ACS Publications. Most Trusted. Most Cited. Most Read
My Activity
CONTENT TYPES

Light-Controlled Lipid Interaction and Membrane Organization in Photolipid Bilayer Vesicles

  • Patrick Urban
    Patrick Urban
    Photonics and Optoelectronics Group, Department of Physics and CeNS, Ludwig-Maximilians-Universität München, Amalienstraße 54, 80799 Munich, Germany
  • Stefanie D. Pritzl
    Stefanie D. Pritzl
    Photonics and Optoelectronics Group, Department of Physics and CeNS, Ludwig-Maximilians-Universität München, Amalienstraße 54, 80799 Munich, Germany
  • David B. Konrad
    David B. Konrad
    Department of Chemistry and Center for Integrated Protein Science, Ludwig-Maximilians-Universität München, Butenandtstraße 5-13, 81377 Munich, Germany
  • James A. Frank
    James A. Frank
    Department of Chemistry and Center for Integrated Protein Science, Ludwig-Maximilians-Universität München, Butenandtstraße 5-13, 81377 Munich, Germany
  • Carla Pernpeintner
    Carla Pernpeintner
    Photonics and Optoelectronics Group, Department of Physics and CeNS, Ludwig-Maximilians-Universität München, Amalienstraße 54, 80799 Munich, Germany
    Nanosystems Initiative Munich, Schellingstraße 4, 80799 Munich, Germany
  • Christian R. Roeske
    Christian R. Roeske
    Photonics and Optoelectronics Group, Department of Physics and CeNS, Ludwig-Maximilians-Universität München, Amalienstraße 54, 80799 Munich, Germany
  • Dirk Trauner*
    Dirk Trauner
    Department of Chemistry and Center for Integrated Protein Science, Ludwig-Maximilians-Universität München, Butenandtstraße 5-13, 81377 Munich, Germany
    Department of Chemistry, New York University, Silver Center, 100 Washington Square East, Room 712, New York 10003, United States
    Nanosystems Initiative Munich, Schellingstraße 4, 80799 Munich, Germany
    *E-mail: [email protected] (D.T.).
    More by Dirk Trauner
  • , and 
  • Theobald Lohmüller*
    Theobald Lohmüller
    Photonics and Optoelectronics Group, Department of Physics and CeNS, Ludwig-Maximilians-Universität München, Amalienstraße 54, 80799 Munich, Germany
    Nanosystems Initiative Munich, Schellingstraße 4, 80799 Munich, Germany
    *E-mail: [email protected] (T.L.).
Cite this: Langmuir 2018, 34, 44, 13368–13374
Publication Date (Web):October 10, 2018
https://doi.org/10.1021/acs.langmuir.8b03241
Copyright © 2018 American Chemical Society

    Article Views

    2753

    Altmetric

    -

    Citations

    LEARN ABOUT THESE METRICS
    Other access options
    Supporting Info (2)»

    Abstract

    Abstract Image

    Controlling lateral interactions between lipid molecules in a bilayer membrane to guide membrane organization and domain formation is a key factor for studying and emulating membrane functionality in synthetic biological systems. Here, we demonstrate an approach to reversibly control lipid organization, domain formation, and membrane stiffness of phospholipid bilayer membranes using the photoswitchable phospholipid azo-PC. azo-PC contains an azobenzene group in the sn2 acyl chain that undergoes reversible photoisomerization on illumination with UV-A and visible light. We demonstrate that the concentration of the photolipid molecules and also the assembly and disassembly of photolipids into lipid domains can be monitored by UV–vis spectroscopy because of a blue shift induced by photolipid aggregation.

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.

    Recommended

    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. You can change your affiliated institution below.

    Supporting Information

    ARTICLE SECTIONS
    Jump To

    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.langmuir.8b03241.

    • Switching of membrane domains in GUVs containing DPhPC, azo-PC, and cholesterol and fusion of small domains to form large domains over the course of seconds (MPG)

    • Experimental details for bending rigidity measurements, for the chemical synthesis, and additional data (PDF)

    Terms & Conditions

    Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    This article is cited by 46 publications.

    1. Arash Manafirad, Cintia A. Menendez, Gustavo R. Perez-Lemus, S. Thayumanavan, Juan J. de Pablo, Anthony D. Dinsmore. Structural and Mechanical Response of Two-Component Photoswitchable Lipid Bilayer Vesicles. Langmuir 2023, 39 (45) , 15932-15941. https://doi.org/10.1021/acs.langmuir.3c01764
    2. Adrian Müller-Deku, Oliver Thorn-Seshold. Exhaustive Catalytic ortho-Alkoxylation of Azobenzenes: Flexible Access to Functionally Diverse Yellow-Light-Responsive Photoswitches. The Journal of Organic Chemistry 2022, 87 (24) , 16526-16531. https://doi.org/10.1021/acs.joc.2c02214
    3. Jie Hu, Di Wu, Qingqing Pan, Hanmei Li, Jing Zhang, Fang Geng. Recent Development of Photoresponsive Liposomes Based on Organic Photosensitizers, Au Nanoparticles, and Azobenzene Derivatives for Nanomedicine. ACS Applied Nano Materials 2022, 5 (10) , 14171-14190. https://doi.org/10.1021/acsanm.2c03167
    4. Stefanie D. Pritzl, Johannes Morstein, Sophia Kahler, David B. Konrad, Dirk Trauner, Theobald Lohmüller. Postsynthetic Photocontrol of Giant Liposomes via Fusion-Based Photolipid Doping. Langmuir 2022, 38 (39) , 11941-11949. https://doi.org/10.1021/acs.langmuir.2c01685
    5. Athanasios Papangelis, Trond Ulven. Synthesis of Lysophosphatidylcholine and Mixed Phosphatidylcholine. The Journal of Organic Chemistry 2022, 87 (12) , 8194-8197. https://doi.org/10.1021/acs.joc.2c00335
    6. Stefanie D. Pritzl, David B. Konrad, Martina F. Ober, Alexander F. Richter, James A. Frank, Bert Nickel, Dirk Trauner, Theobald Lohmüller. Optical Membrane Control with Red Light Enabled by Red-Shifted Photolipids. Langmuir 2022, 38 (1) , 385-393. https://doi.org/10.1021/acs.langmuir.1c02745
    7. Yuebao Zhang, Changzhen Sun, Chang Wang, Katarina E. Jankovic, Yizhou Dong. Lipids and Lipid Derivatives for RNA Delivery. Chemical Reviews 2021, 121 (20) , 12181-12277. https://doi.org/10.1021/acs.chemrev.1c00244
    8. Reika Tei, Johannes Morstein, Andrej Shemet, Dirk Trauner, Jeremy M. Baskin. Optical Control of Phosphatidic Acid Signaling. ACS Central Science 2021, 7 (7) , 1205-1215. https://doi.org/10.1021/acscentsci.1c00444
    9. Mahmoudreza Doroudgar, Johannes Morstein, Johanna Becker-Baldus, Dirk Trauner, Clemens Glaubitz. How Photoswitchable Lipids Affect the Order and Dynamics of Lipid Bilayers and Embedded Proteins. Journal of the American Chemical Society 2021, 143 (25) , 9515-9528. https://doi.org/10.1021/jacs.1c03524
    10. James A. Frank, Marc-Joseph Antonini, Po-Han Chiang, Andres Canales, David B. Konrad, Indie C. Garwood, Gabriela Rajic, Florian Koehler, Yoel Fink, Polina Anikeeva. In Vivo Photopharmacology Enabled by Multifunctional Fibers. ACS Chemical Neuroscience 2020, 11 (22) , 3802-3813. https://doi.org/10.1021/acschemneuro.0c00577
    11. Stefanie D. Pritzl, Patrick Urban, Alexander Prasselsperger, David B. Konrad, James A. Frank, Dirk Trauner, Theobald Lohmüller. Photolipid Bilayer Permeability is Controlled by Transient Pore Formation. Langmuir 2020, 36 (45) , 13509-13515. https://doi.org/10.1021/acs.langmuir.0c02229
    12. Patrick Urban, Stefanie D. Pritzl, Martina F. Ober, Christina F. Dirscherl, Carla Pernpeintner, David B. Konrad, James A. Frank, Dirk Trauner, Bert Nickel, Theobald Lohmueller. A Lipid Photoswitch Controls Fluidity in Supported Bilayer Membranes. Langmuir 2020, 36 (10) , 2629-2634. https://doi.org/10.1021/acs.langmuir.9b02942
    13. Carlos A. Z. Bassetto, Juergen Pfeffermann, Rohit Yadav, Simon Strassgschwandtner, Toma Glasnov, Francisco Bezanilla, Peter Pohl. Photolipid excitation triggers depolarizing optocapacitive currents and action potentials. Nature Communications 2024, 15 (1) https://doi.org/10.1038/s41467-024-45403-y
    14. Smita Pawar, Prashant Pingale, Atul Garkal, Riyaz Ali M. Osmani, Kavita Gajbhiye, Madhur Kulkarni, Krutika Pardeshi, Tejal Mehta, Amarjitsing Rajput. Unlocking the potential of nanocarrier-mediated mRNA delivery across diverse biomedical frontiers: A comprehensive review. International Journal of Biological Macromolecules 2024, 267 , 131139. https://doi.org/10.1016/j.ijbiomac.2024.131139
    15. Agustín Mangiarotti, Mina Aleksanyan, Macarena Siri, Tsu‐Wang Sun, Reinhard Lipowsky, Rumiana Dimova. Photoswitchable Endocytosis of Biomolecular Condensates in Giant Vesicles. Advanced Science 2024, 14 https://doi.org/10.1002/advs.202309864
    16. Yusuf Qutbuddin, Ainoa Guinart, Svetozar Gavrilović, Kareem Al Nahas, Ben L. Feringa, Petra Schwille. Light‐Activated Synthetic Rotary Motors in Lipid Membranes Induce Shape Changes Through Membrane Expansion. Advanced Materials 2024, 36 (16) https://doi.org/10.1002/adma.202311176
    17. Jinhua Zhang, Francis Schuknecht, Ludwig Habermann, Alexander Pattis, Jonathan Heine, Stefanie D. Pritzl, Dirk Trauner, Theobald Lohmüller. Label‐Free Time‐Resolved Monitoring of Photolipid Bilayer Isomerization by Plasmonic Sensing. Advanced Optical Materials 2024, 12 https://doi.org/10.1002/adom.202302266
    18. Andre Berndt, Denise Cai, Adam Cohen, Barbara Juarez, Jaume Taura Iglesias, Hejian Xiong, Zhenpeng Qin, Lin Tian, Paul A. Slesinger. Current Status and Future Strategies for Advancing Functional Circuit Mapping In Vivo. The Journal of Neuroscience 2023, 43 (45) , 7587-7598. https://doi.org/10.1523/JNEUROSCI.1391-23.2023
    19. Mina Aleksanyan, Andrea Grafmüller, Fucsia Crea, Vasil N. Georgiev, Naresh Yandrapalli, Stephan Block, Joachim Heberle, Rumiana Dimova. Photomanipulation of Minimal Synthetic Cells: Area Increase, Softening, and Interleaflet Coupling of Membrane Models Doped with Azobenzene‐Lipid Photoswitches. Advanced Science 2023, 10 (31) https://doi.org/10.1002/advs.202304336
    20. Larissa Socrier, Claudia Steinem. Photo‐Lipids: Light‐Sensitive Nano‐Switches to Control Membrane Properties. ChemPlusChem 2023, 88 (11) https://doi.org/10.1002/cplu.202300203
    21. Yujia Zhang, Jorin Riexinger, Xingyun Yang, Ellina Mikhailova, Yongcheng Jin, Linna Zhou, Hagan Bayley. A microscale soft ionic power source modulates neuronal network activity. Nature 2023, 620 (7976) , 1001-1006. https://doi.org/10.1038/s41586-023-06295-y
    22. Nina Hartrampf, Samuel M. Leitao, Nils Winter, Henry Toombs-Ruane, James A. Frank, Petra Schwille, Dirk Trauner, Henri G. Franquelim. Structural diversity of photoswitchable sphingolipids for optodynamic control of lipid microdomains. Biophysical Journal 2023, 122 (11) , 2325-2341. https://doi.org/10.1016/j.bpj.2023.02.029
    23. Naofumi Shimokawa, Tsutomu Hamada. Physical Concept to Explain the Regulation of Lipid Membrane Phase Separation under Isothermal Conditions. Life 2023, 13 (5) , 1105. https://doi.org/10.3390/life13051105
    24. Long Zheng, Qian Song, Peng Tan, Sheng‐Tao Wang, Xiao‐Qin Liu, Lin‐Bing Sun. Endowing Covalent Organic Frameworks with Photoresponsive Active Sites for Controllable Propylene Adsorption. Small 2023, 19 (15) https://doi.org/10.1002/smll.202207291
    25. Tailise Carolina de Souza‐Guerreiro, Gaia Bondelli, Iago Grobas, Stefano Donini, Valentina Sesti, Chiara Bertarelli, Guglielmo Lanzani, Munehiro Asally, Giuseppe Maria Paternò. Membrane Targeted Azobenzene Drives Optical Modulation of Bacterial Membrane Potential. Advanced Science 2023, 10 (8) https://doi.org/10.1002/advs.202205007
    26. Larissa Socrier, Somayeh Ahadi, Mathias Bosse, Cindy Montag, Daniel B. Werz, Claudia Steinem. Optical Manipulation of Gb 3 Enriched Lipid Domains: Impact of Isomerization on Gb 3 ‐Shiga Toxin B Interaction. Chemistry – A European Journal 2023, 29 (4) https://doi.org/10.1002/chem.202202766
    27. Hejian Xiong, Kevin A. Alberto, Jonghae Youn, Jaume Taura, Johannes Morstein, Xiuying Li, Yang Wang, Dirk Trauner, Paul A. Slesinger, Steven O. Nielsen, Zhenpeng Qin. Optical control of neuronal activities with photoswitchable nanovesicles. Nano Research 2023, 16 (1) , 1033-1041. https://doi.org/10.1007/s12274-022-4853-x
    28. Tristan Wegner, Ranjini Laskar, Frank Glorius. Lipid mimetics: A versatile toolbox for lipid biology and beyond. Current Opinion in Chemical Biology 2022, 71 , 102209. https://doi.org/10.1016/j.cbpa.2022.102209
    29. Fucsia Crea, Antreas Vorkas, Aoife Redlich, Rubén Cruz, Chaowei Shi, Dirk Trauner, Adam Lange, Ramona Schlesinger, Joachim Heberle. Photoactivation of a Mechanosensitive Channel. Frontiers in Molecular Biosciences 2022, 9 https://doi.org/10.3389/fmolb.2022.905306
    30. Federico Baserga, Antreas Vorkas, Fucsia Crea, Luiz Schubert, Jheng-Liang Chen, Aoife Redlich, Mariafrancesca La Greca, Julian Storm, Sabine Oldemeyer, Kirsten Hoffmann, Ramona Schlesinger, Joachim Heberle. Membrane Protein Activity Induces Specific Molecular Changes in Nanodiscs Monitored by FTIR Difference Spectroscopy. Frontiers in Molecular Biosciences 2022, 9 https://doi.org/10.3389/fmolb.2022.915328
    31. Hazel Erkan-Candag, Denis Krivic, Mathias A. F. Gsell, Mina Aleksanyan, Thomas Stockner, Rumiana Dimova, Oleksandra Tiapko, Klaus Groschner. Characterization of DAG Binding to TRPC Channels by Target-Dependent cis–trans Isomerization of OptoDArG. Biomolecules 2022, 12 (6) , 799. https://doi.org/10.3390/biom12060799
    32. Martina F. Ober, Adrian Müller-Deku, Anna Baptist, Benjamin Ajanović, Heinz Amenitsch, Oliver Thorn-Seshold, Bert Nickel. SAXS measurements of azobenzene lipid vesicles reveal buffer-dependent photoswitching and quantitative Z→E isomerisation by X-rays. Nanophotonics 2022, 11 (10) , 2361-2368. https://doi.org/10.1515/nanoph-2022-0053
    33. J. Royes, V.A. Bjørnestad, G. Brun, T. Narayanan, R. Lund, C. Tribet. Transition kinetics of mixed lipid:photosurfactant assemblies studied by time-resolved small angle X-ray scattering. Journal of Colloid and Interface Science 2022, 610 , 830-841. https://doi.org/10.1016/j.jcis.2021.11.133
    34. Johannes Morstein, Dirk Trauner. Optical Control of Glycerolipids and Sphingolipids. CHIMIA 2021, 75 (12) , 1022. https://doi.org/10.2533/chimia.2021.1022
    35. Juergen Pfeffermann, Barbara Eicher, Danila Boytsov, Christof Hannesschlaeger, Timur R. Galimzyanov, Toma N. Glasnov, Georg Pabst, Sergey A. Akimov, Peter Pohl. Photoswitching of model ion channels in lipid bilayers. Journal of Photochemistry and Photobiology B: Biology 2021, 224 , 112320. https://doi.org/10.1016/j.jphotobiol.2021.112320
    36. Alexander Sailer, Joyce C. M. Meiring, Constanze Heise, Linda N. Pettersson, Anna Akhmanova, Julia Thorn‐Seshold, Oliver Thorn‐Seshold. Pyrrole Hemithioindigo Antimitotics with Near‐Quantitative Bidirectional Photoswitching that Photocontrol Cellular Microtubule Dynamics with Single‐Cell Precision**. Angewandte Chemie 2021, 133 (44) , 23888-23897. https://doi.org/10.1002/ange.202104794
    37. Alexander Sailer, Joyce C. M. Meiring, Constanze Heise, Linda N. Pettersson, Anna Akhmanova, Julia Thorn‐Seshold, Oliver Thorn‐Seshold. Pyrrole Hemithioindigo Antimitotics with Near‐Quantitative Bidirectional Photoswitching that Photocontrol Cellular Microtubule Dynamics with Single‐Cell Precision**. Angewandte Chemie International Edition 2021, 60 (44) , 23695-23704. https://doi.org/10.1002/anie.202104794
    38. Li Gao, Joyce C.M. Meiring, Yvonne Kraus, Maximilian Wranik, Tobias Weinert, Stefanie D. Pritzl, Rebekkah Bingham, Evangelia Ntouliou, Klara I. Jansen, Natacha Olieric, Jörg Standfuss, Lukas C. Kapitein, Theobald Lohmüller, Julia Ahlfeld, Anna Akhmanova, Michel O. Steinmetz, Oliver Thorn-Seshold. A Robust, GFP-Orthogonal Photoswitchable Inhibitor Scaffold Extends Optical Control over the Microtubule Cytoskeleton. Cell Chemical Biology 2021, 28 (2) , 228-241.e6. https://doi.org/10.1016/j.chembiol.2020.11.007
    39. Johannes Morstein, Anna C. Impastato, Dirk Trauner. Photoswitchable Lipids. ChemBioChem 2021, 22 (1) , 73-83. https://doi.org/10.1002/cbic.202000449
    40. Dirk Leifert, Alex S. Moreland, Jakkarin Limwongyut, Alexander A. Mikhailovsky, Guillermo C. Bazan. Photoswitchable Conjugated Oligoelectrolytes for a Light‐Induced Change of Membrane Morphology. Angewandte Chemie 2020, 132 (46) , 20513-20517. https://doi.org/10.1002/ange.202004448
    41. Dirk Leifert, Alex S. Moreland, Jakkarin Limwongyut, Alexander A. Mikhailovsky, Guillermo C. Bazan. Photoswitchable Conjugated Oligoelectrolytes for a Light‐Induced Change of Membrane Morphology. Angewandte Chemie International Edition 2020, 59 (46) , 20333-20337. https://doi.org/10.1002/anie.202004448
    42. Oskar Klaja, James A. Frank, Dirk Trauner, Ana‐Nicoleta Bondar. Potential energy function for a photo‐switchable lipid molecule. Journal of Computational Chemistry 2020, 41 (27) , 2336-2351. https://doi.org/10.1002/jcc.26387
    43. Zubao Gan, Melissa P. Lokugamage, Marine Z. C. Hatit, David Loughrey, Kalina Paunovska, Manaka Sato, Ana Cristian, James E. Dahlman. Nanoparticles containing constrained phospholipids deliver mRNA to liver immune cells in vivo without targeting ligands. Bioengineering & Translational Medicine 2020, 5 (3) https://doi.org/10.1002/btm2.10161
    44. Rui Li, Takahiro Muraoka, Kazushi Kinbara. Thermo-driven self-assembly of a PEG-containing amphiphile in a bilayer membrane. RSC Advances 2020, 10 (43) , 25758-25762. https://doi.org/10.1039/D0RA03920A
    45. Ignacio Insua, Javier Montenegro. Synthetic Supramolecular Systems in Life-like Materials and Protocell Models. Chem 2020, 6 (7) , 1652-1682. https://doi.org/10.1016/j.chempr.2020.06.005
    46. Sofia Municoy, María I. Álvarez Echazú, Pablo E. Antezana, Juan M. Galdopórpora, Christian Olivetti, Andrea M. Mebert, María L. Foglia, María V. Tuttolomondo, Gisela S. Alvarez, John G. Hardy, Martin F. Desimone. Stimuli-Responsive Materials for Tissue Engineering and Drug Delivery. International Journal of Molecular Sciences 2020, 21 (13) , 4724. https://doi.org/10.3390/ijms21134724

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    You’ve supercharged your research process with ACS and Mendeley!

    STEP 1:
    Click to create an ACS ID

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    MENDELEY PAIRING EXPIRED
    Your Mendeley pairing has expired. Please reconnect