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Activity Control of Photosensitizers for Photodynamic Therapy through DNA Recognition

Research Project

Project/Area Number 20750131
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeSingle-year Grants
Research Field Chemistry related to living body
Research InstitutionShizuoka University

Principal Investigator

HIRAKAWA Kazutaka  Shizuoka University, 工学部, 准教授 (60324513)

Project Period (FY) 2008 – 2009
Project Status Completed (Fiscal Year 2009)
Budget Amount *help
¥3,510,000 (Direct Cost: ¥2,700,000、Indirect Cost: ¥810,000)
Fiscal Year 2009: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2008: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
KeywordsDNA / 光増感剤 / 一重項酸素 / 光線力学的療法 / 電子移動 / ポルフィリン / エネルギー移動 / がん治療 / アルカロイド
Research Abstract

The purpose of this study is the activity control of photosensitizers for photodynamic therapy, which is a promising treatment of cancer and some non-malignant conditions. Berberine and palmatine can photosensitize the generation of singlet oxygen only when these photosensitizers bind to DNA. This study revealed the sequence specificity on the activity control of these photosensitizers, suggesting the possibility of design of sequence-specific photosensitizer. To apply this control mechanism for clinical using porphyrinoid photosensitizer, the electron donor connecting porphyrins were synthesized. The photoexcited states of these porphyrins were quenched via intramolecular electron transfer. The interaction with DNA inhibited the electron transfer quenching of these photoexcited porphyrins, leading to the singlet oxygen generation via photoenergy transfer to molecular oxygen. These findings demonstrated that the DNA-selective photosensitizers can be developed using electron donor connecting porphyrins.

Report

(3 results)
  • 2009 Annual Research Report   Final Research Report ( PDF )
  • 2008 Annual Research Report
  • Research Products

    (53 results)

All 2010 2009 2008 Other

All Journal Article (17 results) (of which Peer Reviewed: 12 results) Presentation (28 results) Book (3 results) Remarks (3 results) Patent(Industrial Property Rights) (2 results)

  • [Journal Article] Acid Dissociation of Axial Hydroxyl Group of Hydroxy(1-pyrenebutoxy)-phosphorus(V) Porphyrin Controls the Intramolecular Excitation Energy Transfer2010

    • Author(s)
      Kazutaka Hirakawa, Hiroshi Segawa
    • Journal Title

      Photochemical and Photobiological Sciences Vol.9

      Pages: 704-709

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Anomalously Selective Quenching of S2 Fluorescence from Upper Excited State of Zinc 5-(1'-pyrenyl)-10, 15, 20-triphenylporphyrin Derivatives through Intramolecular Charge Transfer State2009

    • Author(s)
      Kazutaka Hirakawa, Keiko Saito, Hiroshi Segawa
    • Journal Title

      The Journal of Physical Chemistry A Vol.113

      Pages: 8852-8856

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Platinum Nanoparticle Catalyst Scavenges Hydrogen Peroxide Generated from Hydroquinone2009

    • Author(s)
      Kazutaka Hirakawa, Shoichiro Sano
    • Journal Title

      Bulletin of the Chemical Society of Japan Vol.82

      Pages: 1299-1303

    • NAID

      10025864839

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Fluorometry of Singlet Oxygen Generated via a Photosensitized Reaction Using Folic Acid and Methotrexate2009

    • Author(s)
      Kazutaka Hirakawa
    • Journal Title

      Analytical and Bioanalytical Chemistry Vol.393

      Pages: 999-1005

    • NAID

      120001794387

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] ポルフィリンP(V)錯体による光誘起電子移動および一重項酸素生成を介するヒト血清アルブミンの光損傷2009

    • Author(s)
      平川和貴, 江原由美子, 平野達, 瀬川浩司
    • Journal Title

      日本レーザー医学会誌 Vo.29,No.4

      Pages: 376-382

    • NAID

      130004492014

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] DNA Damage and Apoptosis Induced by Photosensitization of 5, 10, 15, 20-Tetrakis (N-methyl-4-pyridyl)-21H, 23H-porphyrin via Singlet Oxygen Generation2009

    • Author(s)
      Saeko Tada-Oikawa, Shinji Oikawa, Junya Hirayama, Kazutaka Hirakawa, Shosuke Kawanishi
    • Journal Title

      Photochemistry and Photobiology Vol.85

      Pages: 1391-1399

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Singlet Oxygen Generation from the Photosensitized Reaction in DNA Microenvironment2009

    • Author(s)
      Kazutaka Hirakawa, Yoshio Nosaka, Toru Hirano, Yoshinobu Nishimura, Tatsuo Arai
    • Journal Title

      Photomedicine and Photobiology Vol.31

      Pages: 7-8

    • Related Report
      2009 Final Research Report
  • [Journal Article] Evaluation and Chemoprevention of Phototoxic Effect by the Novel Materials2009

    • Author(s)
      Kazutaka Hirakawa
    • Journal Title

      Photomedicine and Photobiology Vol.31

      Pages: 33-34

    • Related Report
      2009 Final Research Report
  • [Journal Article] Anomalously selective quenching of S_2 fluorescence from upper excited state of zinc 5-(1'-pyrenyl)-10, 15, 20-triphenylporphyrin derivatives through intramoleculaz chazge transfer state2009

    • Author(s)
      Kazutaka Hirakawa, Keiko Saito, Hiroshi Segawa
    • Journal Title

      The Journal of Physical Chemistry A 113

      Pages: 8852-8856

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Platinum nanoparticle catalyst scavenges hydrogen peroxide generated from hydroquinone2009

    • Author(s)
      Kazutaka Hirakawa, Shoichiro Sano
    • Journal Title

      Bulletin of the Chemical Society of Janan 82

      Pages: 1299-1303

    • NAID

      10025864839

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Singlet oxygen generation from the photosensitized reaction in DNA micr oenvironment2009

    • Author(s)
      Kazutaka Hirakawa, Yoshio Nosaka, Toru Hirano, Yoshinobu Nishimura, Tatsuo Arai
    • Journal Title

      Photomedicine and Photobiology 31

      Pages: 7-8

    • Related Report
      2009 Annual Research Report
  • [Journal Article] Fluorometry of Singlet Oxygen Generated via a Photosensitized Reaction Using Folic Acid and Methotrexate2009

    • Author(s)
      Kazutaka Hirakawa
    • Journal Title

      Analytical and Bioanalytical Chemistry 393

      Pages: 999-1005

    • NAID

      120001794387

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] ポルフィリンP(V)錯体による光誘起電子移動および一重項酸素生成を介するヒト血清アルブミンの光損傷2009

    • Author(s)
      平川和貴, 江原由美子, 平野達, 瀬川浩司
    • Journal Title

      日本レーザー医学会誌 29

      Pages: 376-382

    • NAID

      130004492014

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Preventive Action of Metal Nanoparticles on UVA-sensitized Oxidation through Hydrogen Peroxide Formation2009

    • Author(s)
      Kazutaka Hirakawa, Kohei Shiota, Shoichiro Sano
    • Journal Title

      Photomedicine and Photobiology 30

      Pages: 27-28

    • Related Report
      2008 Annual Research Report
  • [Journal Article] The Microenvironment of DNA Switches the Activity of Singlet Oxygen Generation Photosensitized by Berberine and Palmatine2008

    • Author(s)
      Kazutaka Hirakawa, Toru Hirano
    • Journal Title

      Photochemistry and Photobiology Vol.84

      Pages: 202-208

    • Related Report
      2009 Final Research Report
    • Peer Reviewed
  • [Journal Article] Preventive Action of Metal Nanoparticles on UVA-sensitized Oxidation through Hydrogen Peroxide Formation2008

    • Author(s)
      Kazutaka Hirakawa, Kohei Shiota, Shoichiro Sano
    • Journal Title

      Photomedicine and Photobiology Vol.30

      Pages: 27-28

    • Related Report
      2009 Final Research Report
  • [Journal Article] The Microenvironment of DNA Switches the Activity of Singlet Oxygen Generation Photosensitized by Berberine and Palmatine2008

    • Author(s)
      Kazutaka Hirakawa, Toru Hirano
    • Journal Title

      Photochemistry and Photobiology 84

      Pages: 202-208

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Presentation] DNA認識による電子ドナー直結型ポルフィリンの電子遷移制御2010

    • Author(s)
      平川和貴
    • Organizer
      日本化学会第90春季年会
    • Related Report
      2009 Annual Research Report 2009 Final Research Report
  • [Presentation] フッ素含有ポルフィリンP(V)錯体による水溶性タンパク質の光損傷2010

    • Author(s)
      安海恵都、平川和貴
    • Organizer
      日本化学会第90春季年会
    • Related Report
      2009 Final Research Report
  • [Presentation] カチオン性青色光増感剤とDNAとの相互作用2010

    • Author(s)
      大田和洋、平川和貴
    • Organizer
      日本化学会第90春季年会
    • Related Report
      2009 Final Research Report
  • [Presentation] ドナー直結ポルフィリンのアニオン性ポリマーによる電子移動制御2010

    • Author(s)
      原田万理、平川和貴
    • Organizer
      日本化学会第90春季年会
    • Related Report
      2009 Final Research Report
  • [Presentation] ポルフィリンP(V)およびZn錯体の水/エタノール混合溶媒における自己会合体形成2010

    • Author(s)
      東野寿樹、花岡淳、平川和貴
    • Organizer
      日本化学会第90春季年会
    • Related Report
      2009 Final Research Report
  • [Presentation] The relaxation process of photoexcited state of DNA-binding photosensitizers and the sequence-dependent generation of singlet oxygeen2009

    • Author(s)
      Kazutaka Hirakawa
    • Organizer
      The 6th Korea-Japan Joint Symposium on Frontier Photoscience
    • Place of Presentation
      Korea University (Deajeon, Korea)
    • Year and Date
      2009-10-31
    • Related Report
      2009 Annual Research Report
  • [Presentation] ジプロピレングリコキシP(V)テトラフェニルポルフィリンによるヒト血清アルブミンの光酸化損傷2009

    • Author(s)
      菊地諒, 平川和貴
    • Organizer
      日本化学会第89春季年会
    • Place of Presentation
      日本大学理工学部船橋キャンパス
    • Year and Date
      2009-03-29
    • Related Report
      2008 Annual Research Report
  • [Presentation] 酵母菌に対する水溶性アンチモンポルフィリンの可視光殺菌効果2009

    • Author(s)
      保田昌秀, 中原卓郎, 松本朋子, 松本仁, 白上努, 平川和貴
    • Organizer
      日本化学会第89春季年会
    • Place of Presentation
      日本大学理工学部船橋キャンパス
    • Year and Date
      2009-03-28
    • Related Report
      2008 Annual Research Report
  • [Presentation] DNA認識による光増感剤の一重項酸素生成活性の制御 : 塩基配列の効果2009

    • Author(s)
      平川和貴, 平野達, 西村賢宣, 新井達郎
    • Organizer
      日本化学会第89春季年会
    • Place of Presentation
      日本大学理工学部船橋キャンパス
    • Year and Date
      2009-03-27
    • Related Report
      2008 Annual Research Report
  • [Presentation] The Relaxation Process of Photoexcited State of DNA-binding Photosensitizers and the Sequence-dependent Generation of Singlet Oxygen2009

    • Author(s)
      Kazutaka Hirakawa, Yoshinobu Nishimura, Tatsuo Arai, Toru Hirano, Yoshio Nosaka
    • Organizer
      The 6th Korea-Japan Joint Symposium on Frontier Photoscience
    • Related Report
      2009 Final Research Report
  • [Presentation] DNA鎖内における光励起状態ベルベリン類の緩和過程2009

    • Author(s)
      平川和貴、西村賢宣、新井達郎、平野達、野坂芳雄
    • Organizer
      2009年光化学討論会
    • Related Report
      2009 Annual Research Report 2009 Final Research Report
  • [Presentation] ビタミンB類を用いた光毒性防護物質の評価2009

    • Author(s)
      平川和貴、山本将太
    • Organizer
      2009年光化学討論会
    • Related Report
      2009 Final Research Report
  • [Presentation] 貴金属ナノ粒子による活性酸素除去に基づく光毒性防護2009

    • Author(s)
      佐野昇一郎、平川和貴
    • Organizer
      2009年光化学討論会
    • Related Report
      2009 Final Research Report
  • [Presentation] 光毒性の評価および化学防護における新規材料の応用2009

    • Author(s)
      平川和貴
    • Organizer
      第31回日本光医学・光生物学会
    • Related Report
      2009 Final Research Report
  • [Presentation] DNA鎖内に結合した光増感剤による一重項酸素生成2009

    • Author(s)
      平川和貴、野坂芳雄、平野達、西村賢宣、新井達郎
    • Organizer
      第31回日本光医学・光生物学会
    • Related Report
      2009 Final Research Report
  • [Presentation] ヒト血清アルブミンとの相互作用下におけるベルベリン類の光増感反応と一重項酸素生成2009

    • Author(s)
      平川和貴、野坂芳雄、平野達
    • Organizer
      第19回日本光線力学学会学術集会
    • Related Report
      2009 Final Research Report
  • [Presentation] DNA認識による光増感剤の一重項酸素生成活性の制御:塩基配列の効果2009

    • Author(s)
      平川和貴、平野達、西村賢宣、新井達郎
    • Organizer
      日本化学会第89春季年会
    • Related Report
      2009 Final Research Report
  • [Presentation] ジプロピレングリコキシp(V)テトラフェニルポルフィリンによるヒト血清アルブミンの光酸化損傷2009

    • Author(s)
      菊地諒、平川和貴
    • Organizer
      日本化学会第89春季年会
    • Related Report
      2009 Final Research Report
  • [Presentation] DNA認識による光化学的一重項酸素生成反応の制御2008

    • Author(s)
      平川和貴, 平野達, 大門利博, 野坂芳雄
    • Organizer
      第41回酸化反応討論会
    • Place of Presentation
      九州大学西新プラザ
    • Year and Date
      2008-11-27
    • Related Report
      2008 Annual Research Report
  • [Presentation] Photochemistry of Folic Acid Analogues : Photosensitized DNA Damage and Application for Fluorometry of Reactive Oxygen Species2008

    • Author(s)
      Kazutaka Hirakawa, Shosuke Kawanish
    • Organizer
      2008 Korea-Japan Symposium on Frontier Photoscience
    • Place of Presentation
      Ramada Plaza Hotel, Jeju
    • Year and Date
      2008-09-26
    • Related Report
      2008 Annual Research Report
  • [Presentation] カチオン性ポルフィリンのベンゾキノン類との複合体形成とS_2およびS_1励起状態からの電子遷移2008

    • Author(s)
      平川和貴, 中島淑
    • Organizer
      2008年光化学討論会
    • Place of Presentation
      大阪府立大学
    • Year and Date
      2008-09-12
    • Related Report
      2008 Annual Research Report
  • [Presentation] 光毒性防御における貴金属ナノ粒子の応用2008

    • Author(s)
      平川和貴, 塩田康平, 佐野昇一郎
    • Organizer
      第30回日本光医学・光生物学会
    • Place of Presentation
      島根県医師会館
    • Year and Date
      2008-07-12
    • Related Report
      2008 Annual Research Report
  • [Presentation] ポルフィリンP(V)錯体による酸素に依存しない光増感反応機構2008

    • Author(s)
      平川和貴, 江原由美子, 平野達, 瀬川浩司
    • Organizer
      第18回日本光線力学学会学術集会
    • Place of Presentation
      テレピアホール(名古屋)
    • Year and Date
      2008-06-14
    • Related Report
      2008 Annual Research Report
  • [Presentation] DNA認識による光化学的一重項酸素生成反応の制御2008

    • Author(s)
      平川和貴、平野達、大門利博、野坂芳雄
    • Organizer
      第41回酸化反応討論会
    • Related Report
      2009 Final Research Report
  • [Presentation] Photochemistry of Folic Acid Analogues: Photosensitized DNA Damage and Application for Fluorometry of Reactive Oxygen Species2008

    • Author(s)
      Kazutaka Hirakawa, Shosuke Kawanish
    • Organizer
      2008 Korea-Japan Symposium on Frontier Photoscience
    • Related Report
      2009 Final Research Report
  • [Presentation] Preventive Action of Metal Nanoparticles on UVA-Sensitized Oxidation through Hydrogen Peroxide Formation2008

    • Author(s)
      Kazutaka Hirakawa, Kohei Shiota, Shoichiro Sano
    • Organizer
      2008 Korea-Japan Symposium on Frontier Photoscience
    • Related Report
      2009 Final Research Report 2008 Annual Research Report
  • [Presentation] 葉酸誘導体の光酸化反応と一重項酸素検出への応用2008

    • Author(s)
      平川和貴
    • Organizer
      2008年光化学討論会
    • Related Report
      2009 Final Research Report 2008 Annual Research Report
  • [Presentation] カチオン性ポルフィリンのベンゾキノン類との複合体形成とS2およびS1励起状態からの電子遷移2008

    • Author(s)
      平川和貴、中島淑
    • Organizer
      2008年光化学討論会
    • Related Report
      2009 Final Research Report
  • [Book] Chemopreventive Action of Organic and Inorganic Materials on Phototoxic Effect(in Photobioogy: Principles, Applications and Effects, Chapter 6)2010

    • Author(s)
      Kazutaka Hirakawa
    • Publisher
      Nova Science Publishers
    • Related Report
      2009 Final Research Report
  • [Book] DNA Damage through Photo-induced Electron Transfer and Photosensitized Generation of Reactive Oxygen Species(in New Research on DNA Damage, Chapter 9)2008

    • Author(s)
      Kazutaka Hirakawa
    • Publisher
      Nova Science Publishers
    • Related Report
      2009 Final Research Report
  • [Book] New Research on DNA Damage2008

    • Author(s)
      Kazutaka Hirakawa
    • Total Pages
      24
    • Publisher
      DNA Damage through Photo-induced Electron Transfer and Photosensitized Generation of Reactive Oxygen Species
    • Related Report
      2008 Annual Research Report
  • [Remarks]

    • URL

      http://www.ipc.shizuoka.ac.jp/~tkhirak/

    • Related Report
      2009 Final Research Report
  • [Remarks]

    • URL

      http://www,ipc.shizuoka,ac.jp/~tkhirak/

    • Related Report
      2009 Annual Research Report
  • [Remarks]

    • URL

      http://www.ipc.shizuoka.ac.jp/~tkhirak/index.html

    • Related Report
      2008 Annual Research Report
  • [Patent(Industrial Property Rights)] 活性酸素の定量法2009

    • Inventor(s)
      平川和貴
    • Industrial Property Rights Holder
      静岡大学
    • Acquisition Date
      2009-01-23
    • Related Report
      2009 Final Research Report
  • [Patent(Industrial Property Rights)] 活性酸素の定量法2009

    • Inventor(s)
      平川和貴
    • Industrial Property Rights Holder
      静岡大学
    • Acquisition Date
      2009-01-23
    • Related Report
      2008 Annual Research Report

URL: 

Published: 2008-04-01   Modified: 2016-04-21  

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