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Low-toxicity functionalized quantum dot modified by amination beta-cyclodextrin and preparation method thereof

A technology of cyclodextrin and quantum dots, 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: 2011-10-19
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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  • Low-toxicity functionalized quantum dot modified by amination beta-cyclodextrin and preparation method thereof
  • Low-toxicity functionalized quantum dot modified by amination beta-cyclodextrin and preparation method thereof
  • Low-toxicity functionalized quantum dot modified by amination beta-cyclodextrin and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] (1) Preparation of amino-β-cyclodextrin

[0036] 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 3.0g (44.1mmol) of ammonia water, and slowly dropwise add 10mmoL epichlorohydrin, raise the temperature to 60°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 amino-β-cyclodextrin.

[0037] (2) Preparation of folic acid-β-cyclodextrin by coupling amino-β-cyclodextrin with folic acid

[0038] In a dry and clean three-necked flask, add 5 mmol of ...

Embodiment 2

[0046] (1) Preparation of ethylenediamine-β-cyclodextrin

[0047] 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 7.0g (116.7mmol) of ethylenediamine, and slowly dropwise add 10mmol of epichlorohydrin, raise the temperature to 60°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 eluent and drying in vacuo to obtain ethylenediamine-β-cyclodextrin.

[0048] (2) Preparation of folic acid-β-cyclodextrin by coupling ethylenediamine-β-cyclodextrin with folic acid

[0049] In a dry ...

Embodiment 3

[0057] (1) Preparation of glycine-β-cyclodextrin

[0058] 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 8g (106.6mmol) glycine (2-aminoacetic acid), and slowly dropwise add 10mmol epichlorohydrin, raise the temperature to 60°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 obtain glycine-β-cyclodextrin.

[0059] (2) Preparation of folic acid-β-cyclodextrin by coupling glycine-β-cyclodextrin with folic acid

[0060] In a dry and clean three-nec...

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Abstract

The invention relates to a low-toxicity functionalized quantum dot modified by amination beta-cyclodextrin and a preparation method thereof, belonging to the field of a special molecular recognition and diagnosis reagent. The method comprises the following steps that functional-group amino is connected on beta-cyclodextrin by a chemical modification method to obtain amino-group-beta-cyclodextrin;under the action of 1-ethyl-3-(3-dimethyl propylamine) carbodiimide hydrochloride and N-hydroxysuccinimide, amino-group-beta-cyclodextrin is coupled with folic acid to obtain folic acid-beta-cyclodextrin; and by taking silver, zinc and other low-toxicity elements as raw materials, an oil-solubility near-infrared quantum dot is prepared, and folic acid-Beta-cyclodextrin is used to carry out water-solubility modification to the oil-solubility near-infrared quantum dot so as to obtain the low-toxicity functionalized quantum dot modified by amination beta-cyclodextrin. The quantum dot has good water-solubility and low-toxicity; and as emission spectrum is in a near-infrared area, and the folic acid is coupled, the quantum dot can be used for special fluorescence detection of tumors.

Description

technical field [0001] A low-toxicity functionalized quantum dot modified by an amination method β-cyclodextrin and a preparation method thereof. The prepared functionalized quantum dot can be used for specific fluorescence detection of tumor markers, etc., and belongs 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 ...

Claims

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Application Information

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IPC IPC(8): C09K11/62G01N21/64
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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