Development of <sup>18</sup>F-Labeled hydrophilic <i>trans</i>-cyclooctene as a bioorthogonal tool for PET probe construction

Xu, Muyun; Ma, Xinrui; Pigga, Jessica E.; Zhang, He; Wang, Shuli; Zhao, Weiling; Deng, Huaifu; Wu, Anna M.; Liu, Rihe; Wu, Zhanhong; Fox, Joseph M.; Li, Zibo

doi:10.1039/d3cc04212j

Chem. Commun.

2023

DOI: 10.1039/d3cc04212j

|View full text |Cite

Development of ¹⁸F-Labeled hydrophilic trans-cyclooctene as a bioorthogonal tool for PET probe construction

Muyun Xu,

Xinrui Ma,

Jessica E. Pigga

et al.

Abstract: Trans-cyclooctene (TCO) tetrazine ligation has become one of the fastest bioorthogonal reactions in the field, making it increasingly useful for PET imaging applications. However, the high hydrophobicity of 18F-labeled TCO...

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...

Citation Types

Supporting

Mentioning

Contrasting

Year Published

2024

Publication Types

Select...

Article1

Relationship

Self Cite0

Independent1

Authors

Journals

Cited by 1 publication

References 39 publications

(71 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

Hetero-Diels–Alder and CuAAC Click Reactions for Fluorine-18 Labeling of Peptides: Automation and Comparative Study of the Two Methods

Maujean,

Ramanoudjame,

Riché

et al. 2024

Molecules

View full text Add to dashboard Cite

Radiolabeled peptides are valuable tools for diagnosis or therapies; they are often radiofluorinated using an indirect approach based on an F-18 prosthetic group. Herein, we are reporting our results on the F-18 radiolabeling of three peptides using two different methods based on click reactions. The first one used the well-known CuAAC reaction, and the second one is based on our recently reported hetero-Diels–Alder (HDA) using a dithioesters (thia-Diels–Alder) reaction. Both methods have been automated, and the 18F-peptides were obtained in similar yields and synthesis time (37–39% decay corrected yields by both methods in 120–140 min). However, to obtain similar yields, the CuAAC needs a large amount of copper along with many additives, while the HDA is a catalyst and metal-free reaction necessitating only an appropriate ratio of water/ethanol. The HDA can therefore be considered as a minimalist method offering easy access to fluorine-18 labeled peptides and making it a valuable additional tool for the indirect and site-specific labeling of peptides or biomolecules.

show abstract

Hetero-Diels–Alder and CuAAC Click Reactions for Fluorine-18 Labeling of Peptides: Automation and Comparative Study of the Two Methods

Maujean,

Ramanoudjame,

Riché

et al. 2024

Molecules

View full text Add to dashboard Cite

show abstract

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

customersupport@researchsolutions.com

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

Development of ¹⁸F-Labeled hydrophilic trans-cyclooctene as a bioorthogonal tool for PET probe construction

Abstract: Trans-cyclooctene (TCO) tetrazine ligation has become one of the fastest bioorthogonal reactions in the field, making it increasingly useful for PET imaging applications. However, the high hydrophobicity of 18F-labeled TCO...

Cited by 1 publication

References 39 publications

Hetero-Diels–Alder and CuAAC Click Reactions for Fluorine-18 Labeling of Peptides: Automation and Comparative Study of the Two Methods

Hetero-Diels–Alder and CuAAC Click Reactions for Fluorine-18 Labeling of Peptides: Automation and Comparative Study of the Two Methods

Contact Info

Product

Resources

About

Development of 18F-Labeled hydrophilic trans-cyclooctene as a bioorthogonal tool for PET probe construction

Abstract: Trans-cyclooctene (TCO) tetrazine ligation has become one of the fastest bioorthogonal reactions in the field, making it increasingly useful for PET imaging applications. However, the high hydrophobicity of 18F-labeled TCO...

Cited by 1 publication

References 39 publications

Hetero-Diels–Alder and CuAAC Click Reactions for Fluorine-18 Labeling of Peptides: Automation and Comparative Study of the Two Methods

Hetero-Diels–Alder and CuAAC Click Reactions for Fluorine-18 Labeling of Peptides: Automation and Comparative Study of the Two Methods

Contact Info

Product

Resources

About

Development of ¹⁸F-Labeled hydrophilic trans-cyclooctene as a bioorthogonal tool for PET probe construction