friedman; Tom W Muir; Giovanni Ceccarini
Journal:  J Am Chem Soc       Date:  2008-06-21       Impact factor: 15.419

8.  Small-animal PET imaging of human epidermal growth factor receptor type 2 expression with site-specific 18F-labeled protein scaffold molecules.

Authors:  Zhen Cheng; Omayra Padilla De Jesus; Mohammad Namavari; Abhijit De; Jelena Levi; Jack Matt Webster; Rong Zhang; Brian Lee; Faisal A Syud; Sanjiv Sam Gambhir
Journal:  J Nucl Med       Date:  2008-04-15       Impact factor: 10.057

9.  Direct radiolabelling of proteins at cysteine using [18F]-fluorosugars.

Authors:  Omar Boutureira; Gonçalo J L Bernardes; François D'Hooge; Benjamin G Davis
Journal:  Chem Commun (Camb)       Date:  2011-08-11       Impact factor: 6.222

10.  A localized tolerance in the substrate specificity of the fluorinase enzyme enables "last-step" 18F fluorination of a RGD peptide under ambient aqueous conditions.

Authors:  Stephen Thompson; Qingzhi Zhang; Mayca Onega; Stephen McMahon; Ian Fleming; Sharon Ashworth; James H Naismith; Jan Passchier; David O'Hagan
Journal:  Angew Chem Int Ed Engl       Date:  2014-07-02       Impact factor: 15.336

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  9 in total

Review 1.  18 F-Labeling of Sensitive Biomolecules for Positron Emission Tomography.

Authors:  Hema S Krishnan; Longle Ma; Neil Vasdev; Steven H Liang
Journal:  Chemistry       Date:  2017-09-01       Impact factor: 5.236

2.  Further assessments of ligase LplA-mediated modifications of proteins in vitro and in cellulo.

Authors:  Alicia Schirer; Anne Rouch; Estelle Marcheteau; Johann Stojko; Elodie Jeantet; Benjamin Fould; Gilles Ferry; Jean A Boutin
Journal:  Mol Biol Rep       Date:  2021-10-31       Impact factor: 2.316

Review 3.  Recent progress in enzymatic protein labelling techniques and their applications.

Authors:  Yi Zhang; Keun-Young Park; Kiall F Suazo; Mark D Distefano
Journal:  Chem Soc Rev       Date:  2018-09-27       Impact factor: 54.564

4.  ImmunoPET: Concept, Design, and Applications.

Authors:  Weijun Wei; Zachary T Rosenkrans; Jianjun Liu; Gang Huang; Quan-Yong Luo; Weibo Cai
Journal:  Chem Rev       Date:  2020-03-23       Impact factor: 60.622

Review 5.  Enzymatic Methods for the Site-Specific Radiolabeling of Targeting Proteins.

Authors:  Cristina Bolzati; Barbara Spolaore
Journal:  Molecules       Date:  2021-06-08       Impact factor: 4.411

Review 6.  From Synthesis to Characterization of Site-Selective PEGylated Proteins.

Authors:  Lisandra Herrera Belén; Carlota de Oliveira Rangel-Yagui; Jorge F Beltrán Lissabet; Brian Effer; Manuel Lee-Estevez; Adalberto Pessoa; Rodrigo L Castillo; Jorge G Farías
Journal:  Front Pharmacol       Date:  2019-12-18       Impact factor: 5.810

Review 7.  Designing Functional Bionanoconstructs for Effective In Vivo Targeting.

Authors:  Aisling Fleming; Lorenzo Cursi; James A Behan; Yan Yan; Zengchun Xie; Laurent Adumeau; Kenneth A Dawson
Journal:  Bioconjug Chem       Date:  2022-02-15       Impact factor: 4.774

Review 8.  Nanobodies as non-invasive imaging tools.

Authors:  M Rashidian; H Ploegh
Journal:  Immunooncol Technol       Date:  2020-07-09

Review 9.  Antibody Fragment and Affibody ImmunoPET Imaging Agents: Radiolabelling Strategies and Applications.

Authors:  Ruisi Fu; Laurence Carroll; Gokhan Yahioglu; Eric O Aboagye; Philip W Miller
Journal:  ChemMedChem       Date:  2018-11-15       Impact factor: 3.466

  9 in total

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