Coumarin-based fluorescent ‘AND’ logic gate probes for the detection of homocysteine and a chosen biological analyte

Luling Wu; Jordan E. Gardiner; Lokesh K. Kumawat; Hai-Hao Han; Ruiying Guo; Xin Li; Xiao-Peng He; Robert B. P. Elmes; Adam C. Sedgwick; Steven D. Bull; Tony D. James

doi:10.1039/C9RA04908H

Coumarin-based fluorescent ‘AND’ logic gate probes for the detection of homocysteine and a chosen biological analyte†

Luling Wu,

^a Jordan E. Gardiner,

^a Lokesh K. Kumawat,^c Hai-Hao Han,

^d Ruiying Guo,^e Xin Li,

*^e Xiao-Peng He,

*^d Robert B. P. Elmes,

*^cf Adam C. Sedgwick,

*^b Steven D. Bull

*^a and Tony D. James

*^a

Author affiliations

* Corresponding authors

^a Department of Chemistry, University of Bath, Bath, UK
E-mail: t.d.james@bath.ac.uk, chssdb@bath.ac.uk

^b Department of Chemistry, University of Texas at Austin, 105 E 24th Street A5300, Austin, TX 78712-1224, USA
E-mail: a.c.sedgwick@utexas.edu

^c Department of Chemistry, Maynooth University Human Health Institute, Maynooth University, National University of Ireland, Maynooth, County Kildare, Ireland
E-mail: Robert.Elmes@mu.ie

^d Key Laboratory for Advanced Materials, Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, School of Chemistry and Molecular Engineering, East China University of Science and Technology, 130 Meilong Rd, Shanghai 200237, China
E-mail: xphe@ecust.edu.cn

^e College of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058, China
E-mail: lixin81@zju.edu.cn

^f Synthesis and Solid State Pharmaceutical Centre, Maynooth University, Ireland

Abstract

With this research we set out to develop a number of coumarin-based ‘AND’ logic fluorescence probes that were capable of detecting a chosen analyte in the presence of HCys. Probe JEG-CAB was constructed by attaching the ONOO⁻ reactive unit, benzyl boronate ester, to a HCys/Cys reactive fluorescent probe, CAH. Similarly, the core unit CAH was functionalised with the nitroreductase (NTR) reactive p-nitrobenzyl unit to produce probe JEG-CAN. Both, JEG-CAB and JEG-CAN exhibited a significant fluorescence increase when exposed to either HCys and ONOO⁻ (JEG-CAB) or HCys and NTR (JEG-CAN) thus demonstrating their effectiveness to function as AND logic gates for HCys and a chosen analyte.

This article is part of the themed collection: The Mechanics of Supramolecular Chemistry

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Coumarin-based fluorescent ‘AND’ logic gate probes for the detection of homocysteine and a chosen biological analyte†

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Coumarin-based fluorescent ‘AND’ logic gate probes for the detection of homocysteine and a chosen biological analyte

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