Title:
SYNTHESIS METHOD OF POSITRON-EMITTING NUCLIDE-LABELED PROTEIN
Document Type and Number:
WIPO Patent Application WO/2019/098291
Kind Code:
A1
Abstract:
This method uses a positron-emitting nuclide-labeled amino acid or a derivative thereof to synthesize a positron-emitting nuclide-labeled protein by means of a cell-free protein synthesis system. Said cell-free protein synthesis system is a system reconfigured by means of a factor involved in protein synthesis, and said method uses a positron-emitting nuclide-labeled unnatural amino acid as the positron-emitting nuclide-labeled amino acid or derivative thereof; the method further uses a template nucleic acid into which a stop codon has been introduced, tRNA which recognizes the introduced stop codon and binds to the positron-emitting nuclide-labeled unnatural amino acid, and an aminoacyl-tRNA synthetic enzyme which causes bonding between the tRNA and the positron-emitting nuclide-labeled unnatural amino acid.
Inventors:
HARADA RYUICHI (JP)
YANAI KAZUHIKO (JP)
IWATA REN (JP)
FURUMOTO SHOZO (JP)
YANAI AI (JP)
YANAI KAZUHIKO (JP)
IWATA REN (JP)
FURUMOTO SHOZO (JP)
YANAI AI (JP)
Application Number:
PCT/JP2018/042338
Publication Date:
May 23, 2019
Filing Date:
November 15, 2018
Export Citation:
Assignee:
UNIV TOHOKU (JP)
International Classes:
C12P21/02; A61K51/08; C07B59/00; C07K14/00
Foreign References:
| US20070218483A1 | 2007-09-20 | |||
| JP2010263809A | 2010-11-25 |
Other References:
YANAI, A. ET AL.: "Site-Specific Labeling of F-18 Proteins Using a Supplemented Cell -Free Protein Synthesis System and 0-2-[18F] Fluoroethyl-L- Tyrosine: [18F] FET-HER2 Affibody Molecule", MOLECULAR IMAGING AND BIOLOGY, vol. 21, no. 3, 15 August 2018 (2018-08-15), pages 529 - 537, XP036785858
HARADA, R. ET AL.: "Synthesis and Characterization of 18F-Interleukin-8 Using a Cell -Free Translation System and 4-18F-Fluoro-L-Proline", THE JOURNAL OF NUCLEAR MEDICINE, vol. 57, no. 4, 2016, pages 634 - 639
CAI, W. ET AL.: "PET Imaging of Colorectal Cancer in Xenograft-Bearing Mice by Use of an 18F-Labeled T84.66 Anti-Carcinoembryonic Antigen Diabody", THE JOURNAL OF NUCLEAR MEDICINE, vol. 48, no. 2, 2007, pages 304 - 310, XP055003542, DOI: doi:10.2967/jnumed.107.043216
SUZUKI, M. ET AL.: "An experimental study on 0- [18F]fluoromethyl-L-tyrosine for differentiation between tumor and inflammatory tissues", ANNALS OF NUCLEAR MEDICINE, vol. 19, no. 7, October 2005 (2005-10-01), pages 589 - 595, XP055609797
IWATA, R. ET AL.: "Radiosynthesis of O-[11C]methyl- L-tyrosine and 0-[18F]Fluoromethyl-L-tyrosine as potential PET tracers for imaging amino acid transport", JOURNAL OF LABELLED COMPOUNDS AND RADIOPHARMACEUTICALS, vol. 46, 2003, pages 555 - 566, XP002313435, DOI: doi:10.1002/jlcr.696
WESTER, H. J. ET AL.: "Synthesis and Radiopharmacology of 0-(2-[18F]fluoroethyl)-L- Tyrosine for Tumor Imaging", THE JOURNAL OF NUCLEAR MEDICINE, vol. 40, no. 1, 1999, pages 205 - 212, XP002290178
TANG, G. ET AL.: "Pharmacokinetics and radiation dosimetry estimation of O-(2-[18F] fluoroethyl)-1- tyrosine as oncologic PET tracer", APPLIED RADIATION AND ISOTOPES, vol. 58, 2003, pages 219 - 225, XP004405083, DOI: doi:10.1016/S0969-8043(02)00311-1
WATANABE, Y. ET AL.: "Relationship between the uptake of 18F borono-L-phenylalanine and L-[methyl- 11C] methionine in head and neck tumors and normal organs", RADIATION ONCOLOGY, vol. 12, no. 17, 14 January 2017 (2017-01-14), XP055609802
HAVU-AUREN, K. ET AL.: "Uptake of 4-borono-2- [18F]fluoro-L-phenylalanine in sporadic and neurofibromatosis 2-related schwannoma and meningioma studied with PET", EUROPEAN JOURNAL OF NUCLEAR MEDICINE AND MOLECULAR IMAGING, vol. 34, no. 1, 2007, pages 87 - 94, XP019458859, DOI: doi:10.1007/s00259-006-0154-y
YANAI, KAZUHIKO ET AL.: "Development and research of PET imaging probe'', Tohoku University Global COE program ''Nano-biomedical engineering hub established on growth focus of new century world", 2009 ANNUAL REPORT OF NANO-BIOMEDICAL ENGINEERING, vol. 3, no. 1, 2009, pages 123 - 128
LIUC, C. ET AL.: "Adding New Chemistries to the Genetic Code", ANNUAL REVIEW OF BIOCHEMISTRY, vol. 79, 2010, pages 413 - 444, XP055026250, DOI: doi:10.1146/annurev.biochem.052308.105824
WANG, L. ET AL.: "Expanding the Genetic Code of Escherichia coli", SCIENCE, vol. 292, 2001, pages 498 - 500, XP002904367, DOI: doi:10.1126/science.1060077
BRUSTAD, E. ET AL.: "A Genetically Encoded Boronate-Containing Amino Acid", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, vol. 47, no. 43, 9 October 2008 (2008-10-09), pages 8220 - 8223, XP055609807
IWATA, R. ET AL.: "Practical microscale one-pot radiosynthesis of 18F-labeled probes", JOURNAL LABELLED COMPOUNDS AND RADIOPHARMACEUTICALS, vol. 61, no. 7, 8 March 2018 (2018-03-08) - 17 April 2018 (2018-04-17), pages 540 - 549, XP055609810
IWATA, R. ET AL.: "Minimization of the amount of Kryptofix 222-KHC03 for applications to microscale 18F-radiolabeling", APPLIED RADIATION AND ISOTOPES, vol. 125, 13 April 2017 (2017-04-13), pages 113 - 118, XP085044168, DOI: doi:10.1016/j.apradiso.2017.04.021
ALEXOFF, D. L. ET AL.: "Removal of the 2. 2. 2 Crypt and (Kryptofix 2.2.2TM) from 18FDG by Cation Exchange", APPLIED RADIATION AND ISOTOPES, vol. 42, no. 12, 1991, pages 1189 - 1193, XP024726026
HARADA, R. ET AL.: "Synthesis and Characterization of 18F-Interleukin-8 Using a Cell -Free Translation System and 4-18F-Fluoro-L-Proline", THE JOURNAL OF NUCLEAR MEDICINE, vol. 57, no. 4, 2016, pages 634 - 639
CAI, W. ET AL.: "PET Imaging of Colorectal Cancer in Xenograft-Bearing Mice by Use of an 18F-Labeled T84.66 Anti-Carcinoembryonic Antigen Diabody", THE JOURNAL OF NUCLEAR MEDICINE, vol. 48, no. 2, 2007, pages 304 - 310, XP055003542, DOI: doi:10.2967/jnumed.107.043216
SUZUKI, M. ET AL.: "An experimental study on 0- [18F]fluoromethyl-L-tyrosine for differentiation between tumor and inflammatory tissues", ANNALS OF NUCLEAR MEDICINE, vol. 19, no. 7, October 2005 (2005-10-01), pages 589 - 595, XP055609797
IWATA, R. ET AL.: "Radiosynthesis of O-[11C]methyl- L-tyrosine and 0-[18F]Fluoromethyl-L-tyrosine as potential PET tracers for imaging amino acid transport", JOURNAL OF LABELLED COMPOUNDS AND RADIOPHARMACEUTICALS, vol. 46, 2003, pages 555 - 566, XP002313435, DOI: doi:10.1002/jlcr.696
WESTER, H. J. ET AL.: "Synthesis and Radiopharmacology of 0-(2-[18F]fluoroethyl)-L- Tyrosine for Tumor Imaging", THE JOURNAL OF NUCLEAR MEDICINE, vol. 40, no. 1, 1999, pages 205 - 212, XP002290178
TANG, G. ET AL.: "Pharmacokinetics and radiation dosimetry estimation of O-(2-[18F] fluoroethyl)-1- tyrosine as oncologic PET tracer", APPLIED RADIATION AND ISOTOPES, vol. 58, 2003, pages 219 - 225, XP004405083, DOI: doi:10.1016/S0969-8043(02)00311-1
WATANABE, Y. ET AL.: "Relationship between the uptake of 18F borono-L-phenylalanine and L-[methyl- 11C] methionine in head and neck tumors and normal organs", RADIATION ONCOLOGY, vol. 12, no. 17, 14 January 2017 (2017-01-14), XP055609802
HAVU-AUREN, K. ET AL.: "Uptake of 4-borono-2- [18F]fluoro-L-phenylalanine in sporadic and neurofibromatosis 2-related schwannoma and meningioma studied with PET", EUROPEAN JOURNAL OF NUCLEAR MEDICINE AND MOLECULAR IMAGING, vol. 34, no. 1, 2007, pages 87 - 94, XP019458859, DOI: doi:10.1007/s00259-006-0154-y
YANAI, KAZUHIKO ET AL.: "Development and research of PET imaging probe'', Tohoku University Global COE program ''Nano-biomedical engineering hub established on growth focus of new century world", 2009 ANNUAL REPORT OF NANO-BIOMEDICAL ENGINEERING, vol. 3, no. 1, 2009, pages 123 - 128
LIUC, C. ET AL.: "Adding New Chemistries to the Genetic Code", ANNUAL REVIEW OF BIOCHEMISTRY, vol. 79, 2010, pages 413 - 444, XP055026250, DOI: doi:10.1146/annurev.biochem.052308.105824
WANG, L. ET AL.: "Expanding the Genetic Code of Escherichia coli", SCIENCE, vol. 292, 2001, pages 498 - 500, XP002904367, DOI: doi:10.1126/science.1060077
BRUSTAD, E. ET AL.: "A Genetically Encoded Boronate-Containing Amino Acid", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, vol. 47, no. 43, 9 October 2008 (2008-10-09), pages 8220 - 8223, XP055609807
IWATA, R. ET AL.: "Practical microscale one-pot radiosynthesis of 18F-labeled probes", JOURNAL LABELLED COMPOUNDS AND RADIOPHARMACEUTICALS, vol. 61, no. 7, 8 March 2018 (2018-03-08) - 17 April 2018 (2018-04-17), pages 540 - 549, XP055609810
IWATA, R. ET AL.: "Minimization of the amount of Kryptofix 222-KHC03 for applications to microscale 18F-radiolabeling", APPLIED RADIATION AND ISOTOPES, vol. 125, 13 April 2017 (2017-04-13), pages 113 - 118, XP085044168, DOI: doi:10.1016/j.apradiso.2017.04.021
ALEXOFF, D. L. ET AL.: "Removal of the 2. 2. 2 Crypt and (Kryptofix 2.2.2TM) from 18FDG by Cation Exchange", APPLIED RADIATION AND ISOTOPES, vol. 42, no. 12, 1991, pages 1189 - 1193, XP024726026
Attorney, Agent or Firm:
SAEGUSA & PARTNERS (JP)
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