• Search Research Projects
  • Search Researchers
  • How to Use
  1. Back to project page

2016 Fiscal Year Annual Research Report

Investigation of property prediction for pharmaceutical co-crystals using synchrotron radiation based X-ray study

Research Project

Project/Area Number 26460057
Research InstitutionJapan Synchrotron Radiation Research Institute

Principal Investigator

杉本 邦久  公益財団法人高輝度光科学研究センター, 利用研究促進部門, 研究員 (00512807)

Project Period (FY) 2014-04-01 – 2017-03-31
Keywords共結晶体 / 放射光 / 精密構造解析 / 物性予測制御
Outline of Annual Research Achievements

Caffeine-Oxalic acid及びCaffeine-Malonic acidの共結晶体の単結晶をそれぞれ合成し、SPring-8の単結晶構造解析ビームラインBL02B1で超高分解X線回折データを観測した。これらのデータは、精密構造解析により電子密度分布を可視化し、さらに、静電ポテンシャルの可視化にも成功した。Caffeine-Oxalic acidの共結晶体は、Caffeine分子内のイミダゾール環の窒素とOxalic acidのカルボン酸の水素が水素結合を形成することにより構築されている(N…H-O = 1.81 Å)。一方、電子密度分布解析では、等電子密度面に色づけされたカルボン酸部位を見ると電子は局在化しており、この水素結合は、比較的強い静電相互作用であることが分かる。また、Caffeine-Malonic acidの共結晶体も同様に、Caffeine分子内のイミダゾール環の窒素とMalonic acidのカルボン酸の水素が水素結合を形成することにより構築されている(N…H-O = 1.83 Å)。これらの水素結合距離には、有意な差がないために原子間の距離だけからは判断しにくい。しかしながら、電子密度分布解析では、それぞれのカルボン酸部位を比較すると、Malonic acidのカルボン酸部位の電子がOxalic acidに比べて局在化していないことがわかる。従って、Malonic acidにより構築されるCaffeine共結晶体は、Oxalic acidにより構築されるCaffeine共結晶体に比べて弱い水素結合により構築されていることが示唆される。このような知見は、医薬品共結晶体の溶解度などの物性に深く寄与していると考えられる。今後、精密X線構造解析を用いた電子密度分布の定量化により医薬品共結晶体の物性予測への応用が期待できる。

  • Research Products

    (19 results)

All 2017 2016 Other

All Int'l Joint Research (1 results) Journal Article (13 results) (of which Int'l Joint Research: 2 results,  Peer Reviewed: 13 results,  Acknowledgement Compliant: 2 results,  Open Access: 1 results) Presentation (4 results) (of which Int'l Joint Research: 2 results) Remarks (1 results)

  • [Int'l Joint Research] オーフス大学(デンマーク)

    • Country Name
      DENMARK
    • Counterpart Institution
      オーフス大学
  • [Journal Article] Structural characterization of caffeine-oxalic acid co-crystals from the powder diffraction pattern at the SPring-8 BL02B2 beamline2017

    • Author(s)
      K. Sugimoto, S. Kawaguchi, M. Takemoto
    • Journal Title

      Powder Diff.

      Volume: 印刷中 Pages: -

    • DOI

      https://doi.org/10.1017/S088571561700032X

    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Mixed-Valence Nickel Bis(azamacrocycle) Compounds with Ghost-Leg-type Sheets2017

    • Author(s)
      R. Hashiguchi, K. Otsubo, M. Maesato, K. Sugimoto, A. Fujiwara, H. Kitagawa
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 56 Pages: 3838-3841

    • DOI

      10.1002/anie.201610515

    • Peer Reviewed
  • [Journal Article] Electronic perturbation of supramolecular conjugates of porphyrins and phthalocyanines2017

    • Author(s)
      N. Mihara, Y. Yamada, S. Akine, K. Sugimoto, K. Tanaka
    • Journal Title

      Chem. Commun.

      Volume: 53 Pages: 2230

    • DOI

      10.1039/c6cc09590a

    • Peer Reviewed
  • [Journal Article] Physical properties and crystal structure analysis of double-perovskite NdBaMn2O6 by using single crystals2017

    • Author(s)
      S. Yamada, H. Sagayama, K. Higuchi, T. Sasaki, K. Sugimoto, T. Arima
    • Journal Title

      Phys. Rev. B

      Volume: 95 Pages: 035101

    • DOI

      10.1103/PhysRevB.95.035101

    • Peer Reviewed
  • [Journal Article] An Electrically Conductive Single-Component Donor-Acceptor-Donor Aggregate with Hydrogen-Bonding Lattice2016

    • Author(s)
      M. Hayashi, K. Otsubo, M. Maesato, T. Komatsu, K. Sugimoto, A. Fujiwara, H. Kitagawa
    • Journal Title

      Inorg. Chem.

      Volume: 55 Pages: 13027-13034

    • DOI

      10.7566/JPSJ.85.094605

    • Peer Reviewed
  • [Journal Article] Carrier concentration dependence of structural disorder in thermoelectric Sn1-xTe2016

    • Author(s)
      M. Sist, E. M. J. Hedegaard, S. Christensen, N. Bindzus, K. F. F. Fischer, H. Kasai, K. Sugimoto, B. B. Iversen
    • Journal Title

      IUCrJ

      Volume: 2 Pages: 377-388

    • DOI

      10.1107/S2052252516012707

    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Time-resolved crystal structure analysis of resonantly vibrating langasite oscillator2016

    • Author(s)
      S. Aoyagi, H. Osawa, K. Sugimoto, S. Takeda, C. Moriyoshi, Y. Kuroiwa
    • Journal Title

      Jpn., J. Appl. Phys.

      Volume: 55 Pages: 10TC05

    • DOI

      10.7567/JJAP.55.10TC05

    • Peer Reviewed
  • [Journal Article] Structurally Diverse Polynuclear Copper(I) Complexes Bridged by Pyrimidine-, Pyrazine-, and Triazine- based Ligands with Several 2-Pyridyl Groups2016

    • Author(s)
      M. Maekawa, K. Sugimoto, T. Okubo, T. Kuroda-Sowa, M. Munakata
    • Journal Title

      ChemistrySelect

      Volume: 1 Pages: 3812-3822

    • DOI

      10.1002/slct.201600791

    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Bis(dipyrrinato)zinc(II) Complexes: Emission in the Solid State2016

    • Author(s)
      M. Tsuchiya, R. Sakamoto, M. Shimada, Y. Yamanoi, Y. Hattori, K. Sugimoto, E. Nishibori, H. Nishihara
    • Journal Title

      Inorg. Chem.

      Volume: 55 Pages: 5732-5734

    • DOI

      10.1021/acs.inorgchem.6b00431

    • Peer Reviewed
  • [Journal Article] First-Order Structural Change Accompanied by Yb Valence Transition in YbInCu42016

    • Author(s)
      S. Tsutsui, K. Sugimoto, R. Tsunoda, Y. Hirose, T. Mito, R. Settai, M. Mizumaki
    • Journal Title

      J. Phys. Soc. Jpn.

      Volume: 85 Pages: 063602

    • DOI

      10.7566/JPSJ.85.063602

    • Peer Reviewed
  • [Journal Article] Ultrafine Metal-Organic Right Square Prism Shaped Nanowires2016

    • Author(s)
      KI. Otake, K. Osubo, K. Sugimoto, A. Fujiwara, H. Kitagawa
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 55 Pages: 6448-6451

    • DOI

      10.1002/anie.201601678

    • Peer Reviewed
  • [Journal Article] Correlation of superconductivity with crystal structure in (NH3)yCsxFeSe2016

    • Author(s)
      L. Zheng, X. Miao, Y. Sakai, H. Goto, E. Uesugi, R. Eguchi, S. Nishiyama, K. Sugimoto, A. Fujiwara, Y. Kubozono
    • Journal Title

      Phys. Rev. B

      Volume: 93 Pages: 104508

    • DOI

      10.1103/PhysRevB.93.104508

    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Neutral-Type One-Dimensional Mixed-Valence Halogen-Bridged Platinum Chain Complexes with Large Charge-Transfer Band Gaps2016

    • Author(s)
      K. Otake, K. Otsubo, K. Sugimoto, A. Fujiwara, H. Kitagawa
    • Journal Title

      Inorg. Chem.

      Volume: 55 Pages: 2620-2626

    • DOI

      10.1021/acs.inorgchem.5b02980

    • Peer Reviewed
  • [Presentation] Controlled Self-Assembly of a 2-D Sheet Coordination Polymer and Monomer Containing Eight-Membered Cu4I4 Ring Crown Motif2016

    • Author(s)
      Kunihisa Sugimoto, Masahiko Maekawa, Takayoshi Kuroda-Sowa
    • Organizer
      The 14th Conference of the Asian Crystallographic Association (AsCA2016)
    • Place of Presentation
      Hanoi, Vietnam
    • Year and Date
      2016-12-04 – 2016-12-07
    • Int'l Joint Research
  • [Presentation] 八員環Cu4I4クラウンモチーフを有する金属錯体の結晶構造2016

    • Author(s)
      杉本邦久、前川雅彦、黒田孝義
    • Organizer
      平成28年度日本結晶学会年会
    • Place of Presentation
      茨城県立県民文化センター(茨城県水戸市)
    • Year and Date
      2016-11-17 – 2016-11-18
  • [Presentation] 先端放射光で物質の成り立ちを探究する2016

    • Author(s)
      杉本邦久
    • Organizer
      第6回CSJ化学フェスタ2016
    • Place of Presentation
      タワーホール船堀(東京都江戸川区)
    • Year and Date
      2016-11-14 – 2016-11-16
  • [Presentation] Structural characterization of co-crystal caffeine with dicarboxylic acid from powder diffraction2016

    • Author(s)
      Kunihisa Sugimoto, Syogo Kawaguchi, Michitaka Takemoto
    • Organizer
      15th European Powder Diffraction Conference
    • Place of Presentation
      Bari, Italy
    • Year and Date
      2016-06-12 – 2016-06-15
    • Int'l Joint Research
  • [Remarks] SPring-8/JASRI利用研究促進部門

    • URL

      http://rud.spring8.or.jp/member/0006544.html

URL: 

Published: 2018-01-16  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi