Design and Synthesis of Arylboronic Acid Chemosensors for the Fluorescent-Thin Layer Chromatography (f-TLC) Detection of Mycolactone
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 dama...
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| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2025-07-01
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| Series: | Chemosensors |
| Subjects: | |
| Online Access: | https://www.mdpi.com/2227-9040/13/7/244 |
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| Summary: | 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 (λ<sub>abs</sub><sup>max</sup>), emission maxima (λ<sub>em</sub><sup>max</sup>), Stokes shift (∆λ), molar extinction coefficient (ε), fluorescence quantum yield (Φ<sub>F</sub>), 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 (λ<sub>abs</sub><sup>max</sup> = 456 nm, λ<sub>em</sub><sup>max</sup> = 590 nm, ∆λ = 134 nm, ε = 52816 M<sup>−1</sup>cm<sup>−1</sup>, Φ<sub>F</sub> = 0.78, and brightness = 41,197 M<sup>−1</sup>cm<sup>−1</sup>). |
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| ISSN: | 2227-9040 |