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3D spatial imaging of chirality using nuclear magnetic resonance (NMR)

Research Project

Project/Area Number 19K05229
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Review Section Basic Section 28040:Nanobioscience-related
Research InstitutionNational Institute for Materials Science

Principal Investigator

Labuta Jan  国立研究開発法人物質・材料研究機構, 国際ナノアーキテクトニクス研究拠点, 主任研究員 (00720690)

Project Period (FY) 2019-04-01 – 2023-03-31
Project Status Completed (Fiscal Year 2022)
Budget Amount *help
¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2021: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2020: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2019: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
KeywordsPorphyrin / Chirality / NMR lineshape / Phase Separation / pH-responsiveness / Chemical kinetics / NMR microimaging / pH-responsivness / Microporosity / NMR / Singlet oxygen / Physical chemistry / NMR imaging / NMR/MRI / Sensing / Imaging
Outline of Research at the Start

Chirality is a key feature in many biological events. The two enantiomers of the same molecule differ in interaction within living systems. This is especially important in development of new pharmaceuticals (their effect depends on identity of enantiomer). The purpose of this project is to develop NMR method for chirality mapping based on porphyrin-type molecular detector, which can be used for monitoring of chirality in 3D and in time. Such method will enable to investigate various chiral interconversion processes (e.g. pharmacokinetics, drug metabolism, etc.) in situ or in vivo.

Outline of Final Research Achievements

A series of porphyrin- or oxoporphyrinogen-type compounds were synthesized. Namely, β-functionalized, non-planar N-heterocycle-fused, and star-shaped water-soluble porphyrins. These compounds were studied for their improved anion-binding properties and catalytic activity. Some of the compounds can form porous coordination polymers. These materials are also capable of singlet oxygen generation and therefore are interesting for therapeutic applications, especially photodynamic therapies.
We have developed a method for analytical calculation of NMR spectral exchange lineshapes. The method can be used to analyze molecular kinetics in a wide range of systems, such as host-guest complexes, tautomeric processes, or local molecular rotations. We have also proven that by using a suitable porphyrin-type molecular detector, a sub-millimetre resolution of chiral environment (i.e. enantiomeric excess) can be spatially monitored by NMR microimaging method.

Academic Significance and Societal Importance of the Research Achievements

Most drugs currently in use are chiral compounds. In situ or in vivo chirality imaging would be helpful in drug development. We have shown that the NMR microimaging technique can achieve this using an appropriate molecular detector.

Report

(5 results)
  • 2022 Annual Research Report   Final Research Report ( PDF )
  • 2021 Research-status Report
  • 2020 Research-status Report
  • 2019 Research-status Report
  • Research Products

    (26 results)

All 2023 2022 2021 2020 2019

All Journal Article (15 results) (of which Int'l Joint Research: 15 results,  Peer Reviewed: 15 results,  Open Access: 2 results) Presentation (11 results) (of which Int'l Joint Research: 11 results,  Invited: 7 results)

  • [Journal Article] Persistent microporosity of a non-planar porphyrinoid based on multiple supramolecular interactions for nanomechanical sensor applications2023

    • Author(s)
      Chahal Mandeep K.、Maji Subrata、Liyanage Anuradha、Matsushita Yoshitaka、Tozman Pelin、Payne Daniel T.、Jevasuwan Wipakorn、Fukata Naoki、Karr Paul A.、Labuta Jan、Shrestha Lok Kumar、Ishihara Shinsuke、Ariga Katsuhiko、D’Souza Francis、Yoshikawa Genki、Yamauchi Yusuke、Hill Jonathan P.
    • Journal Title

      Materials Chemistry Frontiers

      Volume: 7 Issue: 2 Pages: 325-332

    • DOI

      10.1039/d2qm01039a

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Analyte Interactions with Oxoporphyrinogen Derivatives: Computational Aspects2022

    • Author(s)
      Hill Jonathan P.、Karr Paul A.、Zuniga Uy Roxanne A.、Subbaiyan Navaneetha K.、Futera Zdenek、Ariga Katsuhiko、Ishihara Shinsuke、Labuta Jan、D’Souza Francis
    • Journal Title

      Current Organic Chemistry

      Volume: 26 Issue: 6 Pages: 580-595

    • DOI

      10.2174/1385272826666220208101325

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] NMR lineshape analysis using analytical solutions of multi-state chemical exchange with applications to kinetics of host-guest systems2022

    • Author(s)
      Brezina Vaclav、Hanykova Lenka、Velychkivska Nadiia、Hill Jonathan P.、Labuta Jan
    • Journal Title

      Scientific Reports

      Volume: 12 Issue: 1 Pages: 1-15

    • DOI

      10.1038/s41598-022-20136-4

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Phase Separation and pH-Dependent Behavior of Four-Arm Star-Shaped Porphyrin-PNIPAM4 Conjugates2022

    • Author(s)
      Velychkivska Nadiia、Sedlacek Ondrej、Shatan Anastasiia B.、Spasovova Monika、Filippov Sergey K.、Chahal Mandeep K.、Janisova Larisa、Brus Jiri、Hanykova Lenka、Hill Jonathan P.、Winnik Francoise M.、Labuta Jan
    • Journal Title

      Macromolecules

      Volume: 55 Issue: 6 Pages: 2109-2122

    • DOI

      10.1021/acs.macromol.1c02188

    • Related Report
      2021 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Molecular rotor based on an oxidized resorcinarene2022

    • Author(s)
      Payne Daniel T.、Labuta Jan、Futera Zdenek、Brezina Vaclav、Hanykova Lenka、Chahal Mandeep K.、Hill Jonathan P.
    • Journal Title

      Organic Chemistry Frontiers

      Volume: 9 Issue: 1 Pages: 39-50

    • DOI

      10.1039/d1qo01479j

    • Related Report
      2021 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Nonionic omnisoluble photosensitizer reference material for the estimation of singlet oxygen quantum yield2022

    • Author(s)
      Payne Daniel T.、Hynek Jan、Labuta Jan、Hill Jonathan P.
    • Journal Title

      Physical Chemistry Chemical Physics

      Volume: 24 Issue: 10 Pages: 6146-6154

    • DOI

      10.1039/d1cp04651a

    • Related Report
      2021 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Estimation of Enantiomeric Excess based on Rapid Host-Guest Exchange2021

    • Author(s)
      Jan Labuta, Shinsuke Ishihara, Daniel T. Payne, Kazuyoshi Takimoto, Hisako Sato, Lenka Hanykova, Katsuhiko Ariga, Jonathan P. Hill
    • Journal Title

      Chemosensors

      Volume: 9 Issue: 9 Pages: 259-259

    • DOI

      10.3390/chemosensors9090259

    • Related Report
      2021 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Dynamics of Meso-Chiral Interconversion in a Butterfly‐Shape Overcrowded Alkene Rotor Tunable by Solvent Properties2021

    • Author(s)
      Kartha Kalathil K.、Takai Atsuro、Futera Zden?k、Labuta Jan、Takeuchi Masayuki
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 60 Issue: 30 Pages: 16466-16471

    • DOI

      10.1002/anie.202102719

    • Related Report
      2021 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Enhancement of singlet oxygen generation based on incorporation of oxoporphyrinogen (OxP) into microporous solids2021

    • Author(s)
      Jan Hynek, Daniel T. Payne, Mandeep K. Chahal, Flavien Sciortino, Yoshitaka Matsushita, Lok Kumar Shrestha, Katsuhiko Ariga, Jan Labuta, Yusuke Yamauchi, Jonathan P. Hill
    • Journal Title

      Material Today Chemistry

      Volume: 21 Pages: 100534-100534

    • DOI

      10.1016/j.mtchem.2021.100534

    • Related Report
      2021 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Enantiomeric Excess Dependent Splitting of NMR Signal through Dynamic Chiral Inversion and Coligand Exchange in a Coordination Complex2020

    • Author(s)
      Kazuyoshi Takimoto, Shinsuke Ishihara, Jan Labuta, Vaclav Brezina, Daniel T. Payne, Jonathan P. Hill, Katsuhiko Ariga, Masato Sumita, Shigeki Mori, Hisako Sato
    • Journal Title

      J. Phys. Chem. Lett.

      Volume: 11 Issue: 19 Pages: 8164-8169

    • DOI

      10.1021/acs.jpclett.0c02284

    • Related Report
      2020 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Molecular Engineering of β-Substituted Oxoporphyrinogens for Hydrogen-Bond Donor Catalysis2020

    • Author(s)
      Mandeep K. Chahal, Daniel T. Payne, Yoshitaka Matsushita, Jan Labuta, Katsuhiko Ariga, Jonathan P. Hill
    • Journal Title

      Eur. J. Org. Chem.

      Volume: - Issue: 1 Pages: 82-90

    • DOI

      10.1002/ejoc.201901706

    • Related Report
      2020 Research-status Report 2019 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] meso-Tetraphenylporphine as a prochiral solvating agent (pro-CSA): A physicochemical study2020

    • Author(s)
      Jan Labuta, Shinsuke Ishihara, Jonathan P. Hill
    • Journal Title

      J. Porphyrins Phthalocyanines

      Volume: 24 Issue: 01n03 Pages: 320-329

    • DOI

      10.1142/s1088424619501141

    • Related Report
      2019 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Diporphyrin tweezer for multichannel spectroscopic analysis of enantiomeric excess2020

    • Author(s)
      Daniel T. Payne, Mandeep K. Chahal, Vaclav Brezina, Whitney A. Webre, Katsuhiko Ariga, Francis D’Souza, Jan Labuta, Jonathan P. Hill
    • Journal Title

      Front. Chem. Sci. Eng.

      Volume: 14 Issue: 1 Pages: 28-40

    • DOI

      10.1007/s11705-019-1869-1

    • Related Report
      2019 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Knock-on synthesis of tritopic calix[4]pyrrole host for enhanced anion interactions2019

    • Author(s)
      Mandeep K. Chahal, Jan Labuta, Vaclav Brezina, Paul A. Karr, Yoshitaka Matsushita, Whitney A. Webre, Daniel T. Payne, Katsuhiko Ariga, Francis D’Souza, Jonathan P. Hill
    • Journal Title

      Dalton Trans.

      Volume: 48 Issue: 41 Pages: 15583-15596

    • DOI

      10.1039/c9dt02365h

    • Related Report
      2019 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Increasing the complexity of oxoporphyrinogen colorimetric sensing chromophores: N-alkylation and β-substitution2019

    • Author(s)
      Mandeep K. Chahal, Nadiia Velychkivska, Whitney A. Webre, Jan Labuta, Shinsuke Ishihara, Katsuhiko Ariga, Francis D’Souza, Jonathan P. Hill
    • Journal Title

      J. Porphyrins Phthalocyanines

      Volume: 23 Issue: 11n12 Pages: 1184-1194

    • DOI

      10.1142/s1088424619501463

    • Related Report
      2019 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Presentation] Phase-Separable and pH-Sensitive Star-Shaped Porphyrin-PNIPAM Conjugates2022

    • Author(s)
      Jan Labuta, Nadiia Velychkivska
    • Organizer
      MANA International Symposium 2022
    • Related Report
      2022 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Physicochemical Analysis of Star-Shaped Porphyrin-PNIPAM4 Conjugates: Phase-Separation and pH-Dependent Phenomena2022

    • Author(s)
      Nadiia Velychkivska, Jan Labuta
    • Organizer
      25th IUPAC Conference on Physical Organic Chemistry (ICPOC25)
    • Related Report
      2022 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Phase Separation and pH-dependent Behavior of Star-Shaped Porphyrin-PNIPAM4 Conjugates2022

    • Author(s)
      Jan Labuta, Nadiia Velychkivska
    • Organizer
      84th Prague Meeting on Macromolecules: Frontiers of Polymers Colloids 2022
    • Related Report
      2022 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Prochiral Solvating Agents (pro-CSA): NMR Detection of Enantiomeric Excess without Formation of Diastereomers2022

    • Author(s)
      Jan Labuta
    • Organizer
      International Conference on Porphyrins and Phthalocyanines (ICPP-12)
    • Related Report
      2022 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Thermal treatment of phase-separable polymers as a possible route to functional porous heterostructures2021

    • Author(s)
      Jan Labuta
    • Organizer
      International Conference on Materials Science and Engineering 2021
    • Related Report
      2021 Research-status Report
    • Int'l Joint Research
  • [Presentation] Phase separation in polymer solutions and gels: thermodynamic theory and experiment2021

    • Author(s)
      Jan Labuta
    • Organizer
      2nd Virtual European Polymer Conference
    • Related Report
      2021 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Porphyrins as Multi-responsive Sensors2019

    • Author(s)
      Jan Labuta
    • Organizer
      MANA International Symposium 2019
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Presentation] Diverse Properties of Porphyrin Derivatives2019

    • Author(s)
      Jan Labuta
    • Organizer
      The 3rd International Workshop on MEMS and Sensor System 2019 (IWMS 2019)
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Multi-responsive Porphyrins for Sensing Applications2019

    • Author(s)
      Jan Labuta
    • Organizer
      The 2019 Spring Meeting of the European Materials Research Society (E-MRS)
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Porphyrins as Multi-responsive Sensors2019

    • Author(s)
      Jan Labuta
    • Organizer
      The 8th Asian Conference on Colloid & Interface Science (ACCIS-2019)
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] From Polymers to Porphyrins and Back Again - My Research Journey in Japan2019

    • Author(s)
      Jan Labuta
    • Organizer
      9th CSJ Chemistry Festa (Chemical Society of Japan)
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research / Invited

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Published: 2019-04-18   Modified: 2024-01-30  

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