Compound, preparation method and application thereof as near-infrared region-II fluorescent probe for detecting pyruvaldehyde

A compound, polyethylene glycol-based technology, applied in the field of compounds, can solve the problems of complicated operation, narrow application range, and cell lysis.

Active Publication Date: 2020-05-26
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these methods have narrow application range, low sensitivity, or need to lyse cells, and the operation is cumbersome and limited (Anal.Chim.Acta.2012, 751:66-70; Anal.Bioanal.Chem.2012,403:2577-2581 ; Anal. Methods. 2015, 7: 2386–2390.)

Method used

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  • Compound, preparation method and application thereof as near-infrared region-II fluorescent probe for detecting pyruvaldehyde
  • Compound, preparation method and application thereof as near-infrared region-II fluorescent probe for detecting pyruvaldehyde
  • Compound, preparation method and application thereof as near-infrared region-II fluorescent probe for detecting pyruvaldehyde

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] Embodiment 1, the synthesis of compound S1-1

[0059]

[0060] Compound C1 was synthesized by reference method (Chem. Sci., 2016, 7:6203-6207). Then compound C1 (100 mg, 0.06 mmol) was dissolved in 3 mL of acetic acid, Fe powder (100 mg, 1.79 mmol) was added, and the temperature of the reaction solution was raised to 100° C., and reacted for 6 h under nitrogen protection. After the reaction was completed, the pH value of the reaction solution was adjusted to 7-8 with saturated sodium bicarbonate solution, extracted three times with dichloromethane, and the organic phases were combined. Washed with saturated brine and dried over anhydrous sodium sulfate. After suction filtration, the filtrate was concentrated under reduced pressure, and the crude product was separated by column chromatography to obtain 55 mg of yellow solid compound S1-1, with a yield of 57%. 1 HNMR (300MHz, CDCl 3 )δ7.50(d, J=8.49 Hz, 4H), 7.32(m, 4H), 7.07(m, 20H), 4.19(t, J=8.43Hz, 8H), 2.92(m, ...

Embodiment 2

[0061] Embodiment 2, the synthesis of compound S1-2

[0062]

[0063] Compound S1-1 (10 mg, 0.0066 mmol) was dissolved in an appropriate amount of dichloromethane, added trifluoroacetic acid (dichloromethane: trifluoroacetic acid = 10:1, v / v), and stirred at room temperature for 5 h. The reaction solution was concentrated under reduced pressure, and the crude product was separated by column chromatography to obtain 4 mg of compound S1-2 as a yellow solid, with a yield of 54%. ESI-MS theoretical value is C 62 h 52 N 6 o 8 S 3 :1104.3, measured value is 1105.3[M+H] + .

Embodiment 3

[0064] Embodiment 3, the synthesis of compound S1-3

[0065]

[0066] Compound A2 was synthesized in two steps: 1,4-dibromo-2,3-dinitrobenzothiazole (100.0mg, 0.26mmol), tributyl (2,3-dihydrothieno[3,4-B ]-[1,4]dioxin-5-yl)stannane (336.0 mg, 0.78 mmol) and bistriphenylphosphine palladium dichloride (52.0 mg, 0.074 mmol) were added to 8.0 mL of distilled toluene, Nitrogen protection, reflux reaction for 12h. After the reaction was detected by TLC, water and ethyl acetate were added for extraction, and the organic layer was washed with water and saturated brine in sequence, and dried over anhydrous sodium sulfate. After suction filtration, the filtrate was concentrated under reduced pressure, and the crude product was separated by column chromatography to obtain 126.6 mg of compound i as an orange solid, with a yield of 96%. 1 HNMR (300MHz, CDCl 3 )δ6.77(s,2H), 4.22(dd,J=11.5,5.5Hz,8H). 13 CNMR (125MHz, CDCl 3 )δ152.63, 143.07, 142.52, 141.21, 120.28, 105.49, 104.61, 64...

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Abstract

The invention provides a compound, a preparation method thereof and an application of the compound as a near-infrared region-II fluorescent probe for detecting pyruvaldehyde. The compound has a structure as shown in a general formula I, and has good response to pyruvaldehyde. Therefore, the compound is expected to be used as a near-infrared region-II fluorescent probe for in-vivo detection of pyruvaldehyde, such as detection of pyruvaldehyde in blood, lymph nodes and tumors.

Description

technical field [0001] The invention relates to a class of compounds, a preparation method thereof and the application thereof as a fluorescent probe in the second near-infrared region for detecting methylglyoxal. Background technique [0002] Methylglyoxal (MGO) is a chemically active α-ketoaldehyde compound, which is the active dicarbonyl metabolite of glucose, fatty acid and amino acid in the body. Methylglyoxal is a powerful glycosylation reagent that can glycosylate a variety of biological macromolecules, such as proteins and DNA, to produce toxic end products (Advanced glycation endproducts, AGEs), which lead to protein dysfunction, activation of membrane receptors and triggers pro-inflammatory signals. Literature reports indicate that MGO is closely related to senile diseases, diabetic complications and chronic inflammation (DrugMetab.DrugInteract.2008,23:125-150; Endocrine.2013,43:472-484; Diabetologia.2001,44:129-146; AminoAcids. 2012, 42:1133-1142.). In patients...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/08C07D417/14C07D495/04C07D519/00C09K11/06G01N21/64C08G65/26C08G65/337A61K49/00
CPCC07F7/0814C07F7/083C07D417/14C07D495/04C07D519/00C09K11/06G01N21/643G01N21/6428G01N21/6486C08G65/2639C08G65/337A61K49/0021C09K2211/1007C09K2211/1011C09K2211/1029C09K2211/1051C09K2211/1092C09K2211/1483G01N2021/6432
Inventor 丁春勇徐志爱张文吉爱艳王凤阳于海军张翱
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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