Carboxylation beta-cyclodextrin modified low-toxicity functional quantum dot and preparation method thereof

A cyclodextrin and quantum dot technology, which is applied in the field of specific molecular recognition diagnostic reagents, can solve the problems of cytotoxicity and toxicity, and achieve the effect of low toxicity and good water solubility.

Inactive Publication Date: 2011-10-05
江苏迈健生物科技发展股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But their potential toxicity lies in their coatings. If these coatings break away from the core, no matter whether the core of the combination (CdTe, CdSe) or a single metal cadmium (Cd) is released, toxicity will occur.
Alternatively, some quantum dot coating materials are inherently cytotoxic, such as methanol acetate (MAA)

Method used

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  • Carboxylation beta-cyclodextrin modified low-toxicity functional quantum dot and preparation method thereof
  • Carboxylation beta-cyclodextrin modified low-toxicity functional quantum dot and preparation method thereof
  • Carboxylation beta-cyclodextrin modified low-toxicity functional quantum dot and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] (1) Preparation of carboxymethyl-β-cyclodextrin

[0039] Add 5 mmol of β-cyclodextrin into a 250 mL three-neck round bottom flask, add 60 mL of deionized water, and add 9 mmol of KOH under magnetic stirring to completely dissolve the β-cyclodextrin. Gradually raise the temperature to 50°C, add 10 mmol 2-chloroacetate sodium, raise the temperature to 90°C under continuous stirring and keep it for 1 hour, then stop heating. After the reaction system is cooled to room temperature, adjust the pH of the reaction system to 5-6 with dilute sulfuric acid, add 150mL of absolute ethanol, perform purification chromatography on a neutral alumina column, use 60% ethanol as the eluent, and collect the eluate , concentrating the eluate and drying in vacuo to give carboxymethyl-β-cyclodextrin.

[0040] (2) Coupling of carboxymethyl-β-cyclodextrin and folic acid to prepare folic acid-β-cyclodextrin

[0041] a. Activation of folic acid: Add 5 mmol of folic acid to a dry and clean three...

Embodiment 2

[0052] (1) Preparation of carboxyethyl-β-cyclodextrin

[0053] Add 5 mmol of β-cyclodextrin into a 250 mL three-neck round bottom flask, add 60 mL of deionized water, and add 9 mmol of KOH under magnetic stirring to completely dissolve the β-cyclodextrin. Gradually raise the temperature to 50°C, add 10mmol sodium 3-chloropropionate, raise the temperature to 90°C under continuous stirring and keep it for 1 hour, then stop heating. After the reaction system is cooled to room temperature, adjust the pH of the reaction system to 5-6 with dilute sulfuric acid, add 150mL of absolute ethanol, perform purification chromatography on a neutral alumina column, use 60% ethanol as the eluent, and collect the eluate , concentrated eluate and vacuum dried to obtain carboxyethyl-β-cyclodextrin.

[0054] (2) Coupling of carboxyethyl-β-cyclodextrin and folic acid to prepare folic acid-β-cyclodextrin

[0055] a. Activation of folic acid: Add 5 mmol of folic acid to a dry and clean three-necked...

Embodiment 3

[0066] Quantum Yield Test of Folic Acid-β-Cyclodextrin Modified Quantum Dots

[0067] The fluorescence quantum yield of folic acid-β-cyclodextrin modified quantum dots was measured at room temperature, and the aqueous solution of rhodamine B (fluorescence quantum yield of 0.98) was used as a reference solution, and the rhodamine B and folic acid were measured respectively. The integrated fluorescence intensity of the linked β-cyclodextrin modified quantum dots under the same wavelength excitation and the absorbance value at this wavelength are substituted into the following formula to calculate the quantum yield:

[0068]

[0069] (Φ-quantum yield of the substance to be tested; Φ F,cal -quantum yield of reference substance; S-integrated area of ​​fluorescence emission spectrum; A-absorbance of solution at selected wavelength; n-refractive index of solution; λex-excitation wavelength of substance to be measured; S cal - the integrated area of ​​the fluorescence emission spe...

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Abstract

The invention relates to a carboxylation beta-cyclodextrin modified low-toxicity functional quantum dot and a preparation method thereof, belonging to the field of specific molecular recognition diagnostic reagent. In the invention, the preparation method of the carboxylation beta-cyclodextrin modified low-toxicity functional quantum dot comprises the steps that: a functional group carboxyl is connected on beta-cyclodextrin through a chemical modification method to obtain carboxy-beta-cyclodextrin; under the action of 1-ethyl-3-(3-dimethyl propylamine) carbodiimide hydrochloride and N-hydroxysuccinimide, activated folic acid is firstly coupled with amino-terminated poly (ethylene glycol) and then coupled with the carboxy-beta-cyclodextrin to obtain folic acid-beta-cyclodextrin; silver, zinc and other low-toxicity elements are utilized as raw materials to prepare an oil soluble infrared quantum dot, and the folic acid-beta-cyclodextrin is utilized to perform water-soluble modification on the oil soluble infrared quantum dot to obtain the carboxylation beta-cyclodextrin modified low-toxicity functional quantum dot. The quantum dot prepared by the method disclosed by the invention has good water solubility and low toxicity, and the emission spectrum is in a near infrared area, and the quantum dot can be used for specific fluorescence detection on tumors because of being coupled with the folic acid.

Description

technical field [0001] A low-toxicity functionalized quantum dot modified by carboxylation method β-cyclodextrin and its preparation method, the prepared functionalized quantum dot can be used for specific fluorescence detection of tumor markers, etc., belonging to the field of specific molecular recognition diagnostic reagents . Background technique [0002] Folic acid is an essential vitamin for cells (especially cells with vigorous proliferation), and it participates in the one-carbon transfer reaction of various metabolic pathways. Cellular transport of folate is accomplished by two transmembrane proteins, the low-affinity reduced folate carrier and the high-affinity folate receptor. It has been confirmed that folate receptors are overexpressed on the surface of a variety of tumor cells, such as ovarian cancer, cervical cancer, endometrial cancer, breast cancer, lung cancer, brain tumor, ependymal cell tumor, etc., while the expression in most normal tissues It is limi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/62C08G81/00C08G65/48C08B37/16G01N21/64
Inventor 邵建辉
Owner 江苏迈健生物科技发展股份有限公司
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