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1999 Fiscal Year Final Research Report Summary

Synthesis and Application of Carborane Containing MR Imaging Agent

Research Project

Project/Area Number 09554034
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section展開研究
Research Field Organic chemistry
Research InstitutionTOHOKU UNIVERSITY

Principal Investigator

YAMAMOTO Yoshinori  Department of Chemistry, Graduate School of Science, Tohoku University, Professor, 大学院・理学研究科, 教授 (60029519)

Co-Investigator(Kenkyū-buntansha) NAKAMURA Hiroyuki  Department of Chemistry, Graduate School of Science, Tohoku University, Research Associate, 大学院・理学研究科, 助手 (30274434)
Project Period (FY) 1997 – 1999
Keywordsneutron capture therapy / gadolinium / DTPA / boron carrier / carborane / MR imaging
Research Abstract

In order to improve and optimize efficient neutron capture therapy (NCT) treatment, it is necessary to follow the distribution of a carrier in the body in real time. However, it has been difficult to estimate the boron content of the tumor using technologies available. We succeeded to synthesize the carborane containing gadolinium-dimethylenetriamine pentaacetic acid (DTPA) unit which is commercially available under the trade name of Magnevist and is used as an MR imaging contrast medium. The evaluation of the Gd-carborane complex as an MR imaging and boron carrier agent was carried out in vivo using tumor-bearing Donryu rats by means of MRI, ICP-AES, and α-autoradiography. The MR imaging revealed that the carborane Gd-DTPA was metabolized slower in the body in comparison with Gd-DTPA. The results of ICP-AES method indicated that compound was incorporated into normal tissues and metabolized quickly, whereas it was not accumulated into tumor and brain tissue. The α-autoradiography showed that a high level of boron was obtained in the internal organs and in the necrosis of tumor tissue.

  • Research Products

    (24 results)

All Other

All Publications (24 results)

  • [Publications] H.Nemoto: "The Synthesis of Carborance Gadolinium-DTPA Complex for Boron Neutron Capture Therapy"J.Organomet.Chem.. 581. 170-175 (1999)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] A.T.Tatham: "Characterization of a Dual Labeled Probe for MRI and Neutron Capture Therapy"Mag.Res.Med.. 42. 32-36 (1999)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] K.-Y.Rho: "Synthesis of a New Amphiphilic ortho-Carborane Derivatives as a Potential BNCT Agent"Tetrahedron Lett.. 40. 4821-4824 (1999)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] H.Nakamura: "A Practical Method for the Synthesis of Enantiomerically Pure L-(4-Boronophenyl)alanine"Bull.Chem.Soc.Jpn.. 47. 231-235 (2000)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] H.Nakamura: "In vivo Evaluation of Carborane Gadolinium-DTPA Complex as an MR Imaging Boron Carrier"Chem.Pharm.Bull.. 48(印刷中). (2000)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] F. Girard, H. Nakamura, F. Fukuda, Y. Yamamoto, K. Yoshida: "Rat Tumor Imaging with B-10 Carborane Gadolinium Complex"Recent Advances in Biomedical Imaging, Ed. Y. Ishii, Elsevier. 201-207 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] J. Cai, H. Nemoto, H. Nakamura, B. Singaram, Y. Yamamoto: "Tetrabutylammonium Fluoride Promoted Regiospecific Reaction of (Trimethylsilyl-o-Carborane with Carbonyl Compounds."Advances in Boron Chemistry, Ed. W. Siebert, The Royal Society of Chemistry. 112-115 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Yamamoto: "New Reactions of Carboranes and Synthesis of a Carborane-Gadolinium Complex for BNCT."Advances in Boron Chemistry, Ed. W. Siebert, The Royal Society of Chemistry. 281-288 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] H. Nakamura, M. Sekido, Y. Yamamoto: "Synthesis of Carboranes Containing Azulene Framework and in vitro Evaluation as Boron Carriers."J. Med. Chem.. 40. 2825-2830 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] K. Imamura, Y. Yamamoto: "Synthesis and in Vitro Evaluation of 5-closo-and 5-nido-Orthocarboranyl-uridines as Boron Carriers"Bull. Chem. Soc. Jpn.. 70. 3103-3107 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Yamamoto: "Hiroshi Hatanaka Lecture : Search for New Tumor-seeking Boron Compounds in Japan"Advances in Neuton Capture Therapy Vol. II, Chemistry and Biology, Ed. B. Larsson, J. Crawford, R. Weinreich, Elservier. 22-29 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] H. Nakamura, M. Sekido, Y. Yamamoto: "Synthesis of Carboranes Containing Azulene Framework using a New Palladium Catalyzed Reaction"Advances in Neuton Capture Therapy Vol. II, Chemistry and Biology, Ed. B. Larsson, J. Crawford, R. Weinreich, Elservier. 42-45 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] K. Imamura, Y. Yamamoto: "Sugar-modified Carboranyluridines, their Synthesis and Biological Properties."Advances in Neuton Capture Therapy Vol. II, Chemistry and Biology, Ed. B. Larsson, J. Crawford, R. Weinreich, Elservier. 77-81 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M. Takagaki, K. Ono, Y. Oda, H. Kikuchi, H. Nemoto, S. Iwamoto, J. Cai and Y. Yamamoto: "Hydroxy-forms of p-Boromophenylalanine as Potential Boron Carriers in Boron Neutron Capture Therapy for Malignant Brain Tumors : A Case Study of its Pharmacokinetics on a GBM patient."Advances in Neuton Capture Therapy Vol. II, Chemistry and Biology, Ed. B. Larsson, J. Crawford, R. Weinreich, Elservier. 243-248 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y. Yamamoto, J. Cai, H. Nemoto, H. Nakamura, F. Girard, K. Yoshida, H. Fukuda: "A New Synthetic Method of All Carboxylate-Free DTPA Derivatives and its Application to the Synthesis of Gd-carborane Complex"Advances in Neuton Capture Therapy Vol. II, Chemistry and Biology, Ed. B. Larsson, J. Crawford, R. Weinreich, Elservier. 436-439 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] F. Girard, H. Fukuda, H. Nakamura, Y. Yamamoto: "MR Imaging of Rat Tumor with a ィイD110ィエD1B Carborane Gadolinium Complex."Advances in Neuton Capture Therapy Vol. II, Chemistry and Biology, Ed. B. Larsson, J. Crawford, R. Weinreich, Elservier. 271-275 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] "Tetrabutylammonium Fluoride Promoted Novel Reactions of o-Carborane : Inter- and Intramolecular Additions of Aldehydes and Ketones and Annulation via Enals and Enones."J. Am. Chem. Chem.. 120. 1167-1171 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] H. Nakamura, M. Fujiwara, Y. Yamamoto: "A Concise Synthesis of Enantiomerically Pure 4-Borno-L-phynylalanine from L-Tyrosine."J. Org. Chem.. 63, 21. 7529-7530 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] H. Nakamura, K. Aoyagi, Y. Yamamoto: "Synthetic Utility of o-Carborane : Novel Protecting Group for Aldehydes and Ketones."J. Organomet. Chem.. 574. 107-115 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] H. Nakamura, Y. Yamamoto: "Novel Addition and [3+2] Cycloaddition Reactions of Stannyl- and Silyl-ortho-carboranes to Carbonyl Compounds."Collect. Czech. Chem. Commun.. 64. 829-846 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] H. Nemoto, J. Cai, H. Nakamura, M. Fujiwara, Y. Yamamoto: "The Synthesis of a Carborane Gadolinium- DTPA Complex for Boron Neutron Capture Therapy."J. Organomet. Chem.. 581. 170-175 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] K.-Y. Rho, Y.-J. Cho, C.-M. Yoon, H. Nakamura: "Synthesis of a New Amphiphilic ortho-Carborane Derivative as a Potential BNCT Agent : 4-[N,N-Formyl-(ortho-carboranylmethyl)-amino]-venzoyl-L-glutamic acid"Tetrahedron Lett.. 40. 4821-4824 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] H. Nakamura, M. Fujiwara, Y. Yamamoto: "A Practical Method for the Synthesis of Enantiomerically Pure 4-Borron-L-phenylalanine"Bull. Chem. Soc. Jpn.. 73. 231-235 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] H. Nakamura, H. Fukuda, F. Girard, T. Kobayashi, H. Nemoto, J. Cai, K. Yoshida, Y. Yamamoto: "Synthesis and in Vivo Evaluation of Carborane Gadolinium-DTPA Complex as an MR Imaging Boron Carrier."Chem. Pharm. Bull.. (In pint).

    • Description
      「研究成果報告書概要(欧文)」より

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Published: 2001-10-23  

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