Azulene-Derived Fluorescent Probe for Bioimaging: Detection of Reactive Oxygen and Nitrogen Species by Two-Photon Microscopy

Lloyd C. Murfin; Maria Weber; Sang Jun Park; Won Tae Kim; Carlos M. Lopez-Alled; Claire L. McMullin; Fabienne Pradaux-Caggiano; Catherine L. Lyall; Gabriele Kociok-Köhn; Jannis Wenk; Steven D. Bull; Juyoung Yoon; Hwan Myung Kim; Tony D. James; Simon E. Lewis

doi:10.1021/jacs.9b09813

Azulene-Derived Fluorescent Probe for Bioimaging: Detection of Reactive Oxygen and Nitrogen Species by Two-Photon Microscopy

Lloyd C. Murfin, Maria Weber, Sang Jun Park, Won Tae Kim, Carlos M. Lopez-Alled, Claire L. McMullin, Fabienne Pradaux-Caggiano, Catherine L. Lyall, Gabriele Kociok-Köhn, Jannis Wenk, Steven D. Bull, Juyoung Yoon, Hwan Myung Kim, Tony D. James, Simon E. Lewis

Chemistry & Nanoscience

Research output: Contribution to journal › Article › peer-review

104 Scopus citations

Abstract

Two-photon fluorescence microscopy has become an indispensable technique for cellular imaging. Whereas most two-photon fluorescent probes rely on well-known fluorophores, here we report a new fluorophore for bioimaging, namely azulene. A chemodosimeter, comprising a boronate ester receptor motif conjugated to an appropriately substituted azulene, is shown to be an effective two-photon fluorescent probe for reactive oxygen species, showing good cell penetration, high selectivity for peroxynitrite, no cytotoxicity, and excellent photostability.

Original language	English
Pages (from-to)	19389-19396
Number of pages	8
Journal	Journal of the American Chemical Society
Volume	141
Issue number	49
DOIs	https://doi.org/10.1021/jacs.9b09813
State	Published - 11 Dec 2019

Bibliographical note

Funding Information:
We are grateful for Ph.D. funding to C.M.L.-A. from the EU Horizon 2020 research and innovation program under Grant Agreement H2020-MSCA-CO-FUND, No. 665992. We thank the Center for Doctoral Training in Sustainable Chemical Technologies for Ph.D. funding to M.W. under EPSRC Grant EP/L016354/1. We also thank EPSRC for DTP Ph.D. funding to L.C.M. H.M.K. acknowledges a grant from the National Leading Research Lab Program of the National Research Foundation of Korea (NRF), funded by the Korean government (MSIP; No. 2016R1E1A1A02920873). In addition, T.D.J. wishes to thank the Royal Society for a Wolfson Research Merit Award and for funding to F.P.-C. under Grant CHGR1170010. This work was supported by a seed corn grant from the CR@B (Cancer Research at Bath) network. The British-Spanish Society and Plastic Energy are thanked for a 2017 Scholarship to C. M. L.-A. This research made use of the Balena High Performance Computing (HPC) Service at the University of Bath. NMR, X-ray crystallography, and MS facilities were provided through the Materials and Chemical Characterisation Facility (MC 2 ) at the University of Bath. We thank Prof. Uwe Pischel and Prof. Thorfinnur Gunnlaugsson for helpful discussions.

Publisher Copyright:
© 2019 American Chemical Society.

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Murfin, L. C., Weber, M., Park, S. J., Kim, W. T., Lopez-Alled, C. M., McMullin, C. L., Pradaux-Caggiano, F., Lyall, C. L., Kociok-Köhn, G., Wenk, J., Bull, S. D., Yoon, J., Kim, H. M., James, T. D., & Lewis, S. E. (2019). Azulene-Derived Fluorescent Probe for Bioimaging: Detection of Reactive Oxygen and Nitrogen Species by Two-Photon Microscopy. Journal of the American Chemical Society, 141(49), 19389-19396. https://doi.org/10.1021/jacs.9b09813

@article{63c17b0d77fb4ca2a9bc67a2ea7ecc20,

title = "Azulene-Derived Fluorescent Probe for Bioimaging: Detection of Reactive Oxygen and Nitrogen Species by Two-Photon Microscopy",

abstract = "Two-photon fluorescence microscopy has become an indispensable technique for cellular imaging. Whereas most two-photon fluorescent probes rely on well-known fluorophores, here we report a new fluorophore for bioimaging, namely azulene. A chemodosimeter, comprising a boronate ester receptor motif conjugated to an appropriately substituted azulene, is shown to be an effective two-photon fluorescent probe for reactive oxygen species, showing good cell penetration, high selectivity for peroxynitrite, no cytotoxicity, and excellent photostability.",

author = "Murfin, {Lloyd C.} and Maria Weber and Park, {Sang Jun} and Kim, {Won Tae} and Lopez-Alled, {Carlos M.} and McMullin, {Claire L.} and Fabienne Pradaux-Caggiano and Lyall, {Catherine L.} and Gabriele Kociok-K{\"o}hn and Jannis Wenk and Bull, {Steven D.} and Juyoung Yoon and Kim, {Hwan Myung} and James, {Tony D.} and Lewis, {Simon E.}",

note = "Funding Information: We are grateful for Ph.D. funding to C.M.L.-A. from the EU Horizon 2020 research and innovation program under Grant Agreement H2020-MSCA-CO-FUND, No. 665992. We thank the Center for Doctoral Training in Sustainable Chemical Technologies for Ph.D. funding to M.W. under EPSRC Grant EP/L016354/1. We also thank EPSRC for DTP Ph.D. funding to L.C.M. H.M.K. acknowledges a grant from the National Leading Research Lab Program of the National Research Foundation of Korea (NRF), funded by the Korean government (MSIP; No. 2016R1E1A1A02920873). In addition, T.D.J. wishes to thank the Royal Society for a Wolfson Research Merit Award and for funding to F.P.-C. under Grant CHGR1170010. This work was supported by a seed corn grant from the CR@B (Cancer Research at Bath) network. The British-Spanish Society and Plastic Energy are thanked for a 2017 Scholarship to C. M. L.-A. This research made use of the Balena High Performance Computing (HPC) Service at the University of Bath. NMR, X-ray crystallography, and MS facilities were provided through the Materials and Chemical Characterisation Facility (MC 2 ) at the University of Bath. We thank Prof. Uwe Pischel and Prof. Thorfinnur Gunnlaugsson for helpful discussions. Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",

year = "2019",

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Murfin, LC, Weber, M, Park, SJ, Kim, WT, Lopez-Alled, CM, McMullin, CL, Pradaux-Caggiano, F, Lyall, CL, Kociok-Köhn, G, Wenk, J, Bull, SD, Yoon, J, Kim, HM, James, TD & Lewis, SE 2019, 'Azulene-Derived Fluorescent Probe for Bioimaging: Detection of Reactive Oxygen and Nitrogen Species by Two-Photon Microscopy', Journal of the American Chemical Society, vol. 141, no. 49, pp. 19389-19396. https://doi.org/10.1021/jacs.9b09813

TY - JOUR

T1 - Azulene-Derived Fluorescent Probe for Bioimaging

T2 - Detection of Reactive Oxygen and Nitrogen Species by Two-Photon Microscopy

AU - Murfin, Lloyd C.

AU - Weber, Maria

AU - Park, Sang Jun

AU - Kim, Won Tae

AU - Lopez-Alled, Carlos M.

AU - McMullin, Claire L.

AU - Pradaux-Caggiano, Fabienne

AU - Lyall, Catherine L.

AU - Kociok-Köhn, Gabriele

AU - Wenk, Jannis

AU - Bull, Steven D.

AU - Yoon, Juyoung

AU - Kim, Hwan Myung

AU - James, Tony D.

AU - Lewis, Simon E.

N1 - Funding Information: We are grateful for Ph.D. funding to C.M.L.-A. from the EU Horizon 2020 research and innovation program under Grant Agreement H2020-MSCA-CO-FUND, No. 665992. We thank the Center for Doctoral Training in Sustainable Chemical Technologies for Ph.D. funding to M.W. under EPSRC Grant EP/L016354/1. We also thank EPSRC for DTP Ph.D. funding to L.C.M. H.M.K. acknowledges a grant from the National Leading Research Lab Program of the National Research Foundation of Korea (NRF), funded by the Korean government (MSIP; No. 2016R1E1A1A02920873). In addition, T.D.J. wishes to thank the Royal Society for a Wolfson Research Merit Award and for funding to F.P.-C. under Grant CHGR1170010. This work was supported by a seed corn grant from the CR@B (Cancer Research at Bath) network. The British-Spanish Society and Plastic Energy are thanked for a 2017 Scholarship to C. M. L.-A. This research made use of the Balena High Performance Computing (HPC) Service at the University of Bath. NMR, X-ray crystallography, and MS facilities were provided through the Materials and Chemical Characterisation Facility (MC 2 ) at the University of Bath. We thank Prof. Uwe Pischel and Prof. Thorfinnur Gunnlaugsson for helpful discussions. Publisher Copyright: © 2019 American Chemical Society.

PY - 2019/12/11

Y1 - 2019/12/11

N2 - Two-photon fluorescence microscopy has become an indispensable technique for cellular imaging. Whereas most two-photon fluorescent probes rely on well-known fluorophores, here we report a new fluorophore for bioimaging, namely azulene. A chemodosimeter, comprising a boronate ester receptor motif conjugated to an appropriately substituted azulene, is shown to be an effective two-photon fluorescent probe for reactive oxygen species, showing good cell penetration, high selectivity for peroxynitrite, no cytotoxicity, and excellent photostability.

AB - Two-photon fluorescence microscopy has become an indispensable technique for cellular imaging. Whereas most two-photon fluorescent probes rely on well-known fluorophores, here we report a new fluorophore for bioimaging, namely azulene. A chemodosimeter, comprising a boronate ester receptor motif conjugated to an appropriately substituted azulene, is shown to be an effective two-photon fluorescent probe for reactive oxygen species, showing good cell penetration, high selectivity for peroxynitrite, no cytotoxicity, and excellent photostability.

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DO - 10.1021/jacs.9b09813

M3 - Article

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AN - SCOPUS:85076384021

SN - 0002-7863

VL - 141

SP - 19389

EP - 19396

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 49

ER -

Azulene-Derived Fluorescent Probe for Bioimaging: Detection of Reactive Oxygen and Nitrogen Species by Two-Photon Microscopy

Abstract

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