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Tumor cell nuclear targeted drug-loading nanoparticle comprising functional polypeptide modified heptamethine cyanine dye and preparation method thereof

A technology of Qijiachuan cyanine and functional polypeptide, which is applied in the field of medicine to achieve the effects of improving poor water solubility, simple preparation method, and improving photothermal performance

Active Publication Date: 2019-11-15
TIANJIN MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, direct modification of IR780 by peptides has not been reported yet

Method used

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  • Tumor cell nuclear targeted drug-loading nanoparticle comprising functional polypeptide modified heptamethine cyanine dye and preparation method thereof
  • Tumor cell nuclear targeted drug-loading nanoparticle comprising functional polypeptide modified heptamethine cyanine dye and preparation method thereof
  • Tumor cell nuclear targeted drug-loading nanoparticle comprising functional polypeptide modified heptamethine cyanine dye and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0069] 1. Synthesis and characterization of TAT-IR780

[0070] Dissolve TAT (120mg, 72μmol), IR780 (40mg, 60μmol) and triethylamine (15μL, 108μmol) in 12mL of dimethyl sulfoxide (DMSO), and let the reaction system flow with nitrogen gas, and stir the reaction at 40°C for 72h in the dark. , and then transfer the reaction solution to a dialysis bag (molecular weight cut-off of 500Da), and dialyze in ultrapure water for 24 hours, change the outer dialysate every 6 hours, remove unreacted TAT polypeptide, and obtain dark green powdery diisocyanate after freeze-drying. Joint product TAT-IR780. Synthetic route such as figure 1 Shown, the chemical structure of TAT-IR780 passes IR spectrum ( figure 2 ), 1 H NMR spectrum ( image 3 ) and mass spectrometry ( Figure 4 ) to characterize. The final synthesized TAT-IR780 obtained in the IR spectrum and 1 The H NMR spectrum has the characteristic peaks of IR780 and TAT at the same time. According to the molecular ion peak of the mas...

Embodiment 2

[0102] 1. Synthesis of penetrating peptide R9 coupled to IR780

[0103] R9 (sequence RRRRRRRRRC) polypeptide (110mg, 72μmol), IR780 (40mg, 60μmol) and triethylamine (15μL, 108μmol) were dissolved in 12mL dimethyl sulfoxide (DMSO), and the reaction system was ventilated with nitrogen gas flow, under dark conditions Stir and react at 40°C for 72 hours, then transfer the reaction liquid to a dialysis bag (molecular weight cut-off: 500 Da), and dialyze in ultrapure water for 24 hours, replace the outer dialysate every 6 hours, remove unreacted R9 polypeptide, and freeze-dry to obtain Dark green powder conjugate R9-IR780.

[0104] 2. Preparation and characterization of drug-loaded nanoparticle RID of R9-IR780 efficiently loaded with anthracycline chemotherapy drug DOX

[0105] Dissolve the anthracycline chemotherapy drug doxorubicin hydrochloride (DOX HCl) in methanol, add TEA according to 3 equivalents and stir for 8 hours, carry out desalination treatment, then rotary evaporate ...

Embodiment 3

[0107] 1. Synthesis of TAT-IR780

[0108] Dissolve TAT (120mg, 72μmol), IR780 (40mg, 60μmol) and triethylamine (15μL, 108μmol) in 12mL of dimethyl sulfoxide (DMSO), and let the reaction system flow with nitrogen gas, and stir the reaction at 40°C for 72h in the dark. , and then transfer the reaction solution to a dialysis bag (molecular weight cut-off of 500Da), and dialyze in ultrapure water for 24 hours, change the outer dialysate every 6 hours, remove unreacted TAT polypeptide, and obtain dark green powdery diisocyanate after freeze-drying. Joint product TAT-IR780.

[0109] 2. Preparation of drug-loaded nanoparticle TIE of TAT-IR780 efficiently loading anthracycline chemotherapy drug epirubicin (EPB)

[0110] Dissolve the anthracycline chemotherapeutic drug epirubicin hydrochloride (EPB·HCl) in methanol, add TEA according to 3 equivalents and stir for 8 hours, carry out desalination treatment, then remove the methanol by rotary evaporation, and then redissolve in DMSO, the...

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Abstract

The invention provides a tumor cell nuclear targeted drug-loading nanoparticle comprising a functional polypeptide modified heptamethine cyanine dye and a preparation method and application thereof. Amethod for directly modifying a functional polypeptide of the heptamethine anthocyanin dye is adopted, the water solubility and optical stability of the heptamethine cyanine dye are improved, and theheptamethine cyanine dye is co-loaded with an anthracene ring chemotherapy drug to obtain the drug-loading nanoparticle having a tumor cell nuclear targeting function. The direct modification of thefunctional peptide of the heptamethine anthocyanin dye is realized, the problem of poor water solubility of the heptamethine cyanine dye is effectively solved, the drug-loading nanoparticle prepared by co-loading the anthracene ring chemotherapy drug enhances the uptake of the drug-loading nanoparticle by tumor cells, the aggregation and distribution of tumor cell nuclei in a nuclear-approaching area are realized, targeting of the tumor cell nuclei is realized, and the uptake of a photosensitizer by the tumor cells is improved.

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to a tumor cell nucleus-targeted drug-loaded nanoparticle containing functional polypeptide-modified heptamethine dyes and a preparation method thereof. Background technique [0002] Breast cancer is one of the malignant tumors that seriously threaten women's life and health. According to the latest statistics, the incidence and mortality of breast cancer worldwide are 29% and 15%, respectively. In China, the incidence of breast cancer has shown a significant upward trend in recent years, ranking first among female cancers. The clinical treatment of breast cancer includes surgery, radiotherapy, chemotherapy and immunotherapy, etc., but these methods have their own limitations. For example, chemotherapeutics can easily lead to multidrug resistance in breast cancer cells, reducing the efficacy of drugs, and most chemotherapeutic drugs lack selectivity and have non-negli...

Claims

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Application Information

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IPC IPC(8): A61K49/00A61K47/69A61K47/64A61K41/00A61K31/704A61P35/00
CPCA61K49/0032A61K49/0056A61K41/0052A61K31/704A61P35/00A61K47/6929A61K47/64A61K41/0057A61K2300/00
Inventor 王银松万国运程园园宋佳刘媛媛张思培陈倩周策
Owner TIANJIN MEDICAL UNIV
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