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

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

142 Citations (SciVal)

137 Downloads (Pure)

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.

This project has received funding from the European Union’s Horizon 2020 research and innovation programme under the Marie Skłodowska-Curie grant agreement No 665992

Original language	English
Pages (from-to)	19389-19396
Number of pages	8
Journal	Journal of the American Chemical Society
Volume	141
Issue number	49
Early online date	27 Nov 2019
DOIs	https://doi.org/10.1021/jacs.9b09813
Publication status	Published - 11 Dec 2019

Funding

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.

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

Access to Document

10.1021/jacs.9b09813Licence: CC BY

jacs.9b09813(2)Final published version, 2.01 MBLicence: CC BY

Cite this

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

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

@article{341c0943de404684afa364eac797d4e2,

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.This project has received funding from the European Union{\textquoteright}s Horizon 2020 research and innovation programme under the Marie Sk{\l}odowska-Curie grant agreement No 665992 ",

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.}",

year = "2019",

month = dec,

day = "11",

doi = "10.1021/jacs.9b09813",

language = "English",

volume = "141",

pages = "19389--19396",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "49",

}

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.

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.This project has received funding from the European Union’s Horizon 2020 research and innovation programme under the Marie Skłodowska-Curie grant agreement No 665992

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.This project has received funding from the European Union’s Horizon 2020 research and innovation programme under the Marie Skłodowska-Curie grant agreement No 665992

UR - http://www.scopus.com/inward/record.url?scp=85076384021&partnerID=8YFLogxK

U2 - 10.1021/jacs.9b09813

DO - 10.1021/jacs.9b09813

M3 - Article

C2 - 31773957

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

Funding

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Simon Lewis

Balena High Performance Computing (HPC) System

Microplate reader BMG Labtech CLARIOstar

Cite this

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

Abstract

Funding

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Profiles

Simon Lewis

Equipment

Balena High Performance Computing (HPC) System

Microplate reader BMG Labtech CLARIOstar

Cite this