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Towards Single-Molecule Chiral Sensing and Separation

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Single Molecule Sensing Beyond Fluorescence

Part of the book series: Nanostructure Science and Technology ((NST))

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Abstract

Molecular chirality refers to molecules with the same composition but with different three-dimensional orientation. In biological systems, almost all molecules have chiral structures. Since molecules with different chirality may vary differently in their biochemical reaction, it is important to detect and separate these molecules in the biomedical and pharmaceutical industry. Despite significant progress made toward single-molecule sensing, it is still challenging to differentiate and detect chiral molecules at single-molecule resolution in racemic mixtures. Herein, we discuss the existing techniques towards single chiral molecule sensing and separation. We start with traditional methods, specifically chiral chromatographic methods, which label the chiral molecules with surfactants or other molecules in order to separate and detect them. New techniques using electromagnetic fields for label-free chiral sorting will also be explored. We then review the use of nanophotonic platforms to increase chiro-optical responses for chiral sensing with high sensitivity down to picogram quantities. We finalize with our perspective on opportunities and challenges for future development.

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References

  1. J. Gal, “Molecular chirality in chemistry and biology: Historical milestones,” Helvetica Chimica Acta, vol. 96, no. 9, pp. 1617–1657, 2013.

    CAS  Google Scholar 

  2. A. M. Evans, “Comparative pharmacology of s (+)-ibuprofen and (rs)-ibuprofen,” Clinical rheumatology, vol. 20, no. 1, pp. 9–14, 2001.

    Google Scholar 

  3. J. Kumar, H. Eraña, E. López-Martínez, N. Claes, V. F. Martín, D. M. Solís, S. Bals, A. L. Cortajarena, J. Castilla, and L. M. Liz-Marzán, “Detection of amyloid fibrils in parkinson,Äôs disease using plasmonic chirality,” Proceedings of the National Academy of Sciences, vol. 115, no. 13, pp. 3225–3230, 2018.

    CAS  Google Scholar 

  4. K. Kalíková, T. Šlechtová, and E. Tesařová, “Enantiomeric ratio of amino acids as a tool for determination of aging and disease diagnostics by chromatographic measurement,” Separations, vol. 3, no. 4, p. 30, 2016.

    Google Scholar 

  5. W. König, R. Krebber, and P. Mischnick, “Cyclodextrins as chiral stationary phases in capillary gas chromatography. part v: Octakis (3-o-butyryl-2, 6-di-o-pentyl)-\(\gamma \)-cyclodextrin,” Journal of High Resolution Chromatography, vol. 12, no. 11, pp. 732–738, 1989.

    Google Scholar 

  6. S. Fox, H. Strasdeit, S. Haasmann, and H. Brückner, “Gas chromatographic separation of stereoisomers of non-protein amino acids on modified \(\gamma \)-cyclodextrin stationary phase,” Journal of Chromatography A, vol. 1411, pp. 101–109, 2015.

    CAS  PubMed  Google Scholar 

  7. T. Loftsson and M. E. Brewster, “Pharmaceutical applications of cyclodextrins. 1. drug solubilization and stabilization,” Journal of pharmaceutical sciences, vol. 85, no. 10, pp. 1017–1025, 1996.

    CAS  PubMed  Google Scholar 

  8. Z. Aturki, “Use of \(\beta \)-cyclodextrin polymer as a chiral selector in capillary electrophoresis,” Journal of Chromatography A, vol. 680, no. 1, pp. 137–146, 1994.

    CAS  Google Scholar 

  9. M. B. Sørensen, P. Aaslo, H. Egsgaard, and T. Lund, “Determination of d/l-amino acids by zero needle voltage electrospray ionisation,” Rapid Communications in Mass Spectrometry: An International Journal Devoted to the Rapid Dissemination of Up-to-the-Minute Research in Mass Spectrometry, vol. 22, no. 4, pp. 455–461, 2008.

    Google Scholar 

  10. A. L. Ong, A. H. Kamaruddin, S. Bhatia, and H. Y. Aboul-Enein, “Enantioseparation of (r, s)-ketoprofen using candida antarctica lipase b in an enzymatic membrane reactor,” Journal of separation science, vol. 31, no. 13, pp. 2476–2485, 2008.

    CAS  PubMed  Google Scholar 

  11. B. Sellergren, “Imprinted chiral stationary phases in high-performance liquid chromatography,” Journal of Chromatography A, vol. 906, no. 1-2, pp. 227–252, 2001.

    CAS  PubMed  Google Scholar 

  12. R. Gutierrez-Climente, A. Gomez-Caballero, A. Guerreiro, D. Garcia-Mutio, N. Unceta, M. A. Goicolea, and R. J. Barrio, “Molecularly imprinted nanoparticles grafted to porous silica as chiral selectors in liquid chromatography,” Journal of Chromatography A, vol. 1508, pp. 53–64, 2017.

    CAS  PubMed  Google Scholar 

  13. J. Teixeira, M. E. Tiritan, M. M. Pinto, and C. Fernandes, “Chiral stationary phases for liquid chromatography: Recent developments,” Molecules, vol. 24, no. 5, p. 865, 2019.

    PubMed Central  Google Scholar 

  14. R. Sardella, F. Ianni, A. Lisanti, S. Scorzoni, F. Marini, S. Sternativo, and B. Natalini, “Direct chromatographic enantioresolution of fully constrained \(\beta \)-amino acids: exploring the use of high-molecular weight chiral selectors,” Amino acids, vol. 46, no. 5, pp. 1235–1242, 2014.

    CAS  PubMed  Google Scholar 

  15. C.-C. Hwang and W.-C. Lee, “Chromatographic resolution of the enantiomers of phenylpropanolamine by using molecularly imprinted polymer as the stationary phase,” Journal of Chromatography B: Biomedical Sciences and Applications, vol. 765, no. 1, pp. 45–53, 2001.

    CAS  PubMed  Google Scholar 

  16. E. Gil-Av, B. Feibush, and R. Charles-Sigler, “Separation of enantiomers by gas liquid chromatography with an optically active stationary phase,” Tetrahedron Letters, vol. 7, no. 10, pp. 1009–1015, 1966.

    Google Scholar 

  17. G. Tkachenko and E. Brasselet, “Optofluidic sorting of material chirality by chiral light,” Nature communications, vol. 5, no. 1, pp. 1–7, 2014.

    Google Scholar 

  18. T. Zhang, M. R. C. Mahdy, Y. Liu, J. H. Teng, C. T. Lim, Z. Wang, and C.-W. Qiu, “All-optical chirality-sensitive sorting via reversible lateral forces in interference fields,” ACS nano, vol. 11, no. 4, pp. 4292–4300, 2017.

    CAS  PubMed  Google Scholar 

  19. Y. Zhao, A. Saleh, and J. Dionne, “Enantioselective optical trapping of chiral nanoparticles with plasmonic tweezers.”

    Google Scholar 

  20. I. Liberal, I. Ederra, R. Gonzalo, and R. W. Ziolkowski, “Near-field electromagnetic trapping through curl-spin forces,” Physical Review A, vol. 87, no. 6, p. 063807, 2013.

    Google Scholar 

  21. K. Banerjee-Ghosh, O. B. Dor, F. Tassinari, E. Capua, S. Yochelis, A. Capua, S.-H. Yang, S. S. Parkin, S. Sarkar, L. Kronik, et al., “Separation of enantiomers by their enantiospecific interaction with achiral magnetic substrates,” Science, vol. 360, no. 6395, pp. 1331–1334, 2018.

    CAS  PubMed  Google Scholar 

  22. A. Kumar, E. Capua, M. K. Kesharwani, J. M. Martin, E. Sitbon, D. H. Waldeck, and R. Naaman, “Chirality-induced spin polarization places symmetry constraints on biomolecular interactions,” Proceedings of the National Academy of Sciences, vol. 114, no. 10, pp. 2474–2478, 2017.

    CAS  Google Scholar 

  23. Y. Tang and A. E. Cohen, “Optical chirality and its interaction with matter,” Physical review letters, vol. 104, no. 16, p. 163901, 2010.

    PubMed  Google Scholar 

  24. S. Yoo and Q.-H. Park, “Enhancement of chiroptical signals by circular differential mie scattering of nanoparticles,” Scientific reports, vol. 5, no. 1, pp. 1–8, 2015.

    CAS  Google Scholar 

  25. S. Lee, S. Yoo, and Q.-H. Park, “Microscopic origin of surface-enhanced circular dichroism,” ACS Photonics, vol. 4, no. 8, pp. 2047–2052, 2017.

    CAS  Google Scholar 

  26. Y. Zhao, “Chirality detection of enantiomers using twisted optical metamaterials,” Nature Communications, vol. 8, no. 1, pp. 1–8, 2017.

    Google Scholar 

  27. P. Gutsche and M. Nieto-Vesperinas, “Optical chirality of time-harmonic wavefields for classification of scatterers,” Scientific reports, vol. 8, no. 1, pp. 1–13, 2018.

    CAS  Google Scholar 

  28. L. V. Poulikakos, J. A. Dionne, and A. García-Etxarri, “Optical helicity and optical chirality in free space and in the presence of matter,” Symmetry, vol. 11, no. 9, p. 1113, 2019.

    CAS  Google Scholar 

  29. T. Raziman, R. H. Godiksen, M. A. Müller, and A. G. Curto, “Conditions for enhancing chiral nanophotonics near achiral nanoparticles,” ACS Photonics, vol. 6, no. 10, pp. 2583–2589, 2019.

    CAS  Google Scholar 

  30. M. Soltani, J. Lin, R. A. Forties, J. T. Inman, S. N. Saraf, R. M. Fulbright, M. Lipson, and M. D. Wang, “Nanophotonic trapping for precise manipulation of biomolecular arrays,” Nature nanotechnology, vol. 9, no. 6, p. 448, 2014.

    CAS  PubMed  PubMed Central  Google Scholar 

  31. Y. Liu, Z. Wu, and Y. Zheng, “Moiré chiral metamaterials,” Communication, vol. 5, no. 16, 2017.

    Google Scholar 

  32. J. Li, M. Wang, Z. Wu, H. Li, G. Hu, T. Jiang, J. Guo, Y. Liu, K. Yao, Z. Chen, et al., “Tunable chiral optics in all-solid-phase reconfigurable dielectric nanostructures,” Nano Letters, 2020.

    Google Scholar 

  33. M. Selmke, U. Khadka, A. P. Bregulla, F. Cichos, and H. Yang, “Theory for controlling individual self-propelled micro-swimmers by photon nudging i: directed transport,” Physical Chemistry Chemical Physics, vol. 20, no. 15, pp. 10502–10520, 2018.

    CAS  PubMed  Google Scholar 

  34. B. Qian, D. Montiel, A. Bregulla, F. Cichos, and H. Yang, “Harnessing thermal fluctuations for purposeful activities: the manipulation of single micro-swimmers by adaptive photon nudging,” Chemical Science, vol. 4, no. 4, pp. 1420–1429, 2013.

    CAS  Google Scholar 

  35. W. A. Paiva-Marques, F. Reyes Gómez, O. N. Oliveira, and J. R. Mejía-Salazar, “Chiral plasmonics and their potential for point-of-care biosensing applications,” Sensors, vol. 20, no. 3, p. 944, 2020.

    Google Scholar 

  36. J. García-Guirado, M. Svedendahl, J. Puigdollers, and R. Quidant, “Enantiomer-selective molecular sensing using racemic nanoplasmonic arrays,” Nano letters, vol. 18, no. 10, pp. 6279–6285, 2018.

    PubMed  Google Scholar 

  37. C. Kelly, L. Khosravi Khorashad, N. Gadegaard, L. D. Barron, A. O. Govorov, A. S. Karimullah, and M. Kadodwala, “Controlling metamaterial transparency with superchiral fields,” ACS Photonics, vol. 5, no. 2, pp. 535–543, 2018.

    Google Scholar 

  38. Y. Chen, X. Yang, and J. Gao, “3d janus plasmonic helical nanoapertures for polarization-encrypted data storage,” Light: Science & Applications, vol. 8, no. 1, pp. 1–9, 2019.

    Google Scholar 

  39. R. Zhang, Q. Zhao, X. Wang, W. Gao, J. Li, and W. Y. Tam, “Measuring circular phase-dichroism of chiral metasurface,” Nanophotonics, vol. 8, no. 5, pp. 909–920, 2019.

    Google Scholar 

  40. M. Schäferling, X. Yin, N. Engheta, and H. Giessen, “Helical plasmonic nanostructures as prototypical chiral near-field sources,” Acs Photonics, vol. 1, no. 6, pp. 530–537, 2014.

    Google Scholar 

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Acknowledgements

The authors acknowledge the financial support of the National Science Foundation (NSF–ECCS–2001650), the National Aeronautics and Space Administration Early Career Faculty Award (80NSSC17K0520), and the National Institute of General Medical Sciences of the National Institutes of Health (DP2GM128446). The authors also acknowledge the generous contribution of three illustrations by Naftal Mat Mautia.

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Authors and Affiliations

  1. Walker Department of Mechanical Engineering, The University of Texas at Austin, 204 E. Dean Keeton St., Austin, USA

    Riley Sanders

  2. Department of Electrical and Computer Engineering, The University of Texas at Austin, 2501 Speedway, Austin, USA

    Yaoran Liu

  3. Walker Department of Mechanical Engineering, Texas Materials Institute, Department of Electrical and Computer Engineering, and Department of Biomedical Engineering, The University of Texas at Austin, 204 E. Dean Keeton St., Austin, USA

    Yuebing Zheng

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  1. Riley Sanders
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Correspondence to Yuebing Zheng .

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Editors and Affiliations

  1. School of Mathematics and Physics, University of Queensland, Brisbane, QLD, Australia

    Warwick Bowen

  2. Department of Physics and Astronomy, University of Exeter, Exeter, UK

    Frank Vollmer

  3. Department of Computer and Electrical Engineering, University of Victoria, Victoria, BC, Canada

    Reuven Gordon

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Sanders, R., Liu, Y., Zheng, Y. (2022). Towards Single-Molecule Chiral Sensing and Separation. In: Bowen, W., Vollmer, F., Gordon, R. (eds) Single Molecule Sensing Beyond Fluorescence . Nanostructure Science and Technology. Springer, Cham. https://doi.org/10.1007/978-3-030-90339-8_9

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