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Copper-doped polydopamine nano-drug with stable hydroxyethyl starch prodrug as well as preparation and application of copper-doped polydopamine nano-drug

A technology of polydopamine nanometer and hydroxyethyl starch, which is applied in the direction of nanomedicine, drug combination, nanotechnology, etc., can solve the problems of poor stability of PDA, limited tumor treatment effect, low light and heat absorption, etc., and achieve synergistic chemistry Kinetic therapy, improving PDA stability, enhancing the effect of photothermal effect

Active Publication Date: 2022-03-08
HUAZHONG UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Aiming at the defects of the prior art, the present invention provides a copper-doped polydopamine nano-medicine stable with hydroxyethyl starch prodrug, its preparation and application, the nano-medicine uses copper ion as a coordination center, and uses hydroxyethyl starch as a coordination center. The prodrug is used as a stabilizer, and dopamine is used as a polymerized monomer. It is prepared through a simple coordination polymerization strategy, which solves the technical problems of poor stability of PDA in the prior art, low light and heat absorption, and limited tumor therapeutic effect.

Method used

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  • Copper-doped polydopamine nano-drug with stable hydroxyethyl starch prodrug as well as preparation and application of copper-doped polydopamine nano-drug
  • Copper-doped polydopamine nano-drug with stable hydroxyethyl starch prodrug as well as preparation and application of copper-doped polydopamine nano-drug
  • Copper-doped polydopamine nano-drug with stable hydroxyethyl starch prodrug as well as preparation and application of copper-doped polydopamine nano-drug

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preparation example Construction

[0045] The hydroxyethyl starch prodrug used in the present invention is a reduction-responsive hydroxyethyl starch doxorubicin conjugate linked by a disulfide bond (abbreviated as HES-SS-DOX, further abbreviated as HSD). In some embodiments, the preparation method of HSD comprises the following steps:

[0046] (1) The hydroxyl group on hydroxyethyl starch and the carboxyl group on 3,3'-dithiodipropionic acid (DTDPA) undergo an esterification reaction in anhydrous dimethyl sulfoxide, and react at a temperature of 25-45°C The intermediate product was obtained in 24-72 hours. The molecular weight of the hydroxyethyl starch in the hydroxyethyl starch prodrug is 40-200kDa, preferably 130kDa.

[0047] (2) After the intermediate product in step (1) is separated and purified, the carboxyl group on the intermediate product and the amino group on the doxorubicin undergo further amide reaction in anhydrous dimethyl sulfoxide to obtain the reduction-responsive hydroxyethyl starch The dr...

Embodiment 1

[0062] A hydroxyethyl starch prodrug-stabilized copper-doped polydopamine nanoparticle, its preparation comprising the steps of:

[0063] (1) Weigh 3,3'-dithiodipropionic acid (DTDPA, 2.95g), dicyclohexylcarbodiimide (DCC, 579mg), 4-dimethylaminopyridine (DMAP, 171mg) in 100mL single port In the bottle, 20 mL of anhydrous dimethyl sulfoxide was added thereto, and stirred at room temperature for 2 hours to obtain carboxyl-activated 3,3'-dithiodipropionic acid. Then 5 g of dried hydroxyethyl starch (HES130 / 0.4, indicating that its average molecular weight is 130 kDa, and the molar substitution degree of hydroxyethyl group is 0.4) was weighed into the reaction system, and reacted at room temperature for 48 hours. After the reaction is completed, it is washed three times with a mixed solution of isopropanol / petroleum ether, and vacuum-dried to obtain the HES-DTDPA intermediate.

[0064] (2) Weigh HES-DTDPA (540 mg) and dissolve it in 20 mL of anhydrous dimethyl sulfoxide, add 1-(...

Embodiment 2

[0070]A hydroxyethyl starch prodrug-stabilized copper-doped polydopamine nanoparticle, its preparation comprising the steps of:

[0071] (1) Weigh 3,3'-dithiodipropionic acid (DTDPA, 295mg), dicyclohexylcarbodiimide (DCC, 57.9mg), 4-dimethylaminopyridine (DMAP, 17.1mg) in 25mL 5 mL of anhydrous dimethyl sulfoxide was added to the single-necked bottle, and stirred at room temperature for 2 hours to obtain carboxyl-activated 3,3'-dithiodipropionic acid. Then weighed dry hydroxyethyl starch 0.5 (HES40 / 0.5, indicating that its average molecular weight is 40kDa, and the molar substitution degree of hydroxyethyl is 0.5) was added into the reaction system, and reacted at room temperature for 72h. After the reaction is completed, it is washed three times with a mixed solution of isopropanol / petroleum ether, and vacuum-dried to obtain the HES-DTDPA intermediate.

[0072] (2) Weigh HES-DTDPA (108 mg) and dissolve it in 10 mL of anhydrous dimethyl sulfoxide, add 1-(3-dimethylaminopropyl...

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Abstract

The invention belongs to the technical field of multidisciplinary crossing of chemistry, materials, biomedicine and the like, and particularly relates to a copper-doped polydopamine nano-drug with stable hydroxyethyl starch prodrug as well as preparation and application of the copper-doped polydopamine nano-drug. The nano-drug is prepared by taking dopamine and copper ions as precursor components and reducing responsive hydroxyethyl starch adriamycin prodrug as a stabilizer through a simple'one-pot 'coordination polymerization strategy. Structural characterization shows that the nano-drug shows uniform particle size distribution and excellent stability. Functional tests show that the nano-drug not only shows excellent photo-thermal performance, but also can realize specific generation of chemotherapeutic drug adriamycin (reducing conditions) and high-toxicity hydroxyl free radicals (high-content H2O2) in a tumor microenvironment. Through the synergistic effect of multi-aspect treatment, the tumor growth is effectively inhibited.

Description

technical field [0001] The invention belongs to the interdisciplinary technical fields of chemistry, materials, biomedicine, etc., and more specifically relates to a copper-doped polydopamine nanomedicine stabilized by hydroxyethyl starch prodrug, its preparation and application. Background technique [0002] As a non-invasive cancer treatment modality, photothermal therapy (PTT) has attracted extensive attention of scientists in recent decades. The technology utilizes the photothermal conversion ability of photothermal agents (PTAs) to harvest energy from excitation light and convert the energy into heat energy, raising the temperature of the surrounding environment and triggering the death of cancer cells. Usually, photothermal therapy uses near-infrared light (NIR) with strong tissue penetrating power as the excitation light source, which ensures the safety of the therapy. [0003] Among numerous photothermal agents (eg, gold nanorods, carbon nanotubes, copper sulfide, e...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K41/00A61K31/704A61K47/61A61K47/52A61P35/00B82Y5/00B82Y40/00
CPCA61K41/0052A61K31/704A61K47/61A61K47/52A61P35/00B82Y5/00B82Y40/00A61K2300/00Y02A50/30
Inventor 李子福杨祥良熊雨轩
Owner HUAZHONG UNIV OF SCI & TECH
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