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A fluorescent modified cyclodextrin and its preparation method and application

A cyclodextrin and fluorescence technology, applied in the field of pharmacy, can solve the problems of inability to evaluate cell entry behavior and low sensitivity, and achieve the effects of improved sensitivity, high sensitivity and improved sensitivity

Active Publication Date: 2018-05-22
JINGCHU UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Aiming at the technical problems of the low sensitivity of the existing cyclodextrin content determination method and the inability to evaluate the cell-entry behavior, the present invention provides a method for modifying cyclodextrin by using a fluorescent probe——fluorescein isothiocyanate (FITC). The application of fluorescence spectrophotometry or high performance liquid chromatography-fluorescence detector analysis after fluorescence modification can significantly improve the sensitivity of cyclodextrin content determination, which is conducive to the study of drug loading effect and release behavior of dosage forms containing cyclodextrin. FITC modified cyclodextrin After refining, the cellular uptake behavior of cyclodextrin can also be easily studied by conventional instruments such as flow cytometer and laser confocal microscope, thus providing an evaluation method for the optimization of dosage forms containing cyclodextrin

Method used

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  • A fluorescent modified cyclodextrin and its preparation method and application
  • A fluorescent modified cyclodextrin and its preparation method and application
  • A fluorescent modified cyclodextrin and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1 Preparation and content determination of FITC-modified hydroxypropyl-β-cyclodextrin (FITC-HP-β-CD)

[0027] Accurately weigh 30 mg of FITC and dissolve it in 1 mL of DMSO, add it to 10 mL of 1% HP-β-CD solution, stir magnetically at 25°C for 24 hours, add 100 mL of absolute ethanol, remove the solvent by rotary evaporation, dilute to 10 mL with pure water, and transfer the solution into a 1500-2000Da dialysis bag, dialyze at 25°C for 72 hours (the dialysate is 1000ml of pure water, and the dialysate is replaced every 8 hours) to remove free FITC, and freeze-dry to obtain FITC-HP-β-CD. All operations require Avoid light. Measure with a fluorescence spectrophotometer, the measurement condition is an excitation wavelength of 495nm, an emission wavelength of 525nm, and the standard curve of FITC measured by fluorescence method is: Y=208.1X-6.7(R 2 =0.999) linear range: 0.11~2.60ng / mL, and the measured FITC content in the product is 0.96%.

Embodiment 2

[0028] Example 2 Preparation and content determination of FITC-modified β-cyclodextrin (FITC-β-CD)

[0029] Precisely weigh 100 mg of FITC and dissolve it in 1 mL of DMSO, add it to 10 mL of 1.5% β-CD solution, stir magnetically at 25°C for 36 hours, add 100 mL of absolute ethanol, remove the solvent by rotary evaporation, dilute to 10 mL with pure water, and transfer the solution Put it into a 1500-2000Da dialysis bag, dialyze at 25°C for 60 hours (the dialysate is 1000ml of pure water, and change the dialysate every 10 hours) to remove free FITC, freeze-dry to obtain FITC-β-CD, all operations need to be protected from light . Measured with a fluorescence spectrophotometer, the method is the same as in Example 1, and the FITC content in the product is 0.42%.

Embodiment 3

[0030] Example 3 Preparation and content determination of FITC-modified hydroxypropyl-γ-cyclodextrin (FITC-HP-γ-CD)

[0031] Accurately weigh 10 mg of FITC and dissolve it in 1 mL of DMSO, add it to 10 mL of 0.5% HP-γ-CD solution, stir magnetically at 25 °C for 12 hours, add 100 mL of absolute ethanol, remove the solvent by rotary evaporation, and dilute to 10 mL with pure water, and The solution was transferred to a 1500-2000Da dialysis bag, dialyzed at 25°C for 80 hours (the dialysate was 1000ml of pure water, and the dialysate was replaced every 8 hours) to remove free FITC, and freeze-dried to obtain FITC-HP-γ-CD. Operation needs to be protected from light. Measured with a fluorescence spectrophotometer, the method is the same as in Example 1, and the FITC content in the product is 0.63%.

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Abstract

Aiming at the technical problems that the cyclodextrin content determination method in the prior art has low sensitivity and cannot evaluate the cell-entry behavior, the present invention uses fluorescent probe fluorescein isothiocyanate (FITC) to modify cyclodextrin, FITC: cyclodextrin=0.1~ 20:1 (molecular ratio), preferably 0.5-10:1, most preferably 1:1; the cyclodextrin is preferably hydroxypropyl-β-cyclodextrin. Compared with the prior art, the FITC modified cyclodextrin provided by the present invention does not affect the effect of cyclodextrin inclusion drugs, and the content of cyclodextrin can be detected by FITC fluorescence spectrophotometry, and the lower limit of the detected cyclodextrin concentration is 27.5~110ng / mL, compared with the method for measuring cyclodextrins in the prior art with efficient liquid chromatography-differential refraction detector (concentration lower limit 0.1mg / mL), the sensitivity is significantly improved. Therefore, the present invention solves the technical problem of difficult quantification of cyclodextrin, and has extensive applications in the content determination of new dosage forms containing cyclodextrin, the investigation of pharmaceutical properties such as release, and the cell uptake behavior of cyclodextrin, targeted drug delivery effect, etc. Applications.

Description

technical field [0001] The invention belongs to the field of pharmacy, and in particular relates to a fluorescent modification method of cyclodextrin and its application. Background technique [0002] Cyclodextrin (cyclodextrin) is a cyclic oligosaccharide compound connected by 6 to 12 D-glucose molecules with 1,4-glycosidic bonds. It has a hollow cylindrical structure and is the most commonly used carrier material for the preparation of clathrates. . After drug molecules and cyclodextrin molecules form clathrates through van der Waals force, the solubility and stability of drugs can be improved, and liquid drugs such as volatile oils can be formulated into solid dosage forms, which can mask the bad smell or taste of drugs, adjust the release rate, and improve drug efficacy. Bioavailability, reducing the irritation and side effects of drugs, therefore, cyclodextrin materials have broad application prospects in the field of pharmacy. Commonly used cyclodextrin materials inc...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08B37/14C09K11/06A61K47/40
Inventor 杨希雄陈军顾薇王晶晶彭佩
Owner JINGCHU UNIV OF TECH
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