» Articles » PMID: 29170778

[F]ODIBO: a Prosthetic Group for Bioorthogonal Radiolabeling of Macromolecules Via Strain-promoted Alkyne-azide Cycloaddition

Overview
Journal Org Biomol Chem
Specialties Biochemistry
Chemistry
Date 2017 Nov 25
PMID 29170778
Citations 6
Authors
Affiliations
Soon will be listed here.
Abstract

A novel prosthetic group for the efficient radiolabeling of macromolecules has been developed. [F]oxadibenzocyclooctyne ([F]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.

Citing Articles

Templated Generation of a Bcl-x Inhibitor by Isomer-Free SPAAC Based on Azacyclonon-5-yne.

Brauer J, Motzing M, Grost C, Hoffmann R, Berg T Chemistry. 2022; 28(66):e202202259.

PMID: 35989238 PMC: 9827882. DOI: 10.1002/chem.202202259.


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

Forshaw S, Knighton R, Reber J, Parker J, Chmel N, Wills M RSC Adv. 2022; 9(62):36154-36161.

PMID: 35540623 PMC: 9074932. DOI: 10.1039/c9ra06866j.


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

Ghiassian S, Yu L, Gobbo P, Nazemi A, Romagnoli T, Luo W ACS Omega. 2019; 4(21):19106-19115.

PMID: 31763533 PMC: 6868604. DOI: 10.1021/acsomega.9b02322.


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

Mushtaq S, Yun S, Jeon J Molecules. 2019; 24(19).

PMID: 31581645 PMC: 6803924. DOI: 10.3390/molecules24193567.


Synthesis and Reactivity of a Bis-Strained Alkyne Derived from 1,1'-Biphenyl-2,2',6,6'-tetrol.

Knighton R, Sharma K, Robertson N, Spring D, Wills M ACS Omega. 2019; 4(1):2160-2167.

PMID: 31459462 PMC: 6648819. DOI: 10.1021/acsomega.8b03634.


References
1.
Gaetke L, Chow C . Copper toxicity, oxidative stress, and antioxidant nutrients. Toxicology. 2003; 189(1-2):147-63. DOI: 10.1016/s0300-483x(03)00159-8. View

2.
Campbell-Verduyn L, Mirfeizi L, Schoonen A, Dierckx R, Elsinga P, Feringa B . Strain-promoted copper-free "click" chemistry for 18F radiolabeling of bombesin. Angew Chem Int Ed Engl. 2011; 50(47):11117-20. DOI: 10.1002/anie.201105547. View

3.
Chikira M . 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. J Inorg Biochem. 2008; 102(5-6):1016-24. DOI: 10.1016/j.jinorgbio.2008.01.019. View

4.
Rossin R, van den Bosch S, Ten Hoeve W, Carvelli M, Versteegen R, Lub J . Highly reactive trans-cyclooctene tags with improved stability for Diels-Alder chemistry in living systems. Bioconjug Chem. 2013; 24(7):1210-7. DOI: 10.1021/bc400153y. View

5.
Carpenter R, Hausner S, Sutcliffe J . Copper-Free Click for PET: Rapid 1,3-Dipolar Cycloadditions with a Fluorine-18 Cyclooctyne. ACS Med Chem Lett. 2014; 2(12):885-9. PMC: 4018166. DOI: 10.1021/ml200187j. View