Synthesis and properties of 4'-selenoRNA based on biological equivalence

• Project/Area Number: 20611001
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Chemical biology
• Research Institution: Hokkaido University
• Principal Investigator: MINAKAWA Noriaki Hokkaido University, 大学院・ヘルスバイオサイエンス研究部, 教授 (40209820)
• Project Period (FY): 2008 – 2010
• Project Status: Completed (Fiscal Year 2010)
• Budget Amount: ¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000); Fiscal Year 2010: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000); Fiscal Year 2009: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000); Fiscal Year 2008: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
• Keywords: ヌクレオシド / RNA / 4'-セレノRNA / 生物学的等価性 / セレン

Research Abstract

In this work, I aimed to prepare a new chemically modified RNA molecule exhibiting a biological equivalence with natural RNA. To be concrete, 4'-selenoRNA and 2'-OMe-4'-selenoRNA, in which the furanose ring oxygen is replaced by a seleno atom, were prepared and their properties were examined. Accordingly, these RNA molecules showed a higher hybridization property and nuclease resistance.

Research Products

• [Journal Article] Synthesis and characterization of oligodeoxynucleotides containing a novel tetraazabenso[cd]azulene ; naphthyridine base pair (2011)
  • Author(s): Y.Hirama, et al.
  • Journal Title: Bioorg.Med.Chem. Volume: 19 Pages: 352-358
  • Peer Reviewed
• [Journal Article] A convenient RNA synthesis using a phosphoramidite possessing a biotinylated photocleavable group. (2010)
  • Author(s): K.Tomaya, M.Takahashi, N.Minakawa, A.Matsuda
  • Journal Title: Org.Lett. 131 Pages: 3836-3839
  • Peer Reviewed
• [Journal Article] Synthesis and properties of a novel nucleoside derivative possessing a 2,3,5,6-tetraazabenzo[cd]azulene skelton. (2010)
  • Author(s): Y.Hirama, H.Abe, N.Minakawa, A.Matsuda
  • Journal Title: Tetrahedron 66 Pages: 8402-8406
  • Peer Reviewed
• [Journal Article] Convenient RNA Synthesis Using a Phosphoramidite Possessing a Biotinylated Photocleavable Group (2010)
  • Author(s): K.Tomaya, et al.
  • Journal Title: Org.Lett. Volume: 12 Pages: 3836-3839
  • Peer Reviewed
• [Journal Article] Synthesis and properties of a novel nucleoside derivative possessing a 2,3,5,6-tetraazabenso[cd]azulene skelton (2010)
  • Author(s): Y.Hirama, et al.
  • Journal Title: Tetrahedron Volume: 66 Pages: 8402-8406
  • Peer Reviewed
• [Journal Article] Selective recognition of unnatural imidazopyridopyrimidine : naphthyridine base pairs consisting of four hydrogen bonds by the Klenow fragment. (2009)
  • Author(s): N.Minakawa, S.Ogata, M.Takahashi, A.Matsuda
  • Journal Title: J.Am.Chem.Soc. 131 Pages: 1644-1645
  • Peer Reviewed
• [Journal Article] Synthesis and characterization of 2'-modified-4'-thioRNA : a comprehensive comparison of nuclease stability. (2009)
  • Author(s): M.Takahashi, N.Minakawa, A.Matsuda
  • Journal Title: Nucleic Acids Res. 37 Pages: 1353-1362
  • NAID: 120003260045
  • Peer Reviewed
• [Journal Article] Selective recognition of unnatural imidazopyridopyrimidine : naphthyridine base pairs consisting of four hydrogen bonds by the Klenow fragment (2009)
  • Author(s): N.Minakawa, et al.
  • Journal Title: J.Am.Chem.Soc. 131 Pages: 1644-1645
  • Peer Reviewed
• [Journal Article] Synthesis and characterization of 2'-modified-4'-thioRNA : a comprehensive comparison of nuclease stability (2009)
  • Author(s): M.Takahashi, et al.
  • Journal Title: Nucleic Acids Res. 37 Pages: 1805-1812
  • Peer Reviewed
• [Journal Article] Unnatural imidazopyridopyrimidine : naphthyridine base pairs : selective incorporation and extension reaction by Deep Vent (exo^-) DNA polymerase (2009)
  • Author(s): S.Ogata, et al.
  • Journal Title: Nucleic Acids Res. 37 Pages: 5602-5609
  • Peer Reviewed
• [Journal Article] Unnatural imidazopyridopyrimidine : naphthyridine base pairs : selective incorporation and extension reaction by DNA polymerase (2009)
  • Author(s): N.Minakawa, et al.
  • Journal Title: Nucleic Acids Symp.Ser. 53 Pages: 125-126
• [Journal Article] Unxepected A-form formation of 4'-thioDNA in solution, revealed by NMR, and the implications as to the mechanism of nuclease-resistance. (2008)
  • Author(s): A.Matsugami, T.Ohyama, M.Inada, N.Inoue, N.Minakawa, A.Matsuda, M.Katahira
  • Journal Title: Nucleic Acids Res. 36 Pages: 1805-1812
  • Peer Reviewed
• [Journal Article] Oligodeoxynucleotides containing 3-bromo-3-deazaadenine and 7-bromo-7-deazaadenine nucleosides as chemical probes to investigate DNA-protein interaction. (2008)
  • Author(s): N.Minakawa, Y.Kawano, S.Murata, N.Inoue, A.Matsuda
  • Journal Title: ChemBioChem 9 Pages: 464-470
  • Peer Reviewed
• [Journal Article] Synthesis and Crystal Structure of 2'-Deoxy-2'-fluoro-4'-thionucleosides : Substrates for the Synthesis on Novel Modified RNAs (2008)
  • Author(s): M. Takahashi, et.al.
  • Journal Title: Tetrahedron 64 Pages: 4313-4324
  • Peer Reviewed
• [Journal Article] Synthesis and properties of oligonucleotides containing 4'-selenoribonu cleosides (2008)
  • Author(s): Y. Inagaki, et.al.
  • Journal Title: Nucleic Acids Symp. Ser 52 Pages: 329-330
• [Presentation] Convenient RNA synthesis using a phosphoramidite possessing a photocleavable group (2010)
  • Author(s): N.Minakawa
  • Organizer: 日韓合同シンポジウム
  • Place of Presentation: 淡路市
  • Year and Date: 2010-12-22
• [Presentation] Synthesis of 4'-selenoribonucleosides using hypervalent iodine (2010)
  • Author(s): H.Taniike, et al.
  • Organizer: 日韓合同シンポジウム
  • Place of Presentation: 淡路市
  • Year and Date: 2010-12-22
• [Presentation] Synthesis of 4'-selenoribonucleosides using hypervalent iodine (2010)
  • Author(s): H.Taniike, et al.
  • Organizer: 2010環太平洋国際化学会議PACIFICHEM2010
  • Place of Presentation: ホノルル(アメリカ)
  • Year and Date: 2010-12-15
• [Presentation] Synthesis and properties of 2'-O-MOE-4'-thioRNA (2010)
  • Author(s): Y.Saito, et al.
  • Organizer: 2010環太平洋国際化学会議PACIFICHEM2010
  • Place of Presentation: ホノルル(アメリカ)
  • Year and Date: 2010-12-15
• [Presentation] Enzymatic recognition of unnatural imidazopyridopyrimidine : naphthyridine base pair, ImN^<N>:NaO^<o> by DNA polymerase (2010)
  • Author(s): N.Tarashima, et al.
  • Organizer: 2010環太平洋国際化学会議PACIFICHEM2010
  • Place of Presentation: ホノルル(アメリカ)
  • Year and Date: 2010-12-15
• [Presentation] Evaluation of potency and duration of gene silencing activity by siRNAs containing 2'-O-methyl-4'-thioribonucleosides (2010)
  • Author(s): M.Takahashi, et al.
  • Organizer: 2010環太平洋国際化学会議PACIFICHEM2010
  • Place of Presentation: ホノルル(アメリカ)
  • Year and Date: 2010-12-15
• [Presentation] 新規抗がん剤候補化合物探索を目指した構造活性相関研究 (2010)
  • Author(s): 徳田美幸, ら
  • Organizer: 日本生化学会
  • Place of Presentation: 神戸市
  • Year and Date: 2010-12-07
• [Presentation] 光解離性保護基を利用した高純度RNAの簡便合成法の開発 (2010)
  • Author(s): 苫谷晃太, ら
  • Organizer: アンチセンスシンポジウム
  • Place of Presentation: 神戸市
  • Year and Date: 2010-12-04
• [Presentation] 4'-thioDNA修飾によるヌクレアーゼ抵抗性ベクターの開発 (2010)
  • Author(s): 丸山豪斗, ら
  • Organizer: アンチセンスシンポジウム
  • Place of Presentation: 神戸市
  • Year and Date: 2010-12-04
• [Presentation] 4'-thioDNA修飾型ベクターの創製研究 (2010)
  • Author(s): 丸山豪斗, ら
  • Organizer: 日本薬学会北海道支部例会
  • Place of Presentation: 札幌市
  • Year and Date: 2010-11-27
• [Presentation] NMR study of the DNA duplex containing a thermally stable base-pairing motif (2010)
  • Author(s): K.Furuita, et al.
  • Organizer: 国際核酸化学シンポジウム
  • Place of Presentation: 横浜市
  • Year and Date: 2010-11-10
• [Presentation] Synthesis of 4'-selenoribonucleosides using hypervalent iodine (2010)
  • Author(s): H.Taniike, Y.Inagaki, A.Matsuda, N.Minakawa
  • Organizer: 2010環太平洋国際化学会議PACIFICHEM2010
  • Place of Presentation: ホノルル
• [Presentation] Evaluation of potency and duration of gene silencing activity by siRNAs containing hybrid type of chemically modified nucleotides (2010)
  • Author(s): M.Takahashi, C.Nagai, H.Hatakeyama, N.Minakawa, H.Harashima, A.Matsuda
  • Organizer: International Round Table
  • Place of Presentation: France
• [Presentation] Investigation of Gene-silencing Effect Using siRNAs Modified with 2'-O-Methyl-4'-thioribonucleosides (2009)
  • Author(s): M.Takahashi, et al.
  • Organizer: 国際核酸医薬シンポジウム(第5回OTS年会、第19回アンチセンスシンポジウム)
  • Place of Presentation: 福岡市
  • Year and Date: 2009-11-04
• [Presentation] Development od Chemical Probes to Investigate the Molecular Mechanism of RNAi (2009)
  • Author(s): S.Ide, et al.
  • Organizer: 国際核酸医薬シンポジウム(第5回OTS年会、第19回アンチセンスシンポジウム)
  • Place of Presentation: 福岡市
  • Year and Date: 2009-11-04
• [Presentation] Unnatural imidazopyridopyrimidine : naphthyridine base pairs : selective incorporation and extension reaction by DNA polymerase (2009)
  • Author(s): N.Minakawa, et al.
  • Organizer: The 6^<th> International Symposium on Nucleic Acids Chemistry
  • Place of Presentation: Takayama, Gifu
  • Year and Date: 2009-09-29
• [Presentation] ブロモデアザアデニンリボヌクレオシド類を含むRNAの合成とその性質 (2009)
  • Author(s): 井手志穂, 他
  • Organizer: 日本薬学会第129年会
  • Place of Presentation: 京都市
  • Year and Date: 2009-03-26
• [Presentation] 2'-O-メチル-4'-セレノリボヌクレオシドを含むRNAの合成と性質解析 (2009)
  • Author(s): 稲垣勇典, 他
  • Organizer: 日本薬学会第129年会
  • Place of Presentation: 日本薬学会第129年会
  • Year and Date: 2009-03-26
• [Presentation] 2'-置換-4'-チオ核酸の酵素的合成 (2009)
  • Author(s): 高橋真由美, 他
  • Organizer: 日本薬学会第129年会
  • Place of Presentation: 日本薬学会第129年会
  • Year and Date: 2009-03-26
• [Presentation] 核酸医薬品創製を志向する糖部修飾型人工核酸:apioNAの酵素合成 (2009)
  • Author(s): 片岡真由美, 他
  • Organizer: 日本薬学会第129年会
  • Place of Presentation: 日本薬学会第129年会
  • Year and Date: 2009-03-26
• [Presentation] Development od Chemical Probes to Investigate the Molecular Mechanism of RNAi (2009)
  • Author(s): S.Ide, N.Minakawa, A.Matsuda
  • Organizer: 国際核酸医薬シンポジウム
  • Place of Presentation: Fukuoka
• [Presentation] Unnatural imidazopyridopyrimidine : naphthyridine base pairs : selective incorporation and extension reaction by DNA polymerase. (2009)
  • Author(s): N.Minakawa, S.Ogata, M.Takahashi, A.Matsuda
  • Organizer: The 6^<th> International Symposium on Nucleic Acids Chemistry
  • Place of Presentation: Takayama Gifu
• [Presentation] Synthesis and properties of oligonucleotides containing 4'-selenoribonu cleosides (2008)
  • Author(s): Y. Inagaki, ら
  • Organizer: Joint Symposium of the 18^<th> International Roundtable on Nucleosides, Nucleotides and Nucleic Acids and the 35^<th> International Symposium on Nucleic Acids Chemistry
  • Place of Presentation: Kyoto
  • Year and Date: 2008-09-11
• [Presentation] Synthesis and properties of 2'-modified-4'-thioRNA. (2008)
  • Author(s): M.Takahashi, N.Minakawa, A.Matsuda
  • Organizer: Joint Symposium of the 18th International Roundtable on Nucleosides, Nucleotides and Nucleic Acids and the 35^<th> International Symposium on Nucleic Acids Chemistry.
  • Place of Presentation: Kyoto
• [Presentation] Synthesis and properties of oligonucleotides containing 4'-selenoribonucleosides. (2008)
  • Author(s): Y.Inagaki, N.Minakawa, A.Matsuda
  • Organizer: Joint Symposium of the 18^<th> International Roundtable on Nucleosides, Nucleotides and Nucleic Acids and the 35^<th> International Symposium on Nucleic Acids Chemistry.
  • Place of Presentation: Kyoto, Japan
• [Remarks] ホームページ
  • URL: http://www.ph.tokushima-u.ac.jp/article/0018464.html