Literature DB >> 29170778

[18F]ODIBO: a prosthetic group for bioorthogonal radiolabeling of macromolecules via strain-promoted alkyne-azide cycloaddition.

Mehdi Boudjemeline1, Christopher D McNitt, Thomas A Singleton, Vladimir V Popik, Alexey P Kostikov.   

Abstract

A novel prosthetic group for the efficient radiolabeling of macromolecules has been developed. [18F]oxadibenzocyclooctyne ([18F]ODIBO) is synthesized in high radiochemical yield and applied for nearly quantitative conjugation to azide-tagged peptides and proteins at room temperature and low substrate concentrations. The resulting bioconjugates are chemically and radiochemically pure and free of toxic solvents and catalysts.

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Year:  2018        PMID： 29170778      PMCID： PMC5999037          DOI： 10.1039/c7ob02532g

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  18 in total

1.  Click Chemistry: Diverse Chemical Function from a Few Good Reactions.

Authors:  Hartmuth C. Kolb; M. G. Finn; K. Barry Sharpless
Journal:  Angew Chem Int Ed Engl       Date:  2001-06-01       Impact factor: 15.336

2.  Copper-free click chemistry with the short-lived positron emitter fluorine-18.

Authors:  Vincent Bouvet; Melinda Wuest; Frank Wuest
Journal:  Org Biomol Chem       Date:  2011-09-22       Impact factor: 3.876

3.  Strain-promoted copper-free "click" chemistry for 18F radiolabeling of bombesin.

Authors:  Lachlan S Campbell-Verduyn; Leila Mirfeizi; Anne K Schoonen; Rudi A Dierckx; Philip H Elsinga; Ben L Feringa
Journal:  Angew Chem Int Ed Engl       Date:  2011-09-28       Impact factor: 15.336

Review 4.  Bioorthogonal chemistry for pre-targeted molecular imaging--progress and prospects.

Authors:  Laurence Carroll; Helen L Evans; Eric O Aboagye; Alan C Spivey
Journal:  Org Biomol Chem       Date:  2013-09-21       Impact factor: 3.876

5.  Copper-Free Click for PET: Rapid 1,3-Dipolar Cycloadditions with a Fluorine-18 Cyclooctyne.

Authors:  Richard D Carpenter; Sven H Hausner; Julie L Sutcliffe
Journal:  ACS Med Chem Lett       Date:  2011-10-07       Impact factor: 4.345

6.  Rate determination of azide click reactions onto alkyne polymer brush scaffolds: a comparison of conventional and catalyst-free cycloadditions for tunable surface modification.

Authors:  Sara V Orski; Gareth R Sheppard; Selvanathan Arumugam; Rachelle M Arnold; Vladimir V Popik; Jason Locklin
Journal:  Langmuir       Date:  2012-10-05       Impact factor: 3.882

Review 7.  The inverse electron demand Diels-Alder click reaction in radiochemistry.

Authors:  Thomas Reiner; Brian M Zeglis
Journal:  J Labelled Comp Radiopharm       Date:  2013-12-18       Impact factor: 1.921

Review 8.  Copper toxicity, oxidative stress, and antioxidant nutrients.

Authors:  Lisa M Gaetke; Ching Kuang Chow
Journal:  Toxicology       Date:  2003-07-15       Impact factor: 4.221

9.  DNA-fiber EPR spectroscopy as a tool to study DNA-metal complex interactions: DNA binding of hydrated Cu(II) ions and Cu(II) complexes of amino acids and peptides.

Authors:  Makoto Chikira
Journal:  J Inorg Biochem       Date:  2008-01-26       Impact factor: 4.155

10.  Highly reactive trans-cyclooctene tags with improved stability for Diels-Alder chemistry in living systems.

Authors:  Raffaella Rossin; Sandra M van den Bosch; Wolter Ten Hoeve; Marco Carvelli; Ron M Versteegen; Johan Lub; Marc S Robillard
Journal:  Bioconjug Chem       Date:  2013-06-18       Impact factor: 4.774
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  4 in total

1.  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

2.  A strained alkyne-containing bipyridine reagent; synthesis, reactivity and fluorescence properties.

Authors:  Sam Forshaw; Richard C Knighton; Jami Reber; Jeremy S Parker; Nikola P Chmel; Martin Wills
Journal:  RSC Adv       Date:  2019-11-06       Impact factor: 4.036

3.  Nitrone-Modified Gold Nanoparticles: Synthesis, Characterization, and Their Potential as 18F-Labeled Positron Emission Tomography Probes via I-SPANC.

Authors:  Sara Ghiassian; Lihai Yu; Pierangelo Gobbo; Ali Nazemi; Tommaso Romagnoli; Wilson Luo; Leonard G Luyt; Mark S Workentin
Journal:  ACS Omega       Date:  2019-11-08

Review 4.  Recent Advances in Bioorthogonal Click Chemistry for Efficient Synthesis of Radiotracers and Radiopharmaceuticals.

Authors:  Sajid Mushtaq; Seong-Jae Yun; Jongho Jeon
Journal:  Molecules       Date:  2019-10-02       Impact factor: 4.411
  4 in total

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