Liposomal glucose fluorescent probe with good biocompatibility and preparation method thereof

A biocompatible, fluorescent probe technology, applied in the field of fluorescence analysis and detection, can solve the problems of low sensitivity and selectivity, low water solubility, and long response time, and achieve high affinity and selectivity, low toxicity, and good solubility. Effect

Active Publication Date: 2022-07-15
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The purpose of the present invention is to provide a liposomal glucose fluorescent probe with good biocompatibility and fast response time for the existing organic boric acid molecular probes with low water solubility, long response time, low sensitivity and selectivity. and its preparation method

Method used

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  • Liposomal glucose fluorescent probe with good biocompatibility and preparation method thereof
  • Liposomal glucose fluorescent probe with good biocompatibility and preparation method thereof
  • Liposomal glucose fluorescent probe with good biocompatibility and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] The synthesis of molecular probe CN-DBA, its synthetic route is as follows:

[0046]

[0047] 1) Synthesis of compound C2:

[0048] Take a 500mL round-bottom flask, add 4-cyano-2-methylphenylboronic acid (5.00g, 31.06mmol), neopentyl glycol (3.88g, 37.25mmol) and 200mL toluene, add a Dean-Stark trap, Then the reaction was refluxed for 20 h, and the reaction was detected by TLC. After the reaction was completed, the reaction solvent was removed by drying under reduced pressure. The crude product was dissolved in dichloromethane and purified by flash column chromatography using dichloromethane as the eluent to obtain 6.76 g of oily compound C2 with a yield of 95.0%. 1 H NMR(400MHz, Chloroform-d)δ7.79(d,J=7.5Hz,1H),7.40(d,J=8.0Hz,2H),3.78(s,4H),2.52(s,3H),1.04 (s,6H).

[0049] 2) Synthesis of compound C3:

[0050] Take a 500mL round bottom flask, add compound C2 (6.76g, 29.51mmol), N-bromosuccinimide (5.52g, 30.99mmol), AIBN (0.13g, 0.79mmol) and carbon tetrachlorid...

Embodiment 2

[0058] The synthesis of molecular probe Ac-CDBA, its synthetic route is as follows:

[0059]

[0060] Synthesis steps:

[0061] 1) Synthesis of compound C7:

[0062] Take a 250mL round bottom flask, add aluminum chloride (2.61g, 19.57mmol), 9,10-dimethylanthracene (2.79g, 13.52mmol), anhydrous acetyl chloride (1.5mL, 21.1mmol) and 150mL carbon disulfide, room temperature Stir for 12h. Then the reaction system was heated to 45 °C for 2 h. The reaction was detected by TLC. After the reaction was completed, 45 mL of ice water containing 2.4 mL of hydrochloric acid was added, the reaction system was cooled to room temperature, the organic phase was extracted with dichloromethane, dried over anhydrous sodium sulfate, filtered, and the reaction solvent was removed under reduced pressure. Dichloromethane was used as the eluent for purification by flash column chromatography to obtain 1.59 g of compound C-8 with a yield of 47.3%. 1 H NMR (400MHz, Chloroform-d) δ 9.00 (d, J=1.5H...

Embodiment 3

[0070] The liposomal glucose fluorescent probe NPs- CN-DBA and NPs- Ac-CDBA The preparation method is as follows:

[0071] 1) Preparation of liposome fluorescent probe NPs by ultrasonic method- CN-DBA . First, CN-DBA (2.91 mg) prepared in Example 1 and DSPE-PEG were 2000 (14.55mg, DSPE-PEG 2000 and CN-DBA in a mass ratio of 5:1) dissolved in 1 mL of methanol. Under the ultrasonic condition of a cell sonicator (XL2000, Misonix Incorporated, NY), the above methanol mixed solution was injected into deionized water (15 mL) using a syringe (1 mL), and the mixed solution was continuously sonicated for 15 s. Then, the mixed solution was taken out and transferred to a regenerated cellulose dialysis bag with a molecular weight cut-off of 3500 (MW Cut-off: 3500) for dialysis for 24 hours. The dialyzed solution was concentrated to a certain volume using an ultrafiltration tube, and finally the liposome fluorescent probe NPs- CN-DBA .

[0072] 2) Preparation of liposome fluorescen...

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Abstract

The invention discloses a liposome glucose fluorescent probe with good biocompatibility and a preparation method thereof. The nanoliposome probe was developed by using an amphiphilic molecule (DSPE‑PEG 2000 ) encapsulating organoboronic acid glucose molecular probes together to form nanovesicles with lipid bilayer membranes. The diboronic acid recognition site in the organoboronic acid molecule can specifically bind to the cis-adjacent diol in the glucose molecule, so that the nanoprobe has high affinity and selectivity for glucose. The construction of liposome nanoprobes enables molecular probes to have the good properties of liposomes. Compared with organoboronic acid molecules, the liposome nanoprobe has better biocompatibility, faster response time and good fluorescence stability, thus enabling rapid and accurate identification and detection of glucose in vitro and in vivo. Meanwhile, the liposome nanoprobe has the advantages of simple preparation method, stability and high efficiency.

Description

technical field [0001] The invention belongs to the field of fluorescence analysis and detection, in particular to a liposome glucose fluorescent probe with good biocompatibility and a preparation method thereof. Background technique [0002] Glucose is an important chemical raw material for food and medicine, and at the same time, it is an important energy substance for sustaining life. Glucose is an important physiological signal substance, and its metabolic state is closely related to the development of various diseases, such as diabetes, tumor, obesity, Parkinson's and Alzheimer's disease. Therefore, the identification and detection of glucose has important application value in clinical medical research. [0003] Glucose detection methods mainly include enzyme-based sensors and organic boronic acid-based sensors. The enzyme-based glucose sensor is based on the specific reaction of the enzyme, which has the characteristics of strong specificity, but the recognition reac...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K49/00
CPCC09K11/06A61K49/0021A61K49/0054A61K49/0086G01N21/6428C09K2211/1007C09K2211/1011
Inventor 郗日沫王凯孟萌张瑞肖
Owner NANKAI UNIV
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