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Development of enzyme-responsive anticancer agents and fluorescent probes targeting the biosynthesis of nucleotides

Research Project

Project/Area Number 24790108
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Drug development chemistry
Research InstitutionGifu University

Principal Investigator

OKA Natsuhisa  岐阜大学, 工学部, 准教授 (50401229)

Project Period (FY) 2012-04-01 – 2014-03-31
Project Status Completed (Fiscal Year 2013)
Budget Amount *help
¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000)
Fiscal Year 2013: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Fiscal Year 2012: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Keywords核酸の生合成 / カルボニル基のリン酸化 / ヌクレオチド / 酵素応答性分子 / イノシン / 蛍光標識化 / 抗がん剤 / 蛍光プローブ / アデニロコハク酸合成酵素 / CTP合成酵素
Research Abstract

In this study, we developed a novel method to synthesize chemically modified analogs of inosine 6-phosphates, which are observed in the biosynthesis of nucleotides. For this purpose, we applied a non-nucleophilic acidic activator, N-(cyanomethyl)dimethylammonium triflate (CMMT), that we developed recently, to the phosphitylation of carbonyl oxygen by the phosphoramidite method, which enabled us to synthesize inosine 6-phosphate diesters bearing various substituents on the phosphate. Furthermore, we evaluated the stability of the inosine 6-phosphate diesters to find that they were stable in neutral aqueous solutions. These molecules will be useful for biological and pharmaceutical studies of the biosynthesis of nucleotides.

Report

(3 results)
  • 2013 Annual Research Report   Final Research Report ( PDF )
  • 2012 Research-status Report
  • Research Products

    (38 results)

All 2014 2013 2012 Other

All Journal Article (10 results) (of which Peer Reviewed: 10 results) Presentation (25 results) (of which Invited: 3 results) Remarks (3 results)

  • [Journal Article] Solid-phase Synthesis of P-Boronated Oligonucleotides by the H-Boranophosphonate Method2014

    • Author(s)
      Sho Uehara, Shingo Hiura, Renpei Higashida, Natsuhisa Oka, Takeshi Wada
    • Journal Title

      J. Org. Chem.

      Volume: 79 Issue: 8 Pages: 3465-3472

    • DOI

      10.1021/jo500185b

    • Related Report
      2013 Annual Research Report 2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] 35. Synthesis of inosine 6-phosphate diesters via phosphitylation of the carbonyl oxygen2013

    • Author(s)
      Oka, N.; Morita, Y.; Itakura, Y.; Ando, K.
    • Journal Title

      Chem. Commun.

      Volume: 49 Issue: 98 Pages: 11503-11505

    • DOI

      10.1039/c3cc46617e

    • Related Report
      2013 Annual Research Report 2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Glycosylation of alcohols using glycosyl boranophosphates as glycosyl donors2013

    • Author(s)
      Natsuhisa Oka, Shiro Tatsumi, Fumiko Matsumura, Takeshi Wada
    • Journal Title

      Tetrahedron Lett.

      Volume: 54 Issue: 29 Pages: 3731-3734

    • DOI

      10.1016/j.tetlet.2013.04.032

    • Related Report
      2013 Annual Research Report 2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Stereocontrolled synthesis of dinucleoside phosphorothioates using a fluorous tag2013

    • Author(s)
      Oka, N.; Murakami, R.; Kondo, T.; Wada, T
    • Journal Title

      J.Fluorine Chem

      Volume: 150 Pages: 85-91

    • DOI

      10.1016/j.jfluchem.2013.03.013

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Purification and comparison of native and recombinant tRNA-guanine transglycosylases from Methanosarcina acetivorans.2013

    • Author(s)
      Nomura, Y, Onda, Y, Ohno, S, Taniguchi, H, Ando, K, Oka, N, Nishikawa, K, Yokogawa, T
    • Journal Title

      Protein Expr. Purif.

      Volume: 88 Issue: 1 Pages: 13-19

    • DOI

      10.1016/j.pep.2012.11.009

    • Related Report
      2013 Final Research Report 2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Stereocontrolled solid-phase synthesis of phosphorothioate oligoribonucleotides using 2′-O-(2-cyanoethoxymethyl)-nucleoside 3′-O-oxazaphospholidine monomers2012

    • Author(s)
      Nukaga, Y.; Yamada, K.; Ogata, T.; Oka, N.; Wada, T
    • Journal Title

      J. Org. Chem

      Volume: 77 Issue: 18 Pages: 7913-7922

    • DOI

      10.1021/jo301052v

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of nucleoside 5'-boranophosphorothioate derivatives using an H-boranophosphonate monoester as a precursor2012

    • Author(s)
      Oka, N.; Takayama, Y.; Ando, K.; Wada, T. Bioorg
    • Journal Title

      Med. Chem. Lett

      Volume: 22 Issue: 14 Pages: 4571-4574

    • DOI

      10.1016/j.bmcl.2012.05.093

    • Related Report
      2013 Final Research Report 2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Stereocontrolled synthesis of oligodeoxyribonucleoside boranophosphates by an oxazaphospholidine approach using acid-labile N-protecting groups2012

    • Author(s)
      Iwamoto, N.; Oka, N.; Wada, T
    • Journal Title

      Tetrahedron Lett

      Volume: 53 Issue: 33 Pages: 4361-4364

    • DOI

      10.1016/j.tetlet.2012.06.015

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of 2-pyridylphosphinate and thiophosphinate derivatives by nucleophilic aromatic substitution of N-methoxypyridinium tosylates2012

    • Author(s)
      Oka, N.; Ito, K.; Tomita, F.; Ando, K
    • Journal Title

      Chem. Lett

      Volume: 41 Issue: 12 Pages: 1630-1632

    • DOI

      10.1246/cl.2012.1630

    • NAID

      10031135774

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Recent Progress in the Synthesis of Glycosyl Phosphate Derivatives2012

    • Author(s)
      Oka, N.; Sato, K.; Wada, T
    • Journal Title

      Trends in Glycoscience and Glycotechnology

      Volume: 24 Issue: 138 Pages: 152-168

    • DOI

      10.4052/tigg.24.152

    • NAID

      10031146667

    • ISSN
      0915-7352, 1883-2113
    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Presentation] キラル酸活性化剤を用いるジヌクレオシドホスホロチオエートの立体選択的合成2014

    • Author(s)
      酒井智紀・岡夏央・小里建喬・安藤香織
    • Organizer
      日本化学会第94春季大会
    • Place of Presentation
      名古屋大学
    • Year and Date
      2014-03-30
    • Related Report
      2013 Annual Research Report 2013 Final Research Report
  • [Presentation] 7-エチニル-7-デアザグアニンの合成法の開発2014

    • Author(s)
      清水陽介・岡夏央・安藤香織・大野敏・横川隆志
    • Organizer
      日本化学会第94春季大会
    • Place of Presentation
      名古屋大学
    • Year and Date
      2014-03-30
    • Related Report
      2013 Annual Research Report 2013 Final Research Report
  • [Presentation] ヨウ化糖をグリコシルドナーとするα-リボフラノシドの合成2014

    • Author(s)
      梶野麟・岡夏央・安藤香織
    • Organizer
      日本化学会第94春季大会
    • Place of Presentation
      名古屋大学
    • Year and Date
      2014-03-28
    • Related Report
      2013 Annual Research Report 2013 Final Research Report
  • [Presentation] キラルリン(III)原子の不斉制御によるリン原子修飾オリゴ核酸の立体選択的合成2014

    • Author(s)
      岡夏央
    • Organizer
      日本薬学会第134年会
    • Place of Presentation
      熊本大学黒髪キャンパス
    • Year and Date
      2014-03-28
    • Related Report
      2013 Final Research Report
    • Invited
  • [Presentation] キラルリン(III)原子の不斉制御による リン原子修飾オリゴ核酸の立体選択的合成2014

    • Author(s)
      岡 夏央
    • Organizer
      日本薬学会第134年会
    • Place of Presentation
      熊本大学黒髪キャンパス
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] リン原子修飾オリゴ核酸の立体選択的合成法の開発2013

    • Author(s)
      岡夏央
    • Organizer
      合同シンポジウム-日本プロセス化学会2013ウィンターシンポジウム
    • Place of Presentation
      仙台市民会館
    • Year and Date
      2013-11-29
    • Related Report
      2013 Final Research Report
  • [Presentation] Synthesis of O6-phosphoryl inosine derivatives by phosphitylation of carbonyl oxygen2013

    • Author(s)
      Natsuhisa Oka, Yasuhiro Morita, Yuta Itakura, Kaori Ando
    • Organizer
      The 40th International Symposium on Nucleic Acid Chemistry (ISNAC2013)
    • Place of Presentation
      Kanagawa University
    • Year and Date
      2013-11-14
    • Related Report
      2013 Final Research Report
  • [Presentation] リン原子修飾オリゴ核酸の立体選択的合成法の開発2013

    • Author(s)
      岡夏央
    • Organizer
      第44回中部化学関係学協会支部連合秋季大会
    • Place of Presentation
      静岡大学浜松キャンパス
    • Year and Date
      2013-11-03
    • Related Report
      2013 Annual Research Report 2013 Final Research Report
  • [Presentation] ヨウ化糖を用いるアルコールのα選択的リボフラノシル化反応の開発2013

    • Author(s)
      梶野麟・岡夏央・竹内薫・永川晴奈・安藤香織
    • Organizer
      第43回複素環化学討論会
    • Place of Presentation
      長良川国際会議場
    • Year and Date
      2013-10-17
    • Related Report
      2013 Annual Research Report 2013 Final Research Report
  • [Presentation] ヨウ化糖をグリコシルドナーとするα選択的リボフラノシル化反応の開発2013

    • Author(s)
      岡夏央・梶野麟・竹内薫・永川晴奈・安藤香織
    • Organizer
      第7回バイオ関連化学シンポジウム
    • Place of Presentation
      名古屋大学
    • Year and Date
      2013-09-28
    • Related Report
      2013 Annual Research Report 2013 Final Research Report
  • [Presentation] Rin Kajino, Kaori Andoα-Selective ribofuranosylation of alcohols using a ribofuranosyl iodide as a glycosyl donor2013

    • Author(s)
      Natsuhisa Oka, Kaoru Takeuchi, Haruna Nagakawa
    • Organizer
      Nagoya Symposium 2013
    • Place of Presentation
      Nagoya University
    • Year and Date
      2013-05-23
    • Related Report
      2013 Final Research Report
  • [Presentation] 創薬を指向したホウ素修飾核酸およびα選択的リボフラノシドの効率的合成法の開発2013

    • Author(s)
      岡夏央
    • Organizer
      Biotech 2013
    • Place of Presentation
      東京ビッグサイト
    • Year and Date
      2013-05-10
    • Related Report
      2013 Annual Research Report 2013 Final Research Report
  • [Presentation] O^6-ホスホリルイノシン誘導体の合成法の開発2013

    • Author(s)
      森田康裕・岡夏央・安藤香織
    • Organizer
      日本化学会第93春季大会
    • Place of Presentation
      立命館大学びわこ・くさつキャンパス
    • Year and Date
      2013-03-24
    • Related Report
      2013 Final Research Report
  • [Presentation] 2-ピリジルホスフィン酸誘導体の合成法の開発とルイス塩基触媒としての応用2013

    • Author(s)
      伊藤光佑・岡夏央・安藤香織
    • Organizer
      日本化学会第93春季大会
    • Place of Presentation
      立命館大学びわこ・くさつキャンパス
    • Year and Date
      2013-03-23
    • Related Report
      2013 Final Research Report
  • [Presentation] ヨウ化糖を用いるα選択的リボフラノシル化反応の開発2013

    • Author(s)
      竹内薫・岡夏央・永川晴奈・安藤香織
    • Organizer
      日本化学会第93春季大会
    • Place of Presentation
      立命館大学びわこ・くさつキャンパス
    • Year and Date
      2013-03-23
    • Related Report
      2013 Final Research Report
  • [Presentation] Synthesis of O6-phosphoryl inosine derivatives by phosphitylation of carbonyl oxygen2013

    • Author(s)
      Natsuhisa Oka, Yasuhiro Morita, Yuta Itakura, Kaori Ando
    • Organizer
      The 40th International Symposium on Nucleic Acid Chemistry (ISNAC2013)
    • Place of Presentation
      神奈川大学
    • Related Report
      2013 Annual Research Report
  • [Presentation] リン原子修飾オリゴ核酸の立体選択的合成法の開発2013

    • Author(s)
      岡 夏央
    • Organizer
      合同シンポジウム-日本プロセス化学会2013ウィンターシンポジウム・新学術領域「有機分子触媒による未来型分子変換」第3回公開シンポジウム-
    • Place of Presentation
      仙台市民会館
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] O6-ホスホリルイノシン誘導体の合成法の開発2013

    • Author(s)
      森田 康裕・岡 夏央・安藤 香織
    • Organizer
      日本化学会第93春季大会
    • Place of Presentation
      立命館大学びわこ・くさつキャンパス
    • Related Report
      2012 Research-status Report
  • [Presentation] Synthesis of Nucleoside 5'-(P-Borano)phosphate Derivatives Using Nucleoside 5'-H-Boranophosphonates as Precursors2012

    • Author(s)
      Natsuhisa Oka, Yuji Takayama, Kaori Ando, Takeshi Wada
    • Organizer
      The 39th International Symposium on Nucleic Acid Chemistry (ISNAC2012)
    • Place of Presentation
      Nagoya University
    • Year and Date
      2012-11-16
    • Related Report
      2013 Final Research Report
  • [Presentation] 2-ピリジルホスフィン酸誘導体の合成法の開発2012

    • Author(s)
      伊藤光佑・岡夏央・安藤香織
    • Organizer
      第43回中部化学関係学協会支部連合秋季大会
    • Place of Presentation
      名古屋工業大学
    • Year and Date
      2012-11-11
    • Related Report
      2013 Final Research Report
  • [Presentation] ヨウ化糖を用いるα選択的リボフラノシル化反応の開発2012

    • Author(s)
      竹内薫・岡夏央・永川晴奈・安藤香織
    • Organizer
      第43回中部化学関係学協会支部連合秋季大会
    • Place of Presentation
      名古屋工業大学
    • Year and Date
      2012-11-10
    • Related Report
      2013 Final Research Report
  • [Presentation] O^6-ホスホリルイノシン誘導体の合成法の開発2012

    • Author(s)
      森田康裕・岡夏央・安藤香織
    • Organizer
      第43回中部化学関係学協会支部連合秋季大会
    • Place of Presentation
      名古屋工業大学
    • Year and Date
      2012-11-10
    • Related Report
      2013 Final Research Report
  • [Presentation] O6-ホスホリルイノシン誘導体の合成法の開発2012

    • Author(s)
      森田 康裕・岡 夏央・安藤 香織
    • Organizer
      第43回中部化学関係学協会支部連合秋季大会
    • Place of Presentation
      名古屋工業大学
    • Related Report
      2012 Research-status Report
  • [Presentation] Synthesis of Nucleoside 5'-(P-Borano)phosphate Derivatives Using Nucleoside 5'-H-Boranophosphonates as Precursors2012

    • Author(s)
      Natsuhisa Oka, Yuji Takayama, Kaori Ando and Takeshi Wada
    • Organizer
      The 39th International Symposium on Nucleic Acid Chemistry
    • Place of Presentation
      名古屋大学豊田講堂
    • Related Report
      2012 Research-status Report
  • [Presentation] α-Selective ribofuranosylation of alcohols using a ribofuranosyl iodide as a glycosyl donor

    • Author(s)
      Natsuhisa Oka, Kaoru Takeuchi, Haruna Nagakawa, Rin Kajino, Kaori Ando
    • Organizer
      Nagoya Symposium 2013
    • Place of Presentation
      Nagoya University
    • Related Report
      2013 Annual Research Report
  • [Remarks]

    • URL

      http://www1.gifu-u.ac.jp/~ando_ap/

    • Related Report
      2013 Final Research Report
  • [Remarks] 岐阜大学工学部化学・生命工学科安藤研究室ホームページ

    • URL

      http://www1.gifu-u.ac.jp/~ando_ap/

    • Related Report
      2013 Annual Research Report
  • [Remarks] 岐阜大学工学部化学・生命工学科安藤研究室ホームページ

    • URL

      http://www1.gifu-u.ac.jp/~ando_ap/

    • Related Report
      2012 Research-status Report

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Published: 2013-05-31   Modified: 2019-07-29  

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