Partridge, B. orcid.org/0000-0002-8550-9994 (2025) Design and synthesis of arylboronic acid chemosensors for the fluorescent-thin layer chromatography (f-TLC) detection of mycolactone. Chemosensors, 13 (7). ISSN 2227-9040
Abstract
Fluorescent chemosensors are increasingly becoming relevant in recognition chemistry due to their sensitivity, selectivity, fast response time, real-time detection capability, and low cost. Boronic acids have been reported for the recognition of mycolactone, the cytotoxin responsible for tissue damage in Buruli ulcer disease. A library of fluorescent arylboronic acid chemosensors with various signaling moieties with certain beneficial photophysical characteristics (i.e., aminoacridine, aminoquinoline, azo, BODIPY, coumarin, fluorescein, and rhodamine variants) and a recognition moiety (i.e., boronic acid unit) were rationally designed and synthesised using combinatorial approaches, purified, and fully characterised using a set of complementary spectrometric and spectroscopic techniques such as NMR, LC-MS, FT-IR, and X-ray crystallography. In addition, a complete set of basic photophysical quantities such as absorption maxima (λabsmax), emission maxima (λemmax), Stokes shift (∆λ), molar extinction coefficient (ε), fluorescence quantum yield (ΦF), and brightness were determined using UV-vis absorption and fluorescence emission spectroscopy techniques. The synthesised arylboronic acid chemosensors were investigated as chemosensors for mycolactone detection using the fluorescent-thin layer chromatography (f-TLC) method. Compound 7 (with a coumarin core) emerged the best (λabsmax = 456 nm, λemmax = 590 nm, ∆λ = 134 nm, ε = 52816 M−1cm−1, ΦF = 0.78, and brightness = 41,197 M−1cm−1).
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © 2025 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). |
Keywords: | mycolactone; Buruli ulcer; boronic acid; chemosensor; diagnosis; molecular recognition; mycolactone; Mycobacterium ulcerans |
Dates: |
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Institution: | The University of Sheffield |
Academic Units: | The University of Sheffield > Faculty of Science (Sheffield) > School of Mathematical and Physical Sciences |
Depositing User: | Symplectic Sheffield |
Date Deposited: | 09 Jul 2025 08:53 |
Last Modified: | 09 Jul 2025 08:53 |
Status: | Published |
Publisher: | MDPI AG |
Refereed: | Yes |
Identification Number: | 10.3390/chemosensors13070244 |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:228950 |