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NTA-Cholesterol Analogue for the Nongenetic Liquid-Ordered Phase-Specific Functionalization of Lipid Membranes with Proteins

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    NTA-Cholesterol Analogue for the Nongenetic Liquid-Ordered Phase-Specific Functionalization of Lipid Membranes with Proteins
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    • Yanjun Zheng
      Yanjun Zheng
      University of Münster, Institute of Physiological Chemistry and Pathobiochemistry, Münster 48149, Germany
      More by Yanjun Zheng
    • Tristan Wegner
      Tristan Wegner
      University of Münster, Institute of Organic Chemistry, Münster 48149, Germany
      More by Tristan Wegner
    • Daniele Di Iorio
      Daniele Di Iorio
      University of Münster, Institute of Physiological Chemistry and Pathobiochemistry, Münster 48149, Germany
      More by Daniele Di Iorio
    • Marco Pierau
      Marco Pierau
      University of Münster, Institute of Organic Chemistry, Münster 48149, Germany
      More by Marco Pierau
    • Frank Glorius*
      Frank Glorius
      University of Münster, Institute of Organic Chemistry, Münster 48149, Germany
      *Email: [email protected]
      More by Frank Glorius
      Orcidhttps://orcid.org/0000-0002-0648-956X
    • Seraphine V. Wegner*
      Seraphine V. Wegner
      University of Münster, Institute of Physiological Chemistry and Pathobiochemistry, Münster 48149, Germany
      *Email: [email protected]
      More by Seraphine V. Wegner
      Orcidhttps://orcid.org/0000-0002-9072-0858
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    ACS Chemical Biology

    Cite this: ACS Chem. Biol. 2023, 18, 6, 1435–1443
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    https://doi.org/10.1021/acschembio.3c00180
    Published May 15, 2023
    Copyright © 2023 The Authors. Published by American Chemical Society
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    Abstract

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    The nongenetic modification of cell membranes with proteins is a straightforward way of cellular engineering. In these processes, it is important to specifically address the proteins to liquid-ordered (Lo) or liquid-disordered (Ld) domains as this can largely affect their biological functions. Herein, we report a cholesterol analogue (CHIM) with a nitrilotriacetic acid (NTA) headgroup, named CHIM-NTA. CHIM-NTA integrates into lipid membranes similar to the widely used phospholipid-derived DGS–NTA and, when loaded with Ni2+, allows for specific membrane immobilization of any polyhistidine-tagged proteins of choice. Yet, unlike DGS–NTA, it localizes to the Lo phase in phase-separated giant unilamellar vesicles (GUVs) and allows addressing His-tagged proteins to Lo domains. Furthermore, CHIM-NTA readily integrates into the membranes of live cells and thus enables the nongenetic modification of the cell surface with proteins. Overall, CHIM-NTA provides a facile and flexible way to modify biological membranes, in particular Lo domains, with His-tagged proteins and can serve as a broadly applicable molecular tool for cell surface engineering.

    Copyright © 2023 The Authors. Published by American Chemical Society

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    Supporting Information

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acschembio.3c00180.

    • Additional text with details on materials and experimental sections (including materials, synthesis of CHIM-NTA, small unilamellar vesicle (SUV) preparation, cell culture and cell viability experiment) as well as additional results (including 1H NMR spectrum, 13C NMR spectrum of compounds, QCM-D, FRAP, and cell labeling results of the control group) (PDF)

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    This article is cited by 7 publications.

    1. Marco Pierau, Simon Kriegler, Clara Rickhoff, Tiffany O. Paulisch, Tristan Wegner, Azadeh Alavizargar, Andreas Heuer, Roland Winter, Frank Glorius. Neutral Imidazole Lipid Analogues Exhibit Improved Properties for Artificial Model Biomembranes. Langmuir 2025, 41 (17) , 10991-11002. https://doi.org/10.1021/acs.langmuir.5c00478
    2. Po-Hsun Brian Chen, Xiang-Ling Li, Jeremy M. Baskin. Synthetic Lipid Biology. Chemical Reviews 2025, 125 (4) , 2502-2560. https://doi.org/10.1021/acs.chemrev.4c00761
    3. Constanze Schultz, Tristan Wegner, Corinna Heusel, Tim Gallagher, Yanjun Zheng, Markus Werner, Seraphine V. Wegner, Tobias Meyer-Zedler, Oliver Werz, Michael Schmitt, Juergen Popp, Frank Glorius. Alkyne-tagged imidazolium-based membrane cholesterol analogs for Raman imaging applications. Chemical Science 2024, 15 (35) , 14323-14335. https://doi.org/10.1039/D4SC03155E
    4. Antonio Benedetto. Ionic liquids meet lipid bilayers: a state-of-the-art review. Biophysical Reviews 2023, 15 (6) , 1909-1939. https://doi.org/10.1007/s12551-023-01173-3
    5. He Yang, Lihua Yao, Yichen Wang, Gaojian Chen, Hong Chen. Advancing cell surface modification in mammalian cells with synthetic molecules. Chemical Science 2023, 14 (46) , 13325-13345. https://doi.org/10.1039/D3SC04597H
    6. Ran Wang, Yingjie Yu, Meiyu Gai, Ana Mateos Maroto, Svenja Morsbach, Xiang Xia, Maomao He, Jiangli Fan, Xiaojun Peng, Katharina Landfester, Shuai Jiang, Wen Sun. Liposomale Enzym‐Nanoreaktoren auf Basis von Nanoconfinement für eine effiziente Anti‐Tumor‐Therapie. Angewandte Chemie 2023, 135 (44) https://doi.org/10.1002/ange.202308761
    7. Ran Wang, Yingjie Yu, Meiyu Gai, Ana Mateos‐Maroto, Svenja Morsbach, Xiang Xia, Maomao He, Jiangli Fan, Xiaojun Peng, Katharina Landfester, Shuai Jiang, Wen Sun. Liposomal Enzyme Nanoreactors Based on Nanoconfinement for Efficient Antitumor Therapy. Angewandte Chemie International Edition 2023, 62 (44) https://doi.org/10.1002/anie.202308761
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    ACS Chemical Biology

    Cite this: ACS Chem. Biol. 2023, 18, 6, 1435–1443
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acschembio.3c00180
    Published May 15, 2023
    Copyright © 2023 The Authors. Published by American Chemical Society
    Request reuse permissions

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