A triphenylamine as a fluorophore and maleimide as a bonding group selective turn-on fluorescent imaging probe for thiols

Liu, Tao; Huo, Fangjun; Yin, Caixia; Li, Jianfang; Chao, Jianbin; Zhang, Yongbin

doi:10.1016/j.dyepig.2015.12.031

Cited by 47 publications

(21 citation statements)

References 43 publications

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“…Table 2 shows the detection limits of the tested compounds 7a to 7c for L-Cys. The lowest concentration of L-Cys that can be determined by the presented fluorescent probes is 0.111-0.271 lM, which is comparable with other reported compounds [23,26,27,[38][39][40][41][42]. The lowest concentration of L-Cys that can be determined by the presented fluorescent probes is 0.111-0.271 lM, which is comparable with other reported compounds [23,26,27,[38][39][40][41][42].…”

Section: Studies Of the Spectroscopic Response To Thiolssupporting

confidence: 86%

“…It can be seen that dyes 7a to 7c exhibit high sensitivity to L-Cys. The lowest concentration of L-Cys that can be determined by the presented fluorescent probes is 0.111-0.271 lM, which is comparable with other reported compounds [23,26,27,[38][39][40][41][42].…”

Section: Studies Of the Spectroscopic Response To Thiolssupporting

confidence: 84%

“…UPLC and mass spectral analyses of products formed in the reaction with L-Cys It is well known from the literature [44] that thiols undergo addition to the double bonds of unsaturated compounds to give sulphides. Thus, based on previously reported studies on the reaction mechanism between thiols and various maleimide derivatives [24][25][26][27][28][29][30][31][32], in the case of tested dyes 7, products of addition to the double bonds of the maleimide moiety are also expected to be formed. For better characterisation of the products formed in the reaction of 7a and 7b with L-Cys, UPLC and mass spectral analyses were performed (Figures 14 and 15).…”

Section: Studies Of the Spectroscopic Response To Thiolsmentioning

confidence: 99%

“…The optical detection of thiols is based on specific reactions between probes and sulphydryl derivatives. Since then, a large number of probes with a maleimide moiety have been developed [23][24][25][26][27][28][29][30][31]. In our previous papers [20,21], the synthesis and spectroscopic characterisation, in the presence of various amino acids, of dyes derived from 3formyl-2(1H)-quinolone with different moieties acting as a Michael acceptor were reported.…”

Section: Introductionmentioning

confidence: 99%

“…The first probe for thiols that utilised the addition of mercapto derivatives to the maleimide moiety was obtained by Sippel [22]. Since then, a large number of probes with a maleimide moiety have been developed [23][24][25][26][27][28][29][30][31].…”

Section: Introductionmentioning

confidence: 99%

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Dyes derived from benzo[a]phenoxazine – synthesis, spectroscopic properties, and potential application as sensors for l‐cysteine

Grzelakowska

Kolińska

Zakłos‐Szyda

et al. 2016

Coloration Technology

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Several benzo[a]phenoxazine dyes containing a maleimide moiety have been synthesised and characterised by proton nuclear magnetic resonance spectroscopy and mass spectrometry. The spectroscopic properties, such as absorption and emission spectra, of these dyes -9-maleimido-5H-benzo[a]phenoxazin-5-one (7a), 6-chloro-9-maleimido-5H-benzo[a]phenoxazin-5-one (7b), and 6-bromo-9-maleimido-5H-benzo[a]phenoxazin-5-one (7c)were examined. These compounds were evaluated as potential fluorescent and colorimetric probes for the detection of biothiols. Results show that the studied compounds exhibit colorimetric and fluorescent responses to L-cysteine at pH 7.4. In the presence of L-cysteine, the fluorescence intensity of synthesised dyes is greatly enhanced. The addition of L-cysteine to solutions of dyes 7a to 7c also results in red shifts of their absorption bands. The cytotoxic effect of tested dyes 7a to 7c against human neuroblastoma cells (SH-SY5Y) was determined by MTT assay. The fluorescent response of these compounds to thiols SH-SY5Y was examined. The results show that the tested compounds exhibit fluorescent response in this cell line, and the benzo[a]phenoxazine dyes substituted in the 6-position with a halogen (7b and 7c) are less toxic against cells under experimental conditions than their unsubstituted analogue (7a).

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Section: Studies Of the Spectroscopic Response To Thiolssupporting

confidence: 86%

Section: Studies Of the Spectroscopic Response To Thiolssupporting

confidence: 84%

Section: Studies Of the Spectroscopic Response To Thiolsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Dyes derived from benzo[a]phenoxazine – synthesis, spectroscopic properties, and potential application as sensors for l‐cysteine

Grzelakowska

Kolińska

Zakłos‐Szyda

et al. 2016

Coloration Technology

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Characterization of a novel styrylbenzimidazolium‐based dye and its application in the detection of biothiols

Kolińska

Grzelakowska

2020

Luminescence

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A novel styrylbenzimidazolium dye containing a maleimide group 5 was synthesized and characterized using proton nuclear magnetic resonance spectroscopy and mass spectrometry. The photophysical properties [ultraviolet–visible (UV–vis) light absorption and fluorescence spectra, fluorescence quantum yield, and fluorescence lifetime] were investigated. Spectroscopic characterization of the novel styrylbenzimidazolium‐based dye under various conditions is presented and its usefulness to detect biothiols proved. The addition of biothiols [l‐cysteine (l‐Cys), l‐homocysteine (l‐Hcy), l‐glutathione (l‐GSH)] to compound 5 in phosphate buffer (0.1 M, pH 7.4) containing 10% CH3CN induced a 15–28‐fold enhancement in fluorescence intensity at 410 nm. The limits of detection of compound 5 for l‐Cys, l‐Hcy, and l‐GSH were estimated as 0.114, 0.118, and 0.059 μM, respectively. Evaluation of the cytotoxicity of 5 using the PrestoBlue assay for HeLa cells was also determined. The examined compound revealed a slight cytotoxicity against HeLa cells under experimental conditions.

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Two‐photon Dye‐Based Fluorogenic Organic Nanoparticles as Intracellular Thiols Sensors

Dal Pra,

Daniel,

Recher

et al. 2024

Small Methods

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Optical bioimaging is an ever‐growing field that benefits both from the fast progress of optical instrumentation and modalities, and from the development of light‐emitting probes. The efficacy of molecular fluorescent dyes is crucial, yet hindered by limited brightness and hydrophilicity. Addressing these challenges, self‐stabilized fluorogenic organic nanoparticles only made of pure dyes (dFONs) are introduced in this work. Comprising thiol‐sensitive fluorogenic chromophores, these dFONs exhibit enhanced brightness exclusively in the presence of biological thiols, notably glutathione, overcoming the need for water‐solubilizing moieties. Importantly, these nanoparticles demonstrate large fluorescence and one‐ and two‐photon brightness, enabling sensitive bioimaging of intracellular thiols at micromolar concentrations. Notably, only the pristine fluorogenic nanoparticles can penetrate the cells and does not require to wash the cells before imaging, emphasizing their unique role as dye carriers, fluorogenic probes and ease of use. This work highlights the transformative potential of dFONs in advancing optical bioimaging, paving the way for the use of dFONs not just as tracers, but also now as biosensors and ultimately in the future as biomarkers.

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A triphenylamine as a fluorophore and maleimide as a bonding group selective turn-on fluorescent imaging probe for thiols

Cited by 47 publications

References 43 publications

Dyes derived from benzo[a]phenoxazine – synthesis, spectroscopic properties, and potential application as sensors for l‐cysteine

Dyes derived from benzo[a]phenoxazine – synthesis, spectroscopic properties, and potential application as sensors for l‐cysteine

Characterization of a novel styrylbenzimidazolium‐based dye and its application in the detection of biothiols

Two‐photon Dye‐Based Fluorogenic Organic Nanoparticles as Intracellular Thiols Sensors

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