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Vol. 13 (2021)

Functional Surfactants for Molecular Fishing, Capsule Creation, and Single-Cell Gene Expression

https://doi.org/10.1007/s40820-021-00663-x
Mohammad Suman Chowdhury
Institut Für Chemie Und Biochemie, Freie Universität Berlin, Takustrasse 3, 14195 Berlin, Germany
Xingcai Zhang
John A. Paulson School of Engineering and Applied Sciences, Harvard University, Cambridge, MA 02138, USA
Leila Amini
Berlin Institute of Health – Center for Regenerative Therapies, Charité Universitätsmedizin Berlin – CVK, Föhrer Str. 15, 13353 Berlin, Germany
Pradip Dey
Institut Für Chemie Und Biochemie, Freie Universität Berlin, Takustrasse 3, 14195 Berlin, Germany
Abhishek Kumar Singh
Institut Für Chemie Und Biochemie, Freie Universität Berlin, Takustrasse 3, 14195 Berlin, Germany
Abbas Faghani
Institut Für Chemie Und Biochemie, Freie Universität Berlin, Takustrasse 3, 14195 Berlin, Germany
Michael Schmueck‑Henneresse
Berlin Institute of Health – Center for Regenerative Therapies, Charité Universitätsmedizin Berlin – CVK, Föhrer Str. 15, 13353 Berlin, Germany
Rainer Haag
Institut Für Chemie Und Biochemie, Freie Universität Berlin, Takustrasse 3, 14195 Berlin, Germany

Corresponding Author: Rainer Haag

haag@chemie.fu-berlin.de

Nano-Micro Letters, Vol. 13 (2021), Article Number: 147

Abstract

Creating a single surfactant that is open to manipulation, while maintaining its surface activity, robustness, and compatibility, to expand the landscape of surfactant-dependent assays is extremely challenging. We report an oxidation-responsive precursor with thioethers and multiple 1,2-diols for creating a variety of functional surfactants from one parent surfactant. Using these multifunctional surfactants, we stabilize microfluidics-generated aqueous droplets. The droplets encapsulate different components and immerse in a bioinert oil with distinct interfaces where an azide-bearing surfactant allow fishing of biomolecules from the droplets, aldehyde-bearing surfactant allow fabrication of microcapsules, and hydroxyl-bearing surfactants, with/without oxidized thioethers, allow monitoring of single-cell gene expression. Creating multifunctional surfactants poses opportunities for broad applications, including adsorption, bioanalytics, catalysis, formulations, coatings, and programmable subset of emulsions.


Highlights:


1 We have demonstrated how to create a parent surfactant that is open to manipulation, while maintaining its surface activity, robustness, and compatibility, to expand the landscape of surfactant-dependent microfluidic-droplet-based assays.
2 To create a library of functional surfactants from the parent surfactant, an oxidation-responsive small building block with thioethers and multiple 1,2-diols was used as a head group, while a non-polar perfluoropolyether chain was used as a tail.

Keywords

Dendronized fluorosurfactants Droplet microfluidics Microcapsules Oxidation-responsive fluorosurfactants Cell encapsulation
Chowdhury, Mohammad Suman, Xingcai Zhang, Leila Amini, Pradip Dey, Abhishek Kumar Singh, Abbas Faghani, Michael Schmueck‑Henneresse, and Rainer Haag. 2021. “Functional Surfactants for Molecular Fishing, Capsule Creation, and Single-Cell Gene Expression”. Nano-Micro Letters 13 (June):147. https://doi.org/10.1007/s40820-021-00663-x.
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References
  1. L.H. Urner, I. Liko, H.-S. Yen, K.-K. Hoi, J.R. Bolla et al., Modular detergents tailor the purification and structural analysis of membrane proteins including G-protein coupled receptors. Nat. Commun. 11, 564 (2020). https://doi.org/10.1038/s41467-020-14424-8
  2. Z. Tang, N. Kong, X. Zhang, Y. Liu, P. Hu et al., A materials-science perspective on tackling COVID-19. Nat. Rev. Mater. 5, 847–860 (2020). https://doi.org/10.1038/s41578-020-00247-y
  3. A.B. Theberge, F. Courtois, Y. Schaerli, M. Fischlechner, C. Abell et al., Microdroplets in microfluidics: an evolving platform for discoveries in chemistry and biology. Angew. Chem. Int. Ed. 49, 5846–5868 (2010). https://doi.org/10.1002/anie.200906653
  4. L. Liu, N. Xiang, Z. Ni, X. Huang, J. Zheng et al., Step emulsification: high-throughput production of monodisperse droplets. Biotechniques 68, 114–116 (2020). https://doi.org/10.2144/btn-2019-0134
  5. J.J. Agresti, E. Antipov, A.R. Abate, K. Ahn, A.C. Rowat et al., Ultrahigh-throughput screening in drop-based microfluidics for directed evolution. Proc. Natl. Acad. Sci. USA 107, 4004–4009 (2010). https://doi.org/10.1073/pnas.0910781107
  6. A.M. Klein, L. Mazutis, I. Akartuna, N. Tallapragada, A. Veres et al., Droplet barcoding for single-cell transcriptomics applied to embryonic stem cells. Cell 161, 1187–1201 (2015). https://doi.org/10.1016/j.cell.2015.04.044
  7. A. Gérard, A. Woolfe, G. Mottet, M. Reichen, C. Castrillon et al., High-throughput single-cell activity-based screening and sequencing of antibodies using droplet microfluidics. Nat. Biotechnol. 38, 715–721 (2020). https://doi.org/10.1038/s41587-020-0466-7
  8. J. Zhang, R.J. Coulston, S.T. Jones, J. Geng, O.A. Scherman et al., One-step fabrication of supramolecular microcapsules from microfluidic droplets. Science 335, 690–694 (2012). https://doi.org/10.1126/science.1215416
  9. T.E. Miller, T. Beneyton, T. Schwander, C. Diehl, M. Girault et al., Light-powered CO2 fixation in a chloroplast mimic with natural and synthetic parts. Science 368, 649–654 (2020). https://doi.org/10.1126/science.aaz6802
  10. M. Weiss, J.P. Frohnmayer, L.T. Benk, B. Haller, J.-W. Janiesch et al., Sequential bottom-up assembly of mechanically stabilized synthetic cells by microfluidics. Nat. Mater. 17, 89–96 (2018). https://doi.org/10.1038/nmat5005
  11. L. Cohen, N. Cui, Y. Cai, P.M. Garden, X. Li et al., Single molecule protein detection with attomolar sensitivity using droplet digital enzyme-linked immunosorbent assay. ACS Nano 14, 9491–9501 (2020). https://doi.org/10.1021/acsnano.0c02378
  12. C. Holtze, A.C. Rowat, J.J. Agresti, J.B. Hutchison, F.E. Angilè et al., Biocompatible surfactants for water-in-fluorocarbon emulsions. Lab Chip 8, 1632–1639 (2008). https://doi.org/10.1039/B806706F
  13. M.S. Chowdhury, W. Zheng, S. Kumari, J. Heyman, X. Zhang et al., Dendronized fluorosurfactant for highly stable water-in-fluorinated oil emulsions with minimal inter-droplet transfer of small molecules. Nat. Commun. 10, 4546 (2019). https://doi.org/10.1038/s41467-019-12462-5
  14. I. Platzman, J.-W. Janiesch, J.P. Spatz, Synthesis of nanostructured and biofunctionalized water-in-oil droplets as tools for homing T cells. J. Am. Chem. Soc. 135, 3339–3342 (2013). https://doi.org/10.1021/ja311588c
  15. M. Cui, T. Emrick, T.P. Russell, Stabilizing liquid drops in nonequilibrium shapes by the interfacial jamming of nanoparticles. Science 342, 460–463 (2013). https://doi.org/10.1126/science.1242852
  16. C. Huang, J. Forth, W. Wang, K. Hong, G.S. Smith et al., Bicontinuous structured liquids with sub-micrometre domains using nanoparticle surfactants. Nat. Nanotechnol. 12, 1060–1063 (2017). https://doi.org/10.1038/nnano.2017.182
  17. D. Kumar, J.D. Paulsen, T.P. Russell, N. Menon, Wrapping with a splash: high-speed encapsulation with ultrathin sheets. Science 359, 775–778 (2018). https://doi.org/10.1126/science.aao1290
  18. L.D. Zarzar, V. Sresht, E.M. Sletten, J.A. Kalow, D. Blankschtein et al., Dynamically reconfigurable complex emulsions via tunable interfacial tensions. Nature 518, 520–524 (2015). https://doi.org/10.1038/nature14168
  19. Z. Yang, J. Wei, Y.I. Sobolev, B.A. Grzybowski, Systems of mechanized and reactive droplets powered by multi-responsive surfactants. Nature 553, 313–318 (2018). https://doi.org/10.1038/nature25137
  20. A.S. Cheung, D.K.Y. Zhang, S.T. Koshy, D.J. Mooney, Scaffolds that mimic antigen-presenting cells enable ex vivo expansion of primary T cells. Nat. Biotechnol. 36, 160–169 (2018). https://doi.org/10.1038/nbt.4047
  21. D.M. Rissin, C.W. Kan, T.G. Campbell, S.C. Howes, D.R. Fournier et al., Single-molecule enzyme-linked immunosorbent assay detects serum proteins at subfemtomolar concentrations. Nat. Biotechnol. 28, 595–599 (2010). https://doi.org/10.1038/nbt.1641
  22. C. Wu, P.M. Garden, D.R. Walt, Ultrasensitive detection of attomolar protein concentrations by dropcast single molecule assays. J. Am. Chem. Soc. 142, 12314–12323 (2020). https://doi.org/10.1021/jacs.0c04331
  23. L. Cohen, D.R. Walt, Evaluation of antibody biotinylation approaches for enhanced sensitivity of single molecule array (Simoa) immunoassays. Bioconj. Chem. 29, 3452–3458 (2018). https://doi.org/10.1021/acs.bioconjchem.8b00601
  24. R.P. Lyon, T.D. Bovee, S.O. Doronina, P.J. Burke, J.H. Hunter et al., Reducing hydrophobicity of homogeneous antibody-drug conjugates improves pharmacokinetics and therapeutic index. Nat. Biotechnol. 33, 733–735 (2015). https://doi.org/10.1038/nbt.3212
  25. N. Boehnke, C. Cam, E. Bat, T. Segura, H.D. Maynard, Imine hydrogels with tunable degradability for tissue engineering. Biomacromolecules 16, 2101–2108 (2015). https://doi.org/10.1021/acs.biomac.5b00519
  26. E. Amstad, Capsules made from prefabricated thin films. Science 359, 743 (2018). https://doi.org/10.1126/science.aar4027
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