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A shape-variable polypeptide-dye conjugate, its preparation method and application

A technology of conjugates and dyes, which is applied in the field of biomedicine, can solve the problems of low stability of photothermal dyes and low photothermal conversion efficiency, and achieve the effects of improving delivery efficiency, enhancing residence time, and improving photothermal performance

Active Publication Date: 2022-06-03
SOUTHWEST JIAOTONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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

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  • A shape-variable polypeptide-dye conjugate, its preparation method and application
  • A shape-variable polypeptide-dye conjugate, its preparation method and application
  • A shape-variable polypeptide-dye conjugate, its preparation method and application

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Embodiment 1

[0039] This embodiment provides a polypeptide-dye conjugate with variable morphology, marked with CR-KLA, and the polypeptide-dye conjugate comprises a hydrophilic pro-apoptotic polypeptide sequence, a hydrophobic ketone acid cyanine dye derivative and a spacer molecule Ahx for linking the two fragments to form an amphiphilic photothermal dye conjugate, wherein the hydrophobic ketoacid cyanine dye derivative includes a ketoacid cyanine dye CR and a cyanine dye CR linked thereto through an amide reaction KLVFFGFLG sequence, the KLVFFGFLG sequence can be specifically recognized by the biological enzyme Cathepsin B overexpressed in tumor cells, and the GFLG sequence can be cleaved into two parts from the phenylalanine F and leucine L sites, so that the amphipathic The hydrophilic and hydrophobic segments of the photothermal dye conjugates are separated for structural reorganization, resulting in morphological changes.

[0040] Specifically, the polypeptide-dye conjugate CR-KLA ha...

Embodiment 2

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

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

[0051] First weigh 300 mg of Rink resin, swell with N,N-dimethylformamide DMF for 30min, prepare a deprotection solution (70% morpholine, 30% DMF) and add it to Rink resin to remove Fmoc protection on the resin group, the N-terminal amino group was exposed, after which it was washed three times with DMF and DCM, respectively. The required amino acid and HATU were weighed and dissolved in DMF, and then DIPEA was added to adjust the base, and then added to the resin for reaction. Each amino acid was reacted twice for 2 hours each time.

[0052] S2. Weigh 1.5 equivalents of ketone acid cyanine dye and 0-(7-azabenzotriazole)-N,N,N',N'-tetr...

Embodiment 3

[0058] In order to verify the photothermal properties of CR-KLA under two different nano-self-assembled morphologies, the prepared CR-KLA nanoparticles and nanofibers were exposed to 808 nm near-infrared light at 1w / cm2. 2 Irradiate the power for 10min respectively, and record the temperature value every 30s to obtain as follows: Figure 5 The heating curve shown in the figure. The inventor creatively found that after irradiation for 10 min, the ΔT of the CR-KLA nanoparticle morphology group was stable at 15.5 °C, and the ΔT of the CR-KLA nanofiber morphology group was stable at 23.5 °C, while the PBS group did not show the ability to heat up. Compared with the nanoparticles formed by the nanofibers formed by the croconic acid cyanine polypeptide material, the temperature change value ΔT increased by 8 °C under the same illumination time and light intensity, which proves that the photoelectricity of the croconic acid cyanine dye after the morphology transformation is improved....

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Abstract

The invention discloses a polypeptide-croketocyanine dye conjugate with variable morphology and its preparation method and application. The polypeptide-dye conjugate comprises a hydrophilic functional peptide segment and a hydrophobic croketocyanine dye segment and the spacer molecule Ahx used to connect the hydrophilic functional peptide segment and the hydrophobic dye segment, wherein the hydrophobic dye segment contains a shape adaptation unit that can realize shape transformation, and the polypeptide-dye conjugate The shape transformation can occur through the specific recognition or interaction of the shape transformation drive unit and the shape adaptation unit, and the self-assembly of the peptide-crotonate cyanine dye conjugate under polar conditions forms a nanoparticle with stable structure, and Under the specific action of the shape transformation driving unit, the morphology of nanofibers is transformed, and the transformation of the morphology can effectively improve the photothermal conversion performance of the croconic acid cyanine dye, and realize the synergistic treatment of photothermal and chemotherapy to further improve the tumor inhibition effect. It has a good application prospect in tumor therapy.

Description

technical field [0001] The invention belongs to the field of biomedicine, and in particular relates to a polypeptide-dye conjugate with variable morphology and a preparation method and application. Background technique [0002] Using the Enhanced Permeability and Retention Effect (EPR) to achieve targeted delivery of antitumor drug nanoparticles has become a common method for tumor targeted therapy. Through the EPR effect, the circulating nanoparticles can be made to grow abnormally. The tumor blood vessel wall enters the tumor lesion site, thereby achieving tumor killing effect. The abnormal growth of blood vessels in tumor tissue leads to the enlargement 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 at the tumor site, it is necessary to finely control the particle size of nanoparticles. When the nanoparticle size is small, its penetrat...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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