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Development of new channelrhodpsin having the long conjugated chromophore

Research Project

Project/Area Number 26450146
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Bioorganic chemistry
Research InstitutionKobe Pharmaceutical University

Principal Investigator

WADA Akimori  神戸薬科大学, 薬学部, 教授 (80158683)

Co-Investigator(Renkei-kenkyūsha) SHICHIDA Yoshinori  京都大学, 大学院・理学研究科, 教授 (60127090)
Project Period (FY) 2014-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥5,070,000 (Direct Cost: ¥3,900,000、Indirect Cost: ¥1,170,000)
Fiscal Year 2016: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2015: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2014: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Keywordsチャネルロドプシン / 発色団 / 長い共役系 / 赤色光 / レチナール / ケミカルバイオロジー / 共役系 / 長波長吸収 / オプトジェネティクス / チャンネルロドプシン
Outline of Final Research Achievements

Optogenetics is a powerful new tool, which allows control of neuronal activity by light. Channelrhodopsins are light-gated cation channels and have been used for optogenetics. In order to construct a new type of channelrhodopsin having the chromophore responding to the longer wavelength, we prepared the novel retinal analogs with double bond-elongated at the Schiff base, side chain or cyclohexene ring of retinal and 3,4-dehyrdoretinal.All analogs synthesized here bound to apo-protein to afford the new channelrhodopsins. Although the red shift values of ramuda max were only 10-20 nm, these channelrhodopsins exhibited the half of absorption maximum at about 560-580 nm, which were about 50-80 nm red shifted than that of native channelrhodopsin.

Report

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

    (32 results)

All 2017 2016 2015 2014

All Journal Article (17 results) (of which Int'l Joint Research: 2 results,  Peer Reviewed: 17 results,  Acknowledgement Compliant: 5 results,  Open Access: 1 results) Presentation (15 results) (of which Int'l Joint Research: 2 results)

  • [Journal Article] Alternative Formation of Red-Shifted Channelrhodopsins: Noncovalent Incorporation with Retinal-Based Enamine-Type Schiff Bases and Mutated Channelopsin2017

    • Author(s)
      T. Okitsu
    • Journal Title

      Chemical and Pharmaceutical Bulletin

      Volume: 65 Issue: 4 Pages: 356-358

    • DOI

      10.1248/cpb.c17-00054

    • NAID

      130005529782

    • ISSN
      0009-2363, 1347-5223
    • Related Report
      2016 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Solid-state NMR structural study of retinal-binding pocket in sodium ion pump rhodopsin.2017

    • Author(s)
      Arisu Shigeta, Shota Ito, Keiichi Inoue, Takashi Okitsu, Akimori Wada, Hideki Kandori, Izuru Kawamura*
    • Journal Title

      Biochemistry

      Volume: 56 Issue: 4 Pages: 543-550

    • DOI

      10.1021/acs.biochem.6b00999

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Convergent Synthesis of Dronedarone, an Antiarrhythmic Agent2016

    • Author(s)
      Okitsu, T.; Ogasahara, M.; Wada, A.
    • Journal Title

      Chemical and Pharmaceutical Bulletin

      Volume: 64 Issue: 8 Pages: 1149-1153

    • DOI

      10.1248/cpb.c16-00237

    • NAID

      130005253909

    • ISSN
      0009-2363, 1347-5223
    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Modulation of thermal noise and spectral sensitivity in Lake Baikal cottoid fish rhodopsins2016

    • Author(s)
      Luk, H. L.; Bhattacharyya, N.; Montisci, F.; Morrow, J. M.; Melaccio, F.; Wada, A.; Sheves, M.; Fanelli, F.; Chang, B. S. W.; Olivucci, M.
    • Journal Title

      Sci. Rep.

      Volume: 6 Issue: 1 Pages: 38425-38425

    • DOI

      10.1038/srep38425

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Anti-Oxidative Activity of Mytiloxanthin, a Metabolite of Fucoxanthin in Shellfish and Tunicates2016

    • Author(s)
      Maoka, T.; Nishino, A.; Yasui, H.; Yamano, Y.; Wada, A.
    • Journal Title

      Mar. Drugs

      Volume: 14 Issue: 5 Pages: 93-93

    • DOI

      10.3390/md14050093

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Oxidative Metabolites of Lycopene and -Carotene in Gac (Momordica cochinchinensis)2015

    • Author(s)
      Maoka, T.; Yamano, Y.; Wada, A.; Etho, T.; Terada, Y.; Tokuda, H.; Nishino, H
    • Journal Title

      J. Agric. Food Chem.

      Volume: 63 Issue: 5 Pages: 1622-1630

    • DOI

      10.1021/jf505008d

    • Related Report
      2015 Research-status Report
    • Peer Reviewed
  • [Journal Article] Total synthesis of gobiusxanthin stereoisomers and their application to determination of absolute configurations of natural products: revision of reported absolute configuration of epigobiusxanthin2015

    • Author(s)
      Yamano, Y.; Ematsu, K.; Kurimoto, H.; Maoka, T.; Wada, A.
    • Journal Title

      Mar. Drugs

      Volume: 13 Issue: 1 Pages: 159-172

    • DOI

      10.3390/md13010159

    • Related Report
      2015 Research-status Report
    • Peer Reviewed
  • [Journal Article] Stereocontrolled First Total Syntheses of Salmoxanthin and Deepoxysalmoxanthin2015

    • Author(s)
      Yamano, Y.; Eno, K.; Hikita, Y.; Kurimoto, H.; Wada, A.
    • Journal Title

      Curr. Org. Synth.

      Volume: 12 Issue: 2 Pages: 180-188

    • DOI

      10.2174/1570179411999141106102507

    • Related Report
      2015 Research-status Report
    • Peer Reviewed
  • [Journal Article] Identical hydrogen-bonding strength of the retinal Schiff base between primate green- and red-sensitive pigments: New insight into color tuning mechanism2015

    • Author(s)
      K. Katayama, T. Okitsu, H. Imai, A. Wada, H. Kandori*
    • Journal Title

      J. Phys. Chem. Lett

      Volume: 6 Issue: 7 Pages: 1130-1133

    • DOI

      10.1021/acs.jpclett.5b00291

    • Related Report
      2015 Research-status Report
    • Peer Reviewed
  • [Journal Article] Characterization of photo-intermediates in the photo-reaction pathways of a bacteriorhodopsin Y185F mutant using in situ photo-irradiation solid-state NMR spectroscopy2015

    • Author(s)
      Kyosuke Oshima, Aris Shigeta, Yoshiteru Makino, Izuru Kawamura, Takashi Okitsu, Akimori Wada, Satoru Tuzi, Tetsuo Iwasa, Akira Naito
    • Journal Title

      Photochem. Photobiol. Sci.

      Volume: 14 Issue: 9 Pages: 2015-2015

    • DOI

      10.1039/c5pp00154d

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Origin of the low thermal isomerization rate of rhodopsin chromophore2015

    • Author(s)
      Yanagawa, M.; Kojima, K.; Yamashita, T.; Iwamoto, Y.; Matsuyama, T.; Nakanishi, K.; Yamano, Y.; Wada, A.; Sako, Y.; Shichida, Y.
    • Journal Title

      Sci. Rep.

      Volume: 5 Issue: 1 Pages: 11081-11081

    • DOI

      10.1038/srep11081

    • NAID

      120005690204

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Ligand-induced population shift leads to the activation of rhodopsin, a G-protein coupled receptor2014

    • Author(s)
      Maeda, R., Hiroshima, M., Yamashita, T., Wada, A., Nishimura, S., Sako, Y., Shichida, Y., and Imamoto, Y
    • Journal Title

      Biophys. J

      Volume: 106 (4) Issue: 4 Pages: 915-924

    • DOI

      10.1016/j.bpj.2014.01.020

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Journal Article] Inhibition of lysine-specific demethylase 1 by the acyclic diterpenoid geranylgeranoic acid and its derivatives.2014

    • Author(s)
      Sakane C, Okitsu T, Wada A, Sagami H, Shidoji Y.
    • Journal Title

      Biochem Biophys Res Commun.

      Volume: 444 Issue: 1 Pages: 24-29

    • DOI

      10.1016/j.bbrc.2013.12.144

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis of (3S,3S')- and meso-stereoisomers of alloxanthin and determination of absolute configuration of alloxanthin isolated from aquatic animals2014

    • Author(s)
      Yamano, Y.; Maoka, T.; Wada, A.
    • Journal Title

      Mar. Drugs

      Volume: 12 Issue: 5 Pages: 2626-2632

    • DOI

      10.3390/md12052623

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Journal Article] Iodocyclization of Ethoxyethyl Ethers to Ynamides: An Immediate Construction to Benzo[b]furans2014

    • Author(s)
      Okitsu, T.; Nakata, K.; Nishigaki, K.; Michioka, N.; Karatani, M.; Wada, A.
    • Journal Title

      J. Org. Chem.

      Volume: 79 Pages: 5914-5920

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Journal Article] Color Discriminating Retinal Configurations of Sensory Rhodopsin I by Photo-Irradiation Solid State NMR Spectroscopy.2014

    • Author(s)
      H. Yomonda, Y. Makino, Y. Tomonaga, T. Hidaka, I. Kawamura*, T. Okitsu, A. Wada, Y. Sudo*, A. Naito*.
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 53 Issue: 27 Pages: 6960-6964

    • DOI

      10.1002/anie.201309258

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] ビタミンA誘導体を用いた生物有機化学的研究2014

    • Author(s)
      和田 昭盛
    • Journal Title

      ビタミン

      Volume: 88 Pages: 72-81

    • NAID

      110009805253

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Presentation] レチナール環構造に共役系を導入したアナログの合成とタンパク質オプシンとの相互作用2016

    • Author(s)
      和田昭盛、山野由美子、沖津貴志、山下高廣、今元泰、七田芳則
    • Organizer
      日本レチノイド研究会第27学術集会
    • Place of Presentation
      町田
    • Year and Date
      2016-10-22
    • Related Report
      2016 Annual Research Report
  • [Presentation] 共役したクロメン環を有するレチナールアナログの合成研究2016

    • Author(s)
      神崎さくら子、石井菜紬子、沖津貴志、和田昭盛
    • Organizer
      日本ビタミン学会第68回大会
    • Place of Presentation
      富山
    • Year and Date
      2016-06-18
    • Related Report
      2016 Annual Research Report
  • [Presentation] Iodonium-mediated dearomative cyclization/Diels-Alder tandem of a chiral ynamide toward diastereoselective construction of bridgehead-spiro system2015

    • Author(s)
      Okitsu, T.; Murai, C.; Wada, A.
    • Organizer
      Pacifichem 2015
    • Place of Presentation
      Honolulu/USA
    • Year and Date
      2015-12-19
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] Lycopeneの新規酸化代謝物、lycopene-5,6-diol立体異性体の全合成2015

    • Author(s)
      山野 由美子、西山 裕也、青木 敦志、和田 昭盛
    • Organizer
      第41回反応と合成の進歩シンポジウム
    • Place of Presentation
      東大阪
    • Year and Date
      2015-10-26
    • Related Report
      2015 Research-status Report
  • [Presentation] イナミドの求電子性が促進する6-endo-dig環化:ピリダジン類の制御合成2015

    • Author(s)
      沖津 貴志、森澤 祐介、本村 映人、和田 昭盛
    • Organizer
      第41回反応と合成の進歩シンポジウム
    • Place of Presentation
      東大阪
    • Year and Date
      2015-10-26
    • Related Report
      2015 Research-status Report
  • [Presentation] Preparation of New ChR with One Double Bond-elongated 3,4-Dehydroretinals2015

    • Author(s)
      Wada, A.; Okitsu, T.; Yamano, Y.; Kobayashi, Y.; Ishizuka, T.; Yawo, H.; Matsuyama, T.; Yamashiya, T.; Imamoto, Y.; Shichida, Y.
    • Organizer
      The 3rd International Conference on Retinoids
    • Place of Presentation
      Gifu/Japan
    • Year and Date
      2015-10-21
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] ガックより単離されたlycopene-5,6-diolおよびγ-carotene-5’,6’-diolの立体異性体の合成とHPLC分離条件の確立2015

    • Author(s)
      山野 由美子、西山 裕也、青木 敦志、和田 昭盛、眞岡 孝至
    • Organizer
      第29回カロテノイド研究談話会
    • Place of Presentation
      八王子
    • Year and Date
      2015-09-04
    • Related Report
      2015 Research-status Report
  • [Presentation] 3-メチレン-4-アミド-1,2-ジアゼチジンの求核的開環反応2014

    • Author(s)
      沖津 貴志、小林 恵子、吉田 淳美、吉田 裕司、和田 昭盛
    • Organizer
      第40回反応と合成の進歩シンポジウム
    • Place of Presentation
      仙台
    • Year and Date
      2014-11-10
    • Related Report
      2014 Research-status Report
  • [Presentation] β-ジケトン構造を有するアセチレンカロテノイドmytiloxanthinの立体選択的全合成2014

    • Author(s)
      山野 由美子、大畑 雅裕、和田 昭盛
    • Organizer
      第40回反応と合成の進歩シンポジウム
    • Place of Presentation
      仙台
    • Year and Date
      2014-11-10
    • Related Report
      2014 Research-status Report
  • [Presentation] 7-ヒドロキシレチノイン酸の合成と生物活性2014

    • Author(s)
      和田 昭盛、山野 由美子、笠原 奈那子、脇本 友絵、中川 公恵、岡野 登志夫
    • Organizer
      日本レチノイド研究会第25回学術集会
    • Place of Presentation
      秋田
    • Year and Date
      2014-10-11
    • Related Report
      2014 Research-status Report
  • [Presentation] Preparation of Red-Shifted PSB of Retinal Having Enamine Structure2014

    • Author(s)
      Wada, A.; Okitsu, T.; Futamura, N.; Niimi, Y.; Ishizuka, T.; Yawo, H.; Matsuyama Hoyos, T.; Yamashiya, T.; Shichida, Y.
    • Organizer
      16th International Conference on Retinal Proteins
    • Place of Presentation
      Nagahama
    • Year and Date
      2014-10-05 – 2014-10-10
    • Related Report
      2014 Research-status Report
  • [Presentation] イナミドのヨード環化反応を利用したベンゾフランの即時合成2014

    • Author(s)
      沖津 貴志、中田 康平、西垣 賢志、道岡 直幸、柄谷 光章、和田 昭盛
    • Organizer
      第17回ヨウ素学会シンポジウム
    • Place of Presentation
      千葉
    • Year and Date
      2014-09-19
    • Related Report
      2014 Research-status Report
  • [Presentation] mytiloxanthinの立体選択的全合成2014

    • Author(s)
      山野 由美子、大畑 雅裕、和田 昭盛
    • Organizer
      第28回カロテノイド研究談話会
    • Place of Presentation
      金沢
    • Year and Date
      2014-09-05
    • Related Report
      2014 Research-status Report
  • [Presentation] ガックに含まれる-Caroteneの酸化代謝産物について2014

    • Author(s)
      眞岡 孝至、山野 由美子、和田 昭盛
    • Organizer
      第28回カロテノイド研究談話会
    • Place of Presentation
      金沢
    • Year and Date
      2014-09-05
    • Related Report
      2014 Research-status Report
  • [Presentation] 3-メチレン-4-アミド-1,2-ジアゼチジンへのアリルシランの求核的開環反応2014

    • Author(s)
      沖津 貴志、小林 恵子、吉田 淳美、和田 昭盛
    • Organizer
      第34回有機合成若手セミナー
    • Place of Presentation
      神戸
    • Year and Date
      2014-08-05
    • Related Report
      2014 Research-status Report

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

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