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Targeted water-soluble near-infrared dye and preparation method thereof

A near-infrared dye, water-soluble technology, used in pharmaceutical formulations, photodynamic therapy, medical preparations with inactive ingredients, etc., can solve problems such as poor water solubility and lack of targeting

Inactive Publication Date: 2020-03-17
QINGDAO UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this efficient near-infrared dye CyI has the disadvantages of poor water solubility and lack of targeting

Method used

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  • Targeted water-soluble near-infrared dye and preparation method thereof
  • Targeted water-soluble near-infrared dye and preparation method thereof
  • Targeted water-soluble near-infrared dye and preparation method thereof

Examples

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preparation example Construction

[0036] The invention provides a method for preparing a targeted water-soluble near-infrared dye, comprising the following steps:

[0037] (1) The solution of CyI is mixed with 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDC) and N-hydroxysuccinimide (NHS), and the activation reaction is obtained A solution of activating CyI; the CyI is an iodinated derivative of the cyanine dye Cy7;

[0038] (2) The solution of activated CyI obtained in the step (1) is added dropwise to NH 2 -PEG-NH 2 In the aqueous solution, carry out amide reaction to obtain PEGylated CyI;

[0039] (3) Mix an aqueous solution of hyaluronic acid (HA) with 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDC) and N-hydroxysuccinimide (NHS) , performing an activation reaction to obtain an aqueous solution of activated hyaluronic acid;

[0040] (4) The aqueous solution of activated hyaluronic acid obtained in the step (3) is mixed with the PEGylated CyI obtained in the step (2), and ...

Embodiment 1

[0069] (1) Accurately weigh 5 mg of CyI powder, and add 1 mL of DMF (N,N dimethylformamide) to dissolve it.

[0070] (2) Take 1.85 mg of EDC (1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride) and 1.11 mg of N-hydroxysuccinimide (NHS) into the dissolved CyI The carboxyl group of CyI was activated by stirring in a DMF (N,N dimethylformamide) solution for 4h.

[0071] (3) Accurately weigh NH 2 -PEG-NH 2 (Molecular weight 2000) 25.7mg (CyI: NH 2 -PEG-NH 2 =1:2) was dissolved in 2 mL of pure water, and the CyI solution activated in (1) was slowly dropped into it while stirring continuously, and stirred overnight at room temperature (18h).

[0072] (4) The solution obtained from the reaction was dialyzed for 2 days with a dialysis bag with a molecular weight cut off of 2000 to remove compounds other than PEGylated CyI.

[0073] (5) Accurately weigh 19 mg of HA (molecular weight 3000), (CyI: HA=1:1 or 2:1) add 0.5 mL of pure water to dissolve, then add EDC 1.85 mg, NHS...

Embodiment 2

[0076](1) Accurately weigh 10 mg of CyI powder, and add 2 mL of DMF (N,N dimethylformamide) to dissolve it.

[0077] (2) Add 4.9 mg of EDC (1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride) and 2.96 mg of N-hydroxysuccinimide (NHS) to the dissolved CyI The carboxyl group of CyI was activated by stirring in a DMF (N,N dimethylformamide) solution for 4h.

[0078] (3) Accurately weigh NH 2 -PEG-NH 2 (Molecular weight 2000) 51.5mg (CyI: NH 2 -PEG-NH 2 =1:2) was dissolved in 2 mL of pure water, and the CyI solution activated in (1) was slowly dropped into it while stirring constantly, and stirred and reacted at room temperature for 24 hours.

[0079] (4) The solution obtained from the reaction was dialyzed for 2 days with a dialysis bag with a molecular weight cut off of 2000. (Compounds other than PEGylated CyI)

[0080] (5) Accurately weigh 19 mg of HA (molecular weight 3000), add (CyI:HA=1:1 or 2:1) into 0.5 mL of pure water to dissolve, then add EDC 2.47 mg, NHS...

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Abstract

The invention provides targeted water-soluble near-infrared dye and a preparation method thereof. The preparation method comprises the following steps: carrying out an activation reaction on a CyI solution, EDC and NHS, then dropwise adding the obtained product into an NH2-PEG-NH2 aqueous solution, and carrying out an amidation reaction to obtain PEG-processed CyI; carrying out an activation reaction on the aqueous solution of HA, EDC and NHS to obtain an aqueous solution of activated hyaluronic acid; mixing the aqueous solution of the activated hyaluronic acid with the PEG-processed CyI, andcarrying out amidation reaction to obtain targeted water-soluble near-infrared dye. According to the invention, the CyI is combined with PEG, so that the water solubility of CyI is improved and the self-aggregation of CyI in an aqueous solution is reduced; and the HA is connected to serve as a target head and CD44 receptors highly expressed on the surface of a tumor are specifically recognized, and nanometer particles can be delivered into tumor cells in a targeted mode through receptor-mediated endocytosis in the obtained targeted water-soluble near-infrared dye.

Description

technical field [0001] The invention relates to the technical field of nanocarriers, in particular to a targeting water-soluble near-infrared dye and a preparation method thereof. Background technique [0002] Optical therapy plays an important role in tumor treatment. It has high selectivity, low toxicity and side effects, and remote controllability. These advantages make it attract widespread attention in cancer treatment. Photothermal therapy (PTT) and photodynamic therapy (PDT) are two different phototherapies most widely used in tumor treatment. Photothermal therapy (PTT) is the use of photothermal agents to absorb light of specific wavelengths, and then convert it into heat to cause local environmental temperature rise and irreversible damage, inducing apoptosis or necrosis of cancer cells; photodynamic therapy (PDT) is a photosensitizer Absorbs light of a specific wavelength, transitions from the ground state to the excited state, and the photosensitizer in the excit...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K41/00A61K47/60A61K47/61A61P35/00
CPCA61K41/0057A61K47/60A61K47/61A61P35/00
Inventor 曹洁孙勇曹伟迟金男
Owner QINGDAO UNIV