Recent progress in the development of fluorescent probes for detection of biothiols

Dai, Jianan; Ma, Chenggong; Zhang, Ping; Fu, Yongqian; Shen, Baolong

doi:10.1016/j.dyepig.2020.108321

Cited by 156 publications

(54 citation statements)

References 82 publications

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“…Cysteine (Cys) for example is linked to liver damage, slow growth, or edema, while homocysteine (Hcy) is associated with cardiovascular and Alzheimer’s disease, and H 2 S is linked to colorectal cancer [ 221 , 222 , 223 ]. Given their importance in cell metabolism fluorescent probes have been developed to track the concentration of biothiols in real time with high sensitivity and selectivity [ 224 ].…”

Section: Applicationsmentioning

confidence: 99%

Recent Progress in Small Spirocyclic, Xanthene-Based Fluorescent Probes

2020

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The use of fluorescent probes in a multitude of applications is still an expanding field. This review covers the recent progress made in small molecular, spirocyclic xanthene-based probes containing different heteroatoms (e.g., oxygen, silicon, carbon) in position 10′. After a short introduction, we will focus on applications like the interaction of probes with enzymes and targeted labeling of organelles and proteins, detection of small molecules, as well as their use in therapeutics or diagnostics and super-resolution microscopy. Furthermore, the last part will summarize recent advances in the synthesis and understanding of their structure–behavior relationship including novel computational approaches.

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Section: Applicationsmentioning

confidence: 99%

Recent Progress in Small Spirocyclic, Xanthene-Based Fluorescent Probes

2020

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“…Mitochondria are small subcellular organelles that generate adenosine triphosphate (ATP) to power various cell functions in all eukaryotic cells [ 1 , 2 , 3 , 4 ]. Mitochondria also control homeostasis and redox signaling and regulate cell apoptosis and death [ 1 , 2 , 3 , 4 ]. An alkaline pH ≈ 8.0 is essential in mitochondria to sustain the proton motive potential during the synthesis of ATP [ 5 , 6 ].…”

Section: Introductionmentioning

confidence: 99%

“…Mitochondria are small subcellular organelles that generate adenosine triphosphate (ATP) to power various cell functions in all eukaryotic cells [1][2][3][4]. Mitochondria also control homeostasis and redox signaling and regulate cell apoptosis and death [1][2][3][4].…”

Section: Introductionmentioning

confidence: 99%

Ratiometric Near-Infrared Fluorescent Probes Based on Hemicyanine Dyes Bearing Dithioacetal and Formal Residues for pH Detection in Mitochondria

et al. 2021

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Ratiometric near-infrared fluorescent probes (AH+ and BH+) have been prepared for pH determination in mitochondria by attaching dithioacetal and formal residues onto a hemicyanine dye. The reactive formyl group on probe BH+ allows for retention inside mitochondria as it can react with a protein primary amine residue to form an imine under slightly basic pH 8.0. Probes AH+ and BH+ display ratiometric fluorescent responses to pH changes through the protonation and deprotonaton of a hydroxy group in hemicyanine dyes with experimentally determined pKa values of 6.85 and 6.49, respectively. Calculated pKa values from a variety of theoretical methods indicated that the SMDBONDI method of accounting for solvent and van der Waals radii plus including a water molecule located near the site of protonation produced the closest overall agreement with the experimental values at 7.33 and 6.14 for AH+ and BH+ respectively.

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“…Fluorescent probes have attracted wide attention due to their high selectivity and sensitivity, real-time detection, noninvasiveness, and biocompatibility characteristics. [10][11][12][13] In the development of a uorescent probe for biothiol sensing, the design strategies are mainly focused on Michael addition, [14][15][16] nucleophilic cleavage-cyclization, [17][18][19] metal coordination complex-displacement, [20][21][22] and nucleophilic aromatic substitution (SNAr). [23][24][25][26] Giving the strong nucleophilicity of biothiols, especially their corresponding deprotonated thiolate anion, it is desirable to introduce a strong electron-withdrawing group as a biothiol recognition site to a uorophore platform.…”

Section: Introductionmentioning

confidence: 99%