Fluorescence Quenching-Based Mechanism for Determination of Hypochlorite by Coumarin-Derived Sensors
Abstract
:1. Introduction
2. Results and Discussion
2.1. Determination of the Effect of Hypochlorite on the Emission Properties of the Probes
2.2. The pH Effects on the Hypochlorite Detection by Coumarin-Derived Probes
2.3. Mass Spectrometry Analysis of the Reaction Mixtures
2.4. Investigation into the Fluorescence of Probes in the Presence of Anti-Hypochlorite Agent Trolox
2.5. Assessment of Applicability of Probes 1–3 as Tools for Quantitative Determination of Hypochlorite
2.6. Isolation and Structural Characterisation of Chlorinated Derivative 2a′
3. Materials and Methods
3.1. Materials
3.2. Methods
3.3. Synthesis of Coumarin Derivatives
3.3.1. Synthesis of 7-Diethylamino-3-Formylcoumarin 1
3.3.2. Synthesis of 7-Diethylaminocoumarin 3-Carboxylic Acid 2
3.3.3. Isolation of Chlorinated Derivative of 7-Diethylaminocoumarin 3-Carboxylic Acid 2a′
3.4. Fluorescence Assay
3.4.1. Determination of the Effect of Hypochlorite on the Emission Properties of the Probes
3.4.2. Investigation into the Fluorescence of Probes in the Presence of Anti-Hypochlorite Agent
3.5. Mass Spectrometry Analysis
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
Abbreviations
ICT | intramolecular charge transfer |
PET | photO−induced electron transfer |
FRET | fluorescence resonance energy transfer |
ESIPT | excited state intramolecular proton transfer |
ROS | reactive oxygen species |
HCSe | boron-dipyrromethene-based turn-on fluorescent probe |
ClO− | hypochlorite ion |
PDA | photodiode array |
ESI | electrospray ionisation |
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Compound No. | Compound Name | tret (min) | λmax (nm) | m/z [M+H]+ | Composition (%) |
---|---|---|---|---|---|
1 | 7-diethylamino-3-formylcoumarin | 7.9 | 443 | 246.05 | 29.1 |
1a′ | Monochloro-7-diethylamino-3-formylcoumarin * | 9.7 | 433 | 279.95 | 25.8 |
1a′′ | monochloro-7-diethylamino-3-formylcoumarin * | 11.1 | 440 | 279.05 | 2.5 |
1b | dichloro-7-diethylaminocoumarin * | 12.1 | 366 | 285.95 | 4.2 |
2 | 7-diethylaminocoumarin-3-carboxylic acid | 8.1 | 432 | 262.00 | 15.6 |
2a′ | monochloro-7-diethylaminocoumarin-3-carboxylic acid * | 9.9 | 411 | 295.95 | 33.5 |
2a′′ | monochloro-7-diethylaminocoumarin-3-carboxylic acid * | 10.9 | 396 | 295.95 | 0.5 |
1b | dichloro-7-diethylaminocoumarin * | 12.1 | 366 | 285.90 | 5.9 |
3a′ | monochloro-7-diethylamino-4-methylcoumarin * | 10.2 | 350 | 266.00 | 44.3 |
3 | 7-diethylamino-4-methylcoumarin | 10.5 | 375 | 232.05 | 27.2 |
3a′′ | monochloro-7-diethylamino-4-methylcoumarin * | 12.9 | 389 | 266.00 | 19.1 |
3b | dichloro-7-diethylamino-4-methylcoumarin * | 13.3 | 360 | 299.95 | 6.1 |
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Starzak, K.; Matwijczuk, A.; Creaven, B.; Matwijczuk, A.; Wybraniec, S.; Karcz, D. Fluorescence Quenching-Based Mechanism for Determination of Hypochlorite by Coumarin-Derived Sensors. Int. J. Mol. Sci. 2019, 20, 281. https://doi.org/10.3390/ijms20020281
Starzak K, Matwijczuk A, Creaven B, Matwijczuk A, Wybraniec S, Karcz D. Fluorescence Quenching-Based Mechanism for Determination of Hypochlorite by Coumarin-Derived Sensors. International Journal of Molecular Sciences. 2019; 20(2):281. https://doi.org/10.3390/ijms20020281
Chicago/Turabian StyleStarzak, Karolina, Arkadiusz Matwijczuk, Bernadette Creaven, Alicja Matwijczuk, Sławomir Wybraniec, and Dariusz Karcz. 2019. "Fluorescence Quenching-Based Mechanism for Determination of Hypochlorite by Coumarin-Derived Sensors" International Journal of Molecular Sciences 20, no. 2: 281. https://doi.org/10.3390/ijms20020281