A kind of autofluorescence nanogel and its preparation method and application

A technology of nanogel and autofluorescence, which is applied in the application field of nanogel in the field of medicine, can solve the problems of denaturation, few therapeutic drugs targeted and efficient delivery, and lack of specificity, so as to achieve controllable preparation process, The effect of fast and efficient reaction conditions and good biocompatibility

Active Publication Date: 2019-02-26
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these chemical cross-linking reactions are usually not specific, which may cause the drug to participate in the cross-linking reaction, leading to denaturation
Moreover, although there have been many reports on the use of nanogels for drug delivery, few have been able to achieve targeted and efficient delivery of therapeutic drugs in vivo.

Method used

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  • A kind of autofluorescence nanogel and its preparation method and application
  • A kind of autofluorescence nanogel and its preparation method and application
  • A kind of autofluorescence nanogel and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Example 1 Synthesis of Hyaluronic Acid Lysine Tetrazole Derivatives (HA-Lys-Tet)

[0048] Under the condition of nitrogen protection, add tetrazole (608 mg), 10 mL of dimethyl sulfoxide, and DCC (120 mg) into a 50 mL two-necked bottle and stir for 24 hours. HA-Lys-NH 2 ( M n =35 K, 0.4 g) was dissolved in 30 mL formamide, added to the tetrazole solution after dissolving, stirred for 10 min, added DMAP (80 mg,), reacted for 48 hours, filtered, and the filtrate was mixed with water and dimethyl sulfoxide After dialysis, change to pure water dialysis, and freeze-dry to obtain the product HA-Lys-Tet (yield 69%); HA-Lys-Tet NMR characterization see figure 1 , 1 H NMR (D 2 O / DMSO-d 6 ): HA: δ 1.82, 2.70–3.68, and 4.23–4.38; Lys: δ 0.92,1.06, 1.52, 2.97, 3.61 and 3.95; Tet: δ 7.91,7.92 and 6.79, 6.80.

[0049] Four-arm polyethylene glycol tetrazole derivatives (PEG-Tet4) and chitosan tetrazole derivatives (Chit-Tet) can be prepared by replacing polymers. The structural f...

Embodiment 2

[0052] Example 2 Synthesis of Hyaluronic Acid Cystamine Methacrylate Derivatives (HA-Cy-MA)

[0053] HA-Cy-MA was synthesized in two steps, first the methacrylic acid derivative of cystamine (MA-Cy-NH 2 ) by Boc-Cy-NH 2 After reacting with methacryloyl chloride, it can be obtained by removing Boc protection, and then, under the condition of nitrogen protection, MA-Cy-NH 2 (14.5 mg, 66 μmol) was added to HA (50 mg, 1.43 μmol) activated by EDC (75.9 mg, 0.396 mmol) and NHS (22.8 mg, 0.198 mmol) in 5 mL of secondary water, placed in 40 °C oil In the bath, react in the dark for 24 hours, then dialyze with water, freeze-dry, and the yield is 92%; HA-Cy-MA nuclear magnetic characterization sees attached figure 2 , 1 H NMR (D 2 O): HA: δ 2.00,2.86–3.88, and 4.44–4.52; Cys: δ 2.70, 3.11–3.15 and 3.56; MA: δ 1.92, 5.45and 5.69.

Embodiment 3

[0054] Example Synthesis of Tricystine Methacrylamide Derivatives (MA-Cys-MA)

[0055] In an ice-water bath, a solution of cystine (1.2 g, 5.0 mmol) in NaOH (1.5 M, 10 mL) was added dropwise to methacryloyl chloride (2.0 mL, 20.6 mmol) in DCM (10 mL). The reaction was carried out in an ice-water bath for 4 h, and the pH was adjusted to 9.0 with NaOH solution during the reaction. After the reaction, the aqueous layer was separated with a separatory funnel, and about 3 mL of HCl (2M) was added dropwise to it, filtered, and vacuum-dried to obtain 1.72 g of white powder with a yield of 91%. MA-Cys-MA NMR characterization see attached image 3 , 1 H NMR (400 MHz, DMSO-d 6 ): MA (δ 5.72, 5.39 and 1.85), Cys (δ 12.92, 8.24, 4.53, 3.18 and 3.03).

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Abstract

The invention discloses an autofluorescent nano gel, a preparation method and application thereof. The present invention prepares nanogels by combining the reversed-phase nanoprecipitation method and the light-controlled "tetrazolene" click chemistry method. It has the advantages of catalyst and other advantages, which can effectively maintain the biological activity of entrapped drugs and proteins, and has a good application prospect in the fields of drug controlled release carriers. The cross-linking method of the nanogel disclosed in the present invention has strong selectivity, does not react with entrapped drugs, especially protein drugs and cells, can well maintain the efficacy of drugs, proteins and cells, and realizes complete and reliable Controlled release, so it can be used as an excellent sustained-release carrier for proteins and drugs; when it reaches the lesion, the nanogel releases the drug slowly to achieve effective therapeutic effects, without causing the problem of drug waste in the prior art.

Description

technical field [0001] The invention relates to a preparation method and application of a nanogel, in particular to a preparation method of a nanogel based on a polymer tetrazole derivative and a methacrylate group-containing crosslinking agent, and the application of the nanogel in medicine field applications. Background technique [0002] In the past few decades, protein drugs based on antibodies, cytokines, enzymes, and transcription factors have been widely used for the effective treatment of diseases such as diabetes, cardiovascular disease, and malignant tumors (Vermonden T, Censi R, HenninkWE. Chem. Rev . 2012, 112, 2853-2888; Walsh G. Nat. Biotech. 2000, 18, 831-833). Compared with chemotherapy drugs with higher toxic and side effects, protein drugs usually have higher specificity, better therapeutic effect and lower toxic and side effects, and have demonstrated superior disease treatment efficacy in clinical practice. But these clinically used protein drugs all wo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G81/00C08B37/08C08J3/075A61K9/06A61K47/36A61K47/42A61K47/34A61K49/00A61L27/52A61L27/58A61L27/20A61L27/24A61L27/18
CPCA61K9/06A61K47/22A61K47/34A61K47/36A61K47/42A61K49/0019A61K49/0073A61L27/18A61L27/20A61L27/24A61L27/52A61L27/58C08B37/0072C08G81/00C08J3/075C08J2387/00C08L5/08C08L5/02C08L67/04C08L69/00C08L71/02
Inventor 邓超陈景孟凤华钟志远
Owner SUZHOU UNIV
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