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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
Project Status Completed (Fiscal Year 1999)
Budget Amount *help
¥11,800,000 (Direct Cost: ¥11,800,000)
Fiscal Year 1999: ¥3,000,000 (Direct Cost: ¥3,000,000)
Fiscal Year 1998: ¥2,700,000 (Direct Cost: ¥2,700,000)
Fiscal Year 1997: ¥6,100,000 (Direct Cost: ¥6,100,000)
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.

Report

(4 results)
  • 1999 Annual Research Report   Final Research Report Summary
  • 1998 Annual Research Report
  • 1997 Annual Research Report
  • Research Products

    (36 results)

All Other

All Publications (36 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
    • Related Report
      1999 Final Research Report Summary
  • [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
    • Related Report
      1999 Final Research Report Summary
  • [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
    • Related Report
      1999 Final Research Report Summary
  • [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
    • Related Report
      1999 Final Research Report Summary
  • [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
    • Related Report
      1999 Final Research Report Summary
  • [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
    • Related Report
      1999 Final Research Report Summary
  • [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
    • Related Report
      1999 Final Research Report Summary
  • [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
    • Related Report
      1999 Final Research Report Summary
  • [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
    • Related Report
      1999 Final Research Report Summary
  • [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
    • Related Report
      1999 Final Research Report Summary
  • [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
    • Related Report
      1999 Final Research Report Summary
  • [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
    • Related Report
      1999 Final Research Report Summary
  • [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
    • Related Report
      1999 Final Research Report Summary
  • [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
    • Related Report
      1999 Final Research Report Summary
  • [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
    • Related Report
      1999 Final Research Report Summary
  • [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
    • Related Report
      1999 Final Research Report Summary
  • [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
    • Related Report
      1999 Final Research Report Summary
  • [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
    • Related Report
      1999 Final Research Report Summary
  • [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
    • Related Report
      1999 Final Research Report Summary
  • [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
    • Related Report
      1999 Final Research Report Summary
  • [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
    • Related Report
      1999 Final Research Report Summary
  • [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
    • Related Report
      1999 Final Research Report Summary
  • [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
    • Related Report
      1999 Final Research Report Summary
  • [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
    • Related Report
      1999 Final Research Report Summary
  • [Publications] H.Nemoto: "The Synthesis of Carborane Gadolinium-DTPA Complex for Boron Neutron Capture Therapy"J.Organomet.Chem.. 581. 170-175 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] A.T.Tatham: "Characterization of a Dual Labeled Probe for MRI and Neutron Capture Therapy"Mag.Res.Med.. 42. 32-36 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] K.-Y.Rho: "Synthesis of a New Amphiphilic ortho-Carborane Derivatives as a Potential BNCT Agent"Tetrahedron Lett.. 40. 4821-4824 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] H.Nakamura: "A Practical Method for the Synthesis of Enanitiomerically Pure L-(4-Boronophenyl)alanine"Bull.Chem.Soc.Jpn.. 47. 231-235 (2000)

    • Related Report
      1999 Annual Research Report
  • [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)

    • Related Report
      1999 Annual Research Report
  • [Publications] H.Nemoto: "The Synthesis of Carborane Gadolinium-DTPA Complex for Boron Neutron Capture Therapy" J.Organomet.Chem.印刷中. (1999)

    • Related Report
      1998 Annual Research Report
  • [Publications] A.T.Tatham: "Characterization of a Dual Labeled Probe for MRI and Neutron Capture Therapy" Mag.Res.Med.印刷中. (1999)

    • Related Report
      1998 Annual Research Report
  • [Publications] H.Nakamura: "A Concise Synthesis of Enantiomerically Pure L-(4-Boronophenyl)alanine from L-Tyrosine" J.Org.Chem.63. 7529-7530 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Y.Yamamoto: "A New Synthetic Method of All Carboxylate-free DTPA Derivatives and Its Application to the Synthesis of Gd-Carborane Complex." Advances in Neutron Capture Therapy,Eds.B.Larsson,et.al.436-439 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] F.Girard: "Rat Tumor Imaging with B-10 Carborane Gadolinium Complex." Recent Advances in Biomedical Imaging,Ed.Y.Ishii et al.201-207 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] F.Girard: "MR Imaging of Rat Tumor with 10B Carborane Gadolinium Complex." Advances in Neutron Capture Therapy,Eds.B.Larsson,et.al.271-275 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] H.Nakamura: "TBAF Promoted Novel Reactions of ortho-Carboranes : Inter-and Intramolecular Addition to Aldehydes and Ketones,and Annulation via Enones and Enats." J.Am.Chem.Soc.120. 1167-1171 (1998)

    • Related Report
      1997 Annual Research Report

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Published: 1997-04-01   Modified: 2016-04-21  

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