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Fluorescent probe based on 2-styryl indole salt type derivative long-wave emission for distinguishable detection on Cys/Hcy and application of florescent probe

A fluorescent probe and styryl technology, which is applied in the distinguishable detection of Cys/Hcy fluorescent probe based on long-wave emission of 2-styryl indole salt derivatives and its application field, which can solve the problem of inability to distinguish and identify Cys/Hcy , the synthesis route is complex, and the rapid detection is not possible, so as to achieve the effect of easy separation and purification, simple synthesis process and good sensitivity

Active Publication Date: 2019-12-03
BOHAI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] In recent years, researchers have designed and developed many fluorescent probes for in vitro and in vivo detection of biothiols (including Hcy, Cys and GSH), which have good selectivity, such as Org.Biomol.Chem., (2019) ,17,1436-1441; Tetrahedron,(2017),73,6651-6656, but its synthetic route is relatively complex; Dyes Pigm.,(2018),158,151-156; New J.Chem.,(2018),42, 18172-18181, but its emission wavelength is shorter; Biosensors and Bioelectronics, (2016), 81, 341-348; CN106588912; cannot distinguish Cys / Hcy; Talanta, (2016), 146, 41-48; Analyst, 2019, 144, 3676 -3684; cannot detect quickly
It can be seen that the existing reported probes all have certain defects. At the same time, due to the similarity in structure and reaction ability of Hcy, Cys and GSH, it is still a challenging task to distinguish and detect them.

Method used

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  • Fluorescent probe based on 2-styryl indole salt type derivative long-wave emission for distinguishable detection on Cys/Hcy and application of florescent probe
  • Fluorescent probe based on 2-styryl indole salt type derivative long-wave emission for distinguishable detection on Cys/Hcy and application of florescent probe
  • Fluorescent probe based on 2-styryl indole salt type derivative long-wave emission for distinguishable detection on Cys/Hcy and application of florescent probe

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] The specific synthesis steps of fluorescent probe L are as follows:

[0034]

[0035] Compound 1 (487.17 mg, 1 mmol), 4-chloro-7-nitrobenzo-2-oxa-1,3-oxadiazole (139.46 mg, 1.2 mmol), triethylamine (101 mg, 0.1 mmol) were dissolved Yu Qian CH 2 Cl 2 (20 mL), stirred at room temperature for 6 hours. Then water was added, the mixture was extracted with ethyl acetate, washed with anhydrous Na 2 SO 4 The organic layer was dried, the solvent was removed, and the crude product was purified by column chromatography using methanol / dichloromethane (1:50, v / v) as eluent to obtain compound L (184 mg, 34.9%). 1 H NMR (400MHz, DMSO-d 6 )δ8.69(d, J=8.3Hz, 1H), 8.40(d, J=9.2Hz, 1H), 8.13(d, J=15.7Hz, 1H), 7.73(t, J=7.5Hz, 2H) ,7.54(td,J=7.7,1.3Hz,1H),7.46(t,J=7.5Hz,1H),7.36(d,J=15.7Hz,1H),6.98(dd,J=9.2,2.4Hz, 2H), 6.95(d, J=2.4Hz, 1H), 4.44(q, J=7.2Hz, 2H), 3.56(q, J=7.0Hz, 4H), 1.46(s, 6H), 1.30(t, J=7.2Hz, 3H), 1.17(t, J=7.0Hz, 6H).

[0036]13 C NMR (101MHz, DMSO-d 6 )δ...

Embodiment 2

[0039] The specific synthesis steps of fluorescent probe L are as follows:

[0040] Compound 1 (487.17 mg, 1 mmol), 4-chloro-7-nitrobenzo-2-oxa-1,3-oxadiazole (174.32 mg, 1.5 mmol), triethylamine (303 mg, 0.3 mmol) were dissolved Yu Qian CH 2 Cl 2 (20 mL), stirred at room temperature for 9 hours. Then water was added, the mixture was extracted with ethyl acetate, washed with anhydrous Na 2 SO 4 The organic layer was dried, the solvent was removed, and the crude product was purified by column chromatography using methanol / dichloromethane (1:80, v / v) as eluent to obtain compound L (150 mg, 28.6%). Fluorescent probe L of this embodiment 1 H NMR spectrum and 13 C NMR spectrum as figure 1 and figure 2 . HRMS (ESI+) Calcd for C 30 h 32 N 5 o 4 [M-I] + :526.2449,found:526.2713.

Embodiment 3

[0042] The specific synthesis steps of fluorescent probe L are as follows:

[0043] Compound 1 (487.17 mg, 1 mmol), 2 4-chloro-7-nitrobenzo-2-oxa-1,3-oxadiazole (232.43 mg, 2 mmol), triethylamine (505 mg, 0.5 mmol) were dissolved Yu Qian CH 2 Cl 2 (20 mL), the mixture was stirred at room temperature for 12 hours. Then water was added, the mixture was extracted with ethyl acetate, washed with anhydrous Na 2 SO 4 The organic layer was dried, the solvent was removed, and the crude product was purified by column chromatography using methanol / dichloromethane (1:100, v / v) as eluent to obtain compound L (113 mg, 21.5%). Fluorescent probe L of this embodiment 1 H NMR spectrum and 13 C NMR spectrum as figure 1 and figure 2 . HRMS (ESI+) Calcd for C 30 h 32 N 5 o 4 [M-I] + :526.2449,found:526.2713.

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Abstract

The invention discloses a fluorescent probe based on 2-styryl indole salt type derivative long-wave emission for distinguishable detection on Cys / Hcy and application of the florescent probe. The structural formula of the fluorescent probe L is shown in the specification. The fluorescent probe L is prepared from a 2-styryl indole salt as a substrate together with 4-chloro-7-nitrobenzo-2-oxa-1,3-diazole and triethylamine through gentle and simple reaction and has long-wave emission. The fluorescent probe L is simple in synthesis step, long in long-wave emission, short in response time, only capable of recognizing Cys / Hcy in a water-containing medium, capable of implementing distinguishable detection on Cys / Hcy, good in sensitivity and applicable to detection for purposes of non-disease diagnosis and non-disease treatment in cells.

Description

technical field [0001] The invention relates to a fluorescent probe for distinguishable detection of Cys / Hcy based on long-wave emission of 2-styryl indole salt derivatives and an application thereof. Background technique [0002] Cysteine ​​(Cys), homocysteine ​​(Hcy) and reduced glutathione (GSH) are common biothiols in living organisms and play important roles in various physiological and pathological processes, among which Cys is the precursor of GSH, involved in protein synthesis, detoxification and metabolism. Hcy has been identified as an independent risk factor for many diseases, and its small increase (over 15 μM) can lead to severe homocysteinemia. GSH, as the most abundant thiol in cells, plays an important role in combating oxidative stress and maintaining redox homeostasis. At present, the common classical methods for the detection of three biothiols include electrochemical method, colorimetric method, methylene blue method and gas chromatography. Compared wi...

Claims

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Application Information

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IPC IPC(8): C07D413/12C09K11/06G01N21/64
CPCC07D413/12C09K11/06G01N21/6428C09K2211/1029C09K2211/1048C09K2211/1007
Inventor 徐永霞朱文慧李秋莹赵洪雷周诗怡钟克利汤立军
Owner BOHAI UNIV
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