Development of photofunctional molecules that generate calcium signals

• Project/Area Number: 22750143
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Single-year Grants
• Research Field: Chemistry related to living body
• Research Institution: University of Tsukuba
• Principal Investigator: MOMOTAKE Atsuya 筑波大学, 数理物質系, 講師 (70375369)
• Project Period (FY): 2010 – 2012
• Project Status: Completed (Fiscal Year 2012)
• Budget Amount: ¥3,640,000 (Direct Cost: ¥2,800,000、Indirect Cost: ¥840,000); Fiscal Year 2012: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000); Fiscal Year 2011: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000); Fiscal Year 2010: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
• Keywords: 光分解 / ケージド化合物 / カルシウムシグナル / 光誘起電子移動 / カルシウムシグナリング / 光分解反応 / 光化学 / 細胞イメージング / カルシウムイオン / 光神経科学

Research Abstract

In this research we aimed to improve photochemical efficiency of the molecules that are able to release calcium ion by photo excitation (caged calcium). The quantum yield for photolysis of new BAPTA-based caged calcium is found to low due to forming charge transfer complex in the ground state. On the other hands, we successfully developed novel photolabile protecting groups for caged calcium whose quantum yield of photolysis was more than 0.5.

Research Products

• [Journal Article] Photochemistry of arylacetylenyl-substituted stilbenes. Journal of Photochemistry and Photobiology (2013)
  • Author(s): Suzuki, M.; Momotake, A.; Kanna, Y.; Nishimura, Y.; Hirota, K.; Morihashi, K.; Arai, T.
  • Journal Title: A: Chemistry Volume: 252 Pages: 203-210
  • DOI: 10.1016/j.jphotochem.2012.11.019
  • Peer Reviewed
• [Journal Article] Excited state intramolecular hydrogen atom transfer of phenylethynyl-substituted 2'-hydroxychalcones (2013)
  • Author(s): Tasaki, S.; Momotake, A.; Kanna, Y.; Arai, T
  • Journal Title: Research on Chemical Intermediates Volume: 39 Issue: 1 Pages: 61-72
  • DOI: 10.1007/s11164-012-0632-8
  • Peer Reviewed
• [Journal Article] Extremely efficient photoisomerization of water-soluble diphenylbutadiene dendrimers (2012)
  • Author(s): Miura, Y.; Momotake, A.; Kanna, Y.; Nishimura, Y.; Arai, T
  • Journal Title: Dyes and Pigments Volume: 92 Pages: 802-806
  • Peer Reviewed
• [Journal Article] N-Acyl-N-carboxymethyl-2-nitroaniline and its analogues: a new class of water-soluble photolabile precursor of carboxylic acids (2012)
  • Author(s): Honda, T.; Momotake, A.; Arai, T
  • Journal Title: Photochem. Photobiol. Sci Volume: 11 Issue: 3 Pages: 493-496
  • DOI: 10.1039/c2pp05322e
  • Peer Reviewed
• [Journal Article] Environmental polarity estimation in living cells by use of quinoxaline-based full-colored solvatochromic fluorophore PQX and its derivatives (2012)
  • Author(s): Kudo, et al
  • Journal Title: Photochem Photobiol Sci Volume: 11 Issue: 4 Pages: 674-678
  • DOI: 10.1039/c2pp05337c
  • Peer Reviewed
• [Journal Article] 2-(N-acyl-N-carboxymethylamino)-1-nitrodibenzo[b,d]thiophene: a new class of caging group for environmental selective photorelease of carboxylic acid. (2012)
  • Author(s): Tanaka, Y.; Momotake, A.; Arai, T
  • Journal Title: Chemistry Letters 2012 Volume: 41 Issue: 6 Pages: 642-643
  • DOI: 10.1246/cl.2012.642
  • NAID: 130004426596
  • Peer Reviewed
• [Journal Article] Polarity-dependent photophysical properties of hemicyanine dyes and their application in 2-photon microscopy biological imaging. (2012)
  • Author(s): Kimura, Y., Momotake, A., Takahashi, N., Kasai, H. & Arai, T.
  • Journal Title: Chemistry Letters Volume: 41 Issue: 5 Pages: 528-530
  • DOI: 10.1246/cl.2012.528
  • NAID: 10030619751
  • Peer Reviewed
• [Journal Article] Self-assembly of a poly(glutamate) dendrimer: solventdependent expression of molecular chirality and a [2 + 2] photocrosslinking reaction (2012)
  • Author(s): Ikeda, M.; Momotake, A.; Kanna, Y.; Shimotori, K.; Arai, T.
  • Journal Title: Photochemical & Photobiological Sciences Volume: 11 Issue: 10 Pages: 1524-1527
  • DOI: 10.1039/c2pp25221j
  • Peer Reviewed
• [Journal Article] Synthetic localized calcium transients directly probe signalling mechanisms in skeletal muscle (2012)
  • Author(s): Figueroa, L.
  • Journal Title: Journal of Physiology Volume: 590 Issue: 6 Pages: 1389-1411
  • DOI: 10.1113/jphysiol.2011.225854
  • Peer Reviewed
• [Journal Article] The use of dendrimers as high-performance shells for round-trip energy transfer: efficient trans-cis photoisomerization from an excited triplet state produced within a dendrimer shell. (2011)
  • Author(s): Miura, Y.; Momotake, A.; Takeuchi, K.; Arai, T.
  • Journal Title: Photochem. Photobiol. Sci Volume: 10 Issue: 1 Pages: 116-122
  • DOI: 10.1039/c0pp00272k
  • Peer Reviewed
• [Journal Article] Singlet molecular oxygen generation by water-soluble phthalocyanine dendrimers with different aggregation behavior (2011)
  • Author(s): Nishida, M.; Horiuchi, H.; Momotake, A.; Nishimura, Y.; Hiratsuka, H.; Arai, T
  • Journal Title: Porphyrins and Phthalocyanines Volume: 15 Pages: 47-53
  • Peer Reviewed
• [Journal Article] Development of a quinoxaline-based fluorescent probe for quantitative estimation of protein binding site polarity (2011)
  • Author(s): Kudo, K.; Momotake, A.; Kanna, Y.; Nishimura, Y.; Arai, T.
  • Journal Title: Chem. Commun Volume: 47 Issue: 13 Pages: 3867-3869
  • DOI: 10.1039/c1cc10183h
  • Peer Reviewed
• [Journal Article] Energy Transfer and trans-cis Isomerization in Dendrimer Aggregates (2011)
  • Author(s): Miura. Y.; Momotake, A.; Kanna, Y.; Nishimura, Y.; Arai, T.
  • Journal Title: Bull. Chem. Soc. Jpn Volume: 84 Pages: 363-365
  • NAID: 10028046713
  • Peer Reviewed
• [Journal Article] Extremely efficient and long lifetime fluorescence of cis-stilbene contained in a rigid dendrimer. (2011)
  • Author(s): Tabuchi, M.; Momotake, A.; Kanna, Y.; Nishimura, Y.; Arai, T
  • Journal Title: Photochemical & Photobiological Sciences 2011 Volume: 10 Issue: 10 Pages: 1521-1523
  • DOI: 10.1039/c1pp05126a
  • Peer Reviewed
• [Journal Article] Observation of Anthracene Excimer Fluorescence at Very Low Concentrations Utilizing Dendritic Structures, J. Photochem (2011)
  • Author(s): Akatsuka R.; Momotake, A.; Shinohara, Y.; Kanna, Y.; Sato, T.; Moriyama, M.; Takahashi, K.; Nishimura, Y.; Arai, T
  • Journal Title: Photbiol. A: Chem. Volume: 223 Pages: 1-5
  • Peer Reviewed
• [Journal Article] Unusually efficient trans-to-cis photoisomerization of diphenylbutadiene dendrimers in water (2011)
  • Author(s): Miura. Y.; Momotake, A.; Kanna, Y.; Nishimura, Y.; Arai, T.
  • Journal Title: Photochem. Photobiol. Sci Volume: 10 Issue: 10 Pages: 1524-1526
  • DOI: 10.1039/c1pp05212h
  • Peer Reviewed
• [Journal Article] Spatial distributions of GABA receptors and local inhibition of Ca^<2+> transients studied with GABA uncaging in the dendrites of CA1 pyramidal neurons (2011)
  • Author(s): Yuya Kanemoto, Masanori Matsuzaki, Susumu Morita, Tatsuya Hayama, Jun Noguchi, Naoko Senda, Atsuya Momotake, Tatsuo Arai, Haruo Kasai
  • Journal Title: PLoS One Volume: 6 Issue: 7 Pages: e22652-e22652
  • DOI: 10.1371/journal.pone.0022652
  • Peer Reviewed
• [Journal Article] Energy Transfer and trans-cis Isomerization in Dendrimer Aggregates (2011)
  • Author(s): Miura. Y.
  • Journal Title: Bull.Chem.Soc.Jpn. Volume: 84 Issue: 4 Pages: 363-365
  • DOI: 10.1246/bcsj.20100318
  • NAID: 130004152891
  • Peer Reviewed
• [Journal Article] Observation of Anthracene Excimer Fluorescence at Very Low Concentrations Utilizing Dendritic Structures (2011)
  • Author(s): Akatsuka R.
  • Journal Title: J.Photochem.Phothiol.A : Chem. Volume: 223 Issue: 1 Pages: 1-5
  • DOI: 10.1016/j.jphotochem.2011.07.008
  • Peer Reviewed
• [Journal Article] Singlet molecular oxygen generation by water-soluble phthalocyanine dendrimers with different aggregation behavior. (2011)
  • Author(s): Nishida, M.
  • Journal Title: Journal of Porphyrins and Phthalocyanines Volume: 15 Pages: 47-53
  • Peer Reviewed
• [Journal Article] The use of dendrimers as high-performance shells for round-trip energy transfer : efficient trans-cis photoisomerization from an excited triplet state produced within a dendrimer shell. (2011)
  • Author(s): Miura, Y.
  • Journal Title: Photochemical & Photobiological Sciences Volume: 10 Pages: 116-122
  • Peer Reviewed
• [Journal Article] Development of a quinoxaline-based fluorescent probe for quantitative estimation of protein binding site polarity. (2011)
  • Author(s): Kudo, K.
  • Journal Title: Chemical Communications Volume: 47 Pages: 3867-3869
  • Peer Reviewed
• [Journal Article] 1-Acyl-5-methoxy-8-nitro-1,2-dihydroquinoline: a biologically useful photolabile precursor of carboxylic acids (2010)
  • Author(s): Obi, N.; Momotake, A.; Kanemoto, Y.; Matsuzaki, M.; Kasai, H.; Arai, T
  • Journal Title: Tetrahedron Lett Volume: 51 Issue: 13 Pages: 1642-1647
  • DOI: 10.1016/j.tetlet.2009.12.081
  • Peer Reviewed
• [Journal Article] Fluorescence enhancement in 7-hydroxyquinoline analogs by methyl substitution and their spectroscopic characteristics in aqueous solution (2010)
  • Author(s): Senda, N.; Momotake, A.; Arai, T
  • Journal Title: Bull. Chem. Soc. Jpn Volume: 83 Issue: 10 Pages: 1272-1274
  • DOI: 10.1246/bcsj.20100119
  • NAID: 130004058976
  • Peer Reviewed
• [Journal Article] Substituent effect of 7-hydroxy-1-methylquinolinium derivatives: a photochemical approach to development of new fluorescent pH indicator (2010)
  • Author(s): Senda, N.; Momotake, A.; Arai, T
  • Journal Title: Heterocycles Volume: 81 Issue: 10 Pages: 2343-2350
  • DOI: 10.3987/com-10-11996
  • NAID: 40017284225
  • Peer Reviewed
• [Journal Article] Photochemistry of Linear-Shaped Phenylacetylenyl- and (Phenylacetylenyl)phenylacetylenyl-Substituted Aromatic Enediynes (2010)
  • Author(s): Sugiyama, Y.; Shinohara, Y.; Momotake, A.; Takahashi, K.; Kanna, Y.; Nishimura,Y.; Arai, T.
  • Journal Title: J. Phys. Chem. A Volume: 114 Issue: 41 Pages: 10929-10935
  • DOI: 10.1021/jp1054827
  • Peer Reviewed
• [Journal Article] Photochemistry of Linear-Shaped Phenylacetylenyl- and (Phenylacetylenyl)phenylacetylenyl-Substituted Aromatic Enediynes. (2010)
  • Author(s): Sugiyama, Y.
  • Journal Title: Journal of Physical Chemistry A Volume: 114 Pages: 10929-10935
  • Peer Reviewed
• [Journal Article] Substituent effect of 7-hydroxy-1-methylquinolinium derivatives : a photochemical approach to development of new fluorescent pH indicator. (2010)
  • Author(s): Senda, N.
  • Journal Title: Heterocycles Volume: 81 Pages: 2343-2350
  • Peer Reviewed
• [Journal Article] Fluorescence enhancement in 7-hydroxyquinoline analogs by methyl substitution and their spectroscopic characteristics in aqueous solution. (2010)
  • Author(s): Senda, N.
  • Journal Title: Bulletin of the Chemical Society of Japan Volume: 83 Pages: 1272-1274
  • Peer Reviewed
• [Presentation] ニトロベンゼン骨格を活用したケージド化合物合成への展開 (2012)
  • Author(s): 高橋洋平・百武篤也・新井達郎
  • Organizer: 光化学討論会
  • Place of Presentation: 東京工業大学大岡山キャンパス
  • Year and Date: 2012-09-14
• [Presentation] 光誘起電子移動経由でカルボン酸を放出するケージド化合物の研究 (2012)
  • Author(s): 森山晴加・百武篤也・新井達郎
  • Organizer: 光化学討論会
  • Place of Presentation: 東京工業大学大岡山キャンパス
  • Year and Date: 2012-09-13
• [Presentation] ニトロベンゼン骨格を有する新規ケージド化合物の合成と光化学的挙動 (2012)
  • Author(s): 高橋 洋平・百武篤也・新井 達郎
  • Organizer: 日本化学会第92 春季年会
  • Place of Presentation: 慶應義塾大学日吉キャンパス・矢上キャンパス
  • Year and Date: 2012-03-26
• [Presentation] 新規アゾベンゼン色素の光化学的特性とそれらを利用した細胞膜イメージングへの応用に関する研究 (2012)
  • Author(s): 福嶋 瞬・百武篤也・新井 達郎
  • Organizer: 日本化学会第92 春季年会
  • Place of Presentation: 慶應義塾大学日吉キャンパス・矢上キャンパス
  • Year and Date: 2012-03-26
• [Presentation] ドナー・アクセプター型アゾベンゼンの光化学的挙動とイオンセンシングに関する研究 (2012)
  • Author(s): 福嶋瞬・百武篤也・新井達郎
  • Organizer: 光化学討論会
  • Place of Presentation: 東京工業大学大岡山キャンパス
• [Presentation] 光誘起電子移動経由でカルボン酸を放出するケージド化合物の研究 (2012)
  • Author(s): 森山晴加
  • Organizer: 2012光化学討論会
  • Place of Presentation: 東京工業大大岡山キャンパス
• [Presentation] ニトロベンゼン骨格を活用したケージド化合物合成への展開 (2012)
  • Author(s): 高橋洋平
  • Organizer: 2012光化学討論会
  • Place of Presentation: 東京工業大大岡山キャンパス
• [Presentation] ドナー・アクセプター型アゾベンゼンの光化学的挙動とイオンセンシングに関する研究 (2012)
  • Author(s): 福嶋瞬
  • Organizer: 2012光化学討論会
  • Place of Presentation: 東京工業大大岡山キャンパス
• [Presentation] キノキサリン系蛍光プローブの開発と光化学的性質 (2011)
  • Author(s): 森山晴加
  • Organizer: 第5回バイオ関連化学シンポジウム
  • Place of Presentation: つくば国際会議場
  • Year and Date: 2011-09-13
• [Presentation] スチルベン骨格を中心に有するペプチドデンドリマーの光化学 (2011)
  • Author(s): 池田愛
  • Organizer: 第5回バイオ関連化学シンポジウム
  • Place of Presentation: つくば国際会議場
  • Year and Date: 2011-09-12
• [Presentation] 光誘起電子移動を利用したケージドグルタミン酸の分解と高機能化に関する研究 (2011)
  • Author(s): 百武篤也
  • Organizer: 第5回バイオ関連化学シンポジウム
  • Place of Presentation: つくば国際会議場
  • Year and Date: 2011-09-12
• [Presentation] ポリグルタミン酸デンドリマーの光化学的特性 (2011)
  • Author(s): 池田愛・百武篤也・新井達郎
  • Organizer: 光化学討論会
  • Place of Presentation: 宮崎市河畔コンベンションエリア, 宮崎市
  • Year and Date: 2011-09-08
• [Presentation] 光誘起電子移動反応を利用したケージドグルタミン酸の高性能化に関する研究 (2011)
  • Author(s): 森山晴加・百武篤也・西村賢宣・新井達郎
  • Organizer: 光化学討論会
  • Place of Presentation: 宮崎市河畔コンベンションエリア, 宮崎市
  • Year and Date: 2011-09-08
• [Presentation] Photochemical characteristics of poly (glutamate)dendrimers (2011)
  • Author(s): IKEDA, Megumi
  • Organizer: 2011光化学討論会
  • Place of Presentation: 宮崎市民プラザ
  • Year and Date: 2011-09-08
• [Presentation] Study on photoinduced electron transfer reaction to induce highly efficient photolysis for cagedglutamates (2011)
  • Author(s): MORIYAMA, Haruka
  • Organizer: 2011光化学討論会
  • Place of Presentation: 宮崎市民プラザ
  • Year and Date: 2011-09-08
• [Presentation] ニトロフルオレンまたはニトロジベンゾチオフェンを用いた新規ケージド化合物の合成とその光化学 (2011)
  • Author(s): 田中佑二・百武篤也・新井達郎
  • Organizer: 光化学討論会
  • Place of Presentation: 宮崎市河畔コンベンションエリア, 宮崎市
  • Year and Date: 2011-09-07
• [Presentation] Synthesis and substituent effect of caged compounds using nitroaniline skeleton (2011)
  • Author(s): HONDA, Takuya
  • Organizer: 2011光化学討論会
  • Place of Presentation: 宮崎市民プラザ
  • Year and Date: 2011-09-07
• [Presentation] エステル表面官能基を有するベンジルエーテル型スチルベンデンドリマーの光化学的挙動と溶媒効果 (2011)
  • Author(s): 滝澤努・ 百武篤也 ・西村賢宣・新井達郎
  • Organizer: 光化学討論会
  • Place of Presentation: 宮崎市河畔コンベンションエリア, 宮崎市
  • Year and Date: 2011-09-06
• [Presentation] ニトロアニリン骨格を用いたケージド化合物の合成と置換基効果 (2011)
  • Author(s): 本田拓也・百武篤也・新井達郎
  • Organizer: 光化学討論会
  • Place of Presentation: 宮崎市河畔コンベンションエリア, 宮崎市
  • Year and Date: 2011-09-06
• [Presentation] Photochemical behavior and solvent effect of poly(benzyl ether)stilbene dendrimerswith ester surface functional groups (2011)
  • Author(s): TAKIZAWA, Tsutomu
  • Organizer: 2011光化学討論会
  • Place of Presentation: 宮崎市民プラザ
  • Year and Date: 2011-09-06
• [Presentation] 脂溶性ポリグルタミン酸デンドリマーの光化学的挙動 (2011)
  • Author(s): 池田愛
  • Organizer: 日本化学会第5回関東支部大会(2011)
  • Place of Presentation: 東京農工大学小金井キャンパス(東京都小金井市)
  • Year and Date: 2011-08-30
• [Presentation] 2光子励起法を利用した細胞膜染色に用いる蛍光プローブの開発 (2010)
  • Author(s): 木村勇太
  • Organizer: 2010年光化学討論会
  • Place of Presentation: 千葉大学西千葉キャンパス
  • Year and Date: 2010-09-09
• [Presentation] ベンジルエーテル型スチルベンデンドリマーの光化学的特性に及ぼす表面官能基の効果 (2010)
  • Author(s): 滝澤努
  • Organizer: 2010年光化学討論会
  • Place of Presentation: 千葉大学西千葉キャンパス
  • Year and Date: 2010-09-09
• [Presentation] ニトロフルオレン骨格を用いた新規ケージング基の開発 (2010)
  • Author(s): 田中佑二
  • Organizer: 日本化学会第4回関東支部大会
  • Place of Presentation: 筑波大学
  • Year and Date: 2010-08-31
• [Presentation] C=C二重結合を有する蛍光性キノキサリン-ピロール連結化合物のソルバトクロミック特性 (2010)
  • Author(s): 工藤健太郎
  • Organizer: 日本化学会第4回関東支部大会
  • Place of Presentation: 筑波大学
  • Year and Date: 2010-08-30