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Synthesis of 2-deoxy-2[82Br]bromo-d-mannose and related compounds and their biodistributions in mice

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Abstract

The synthesis of 2-deoxy-2-[82Br]bromo-3,4,6-tri-O-acetyl-α-d-mannopyranosyl chloride (compound 3b) and 2-deoxy-2-[82Br]bromo-d-mannose (compound 4d), and their biodistributions in mice are described. The reaction of 3,4,6-tri-O-acetyl-d-glucal (compound 2) with unlabeled and labeled bromine chloride (compounds 1a and 1b) generated in situ from the oxidation of bromide with N-chlorosuccinimide gave unlabeled and labeled 2-deoxy-2-bromo-3,4,6-tri-O-acetyl-α-d-mannopyranosyl chloride (compounds 3a and 3b) with a radiochemical yield of 58% (chemical yield, 63%). The hydrolysis of compounds 3a and 3b with 2N HCl gave 2-deoxy-2-bromo-d-mannose (compounds 4a and 4b) with a radiochemical yield of 72%. The biodistribution of compounds 3b and 4b after injection in mice indicated that 2% of the total injected radioactivity rapidly accumulated in the brain, while 6% of the total injected radioactivity accumulated in the heart; however, the radioactivity started to decline in these two organs after 15 min.

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Authors and Affiliations

  1. Department of Chemistry, Brookhaven National Laboratory, 11973, Upton, New York, USA

    Yi-Guo Zhou, Chyng-Yann Shiue Ph.D., Alfred P. Wolf & Carroll D. Arnett

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  1. Yi-Guo Zhou
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  2. Chyng-Yann Shiue Ph.D.
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  3. Alfred P. Wolf
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  4. Carroll D. Arnett
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Visiting scholar from the School of Pharmacy, Shanghai First Medical College, People's Republic of China

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Zhou, YG., Shiue, CY., Wolf, A.P. et al. Synthesis of 2-deoxy-2[82Br]bromo-d-mannose and related compounds and their biodistributions in mice. Eur J Nucl Med 11, 252–256 (1985). https://doi.org/10.1007/BF00279079

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  • DOI: https://doi.org/10.1007/BF00279079

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