A Multifunctional and Fast-Response Lysosome-Targetable Fluorescent Probe for Monitoring pH and Isoxaflutole
A new chemosensor, namely <i>N</i>-(2-morpholinoethyl)acetamide-4-morpholine-1,8-naphthimide (<b>MMN</b>), was designed and synthesized through an amidation reaction. <b>MMN</b> was fabricated as a multifunctional fluorescent probe for monitoring pH and isoxafluto...
| Main Authors: | , , , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2022-06-01
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| Series: | International Journal of Molecular Sciences |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1422-0067/23/11/6256 |
| Summary: | A new chemosensor, namely <i>N</i>-(2-morpholinoethyl)acetamide-4-morpholine-1,8-naphthimide (<b>MMN</b>), was designed and synthesized through an amidation reaction. <b>MMN</b> was fabricated as a multifunctional fluorescent probe for monitoring pH and isoxaflutole. <b>MMN</b> exhibited excellent stability in MeCN/H<sub>2</sub>O (<i>v</i>/<i>v</i>, 9/1), with an obvious “off–on” fluorescence response toward pH changes due to intramolecular charge transfer (ICT), where the linear response ranges of <b>MMN</b> in the weakly acidic system were from 4.2 to 5.0 and from 5.0 to 6.0 with apparent p<i>K<sub>a</sub></i> = 4.62 ± 0.02 and 5.43 ± 0.02. Based on morpholine as the lysosome targetable unit, <b>MMN</b> could selectively locate lysosomes in live cells. <b>MMN</b> also successfully detected the presence of H<sup>+</sup> in test papers. Finally, <b>MMN</b> could specifically recognize isoxaflutole at a detection limit of 0.88 μM. A possible sensing mechanism was identified based on density function theory calculations. These results indicate that <b>MMN</b> could be a superior potential chemosensor for detecting pH and isoxaflutole selectively and sensitively and could be used in real sample detection. |
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| ISSN: | 1661-6596 1422-0067 |