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Porphyrin Dyes for Nonlinear Optical Imaging of Live Cells

Khadria, Anjul and Fleischhauer, Jan and Boczarow, Igor and Wilkinson, James D. and Kohl, Michael M. and Anderson, Harry L. (2018) Porphyrin Dyes for Nonlinear Optical Imaging of Live Cells. iScience, 4 . pp. 153-163. ISSN 2589-0042.

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Second harmonic generation-based (SHG) biological probes are useful for nonlinear optical imaging of biological structures such as the plasma membrane. Several amphiphilic porphyrin-based dyes with high SHG coefficients have been synthesized with different hydrophilic head-groups and their cellular targeting has been studied. The probes with cationic head-groups localize better at the plasma membrane than the neutral probes with zwitterionic or non-charged ethylene glycol-based head-groups. Porphyrin dyes with only dications as hydrophilic head-groups localize inside HEK 293T cells to give SHG, while tricationic dyes localize robustly at the plasma membrane of cells including neurons in vitro and ex vivo. The copper(II) complex of the tricationic dye with negligible fluorescence quantum yield works as a SHG-only dye. The free-base tricationic dye has been demonstrated for two-photon fluorescence and SHG-based multimodal imaging. This study demonstrates the importance of a balance between the hydrophobicity and hydrophilicity of amphiphilic dyes for effective plasma membrane localization.

Item Type:Article
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Khadria, Anjul0000-0002-9771-3650
Boczarow, Igor0000-0003-2018-3548
Additional Information:© 2018 The Author(s). This is an open access article under the CC BY license ( Received 2 March 2018, Revised 9 May 2018, Accepted 22 May 2018, Available online 26 May 2018. We thank the John Fell Fund and EP Abraham Cephalosporin Fund, University of Oxford, for partly funding the multiphoton microscope. This project was supported by the EPSRC (grants EP/H018565/1 and EP/G03706X/1 - Systems Biology Centre of Doctoral Training). A.K. acknowledges the Clarendon Scholarships, Hilla Ginwala Scholarships, Radhakrishnan Memorial Fund, and St Catherine's College Overseas Graduate Scholarships at the University of Oxford. We thank Prof. Nigel Emptage, University of Oxford, for providing cultured rat hippocampal neurons. We thank Prof. Timothy Claridge and Dr. Przemyslaw Gawel (both University of Oxford) for useful discussion. Author Contributions: Conceptualization, A.K. and H.L.A.; Methodology, A.K. and H.L.A.; Investigation, A.K., J.F., I.G., and J.D.W.; Writing, A.K. and H.L.A.; Resources, M.M.K. and H.L.A.; Funding Acquisition, H.L.A.; Project Administration, H.L.A.; Supervision, H.L.A. Declaration of Interests: The authors declare no competing interests.
Funding AgencyGrant Number
University of OxfordUNSPECIFIED
Engineering and Physical Sciences Research Council (EPSRC)EP/H018565/1
Engineering and Physical Sciences Research Council (EPSRC)EP/G03706X/1
Subject Keywords:Second harmonic generation; porphyrins; multimodal imaging; membrane probes; amphiphilic dyes; cationic dyes; zwitterionic dyes; nonlinear optical microscopy; live cell imaging; plasma membrane imaging
Record Number:CaltechAUTHORS:20180529-091828341
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Official Citation:Anjul Khadria, Jan Fleischhauer, Igor Boczarow, James D. Wilkinson, Michael M. Kohl, Harry L. Anderson, Porphyrin Dyes for Nonlinear Optical Imaging of Live Cells, iScience, Volume 4, 2018, Pages 153-163, ISSN 2589-0042, (
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:86651
Deposited By: Tony Diaz
Deposited On:29 May 2018 16:35
Last Modified:03 Oct 2019 19:46

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