Mitochondrion-targeting near-infrared fluorescent probe for detecting intracellular nanomolar level hydrogen sulfide with high recognition rate

Zhang, Kaiquan; Meng, Jiaqi; Bao, Weier; Liu, Ming; Wang, Xuefei; Zhang, Tian

doi:10.1007/s00216-020-03086-6

Cited by 18 publications

(10 citation statements)

References 40 publications

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“…13C NMR analysis confirms the structures as the number of carbon and the chemical shift fitting the suggested compounds, for the monosaccharide de-rivatives (3,5). The sugar aldehyde carbons appear at about 188 while indole aldehyde appears at 187, the 2NH-CH=C carbon list at 177-179, CH=N carbon located at about 153-155, aromatic carbons in between 110-132, sugar carbons appear from about 50-75, CH3-C-CH3 carbon and the two groups of methyl for the indole moiety at about 20-22 (See Figures S3 and S4).…”

Section: Synthesissupporting

confidence: 56%

“…Guillermo O. Menéndez and others presented water soluble and fluorescent biotinylated probe derived from a carbocyanine dye from benzoindole (4). Kaiquan Zhang et al used benzoindole to developed a new type of fluorescent probe (QcyCHO) featured with H2S-triggered off-toon near-infrared (NIR) fluorescence (5). Ludmila A. Oparina and coworkers reported the reaction of 3Hindoles with tertiary propargylic alcohols to give functionalized dihydrooxazolo [3,2-a]indoles (6).…”

Section: Introductionmentioning

confidence: 99%

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New Bioactive Aromatic Heterocyclic Macromolecules with Monosaccharide Core

MAHMOOD¹,

Salman

ABD

2022

Journal of the Turkish Chemical Society Section A: Chemistry

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1,1,2-trimethyl-1H-benzo[e]indole is an important heterocyclic compound, its available in reasonable price and can easily modified to make a good intermediate for other derivatives. That is quite enough reasons to use as starting material for a new series of compounds with other biomolecules such as monosaccharides after simple modification. The target molecules show biological activity. So, the current work is aiming to improve the activity and the properties of the benzo indole by attaching with a naturally occurring, and biodegradable compounds represented by 2-deoxy-2-amino -d-glucose and 6-deoxy-6-amino-d-glucose to synthesis both mono and di-saccharides derivatives of benzo indole. Two steps synthesis were used for mono-saccharide derivatives and three steps for di-saccharide derivatives, the first is the functionalization of 1,1,2-trimethyl-1H-benzo[e]indole [1] via the reaction with POCl3 to produce 2-(1,1-dimethyl-1H-benzo[e]indol-2(3H)-ylidene) malonaldehyde [2] with two aldehydes reaction centers, while in the second step the latter was coupled with sugar via amino groups to get the two monosaccharide derivatives [3,5], while the disaccharides molecules [4,6] taken one more step with harder conditions to overcome the steric hindrance at the other reaction center. The purity and characterization of the target molecules was confirmed using spectroscopy methods including 1H NMR and 13 NMR. The synthesized compound shows a good biological activity as antibacterial antifungal.

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Section: Synthesissupporting

confidence: 56%

Section: Introductionmentioning

confidence: 99%

New Bioactive Aromatic Heterocyclic Macromolecules with Monosaccharide Core

MAHMOOD¹,

Salman

ABD

2022

Journal of the Turkish Chemical Society Section A: Chemistry

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“…Cys11 showed lower K m toward GSSH compared to H 2 S. Third, the intracellular RSS is around 100 μM–400 μM; whereas, H 2 S is 15 μM–50 μM. Other studies reported that intracellular H 2 S is even low to 10 nM–30 nM quantified with different methods [ 27 , 43 , 44 ]. Fourth, RSS is more stable than H 2 S in the cell [ 45 ], the latter easily releases out as gas; therefore, RSS provides a relatively constant substrate reservoir for Cys11.…”

Section: Discussionmentioning

confidence: 93%

Sulfide-quinone oxidoreductase is required for cysteine synthesis and indispensable to mitochondrial health

et al. 2021

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Mitochondrial dysfunction is related to common age-related disorders, including neurodegenerative diseases, metabolic syndrome, and carcinogenesis. Therefore, maintaining the functionality and integrity of mitochondria is important for human health. Herein, we found that sulfide:quinone oxidoreductase (Sqr), which oxidizes hydrogen sulfide to reactive sulfur species (RSS), was indispensable to mitochondria health in the eukaryotic model microorganism Schizosaccharomyces pombe . Sqr knock-out led to morphological changes and functional deficiencies of mitochondria and apoptosis in S. pombe . The Sqr knock-out strain displayed the same phenotypes as the cysteine-synthesis-deficient strain, and cysteine addition complemented the effects caused by Sqr knock-out. In S. pombe , Sqr was the main RSS producer in mitochondria, and RSS instead of H 2 S was used by cysteine synthase to synthesize cysteine. This finding rewrites the cysteine biosynthesis route in S. pombe and may also in other eukaryotes and prokaryotes, and highlights the importance of cysteine and RSS in maintaining mitochondrial health.

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“…[1][2][3] Numerous research works have revealed that H 2 S is considered to be a third endogenous gaseous transmitter aer nitric oxide (NO) and carbon monoxide (CO). [4][5][6] As a vital antioxidant molecule, H 2 S can make an important contribution to the regulation of blood vessels and inhibition of apoptosis when present at an appropriate concentration. [7][8][9] Reports in the literature have suggested that the level of intracellular H 2 S can be signicantly upregulated during inammatory events.…”

Section: Introductionmentioning

confidence: 99%