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Development of Boronated Cholesterols and their Highly Functionalized Nano Carriers for New Generation Neutron Capture Therapy

Research Project

Project/Area Number 26293007
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypePartial Multi-year Fund
Section一般
Research Field Physical pharmacy
Research InstitutionTokyo Institute of Technology

Principal Investigator

Nakamura Hiroyuki  東京工業大学, 科学技術創成研究院, 教授 (30274434)

Co-Investigator(Kenkyū-buntansha) 布施 新一郎  東京工業大学, 資源化学研究所, 准教授 (00505844)
佐藤 伸一  東京工業大学, 資源化学研究所, 助教 (20633134)
Project Period (FY) 2014-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥17,030,000 (Direct Cost: ¥13,100,000、Indirect Cost: ¥3,930,000)
Fiscal Year 2016: ¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2015: ¥5,460,000 (Direct Cost: ¥4,200,000、Indirect Cost: ¥1,260,000)
Fiscal Year 2014: ¥7,410,000 (Direct Cost: ¥5,700,000、Indirect Cost: ¥1,710,000)
Keywordsがん治療 / イメージング / 中性子捕捉療法 / リポソーム / 生体分子 / 放射線 / 蛍光 / がん / ナノバイオ / 薬学 / ホウ素
Outline of Final Research Achievements

Boronated cholesterols were successfully synthesized. Using these cholesterol, high content boron liposomes were developed for new generation neutron capture therapy. A counter cation of boron ion clusters (closo-dodecaborates) was found to be essential for the encapsulation efficacy of boronated liposomes: a sperimidinium form of closo-dodecaborates was highly encapsulated into liposomes prepared from phospholipids. Furthermore, boron imaging technologies in the cells have been developed using a combination of in cell click fluorescent imaging technique and Raman imaging technology.
Biopolymer-based boron delivery system was also developed for selective and efficient delivery of boron to tumor in vivo based on the EPR effect. Maleimide-closo-dodecaborate (MID) was successfully synthesized. MID conjugated not only a free SH group of cysteine residues but also lysine residues in proteins and its serum albumin conjugates were found to be accumulated into tumor selectively.

Report

(4 results)
  • 2016 Annual Research Report   Final Research Report ( PDF )
  • 2015 Annual Research Report
  • 2014 Annual Research Report
  • Research Products

    (53 results)

All 2017 2016 2015 2014 Other

All Int'l Joint Research (6 results) Journal Article (11 results) (of which Int'l Joint Research: 4 results,  Peer Reviewed: 11 results,  Acknowledgement Compliant: 7 results,  Open Access: 3 results) Presentation (27 results) (of which Int'l Joint Research: 8 results,  Invited: 17 results) Remarks (3 results) Patent(Industrial Property Rights) (2 results) (of which Overseas: 1 results) Funded Workshop (4 results)

  • [Int'l Joint Research] University of Szeged(Hungary)

    • Related Report
      2016 Annual Research Report
  • [Int'l Joint Research] University of Utah School of Medicine(米国)

    • Related Report
      2016 Annual Research Report
  • [Int'l Joint Research] University of Utah(米国)

    • Related Report
      2016 Annual Research Report
  • [Int'l Joint Research] Nazarbayev University(Kazakhstan)

    • Related Report
      2015 Annual Research Report
  • [Int'l Joint Research] KRIBB(韓国)

    • Related Report
      2015 Annual Research Report
  • [Int'l Joint Research] Tanta University(Egypt)

    • Related Report
      2015 Annual Research Report
  • [Journal Article] Novel hyaluronan formulation enhances the efficacy of boron neutron capture therapy for murine mesothelioma2016

    • Author(s)
      M. Sasai, H. Nakamura, N. Sougawa, Y. Sakurai, M. Suzuki, A. Matsuyama, C. M. Lee
    • Journal Title

      Anticancer Res.

      Volume: 36 Pages: 907-912

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Maleimide-functionalized closo-dodecaborate albumin conjugates (MID-AC): Unique ligation at cysteine and lysine residues enables efficient boron delivery to tumor for neutron capture therapy.2016

    • Author(s)
      S. Kikuchi, D. Kanoh, S. Sato, Y. Sakurai, M. Suzuki, H. Nakamura
    • Journal Title

      J. Control. Release

      Volume: 237 Pages: 160-167

    • DOI

      10.1016/j.jconrel.2016.07.017

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed
  • [Journal Article] The Life of Pi Star: Exploring the Exciting and Forbidden Worlds of the Benzophenone Photophore2016

    • Author(s)
      G. Dormen, H. Nakamura, A. Pulsipher, G. D. Prestwich
    • Journal Title

      Chem. Rev.

      Volume: 116 Issue: 24 Pages: 15284-15398

    • DOI

      10.1021/acs.chemrev.6b00342

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] A Rapid and Clean Synthetic Approach for Cyclic Peptides via Micro-flow Peptide Chain Elongation and Photochemical Cyclization: Synthesis of Cyclic RGD Peptide2016

    • Author(s)
      Yuto Mifune, Hiroyuki Nakamura, Shinichiro Fuse
    • Journal Title

      Organic and Biomolecular Chemistry

      Volume: 14 Issue: 47 Pages: 11244-11249

    • DOI

      10.1039/c6ob02391f

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Proteomic analysis of cellular response induced by boron neutron capture reaction in human squamous cell carcinoma SAS cells2015

    • Author(s)
      Sato A., Itoh T., Imamichi S., Kikuhara S., Fujimori H., Hirai T., Saito S., Sakurai Y., Tanaka H., Nakamura H., Suzuki M., Murakami Y., Baiseitov D., Berikkhanova K., Zhumadilov Z., Imahori Y., Itami J., Ono K., Masunaga S., Masutani M.
    • Journal Title

      Applied Radiation and Isotopes

      Volume: 106 Pages: 113-219

    • DOI

      10.1016/j.apradiso.2015.08.001

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Synthesis of Oligo-closo-dodecaborates by Hüisgen Click Reaction as Encapsulated Agents for Preparation of High-Boron-Content Liposomes for Neutron Capture Therapy2015

    • Author(s)
      H. Koganei, S. Tachikawa, M. E. El-Zaria, H. Nakamura
    • Journal Title

      New J. Chem.

      Volume: 39 Issue: 8 Pages: 6388-8211

    • DOI

      10.1039/c5nj00856e

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Boron-Based Drug Design2015

    • Author(s)
      H. S. Ban, H. Nakamura
    • Journal Title

      Chem. Rec.

      Volume: 15 Issue: 3 Pages: 616-635

    • DOI

      10.1002/tcr.201402100

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Antitumor Effect of Boron Nitride Nanotubes in Combination with Thermal Neutron Irradiation on BNCT2015

    • Author(s)
      H. Nakamura, H. Koganei, T. Miyoshi, Y. Sakurai, K. Ono, M. Suzuki
    • Journal Title

      Bioorg. Med. Chem. Lett.

      Volume: 25 Issue: 2 Pages: 172-174

    • DOI

      10.1016/j.bmcl.2014.12.005

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Spermidinium closo-dodecaborate-encapsulating liposomes as efficient boron delivery vehicles for neutron capture therapy2014

    • Author(s)
      S. Tachikawa, T. Miyoshi, H. Koganei, M. E. El-Zaria, C. Vinas, M. Suzuki, K. Ono, H. Nakamura
    • Journal Title

      Chem. Comm.

      Volume: 50 Issue: 82 Pages: 12325-12328

    • DOI

      10.1039/c4cc04344h

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Synthesis of protoporphyrin lipids and biological evaluation of micelles and liposomes2014

    • Author(s)
      S. Tachikawa, M. E. El-Zaria, R. Inomata, S. Sato, H. Nakamura
    • Journal Title

      Bioorganic & Medicinal Chemistry

      Volume: 22 Issue: 17 Pages: 4745-4751

    • DOI

      10.1016/j.bmc.2014.07.003

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Amphiphilic COSAN and I2-COSAN crossing synthetic lipid membranes: planar bilayers and liposomes2014

    • Author(s)
      C. Verdia-Baguena, A. Alcaraz, V. M. Aguilella, A. M. Cioran, S. Tachikawa, H. Nakamura, F. Teixidor, Clara Vinas
    • Journal Title

      Chem. Comm.

      Volume: 50 Issue: 51 Pages: 6700-6703

    • DOI

      10.1039/c4cc01283f

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Presentation] 中性子捕捉療法のためのナノキャリア型ホウ素デリバリーシステムの開発2017

    • Author(s)
      中村浩之
    • Organizer
      第19回癌治療増感研究シンポジウム
    • Place of Presentation
      奈良
    • Year and Date
      2017-02-03
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Presentation] Nanocarrier-Based Efficient Boron Delivery to Tumor for BNCT2017

    • Author(s)
      H. Nakamura
    • Organizer
      2st Taiwan Neutron Capture Therapy
    • Place of Presentation
      台北
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Enhanced Permeability and Retention (EPR) Effect-Based Efficient Boron Delivery Systems for BNCT2016

    • Author(s)
      H. Nakamura
    • Organizer
      17th International Congress on Neutron Capture Therapy
    • Place of Presentation
      Missouri
    • Year and Date
      2016-10-02
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Boron compounds suitable for BNCT2016

    • Author(s)
      H. Nakamura
    • Organizer
      1st NRW-Fukushima Joint Symposium on Advances in Medicine
    • Place of Presentation
      Essen
    • Year and Date
      2016-09-01
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Development of Boron Delivery Nano Vehicles for Neutron Capture Therapy of Cancers2016

    • Author(s)
      H. Nakamura
    • Organizer
      The Chinese University of Hong Kong, Seminar
    • Place of Presentation
      Hong Kong
    • Year and Date
      2016-05-03
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 外部エネルギーと局所増感型ナノデバイスによる低侵襲がん治療2016

    • Author(s)
      中村浩之
    • Organizer
      LSC研究発表会
    • Place of Presentation
      神戸学院大学
    • Year and Date
      2016-03-18
    • Related Report
      2015 Annual Research Report
    • Invited
  • [Presentation] ホウ素を使ってがんに挑む ~ホウ素創薬の最前線~2016

    • Author(s)
      中村浩之
    • Organizer
      第8回「国際的キャリア展望に向けた生命化学研究者による講演会」
    • Place of Presentation
      岡山大学
    • Year and Date
      2016-01-27
    • Related Report
      2015 Annual Research Report
    • Invited
  • [Presentation] リポソーム包埋型およびアルブミン結合型ホウ素キャリアー2016

    • Author(s)
      中村浩之
    • Organizer
      大阪医科大学附属病院がんセンター先端医療開発部門 シンポジウム
    • Place of Presentation
      高槻
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Presentation] 世界をリードする次世代低侵襲がん治療:中性子捕捉療法2016

    • Author(s)
      中村浩之
    • Organizer
      第2回神奈川県ヘルスケア・ニューフロンティア講座
    • Place of Presentation
      横浜
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Presentation] Development of boronated liposomes as efficient boron delivery vehicles for neutron capture therapy2015

    • Author(s)
      H. Nakamura
    • Organizer
      The International Chemical Congress of Pacific Basin Societies 2015 (Pacifichem 2015)
    • Place of Presentation
      Hawaii
    • Year and Date
      2015-12-15
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Use of serum albumin as an efficient boron delivery carrier for neutron capture therapy2015

    • Author(s)
      S. Kikuchi, D. Kanoh, S. Sato, H. Nakamura
    • Organizer
      The International Chemical Congress of Pacific Basin Societies 2015 (Pacifichem 2015)
    • Place of Presentation
      Hawaii
    • Year and Date
      2015-12-15
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Overview and Prospect of Boron Agents for Neutron Capture Therapy2015

    • Author(s)
      H. Nakamura
    • Organizer
      1st Academic meeting for Taiwan’s Society of Neutron Capture Therapy
    • Place of Presentation
      Taipei
    • Year and Date
      2015-12-05
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Highly Boronated Liposomes as Efficient Boron Delivery Vehicles for Neutron Capture Therapy2015

    • Author(s)
      H. Nakamura
    • Organizer
      ZING Conferences
    • Place of Presentation
      Spain
    • Year and Date
      2015-10-04
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 血清アルブミンを用いた新しいホウ素送達法の開発2015

    • Author(s)
      菊地 俊介、佐藤 伸一、中村 浩之
    • Organizer
      第12回日本中性子捕捉療法学会学術大会
    • Place of Presentation
      神戸学院大学
    • Year and Date
      2015-09-04
    • Related Report
      2015 Annual Research Report
  • [Presentation] 何故新しいホウ素薬剤は開発されないのか? ―これからのBoron Delivery Systemを考える―2015

    • Author(s)
      中村浩之
    • Organizer
      第12回日本中性子捕捉療法学会学術大会
    • Place of Presentation
      神戸学院大学
    • Year and Date
      2015-09-04
    • Related Report
      2015 Annual Research Report
    • Invited
  • [Presentation] ホウ素高集積化リポソームを指向した内封ホウ素薬剤開発2015

    • Author(s)
      中村浩之、立川将士、Clara Vinas、鈴木実、小野公二
    • Organizer
      第31回日本DDS学会学術集会
    • Place of Presentation
      東京
    • Year and Date
      2015-07-02
    • Related Report
      2015 Annual Research Report
  • [Presentation] Development of Liposomes for Efficient Boron Neutron Capture Therapy2015

    • Author(s)
      H. Nakamura
    • Organizer
      15th International Congress of Radiation Research (ICRR2015)
    • Place of Presentation
      京都
    • Year and Date
      2015-05-25
    • Related Report
      2015 Annual Research Report
    • Invited
  • [Presentation] 中性子捕捉療法のための血清アルブミンを用いた新しいホウ素送達法の開発2015

    • Author(s)
      菊地俊介、加納大輔、佐藤伸一、中村浩之
    • Organizer
      日本化学会第95回年会
    • Place of Presentation
      日本大学(千葉県・船橋市)
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] DDSによるがん治療の最前線2015

    • Author(s)
      中村浩之
    • Organizer
      川崎医科大学川崎医学会セミナー
    • Place of Presentation
      川崎医科大学(岡山県・倉敷市)
    • Year and Date
      2015-02-26
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] Therapeutic effect of porphyrus envelope-mediated photodynamic therapy: a novel therapeutic approach for the treatment of hormone antagonistic prostate cancer2015

    • Author(s)
      M. Inai, M. Yamauchi, N. Honda, H. Hazama, S. Tachikawa, H. Nakamura, Y. Kaneda, K. Awazu
    • Organizer
      SPIE Photonics West BiOS
    • Place of Presentation
      San Francisco (USA)
    • Year and Date
      2015-02-07 – 2015-02-12
    • Related Report
      2014 Annual Research Report
  • [Presentation] Albumin-bound closo-Dodecaborate as a Promising Boron Carrier to Tumor2014

    • Author(s)
      H. Nakamura
    • Organizer
      The 2nd International Workshop on BNCT
    • Place of Presentation
      京都大学(京都市)
    • Year and Date
      2014-12-09 – 2014-12-10
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] 外部エネルギーによる生体内局所増感型ナノデバイスの開発~QOL の高い低侵襲がん治療を目指して2014

    • Author(s)
      中村浩之
    • Organizer
      第14 回東北大学多元物質科学研究所研究発表会
    • Place of Presentation
      東北大学(宮城県・仙台市)
    • Year and Date
      2014-12-05
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] Development of liposomes for efficient boron neutron capture therapy2014

    • Author(s)
      H. Nakamura,
    • Organizer
      International Symposium on Integrated Molecular/Materials Science and Engineering (IMSE2014)
    • Place of Presentation
      南京(中国)
    • Year and Date
      2014-11-01 – 2014-11-03
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] 効率的ホウ素デリバリーシステムの構築を目指して2014

    • Author(s)
      中村浩之
    • Organizer
      平成26年度京都大学原子炉実験所専門研究会
    • Place of Presentation
      京都大学(大阪府・泉南郡)
    • Year and Date
      2014-09-29 – 2014-09-30
    • Related Report
      2014 Annual Research Report
  • [Presentation] 生体高分子をキャリアとしたホウ素デリバリーシステム:マレイミドドデカボレート(MID)の開発と生物活性評価2014

    • Author(s)
      加納大輔、立川将士、佐藤伸一、近藤夏子、鈴木実、桜井良憲、小野公二、中村浩之
    • Organizer
      第11回日本中性子捕捉療法学会学術大会
    • Place of Presentation
      大阪大学(大阪府・吹田市)
    • Year and Date
      2014-07-05 – 2014-07-06
    • Related Report
      2014 Annual Research Report
  • [Presentation] リポソーム内へのホウ素高集積化を可能とするデンドリマー型新規リポソーム薬剤の開発2014

    • Author(s)
      立川将士、小金井逸人、菊池俊介、加納大輔、鈴木実、小野公二、中村浩之
    • Organizer
      第11回日本中性子捕捉療法学会学術大会
    • Place of Presentation
      大阪大学(大阪府・吹田市)
    • Year and Date
      2014-07-05 – 2014-07-06
    • Related Report
      2014 Annual Research Report
  • [Presentation] Development of Albumin-bound closo-Dodecaborate and its Promising Boron Delivery Efficacy to Tumor2014

    • Author(s)
      Daisuke Kanoh, Shoji Tachikawa, Shinich Sato, Hiroyuki Nakamura
    • Organizer
      16th International Congress on Neutron Capture Therapy
    • Place of Presentation
      Helsinki (Finland)
    • Year and Date
      2014-06-14 – 2014-06-19
    • Related Report
      2014 Annual Research Report
  • [Remarks] 研究紹介

    • URL

      http://syn.res.titech.ac.jp/research/

    • Related Report
      2016 Annual Research Report
  • [Remarks] 中性子捕捉療法のための有望なホウ素薬剤を開発―マウスのがんで、高い治療効果を確認―

    • URL

      http://www.titech.ac.jp/news/2016/035881.html

    • Related Report
      2016 Annual Research Report
  • [Remarks] 東京工業大学 科学技術創成研究院 化学生命科学研究所 中村・布施研究室

    • URL

      http://syn.res.titech.ac.jp

    • Related Report
      2015 Annual Research Report
  • [Patent(Industrial Property Rights)] ホウ素含有化合物とタンパク質とのコンジュゲートを含む医薬組成物2016

    • Inventor(s)
      中村浩之
    • Industrial Property Rights Holder
      中村浩之
    • Industrial Property Rights Type
      特許
    • Filing Date
      2016-07-26
    • Related Report
      2016 Annual Research Report
    • Overseas
  • [Patent(Industrial Property Rights)] ホウ素含有化合物とタンパク質とのコンジュゲートを含む医薬組成物2015

    • Inventor(s)
      中村浩之
    • Industrial Property Rights Holder
      中村浩之
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2015-156726
    • Filing Date
      2015-08-07
    • Related Report
      2015 Annual Research Report
  • [Funded Workshop] The International Chemical Congress of Pacific Basin Societies 20152015

    • Place of Presentation
      Hawaii
    • Year and Date
      2015-12-15
    • Related Report
      2015 Annual Research Report
  • [Funded Workshop] 1st Academic meeting for Taiwan’s Society of Neutron Capture Therapy2015

    • Place of Presentation
      Taipei
    • Year and Date
      2015-12-05
    • Related Report
      2015 Annual Research Report
  • [Funded Workshop] ZING Conferences2015

    • Place of Presentation
      Spain
    • Year and Date
      2015-10-04
    • Related Report
      2015 Annual Research Report
  • [Funded Workshop] 15th International Congress of Radiation Research (ICRR2015)2015

    • Place of Presentation
      Kyoto
    • Year and Date
      2015-05-25
    • Related Report
      2015 Annual Research Report

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Published: 2014-04-04   Modified: 2022-02-16  

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