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PH-sensitive block polymer, FRET (fluorescence resonance energy transfer) composite and their preparation methods

A block polymer, polymer technology, applied in the FRET complex model and its preparation, the field of pH-sensitive block polymer, can solve the problem of inability to realize the integration of diagnosis and treatment in vivo and so on

Active Publication Date: 2016-11-16
WENZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the polymer micelles injected through the tail vein have no pH sensitivity, and there are no chemical sites for fluorescent labeling on the chain segments, so it is impossible to realize the integration of diagnosis and treatment in vivo
On the other hand, in existing patents, polyhistidine-polyethylene glycol-polycaprolactone (PLH-PEG-PCL) is used as a pH-sensitive polymer drug-carrying system. After in vivo injection, the loaded drug or fluorescent The labeled polymer will be taken up by various tissues in the body, and tumor imaging cannot be achieved under low background conditions

Method used

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  • PH-sensitive block polymer, FRET (fluorescence resonance energy transfer) composite and their preparation methods
  • PH-sensitive block polymer, FRET (fluorescence resonance energy transfer) composite and their preparation methods
  • PH-sensitive block polymer, FRET (fluorescence resonance energy transfer) composite and their preparation methods

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preparation example Construction

[0048] The preparation method of gold nanorods is as follows:

[0049] Synthetic gold species: 5mL 0.2mol / L CTAB (cetyltrimethylammonium bromide) mixed with 5mL 0.5mmol / L chloroauric acid, and then add 0.6mL 0.01mol / L of sodium borohydride, vigorously stirred for 5 minutes, and allowed to stand at room temperature for 2 hours, used as seed gold nanoparticles;

[0050] Synthesis of short gold nanorods by CTAB template method: take seven 25mL sample vials (marked as GNP-A1, GNP-A2, GNP-A3, GNP-A4, GNP-A5, GNP-A6, GNP-A7), Add 5mL 0.2mol / L CTAB aqueous solution respectively, and add different amounts of 4mmol / L AgNO 3 Aqueous solution (0.050, 0.10, 0.15, 0.20, 0.25, 0.30 and 0.40mL), then add 5mL of 1mmol / L chloroauric acid aqueous solution, at this time the color of the solution turns golden yellow, then add 70μL of 0.0788mol / L ascorbic acid , the solution becomes colorless instantly. Finally, 12 μL of seed gold nanoparticle dispersion was added respectively, and left to rea...

Embodiment 1

[0053] The preparation method of a kind of pH-sensitive block polymer of this embodiment (preparation process is as follows image 3 shown) as follows:

[0054] Use 1g of 2kDa Fmoc-NH-PEG-OH, 1.2g of caprolactone, and react under vacuum and nitrogen protection conditions at 130°C for 6 hours to synthesize Fmoc-NH-PEG-PCL (polymer of 2000-2000) through anhydrous ether Precipitate, dialyze and lyophilize;

[0055] Weigh 0.3mmol Fmoc-NH-PEG-PCL, 0.45mmol lipoic acid, 0.45mmol dicyclohexylcarbodiimide, 0.45mmol 4-dimethylaminopyridine, 0.3mL triethylamine and 0.3mL pyridine and add 30mL DMSO , react for 48 hours to prepare Fmoc-NH-PEG-PCL-LA;

[0056] Use 20% piperidine in dimethylformamide solution to remove the protective group at the amino terminal, that is, stir at 25°C for 10 minutes, and precipitate with anhydrous ether to prepare NH-PEG-PCL-LA;

[0057] Then the exposed amino group is used for ring-opening histidine anhydride, that is, using NH-PEG-PCL-LA ring-opening po...

Embodiment 2

[0061] The preparation method of a kind of pH-sensitive block polymer of the present embodiment is as follows:

[0062] Use 5kDa Fmoc-NH-PEG-OH to open ring caprolactone to a hydrophobic chain length of 10000Da to synthesize NH 2 -PEG-PCL (a polymer of 5000-10000);

[0063] 1g of 5kDa Fmoc-NH-PEG-OH, 3g of caprolactone, reacted at 170°C under vacuum and nitrogen protection for 6 hours to synthesize Fmoc-NH-PEG-PCL, precipitated with anhydrous ether, dialyzed and freeze-dried;

[0064] Weigh 0.3mmol Fmoc-NH-PEG-PCL, 0.45mmol lipoic acid, 0.45mmol dicyclohexylcarbodiimide, 0.45mmol 4-dimethylaminopyridine, 0.3mL triethylamine and 0.3mL pyridine and add 30mL DMSO In the solution, react for 48 hours to prepare Fmoc-NH-PEG-PCL-LA;

[0065] Use 20% piperidine in dimethylformamide solution to remove the protective group at the amino terminal, that is, stir at 25°C for 20 minutes, and precipitate with anhydrous ether to prepare NH-PEG-PCL-LA;

[0066] Then the exposed amino group i...

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Abstract

The present invention relates a PH-sensitive block polymer, a FRET (fluorescence resonance energy transfer) composite and their preparation methods; the PH-sensitive block polymer has a structure of polyhistidine-polyethylene glycol-polycaprolactone-lipoic acid, wherein the polyethylene glycol has a molecular weight of 2000-5000, the polycaprolactone has a molecular weight of 2000-10000, and chain segment length of the polyhistidine is composed of 10-30 histidines. The functionalized block copolymer polyhistidine-polyethylene glycol-polycaprolactone-lipoic acid (PLH-PEG-PCL-LA) is used to construct an integrated diagnostic and treatment model that is based on fluorescence resonance energy transfer (FRET) principle, may perform specific near-infrared imaging for a tumor acid microenvironment and engages in therapy. The model can mark a tumor acidic microenvironment to allow for real-time fluorescence imaging and can also transfer gold rods that are photosensitive particles to provide photothermal therapy for tumors.

Description

technical field [0001] The invention relates to the technical field of polymer materials, in particular to a pH-sensitive block polymer, a FRET complex model and a preparation method thereof. Background technique [0002] Fluorescence resonance energy transfer (FRET) is a highly sensitive, high spatial resolution, non-destructive homogeneous detection technology that combines fluorescence spectroscopy with resonance energy transfer. FRET means that within the distance of 1-10nm, when the emission spectrum of the donor overlaps with the absorption spectrum of the acceptor, due to the dipole-dipole interaction, the excited state energy of the donor is in the form of non-radiation delivered to the recipient. The energy transfer efficiency is inversely proportional to the sixth power of the distance R between the donor and acceptor. Therefore, FRET is called an effective optical "molecular ruler" in the range of 1.0-10.0 nm, and has been widely used in biological analysis. It ...

Claims

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Application Information

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IPC IPC(8): C08G63/08C08G63/91C08G69/16C08K3/08C08L77/02
CPCC08G63/08C08G63/912C08G69/16C08K3/08C08L77/02
Inventor 师帅李星熠何治芬陈浩
Owner WENZHOU MEDICAL UNIV
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