A turn-on NIR fluorescent probe for the detection of homocysteine over cysteine

Zhang, Jian; Jiang, Xin‐Dong; Shao, Xiangmin; Zhao, Jiuli; Su, Yajun; Xi, Dongmei; Yu, Haifeng; Yue, Shuai; Xiao, Lin-Jiu; Zhao, Weili

doi:10.1039/c4ra08771b

Cited by 46 publications

(17 citation statements)

References 53 publications

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“…Our group introduced the formyl group to the meso position of ac onformationally restricted BODIPY skeleton to establish turn-onf luorescent probe 34 for Cys/Hcy. [72] The time-dependent measurements demonstrated that the probe reacted faster with Hcy than Cys and the kinetic modes provided ap otential application to discriminateH cy from Cys. Hao, Jiao, and co-workersr eported 2-formyl BODIPY derivative 35.…”

Section: Probesf or Sulfhydryl Amino Acidmentioning

confidence: 95%

BODIPY‐Based Fluorescent Probes for Biothiols

Zhang

Wang

et al. 2020

Chemistry A European J

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191

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Fluorescent probes for biothiols have aroused increasing interest owing to their potential to enable better understanding of the diverse physiological and pathological processes related to the biothiol species. BODIPY fluorophores exhibit excellent optical properties, which can be readily tailored by introducing diverse functional units at various positions of the BODIPY core. In the present review, the development of fluorescent probes based on BODIPYs for the detection of biothiols are systematically summarized, with emphasis on the preferable detection of individual biothiols, as well as simultaneous discrimination among cysteine (Cys), homocysteine (Hcy), reduced glutathione (GSH). In addition, organelle‐targeting probes for biothiols are also highlighted. The general design principles, various recognition mechanisms, and biological applications are elaboratively discussed, which could provide a useful reference to researchers worldwide interested in this area.

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Section: Probesf or Sulfhydryl Amino Acidmentioning

confidence: 95%

BODIPY‐Based Fluorescent Probes for Biothiols

Zhang

Wang

et al. 2020

Chemistry A European J

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191

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“…However, fluorescence quenching probes suffer from low signal-to-noise ratio, so that fluorescence probes using "turn-on" mode are preferred. But only a few aldehyde-functionalized "turn-on" probes have been reported for selective detection of Hcy, such as pyrene-based dyes [20], and BODIPY [21]. For example, Wang and coworkers studied a dansyl azide analogue fluorescent probe for the selective detection of Hcy [22].…”

Section: Introductionmentioning

confidence: 99%

Aldehyde bearing bis-cyclometalated Ir(III) complex as selective photoluminescence turn-on probe for imaging intracellular homocysteine

Gao

Zhao

et al. 2017

Sensors and Actuators B: Chemical

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A new photoluminescence (PL) turn-on probe based on aldehyde bearing bis-cyclometalated Ir(III) complex, [Ir(bt) 2 phen-CHO] + PF 6-(1), is synthesized and applied to imaging homocysteine (Hcy) in living cells. The probe 1 is readily prepared by using 2-phenylbenzothiazole (bt) as main ligand and 1,10-phenanthroline-5-carboxaldehyde (phen-CHO) as ancillary ligand. Probe 1 displayed excellent selective PL enhancement in response to Hcy in neutral buffer solution based on aldehyde group cyclization reaction. The increased PL intensity of probe 1 is directly proportional to the concentration of Hcy in the range of 10 μM to 500 μM with a detection limit of 4.6 μM. More importantly, probe 1 can highly discriminate Hcy from cysteine (Cys), which is agreed with the higher luminescent quantum yield of the adduct of probe 1 and Hcy (1-Hcy, 0.46) compared with that of probe 1 and Cys (1-Cys, 0.05) in 10 mM phosphate buffer solution (pH 7.4). Furthermore, the probe 1 has appreciable cell permeability and low cytotoxicity and has been successfully applied to selectively imaging Hcy in living cells. The superior properties of the probe 1 make it of great potential use for studying the effects of Hcy in other biosystems.

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“…As an alternative to these classical techniques, in the past two decades, a number of chromo-fluorogenic probes for biothiol detection have been reported [22][23][24]. Most of the described examples are based on the chemodosimeter approach and are synthesized taking into account the nucleophilic character of thiol moieties in these biomolecules [25][26][27][28][29][30][31]. Also, the displacement approach has been extensively used to design biothiol selective chromo-fluorogenic probes.…”

Section: Introductionmentioning

confidence: 99%

2,4,5-Triaryl imidazole probes for the selective chromo-fluorogenic detection of Cu(II). Prospective use of the Cu(II) complexes for the optical recognition of biothiols

et al. 2019

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a b s t r a c tThe sensing behaviour toward metal cations and biothiols of two 2,4,5-triarylimidazole probes (3a and 3b) is tested in acetonitrile and in acetonitrile-water. In acetonitrile the two probes present charge-transfer absorption bands in the 320-350 nm interval. Among all cations tested only Cu(II) is able to induce bathochromic shifts of the absorption band in the two probes, which is reflected in marked colour changes. Colour modulations are ascribed to the formation of 1:1 Cu(II)-probe complexes in which the cation interacts with the imidazole acceptor heterocycle. Besides, the two probes present intense emission bands (at 404 and 437 nm for 3a and 3b respectively) in acetonitrile that are quenched selectively by Cu(II). Probe 3a is soluble in acetonitrile-water 1:1 (v/v) and Cu(II) also induces bathochromic shifts of the absorption bands. Moreover, the emission bands of probe 3a in this mixed aqueous solutions is quenched in the presence of Cu(II). The potential use of the 1:1 complex formed between 3a and Cu (II) for the chromo-fluorogenic detection of biothiols (GSH, Cys and Hcy) in aqueous environments is also tested. At this respect, addition of GSH, Cys and Hcy to acetonitrile-water 1:1 v/v solutions of 3a-Cu(II) complex induces a hypsochromic shift of the visible band (reflected in a bleaching of the solutions) with a marked emission increase at 470 nm. (M.M.M. Raposo), rmaez@ qim.upv. es (R. Martínez-Máñez).

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A turn-on NIR fluorescent probe for the detection of homocysteine over cysteine

Abstract: A BODIPY-based turn-on NIR fluorescent probe containing a partially exposed aldehyde group at the meso position for the detection of homocysteine over cysteine was developed. Such a probe is potentially useful for the discrimination of Hcy from Cys.

Cited by 46 publications

References 53 publications

BODIPY‐Based Fluorescent Probes for Biothiols

BODIPY‐Based Fluorescent Probes for Biothiols

Aldehyde bearing bis-cyclometalated Ir(III) complex as selective photoluminescence turn-on probe for imaging intracellular homocysteine

2,4,5-Triaryl imidazole probes for the selective chromo-fluorogenic detection of Cu(II). Prospective use of the Cu(II) complexes for the optical recognition of biothiols

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