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2013 Fiscal Year Final Research Report

Development of porphyrin photosensitizer for photodynamic therapy

Research Project

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Project/Area Number 23750186
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Chemistry related to living body
Research InstitutionShizuoka University

Principal Investigator

HIRAKAWA Kazutaka  静岡大学, 工学(系)研究科(研究院), 准教授 (60324513)

Project Period (FY) 2011 – 2013
Keywords光線力学的療法 / 光増感剤 / ポルフィリン / 電子移動 / 一重項酸素 / タンパク質損傷 / トリプトファン / 酸化反応
Research Abstract

The purpose of this study is the development of novel photosensitizer for photodynamic therapy (PDT), which is a less invasive treatment of cancer. In general, porphyins were used as the PDT photosensitizer. Administered porphyrins can generate singlet oxygen to photosensitize biomolecules oxidation. However, since the oxygen concentration is relatively low in tumor, the PDT effect in tumor is restricted. In this study, P(V)porphyrins were used as photosensitizers. P(V)porphyrins induced the oxidation of amino acid residue in a water soluble protein, a target model biomolecule, during visible-light irradiation. It was confirmed that the mechanism of protein photodamage by these porphyrins is singlet oxygen generation and photo-induced electron transfer. For this experiment, the novel analysis method to detect the protein damage was developed. Further, the novel porphyrin photosensitizers were synthesized and their activities were demonstrated.

  • Research Products

    (46 results)

All 2014 2013 2012 2011 Other

All Journal Article (10 results) (of which Peer Reviewed: 10 results) Presentation (30 results) Book (5 results) Remarks (1 results)

  • [Journal Article] Nile blue can photosensitize DNA damage through electron transfer2014

    • Author(s)
      Kazutaka Hirakawa, Kazuhiro Ota, Junya Hirayama, Shinji Oikawa, Shosuke Kawanishi
    • Journal Title

      Chemical Research in Toxicology

      Volume: Vol.27 Pages: 649-655

    • Peer Reviewed
  • [Journal Article] Singlet oxygen generating activity of an electron donor-connecting porphyrin photosensitizer can be controlled by DNA2013

    • Author(s)
      Kazutaka Hirakawa, Yoshinobu Nishimura, Tatsuo Arai, Shigetoshi Okazaki
    • Journal Title

      The Journal of Physical Chemistry B

      Volume: Vol.117 Pages: 13490-13496

    • Peer Reviewed
  • [Journal Article] Examination of protein-damaging activity of phosphorus(V)porphyrin photosensitizer for photodynamic therapy2013

    • Author(s)
      Kazutaka Hirakawa, Taiki Yamanaka, Jin Matsumoto, Masahide Yasuda
    • Journal Title

      Journal of Analytical and Bioanalytical Techniques

    • DOI

      10.4172/2155-9872.S1-003

    • Peer Reviewed
  • [Journal Article] Photosensitized protein damage by dimethoxyphosphorus(V) tetraphenylporphyrin2013

    • Author(s)
      Kazutaka Hirakawa, Norihito Fukunaga, Yoshinobu Nishimura, Tatsuo Arai, Shigetoshi Okazaki
    • Journal Title

      Bioorganic & Medicinal Chemistry Letters

      Volume: Vol.23 Pages: 2704-2707

    • Peer Reviewed
  • [Journal Article] Photosensitized damage of protein by fluorinated diethoxyphosphorus(V)porphyrin2013

    • Author(s)
      Kazutaka Hirakawa, Keito Azumi, Yoshinobu Nishimura, Tatsuo Arai, Yoshio Nosaka, Shigetoshi Okazaki
    • Journal Title

      Journal of Porphyrins and Phthalocyanines

      Volume: Vol.17 Pages: 56-62

    • Peer Reviewed
  • [Journal Article] Controlled generation of singlet oxygen by water-soluble meso-pyrenylporphyrin photosensitizer under interaction with DNA2012

    • Author(s)
      Kazutaka Hirakawa, Mari Harada, Shigetoshi Okazaki, Yoshio Nosaka
    • Journal Title

      Chemical Communications

      Volume: Vol.48 Pages: 4770-4772

    • Peer Reviewed
  • [Journal Article] Dynamics of singlet oxygen generation by DNA-binding photosensitizers2012

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

      The Journal of Physical Chemistry B

      Volume: Vol.116 Pages: 3037-3044

    • Peer Reviewed
  • [Journal Article] Analysis of protein damage based on the fluorometry of tryptophan residue2012

    • Author(s)
      Kazutaka Hirakawa, Shiori Inoue
    • Journal Title

      Current Topics in Analytical Chemistry

      Volume: Vol.9 Pages: 57-62

    • Peer Reviewed
  • [Journal Article] Oxygen-independent DNA damage photosensitized by rhodamine-6G2011

    • Author(s)
      Kazutaka Hirakawa, Satoru Ochiai, Shinji Oikawa, Shosuke Kawanishi
    • Journal Title

      Trends in Photochemistry and Photobiology

      Volume: Vol.13 Pages: 29-35

    • Peer Reviewed
  • [Journal Article] Control of singlet oxygen generation photosensitized by meso-anthrylporphyrin through interaction with DNA2011

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

      Photochemistry and Photobiology

      Volume: Vol.87 Pages: 833-839

    • Peer Reviewed
  • [Presentation] ナイルブルーの光増感反応によるグアニン連続配列特異的DNA損傷2014

    • Author(s)
      平川和貴,大田和洋,平山淳也,及川伸二,川西正祐
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋
    • Year and Date
      2014-03-30
  • [Presentation] Photosensitized damage of DNA and protein2014

    • Author(s)
      Kazutaka Hirakawa
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋
    • Year and Date
      2014-03-29
  • [Presentation] Oxidative damage of amino acid residue of protein photosensitized by P(V)porphyrins through electron transfer and singlet oxygen generation2014

    • Author(s)
      欧陽東彦,平川和貴
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋
    • Year and Date
      2014-03-28
  • [Presentation] Evaluation of photosensitized protein damage by phosphorus(V)porphyrin2013

    • Author(s)
      Kazutaka Hirakawa, Yoshinobu Nishimura, Tatsuo Arai, Shigetoshi Okazaki
    • Organizer
      The 9th Korea-Japan Symposium on Frontier Photoscience-2013
    • Place of Presentation
      ソウル
    • Year and Date
      2013-11-27
  • [Presentation] Photosensitized singlet oxygen generation can be controlled by DNA microenvironment2013

    • Author(s)
      Kazutaka Hirakawa, Mari Harada, Yoshinobu Nishimura, Tatsuo Arai, Yoshio Nosaka, Shigetoshi Okazaki, Toru Hirano
    • Organizer
      The 6th Asia & Oceania Conference on Photobiology
    • Place of Presentation
      シドニー
    • Year and Date
      2013-11-13
  • [Presentation] DNA認識で一重項酸素生成活性を制御可能なポルフィリン光増感剤2013

    • Author(s)
      平川和貴,西村賢宣,新井達郎,岡崎茂俊
    • Organizer
      第44回中部化学関係学協会支部連合秋季大会
    • Place of Presentation
      浜松
    • Year and Date
      2013-11-02
  • [Presentation] Activity control of singlet oxygen generation by porphyrin photosensitizers for photodynamic therapy through interaction with DNA2013

    • Author(s)
      Kazutaka Hirakawa, Mari Harada, Yoshinobu Nishimura, Tatsuo Arai, Yoshio Nosaka, Shigetoshi Okazaki
    • Organizer
      The 6th International Conference on Health and Longevity Sciences
    • Place of Presentation
      静岡
    • Year and Date
      2013-11-01
  • [Presentation] Fundamental study of photodynamic therapy : Synthesis of P(V)tetranaphthylporphyrin derivatives and their activity as photosensitizer2013

    • Author(s)
      Shunsuke Aoki, Norihito Fukunaga, Hiroyuki Ueda, Shigetoshi Okazaki, Kazutaka Hirakawa
    • Organizer
      The 6th International Conference on Health and Longevity Sciences
    • Place of Presentation
      静岡
    • Year and Date
      2013-11-01
  • [Presentation] DNA認識で制御されるアントラセン直結ポルフィリン光増感剤の一重項酸素生成活性2013

    • Author(s)
      平川和貴,西村賢宣,新井達郎,岡崎茂俊
    • Organizer
      2013年光化学討論会
    • Place of Presentation
      愛媛
    • Year and Date
      2013-09-11
  • [Presentation] 水溶性長鎖アルコキシP(V)ポルフィリンによるタンパク質損傷とカタラーゼ活性の阻害2013

    • Author(s)
      平川和貴,山中泰樹,松本仁,保田昌秀
    • Organizer
      2013年光化学討論会
    • Place of Presentation
      愛媛
    • Year and Date
      2013-09-11
  • [Presentation] P(V)テトラナフチルポルフィリンの合成とタンパク質光損傷活性の評価2013

    • Author(s)
      青木俊輔,植田裕之,岡崎茂俊,平川和貴
    • Organizer
      2013年光化学討論会
    • Place of Presentation
      愛媛
    • Year and Date
      2013-09-11
  • [Presentation] Photosensitized protein damage by using three kinds of porphyrin complexes with different redox potential2013

    • Author(s)
      欧陽東彦,井上思織,岡崎茂俊,平川和貴
    • Organizer
      2013年光化学討論会
    • Place of Presentation
      愛媛
    • Year and Date
      2013-09-11
  • [Presentation] 長鎖アルコキシ基をもつ水溶性P(V)ポルフィリンによるタンパク質損傷 : 酵素活性阻害効果2013

    • Author(s)
      平川和貴,山中泰樹,岡崎茂俊,松本仁,保田昌秀
    • Organizer
      第35回日本光医学・光生物学会
    • Place of Presentation
      浜松
    • Year and Date
      2013-07-13
  • [Presentation] DNA認識で発現する水溶性meso-アントリルポルフィリンの光化学的一重項酸素生成活性2013

    • Author(s)
      平川和貴,岡崎茂俊
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      草津
    • Year and Date
      2013-03-23
  • [Presentation] メソ-フェナントリルポルフィリンの合成と光化学的物性評価2013

    • Author(s)
      井藤裕輔,平川和貴
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      草津
    • Year and Date
      2013-03-22
  • [Presentation] Control of singlet oxygen generating activity of meso-pyrenylporphyrin through interaction with DNA2012

    • Author(s)
      Kazutaka Hirakawa, Mari Harada, Shigetoshi Okazaki, Yoshinobu Nishimura, Tatsuo. Arai, Yoshio Nosaka
    • Organizer
      7th Asian Photochemistry Conference 2012 (APC2012)
    • Place of Presentation
      吹田
    • Year and Date
      2012-11-13
  • [Presentation] Protein Photodamage by the S_2 Excited State of Porphyrin Zinc Complex2012

    • Author(s)
      Shiori Inoue, Kazutaka Hirakawa
    • Organizer
      7th Asian Photochemistry Conference 2012 (APC2012)
    • Place of Presentation
      吹田
    • Year and Date
      2012-11-13
  • [Presentation] 電子ドナー直結ポルフィリンの電子遷移とDNA認識による一重項酸素生成制御2012

    • Author(s)
      平川和貴,原田万理,岡崎茂俊,野坂芳雄
    • Organizer
      2012年光化学討論会
    • Place of Presentation
      東京
    • Year and Date
      2012-09-14
  • [Presentation] ジメトキシP(V)テトラフェニルポルフィリンの光増感作用とタンパク質損傷2012

    • Author(s)
      平川和貴,福永法仁,岡崎茂俊
    • Organizer
      2012年光化学討論会
    • Place of Presentation
      東京
    • Year and Date
      2012-09-14
  • [Presentation] 医学応用を指向した光増感反応の研究2012

    • Author(s)
      平川和貴
    • Organizer
      第17回日本光生物学協会年会
    • Place of Presentation
      吹田
    • Year and Date
      2012-08-18
  • [Presentation] DNA認識で発現する水溶性ポルフィリン光増感剤の一重項酸素生成活性2012

    • Author(s)
      平川和貴,原田万理,岡崎茂俊
    • Organizer
      第34回日本光医学・光生物学会
    • Place of Presentation
      神戸
    • Year and Date
      2012-07-28
  • [Presentation] Type I光増感剤ジメトキシP(V)テトラフェニルポルフィリン2012

    • Author(s)
      平川和貴,福永法仁,岡崎茂俊
    • Organizer
      第22回日本光線力学学会学術講演会
    • Place of Presentation
      つくば
    • Year and Date
      2012-07-07
  • [Presentation] DNA-damaging activity of cationic porphyrinoid photosensitizers and 5-ALA-derived protoporphyrin IX2012

    • Author(s)
      Kazutaka Hirakawa
    • Organizer
      Seventh International Conference on Porphyrins and Phthalocyanines (ICPP-7)
    • Place of Presentation
      済州島
    • Year and Date
      2012-07-03
  • [Presentation] ポルフィリン光増感剤によるタンパク質損傷 : Type IおよびType II機構の寄与2012

    • Author(s)
      平川和貴,岡崎茂俊
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      横浜
    • Year and Date
      2012-03-26
  • [Presentation] Determination of type I and type II mechanisms for photosensitized protein damage by porphyrin phosphorus(V) complex2011

    • Author(s)
      Kazutaka Hirakawa, Shigetoshi Okazaki, Yoshinobu Nishimura, Tatsuo Arai, Hiroshi Segawa
    • Organizer
      The 8th Korea-Japan Symposium on Frontier Photoscience-2011
    • Place of Presentation
      ソウル
    • Year and Date
      2011-10-30
  • [Presentation] Photooxidative damage of tryptophan by porphyrin P(V) complex2011

    • Author(s)
      Hiroki Yamaguchi, Kazutaka Hirakawa
    • Organizer
      The 4th International Conference on Health and Longevity Sciences (ICHALS)
    • Place of Presentation
      静岡
    • Year and Date
      2011-10-21
  • [Presentation] Photosensitized damage of biomolecules by water-soluble porphyrin2011

    • Author(s)
      Shiori Inoue, Kazutaka Hirakawa
    • Organizer
      The 4th International Conference on Health and Longevity Sciences (ICHALS)
    • Place of Presentation
      静岡
    • Year and Date
      2011-10-21
  • [Presentation] 水溶性ポルフィリンによる生体分子の光酸化損傷2011

    • Author(s)
      井上思織,平川和貴
    • Organizer
      第5回バイオ関連化学シンポジウム
    • Place of Presentation
      つくば
    • Year and Date
      2011-09-12
  • [Presentation] 長鎖アルキル基をもつ水溶性ポルフィリンP(V)錯体によるタンパク質の光損傷2011

    • Author(s)
      山中泰樹,松本仁,保田昌秀,岡崎茂俊,平川和貴
    • Organizer
      第5回バイオ関連化学シンポジウム
    • Place of Presentation
      つくば
    • Year and Date
      2011-09-12
  • [Presentation] Photo-oxidation of human serum albumin by the singlet excited state of water-soluble P(V)porphyrin2011

    • Author(s)
      Kazutaka Hirakawa, Hiroki Yamaguchi, Hironubu Umemoto, Shigetoshi Okazaki, Yoshinobu Nishimura, Tatsuo Arai, Hiroshi Segawa
    • Organizer
      2011年光化学討論会
    • Place of Presentation
      宮崎
    • Year and Date
      2011-09-06
  • [Book] Photo-energy and electron donating ability of pyrene, in Pyrene : Chemical Properties, Biochemistry Applications and Toxic Effects2013

    • Author(s)
      Kazutaka Hirakawa
    • Total Pages
      209 (141-166)
    • Publisher
      Nova Science Publishers
  • [Book] Phosphorus(V)porphyrin : Its Potential Application for Photomedicine, in Handbook of Porphyrins : Chemistry, Properties and Applications2012

    • Author(s)
      Kazutaka Hirakawa
    • Total Pages
      438 (393-408)
    • Publisher
      Nova Science Publishers
  • [Book] Protein oxidation through oxygen-independent mechanism by P(V)porphyrin photosensitizer, in In hope of going over the present Clinical PD and PDT2011

    • Author(s)
      Kazutaka Hirakawa, Hiroshi Segawa, Toru Hirano, Shigetoshi Okazaki, Yoshio Nosaka
    • Total Pages
      248 (40-50)
    • Publisher
      三惠社
  • [Book] Development of DNA selective porphyrinoid photosensitizer, in In hope of going over the present Clinical PD and PDT2011

    • Author(s)
      Kazutaka Hirakawa, and Toru Hirano
    • Total Pages
      248 (51-52)
    • Publisher
      三惠社
  • [Book] Deuterium effect on the photosensitized biomolecules damage via singlet oxygen generation, in Advances in chemistry research. Vol. 102011

    • Author(s)
      Kazutaka Hirakawa
    • Total Pages
      510 (429-437)
    • Publisher
      Nova Science Publishers
  • [Remarks]

    • URL

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

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Published: 2015-06-25  

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