Highly Selective Fluorescent Probe for Vicinal‐Dithiol‐Containing Proteins and In Situ Imaging in Living Cells

Huang, Chusen; Yin, Qin; Zhu, Weiping; Yang, Yi; Wang, Xin; Qian, Xuhong; Xu, Yufang

doi:10.1002/ange.201101317

Cited by 16 publications

(16 citation statements)

References 42 publications

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“…1 – 3 ). During colocalization studies with ER and lysosome trackers, some localisation within the ER was also observed 23 . Additionally, MitoESq-635 is widely compatible with different cell lines, such as HeLa, MCF7, RAW 264.7, U2OS and primary neuron cells (Supplementary Fig.…”

Section: Resultsmentioning

confidence: 97%

Mitochondrial dynamics quantitatively revealed by STED nanoscopy with an enhanced squaraine variant probe

Yang

et al. 2020

Nat Commun

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Mitochondria play a critical role in generating energy to support the entire lifecycle of biological cells, yet it is still unclear how their morphological structures evolve to regulate their functionality. Conventional fluorescence microscopy can only provide ~300 nm resolution, which is insufficient to visualize mitochondrial cristae. Here, we developed an enhanced squaraine variant dye (MitoESq-635) to study the dynamic structures of mitochondrial cristae in live cells with a superresolution technique. The low saturation intensity and high photostability of MitoESq-635 make it ideal for long-term, high-resolution (stimulated emission depletion) STED nanoscopy. We performed time-lapse imaging of the mitochondrial inner membrane over 50 min (3.9 s per frame, with 71.5 s dark recovery) in living HeLa cells with a resolution of 35.2 nm. The forms of the cristae during mitochondrial fusion and fission can be clearly observed. Our study demonstrates the emerging capability of optical STED nanoscopy to investigate intracellular physiological processes with nanoscale resolution for an extended period of time.

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Section: Resultsmentioning

confidence: 97%

Mitochondrial dynamics quantitatively revealed by STED nanoscopy with an enhanced squaraine variant probe

Yang

et al. 2020

Nat Commun

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“…The synthesis of the target compound 5 is illustrated in Scheme 1. We first commenced the synthesis of compound 2 following the previously reported procedure with a slight modification [24,25] . Briefly, the protection reaction of commercially purchased 6-aminohexanoic acid ( 1 ) with di- tert -butyl dicarbonate (Boc 2 O) in the presence of sodium hydroxide quantitatively provided compound 2 .…”

Section: Methodsmentioning

confidence: 99%

Design, synthesis, and biological evaluation of histone deacetylase inhibitor with novel salicylamide zinc binding group

Kim¹,

Ali²,

Oh³

et al. 2022

Medicine

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Introduction: Histone deacetylases (HDACs) have emerged as important therapeutic targets for various diseases, such as cancer and neurological disorders. Although a majority of HDAC inhibitors use hydroxamic acids as zinc binding groups, hydroxamic acid zinc-binding groups suffer from poor bioavailability and nonspecific metal-binding properties, necessitating a new zinc-binding group. Salicylic acid and its derivatives, well-known for their therapeutic value, have also been reported to chelate zinc ions in a bidentate fashion. This drew our attention towards replacing hydroxamic acid with salicylamide as a zinc-binding group. Methods: In this study, for the first time, compound 5 possessing a novel salicylamide zinc-binding group was synthesized and evaluated biologically for its ability to inhibit various HDAC isoforms and induce acetylation upon α-tubulin and histone H3 among MDA-MB-231 cells. Results: Compound 5 exhibits selective inhibition against class I HDAC isoforms (HDAC1, 2, and 3) over class II and IV HDAC isoforms (HDAC4, 6, and 11). The exposure of MDA-MB-231 cells to compound 5 efficiently induced the acetylation of more histone H3 than α-tubulin, suggesting that compound 5 is a class I selective HDAC inhibitor. Moreover, the molecular docking study indicated that the salicylamide zinc-binding group of compound 5 coordinates the active zinc ion of class I HDAC2 in a bidentate fashion. Conclusion: Overall, salicylamide represents a novel zinc-binding group for the development of class I selective HDAC inhibitors. Graphical abstract:

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“…Based on excited-state intramolecular proton transfer (ESIPT), elegant ratiometric probes were reported. 30,31 Yet, their disadvantage is the low-fluorescence quantum yield of ESIPT-type fluorophores. The limitations of the existing approaches for ratiometric probes prompted us to develop alternative design principles.…”

Section: Introductionmentioning

confidence: 99%

A Monochromophoric Approach to Succinct Ratiometric Fluorescent Probes without Probe-Product Crosstalk

Xin

Guo

et al. 2021

CCS Chem

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Ratiometric probes facilitate quantitative studies via self-calibration and are cherished for bioimaging. Often, a small probe-product spectral separation leads to crosstalk, but the rational development of ratiometric probes with zero probe-product crosstalk remains challenging. Harnessing the recent progress on photophysical modulation of xanthenoid fluorochromes, we propose a powerful and versatile probe design principle, that is, "bridging-group modification," and developed totalROX, a robust probe for monitoring the total cellular oxidative capacity. First, totalRox affirmatively detected the complete set of biorelevant highly oxidative species: per-acids (2 e − ), radicals (1 e − ), nitrosative (NO + ) species, and singlet oxygen ( 1 O 2 ). Nonoxidative or mildly oxidative pro-oxidants, for example, O 2• -, H 2 O 2 , NO, ONOO -, and ClOwere not detected. Second, the absorption/fluorescence maxima of the probe (total-ROX, λ abs /λ em = 425/525 nm) and the detection product (Ox670, λ abs /λ em = 650/675 nm) were separated by ca. 225/150 nm, respectively, which eliminated probe-product crosstalk. Third, it renders the ratiometric signal with a single chromophore and is structurally succinct. TotalROX allowed quantitative analysis and was more sensitive than Amplex Red and CellROX Deep Red, two commercial probes for cell oxidative species. Bioimaging potentials of total-ROX for monitoring cell redox status were exemplified in three different cell lines.

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Highly Selective Fluorescent Probe for Vicinal‐Dithiol‐Containing Proteins and In Situ Imaging in Living Cells

Cited by 16 publications

References 42 publications

Mitochondrial dynamics quantitatively revealed by STED nanoscopy with an enhanced squaraine variant probe

Mitochondrial dynamics quantitatively revealed by STED nanoscopy with an enhanced squaraine variant probe

Design, synthesis, and biological evaluation of histone deacetylase inhibitor with novel salicylamide zinc binding group

A Monochromophoric Approach to Succinct Ratiometric Fluorescent Probes without Probe-Product Crosstalk

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