Development of novel caged compounds activatable by single-photon uncaging with longer wavelength light

• Project/Area Number: 25870180
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Multi-year Fund
• Research Field: Physical pharmacy; Bio-related chemistry
• Research Institution: The University of Tokyo
• Principal Investigator: KAMIYA Mako 東京大学, 医学(系)研究科(研究院), 助教 (90596462)
• Project Period (FY): 2013-04-01 – 2015-03-31
• Project Status: Completed (Fiscal Year 2014)
• Budget Amount: ¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000); Fiscal Year 2014: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000); Fiscal Year 2013: ¥2,600,000 (Direct Cost: ¥2,000,000、Indirect Cost: ¥600,000)
• Keywords: ケージド化合物 / BODIPY / 光誘起電子移動

Outline of Final Research Achievements

Caged compounds are useful tools for precise spatiotemporal modulation of cell functions, but in most cases uncaging requires ultraviolet (UV) light, which is cytotoxic and has limited tissue penetration. Therefore, caged compounds that can be activated by longer-wavelength light are required. In this research project, we describe a novel photoelimination reaction of 4-aryloxy boron dipyrromethene (BODIPY) derivatives and show that BODIPY can function as a caging group for phenol groups. We developed a novel BODIPY-caged histamine compound, which is photoactivatable with blue-green visible light to stimulate cultured HeLa cells in a spatiotemporally well-controlled manner. This caging strategy is expected to be widely applicable to develop tools for probing various cellular functions.

Research Products

• [Journal Article] Boron Dipyrromethene as a Fluorescent Caging Group for Single-photon Uncaging with Long-wavelength Visible Light (2014)
  • Author(s): Nobuhiro Umeda, Hironori Takahashi, Mako Kamiya, Tasuku Ueno, Toru Komatsu, Takuya Terai, Kenjiro Hanaoka, Tetsuo Nagano, and Yasuteru Urano
  • Journal Title: ACS Chem. Biol Volume: 9 Issue: 10 Pages: 2242-2246
  • DOI: 10.1021/cb500525p
  • Peer Reviewed
• [Journal Article] Selective Ablation of beta-Galactosidase-expressing Cells with a Rationally Designed Activatable Photosensitizer (2014)
  • Author(s): Yuki Ichikawa, Mako Kamiya, Fumiaki Obata, Masayuki Miura, Takuya Terai, Toru Komatsu, Tasuku Ueno, Kenjiro Hanaoka, Tetsuo Nagano, Yasuteru Urano
  • Journal Title: Angewandte Chemie International Edition Volume: 未定
  • Peer Reviewed
• [Presentation] BODIPYケージド化合物の生物学的応用 (2015)
  • Author(s): 高橋光規，梅田暢大，神谷真子，長野哲雄，浦野泰照
  • Organizer: 日本ケミカルバイオロジー学会 第10回年会
  • Place of Presentation: 東北大学川内キャンパス（宮城県仙台市）
  • Year and Date: 2015-06-10 – 2015-06-12
• [Presentation] BODIPYケージド化合物の生物学的応用 (2014)
  • Author(s): 高橋光規，梅田暢大，神谷真子，長野哲雄，浦野泰照
  • Organizer: 日本顕微鏡学会第７０回記念学術講演会
  • Place of Presentation: 幕張メッセ国際会議場（千葉県千葉市）
  • Year and Date: 2014-05-11
• [Presentation] BODIPYケージド化合物の生物学的応用
  • Author(s): 高橋光規、梅田暢大、神谷真子、長野哲雄、浦野泰照
  • Organizer: 日本薬学会 第134年会
  • Place of Presentation: 熊本大学黒髪キャンパス
• [Presentation] BODIPYケージド化合物の生物学的応用
  • Author(s): 高橋 光規，梅田 暢大，神谷 真子，長野 哲雄，浦 野 泰照
  • Organizer: 日本顕微鏡学会第70回記念学術講演会
  • Place of Presentation: 幕張メッセ