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Photoinduced Vesicle Formation via the Copper-Catalyzed Azide–Alkyne Cycloaddition Reaction

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Department of Chemical and Biological Engineering, University of Colorado, 3415 Colorado Avenue, JSC Biotech Building, Boulder, Colorado 80303, United States
Cite this: Langmuir 2016, 32, 32, 8195–8201
Publication Date (Web):July 22, 2016
https://doi.org/10.1021/acs.langmuir.6b02043
Copyright © 2016 American Chemical Society

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    Abstract

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    Synthetic vesicles have a wide range of applications from drug and cosmetic delivery to artificial cell and membrane studies, making simple and controlled formation of vesicles a large focus of the field today. Here, we report the use of the photoinitiated copper-catalyzed azide–alkyne cycloaddition (CuAAC) reaction using visible light to introduce spatiotemporal control into the formation of vesicles. Upon the establishment of the spatiotemporal control over vesicle formation, it became possible to adjust initiation conditions to modulate vesicle sizes resulting in the formation of controllably small or large vesicles based on light intensity or giant vesicles when the formation was initiated in flow-free conditions. Additionally, this photoinitiated method enables vesicle formation at a density 400-fold higher than initiation using sodium ascorbate as the catalyst. Together, these advances enable the formation of high-density, controlled size vesicles using low-energy wavelengths while producing enhanced control over the formation characteristics of the vesicle.

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.langmuir.6b02043.

    • (Left) Mixtures containing alkyne-functionalized lysolipid (2.5 mM), dodecyl azide (2.5 mM), and CAP (1 wt %) showed no formation of triazole phospholipid when left in the dark and (right) same formulation for which CAP was removed and a 20 mW/cm2, 400–500 nm light exposure was applied for 60 min also with no formation of triazole phospholipid (Figure S1), samples containing alkyne-functionalized lysolipid (2.5 mM), dodecyl azide (2.5 mM), CAP (1 wt %), and sulforhodamine (100 μM) were either exposed to 20 mW/cm2, 400–500 nm light for 30 min or were left in the dark (Figure S2), cryo-TEM images of a standard formulation ([alkyne] = [azide] = 2.5 mM, and [CAP] = 1 wt %) exposed to 20 mW/cm2, 400–500 nm light for 30 min (Figure S3), vials containing alkyne-functionalized lysolipid (2.5 mM), dodecyl azide (2.5 mM), and CAP (1 wt %) were exposed to 20 mW/cm2, 400–500 nm light for 10 min (Figure S4), and (left) hypophosphonate salts produced from (right) CAP photoinitiator upon exposure to 400–500 nm light (1) (Figure S5) (PDF)

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    Cited By

    This article is cited by 15 publications.

    1. Tiexin Li, Essam M. Dief, Zlatica Kalužná, Melanie MacGregor, Cina Foroutan-Nejad, Nadim Darwish. On-Surface Azide–Alkyne Cycloaddition Reaction: Does It Click with Ruthenium Catalysts?. Langmuir 2022, 38 (18) , 5532-5541. https://doi.org/10.1021/acs.langmuir.2c00100
    2. Megan L. Qualls, Ruhani Sagar, Jinchao Lou, Michael D. Best. Demolish and Rebuild: Controlling Lipid Self-Assembly toward Triggered Release and Artificial Cells. The Journal of Physical Chemistry B 2021, 125 (47) , 12918-12933. https://doi.org/10.1021/acs.jpcb.1c07406
    3. Gangam Srikanth Kumar, Qing Lin. Light-Triggered Click Chemistry. Chemical Reviews 2021, 121 (12) , 6991-7031. https://doi.org/10.1021/acs.chemrev.0c00799
    4. Benjamin D. Fairbanks, Laura J. Macdougall, Sudheendran Mavila, Jasmine Sinha, Bruce E. Kirkpatrick, Kristi S. Anseth, Christopher N. Bowman. Photoclick Chemistry: A Bright Idea. Chemical Reviews 2021, 121 (12) , 6915-6990. https://doi.org/10.1021/acs.chemrev.0c01212
    5. Takafumi Enomoto, Roberto J. Brea, Ahanjit Bhattacharya, and Neal K. Devaraj . In Situ Lipid Membrane Formation Triggered by Intramolecular Photoinduced Electron Transfer. Langmuir 2018, 34 (3) , 750-755. https://doi.org/10.1021/acs.langmuir.7b02783
    6. Neal K. Devaraj . In Situ Synthesis of Phospholipid Membranes. The Journal of Organic Chemistry 2017, 82 (12) , 5997-6005. https://doi.org/10.1021/acs.joc.7b00604
    7. Amandeep Arora, Kamaljeet Singh. Click Chemistry Mediated by Photochemical Energy. ChemistrySelect 2022, 7 (29) https://doi.org/10.1002/slct.202200541
    8. Mingrui Zhang, Ying Zhang, Wei Mu, Mingdong Dong, Xiaojun Han. In Situ Synthesis of Lipid Analogues Leading to Artificial Cell Growth and Division. ChemSystemsChem 2022, 4 (4) https://doi.org/10.1002/syst.202200007
    9. Kira A. Podolsky, Neal K. Devaraj. Synthesis of lipid membranes for artificial cells. Nature Reviews Chemistry 2021, 5 (10) , 676-694. https://doi.org/10.1038/s41570-021-00303-3
    10. Sidonie Aubert, Marine Bezagu, Alan C. Spivey, Stellios Arseniyadis. Spatial and temporal control of chemical processes. Nature Reviews Chemistry 2019, 3 (12) , 706-722. https://doi.org/10.1038/s41570-019-0139-6
    11. Danielle Konetski, Sudheendran Mavila, Chen Wang, Brady Worrell, Christopher N. Bowman. Production of dynamic lipid bilayers using the reversible thiol–thioester exchange reaction. Chemical Communications 2018, 54 (58) , 8108-8111. https://doi.org/10.1039/C8CC03471K
    12. Danielle Konetski, Austin Baranek, Sudheendran Mavila, Xinpeng Zhang, Christopher N. Bowman. Formation of lipid vesicles in situ utilizing the thiol-Michael reaction. Soft Matter 2018, 14 (37) , 7645-7652. https://doi.org/10.1039/C8SM01329B
    13. Jennifer A. Reeves, Michael L. Allegrezza, Dominik Konkolewicz. Rise and Fall: Poly(phenyl vinyl ketone) Photopolymerization and Photodegradation under Visible and UV Radiation. Macromolecular Rapid Communications 2017, 38 (13) https://doi.org/10.1002/marc.201600623
    14. Elif Oz, Tamer Uyar, Huseyin Esen, Mehmet Atilla Tasdelen. Simultaneous photoinduced electron transfer and photoinduced CuAAC processes for antibacterial thermosets. Progress in Organic Coatings 2017, 105 , 252-257. https://doi.org/10.1016/j.porgcoat.2017.01.011
    15. Ahanjit Bhattacharya, Roberto J. Brea, Neal K. Devaraj. De novo vesicle formation and growth: an integrative approach to artificial cells. Chemical Science 2017, 8 (12) , 7912-7922. https://doi.org/10.1039/C7SC02339A

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