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Novel diagnosis and treatment type nano-drug based on molecular shuttle

A nano-drug and molecular shuttle technology, applied in the biological field, can solve demanding problems and achieve the effect of improving curative effect and reducing systemic toxicity

Active Publication Date: 2020-04-17
FUDAN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The application of the above-mentioned technologies has solved the dilemma of "Schrödinger's cat" to a large extent. However, there are some defects in the application of the above-mentioned technologies. For example, the aggregation-induced luminescence technology needs to be explored. When the needle reaches a certain concentration in the body, it can form aggregates and emit fluorescence; the fluorescence energy resonance transfer technology requires the drug itself to have a certain special structure, which can be used as a fluorescence quencher for the probe molecule, so that the probe can recover after the drug is released. Luminous state; Positron emission tomography technology requires more stringent requirements, and needs to use nanoparticles that can be developed under PET / CT as the building block (such as nano gold, etc.), etc.

Method used

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  • Novel diagnosis and treatment type nano-drug based on molecular shuttle
  • Novel diagnosis and treatment type nano-drug based on molecular shuttle
  • Novel diagnosis and treatment type nano-drug based on molecular shuttle

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0102]

[0103] 3-Chloropropylamine hydrochloride (1.00g, 7.69mmol) was dissolved in water (4mL), sodium azide (1.49g, 22.7mmol) was added, heated to 80°C and kept for 15 hours. Cool down to room temperature, add solid potassium hydroxide (1.10 g, 19.2 mmol), and extract with ether (5 mL×3). The organic phases were combined, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain compound 2 as a colorless oily liquid (0.77 g, 100%).

[0104] Rf=0.4(dichloromethane:methanol=30:1, v:v).

[0105] 1 H NMR (400MHz, CDCl 3 ,δ,ppm):3.38(t,J=3.6Hz,2H,H-5,6),2.81(t,J=6.8Hz,2H,H-1,2),1.74(q,J=6.8Hz ,2H,H-3,4),1.75-1.00(s,w,2H,H-7,8).

[0106] FT-IR(v cm-1 ):2099.6 (vs, v N3 ),1599.6(s,δ NH2 ),1304.4(s,v C-N )...

Embodiment 2

[0108]

[0109] Oleic acid (140 mg, 0.5 mmol, 1 eq) was dissolved in dry dichloromethane (5 mL), and triethylamine (166 μL, 120 mg, 1.2 mmol, 2.4 eq) and benzo Triazole-N,N,N',N'-tetramethyluronium hexafluorophosphate (HBTU, 208mg, 0.55mmol, 1.1eq), and stirred at room temperature for half an hour. Compound 2 (250 mg, 2.5 mmol, 5 eq) was dissolved in dry dichloromethane (5 mL), and slowly added dropwise to the above solution and stirred at room temperature for four hours. The solvent was evaporated under reduced pressure, water (10 mL) was added and the pH was adjusted to 2. The above aqueous solution was extracted with petroleum ether (5 mL×3), the organic phases were combined, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain compound 3 as a wax (144 g, 79%).

[0110] Rf=0.8 (dichloromethane:ethyl acetate=30:1, v:v).

[0111] 1 H NMR (400MHz, CDCl 3 ,δ,ppm):5.60(s,w,1H,H-34),5.34(s,2H,H-18,19),3.35(t,J=6.8Hz,4H,H-35,3...

Embodiment 3

[0114]

[0115] Cystamine dihydrochloride (4,225 mg, 1 mmol, 1 eq) and triethylamine (220 mg, 2 mmol, 2 eq) were dissolved in dry tetrahydrofuran (5 mL) and stirred at room temperature for ten minutes. Oleic acid (282mg, 1mmol, 1eq), triethylamine (122mg, 1.2mmol, 1.2eq) and HBTU (400mg, 1.1eq, 1.1mmol) were dissolved in dry tetrahydrofuran (10mL) and slowly dropped into The above solution was stirred overnight at room temperature in the dark. The solvent was distilled off under reduced pressure, a saturated solution of ammonium chloride (10 mL) was added and extracted with ethyl acetate (10 mL×3). The organic phases were combined, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain compound 5 as a yellow wax (144 g, 79%).

[0116] Rf=0.7 (dichloromethane:methanol=30:1, v:v).

[0117] 1 H NMR (400MHz, CDCl 3 ,δ,ppm):6.30(s,w,1H,H-34),5.30(s,2H,H-18,19),3.59-3.53(m,2H,H-35,36),2.81-2.73 (m,6H,H37~42),2.41-2.24(m,2H,H-43,4...

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Abstract

The invention belongs to the technical field of biology, and relates to a novel diagnosis and treatment type nano-drug based on a molecular shuttle. According to the invention, a drug is linked to twoends of a molecular shuttle guest molecule through a click chemical reaction; by utilizing a drug molecule size effect, the molecular shuttle guest is difficultly be identified and penetrated by a molecular shuttle host; and in a tumor reducing microenvironment, the drug is released while the molecular shuttle guest is liberated, so that the molecular shuttle guest can be quickly, precisely and specifically recognized and penetrated by the molecular shuttle host to form a fusiform near-infrared supramolecular probe, wherein the fusiform near-infrared supramolecular probe can be used for real-timely characterizing the release behavior of the drug at an in-vitro cell level or an in-vivo animal level.

Description

technical field [0001] The invention belongs to the field of biotechnology, and relates to a drug delivery system with dual functions of targeting and diagnosis and treatment, in particular to a molecular shuttle-based diagnosis and treatment nano-medicine. Background technique [0002] According to reports, small-molecule drugs are still the main weapon for human to fight against tumors. The prior art discloses that the curative effect of small-molecule drugs depends largely on the concentration of the drug in the lesion. Studies have shown that once the drug enters the body, it is vividly called a "Schrödinger's cat". Distribution information is difficult to ascertain precisely. It is well known in the industry that whether in clinical or academic research, it is very important in the fields of evaluating drug distribution, controlling drug dosage, and rationalizing drug use to obtain information about drug release from the prodrug system immediately, including the amount...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K9/107A61K31/555A61K47/22A61K47/54A61K47/62A61K49/00A61P35/00
CPCA61K9/1075A61K31/555A61K47/62A61K47/542A61K47/22A61P35/00A61K49/0082A61K49/0019
Inventor 孙涛蒋晨
Owner FUDAN UNIV
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