Acid-resistant photo-controlled fluorescent molecular switch in aqueous solution, and synthesis method thereof

A technology of fluorescent molecules and synthesis methods, applied in the field of acid-resistant light-controlled fluorescent molecular switches and their synthesis, can solve the problems of inability to accurately detect metal cations, interference of experimental results, and limited applications, and achieve the effect of reducing background fluorescence interference

Active Publication Date: 2019-09-24
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there is also a shortcoming of this type of molecule, which seriously limits its application in the field of fluorescent dyes, that is, protonic acid (H + ) can also open the rhodamine amide spiro ring, which will cause great interference to the experimental results
There are many acidic environments in cells (such as lysosomes, acidic proteins, etc.), when rhodamine spiroamide dyes are used in these acidic environments, the fluorescent signal generated by the acid ring opening will seriously interfere with the detection results and even lead to It is completely wrong, so fluorescent probes based on such dyes in acidic environments are still unable to accurately detect metal cations, and they will be further applied to many fields such as sensing and detection of biological and chemical substances

Method used

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  • Acid-resistant photo-controlled fluorescent molecular switch in aqueous solution, and synthesis method thereof
  • Acid-resistant photo-controlled fluorescent molecular switch in aqueous solution, and synthesis method thereof
  • Acid-resistant photo-controlled fluorescent molecular switch in aqueous solution, and synthesis method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] When R 1 = R 2 When =H, its molecular (P1) synthesis route and product structure are as follows:

[0028]

[0029] Synthesis steps and characterization: Dissolve 3-nitrorhodamine (2mmol, 0.974g) and aminohexapolyethylene glycol (2mmol, 0.562g) in absolute ethanol (5mL), heat up to 78°C and reflux, stir for 4 hours The solvent was distilled off under reduced pressure, and the product was separated and purified by column chromatography (silica gel, dichloromethane / methanol, 10:1 v / v) to obtain a pale yellow viscous liquid (1.42 g, 95%). Then this liquid product was all dissolved in methanol (5mL), stirred under hydrogen atmosphere and palladium carbon (10%wt) catalysis for 1 hour, suction filtered and got the filtrate, obtained the final white viscous liquid product P1 ( 1.35 g, 99%).

[0030] The product was subjected to NMR ( figure 1 ) and mass spectrometric characterization: 1 H NMR (400MHz, CDCl 3 )δ7.14(t,J=7.7Hz,1H),6.58–6.50(m,3H),6.38–6.26(m,5H),3.74–3....

Embodiment 2

[0034] When R 1 = H, R 2 =CH 3 When, its molecular (P2) synthesis route and product structure are as follows:

[0035]

[0036] Synthesis steps and characterization: 3-Nitrorhodamine (0.24g, 0.5mmol) and aminohexapolyethylene glycol methyl ether (0.14g, 0.5mmol) were dissolved in absolute ethanol (8mL), heated to 78°C and refluxed, After stirring for 4 hours, the solvent was evaporated under reduced pressure, and the residue was separated by column chromatography (silica gel, ethyl acetate / methanol, 30:1 v / v) to obtain a viscous liquid (0.34 g, 90%). All of it was dissolved in methanol (5 mL) and 20 mg of 10% palladium on carbon was added for catalytic reduction under hydrogen atmosphere. The reaction mixture was filtered with suction, and the filtrate was evaporated to remove the solvent under reduced pressure. The product was separated by column chromatography (silica gel, ethyl acetate / methanol, 20:1 v / v) to obtain viscous liquid P2 (0.32 g, 96%).

[0037] The produc...

Embodiment 3

[0041] When R 1 =COCH 3 , R 2 =CH 3 When, its molecular (P3) synthesis route and product structure are as follows:

[0042]

[0043] Synthesis steps and characterization: P2 (0.22g, 0.3mmol) and acetyl chloride (35mg, 0.45mmol) were mixed in dichloromethane (5mL), after stirring for 2 hours, the solvent was evaporated under reduced pressure and passed through column chromatography (silica gel, acetic acid Ethyl ester / methanol, 20:1 v / v) was isolated to give P3 (0.22 g, 95%) as a viscous liquid.

[0044] The product was subjected to NMR ( image 3 ) and mass spectrometric characterization: 1 H NMR (400MHz, CDCl 3 )δ10.47(s,1H),8.39(d,J=8.2Hz,1H),7.34(t,J=7.9Hz,1H),6.68(d,J=7.6Hz,1H),6.41(d, J=8.8Hz, 2H), 6.33(d, J=2.4Hz, 2H), 6.24(dd, J=8.9, 2.4Hz, 2H), 3.60–3.48(m, 16H), 3.47–3.42(m, 2H ), 3.35–3.25(m, 15H), 3.08(t, J=7.1Hz, 2H), 2.25(s, 3H), 1.13(t, J=7.0Hz, 13H). 13 CNMR (101MHz, CDCl 3 )δ169.06,168.82,153.52,152.97,148.66,136.57,133.85,128.43,117.79,117.38,115....

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Abstract

The invention provides an acid-resistant photo-controlled fluorescent molecular switch in an aqueous solution, and a synthesis method thereof. The specific molecular structure of the molecular switch adopts 3-amino or 3-acetylamino substituted rhodamine spiroamide as a basic structural unit, and the structural formula of the molecular switch is represented by formula (1). The 3-amino or 3-acetylamino substituted rhodamine spiroamide has acid resistance, and also retains a certain water solubility, so like acid-resistant dyes in water can be applied to fields of biological sensing detection and fluorescence imaging, and are not interfered by the pH value of a biological environment.

Description

technical field [0001] The invention belongs to the field of molecular switches, in particular to an acid-resistant light-controlled fluorescent molecular switch in aqueous solution and a synthesis method thereof. Background technique [0002] Rhodamine-based fluorescent dyes have excellent photophysical and photochemical properties such as high molar extinction coefficient, high fluorescence quantum yield, good photostability, long excitation wavelength and emission wavelength, and occupy an extremely important position in the field of organic dyes. It is especially widely used in the field of fluorescent probes. Among them, the "on-off" mechanism of rhodamine spiroamide is often used as a metal cation (M n+ ) fluorescent probe, which has no absorption and no fluorescence when it is closed, and after selectively recognizing specific metal cations, the helical ring of the probe is opened to generate absorption and strong fluorescence. [0003] Rhodamine spiroamides are cap...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/107C09K11/06C09B11/24G01N21/64
CPCC07D491/107C09B11/24C09K11/06C09K2211/1029C09K2211/1088G01N21/6428G01N21/643G01N21/6486
Inventor 徐兆超李锦祁清凯
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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