Long-wavelength TCF-based fluorescence probes for the detection and intracellular imaging of biological thiols

Adam C. Sedgwick, Jordan E. Gardiner, Gyoungmi Kim, Maksims Yevglevskis, Matthew D. Lloyd, A. Toby A. Jenkins, Steven D. Bull, Juyoung Yoon, Tony D. James

Research output: Contribution to journalArticlepeer-review

63 Scopus citations

Abstract

Two 'turn on' TCF-based fluorescence probes were developed for the detection of biological thiols (TCF-GSH and TCFCl-GSH). TCF-GSH was shown to have a high sensitivity towards glutathione (GSH) with a 0.28 μM limit of detection. Unfortunately, at higher GSH concentrations the fluorescence intensity of TCF-GSH decreased and toxicity was observed for TCF-GSH in live cells. However, TCFCl-GSH was shown to be able to detect GSH at biologically relevant concentrations with a 0.45 μM limit of detection. No toxicity was found for TCFCl-GSH and a clear 'turn on' with good photostability was observed for the exogenous addition of GSH, Cys and HCys. Furthermore, TCFCl-GSH was used to evaluate the effects of drug treatment on the levels of GSH in live cells.

Original languageEnglish
Pages (from-to)4786-4789
Number of pages4
JournalChemical Communications
Volume54
Issue number38
DOIs
StatePublished - 2018

Bibliographical note

Funding Information:
We would like to thank the EPSRC, the University of Bath and Prostate Cancer UK (PG14-009) for funding. ACS and JEG thank the EPSRC for studentships. TDJ wishes to thank the Royal Society for a Wolfson Research Merit Award. NMR characterisation facilities were provided through the Chemical Characterisation and Analysis Facility (CCAF) at the University of Bath (www.bath.ac.uk/ccaf). The EPSRC UK National Mass Spectrometry Facility at Swansea University is thanked for analyses. JY thanks the support from the National Research Foundation of Korea (NRF), which was funded by the Korea government (MSIP) (No. 2012R1A3A2048814). ACS, MY, MDL and TDJ are members of the Cancer Research@Bath (CR@B) network.

Publisher Copyright:
© The Royal Society of Chemistry 2018.

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