Clarification of Mechanisms on DNA Damage by Electron-Transfer Reduction and Radical Species

2008 Fiscal Year Final Research Report

• Project/Area Number: 19750034
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Single-year Grants
• Research Field: Organic chemistry
• Research Institution: Osaka University
• Principal Investigator: OHKUBO Kei Osaka University, 大学院工学研究科, 特任研究員 (00379140)
• Project Period (FY): 2007 – 2008
• Keywords: 有機物理化学 / 電子移動化学

Research Abstract

DNAの損傷は突然変異を引き起こし、細胞の死やがん化の原因となる。そのためこのDNA損傷の化学反応を制御する機構の解明は、次世代の医療の新手法開発にもつながる極めて重要な課題である。本研究では、様々なラジカル種(アルキルラジカル・活性酸素種)とDNAおよび核酸塩基との反応について、中間体の検出や各種速度論的解析の結果をもとに損傷機構の解明を行った。

Research Products

• [Journal Article] Aliphatic C-H Bond Activation Initiated by a (μ-η^2:η2-Peroxo)dicopper(II) Complex in Comparison with Cumylperoxyl Radical (2009)
  • Author(s): Matsumoto, T., Ohkubo, K., Honda, K., Yazawa, A., Furutachi, H., Fujinami, S.,; Fukuzumi, S., Suzuki, M.
  • Journal Title: J. Am. Chem. Soc. 131(in press)
• [Journal Article] Tuning Charge Transfer in Novel Reaction Center Mimics Based on Th-Functionalized Fullerenes (2009)
  • Author(s): Spanig F., Kovacs, C., Hauke, F., Hartnagel, U., Ohkubo, K., Fukuzumi, S., Guldi, D. M., Hirsch, A.
  • Journal Title: J. Am. Chem. Soc. 131(in press)
• [Journal Article] Photoinduced Electron-Transfer Reduction of a Hydrochloride Salt of Dodecaphenylporphyrin with Conformational Distortion (2009)
  • Author(s): Nakanishi, T., Kojima, T., Ohkubo, K., Fukuzumi, S.
  • Journal Title: J. Am. Chem. Soc. 131 Pages: 577-584
• [Journal Article] Metal Quinolinolate-Fullerene(s) Donor-Acceptor Complexes: Evidence for Organic LED Molecules Acting as Electron Donors in Photoinduced Electron-Transfer Reactions (2008)
  • Author(s): D'Souza, F., Maligaspe, E., Zandler, M. E., Subbaiyan, N. K., Ohkubo, K., Fukuzumi, S.
  • Journal Title: J. Am. Chem. Soc. 130 Pages: 16959-16967
• [Journal Article] "Umpolung" Photoinduced Charge Separation in an Anion-bound Supramolecular Complex (2008)
  • Author(s): Sessler, J. L., Karnas, E., Kim, S. K., Ou, Z., Zhang, M., Kadish, K. M., Ohkubo, K., Fukuzumi, S.
  • Journal Title: J. Am. Chem. Soc. 130 Pages: 15256-15257
• [Journal Article] Proton Shift upon One-Electron Reduction in Ruthenium-Coordinated Pterins (2008)
  • Author(s): Miyazaki, S., Ohkubo, K., Kojima, T., Fukuzumi, S.
  • Journal Title: Angew. Chem. Int. Ed. 47 Pages: 9669-9672
• [Journal Article] (Pentamethylcyclopentadienyl)ruthenium π-Complexes of Metalloporphyrins: Platforms with Novel Photo- and Electrochemical Properties (2008)
  • Author(s): Cuesta, L., Karnas, E., Kynch, V. M., Sessler, J. L., Kajonkijya, W., Zhu, W., Zhang, M., Ou, Z., Kadish, K. M., Ohkubo, K., Fukuzumi, S.
  • Journal Title: Chem. Eur. J. 14 Pages: 10206-10210
• [Journal Article] Highly Selective Synthesis of the Ring-B Reduced Chlorins by Ferric Chloride Mediated Oxidation of Bacteriochlorins: Effects of the Fused Imide vs Isocyclic Ring in Photophysical and Electrochemical Properties (2008)
  • Author(s): Liu, C., Dobhal, M. P., Ethirajan, M., Missert, J. R., Pandey, R. K., Balasubramanian, S., Sukumaran, D. K., Zhang, M., Kadish, K. M., Ohkubo, K., Fukuzumi, S.
  • Journal Title: J. Am. Chem. Soc. 130 Pages: 14311-14323
• [Journal Article] A Discrete Supramolecular Conglomerate Composed of Two Saddle-Distorted Zinc(II)-Phthalocyanine Complexes and a Doubly Protonated Porphyrin with Saddle-Distortion Undergoing Efficient Photoinduced Electron Transfer (2008)
  • Author(s): Kojima, T., Honda, T., Ohkubo, K., Shiro, M., Kusukawa, T., Fukuda, T., Kobayashi, N., Fukuzumi, S.
  • Journal Title: Angew. Chem., Int. Ed. 47 Pages: 6712-6716
• [Journal Article] Androgynous Porphyrins. Silver(II) Quinoxalinoporphyrins Act as Both Good Electron Donors and Acceptors (2008)
  • Author(s): Fukuzumi, S., Ohkubo, K., Zhu, W., Sintic, M., Khoury, T., Sintic, P. J., E, W., Ou, Z., Crossley, M. J., Kadish, K. M.
  • Journal Title: J. Am. Chem. Soc. 130 Pages: 9451-9458
• [Journal Article] Face-to-Face Held Pacman Type Porphyrin-Fullerene Dyads : Design, Synthesis, Charge Transfer Interactions and Photophysical Studies (2008)
  • Author(s): D'Souza, F., Maligaspe, E., Karr, P. A., Schumacher, A. L., Ojaimi, M. E., Gros, C. P., Barbe, J.-M., Ohkubo, K., Fukuzumi, S.
  • Journal Title: hem. Eur. J. 14 Pages: 674-681
• [Journal Article] Constracting Photodynamics between Dithiapyrene-C60 and Pyrene-C60 Dyads (2008)
  • Author(s): Guldi, D. M., Spaning, F., Kreher, D., Perepichka, I. F., Bryce, M. R., Ohkubo, K., Fukuzumi, S.
  • Journal Title: Chem. Eur. J. 14 Pages: 250-258
• [Journal Article] Spectroscopic Characterization of Photolytically Generated Radical Ion Pairs in Single-Wall Carbon Nanotubes Bearing Surface-Immobilized Tetrathiafulvalens (2008)
  • Author(s): Herranz, M. A., Ehli, C., Campidelli, S., Gutierrez, M., Hug, G. L., Ohkubo, K., Fukuzumi, S., Prato, M., Matin, N., Guldi, D. M.
  • Journal Title: J. Am. Chem. Soc. 130 Pages: 66-73
• [Journal Article] Design and Synthesis of Polymetallic Complexes Based on meso-Calix[4]pyrrole : Platform for Multielectron Chemistry (2007)
  • Author(s): Custa, L., Gross, D., Lynch, V. M., Ou, Z., Kajokiiya, W., Ohkubo, K., Fukuzumi, S., Kadish, K. M., J. L. Sessler
  • Journal Title: J. Am. Chem. Soc. 129 Pages: 11696-11697
• [Journal Article] Selective Inclusion of Electron-Donating Molecules into Porphyrin Nanochannels Derived from Self-Assembly of Saddle-Distorted Dicationic Porphyrins and Photoinduced Electron Transfer from the Guest Molecules to the Porphyrin Dications (2007)
  • Author(s): Kojima, T., Nakanishi, T., Harada, R., Ohkubo, K., Yamauchi, S., Fukuzumi, S.
  • Journal Title: Chem. Eur. J. 36 Pages: 8714-8725
• [Journal Article] Synthesis and Characterization of Mononuclear Ruthenium(III)-Pyridylamine Complexes and Mechanistic Insights into Their Catalytic Alkene Functionalization with m-Chloroperbenzoic Acid (2007)
  • Author(s): Kojima, T., Hayashi, K., Iizuka, S., Tani, F., Naruta, Y., Kawano, M., Ohashi, Y., Hirai, Y., Ohkubo, K., Fukuzumi, S.
  • Journal Title: Chem. Eur. J. 13 Pages: 8212-8222
• [Journal Article] Intramolecular Electron Transfer within the Substituted Tetrathiafulvalene-Quinone Dyads : FAcilitated by Metal Ion and Photomodulation in the Presence of Spiropyran (2007)
  • Author(s): Wu, H., Zhang, D., Su, L., Ohkubo, K., Zhang, C., Yin, S., Mao, L., Shuai, Z., Fukuzumi, S., Zhu, D.
  • Journal Title: J. Am. Chem. Soc. 129 Pages: 6839-6846
• [Journal Article] Modulation of Characteristics of a Ruthenium-Coordinated Flavin Analog Showing an Unprecedented Coordination Mode (2007)
  • Author(s): Miyazaki, S., Ohkubo, K., Kojima, T., Fukuzumi, S.
  • Journal Title: Angew. Chem. Int. Ed. 46 Pages: 905-908
• [Presentation] Rational Design of Long-Lived Charge Separation (2008)
  • Author(s): Kei Ohkubo
  • Organizer: Osaka University Forum 2008
  • Place of Presentation: Milton Marks Conference Center "Auditorium" San Francisco, USA
  • Year and Date: 20081208-10
• [Presentation] A Discrete Supramolecular Conglomerate Composed of Saddle-Distorted Porphyrin Dication and Zn(II)-Phthalocyanine Complexes (2008)
  • Author(s): Tatsuhiko Honda, Takahiko Kojima, Kei Ohkubo, Motoo Shiro, Takahiro Kusukawa, Takamitsu Fukuda, Nagao Kobayashi, Shunichi Fukuzumi
  • Organizer: The 4^<th> Asian Biological Inorganic Chemistry Conference(AsBIC IV)
  • Place of Presentation: Jeju, Korea
  • Year and Date: 20081110-13
• [Presentation] Homogeneous and Heterogeneoues Catalytic Reduction of Dioxygen Using Cobalt Corroles (2008)
  • Author(s): Kei Ohkubo, Jing Shen, Claude P. Gros, Jean-Michel Barbe, Karl M. Kadish, Roger Guilard, Shunichi Fukuzumi
  • Organizer: The 4th Asian Biological Inorganic Chemistry Conference (AsBIC IV)
  • Place of Presentation: Jeju, Korea
  • Year and Date: 20081110-13
• [Presentation] Elongation of Charge-Separation Lifetime of Zinc Quinoxalino- porphyrin-Gold Quinoxalinoporphyrin by Binding of Scandium Ion (2008)
  • Author(s): Kei Ohkubo, Rachel Garcia, Paul J. Sintic, Tony Khoury, Maxwell J. Crossley, Karl M. Kadish, Houston),Shunichi Fukuzumi
  • Organizer: The 5^<th> Asian-Oceanian Photochemistry Conference
  • Place of Presentation: Beijing, China
  • Year and Date: 20081101-05
• [Presentation] Effects of Magnesium Ion on Photoinduced Electron Transfer in Zinc Phthalocyanine-Perylenebisimide Dyad and Triad (2008)
  • Author(s): Kei Ohkubo, Fernando Fenandez-Lazaro, Angela Sastre-Santos, Shunichi Fukuzumi
  • Organizer: 2008 Korea-Japan Symposium on Frontier Photoscience (KJFP 2008)
  • Place of Presentation: Jeju, Korea
  • Year and Date: 20080925-28
• [Presentation] Formation of the Charge-Separated State in N,N-Dimethylaniline-Flavin Dyad with Millisecond Lifetime in Solution at Room Temperature (2008)
  • Author(s): Motonobu Murakami, Kei Ohkubo, Shunichi Fukuzumi
  • Organizer: 2008 Korea-Japan Symposium on Frontier Photoscience (KJFP 2008)
  • Place of Presentation: Jeju, Korea
  • Year and Date: 20080925-28
• [Presentation] Closely Linked Electron Donor-Acceptor Dyads with Much Longer Charge-Separation Lifetimes than Natural Photosynthetic Reaction Center (2008)
  • Author(s): Kei Ohkubo
  • Organizer: 5th International Conference on Porphyrins and Phthalocyanines (ICPP-5)
  • Place of Presentation: Moscow, Russia
  • Year and Date: 20080707-11
• [Presentation] Photodynamics of Supramolecule Composed of Saddle-Distorted Protonated Porphyrin and Zn-Phthalocyanine (2008)
  • Author(s): Tatsuhiko Honda, Takahiko Kojima, Tatsuaki Nakanishi, Takamitsu Fukuda, Nagao Kobayashi, Kei Ohkubo, Shunichi Fukuzumi
  • Organizer: 5th International Conference on Porphyrins and Phthalocyanines (ICPP-5)
  • Place of Presentation: Moscow, Russia
  • Year and Date: 20080707-11
• [Presentation] A Supramolecular Assembly Composed of Saddle-Distorted Protonated Porphyrin and Zn-Phthalocyanine (2008)
  • Author(s): Takahiko Kojima, Tatsuhiko Honda, Tatsuaki Nakanishi, Kei Ohkubo, Takamitsu Fukuda, Nagao Kobayashi, and Shunichi Fukuzumi
  • Organizer: 5th International Conference on Porphyrins and Phthalocyanines (ICPP-5)
  • Place of Presentation: Moscow, Russia
  • Year and Date: 20080707-11
• [Presentation] Photoinduced Charge Separation of Electron Donor-Substituted Flavin and Supramolecular Formation with Fullerene Receptor by Hydrogen Bonding (2008)
  • Author(s): Motonobu Murakami, Kei Ohkubo, Vito Sgobba, Dirk M. Guldi, Florian Wessendorf, Andreas Hirsch, Shunichi Fukuzumi
  • Organizer: 213th ECS Meeting
  • Place of Presentation: Phoenix, Arizona, USA
  • Year and Date: 20080518-22
• [Presentation] A Supramolecular Complex between an Electron Donor-Substituted Flavin and Fullerene with Receptors by Hydrogen Bonding (2008)
  • Author(s): Motonobu Murakami, Kei Ohkubo, Vito Sgobba, Dirk M. Guldi, Florian Wessendorf, Andreas Hirsch, and Shunichi Fukuzumi
  • Organizer: The 1st International Global COE Symposium on Bio-Environmental Chemistry (GCOEBEC-1)
  • Year and Date: 20080127-29
• [Presentation] Free Radical-Scavenging Reactions by Neurotransmitters (2008)
  • Author(s): Tomonori Kawashima, Kei Ohkubo, Yoshihiko Moro-oka, Shunichi Fukuzumi
  • Organizer: The 1st International Global COE Symposium on Bio-Environmental Chemistry (GCOEBEC-1)
  • Year and Date: 20080127-29
• [Presentation] Dynamics in Photoinduced Electron-Transfer Reduction of Diprotonated Porphyrins with Conformational Distortion (2008)
  • Author(s): Tatsuaki Nakanishi, Kei Ohkubo, Takahiko Kojima, Shunichi Fukuzumi
  • Organizer: The 1st International Global COE Symposium on Bio-Environmental Chemistry (GCOEBEC-1)
  • Place of Presentation: 吹田
  • Year and Date: 20080127-29
• [Presentation] Photophysical And Electrochemical Properties of Metallobacteriochlorins for Photodynamic Therapy (2007)
  • Author(s): Kei Ohkubo, Xiang Zheng, Yihui Chen, Ravindra K. Pandey, Riqiang Zhan, Karl M. Kadish, Shunichi Fukuzumi
  • Organizer: 211th ECS Meeting
  • Place of Presentation: Chicago, Illinois, USA
  • Year and Date: 20070506-11
• [Presentation] Electron-Transfer Properties of Substituted Bi-, Ter-, and Quaterpyrroles (2007)
  • Author(s): Wenbo E, Kei Ohkubo, David Sanchez-Garcia, Elizabeth Karnas, Min Zhang, Jonathan L. Sessler, Shunichi Fukuzumi, Karl M. Kadisha
  • Organizer: 211th ECS Meeting
  • Place of Presentation: Chicago, Illinois, USA
  • Year and Date: 20070506-11
• [Presentation] Photoinduced Electron Transfer IN Silicon Phthalocyanines Functionalized with C_<60> (2007)
  • Author(s): Angela Sastre-Santos, Luis Martin-Gomis, Maria Pascual del Riquelme, Fernando Fernandez-Lazaro, Kei Ohkubo, Shunichi Fukuzumi
  • Organizer: 211th ECS Meeting
  • Place of Presentation: Chicago, Illinois, USA
  • Year and Date: 20070506-11
• [Presentation] 天然を凌駕する電荷分離寿命を有するドナー・アクセプター連結分子を用いた光触媒反応 (2007)
  • Author(s): Kei Ohkubo
  • Organizer: 新物質創製研究アスペクト研究交流会
  • Place of Presentation: 筑波大学
  • Year and Date: 2007-10-06
• [Presentation] 長寿命の光電荷分離状態を有するドナー・アクセプター連結系分子の開発と応用 (2007)
  • Author(s): Kei Ohkubo
  • Organizer: 第1回デバイス物性研究会
  • Place of Presentation: 大阪大学
  • Year and Date: 2007-04-13
• [Patent(Industrial Property Rights)] キノリニウムイオン誘導体、キノリニウムイオン誘導体の製造方法、キノリニウムイオン誘導体を用いた製品、キノリニウムイオン誘導体を用いた還元方法および酸化方法 (2009)
  • Inventor(s): 福住俊一, 小谷弘明, 大久保敬
  • Industrial Property Rights Holder: 大阪大学
  • Industrial Property Number: 特願2009-533049
  • Filing Date: 2009-03-10
• [Patent(Industrial Property Rights)] 新規9-置換アクリジニウム誘導体、および9-置換アクリジニウム誘導体を用いた芳香族アルデヒドと過酸化水素の同時製造方法 (2008)
  • Inventor(s): 大久保敬, 福住俊一, 岩田亮介, 水島健太郎, 鈴木信夫, 相馬和憲
  • Industrial Property Rights Holder: 東京化成工業株式会社
  • Industrial Property Number: 特願2008-255128
  • Filing Date: 2008-09-03
• [Patent(Industrial Property Rights)] 水素発生触媒 (2007)
  • Inventor(s): 福住俊一, 小谷弘明, 大久保敬, 花崎亮
  • Industrial Property Rights Holder: JST
  • Industrial Property Number: 特願2007-247656
  • Filing Date: 2007-09-25