The design and synthesis of novel “turn-on” fluorescent probes to visualize monoamine oxidase-B in living cells

Xiang, Yumi; He, Bingyong; Li, Xuefeng; Zhu, Qing

doi:10.1039/c3ra22789h

Cited by 20 publications

(13 citation statements)

References 21 publications

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“…A vanillic acid amide had the best antifungal activity result, so five derived esters (compounds 23 – 27 ) and five derived ethers (compounds 28 – 32 ) of this vanillic acid amide ( 15 ) were prepared using reaction methods for replacing the vanillic ring OH group with an ether or ester chain. All ester and ether derivatives are reported for the first time in the literature and their spectroscopic data were in agreement with the literature data of structurally similar compounds [18,19,20,21,22,23,24,25,26].…”

Section: Resultssupporting

confidence: 88%

“…The extraction solution was washed with distilled water (3 × 10 mL), and then with 10% NaOH (10 mL). The solution was treated with Na 2 SO 4 , filtered, and concentrated by rotary evaporation [24]. The product was purified by silica gel column chromatography using EtOAc:Hex (65:35) as the mobile phase system to afford a colorless oil; yield: 75% (106 mg), IR ν max (cm −1 ): 3350 (OH) 3016 (CH sp 2 ), 1645 (C=O), 1600 and 1489 (aromatic C=C), 1014 (stretching C-Cl).…”

Section: Methodsmentioning

confidence: 99%

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Synthesis, Antifungal Evaluation and In Silico Study of N-(4-Halobenzyl)amides

et al. 2016

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A collection of 32 structurally related N-(4-halobenzyl)amides were synthesized from cinnamic and benzoic acids through coupling reactions with 4-halobenzylamines, using (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP) as a coupling agent. The compounds were identified by spectroscopic methods such as infrared, 1 H-and 13 C-Nuclear Magnetic Resonance (NMR) and high-resolution mass spectrometry. The compounds were then submitted to antimicrobial tests by the minimum inhibitory concentration method (MIC) and nystatin was used as a control in the antifungal assays. The purpose of the tests was to evaluate the influence of structural changes in the cinnamic and benzoic acid substructures on the inhibitory activity against strains of Candida albicans, Candida tropicalis, and Candida krusei. A quantitative structure-activity relationship (QSAR) study with KNIME v. 3.1.0 and Volsurf v. 1.0.7 softwares were realized, showing that descriptors DRDRDR, DRDRAC, L4LgS, IW4 and DD2 influence the antifungal activity of the haloamides. In general, 10 benzamides revealed fungal sensitivity, especially a vanillic amide which enjoyed the lowest MIC. The results demonstrate that a hydroxyl group in the para position, and a methoxyl at the meta position enhance antifungal activity for the amide skeletal structure. In addition, the double bond as a spacer group appears to be important for the activity of amide structures.

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Section: Resultssupporting

confidence: 88%

Section: Methodsmentioning

confidence: 99%

Synthesis, Antifungal Evaluation and In Silico Study of N-(4-Halobenzyl)amides

et al. 2016

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“…10 Fluorescent probe offers a unique approach for visualizing morphological details of tissues with subcellular resolution and has become a powerful tool for manipulating and investigating living cells and even animals. [11][12][13][14] There are different kinds of uorescent probes with various skeleton structure, including rhodamine, 15 BODIPY, 16 uorescein, 17 tricarbocyanine, 18 benzo[a]phenoxazine, 19 coumarin 20 etc. From these uorophores, some special probes with pH sensitivity can be designed and synthesized by changing functional groups to these skeletons.…”

Section: Introductionmentioning

confidence: 99%

A novel coumarin derivative as a sensitive probe for tracing intracellular pH changes

Liu

Jiang

et al. 2015

RSC Adv.

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“…In a further study, they reported fluorescein derivatives 13 and their use for bioimaging. 46 Probe 13a, however, gave only about three times higher fluorescence enhancement to MAO-B over MAO-A (K m (13a/MAO-A) = 257.9 μM, K m (13a/MAO-B) = 47.1 μM).…”

Section: −1mentioning

confidence: 99%

Fluorescent Probes for Analysis and Imaging of Monoamine Oxidase Activity

Kim¹,

Jun²,

Ahn³

2014

Bulletin of the Korean Chemical Society

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Monoamine oxidases catalyze the oxidative deamination of dietary amines and amine neurotransmitters, and assist in maintaining the homeostasis of the amine neurotransmitters in the brain. Dysfunctions of these enzymes can cause neurological and behavioral disorders including Parkinson's and Alzheimer's diseases. To understand their physiological roles, efficient assay methods for monoamine oxidases are essential. Reviewed in this Perspective are the recent progress in the development of fluorescent probes for monoamine oxidases and their applications to enzyme assays in cells and tissues. It is evident that still there is strong need for a fluorescent probe with desirable substrate selectivity and photophysical properties to challenge the much unsolved issues associated with the enzymes and the diseases.

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The design and synthesis of novel “turn-on” fluorescent probes to visualize monoamine oxidase-B in living cells

Cited by 20 publications

References 21 publications

Synthesis, Antifungal Evaluation and In Silico Study of N-(4-Halobenzyl)amides

Synthesis, Antifungal Evaluation and In Silico Study of N-(4-Halobenzyl)amides

A novel coumarin derivative as a sensitive probe for tracing intracellular pH changes

Fluorescent Probes for Analysis and Imaging of Monoamine Oxidase Activity

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