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2016 Fiscal Year Annual Research Report

N-heterocyclic carbene-modified gold nanoparticles for biosensing

Research Project

Project/Area Number 26288023
Research InstitutionNagoya University

Principal Investigator

CRUDDEN Cathleen  名古屋大学, トランスフォーマティブ生命分子研究所, 客員教授 (10721029)

Project Period (FY) 2014-04-01 – 2018-03-31
KeywordsNano Material / Gold Nanoparticles / N-Heterocyclic Carbene / Bio-imaging / Stability / Photoacoustic Properties
Outline of Annual Research Achievements

This year we have made substantial progress in the area of NHC-stabilized nanoparticles. Our first publication appeared in Angewandte Chemie International Edition. This paper detailed our study of carboxylated NHCs as ligands for the preparation of water soluble gold nanoparticles. These nanoparticles were extensively studied and could be analyzed by polyacrylamide gel electrophoresis due to their charged nature. In basic pHs, the nanoparticles were exceptionally stable, however they aggregated under acidic pH. This aggregation was shown to be reversible. The NHC-stabilized nanoparticles were stable under a variety of biologically-relevant conditions, except thiol stability was still sub optimal. In addition to the synthetic and stability studies, in collaboration with the Yamaguchi group, we were able to test the photoacoustic properties of these nanoparticles. The nanoparticles were shown to have a linear response and even the smallest nanoparticles had a reasonable photoacoustic response.
In more recent work, we have prepared a new type of bidentate NHC, one that has a single NHC ligand and a thiol ligand on the same molecule. This compound was shown to make Au(1) nanoclusters when exposed to molecular gold, and to make highly stable nanoparticles when exposed to auric acid and reducing agents. In this work, we have prepared the first NHC-based nanoparticle that is stable to exogenous thiol. This work is very preliminary and will continue in the next funding year.

Current Status of Research Progress
Current Status of Research Progress

1: Research has progressed more than it was originally planned.

Reason

The use of bidentate NHCs to stabilize nanoparticles has proven to be an excellent strategy and we believe will be the key to employing these nanoparticles in vivo. Synthetic issues in the previous year were overcome this year, permitting us to make two of the important structures that we needed to make, namely bidentate alkylated NHCs and bidentate NHC/thiol ligands. Both of these ligands turned out to be excellent supporting ligands for gold nanoparticles.
In addition to solving synthetic issues with regards to the preparation of the ligands, we were also able to analyze the water soluble nanoparticles with the assistance of the Itami and Higashiyama group at the Institute of Transformative Bio-Molecules.

Strategy for Future Research Activity

Future work will focus on three areas:
(1) Completion of work on mixed thiol/NHC ligands and nanoparticles. The stability of these nanoparticles will be studied in more depth and the use of various linker lengths and nanoparticle sizes will be studied.
(2) The preparation of larger nanoparticles for a variety of applications will be a focus of this year. In collaboration with the Higashiyama group we will examine micron sized nanostructures for gene delivery and we will also examine more typical 40-50 nm structures for in vivo applications.
(3) Biological applications will also be addressed head on in this year since we now have a variety of sizes and types of water soluble nanoparticles and have the ability to prepare many types of NHC ligands. This will require bioconjugation studies.

Causes of Carryover

新規金属ナノ粒子の合成を遂行する予定であった博士研究員の博士号取得が遅れたことにより雇用が遅れ、研究計画に大幅な遅延が生じたため

Expenditure Plan for Carryover Budget

研究遂行の為の物品費、また研究発表のために使用する。

  • Research Products

    (20 results)

All 2017 2016 Other

All Int'l Joint Research (3 results) Journal Article (8 results) (of which Int'l Joint Research: 4 results,  Peer Reviewed: 8 results,  Acknowledgement Compliant: 1 results,  Open Access: 1 results) Presentation (9 results) (of which Int'l Joint Research: 3 results,  Invited: 6 results)

  • [Int'l Joint Research] クイーンズ大学(カナダ)

    • Country Name
      CANADA
    • Counterpart Institution
      クイーンズ大学
  • [Int'l Joint Research] セント・アンドルーズ大学(英国)

    • Country Name
      UNITED KINGDOM
    • Counterpart Institution
      セント・アンドルーズ大学
  • [Int'l Joint Research]

    • # of Other Countries
      2
  • [Journal Article] Water-Soluble N-Heterocyclic Carbene-Protected Gold Nanoparticles: Size-Controlled Synthesis, Stability, and Optical Properties2017

    • Author(s)
      Kirsi Salorinne, Renee W. Y. Man, Chien-Hung Li, Masayasu Taki, Masakazu Nambo, Cathleen M. Crudden
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 印刷中 Pages: 印刷中

    • DOI

      10.1002/anie.201701605

    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Borocation catalysis2017

    • Author(s)
      Patrick Eisenberger, Cathyleen M. Crudden
    • Journal Title

      Dalton Transactions

      Volume: 46 Pages: 4874-4887

    • DOI

      10.1039/C6DT04232E

    • Peer Reviewed
  • [Journal Article] 2. Development of Versatile Sulfone Electrophiles for Suzuki-Miyaura Cross-Coupling Reactions2017

    • Author(s)
      Masakazu Nambo, Eric C. Keske, Jason P. G. Rygus, Jacky, C.-H. Yim, Cathleen M. Crudden
    • Journal Title

      ACS Catalysis

      Volume: 7 Pages: 1108-1112

    • DOI

      10.1021/acscatal.6b03434

    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Installing Stable Molecular Chirality within the Walls of Periodic Mesoporous Organosilicas via Self-Assembly2016

    • Author(s)
      Lacey M. Reid, Cathleen M. Crudden
    • Journal Title

      Chemistry of Materials

      Volume: 28 Pages: 7605-7612

    • DOI

      10.1021/acs.chemmater.6b02153

    • Peer Reviewed
  • [Journal Article] Simple direct formation of self-assembled N-heterocyclic carbene monolayers on gold and their application in biosensing2016

    • Author(s)
      C. M. Crudden, J. H. Horton, M. R. Narouz, Z. Li, C. A. Smith, K. Munro, C. J. Baddeley, C. R. Larrea, B. Drevniok, B. Thanabalasingam, A. B. McLean, O. V. Zenkina, I. I. Ebralidze, Z. She, H.-B. Kraatz, N. J. Mosey, L. N. Saunders, A. Yagi
    • Journal Title

      Nature Communications

      Volume: 7 Pages: 12654

    • DOI

      10.1038/ncomms12654

    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Chiral carbene-borane adducts: precursors for borenium catalysts for asymmetric FLP hydrogenations2016

    • Author(s)
      Jolie Lam, Benjamin A. R. Gunther, Jeffrey M. Farrell, Patrick Eisenberger, Brian P. Bestvater, Paul D. Newman, Rebecca L. Melen, Cathleen M. Crudden, Douglas W. Stephan
    • Journal Title

      Dalton Transactions

      Volume: 45 Pages: 15303-15316

    • DOI

      10.1039/C6DT02202B

    • Peer Reviewed
  • [Journal Article] Accessible bidentate diol functionality within highly ordered composite periodic mesoporous organosilicas2016

    • Author(s)
      Lacey M. Reid, Gang Wu, Cathleen M. Crudden
    • Journal Title

      New journal of Chemistry

      Volume: 40 Pages: 6487-6497

    • DOI

      10.1039/C6NJ00401F

    • Peer Reviewed
  • [Journal Article] 4. Arylative Desulfonation of Diarylmethyl Phenyl Sulfones with Arenes Catalyzed by Scandium Triflate2016

    • Author(s)
      Masakazu Nambo, Zachary T. Ariki, Daniel Canseco-Gonzalez, D. Dawson Beattie, Cathleen M. Crudden
    • Journal Title

      Organic Letters

      Volume: 18 Pages: 2339-2342

    • DOI

      10.1021/acs.orglett.6b00744

    • Peer Reviewed / Int'l Joint Research
  • [Presentation] Water-soluble N-heterocyclic carbene protected gold nanoparticles for biological applications2017

    • Author(s)
      Kirsi Salorinne, Renee Man, Henry Li, Masayasu Taki, Masakazu Nambo, Cathleen M. Crudden
    • Organizer
      96th CSJ meeting
    • Place of Presentation
      Keio Univeristy
    • Year and Date
      2017-03-17 – 2017-03-17
  • [Presentation] Enhanced stability: Synthesis and characterizations of N-heterocyclic carbene-stabilized gold nanoparticles2017

    • Author(s)
      Renee Man, Henry Li, Masakazu Nambo, Cathleen M. Crudden
    • Organizer
      96th CSJ meeting
    • Place of Presentation
      Keio Univeristy
    • Year and Date
      2017-03-17 – 2017-03-17
  • [Presentation] Organometallic chemistry at the interfaces: Preparation of biologically active molecules using enantiospecific cross coupling and the design of novel carbon-based monolayers on gold2016

    • Author(s)
      Cathleen M. Crudden
    • Organizer
      4th International Symposium on New Frontiers in Materials Science
    • Place of Presentation
      Hokkaido, Japan
    • Year and Date
      2016-11-08 – 2016-11-08
    • Int'l Joint Research / Invited
  • [Presentation] Catalysis from Molecules to Materials2016

    • Author(s)
      Cathleen M. Crudden
    • Organizer
      Connaught Industry Alliance Symposium
    • Place of Presentation
      Toronto, Canada
    • Year and Date
      2016-10-11 – 2016-10-11
    • Invited
  • [Presentation] New Trends in Organometallic Chemistry leading to Organic Synthesis2016

    • Author(s)
      Cathleen M. Crudden
    • Organizer
      American Chemical Society Conference
    • Place of Presentation
      Philidelphia, United States
    • Year and Date
      2016-08-21 – 2016-08-21
    • Int'l Joint Research / Invited
  • [Presentation] Pd-Catalyzed Sequential Arylation of Methyl Sulfone Derivatives toward Straightforward Synthesis of Multiply-arylated Methanes2016

    • Author(s)
      Masakazu Nambo, Eric, C. Keske, Jason, P. G. Ryugus, Jacky C.-H. Yim, Cathleen M. Crudden
    • Organizer
      Gordon Research Conference, Stereochemistry
    • Place of Presentation
      Boston, United States
    • Year and Date
      2016-07-27 – 2016-07-28
    • Int'l Joint Research
  • [Presentation] Organometallic chemistry for the preparation of biologically important molecules and for the design of novel self assembled monolayers on gold2016

    • Author(s)
      Cathleen M. Crudden
    • Organizer
      Centre in Green Chemistry and Catalysis annual meeting
    • Place of Presentation
      Montreal, Canada
    • Year and Date
      2016-06-03 – 2016-06-03
    • Invited
  • [Presentation] Organometallic chemistry: Surfaces and Catalysts2016

    • Author(s)
      Cathleen M. Crudden
    • Organizer
      IRTG Symposium
    • Place of Presentation
      Muenster, Germany
    • Year and Date
      2016-05-23 – 2016-05-23
    • Invited
  • [Presentation] N-Heterocyclic carbenes as valuable supporting ligands in catalysis: From cross-coupling to borenium catalysis to materials chemistry2016

    • Author(s)
      Cathleen M. Crudden
    • Organizer
      Catalysis Division Conference
    • Place of Presentation
      Ottawa, Canada
    • Year and Date
      2016-05-10 – 2016-05-10
    • Invited

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Published: 2018-01-16  

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