Literature DB >> 20862423

Tetrazine-trans-cyclooctene ligation for the rapid construction of 18F labeled probes.

Zibo Li1, Hancheng Cai, Matthew Hassink, Melissa L Blackman, Richard C D Brown, Peter S Conti, Joseph M Fox.   

Abstract

A radiolabeling method for bioconjugation based on the Diels-Alder reaction between 3,6-diaryl-s-tetrazines and an (18)F-labeled trans-cyclooctene is described. The reaction proceeds with exceptionally fast rates, making it an effective conjugation method within seconds at low micromolar concentrations.

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Year:  2010        PMID： 20862423      PMCID： PMC3230320          DOI： 10.1039/c0cc03078c

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


  16 in total

Review 1.  PET tracers and radiochemistry.

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Journal:  Ann Acad Med Singapore       Date:  2004-03       Impact factor: 2.473

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Journal:  Angew Chem Int Ed Engl       Date:  2010-04-26       Impact factor: 15.336

Review 3.  Bioorthogonal chemistry: recent progress and future directions.

Authors:  Reyna K V Lim; Qing Lin
Journal:  Chem Commun (Camb)       Date:  2010-01-21       Impact factor: 6.222

4.  Bioorthogonal turn-on probes for imaging small molecules inside living cells.

Authors:  Neal K Devaraj; Scott Hilderbrand; Rabi Upadhyay; Ralph Mazitschek; Ralph Weissleder
Journal:  Angew Chem Int Ed Engl       Date:  2010-03-19       Impact factor: 15.336

Review 5.  Cu-free click cycloaddition reactions in chemical biology.

Authors:  John C Jewett; Carolyn R Bertozzi
Journal:  Chem Soc Rev       Date:  2010-04       Impact factor: 54.564

6.  Tetrazine-based cycloadditions: application to pretargeted live cell imaging.

Authors:  Neal K Devaraj; Ralph Weissleder; Scott A Hilderbrand
Journal:  Bioconjug Chem       Date:  2008-12       Impact factor: 4.774

7.  Fast and sensitive pretargeted labeling of cancer cells through a tetrazine/trans-cyclooctene cycloaddition.

Authors:  Neal K Devaraj; Rabi Upadhyay; Jered B Haun; Scott A Hilderbrand; Ralph Weissleder
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

8.  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

9.  Click chemistry beyond metal-catalyzed cycloaddition.

Authors:  C Remzi Becer; Richard Hoogenboom; Ulrich S Schubert
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

10.  A photochemical synthesis of functionalized trans-cyclooctenes driven by metal complexation.

Authors:  Maksim Royzen; Glenn P A Yap; Joseph M Fox
Journal:  J Am Chem Soc       Date:  2008-03-06       Impact factor: 15.419
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  65 in total

1.  Bioorthogonal reaction pairs enable simultaneous, selective, multi-target imaging.

Authors:  Mark R Karver; Ralph Weissleder; Scott A Hilderbrand
Journal:  Angew Chem Int Ed Engl       Date:  2011-12-12       Impact factor: 15.336

2.  Synthesis and evaluation of a series of 1,2,4,5-tetrazines for bioorthogonal conjugation.

Authors:  Mark R Karver; Ralph Weissleder; Scott A Hilderbrand
Journal:  Bioconjug Chem       Date:  2011-10-24       Impact factor: 4.774

Review 3.  Click Reaction: An Applicable Radiolabeling Method for Molecular Imaging.

Authors:  Ji Young Choi; Byung Chul Lee
Journal:  Nucl Med Mol Imaging       Date:  2015-10-19

Review 4.  Expanding room for tetrazine ligations in the in vivo chemistry toolbox.

Authors:  Jolita Sečkutė; Neal K Devaraj
Journal:  Curr Opin Chem Biol       Date:  2013-09-07       Impact factor: 8.822

5.  Genetically encoded tetrazine amino acid directs rapid site-specific in vivo bioorthogonal ligation with trans-cyclooctenes.

Authors:  Jason L Seitchik; Jennifer C Peeler; Michael T Taylor; Melissa L Blackman; Timothy W Rhoads; Richard B Cooley; Christian Refakis; Joseph M Fox; Ryan A Mehl
Journal:  J Am Chem Soc       Date:  2012-02-01       Impact factor: 15.419

6.  Preparation and Evaluation of 99mTc-labeled Tridentate Chelates for Pre-targeting Using Bioorthogonal Chemistry.

Authors:  Holly A Bilton; Zainab Ahmad; Nancy Janzen; Shannon Czorny; John F Valliant
Journal:  J Vis Exp       Date:  2017-02-04       Impact factor: 1.355

7.  68Ga chelating bioorthogonal tetrazine polymers for the multistep labeling of cancer biomarkers.

Authors:  Brandon Nichols; Zhengtao Qin; Jun Yang; David R Vera; Neal K Devaraj
Journal:  Chem Commun (Camb)       Date:  2014-03-04       Impact factor: 6.222

8.  Large-Scale Flow Photochemical Synthesis of Functionalized trans-Cyclooctenes Using Sulfonated Silica Gel.

Authors:  Ampofo Darko; Samantha J Boyd; Joseph M Fox
Journal:  Synthesis (Stuttg)       Date:  2018-12       Impact factor: 3.157

9.  Efficient method for site-specific 18F-labeling of biomolecules using the rapid condensation reaction between 2-cyanobenzothiazole and cysteine.

Authors:  Jongho Jeon; Bin Shen; Liqin Xiong; Zheng Miao; Kyung Hyun Lee; Jianghong Rao; Frederick T Chin
Journal:  Bioconjug Chem       Date:  2012-08-10       Impact factor: 4.774

10.  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
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