RIKEN Center for Life Science Technologies


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Labs & Technologies

Labelling Chemistry Team

—Brightening Molecules—
Synthesis of PET molecular probes of biologically important compounds such as drug candidates, and development of novel labeling chemistry to meet the increasing demands in PET science.


* Due to the reorganization starting as new centers in April 2018, this laboratory is now belong to the Center for Biosystems Dynamics Research. As for the latest information, please see the following URL below.
> The webpage of Laboratory for Labeling Chemistry, Center for Biosystems Dynamics Research

Team Leader
Hisashi Doi  D.Sci.

〒6-7-3 Minatojima-minamimachi, Chuo-ku, Kobe, Hyogo 650-0047, Japan
Tel: +81-(0)78-304-7130


Research Area

Our team is developing the general synthetic methodology of short-lived PET molecular probes for promotion of PET molecular imaging science. With the objective of applying the potentials of organic chemistry to life science, we seek to realize the new synthetic methodology of PET molecular probes by using organometallic catalysts such as Pd, Rh, and Cu etc. As one of our main projects, we are striving toward introducing 11C into carbon frameworks of bioactive organic compounds by developing Pd0-mediated rapid C-[11C]methylations. These labeling methods provides groundbreaking synthesis for introducing the [11C]methyl group as the minimum carbon substituent into a carbon framework in the very short time of 5 minutes (Fig.1). We are currently expanding and evolving these rapid methylations from introduction of [11C]methyl group to [18F]fluoromethyl group, and furthermore developing the stoichiometry-focused 18F-labeling of oligodeoxynucleotides and peptides by the application of Click chemistry (Fig.2).

In the field of PET radiolabeling, the performance of the remote-controlled PET probe synthesizer is of key importance for realizing high quality and high yield in the synthesis of PET molecular probes. In this regard, we are also engaged in developing original PET probe synthesizers from the perspectives of not only safety and quick operation emphasized in labeling chemistry but also introducing advantages of experimental techniques ordinarily-used in organic chemistry. Thus, we seek to realize high quality RIKEN original molecular probes and establish the probe library through developing the new labeling methodology from the perspective of synthetically ideals and efficiencies based on organic chemistry (Fig.3).                                                                                                                                 

In addition, our team is responsible for production of PET drugs for human PET study in three institutions including Osaka City University Hospital.

Research Topics

Main Publications List


Synthesis of 11C-Labeled Thiamine and Fursultiamine for in Vivo Molecular Imaging of Vitamin B1 and Its Prodrug Using Positron Emission Tomography.

Doi H, Mawatari A, Kanazawa M, Nozaki S, Nomura Y, Kitayoshi T, Akimoto K, Suzuki M, Ninomiya S, Watanabe Y.
J Org Chem, 80(12), 6250-6258 (2015).

11C-Labeled Capsaicin and Its in Vivo Molecular Imaging in Rats by Positron Emission Tomography

Goto M, Mizuma H, Wada Y, Suzuki M, Watanabe Y, Onoe H, and Doi H.
Food Nutr Sci, 6(2), 216-220 (2015).

Stoichiometry-focused 18F-labeling of alkyne-substituted oligodeoxynucleotides using azido([18F]fluoromethyl)benzenes by Cu-catalyzed Huisgen reaction.

Kuboyama T, Nakahara M, Yoshino M, Cui Y, Sako T, Wada Y, Imanishi T, Obika S, Watanabe Y, Suzuki M, Doi H.
Bioorg Med Chem, 19(1), 249-255 (2011).

Rapid Methylation for the Synthesis of a 11C-Labeled Tolylisocarbacyclin Imaging the IP2 Receptor in a Living Human Brain

Suzuki, M., and Doi, H., Kato, K., Bjorkman, M., Långström, B., Watanabe, Y. and Noyori, R.
Tetrahedron, 56(42), 8263-8273 (2000).

Rapid Coupling of Methyl Iodide with Aryltributylstannanes Mediated by Palladium(0) Complexes: A General Protocol for the Synthesis of 11CH3-Labeled PET Tracers

Suzuki, M., and Doi, H., Bjorkman, M., Andersson, Y., Långström, B., Watanabe, Y. and Noyori, R.
Chem Eur J, 3(12), 2039-2042 (1997).

Member  *concurrent

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CLST was reorganized into three centers according to the RIKEN 4th Medium-Term Plan from April 1, 2018. For the latest information of Labelling Chemistry Team, please visit the following websites.

> The webpage of Laboratory for Labeling Chemistry, Center for Biosystems Dynamics Research [http://www.bdr.riken.jp/en/research/labs/doi-h/index.html]