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A biotin-targeted photosensitizer and quercetin nano-delivery system

A technology of biotin and nano-assembly, which is applied in drug combination, antineoplastic drugs, pharmaceutical formulations, etc., can solve the problems of low bioavailability and poor water solubility, and achieve targeting effect, water solubility improvement, and technical effect improvement Effect

Active Publication Date: 2020-09-25
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The delivery system has good water solubility, which solves the problems of poor water solubility and low bioavailability of quercetin and IR780, and also overcomes the tumor heat resistance of IR780 in photothermal therapy. Oncology drug candidates and combination therapy with photochemotherapy offer broad application prospects

Method used

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  • A biotin-targeted photosensitizer and quercetin nano-delivery system
  • A biotin-targeted photosensitizer and quercetin nano-delivery system
  • A biotin-targeted photosensitizer and quercetin nano-delivery system

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preparation example Construction

[0034] The second aspect of the present disclosure provides a preparation method of the compound described in the first aspect, the preparation method comprising the following steps:

[0035] (1) IR780 reacts with 3-amino-1-propanol to obtain IR780-OH;

[0036] (2) reacting the IR780-OH with biotin to obtain the compound described in the first aspect.

[0037] In some embodiments, the step (1) and / or (2) is a catalytic reaction, and the catalytic reaction is enzymatic catalysis or chemical catalysis; preferably, it is a chemical catalysis reaction.

[0038] In some embodiments, the IR780 in step (1) reacts with 3-amino-1-propanol under the condition of triethylamine.

[0039]Preferably, the concrete operation of described step (1) is as follows:

[0040] Dissolve IR780 in anhydrous N,N-dimethylformamide (DMF), add triethylamine, and react with 3-amino-1-propanol under inert gas protection and oil bath conditions to prepare the intermediate product IR780-OH.

[0041] Furthe...

Embodiment 1B780

[0064] Embodiment 1 B780 molecular synthesis

[0065] Weigh a certain amount of IR780 with an analytical balance, dissolve them in anhydrous N, N-dimethylformamide (DMF) and place them in a y round-bottomed flask, add triethylamine and 3-amino-1 -propanol, under nitrogen protection, and react in an oil bath at 85° C. for 4 h, wherein the molar weight is IR780: 3-amino-1-propanol: triethylamine = 1:5:0.6. After the reaction was completed, the anhydrous DMF was removed by rotary evaporation under reduced pressure, and the crude product was obtained by vacuum drying overnight. The crude product was dissolved in methanol, mixed with silica gel for a little column chromatography, purified by silica gel column chromatography, and gradient eluted with dichloromethane and methanol (100:1), to obtain pure IR780-OH as a blue solid. Weigh a certain amount of biotin and dissolve it in 5mL of anhydrous DMF, slowly drop DMAP and EDCI into the above solution under stirring conditions, activ...

Embodiment 2

[0066] Embodiment 2 Proton nuclear magnetic resonance spectrum ( 1 H-NMR) to identify the chemical structure of B780

[0067] About 5 mg of B780 was weighed, dissolved in deuterated dimethyl sulfoxide (DMSO-d6) and placed in an NMR tube, and its H NMR spectrum was measured by 400 MHz H NMR spectrum, and the chemical shift value (ppm) of the compound was recorded. The result is as figure 1 As shown, the NMR results can confirm that the molar ratio of IR780-OH and biotin in the newly synthesized molecule is close to 1:1, which can confirm the successful synthesis of B780.

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Abstract

The invention relates to the technical field of a nano-drug delivery system, in particular to a biotin target-modified photosensitizer and a quercetin nano-drug delivery system, aiming to overcome thepoor water solubility and the low bioavailability of a photochemotherapy agent and the quercetin, and the defect of tumor tolerance caused by the photosensitizers in the prior art. The biotin-modified IR780 is co-assembled with the quercetin to form a nanosystem for the first time, not only the shortcomings that the quercetin and the IR780 are insoluble in water and the bioavailability is low aresolved, but also the cancer tolerance caused by the photosensitizers is overcome. The prepared B780 / QuNPs nano-assembly with a diameter of 130 nm, conforms to the size range of tumor infiltration andretention effect, and has good passive and active targeting.

Description

technical field [0001] The disclosure relates to the technical field of nano drug delivery system, in particular to a nano drug delivery system formed by carrier-free self-assembly of biotin-targeted photosensitizer B780 and quercetin, its preparation method and application. Background technique [0002] The information disclosed in this Background section is only intended to increase the understanding of the general background of the disclosure, and is not necessarily to be taken as an acknowledgment or any form of suggestion that the information constitutes prior art that is already known to those skilled in the art. [0003] With the deepening of cancer research, combined photochemotherapy has become a promising treatment. Phototherapy mainly includes photothermal therapy and photodynamic therapy, which has the advantages of non-invasiveness and real-time monitoring by fluorescence imaging, such as IR780. However, most photosensitizers also have inevitable defects, such ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K47/54A61K41/00A61K31/4188A61K31/352A61P35/00C07D495/04
Inventor 栾玉霞田海隆
Owner SHANDONG UNIV
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