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A molecular shuttle-based diagnostic nanomedicine

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: 2022-07-08
FUDAN UNIV
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  • Summary
  • 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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  • A molecular shuttle-based diagnostic nanomedicine
  • A molecular shuttle-based diagnostic nanomedicine
  • A molecular shuttle-based diagnostic nanomedicine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0102]

[0103] 3-Chloropropylamine hydrochloride (1.00 g, 7.69 mmol) was dissolved in water (4 mL), sodium azide (1.49 g, 22.7 mmol) was added, heated to 80° C. and maintained for 15 hours. The temperature was lowered to room temperature, potassium hydroxide solid (1.10 g, 19.2 mmol) was added, and the mixture was extracted 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), triethylamine (166 μL, 120 mg, 1.2 mmol, 2.4 eq) dissolved in dry dichloromethane (5 mL) and benzoic acid were added Triazole-N,N,N',N'-tetramethylurea hexafluorophosphate (HBTU, 208 mg, 0.55 mmol, 1.1 eq) 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 without stirring 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): 5.6...

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 added dropwise over half an hour The above solution was stirred overnight at room temperature in the dark. The solvent was evaporated under reduced pressure, and 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)...

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Abstract

The invention belongs to the field of biotechnology, and relates to a novel medical nanomedicine based on a molecular shuttle. In the invention, the drug is connected to both ends of the molecule of the molecular shuttle through the click chemical reaction, and the size effect of the drug molecule is used to make the molecular shuttle difficult for the molecular shuttle to be recognized by the host of the molecular shuttle. The shuttle object can be quickly, accurately and specifically recognized and looped by the molecular shuttle host, forming a shuttle-shaped near-infrared supramolecular probe, which can be used to characterize the release behavior of drugs in real time at the cellular level in vitro or at the animal level in vivo.

Description

technical field [0001] The invention belongs to the field of biotechnology, relates to a drug delivery system with dual functions of targeting and diagnosis and treatment, in particular to a diagnosis and treatment nanomedicine based on a molecular shuttle. Background technique [0002] According to reports, small-molecule drugs are still the main weapons for humans to fight tumors. The prior art discloses that the efficacy of small-molecule drugs depends to a large extent 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 detect precisely. It is well known in the industry that, whether in clinical or academic research, instant access to drug release information from the prodrug system, including the amount, location and time of drug release, is very important in evaluating drug distribution, controlling drug dosage, and rationalizing drug...

Claims

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Application Information

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Patent Type & Authority Patents(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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