Centers & Labs

RIKEN Center for Life Science Technologies

Labelling Chemistry Team

Team Leader: Hisashi Doi (D.Sci.)
Hisashi  Doi(D.Sci.)

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. Especially, we focus on the labeling methods by carbon-carbon bond formation which would provide chemical and metabolic stability of PET molecular probe in in vivo system to enhance the credibility of the PET imaging. In addition, our team is working on developing 11C- or 18F-labeling methods for biomolecules such as peptides, oligonucleotide, proteins, and antibodies.

Main Research Field

Chemistry

Related Research Fields

Engineering / Biological Sciences / Medicine, dentistry, and pharmacy

Research Subjects

  • Development of PET-probe syntheses for drug candidates and novel labeling reactions
  • Development of remote-controlled synthesizers and efficient synthetic procedures for radiolabeling by organometallic chemistry
  • Development of molecular probes associated with severe diseases such as cancer, inflammation, and neurological damage

Selected Publications

  1. Doi H., Mawatari, A., Kanazawa, M., Nozaki, S., Nomura, Y., Kitayoshi, T., Akimoto, K., Suzuki, M., Ninomiya, Y. and Watanabe, Y.:
    "Synthesis of 11C-Labeled Thiamine and Fursultiamine for In Vivo Molecular Imaging of Vitamin B1 and Its Prodrug Using Positron Emission Tomography."
    J Org Chem, 80, 6250-6258 (2015).
  2. Doi H.:
    "Pd-mediated rapid cross-couplings using [11 C]methyl iodide: groundbreaking labeling methods in 11 C radiochemistry."
    J Labelled Comp Radiopharm., 58(3), 73-85 (2015).
  3. Goto M, Mizuma H, Wada Y, Suzuki M, Watanabe Y, Onoe H, and Doi H.:
    "11C-Labeled Capsaicin and Its in Vivo Molecular Imaging in Rats by Positron Emission Tomography"
    Food Nutr. Sci., 6(2), 216-220 (2015).
  4. Doi, H., Goto, M. and Suzuki, M.:
    "Pd0-Mediated Rapid C-[18F]Fluoromethylation by the Cross-Coupling Reaction of a [18F]Fluoromethyl Halide with an Arylboronic Acid Ester: Novel Method for the Synthesis of a 18F-Labeled Molecular Probe for Positron Emission Tomography"
    Bull. Chem. Soc. Jpn., 85, 1233-1238 (2012).
  5. Kuboyama T, Nakahara M, Yoshino M, Cui Y, Sako T, Wada Y, Imanishi T, Obika S, Watanabe Y, Suzuki M, Doi H.:
    "Stoichiometry-focused 18F-labeling of alkyne-substituted oligodeoxynucleotides using azido([18F]fluoromethyl)benzenes by Cu-catalyzed Huisgen reaction."
    Bioorg. Med. Chem., 19(1), 249-255 (2011).
  6. Suzuki M, Sumi K, Koyama H; Siqin, Hosoya T, Takashima-Hirano M, Doi H.:
    "Pd(0)-Mediated rapid coupling between methyl iodide and heteroarylstannanes: an efficient and general method for the incorporation of a positron-emitting (11)C radionuclide into heteroaromatic frameworks."
    Chemistry., 15(45), 12489-12495 (2009).
  7. Doi H, Ban I, Nonoyama A, Sumi K, Kuang C, Hosoya T, Tsukada H, Suzuki M.:
    "Palladium(0)-mediated rapid methylation and fluoromethylation on carbon frameworks by reacting methyl and fluoromethyl iodide with aryl and alkenyl boronic acid esters: useful for the synthesis of [11C]CH(3)--C- and [18F]FCH2--C-Containing PET tracers (PET=positron emission tomography)."
    Chemistry., 15(16), 4165-4171 (2009).
  8. Doi H, Barletta J, Suzuki M, Noyori R, Watanabe Y, Långström, B.:
    "Synthesis of 11C-labelled N,N’-diphenylurea and ethyl phenylcarbamate by a rhodium-promoted carbonylation via [11C]isocyanatobenzene using phenyl azide and [11C]carbon monoxide"
    Org Biomol Chem., 2(21), 3063-3066 (2004).
  9. Suzuki, M., and Doi, H., Kato, K., Bjorkman, M., Långström, B., Watanabe, Y. and Noyori, R. :
    "Rapid Methylation for the Synthesis of a 11C-Labeled Tolylisocarbacyclin Imaging the IP2 Receptor in a Living Human Brain"
    Tetrahedron, 56(42), 8263-8273 (2000).
  10. Suzuki, M., and Doi, H., Bjorkman, M., Andersson, Y., Långström, B., Watanabe, Y. and Noyori, R.:
    "Rapid Coupling of Methyl Iodide with Aryltributylstannanes Mediated by Palladium(0) Complexes: A General Protocol for the Synthesis of 11CH3-Labeled PET Tracers"
    Chem. Eur. J., 3(12), 2039-2042 (1997).

Lab Members

Principal Investigator

Hisashi Doi
Team Leader

Core Members

Tomoko Mori
Technical Scientist
Tatsuya Kida
Postdoctoral Researcher
Mieko Tsuji
Postdoctoral Researcher
Shuhei Takatani
Postdoctoral Researcher
Miki Goto
Research Associate
Aya Mawatari
Research Associate
Ami Igesaka
Technical Staff I

Contact information

6-7-3 Minatojima-minamimachi, Chuo-ku, Kobe, Hyogo 650-0047, Japan
Tel: +81-(0)78-304-7130
Fax: +81-(0)78-304-7131

Email: hisashi.doi [at] riken.jp

Related links