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Shape-variable polypeptide-dye conjugate as well as preparation method and application thereof

A conjugate and dye technology, applied in the field of biomedicine, can solve the problems of low photothermal conversion efficiency and poor photothermal dye stability, and achieve the effects of improving delivery efficiency, enhancing residence time, and improving photothermal performance.

Active Publication Date: 2021-06-22
SOUTHWEST JIAOTONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In view of the technical problems of low stability of photothermal dyes and low photothermal conversion efficiency in the prior art, the present invention provides a polypeptide-crotonate cyanine dye conjugate with variable morphology, its preparation method and application, The self-assembly of polypeptide-crotonate cyanine dye conjugates under polar conditions forms structurally stable nanoparticles, and the morphology of nanofibers is transformed under the specific action of the morphology transformation driving unit, and the self-assembled nanoparticle Morphology transformation effectively improves the photothermal conversion performance of crotonate cyanine dyes

Method used

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  • Shape-variable polypeptide-dye conjugate as well as preparation method and application thereof
  • Shape-variable polypeptide-dye conjugate as well as preparation method and application thereof
  • Shape-variable polypeptide-dye conjugate as well as preparation method and application thereof

Examples

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Embodiment 1

[0039] This embodiment provides a polypeptide-dye conjugate with variable morphology, which is marked with CR-KLA. The substance and the spacer molecule Ahx used to connect the two fragments form an amphiphilic photothermal dye conjugate, wherein the hydrophobic crotonate cyanine dye derivatives include croconate cyanine dye CR and a compound linked to it through an amide reaction KLVFFGFLG sequence, under the specific recognition of the biological enzyme Cathepsin B overexpressed in tumor cells, the KLVFFGFLG sequence can be cut into two parts from the phenylalanine F and leucine L sites, making the amphipathic The hydrophilic segment and the hydrophobic segment of the photothermal dye conjugate are separated for structural reorganization, resulting in a change in shape.

[0040] Specifically, the polypeptide-dye conjugate CR-KLA has a linear structure, as shown in Formula 1:

[0041]

[0042] Formula 1

[0043] The full material sequence of CR-KLA is CR-KLVFFGFLG-Ahx-KL...

Embodiment 2

[0049] This example provides a method for preparing a polypeptide-dye conjugate CR-KLA with variable morphology. The specific process is shown in the attached description. figure 1 As shown, the specific preparation process is as follows:

[0050] S1. Synthesizing the KLVFFGFLG-Ahx-KLCKLAKKLCKLAK sequence based on the Fmoc solid-phase synthesis method;

[0051] First weigh 300mg of Rink resin, swell with N,N-dimethylformamide DMF for 30min, configure deprotection solution (70% morpholine, 30% DMF) and add it to Rink resin to remove Fmoc protection on the resin group, to expose the N-terminal amino group, and then use DMF and DCM to wash three times respectively. Weigh the required amino acid and HATU, dissolve them in DMF, add DIPEA to adjust the base, and add them to the resin for reaction. Each amino acid is reacted twice, each time for 2 hours.

[0052] S2. Weigh 1.5 equivalents of crotonate cyanine dye and 0-(7-azabenzotriazole)-N,N,N',N'-tetramethyluronium hexafluoropho...

Embodiment 3

[0058] In order to verify the photothermal performance of CR-KLA under two different nano-self-assembled morphologies, the prepared CR-KLA nanoparticle and nanofiber materials were exposed to 808nm near-infrared light at 1w / cm 2 The power was irradiated for 10 minutes respectively, and the temperature value was recorded every 30s to obtain the following Figure 5 The temperature rise curve is shown. The inventors creatively found that after irradiating for 10 minutes, the ΔT of the CR-KLA nanoparticle morphology group was stable at 15.5°C, and the CR-KLA nanofiber morphology group ΔT was stable at 23.5°C, while the PBS group showed no heating ability. The temperature change value ΔT of the nanofibers formed by the cketone cyanine polypeptide material is 8 °C higher than that of the nanoparticles formed by it under the same light time and light intensity, which proves that the light intensity of the cketone cyanine dye after the morphology transformation The thermal performanc...

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Abstract

The invention discloses a shape-variable polypeptide-croconic acid cyanine dye conjugate as well as a preparation method and the application thereof. The polypeptide-dye conjugate comprises a hydrophilic functional peptide fragment, a hydrophobic croconic acid cyanine dye fragment and a spacer molecule Ahx for connecting the hydrophilic functional peptide fragment and the hydrophobic dye fragment, the hydrophobic dye segment comprises a morphology adaptation unit capable of realizing morphology transformation, and the polypeptide-dye conjugate can generate morphology transformation through specific recognition or action of a morphology transformation driving unit and the morphology adaptation unit; a polypeptide-croconic acid cyanine dye conjugate is self-assembled under a polar condition to form nanoparticles with a stable structure, the nanoparticles are transformed into nanofiber morphology under the specific action of a morphology transformation driving unit, and the photothermal conversion performance of the croconic acid cyanine dye can be effectively improved through morphology transformation; the synergistic treatment of photothermal and chemotherapy is realized, the tumor inhibition effect is further improved, and a good tumor treatment application prospect is achieved.

Description

technical field [0001] The invention belongs to the field of biomedicine, and in particular relates to a polypeptide-dye conjugate with variable morphology, its preparation method and application. Background technique [0002] Utilizing the Enhanced Permeability and Retention Effect (EPR) to achieve targeted delivery of anti-tumor drug nanoparticles has become a common method for targeted tumor therapy. Through the EPR effect, the nanoparticles circulating in the body can be abnormally grown. The tumor blood vessel wall enters the tumor lesion site, thereby achieving the tumor killing effect. The abnormal growth of blood vessels in the tumor tissue leads to the increase of the vascular space. Usually, the tumor vascular space can increase to 380-780nm. Therefore, in order to effectively exert the EPR effect and realize the enrichment of nanoparticles in tumor sites, it is necessary to fine-tune the particle size of nanoparticles. When the particle size of the nanoparticle ...

Claims

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Application Information

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IPC IPC(8): A61K41/00A61K47/64A61K9/51A61P35/00
CPCA61K41/0052A61K47/645A61K9/5169A61P35/00
Inventor 周绍兵张凌田原
Owner SOUTHWEST JIAOTONG UNIV
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