Expanding the Applicability of the Metal Labeling of Biomolecules by the RIKEN Click Reaction: A Case Study with Gallium-68 Positron Emission Tomography

Yuka Nakamoto; Ambara R Pradipta; Hidefumi Mukai; Maki Zouda; Yasuyoshi Watanabe; Almira Kurbangalieva; Peni Ahmadi; Yoshiyuki Manabe; Koichi Fukase; Katsunori Tanaka

doi:10.1002/cbic.201800335

Expanding the Applicability of the Metal Labeling of Biomolecules by the RIKEN Click Reaction: A Case Study with Gallium-68 Positron Emission Tomography

Chembiochem. 2018 Oct 4;19(19):2055-2060. doi: 10.1002/cbic.201800335. Epub 2018 Sep 14.

Authors

Affiliations

¹ Department of Chemistry, Graduate School of Science, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka, 560-0043, Japan.
² Biofunctional Synthetic Chemistry Laboratory, RIKEN Cluster for Pioneering Research, 2-1 Hirosawa, Wako, Saitama, 351-0198, Japan.
³ Laboratory for Molecular Delivery and Imaging Technology, RIKEN Center for Biosystems Dynamics Research, 6-7-3 Minatojima-minamimachi, Chuo-ku, Kobe, Hyogo, 650-0047, Japan.
⁴ Laboratory for Pathophysiological and Health Science, RIKEN Center for Biosystems Dynamics Research, 6-7-3 Minatojima-minamimachi, Chuo-ku, Kobe, Hyogo, 650-0047, Japan.
⁵ Biofunctional Chemistry Laboratory, Butlerov Institute of Chemistry, Kazan Federal University, 18 Kremlyovskaya Street, Kazan, 420008, Russia.
⁶ GlycoTargeting Research Laboratory, RIKEN Baton Zone Program, 2-1 Hirosawa, Wako, Saitama, 351-0198, Japan.

PMID: 30066425
DOI: 10.1002/cbic.201800335

Abstract

Radiolabeled biomolecules with short half-life times are of increasing importance for positron emission tomography (PET) imaging studies. Herein, we demonstrate an improved and generalized method for synthesizing a [radiometal]-unsaturated aldehyde as a lysine-labeling probe that can be easily conjugated into various biomolecules through the RIKEN click reaction. As a case study, ⁶⁸ Ga-PET imaging of U87MG xenografted mice is demonstrated by using the ⁶⁸ Ga-DOTA-RGDyK peptide, which is selective to α_V β₃ integrins.

Keywords: biomolecules; click chemistry; gallium; positron emission tomography; radiopharmaceuticals.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Cell Line, Tumor
Gallium Radioisotopes / chemistry
Gallium Radioisotopes / pharmacokinetics*
Heterografts
Humans
Integrin alphaVbeta3 / metabolism
Mice
Mice, Inbred BALB C
Peptides / chemistry
Peptides / pharmacokinetics*
Positron-Emission Tomography / methods*
Radiopharmaceuticals / pharmacokinetics*
Tissue Distribution

Substances

Gallium Radioisotopes
Integrin alphaVbeta3
Peptides
Radiopharmaceuticals
Gallium-68