Issue 36, 2023

1-(N,N-Dialkylcarbamoyl)-1,1-difluoromethanesulfonyl ester as a stable and effective precursor for a neopentyl labeling group with astatine-211

Abstract

Radiohalogens with a short half-life are useful radioisotopes for radiotheranostics. Astatine-211 is an α-emitting radiohalogen and is expected to be applicable to targeted α therapy. A neopentyl labeling group is an effective hydrophilic labeling unit for various radiohalogens, which includes 211At. In this study, a 1-(N,N-dialkylcarbamoyl)-1,1-difluoromethanesulfonyl (CDf) ester was developed as a stable precursor for labeling with 211At, 77Br and 125I through a neopentyl labeling group. The CDf ester remained stable in an acetonitrile solution at room temperature and enabled the successful syntheses of 211At-labeled compounds in a highly radiochemical conversion in the presence of K2CO3. 77Br- and 125I-labeled compounds can be prepared from the CDf ester without a base. The utility of the CDf ester was demonstrated in the synthesis of a benzylguanidine with a neopentyl 211At-labeling group. The developed method afforded a 32% radiochemical yield of 211At-labeled benzylguanidine. However, a partial deastatination was observed under acidic conditions during the removal of an N-Boc protecting group. Deprotecting these groups under milder acidic conditions may improve the radiochemical yield. In conclusion, the CDf ester facilitates the syntheses of 211At, 125I and 77Br-labeled compounds that use a neopentyl labeling group for radiotheranostic applications. Further optimization of protecting groups and reaction conditions should enhance the total radiochemical yield of the 211At-labeled compounds.

Graphical abstract: 1-(N,N-Dialkylcarbamoyl)-1,1-difluoromethanesulfonyl ester as a stable and effective precursor for a neopentyl labeling group with astatine-211

Supplementary files

Article information

Article type
Paper
Submitted
15 Jun 2023
Accepted
07 Aug 2023
First published
07 Aug 2023

Org. Biomol. Chem., 2023,21, 7467-7472

Author version available

1-(N,N-Dialkylcarbamoyl)-1,1-difluoromethanesulfonyl ester as a stable and effective precursor for a neopentyl labeling group with astatine-211

I. Sasaki, M. Tada, Z. Liu, M. Tatsuta, T. Okura, M. Aoki, K. Takahashi, N. S. Ishioka, S. Watanabe and H. Tanaka, Org. Biomol. Chem., 2023, 21, 7467 DOI: 10.1039/D3OB00944K

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