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Design of Environmentally Sensitive Fluorescent Nucleosides and Their Application to Innovative Fluorescence Probe for Gene Analysis

Research Project

Project/Area Number 23350082
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Chemistry related to living body
Research InstitutionNihon University

Principal Investigator

SAITO Isao  日本大学, 工学部, 研究員 (20026082)

Co-Investigator(Kenkyū-buntansha) SAITO Yoshio  日本大学, 工学部, 准教授 (40385985)
庄司 真紀子(田仲真紀子) (庄司 真紀子)  日本大学, 工学部, 研究員 (90397703)
Project Period (FY) 2011-04-01 – 2014-03-31
Project Status Completed (Fiscal Year 2013)
Budget Amount *help
¥19,500,000 (Direct Cost: ¥15,000,000、Indirect Cost: ¥4,500,000)
Fiscal Year 2013: ¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000)
Fiscal Year 2012: ¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000)
Fiscal Year 2011: ¥10,140,000 (Direct Cost: ¥7,800,000、Indirect Cost: ¥2,340,000)
KeywordsDNA プローブ / DNAデバイス / 蛍光分子 / ナノバイオ / 環境応答分子 / 遺伝子診断 / DNAチップ
Research Abstract

We have designed a novel type of base-discriminating fluorescent (BDF) nucleosides which are used for SNP genotyping and gene detection. We also succeeded to design environmentally sensitive fluorescent (ESF) nucleosides that emit strong fluorescence at different wavelengths depending upon a difference of local environment near the ESF base. The newly designed ESF nucleosides may discriminate structural changes such as single strands, matches, mismatches and deletions when incorporated in DNA by a significant change of emission wavelengths as well as their intensities. Quencher and end free molecular beacons (MB) were discovered for the first time by using newly designed ESF nucleosides. These low cost MB were used for the gene detection in a cell. ESF nucleosides that are sensitive to pH were also designed. Such pH sensor ESF nucleoside that emits strong fluorescence only at bellow pH 5.5 was used for the detection of cancer cell.

Report

(4 results)
  • 2013 Annual Research Report   Final Research Report ( PDF )
  • 2012 Annual Research Report
  • 2011 Annual Research Report
  • Research Products

    (37 results)

All 2013 2012 2011

All Journal Article (23 results) (of which Peer Reviewed: 22 results) Presentation (14 results)

  • [Journal Article] An Environmentally Sensitive Fluorescent Purine Nucleoside that Changes Emission Wavelength upon Hybridization2013

    • Author(s)
      Y. Saito, A. Suzuki, Y. Okada, Y. Yamasaka, N. Nemoto, and I. Saito
    • Journal Title

      Chem. Commun

      Volume: 49 Pages: 5684-5686

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Solvatofluorochromic 7-Arylethynylated 7-Deaza-2'-deoxyadenosine Derivatives : Application to the Design of Environmentally Sensitive Fluorescent Probes Forming Stable DNA Duplexes2013

    • Author(s)
      A. Suzuki, K. Kimura, S. Ishioroshi, I. Saito, N. Nemoto, and Y. Saito
    • Journal Title

      Terahedron Lett

      Volume: 54 Pages: 2348-2352

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] A Peptide Nucleic Acid (PNA) Heteroduplex Containing an Inosine-Cytosine Base Pairs Discriminates a Single Nucleotide Difference in RNA2013

    • Author(s)
      K. Matsumoto, E. Nakata, T. Tamura, I. Saito, Y. Aizawa and T. Morii
    • Journal Title

      Chemistry -A European Journal

      Volume: 19 Pages: 5034-5040

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Naphthalene-based Environmentally Sensitive Fluorescent 8-Substituted 2 `-Deoxyadenosines : Application to DNA Detection2013

    • Author(s)
      A. Suzuki, N. Takahashi, Y. Okada, I. Saito, N. Nemoto, and Y. Saito
    • Journal Title

      Bioorg. Med. Chem. Lett

      Volume: 23 Pages: 886-886

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Solvatofluorochromic 7-Arylethynylated 7-Deaza-2'-deoxyadenosine Derivatives: Application to the Design of Environmentally Sensitive Fluorescent Probes Forming Stable DNA Duplexes.2013

    • Author(s)
      A. Suzuki, K. Kimura, S. Ishioroshi, I. Saito, N. Nemoto, and Y. Saito
    • Journal Title

      Tetrahedron Letters

      Volume: 54 Issue: 19 Pages: 2348-2352

    • DOI

      10.1016/j.tetlet.2013.02.063

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Efficiency Through DNA by Inserting Consecutive 5-Phenylethynyl-2 `-deoxyuridines as a Modulator2012

    • Author(s)
      M. Tanaka, K. Oguma, Y. Saito and I. Saito
    • Journal Title

      Chem. Commun

      Volume: 48 Pages: 9394-9396

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Fluorometric Detection of Adenine in TargebExciplex Formation with Fluorescent 8-Arylethynylated Deoxyguaanosine2012

    • Author(s)
      Y. Saito, K. Kugenuma, M. Tanaka, A. Suzuki, and I. Saito
    • Journal Title

      Bioorg. Med. Chem. Lett

      Volume: 22 Pages: 3723-3726

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Fluorescent Nucleosides with `On-Off ` Switching Function; pH-responsive Fluorescent Uridine Derivatives2012

    • Author(s)
      Y. Saito, S. Miyamoto, A. Suzuki, K. Matsumoto, T. Ishihara and I. Saito
    • Journal Title

      Bioorg.Med.Chem Lett

      Volume: 22 Pages: 2753-2756

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Enhancement of Fluorescence Quenching and Exciplex Formation in DNA Major Groove by Double Incorporation of Modified Fluorescent Deoxyuridines2012

    • Author(s)
      M. Tanaka, K. Oguma, Y. Saito, and I. Saito
    • Journal Title

      Bioorg.Med.Chem Lett

      Volume: 22 Pages: 4103-4105

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Enhancement of Fluorescence Quenching and Exciplex Formation in DNA Major Groove by Double Incorporation of Modified Fluorescent Deoxyuridines2012

    • Author(s)
      M. Tanaka, K. Oguma, Y. Saito, and I. Saito,
    • Journal Title

      Bioorg. Med. Chem. Lett.

      Volume: 22 Pages: 4103-4105

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Fluorescent Nucleosides with ‘On-Off’ Switching Function; pH-responsive Fluorescent Uridine Derivatives2012

    • Author(s)
      Y. Saito, S. Miyamoto, A. Suzuki, K. Matsumoto, T. Ishihara and I. Saito,
    • Journal Title

      Bioorg.Med.Chem.Lett.

      Volume: 22 Pages: 2753-2956

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Fluorometric Detection of Adenine in Target DNA by Exciplex Formation with Fluorescent 8-Arylethynylated Deoxyguaanosine .2012

    • Author(s)
      Y. Saito, K. Kugenuma, M. Tanaka, A. Suzuki, and I. Saito,
    • Journal Title

      Tetrahedron Lett.

      Volume: 52 Pages: 2359-2361

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Drastic Enhancement of Excess Electron-transfer Efficiency Through DNA by Inserting Consecutive 5-Phenylethynyl-2’-deoxyuridines as a Modulator.2012

    • Author(s)
      M. Tanaka, K. Oguma, Y. Saito and I. Saito,
    • Journal Title

      Chem. Commun.

      Volume: 48 Pages: 9394-9396

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Design and Application of Novel Nucleobase Analogs as an Environmentally Sensitive Probe2011

    • Author(s)
      M. Tanaka, K. Oguma, R. Kozakai, K. Kugenuma, Y. Saito and I. Saito
    • Journal Title

      Photomedicine. Photobiology

      Volume: 33 Pages: 47-484

    • Related Report
      2013 Final Research Report
  • [Journal Article] Symthesis and Photophysical Properties of Novel Push-Pull-TypeSolvatochromic-7-Deaza-2 `-deoxyourin epurine Nucleosides2011

    • Author(s)
      Y. Saito, A. Suzuki, S. Ishioroshi and I. Saito
    • Journal Title

      Tetrahedron Lett.

      Pages: 4726-4729

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Stabilization of DNA Duplex by 2-Substituted Adenine as a Minor Groove Modifier2011

    • Author(s)
      M. Tanaka, R. Kozakai, Y. Saito and I. Saito
    • Journal Title

      Bioorg.Med.Chem Lett

      Volume: 21 Pages: 7021-7024

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Environmentally Sensitive 2 `-Deoxyguanosine Containing Solvatochromic Pyrene Fluorophore2011

    • Author(s)
      Y. Saito, Y. Shinohara, S. Ishioroshi, A. Suzuki, M. Tanaka and I. Saito
    • Journal Title

      Tetrahedron Lett

      Volume: 52 Pages: 2359-2361

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Design and Synthesis of Highly Solvatochromic Fluorescent 2 `-Deoxyguanosine and Adenosine Analogs2011

    • Author(s)
      K. Matsumoro, N. Takahashi, A. Suzuki, T. Morii, Y. Saito and I. Saito
    • Journal Title

      Bioorg.Med.Chem Lett

      Volume: 21 Pages: 1275-1279

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and Photophysical Properties of 8-Arylbutadienyl 2 `-Deoxyguanosines2011

    • Author(s)
      Y. Saito, M. Koda, Y. Shinohara and I. Saito
    • Journal Title

      Tetrahedron Lett

      Volume: 52 Pages: 491-494

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and Photophysical Properties of 8-Arylbutadienyl 2'-Deoxyguanosines2011

    • Author(s)
      Y.Saito, M.Koda, Y.Shinohara, I.Saito
    • Journal Title

      Tetrahedron Lett

      Volume: 52 Pages: 491-494

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Design and Synthesis of Highly Solvatochromic Fluorescent 2'-Deoxyguanosine and Adenosine Analogs2011

    • Author(s)
      K.Matsumoro, N.Takahashi, A.Suzuki, T.Morii, Y.Saito, I.Saito
    • Journal Title

      Bioorg.Med.Chem.Lett.

      Volume: 21 Pages: 1275-1279

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Environmentally Sensitive 2'-Deoxyguanosine Containing Solvatochromic Pyrene Fluorophore2011

    • Author(s)
      Y.Saito, Y.Shinohara, S.Ishioroshi, A.Suzuki, M.Tanaka, I.Saito
    • Journal Title

      Tetrahedron Lett

      Volume: 52 Pages: 2359-2361

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Stabilization of DNA Duplex by 2-Substituted Adenine as a Minor Groove Modifier2011

    • Author(s)
      M.Tanaka, R.Kozakai, Y.Saito, I.Saito
    • Journal Title

      Bioorg.Med.Chem.Lett

      Volume: 21 Pages: 7021-7024

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Presentation] Synthesis and photophysical properties of environmentally sensitive 8-aza-7deazapurine nucleosides forming stable Watson-Crick base pair2013

    • Author(s)
      A. Suzuki, Y. Yamasaka, I.Saito and Y. Saito
    • Organizer
      ISNAC 2013(第40回国際核酸化学シンポジウム)
    • Place of Presentation
      神奈川大学
    • Year and Date
      2013-11-13
    • Related Report
      2013 Final Research Report
  • [Presentation] Environmentally sensitive fluorescent 8-aza-7-deaza-2' -deoxy-adenosines that form a stable Watson-Crick base pair and their photophysical properties2013

    • Author(s)
      A. Suzuki, I. Saito, N. Nemoto, Y. Saito
    • Organizer
      International Symposium for the 70th Anniversary of the Tohoku Branch of the Chemical Society of Japan
    • Place of Presentation
      東北大学, 川内北キャンパス
    • Related Report
      2013 Final Research Report
  • [Presentation] 環境感応型蛍光性8-アザ-7-デアザ-2'-デオキシアデノシン誘導体の開発とDNAプローブへの応用2013

    • Author(s)
      鈴木梓・ 齋藤烈・ 根本修克・ 齋藤義雄
    • Organizer
      2013年光化学討論会
    • Place of Presentation
      愛媛大学, 城北地区
    • Related Report
      2013 Final Research Report
  • [Presentation] 8-アザ-7-デアザプリン骨格を有する環境感応型蛍光核酸塩基の開発と遺伝子検出への応用2013

    • Author(s)
      鈴木梓・ 齋藤烈・ 齋藤義雄
    • Organizer
      第35回日本光医学・光生物学会
    • Place of Presentation
      アクトシティ浜松, コングレスセンター
    • Related Report
      2013 Final Research Report
  • [Presentation] 新規蛍光性8-アザ-7-デアザプリンヌクレオシド誘導体の合成と光学と光学特性2013

    • Author(s)
      鈴木梓・岡田雄慈・本田かおり・齋藤烈・ 齋藤義雄
    • Organizer
      日本化学会第93春季年会(2013)
    • Place of Presentation
      立命館大学びわこ・くさつキャンパス
    • Related Report
      2013 Final Research Report
  • [Presentation] 7位にアリールエチニル基を有する8-アザ-7-デアザ-2'-デオキシグアノシン誘導体を含むDNAプローブの合成と光学特性2013

    • Author(s)
      山坂勇喜、鈴木梓、岡田雄慈、齋藤烈、齋藤義雄
    • Organizer
      2013年光化学討論会
    • Place of Presentation
      愛媛大学
    • Related Report
      2013 Annual Research Report
  • [Presentation] デアザプリン骨格を有する新規蛍光ヌクレオシドの合成と光学特性2012

    • Author(s)
      鈴木梓・石下真也・簗場匠・工藤裕也・齋藤烈・根本修克・齋藤義雄
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶応義塾大学
    • Year and Date
      2012-03-26
    • Related Report
      2011 Annual Research Report
  • [Presentation] 8位にアリールエチニル基を有する2'-デオキシアデノシン誘導体の合成と光学特性2012

    • Author(s)
      岡田雄慈・高橋尚弥・桑原拓也・横山祥太・齋藤烈・齋藤義雄
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶応義塾大学
    • Year and Date
      2012-03-26
    • Related Report
      2011 Annual Research Report
  • [Presentation] DNA二本鎖中に複数導入した修飾核酸塩基の光物性2012

    • Author(s)
      田仲真紀子・小熊一裕・小坂井亮太・齋藤義雄・齋藤烈
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶応義塾大学
    • Year and Date
      2012-03-26
    • Related Report
      2011 Annual Research Report
  • [Presentation] Synthesis and photophysical properties of environmentally sensitive 7-deaza-2' -deoxyadenosine analogs2012

    • Author(s)
      A. Suzuki, I. Saito, N. Nemoto, Y. Saito
    • Organizer
      ISNAC 2012 (第39回国際核酸化学シンポジウム)
    • Place of Presentation
      名古屋大学, 東山キャンパス
    • Related Report
      2013 Final Research Report
  • [Presentation] pH変化に敏感なアントラセン骨格を有する蛍光性ヌクレオシドの開発と応用2012

    • Author(s)
      鈴木梓・宮本茂憲・横山祥太・石原務・ 齋藤烈・根本修克・ 齋藤義雄
    • Organizer
      2012年光化学討論会
    • Place of Presentation
      東京工業大学大岡山キャンパス
    • Related Report
      2013 Final Research Report
  • [Presentation] Synthesis and photophysical properties of novel push-pull type fluorescent purine and 8-deazapurine 2` -deosynucleotides2012

    • Author(s)
      A.Suzuki, I.Saito, N. Nemoto and Y. Saito
    • Organizer
      Centre Mont-Royal
    • Place of Presentation
      カナダ・モントリオールCentre Mont-Royal
    • Related Report
      2013 Final Research Report
  • [Presentation] デアザプリン骨格を有する新規蛍光ヌクレオシドの合成と光学特性2012

    • Author(s)
      鈴木梓・石下真也・簗場匠・ 齋藤烈・根本修克・ 齋藤義雄
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶応義塾大学, 日吉キャンパス
    • Related Report
      2013 Final Research Report
  • [Presentation] Efficient excess electron transfer through modified DNA using 2'-deoxyuridine derivatives2012

    • Author(s)
      M. Tanaka, K. Oguma, Y. Saito I. Saito
    • Organizer
      The 39th International Symposium on Nucleic Acids Chemistry, Nagoya, November, 2012
    • Place of Presentation
      名古屋大学豊田講堂
    • Related Report
      2012 Annual Research Report

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Published: 2011-04-06   Modified: 2019-07-29  

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