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Constructions of supramolecular metal-free MRI contrast agents showing a higher sensitivity

Research Project

Project/Area Number 26620070
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Functional solid state chemistry
Research InstitutionKyushu University

Principal Investigator

Karasawa Satoru  九州大学, 薬学研究院, 准教授 (80315100)

Research Collaborator HAGIHARA Ryusuke  九州大学, 大学院薬学府
OKAMOTO Yuna  九州大学, 大学院薬学研究院, 技術補佐員
ARAKI Takeru  九州大学, 大学院薬学府
MORISHITA Kosuke  九州大学, 大学院薬学府
SHIRAISHI Ryoma  九州大学, 薬学部
Project Period (FY) 2014-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥3,770,000 (Direct Cost: ¥2,900,000、Indirect Cost: ¥870,000)
Fiscal Year 2016: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2015: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2014: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
KeywordsMRI / 造影剤 / ラジカル / ナノ微粒子 / がん / 自己集合化 / がん診断 / メタルフリー / TEMPO / 超分子 / 蛍光イメージング
Outline of Final Research Achievements

MRI contrast agents used in clinical are containing metals such as Gadolinium. Due to influences of the metal ion, the contras agents often show significant side effects. In order to This time, we developed the metal free contrast agents using organic radicals. However, the contrast agents containing organic radicals exhibit smaller sensitivity than that of metal contrast agents because of smaller spin quantum number. Accordingly, to overcome the disadvantage of the metal free contrast agents and enhance the sensitivity, we used nanoparticles possessing organic radical (RNP). As the results, the RNP showed higher sensitivity than that of radicals consisted of smaller molecules. Furthermore, we successfully prepared the RNP possessing a pH responsiveness. Tumor tissues show the acidic microenvironment than that of normal tissues. Thus, in the future, we will prepare the metal free contrast agent capable of being in response to the tumor that have acidic microenvironment.

Report

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

    (47 results)

All 2017 2016 2015 2014

All Journal Article (13 results) (of which Int'l Joint Research: 2 results,  Peer Reviewed: 13 results,  Acknowledgement Compliant: 5 results) Presentation (33 results) (of which Int'l Joint Research: 4 results,  Invited: 1 results) Patent(Industrial Property Rights) (1 results)

  • [Journal Article] Self-Assembly Behavior of Emissive Urea Benzene Derivatives Enables Heat-Induced Accumulation in Tumor Tissue2017

    • Author(s)
      Takeru Araki, Shuhei Murayama, Kazuteru Usui, Takashi Shimada, Ichio Aoki, and Satoru Karasawa
    • Journal Title

      Nano Lett.

      Volume: 17 Issue: 4 Pages: 2397-2403

    • DOI

      10.1021/acs.nanolett.6b05371

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Thermal- and pH-Dependent Size Variable Radical Nanoparticles and Its Water Proton Relaxivity for Metal-Free MRI Functional Contrast Agents2016

    • Author(s)
      Kosuke Morishita, Shuhei Murayama, Takeru Araki, Ichi Aoki, Satoru Karasawa
    • Journal Title

      J. Org. Chem

      Volume: 81 Pages: 8211-8362

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Regioselective Photocyclizations of Di(quinolinyl)arylamines and Tri(quinolinyl)amine with Emission Color Changes and Photoreaction-induced Self-assemblies2016

    • Author(s)
      Satoru Karasawa, Jun-ichi Todo, Kazuteru Usui, Naomi Harada, Kenji Yoza, Hiroshi Suemune and Noboru Koga
    • Journal Title

      Chem E-J.

      Volume: in press Issue: 23 Pages: 7771-7781

    • DOI

      10.1002/chem.201600514

    • Related Report
      2015 Research-status Report
    • Peer Reviewed
  • [Journal Article] 3- and 4-(α-diazobenzyl)pyridine-N-oxides as photoresponsive magnetic couplers for 2p–4f heterospin systems: formation of carbene–TbIII and carbene–DyIII single-molecule magnets2016

    • Author(s)
      Kensuke. Murashima, Satoru Karasawa, Kenji Yoza, Yuji Inagaki and Noboru Koga
    • Journal Title

      Dalton Trans

      Volume: 45 Issue: 16 Pages: 7067-7077

    • DOI

      10.1039/c6dt00420b

    • Related Report
      2015 Research-status Report
    • Peer Reviewed
  • [Journal Article] Rational syntheses of helical pai-conjugated oligopyrrins with a bipyrrole linkage: geometry control of bis-copper(II) coordination2016

    • Author(s)
      Kai Zhang, Mathew Savage, Xin Li, Yu Jiang, Masatoshi Ishida, Koki Mitsuno, Satoru Karasawa, Tatsuhisa Kato, Weihua Zhu, Sihai Yang, Hiroyuki Furuta and Yongshu Xie
    • Journal Title

      Chem. Commun.

      Volume: 52 Issue: 29 Pages: 5148-5151

    • DOI

      10.1039/c6cc00707d

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] One-, Two-, and Three-Dimensional Heterospin Complexes Consisting of 3d Metal Ions, 4-(N-tert-Butyloxylamino)pyridine (4NOpy), and Dicyanamide ion (DCA); Crystal Structures and Magnetic Properties of [MII(4NOpy)x(DCA)y(CH3CN)z]n: MII = Mn, Co, Ni, Cu, and Zn2016

    • Author(s)
      Hiraku Ogawa, Koya Mori, Kensuke Murashima, Satoru Karasawa, and Noboru Koga
    • Journal Title

      Inorg. Chem.

      Volume: 55 Issue: 2 Pages: 717-728

    • DOI

      10.1021/acs.inorgchem.5b02159

    • Related Report
      2015 Research-status Report
    • Peer Reviewed
  • [Journal Article] Determination of the absolute configuration of the novel anti-trypanosomal iridoid molucidin isolated from Morinda lucida by X-ray analysis,2015

    • Author(s)
      Satoru Karasawa, Kenji Yoza, Nguyen Huu Tung, Takuhiro Uto, Shoji Yamaoka, Nobuo Ohta, Yukihiro Shoyama, 外27名、
    • Journal Title

      Tetrahedron Lett.

      Volume: 56 Issue: 52 Pages: 7158-7160

    • DOI

      10.1016/j.tetlet.2015.11.031

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Diazopyridine-Ni(II) Complexes Exhibiting Intra-Chain Ferromagnetic Interaction After Irradiation: Formation of Magnetic Gel2015

    • Author(s)
      Koya Mori, Rumi Eguchi, Satoru Karasawa, Noboru Koga,
    • Journal Title

      Inorg. Chem. Front

      Volume: 2 Issue: 10 Pages: 917-926

    • DOI

      10.1039/c5qi00109a

    • Related Report
      2015 Research-status Report
    • Peer Reviewed
  • [Journal Article] , Crystalline transformations of dinaphthyridinylamine derivatives with alteration of solid-state emission in response to external stimuli,2015

    • Author(s)
      Ryusuke Hagihara, Naomi Harada, Satoru Karasawa, Noboru Koga
    • Journal Title

      CrystEngComm,

      Volume: 15 Issue: 46 Pages: 8825-8834

    • DOI

      10.1039/c5ce01126d

    • Related Report
      2015 Research-status Report
    • Peer Reviewed
  • [Journal Article] Stable π-Radical from a Contracted Doubly N-Confused Hexaphyrin by Bis-Palladium Metallation2015

    • Author(s)
      Y. Hisamune, K. Nishimura, K. Isakari, M. Ishida, S. Mori, Satoru. Karasawa, T. Kato, Sangsu L., D.Kim, and H. Furuta,
    • Journal Title

      Angew. Chem., Int. Ed. Engl.

      Volume: 54 Issue: 25 Pages: 7323-7327

    • DOI

      10.1002/anie.201502285

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Journal Article] Heterospin Single-Molecule Magnet Behaviors after Irradiation of Polymorphous 2:2 Cyclic Diazo-Cobalt(II) Complexes2015

    • Author(s)
      Daisuke Yoshihara, Satoru Karasawa, Noboru Koga
    • Journal Title

      Inorg. Chim. Acta

      Volume: 428 Pages: 57-64

    • DOI

      10.1016/j.ica.2015.01.025

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Magnetic Properties of 1:2 Mixed Cobalt(II) Salicylaldehyde Schiff-Base Complexes with Pyridine Ligands Carrying High-Spin Carbenes (Scar = 2/2, 4/2, 6/2, and 8/2) in Dilute Frozen Solutions: Role of Organic Spin in Heterospin Single-Molecule Magnets2014

    • Author(s)
      Satoru Karasawa, Kimihiro Nakano, Daisuke Yoshihara, Noriko Yamamoto, Jun-ichi Tanokashira, Takahito Yoshizaki, Yuji Inagaki, Noboru Koga
    • Journal Title

      Inorg Chem.

      Volume: 53 Issue: 11 Pages: 5447-5457

    • DOI

      10.1021/ic403074d

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Crystal Structures, Thermal Properties, and Emission Behaviors of N, N-R-Phenyl-7-amino-2,4-trifluoromethylquinoline Derivatives: Supercooled Liquid-to Crystal Transformation Induced by Mechanical2014

    • Author(s)
      Satoru Karasawa, Ryusuke Hagihara, Yuichiro Abe, Naomi Harada, Jun-ichi Todo, Noboru Koga
    • Journal Title

      Cryst. Growth Des.

      Volume: 14 Issue: 5 Pages: 2468-2478

    • DOI

      10.1021/cg5001842

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] ドナー・アクセプター型アザナフタレニルアミン誘導体における蛍光変化を伴った新規光反応2017

    • Author(s)
      萩原隆介・唐澤 悟
    • Organizer
      第97日本化学会春季年会
    • Place of Presentation
      横浜市
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] Water Proton Relaxivities and Structures in Water Solution of Self-Assemble Organic Radicals Aiming Metal Free MRI Contrast Agents2016

    • Author(s)
      Satoru Karasawa
    • Organizer
      2016 ICMM
    • Place of Presentation
      Sendai
    • Year and Date
      2016-09-04
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Development of MRI Contrast Agents Having Thermal Responsive Functions for Accumulation to the Tumor Tissues2016

    • Author(s)
      Takeru Araki, Noboru Koga, Satoru Karasawa,
    • Organizer
      2016 ICMM
    • Place of Presentation
      Sendai
    • Year and Date
      2016-09-04
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Structures and Magnetic Properties of Carbene-Fe(II) Complexes Having the Intra- Molecular Ferromagnetic Interaction2016

    • Author(s)
      Koya Mori, Noboru Koga, Satoru Karasawa
    • Organizer
      2016 ICMM
    • Place of Presentation
      Sendai
    • Year and Date
      2016-09-04
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Photoreaction of Push-Pull Type Quinoline Derivatives Accompanied with Emission Change2016

    • Author(s)
      Satoru Karasawa, Kazuteru Usui, Noboru Koga
    • Organizer
      The 70th Fujihara Seminar
    • Place of Presentation
      Fukuoka
    • Year and Date
      2016-04-17
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] アザナフタレニルアミン誘導体 の光反応2016

    • Author(s)
      萩原 隆介・唐澤 悟・古賀 登
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      京田辺市 同志社大学京田辺キャンパス
    • Year and Date
      2016-03-24
    • Related Report
      2015 Research-status Report
  • [Presentation] 温度応答性バイオイメージング分子の合成と物性評価2016

    • Author(s)
      荒木 健、村山 修平、唐澤 悟、青木 伊知男、佐賀 恒夫、古賀 登
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      京田辺市、同志社大学京田辺キャンパス
    • Year and Date
      2016-03-24
    • Related Report
      2015 Research-status Report
  • [Presentation] 外部刺激応答性を有する新規ウレニルベンゼン誘導体の合成と自己集合化挙動2016

    • Author(s)
      森下 晃佑・荒木 健・唐澤 悟・古賀 登
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      京田辺市、同志社大学京田辺キャンパス
    • Year and Date
      2016-03-24
    • Related Report
      2015 Research-status Report
  • [Presentation] ヘテロスピン鉄錯体の構造と光照射前後の磁性2016

    • Author(s)
      森 昂也、唐澤 悟、古賀 登
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      京田辺市、同志社大学京田辺キャンパス
    • Year and Date
      2016-03-24
    • Related Report
      2015 Research-status Report
  • [Presentation] Photochemical Reactions and Photophysical Properties of Dinaphthyridinylamine Derivatives2015

    • Author(s)
      Ryusuke Hagiahra・Satoru Karasawa・Noboru Koga
    • Organizer
      2015 PacifiChem
    • Place of Presentation
      Honolulu, Hawaii
    • Year and Date
      2015-12-15
    • Related Report
      2015 Research-status Report
  • [Presentation] Crystal structures and magnetic properties of photoresponsive 2p-4f heterospin complexes2015

    • Author(s)
      Kensuke Murashima, Satoru Karasawa, Noboru Koga
    • Organizer
      2015 PacifiChem
    • Place of Presentation
      Honolulu, Hawaii
    • Year and Date
      2015-12-15
    • Related Report
      2015 Research-status Report
  • [Presentation] Magnetic properties of heterospin single-molecule magnets (SMMs) in frozen solution: Roles of Stotal value in SMMs2015

    • Author(s)
      Satoru Karasawa, Noboru Koga
    • Organizer
      2015 PacifiChem
    • Place of Presentation
      Honolulu, Hawaii
    • Year and Date
      2015-12-15
    • Related Report
      2015 Research-status Report
  • [Presentation] Preparation of Urenylary Derivatives Carrying One and Two Amphiphilic Chains and Their Self-Assembly Behaviors in Water2015

    • Author(s)
      Yuna Okamoto, Eriko Ohashi, Satoru Karasawa, Noboru Koga
    • Organizer
      2015 PacifiChem
    • Place of Presentation
      Honolulu, Hawaii
    • Year and Date
      2015-12-15
    • Related Report
      2015 Research-status Report
  • [Presentation] Preparations, molecular structures, and magnetic properties of photoresponsive cyclic dinuclear MnII, FeII, and NiII complexes in heterospin systems.2015

    • Author(s)
      Koya Mori, Daisuke Yoshihara, Satoru. Karasawa, Noboru Koga
    • Organizer
      2015 PacifiChem
    • Place of Presentation
      Honolulu, Hawaii
    • Year and Date
      2015-12-15
    • Related Report
      2015 Research-status Report
  • [Presentation] Di(1.8-naphthyridine-2-yl)amine誘 導体の合成と溶液中での蛍光を伴った光反応2015

    • Author(s)
      萩原 隆介・唐澤 悟・古賀 登
    • Organizer
      第26回基礎有機化学討論会
    • Place of Presentation
      松山市 愛媛大学城北キャンパス・松山大学文京キャンパス
    • Year and Date
      2015-09-24
    • Related Report
      2015 Research-status Report
  • [Presentation] 生体イメージングを目指した温度応答性蛍光プローブの合成と水中での物性評価2015

    • Author(s)
      荒木 健、嶋田 敬志、村山 修平、唐澤 悟、青木 伊知男、佐賀 恒夫、古賀 登
    • Organizer
      第26回基礎有機化学討論会
    • Place of Presentation
      松山市 愛媛大学城北キャンパス・松山大学文京キャンパス
    • Year and Date
      2015-09-24
    • Related Report
      2015 Research-status Report
  • [Presentation] ヘキサアザペンタセン誘導体の合成と光物性2015

    • Author(s)
      廣田 淳子・唐澤 悟・古賀 登
    • Organizer
      第26回基礎有機化学討論会
    • Place of Presentation
      松山市 愛媛大学城北キャンパス・松山大学文京キャンパス
    • Year and Date
      2015-09-24
    • Related Report
      2015 Research-status Report
  • [Presentation] ビスジアゾ化合物を用いた複核希土類錯体の構造と光照射前後の磁性2015

    • Author(s)
      村島 健介・唐澤 悟・古賀 登
    • Organizer
      第65回錯体化学討論会
    • Place of Presentation
      奈良女子大学
    • Year and Date
      2015-09-21
    • Related Report
      2015 Research-status Report
  • [Presentation] ヘキサアザペンタセン誘導体の合成と光物性2015

    • Author(s)
      廣田 淳子・唐澤 悟・古賀 登
    • Organizer
      ,有機合成化学協会九州山口支部 第27回 若手研究者のためのセミナー
    • Place of Presentation
      福岡市、九州大学馬出キャンパスコラボステーション
    • Year and Date
      2015-08-29
    • Related Report
      2015 Research-status Report
  • [Presentation] オリゴエチレングリコール鎖を有する水溶性ポルフィリン誘導体の合成と水中での自己集合化挙動2015

    • Author(s)
      竪山大康・唐澤 悟・古賀 登
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学理工学部キャンパス
    • Year and Date
      2015-03-28
    • Related Report
      2014 Research-status Report
  • [Presentation] 様々な分子間結合部位を有する両親媒性分子の水中での自己集合化挙動2015

    • Author(s)
      岡本優菜・大橋枝里子・唐澤 悟・古賀 登
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学理工学部キャンパス
    • Year and Date
      2015-03-28
    • Related Report
      2014 Research-status Report
  • [Presentation] 温度応答性蛍光イメージングプローブの合成と水中での物性評価2015

    • Author(s)
      荒木 健・嶋田敬志・村山周平・唐澤 悟・青木伊知男・佐賀恒夫・古賀 登
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学理工学部キャンパス
    • Year and Date
      2015-03-28
    • Related Report
      2014 Research-status Report
  • [Presentation] キノリン誘導体の分子内光環化反応と自己集合挙動2015

    • Author(s)
      唐澤 悟・藤堂潤一・臼井一晃・末宗 洋・古賀 登
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学理工学部キャンパス
    • Year and Date
      2015-03-27
    • Related Report
      2014 Research-status Report
  • [Presentation] ジナフチリジルアミン誘導体の光反応挙動2015

    • Author(s)
      萩原隆一・唐澤 悟・古賀 登
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学理工学部キャンパス
    • Year and Date
      2015-03-27
    • Related Report
      2014 Research-status Report
  • [Presentation] ヘキサアザペンタセン誘導体の合成と光物性2015

    • Author(s)
      廣田淳子・原田奈央美・唐澤 悟・古賀 登
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学理工学部キャンパス
    • Year and Date
      2015-03-27
    • Related Report
      2014 Research-status Report
  • [Presentation] 種々の 3d 金属イオンを持つヘテロスピン複核錯体の合成とその 構造と磁性2015

    • Author(s)
      森 昂也・村島健介・唐澤 悟・古賀 登
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学理工学部キャンパス
    • Year and Date
      2015-03-27
    • Related Report
      2014 Research-status Report
  • [Presentation] 光応答型2p-3d-4fヘテロスピン一次元鎖錯体の構造と磁気的性質2015

    • Author(s)
      村島健介・唐澤 悟・古賀 登
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学理工学部キャンパス
    • Year and Date
      2015-03-27
    • Related Report
      2014 Research-status Report
  • [Presentation] がん集積を目指した超分子型造影剤の開発2015

    • Author(s)
      唐澤 悟
    • Organizer
      第2回東北大学リーディング大学院研究会
    • Place of Presentation
      東北大学理学部
    • Year and Date
      2015-02-21
    • Related Report
      2014 Research-status Report
  • [Presentation] 光応答型ヘテロスピンLn(III)二核錯体の構造と光照射前後の磁性2014

    • Author(s)
      村島健介・唐澤 悟・古賀 登
    • Organizer
      第64回錯体化学討論会
    • Place of Presentation
      中央大学後楽園キャンパス
    • Year and Date
      2014-09-19
    • Related Report
      2014 Research-status Report
  • [Presentation] 生体ケイ光プローブとしてのTFMAQ誘導体の応用2014

    • Author(s)
      嶋田敬志・唐澤 悟・藤本景子・田中嘉孝・古賀 登・村山周平・佐賀恒夫・青木伊知男
    • Organizer
      第25回基礎有機化学討論会
    • Place of Presentation
      東北大学川内キャンパス
    • Year and Date
      2014-09-08
    • Related Report
      2014 Research-status Report
  • [Presentation] 一置換及び二置換の両親媒性側鎖を持つウレニルベンゼン誘導体の合成と水中での自己集合化挙動2014

    • Author(s)
      岡本優菜・大橋枝里子・唐澤 悟・古賀 登
    • Organizer
      第25回基礎有機化学討論会
    • Place of Presentation
      東北大学川内キャンパス
    • Year and Date
      2014-09-07
    • Related Report
      2014 Research-status Report
  • [Presentation] アミノ基で連結されたビスナフチリジン誘導体の合成と光照射前後の構造と光物性2014

    • Author(s)
      萩原隆介・唐澤 悟・古賀 登
    • Organizer
      第25回基礎有機化学討論会
    • Place of Presentation
      東北大学川内キャンパス
    • Year and Date
      2014-09-07
    • Related Report
      2014 Research-status Report
  • [Presentation] 生体イメージングプローブを目指した水溶性ポルフィリン誘導体の合成と自己集合化挙動2014

    • Author(s)
      竪山大康・大久保研吾・唐澤 悟・古賀 登
    • Organizer
      第25回基礎有機化学討論会
    • Place of Presentation
      東北大学川内キャンパス
    • Year and Date
      2014-09-07
    • Related Report
      2014 Research-status Report
  • [Patent(Industrial Property Rights)] 温度応答性化合物2016

    • Inventor(s)
      古賀 登・唐澤 悟・荒木 健・森下 晃佑
    • Industrial Property Rights Holder
      九州大学・日産化学工業
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2016-046325
    • Filing Date
      2016-03-09
    • Related Report
      2015 Research-status Report

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Published: 2014-04-04   Modified: 2018-03-22  

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