Development of nucleic acid antibody with ADCC activity

• Project/Area Number: 22659020
• Research Category: Grant-in-Aid for Challenging Exploratory Research
• Allocation Type: Single-year Grants
• Research Field: Drug development chemistry
• Research Institution: Hokkaido University
• Principal Investigator: ICHIKAWA Satoshi 北海道大学, 大学院・薬学研究院, 准教授 (60333621)
• Project Period (FY): 2010 – 2011
• Project Status: Completed (Fiscal Year 2011)
• Budget Amount: ¥3,120,000 (Direct Cost: ¥2,700,000、Indirect Cost: ¥420,000); Fiscal Year 2011: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000); Fiscal Year 2010: ¥1,300,000 (Direct Cost: ¥1,300,000)
• Keywords: 有機化学 / 抗がん / 天然物 / 核酸抗体 / 抗がん剤 / 核酸医薬 / 全合成 / 有機合成化学

Research Abstract

First total synthesis of quinaldopeptin has been accomplished via solid-phase peptide synthesis. Namely, the linear decapeptide was sequentially cyclized and attached by chromophores to give quinaldopeptin. It was revealed that quinaldopeptin binds to double-stranded DNA with high affinity. Finally, quinaldopeptin was installed to the double-stranded DNA to afford a nucleic acid antibody with ADCC activity.

Research Products

• [Journal Article] Total Synthesis and Biological Evaluation of Pacidamycin D and Its 3'-Hydroxy Analogue (2012)
  • Author(s): Okamoto, Kazuya ; Sakagami, Masahiro ; Feng, Fei ; Togame, Hiroko ; Takemoto, Hiroshi ; Ichikawa, Satoshi; Matsuda Akira
  • Journal Title: J. Org. Chem. Volume: 77 Issue: 3 Pages: 1367-1377
  • DOI: 10.1021/jo202159q
  • Peer Reviewed
• [Journal Article] Development of the Carboxamide Protecting Group, 4-(tert-Butyldimethylsiloxy)-2-methoxybenzyl (2011)
  • Author(s): Muranaka, Kazuhiro; Ichikawa, Satoshi; and Matsuda, Akira
  • Journal Title: J. Org. Chem. Volume: 6 Issue: 22 Pages: 9278-9293
  • DOI: 10.1021/jo201495w
  • Peer Reviewed
• [Journal Article] Total Synthesis of Pacidamycin D by Cu(I)-Catalyzed Oxy Enamide Formation (2011)
  • Author(s): Okamoto, Kazuya ; Sakagami, Masahiro ; Feng, Fei ; Togame, Hiroko ; Takemoto, Hiroshi ; Ichikawa, Satoshi ; Matsuda Akira
  • Journal Title: Org. Lett. Volume: 13 Issue: 19 Pages: 5240-5243
  • DOI: 10.1021/ol202124b
  • Peer Reviewed
• [Journal Article] Mechanistic Analysis of Muraymycin Analogues : A Guide to the Design of MraY Inhibitors (2011)
  • Author(s): T.Tanino, B.Al-Dabbagh, D.Mengin-Lecreulx, A.Bouhss, H.Oyama, S.Ichikawa, A.Matsuda
  • Journal Title: The Journal of Medecinal Chemistry Volume: 54 Issue: 24 Pages: 8421-8439
  • DOI: 10.1021/jm200906r
  • Peer Reviewed
• [Journal Article] Synthesis of L-epi-Capreomycidine Derivatives via C-H Amination (2011)
  • Author(s): T.Tanino, S.Ichikawa, A.Matsuda
  • Journal Title: Organic Letter Volume: 13 Issue: 15 Pages: 4028-4031
  • DOI: 10.1021/ol201527k
  • Peer Reviewed
• [Journal Article] Structural Feature of DNA Recognized by HMGB1 (2011)
  • Author(s): Furuita, Kyoko ; Murata, Shunpei ; Jee, Jun Goo ; Ichikawa, Satoshi ; Matsuda, Akira ; Kojima, Chojiro
  • Journal Title: J. Am. Chem. Soc Volume: 133 Issue: 15 Pages: 5788-5790
  • DOI: 10.1021/ja2013399
  • Peer Reviewed
• [Journal Article] Comprehensive Synthetic Study of Muraymycins toward the Development of Novel Antibacterial Agents (2011)
  • Author(s): Ichikawa, S.; Tanino, T.; Ii, K.; Matsuda, A.
  • Journal Title: YAKUGAKU ZASSHI Volume: 131 Issue: 3 Pages: 335-346
  • DOI: 10.1248/yakushi.131.335
  • NAID: 130000678894
  • ISSN: 0031-6903, 1347-5231
  • Peer Reviewed
• [Journal Article] Synthesis and Evaluation of 5-Substituted 9-Hydroxypyrrolo[ 3, 4-c] carbazole-1, 3(2H, 6H)-diones as Check Point 1 Kinase Inhibitors (2010)
  • Author(s): Sako, Yuki ; Osada, Akiko ; Ichikawa, Satoshi; Matsuda, Akira
  • Journal Title: Bioorg. Med. Chem Volume: 18 Issue: 22 Pages: 7878-7889
  • DOI: 10.1016/j.bmc.2010.09.042
  • Peer Reviewed
• [Journal Article] Efficient Synthesis of Hsp90 Inhibitor Dimers as Potential Antitumor Agents (2010)
  • Author(s): Sekiguchi, Hironori ; Muranaka, Kazuhiro ; Osada, Akiko ; Ichikawa, Satoshi; Matsuda, Akira
  • Journal Title: Bioorg. Med. Chem Volume: 18 Issue: 15 Pages: 7732-5737
  • DOI: 10.1016/j.bmc.2010.05.075
  • Peer Reviewed
• [Journal Article] Synthesis and Biological Evaluation of Muraymycin Analogues as Potential Anti-Drug-Resistant Bacterial (2010)
  • Author(s): Tanino, Tetsuya ; Ichikawa, Satoshi; Al-Dabbagh, Bayan ; Bouhss, Ahmed ; Matsuda, Akira
  • Journal Title: ACS Med. Chem. Lett Volume: 1 Issue: 6 Pages: 258-262
  • DOI: 10.1021/ml100057z
  • Peer Reviewed
• [Journal Article] Function-oriented Synthesis of Simplified Caprazamycins : Discovery of Oxazolidine-containing Uridine Derivatives as Antibacterial Agents against Drug-resistant Bacteria (2010)
  • Author(s): Ii, Kensuke ; Ichikawa, Satoshi; Al-Dabbagh, Bayan ; Bouhss, Ahmed ; Matsuda, Akira
  • Journal Title: J. Med. Chem Volume: 53 Issue: 9 Pages: 3793-3813
  • DOI: 10.1021/jm100243n
  • Peer Reviewed
• [Journal Article] A new ASST-type sulfotransferase involved in liponucleoside antibiotic biosynthesis in Streptomycetes (2010)
  • Author(s): Kaysser, Leonard ; Eitel, Kornelia ; Tanino, Tetsuya ; Siebenberg, Stefanie ; Matsuda, Akira ; Ichikawa, Satoshi ; Gust, Bertolt
  • Journal Title: J. Biol. Chem Volume: 285 Issue: 17 Pages: 12684-12694
  • DOI: 10.1074/jbc.m109.094490
  • Peer Reviewed
• [Journal Article] Total Synthesis of(・)-Muraymycin D2 and Its Epimer (2010)
  • Author(s): Tanino, Tetsuya ; Ichikawa, Satoshi; Shiro, Motoo ; Matsuda, Akira
  • Journal Title: J. Org. Chem Volume: 75 Issue: 5 Pages: 1366-1377
  • DOI: 10.1021/jo9027193
  • Peer Reviewed
• [Journal Article] Synthesis and Evaluation of 5-Substituted 9-Hydroxypyrrolo[3, 4-c]carbazole-1, 3(2H, 6H)-diones as Check Point 1 Kinase Inhibitors. (2010)
  • Author(s): Sako, Yuki, Osada, Akiko, Ichikawa, Satoshi, Matsuda, Akira
  • Journal Title: Bioorg.Med.Chem. Volume: 18 Pages: 7878-7889
  • Peer Reviewed
• [Journal Article] Efficient Synthesis of Hsp90 Inhibitor Dimers as Potential Antitumor Agents. (2010)
  • Author(s): Sekiguchi, Hironori, Muranaka, Kazuhiro, Osada, Akiko, Ichikawa, Satoshi, Matsuda, Akira.
  • Journal Title: Bioorg.Med.Chem. Volume: 18 Pages: 7732-5737
  • Peer Reviewed
• [Journal Article] Synthesis and Biological Evaluation of Muraymycin Analogues as Potential Anti-Drug-Resistant Bacterial. (2010)
  • Author(s): Tanino, Tetsuya, Ichikawa, Satoshi, Al-Dabbagh, Bayan, Bouhss, Ahmed, Matsuda, Akira.
  • Journal Title: ACS Med.Chem.Lett. Volume: 1 Pages: 258-262
  • Peer Reviewed
• [Journal Article] Function-oriented Synthesis of Simplified Caprazamycins : Discovery of Oxazolidine-containing Uridine Derivatives as Antibacterial Agents against Drug-resistant Bacteria. (2010)
  • Author(s): Ii, Kensuke, Ichikawa, Satoshi, Al-Dabbagh, Bayan, Bouhss, Ahmed, Matsuda, Akira.
  • Journal Title: J.Med.Chem. Volume: 53 Pages: 3793-3813
  • Peer Reviewed
• [Journal Article] A new ASST-type sulfotransferase involved in liponucleoside antibiotic biosynthesis in Streptomycetes. (2010)
  • Author(s): Kaysser, Leonard, Eitel, Kornelia, Tanino, Tetsuya, Siebenberg, Stefanie, Matsuda, Akira, Ichikawa, Satoshi, Gust, Bertolt.
  • Journal Title: J.Biol.Chem. Volume: 285 Pages: 12684-12694
  • Peer Reviewed
• [Journal Article] Total Synthesis of (-)-Muraymycin D2 and Its Epimer. (2010)
  • Author(s): Tanino, Tetsuya, Ichikawa, Satoshi, Shiro, Motoo, Matsuda, Akira.
  • Journal Title: J.Org.Chem. Volume: 75 Pages: 1366-1377
  • Peer Reviewed
• [Presentation] 抗腫瘍活性天然物キナルドペプチンの構造活性相関研究 (2012)
  • Author(s): 岡村拓也、市川聡、松田彰
  • Organizer: 日本薬学会第132年会
  • Place of Presentation: 北海道大学(札幌)
  • Year and Date: 2012-03-31
• [Presentation] ジアステレオ選択的なUgi反応を用いたサンドラマイシンの全合成研究 (2012)
  • Author(s): 片山勝史、市川聡、松田彰
  • Organizer: 日本薬学会第132年会
  • Place of Presentation: 北海道大学(札幌)
  • Year and Date: 2012-03-31
• [Presentation] プロテアソーム阻害活性を有するシルバクチン類の合成研究 (2012)
  • Author(s): 千葉拓也、市川聡、松田彰
  • Organizer: 日本薬学会第132年会
  • Place of Presentation: 北海道大学(札幌)
  • Year and Date: 2012-03-31
• [Presentation] 新規抗菌剤の開発を指向した天然物の単純化プロセス (2012)
  • Author(s): 市川聡
  • Organizer: 日本薬学会第132年会
  • Place of Presentation: 北海道大学(札幌)
  • Year and Date: 2012-03-31
• [Presentation] 抗菌剤開発を指向したイソキサゾリジン環を有するウリジン誘導体の設計・合成 (2012)
  • Author(s): 山口繭美、市川聡、松田彰
  • Organizer: 日本薬学会第132年会
  • Place of Presentation: 北海道大学(札幌)
  • Year and Date: 2012-03-29
• [Presentation] プロテアソーム阻害活性を有するシルバクチン類の合成研究 (2011)
  • Author(s): 千葉拓也、市川聡、松田彰
  • Organizer: 日本薬学会北海道支部例会第137例会
  • Place of Presentation: 北海道大学(札幌)
  • Year and Date: 2011-12-03
• [Presentation] Development of Antibacterial Agents Active against Drug Resistant Bacteria Based on Natural Products (2011)
  • Author(s): 市川聡、松田彰
  • Organizer: AIMECS11 8th AFMC International Medicinal Chemistry
  • Place of Presentation: Keio Plaza Hotel(Tokyo)
  • Year and Date: 2011-12-01
• [Presentation] Development of Antibacterial Agents Active against Drug Resistant Bacteria Based on Natural Products (2011)
  • Author(s): Ichikawa, S.; Matsuda, A.
  • Organizer: AIMECS11 8th AFMC International Medicinal Chemistry Symposium
  • Place of Presentation: Keio Plaza Hotel (Tokyo)
  • Year and Date: 2011-12-01
• [Presentation] Synthesis and Biological Evaluation of Caprazamycin Analogues (2011)
  • Author(s): Lee, S.-H.; Ichikawa, S.; Matsuda, A.
  • Organizer: AIMECS11 8th AFMC International Medicinal Chemistry Symposium
  • Place of Presentation: Keio Plaza Hotel (Tokyo)
  • Year and Date: 2011-12-01
• [Presentation] Total Synthesis of Pacidamycin D by Cu(I)-Catalyzed Oxyenamide Formation (2011)
  • Author(s): Okamoto, K.; Sakagami, M.; Feng, F.; Togame, H.; Takemoto, H.; Ichikawa, S.; Matsuda, A.
  • Organizer: AIMECS11 8th AFMC International Medicinal Chemistry Symposium
  • Place of Presentation: Keio Plaza Hotel (Tokyo)
  • Year and Date: 2011-12-01
• [Presentation] 抗腫瘍活性環状ペプチドサンドラマイシンの合成研究 (2011)
  • Author(s): 片山勝史、市川聡、松田彰
  • Organizer: 第53回天然有機化合物討論会
  • Place of Presentation: 大阪国際交流センター(大阪)
  • Year and Date: 2011-09-29
• [Presentation] サンドラマイシン誘導体の合成研究 (2011)
  • Author(s): 片山勝史、市川聡、松田彰
  • Organizer: 第23回万有札幌シンポジウム
  • Place of Presentation: 北海道大学(札幌)
  • Year and Date: 2011-07-02
• [Presentation] 新規カルボキサミド保護基4-(tert-butyldimethylsiloxy)-2-methoxybenzyl(SiMB)基の開発と環化促進補助基としての応用 (2011)
  • Author(s): 村中一大、市川聡、松田彰
  • Organizer: 第9回次世代を担う有機化学シンポジウム
  • Place of Presentation: 日本薬学会長井記念館(東京都)
  • Year and Date: 2011-05-01
• [Presentation] Comprehensive synthetic study of muraymycins toward the development of novel antibiotics (2010)
  • Author(s): 谷野哲也、市川聡、松田彰
  • Organizer: The International Chemical Congress of Pacific Basin Societies-Pacifichem 2010
  • Place of Presentation: ハワイ(アメリカ)
  • Year and Date: 2010-12-18
• [Presentation] Function-oriented synthesis of caprazamycins as antibacterial agents active against drug-resistant bacteria (2010)
  • Author(s): 谷野哲也、市川聡、松田彰
  • Organizer: IRT 2010-XIX International Round Table on Nucleosides, Nucleotides and Nucleic Acids
  • Place of Presentation: リヨン(フランス)
  • Year and Date: 2010-09-02
• [Presentation] 抗菌抗生物質ムライマイシンの脂質部誘導体の構造活性相関研究 (2010)
  • Author(s): 谷野哲也、市川聡、松田彰
  • Organizer: 日本薬学会北海道支部例会第134例会
  • Place of Presentation: 札幌
  • Year and Date: 2010-05-08
• [Remarks]
  • URL: http://www.pharm.hokudai.ac.jp/yakka/Matsuda_Lab/Matsuda_Lab_Home.html
• [Remarks]