A highly sensitive and selective fluorescent sensor for detection of sulfide anion based on the steric hindrance effect

Chen, Guanfan; Tang, Mengzhuo; Fu, Xiufang; Cheng, Fenmin; Zou, Xianghua; Wang, Jingpei; Zeng, Rongjin

doi:10.1016/j.molstruc.2017.08.049

Cited by 12 publications

(5 citation statements)

References 31 publications

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“…Sulfide anion is one of the toxic anions in the environment because it is corrosive and flammable [1][2][3]. Prolonged exposure to sulfide ions can cause chronic illnesses, blood disorders, digestive system, respiratory illness, and serious illnesses such as Alzheimer, cancer, diabetes, cardiovascular diseases [3][4], and Down's syndrome [5]. Due to the impacts caused by the presence of sulfide anions in the environment, it is necessary to detect and monitor the sulfide ions, especially in sectors close to the human environment.…”

Section: ■ Introductionmentioning

confidence: 99%

Synthesis of Vanillin-Azine as Colorimetric Chemosensor of Sulfide Anion

Rokhmah

Mardjan²,

Purwono³

2022

Indones. J. Chem.

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Vanillin-azine (VA), (4,4'-((1E,1'E)-hydrazine-1,2-diylidenebis(methane-lylidene))bis(2-methoxyphenol) has been synthesized from vanillin and tested as anion colorimetric chemosensors for sulfide anion. The VA was obtained from a condensation reaction between vanillin and hydrazine hydrate with a mol ratio of 2:1 mol for 24 h at room temperature. The structure was elucidated using FTIR, GC-MS, 1H-NMR, and 13C-NMR spectrometers. The VA compound was examined as a colorimetric chemosensor for sulfide anion over several anions of CN−, F−, Cl−, Br−, I−, N3−, CH3COO−, and NO3−. The structure of the product showed agreement with all spectrometric data. The VA chemosensor tests indicated only selective to S2− anion followed by a color change from colorless to light blue in a DMF:HEPES buffer solution (DMF:HBS) medium (9:1, v/v, 10 mM, pH = 7.4). Filter paper strips can detect S2− anion with a color change from white to yellow. The VA chemosensor has a limit of detection (LOD) of 5.4 × 10−4 M, therefore, the VA chemosensor can be applied to detect S2− anion in tap water.

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Section: ■ Introductionmentioning

confidence: 99%

Synthesis of Vanillin-Azine as Colorimetric Chemosensor of Sulfide Anion

Rokhmah

Mardjan²,

Purwono³

2022

Indones. J. Chem.

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“…503 This turn-on response was also demonstrated in HeLa cells treated with exogenous H 2 S. Chen and Zeng also used this approach with an ortho-functionalized porphyrin to generate 479 with similar optical and responsive properties and increased selectivity attributed to an enhanced steric effect. 504 Expanding to a tetrasubstituted system, Jiang, Li, and Chen reported 480 (TDBP), which responded to both H 2 S and GSH to generate a fluorescent response that was confirmed in HepG2 cells. 505 Expanding to corrole-based systems, Lu reported the p-chlorophenyl 481 (COR-DNBS), phenyl 482 (DPC-DNBS), and naphthyl 483 (NPC-H 2 S) derivatives in separate publications.…”

Section: 4-dinitrobenzenesulfonate (Dnbs) Cleavagementioning

confidence: 97%

“…For example, Zeng reported functionalized porphyrin 478 , which generates a fluorescent response at 653 nm when treated with H 2 S and good selectivity over competing analytes in 50% THF in buffer . This turn-on response was also demonstrated in HeLa cells treated with exogenous H 2 S. Chen and Zeng also used this approach with an ortho -functionalized porphyrin to generate 479 with similar optical and responsive properties and increased selectivity attributed to an enhanced steric effect . Expanding to a tetrasubstituted system, Jiang, Li, and Chen reported 480 (TDBP), which responded to both H 2 S and GSH to generate a fluorescent response that was confirmed in HepG2 cells .…”

Section: Electrophilic H2s Probesmentioning

confidence: 99%

Activity-Based Fluorescent Probes for Hydrogen Sulfide and Related Reactive Sulfur Species

Fosnacht,

Pluth

2024

Chem. Rev.

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Hydrogen sulfide (H 2 S) is not only a well-established toxic gas but also an important small molecule bioregulator in all kingdoms of life. In contemporary biology, H 2 S is often classified as a "gasotransmitter," meaning that it is an endogenously produced membrane permeable gas that carries out essential cellular processes. Fluorescent probes for H 2 S and related reactive sulfur species (RSS) detection provide an important cornerstone for investigating the multifaceted roles of these important small molecules in complex biological systems. A now common approach to develop such tools is to develop "activitybased probes" that couple a specific H 2 S-mediated chemical reaction to a fluorescent output. This Review covers the different types of such probes and also highlights the chemical mechanisms by which each probe type is activated by specific RSS. Common examples include reduction of oxidized nitrogen motifs, disulfide exchange, electrophilic reactions, metal precipitation, and metal coordination. In addition, we also outline complementary activity-based probes for imaging reductant-labile and sulfane sulfur species, including persulfides and polysulfides. For probes highlighted in this Review, we focus on small molecule systems with demonstrated compatibility in cellular systems or related applications. Building from breadth of reported activity-based strategies and application, we also highlight key unmet challenges and future opportunities for advancing activity-based probes for H 2 S and related RSS.

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“…[66][67][68][69] Second, side-chain groups also have many other functions, such as increasing the molecular volume to reduce the impact of molecular accumulation, increasing steric hindrance and compressing the reaction space to increase selectivity, acting as a donor or an acceptor in fluorescence resonance energy transfer (FRET), and improving the physical and dynamic properties of the probe. [70][71][72][73]…”

Section: Porphyrinmentioning

confidence: 99%

New insight into the application of fluorescence platforms in tumor diagnosis: From chemical basis to clinical application

Chen²,

Pan

et al. 2022

Medicinal Research Reviews

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Early and rapid diagnosis of tumors is essential for clinical treatment or management. In contrast to conventional means, bioimaging has the potential to accurately locate and diagnose tumors at an early stage. Fluorescent probe has been developed as an ideal tool to visualize tumor sites and to detect biological molecules which provides a requirement for noninvasive, real-time, precise, and specific visualization of structures and complex biochemical processes in vivo. Rencently, the development of synthetic organic chemistry and new materials have facilitated the development of near-infrared small molecular sensing platforms and nanoimaging platforms. This provides a competitive tool for various fields of bioimaging such as biological structure and function imaging, disease diagnosis, in situ at the in vivo level, and real-time dynamic imaging. This review systematically focused on the recent progress of small molecular near-infrared fluorescent probes and nano-fluorescent probes as new biomedical imaging tools in the past 3-5 years, and it covers the application of tumor biomarker sensing, tumor microenvironment imaging, and tumor vascular imaging, intraoperative guidance and as an integrated platform for diagnosis, aiming to provide

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A highly sensitive and selective fluorescent sensor for detection of sulfide anion based on the steric hindrance effect

Cited by 12 publications

References 31 publications

Synthesis of Vanillin-Azine as Colorimetric Chemosensor of Sulfide Anion

Synthesis of Vanillin-Azine as Colorimetric Chemosensor of Sulfide Anion

Activity-Based Fluorescent Probes for Hydrogen Sulfide and Related Reactive Sulfur Species

New insight into the application of fluorescence platforms in tumor diagnosis: From chemical basis to clinical application

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