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N-Succinimidyl 3-((4-(4-[(18)F]fluorobutyl)-1H-1,2,3-triazol-1-yl)methyl)-5-(guanidinomethyl)benzoate ([(18)F]SFBTMGMB): a residualizing label for (18)F-labeling of internalizing biomolecules.

Publication ,  Journal Article
Vaidyanathan, G; McDougald, D; Choi, J; Pruszynski, M; Koumarianou, E; Zhou, Z; Zalutsky, MR
Published in: Org Biomol Chem
January 28, 2016

Residualizing labeling methods for internalizing peptides and proteins are designed to trap the radionuclide inside the cell after intracellular degradation of the biomolecule. The goal of this work was to develop a residualizing label for the (18)F-labeling of internalizing biomolecules based on a template used successfully for radioiodination. N-Succinimidyl 3-((4-(4-[(18)F]fluorobutyl)-1H-1,2,3-triazol-1-yl)methyl)-5-(bis-Boc-guanidinomethyl)benzoate ([(18)F]SFBTMGMB-Boc2) was synthesized by a click reaction of an azide precursor and [(18)F]fluorohexyne in 8.5 ± 2.8% average decay-corrected radiochemical yield (n = 15). An anti-HER2 nanobody 5F7 was labeled with (18)F using [(18)F]SFBTMGMB ([(18)F]RL-I), obtained by the deprotection of [(18)F]SFBTMGMB-Boc2, in 31.2 ± 6.7% (n = 5) conjugation efficiency. The labeled nanobody had a radiochemical purity of >95%, bound to HER2-expressing BT474M1 breast cancer cells with an affinity of 4.7 ± 0.9 nM, and had an immunoreactive fraction of 62-80%. In summary, a novel residualizing prosthetic agent for labeling biomolecules with (18)F has been developed. An anti-HER2 nanobody was labeled using this prosthetic group with retention of affinity and immunoreactivity to HER2.

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Published In

Org Biomol Chem

DOI

EISSN

1477-0539

Publication Date

January 28, 2016

Volume

14

Issue

4

Start / End Page

1261 / 1271

Location

England

Related Subject Headings

  • Tumor Cells, Cultured
  • Succinimides
  • Receptor, erbB-2
  • Receptor, ErbB-2
  • Radiopharmaceuticals
  • Organic Chemistry
  • Molecular Structure
  • Humans
  • Guanidines
  • Female
 

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Vaidyanathan, G., McDougald, D., Choi, J., Pruszynski, M., Koumarianou, E., Zhou, Z., & Zalutsky, M. R. (2016). N-Succinimidyl 3-((4-(4-[(18)F]fluorobutyl)-1H-1,2,3-triazol-1-yl)methyl)-5-(guanidinomethyl)benzoate ([(18)F]SFBTMGMB): a residualizing label for (18)F-labeling of internalizing biomolecules. Org Biomol Chem, 14(4), 1261–1271. https://doi.org/10.1039/c5ob02258d
Vaidyanathan, Ganesan, Darryl McDougald, Jaeyeon Choi, Marek Pruszynski, Eftychia Koumarianou, Zhengyuan Zhou, and Michael R. Zalutsky. “N-Succinimidyl 3-((4-(4-[(18)F]fluorobutyl)-1H-1,2,3-triazol-1-yl)methyl)-5-(guanidinomethyl)benzoate ([(18)F]SFBTMGMB): a residualizing label for (18)F-labeling of internalizing biomolecules.Org Biomol Chem 14, no. 4 (January 28, 2016): 1261–71. https://doi.org/10.1039/c5ob02258d.
Vaidyanathan G, McDougald D, Choi J, Pruszynski M, Koumarianou E, Zhou Z, Zalutsky MR. N-Succinimidyl 3-((4-(4-[(18)F]fluorobutyl)-1H-1,2,3-triazol-1-yl)methyl)-5-(guanidinomethyl)benzoate ([(18)F]SFBTMGMB): a residualizing label for (18)F-labeling of internalizing biomolecules. Org Biomol Chem. 2016 Jan 28;14(4):1261–1271.
Journal cover image

Published In

Org Biomol Chem

DOI

EISSN

1477-0539

Publication Date

January 28, 2016

Volume

14

Issue

4

Start / End Page

1261 / 1271

Location

England

Related Subject Headings

  • Tumor Cells, Cultured
  • Succinimides
  • Receptor, erbB-2
  • Receptor, ErbB-2
  • Radiopharmaceuticals
  • Organic Chemistry
  • Molecular Structure
  • Humans
  • Guanidines
  • Female