A highly sensitive probe based on spiropyran for colorimetric and fluorescent detection of thiophenol in aqueous media

Yang, Linlin; Li, Yanping; Song, Huaxiong; Zhang, Haihua; Yang, Nan; Peng, Qian; Ji, Liguo; He, Guangjie

doi:10.1016/j.dyepig.2019.108154

Cited by 20 publications

(4 citation statements)

References 39 publications

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“…DLS measurements (Figure A for 25 mM PBS pH 6) show an increase of Mic and MicDoxHCl size upon reduction of the pH value, with values of 295 ± 5 nm (Peak width 128 nm) for Mic and of 340 ± 9 nm (Peak width 130 nm) for MicDoxHCl 5 μM. This increment in size at a more acidic pH may be due to the swelling of SP chains derived from their protonation (SP-H) and the consequent solvent internalization. A further increase in the size of Mic and MicDoxHCl until 342 ± 5 nm (Peak width 130 nm) and 360 ± 11 nm (Peak width 152 nm), was respectively observed after irradiation with UV light in 25 mM PBS (pH 6.0).…”

Section: Resultsmentioning

confidence: 97%

“…25 Similarly, interaction between the amino group of PNIPAM and the carbonyl groups of DoxHCl could be also expected. On the other hand, Dox, which dissolves in the less This increment in size at a more acidic pH may be due to the swelling of SP chains derived from their protonation (SP-H) 42 and the consequent solvent internalization. A further increase in the size of Mic and MicDoxHCl until 342 ± 5 nm (Peak width 130 nm) and 360 ± 11 nm (Peak width 152 nm), was respectively observed after irradiation with UV light in 25 mM PBS (pH 6.0).…”

Section: Electrophoretic Separations Formentioning

confidence: 99%

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Rational Understanding of Loading and Release of Doxorubicin by UV-Light- and pH-Responsive Poly(NIPAM-co-SPMA) Micelle-like Aggregates

et al. 2022

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A deep understanding of the interactions between micelle-like aggregates and antineoplastic drugs is paramount to control their adequate delivery. Herein, Poly(NIPAM-co-SPMA) copolymer nanocarriers were synthesized according to our previous published methodology, and the loading and release of poorly and highly water-soluble doxorubicin forms (Dox and Dox-HCl, respectively) were evaluated upon UV light irradiation and pH-variation stimuli. Capillary electrophoresis (CE) coupled to a fluorescence detector (LIF) allowed us to specifically characterize these systems and deeply study the loading and release processes. For this purpose, varying concentrations of doxorubicin were tested, and the loading/release rates were indirectly quantified thanks to the "free" doxorubicin concentration in solution. This study highlighted that Dox loading (9.4 μg/mg) was more effective than Dox-HCl loading (5.5 μg/mg). In contrast, 68 and 74% of Dox-HCl were respectively released after 2 min upon pH variation (from 7.4 to 6.0) and combined UV + pH 6.0 stimuli, while only 27% of Dox was invariably released upon application of the same stimuli. These results are coherent with the characteristics of both DoxHCl and Dox: Electrostatic interactions between Dox-HCl and the micelle-membrane structure (NIPAM) seemed predominant, while hydrophobic interactions were expected between Dox and the SP moieties at the inner part of the micelle-like aggregate, leading to different behaviors in both loading and release of the two doxorubicin forms. For doxorubicin loading concentrations higher than 3 μM, the electrophoretic profiles presented an additional peak. Thanks to CE characterizations, this peak was attributed to the formation of a complex formed between the nonaggregated copolymer and the doxorubicin molecules. This report therefore undergoes deep characterization of the dynamic formation of different micelle/drug complexes involved in the global drug-delivery behavior and therefore contributes to the development of more effective stimuli-responsive nanocarriers.

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Section: Resultsmentioning

confidence: 97%

Section: Electrophoretic Separations Formentioning

confidence: 99%

Rational Understanding of Loading and Release of Doxorubicin by UV-Light- and pH-Responsive Poly(NIPAM-co-SPMA) Micelle-like Aggregates

et al. 2022

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“…In 2007, Wang et al, first reported a benzoxazole based fluorescence probe to detect thiophenols. 65 Later on, in 2019, Yang et al 66 reported a 2,4-dinitrobenzenesulfonamide based fluorometric and colorimetric probe, 20 ( Figure 19 ), for the detection of thiophenol through the nucleophilic substitution–cyclization reaction. Upon the addition of thiophenol, the highly electron-withdrawing capacity of the 2,4-dinitrobenzenesulfonamide unit was cleaved.…”

Section: Fluorescent Chemosensors For Neutral Analytesmentioning

confidence: 99%

Spiropyran–Merocyanine Based Photochromic Fluorescent Probes: Design, Synthesis, and Applications

et al. 2022

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Due to ever-increasing insights into their fundamental properties and photochromic behaviors, spiropyran derivatives are still a target of interest for researchers. The interswitching ability of this photochrome between the spiropyran (SP) and merocyanine (MC) isoforms under external stimuli (light, cations, anions, pH etc.) with different spectral properties as well as the protonation–deprotonation of its MC form allows researchers to use it suitably in sensing purposes by developing different colorimetric and fluorometric probes. Selective and sensitive recognition can be achieved by little modification of its SP moiety and functional groups. In this review, we emphasize the recent advancements (from 2019 to 2022) of spiropyran–merocyanine based fluorogenic and chromogenic probes for selective detection of various metal ions, anions, neutral analytes, and pH. We precisely explain their design strategies, sensing mechanisms, and biological and environmental applications. This review may accelerate the improvements in designing more advanced probes with innovative applications in the near future.

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“…By contrast, fluorescent-based probes have great potential applications in both environmental and biological systems because of their high sensitivity, simplicity, lower detection limits, and nondestructive detection. − However, development of fluorescent probes for thiophenol is extremely challenging to differentiate thiophenol from thiols due to similar chemical properties between thiophenol and thiols. Fortunately, since the pioneer work of distinguishing thiophenol and thiols from Wang, a number of probes have been developed based 2,4-dinitrobenzenesulfonate and dinitrophenyl ether recognition groups. − Although those probes worked well, many limitations in practical use remain to be overcome. For example, some probes could suffer from slow response (>10 min) or need of surfactants to accelerate the reactions, which was a disadvantage for real-time detection.…”

Section: Introductionmentioning

confidence: 99%

Simple NIR-Emitting ESIPT Fluorescent Probe for Thiophenol with a Remarkable Stokes Shift and Its Application

Shen

et al. 2020

ACS Omega

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Thiophenol as a highly toxic compound can harm the environment and living organisms and thus demands effective detection. In this work, we presented a near-infrared fluorescent probe (DAPH-DNP) for detecting thiophenol according to the ESIPT mechanism using 2,4-dinitrophenyl group as a recognition unit. This probe displayed specificity toward thiophenol over other related analytes. Meanwhile, there was good linearity between the relative fluorescence intensity of DAPH-DNP and the concentration of thiophenol in the range of 0–80 μM. This probe also showed a low detection limit of 3.8 × 10–8 and a marked Stokes shift (192 nm). Further, this probe could be used for monitoring thiophenol in environmental water samples and imaging thiophenol in living cells, which indicated that this probe had a real application in the environment and living organisms.

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A highly sensitive probe based on spiropyran for colorimetric and fluorescent detection of thiophenol in aqueous media

Cited by 20 publications

References 39 publications

Rational Understanding of Loading and Release of Doxorubicin by UV-Light- and pH-Responsive Poly(NIPAM-co-SPMA) Micelle-like Aggregates

Rational Understanding of Loading and Release of Doxorubicin by UV-Light- and pH-Responsive Poly(NIPAM-co-SPMA) Micelle-like Aggregates

Spiropyran–Merocyanine Based Photochromic Fluorescent Probes: Design, Synthesis, and Applications

Simple NIR-Emitting ESIPT Fluorescent Probe for Thiophenol with a Remarkable Stokes Shift and Its Application

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