Selective Recognition of Biomolecules by Molecular Capsules

• Project/Area Number: 16K13947
• Research Category: Grant-in-Aid for Challenging Exploratory Research
• Allocation Type: Multi-year Fund
• Research Field: Organic chemistry
• Research Institution: Tokyo Institute of Technology
• Principal Investigator: Yoshizawa Michito 東京工業大学, 科学技術創成研究院, 准教授 (70372399)
• Project Period (FY): 2016-04-01 – 2018-03-31
• Project Status: Completed (Fiscal Year 2017)
• Budget Amount: ¥3,640,000 (Direct Cost: ¥2,800,000、Indirect Cost: ¥840,000); Fiscal Year 2017: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000); Fiscal Year 2016: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
• Keywords: 金属 / 芳香環 / 分子カプセル / 生体分子 / 糖 / スクロース / 分子間相互作用 / 内包 / 蛍光 / 超分子化学

Outline of Final Research Achievements

Selective recognition of saccharides by artificial receptors in water is a challenging goal due to their strong hydrophilicities and complex molecular structures with subtle regio- and stereochemical differences. Here we report the selective and efficient encapsulation of D-sucrose within a coordination-driven molecular capsule from natural saccharide mixtures in water (~100% selectivity and >85% yield). Unlike previous artificial receptors and natural receptors that rely on multiple hydrogen-bonding interactions, theoretical calculations and control experiments indicate that the observed unique selectivity arises frommultiple CH-pi interactions between the sucrose hydrocarbon backbone and the shape-complementary polyaromatic cavity (~1 nm in diameter) of the capsule.

Research Products

• [Journal Article] Exact mass analysis of sulfur clusters upon encapsulation by a polyaromatic capsular matrix (2017)
  • Author(s): Matsuno Sho、Yamashina Masahiro、Sei Yoshihisa、Akita Munetaka、Kuzume Akiyoshi、Yamamoto Kimihisa、Yoshizawa Michito
  • Journal Title: Nature Communications Volume: 8 Issue: 1 Pages: 749-749
  • DOI: 10.1038/s41467-017-00605-5
  • Peer Reviewed / Open Access
• [Journal Article] A polyaromatic nanocapsule as a sucrose receptor in water (2017)
  • Author(s): Masahiro Yamashina, Munetaka Akita, Taisuke Hasegawa, Shigehiko Hayashi, and Michito Yoshizawa*
  • Journal Title: Science Advances Volume: 3 Issue: 8
  • DOI: 10.1126/sciadv.1701126
  • Peer Reviewed / Open Access
• [Journal Article] A Switchable Open/closed Polyaromatic Macrocycle that Shows Reversible Binding of Long Hydrophilic Molecules (2017)
  • Author(s): Kurihara Kohei、Yazaki Kohei、Akita Munetaka、Yoshizawa Michito
  • Journal Title: Angewandte Chemie International Edition Volume: 56 Issue: 38 Pages: 11360-11364
  • DOI: 10.1002/anie.201703357
  • Peer Reviewed
• [Journal Article] Polyaromatic molecular peanuts (2017)
  • Author(s): Yazaki Kohei、Akita Munetaka、Prusty Soumyakanta、Chand Dillip Kumar、Kikuchi Takashi、Sato Hiroyasu、Yoshizawa Michito
  • Journal Title: Nature Communications Volume: 8 Issue: 1 Pages: 15914-15914
  • DOI: 10.1038/ncomms15914
  • Peer Reviewed / Open Access / Int'l Joint Research
• [Journal Article] A Polyaromatic Molecular Clip That Enables the Binding of Planar, Tubular, and Dendritic Compounds (2017)
  • Author(s): Jono Keisuke、Suzuki Akira、Akita Munetaka、Albrecht Ken、Yamamoto Kimihisa、Yoshizawa Michito
  • Journal Title: Angewandte Chemie International Edition Volume: 56 Issue: 13 Pages: 3570-3574
  • DOI: 10.1002/anie.201612489
  • Peer Reviewed
• [Journal Article] An M2L4 Molecular Capsule with a Redox Switchable Polyradical Shell (2016)
  • Author(s): Kohei Yazaki, Shogo Noda, Yuya Tanaka, Yoshihisa Sei, Munetaka Akita, Michito Yoshizawa
  • Journal Title: Angew. Chem. Int. Ed. Volume: 55 Issue: 48 Pages: 15031-15034
  • DOI: 10.1002/anie.201608350
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Polycationic-Shelled Capsular and Tubular Nanostructures and Their Anionic-Guest Binding Properties (2016)
  • Author(s): Kohei Yazaki, Yoshihisa Sei, Munetaka Akita, Michito Yoshizawa
  • Journal Title: Chem. Eur. J. Volume: 22 Issue: 49 Pages: 17557-17561
  • DOI: 10.1002/chem.201604384
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Recognition of Multiple Methyl Groups on Aromatic Rings by a Polyaromatic Cavity (2016)
  • Author(s): Masahiro Yamashina, Sho Matsuno, Yoshihisa Sei, Munetaka Akita, Michito Yoshizawa
  • Journal Title: Chem. Eur. J. Volume: 22 Issue: 40 Pages: 14147-14150
  • DOI: 10.1002/chem.201603032
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] M2L4 Coordination Capsules with Tunable Anticancer Activities upon Guest Encapsulation (2016)
  • Author(s): Anife Ahmedova, Rositsa Mihaylova, Denitsa Momekova, Pavletta Shestakova, Silviya Stoykova, Joana Zaharieva, Masahiro Yamashina, Georgi Momekov, Munetaka Akita, Michito Yoshizawa
  • Journal Title: Dalton Trans. Volume: 45 Issue: 33 Pages: 13214-13221
  • DOI: 10.1039/c6dt01801g
  • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
• [Journal Article] A Fluorescent Molecular Capsule with a Flexible Polyaromatic Shell for Detecting Monoterpene Compounds in Water (2016)
  • Author(s): A. Suzuki, K. Kondo, Y. Sei, M. Akita, M. Yoshizawa
  • Journal Title: Chemical Communications Volume: 52 Issue: 15 Pages: 3151-3154
  • DOI: 10.1039/c5cc09647b
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Anticancer Potencies of Pt(II)- and Pd(II)-linked M2L4 Coordination Capsules with Improved Selectivity (2016)
  • Author(s): Anife Ahmedova, Denitsa Momekova, Masahiro Yamashina, Pavletta Shestakova, Georgi Momekov, Munetaka Akita, Michito Yoshizawa
  • Journal Title: Chem. Asian J. Volume: 11 Issue: 4 Pages: 474-477
  • DOI: 10.1002/asia.201501238
  • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
• [Presentation] アントラセン環を有する金属架橋カプセル : 環状硫黄の顕著な安定化 (2017)
  • Author(s): 〇松野 匠、山科雅裕、吉沢道人、穐田宗隆
  • Organizer: 日本化学会 第97春季年会
  • Place of Presentation: 慶應義塾大学 日吉キャンパス（神奈川県横浜市）
  • Year and Date: 2017-03-16
• [Presentation] アントラセン環を有する金属架橋カプセル：水中でのオリゴ乳酸の内包 (2017)
  • Author(s): 〇草葉竣介、山科雅裕、吉沢道人、穐田宗隆
  • Organizer: 日本化学会 第97春季年会
  • Place of Presentation: 慶應義塾大学 日吉キャンパス（神奈川県横浜市）
  • Year and Date: 2017-03-16
• [Presentation] Self-assembly of Peanut-shaped Polyaromatic Compounds (2017)
  • Author(s): 〇K. Yazaki, T. Kikuchi, H, Sato, S. Prusty, D. K. Chand, M. Yoshizawa, M. Akita
  • Organizer: 日本化学会 第97春季年会
  • Place of Presentation: 慶應義塾大学 日吉キャンパス（神奈川県横浜市）
  • Year and Date: 2017-03-16
• [Presentation] An Anthracene-Shelled Coordination Capsule: Selective Encapsulation of Disaccharide in Water (2017)
  • Author(s): 〇M. Yamashina, M. Yoshizawa, M. Akita
  • Organizer: 日本化学会 第97春季年会
  • Place of Presentation: 慶應義塾大学 日吉キャンパス（神奈川県横浜市）
  • Year and Date: 2017-03-16
• [Presentation] 芳香環ミセル -便利な分子フラスコの開発を目指して- (2017)
  • Author(s): 吉沢道人
  • Organizer: 第11回 東海支部若手研究者フォーラム
  • Invited
• [Presentation] 多環芳香族ナノ空間のデザイン：アントラセンは便利な分子部品？ (2017)
  • Author(s): 吉沢道人
  • Organizer: 第3回 「高次複合光応答」若手の会
  • Invited
• [Presentation] Selective Encapsulation of D-Sucrose by a Polyaromatic Capsule in Water (2017)
  • Author(s): M. Yamashina, M. Akita, M. Yoshizawa
  • Organizer: International Symposium on Macrocyclic and Supramolecular Chemistry (ISMSC 2017)
• [Presentation] Anthracene‐based Supramolecular Capsules: Unusual Host Capabilities in Water (2017)
  • Author(s): M. Yoshizawa
  • Organizer: International Symposium on Pure & Applied Chemistry
  • Invited
• [Presentation] Anthracene-based Supramolecular Nanostructures (2017)
  • Author(s): M. Yoshizawa
  • Organizer: 10th China-Japan Joint Symposium on Functional Supramolecular Architectures
  • Invited
• [Presentation] ncapsulation of Sulfur Clusters by An Anthracene-shelled Coordination Capsule (2016)
  • Author(s): 〇S. Matsuno, M. Yamashina, M. Yoshizawa, M. Akita
  • Organizer: 第26回日本MRS年次大会
  • Place of Presentation: 横浜情報文化センター（神奈川県横浜市）
  • Year and Date: 2016-12-19
• [Presentation] 窒素を含む多環芳香族ナノ空間の構築 (2016)
  • Author(s): 吉沢道人
  • Organizer: エキゾチック自己組織化材料・金属と分子集合 合同シンポジウム
  • Place of Presentation: 温泉旅館丸茂（鳥取県鳥取市）
  • Year and Date: 2016-11-23
• [Presentation] アントラセン環を有する金属架橋カプセルによる環状硫黄の内包と安定化 (2016)
  • Author(s): 〇松野 匠、山科雅裕、吉沢道人、穐田宗隆
  • Organizer: 第6回CSJ化学フェスタ
  • Place of Presentation: タワーホール船堀（東京都江戸川区）
  • Year and Date: 2016-11-14
• [Presentation] Encapsulation of Metallo-Porphyrins and Metallo-Phthalocyanines within Polyaromatic Capsules in Water (2016)
  • Author(s): 吉沢道人
  • Organizer: 第66回錯体化学討論会
  • Place of Presentation: 福岡大学 七隈キャンパス（福岡県福岡市）
  • Year and Date: 2016-09-10
  • Invited
• [Presentation] アントラセン環に囲まれた疎水性ナノ空間による親水性オリゴマーの包接 (2016)
  • Author(s): 〇山科雅裕・吉沢道人・穐田宗隆
  • Organizer: 第27回基礎有機化学討論会
  • Place of Presentation: 広島国際会議場(広島県広島市）
  • Year and Date: 2016-09-01
• [Presentation] Methyl-Group Recognition on Aromatic Rings by an Anthracene-Shelled Coordination Capsule (2016)
  • Author(s): 〇S. Matsuno, M. Yamashina, Y. Sei, M. Akita, M. Yoshizawa
  • Organizer: International Symposium on Macrocyclic and Supramolecular Chemistry
  • Place of Presentation: The K-Hotel Seoul（韓国）
  • Year and Date: 2016-07-10
  • Int'l Joint Research
• [Presentation] An Anthracene-Shelled Coordination Capsule: Preparation of Fluorescent Host-Guest Complexes with Tunable Color (2016)
  • Author(s): 〇M. Yamashina, Y. Sei, M. Akita, M. Yoshizawa
  • Organizer: International Symposium on Macrocyclic and Supramolecular Chemistry
  • Place of Presentation: The K-Hotel Seoul（韓国）
  • Year and Date: 2016-07-10
  • Int'l Joint Research
• [Presentation] Preparation and Host Properties of Capsular and Tubular Nanostructures with Polycationic Shells (2016)
  • Author(s): 〇K. Yazaki, Y. Sei, M. Akita, M. Yoshizawa
  • Organizer: International Symposium on Macrocyclic and Supramolecular Chemistry
  • Place of Presentation: The K-Hotel Seoul（韓国）
  • Year and Date: 2016-07-10
  • Int'l Joint Research
• [Presentation] Pairwise Encapsulation of Fluorescent Dyes within an Anthracene-Shelled Coordination Capsule (2016)
  • Author(s): 〇M. Yamashina, Y. Sei, M. Akita, M. Yoshizawa
  • Organizer: Fluorescent Biomolecules and their Building Blocks - Design and Applications (FB3)
  • Place of Presentation: Tianjin University（中国）
  • Year and Date: 2016-07-07
  • Int'l Joint Research
• [Presentation] A Polycationic Molecular Capsule Bearing Acridinium Panels and the Anionic-Guest Binding Properties (2016)
  • Author(s): 〇K. Yazaki, Y. Sei, M. Akita, M. Yoshizawa
  • Organizer: Fluorescent Biomolecules and their Building Blocks - Design and Applications (FB3)
  • Place of Presentation: Tianjin University（中国）
  • Year and Date: 2016-07-07
  • Int'l Joint Research
• [Presentation] アントラセン環を有する金属架橋カプセルを用いた親水性オリゴマーの包接挙動 (2016)
  • Author(s): 〇山科雅裕、吉沢道人、穐田宗隆
  • Organizer: 第14回ホスト・ゲスト化学シンポジウム
  • Place of Presentation: 高知城ホール（高知県高知市）
  • Year and Date: 2016-06-04
• [Presentation] Polyaromatic micelles as water-soluble soft molecular containers (2016)
  • Author(s): 吉沢道人
  • Organizer: WRHI International Workshop on Advanced Laser Spectroscopy for Soft Molecular Systems
  • Place of Presentation: 東京工業大学 すずかけ台キャンパス(神奈川県横浜市）
  • Invited
• [Presentation] Polyaromatic-Shelled Coordination Capsules Displaying Unique Host-Guest Interactions (2016)
  • Author(s): 吉沢道人
  • Organizer: Royal Society of Chemistry, Inorganic Chemistry Symposium
  • Place of Presentation: 東京工業大学 大岡山キャンパス（東京都目黒区）
• [Remarks] 穐田・吉沢研究室ホームページ
  • URL: http://www.res.titech.ac.jp/~smart/smartj.html