gem-1mt amphiphilic small molecule compound and its preparation, preparation method and application

A small molecule compound and compound technology, applied in the field of medicine, can solve the problems of difficult drug delivery, GEM drug resistance, strong hydrophobicity, etc., and achieve the goal of reshaping the tumor immune microenvironment, high cell internalization efficiency, and high cell inhibition rate Effect

Active Publication Date: 2021-04-02
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] In order to solve the deficiencies of the prior art, the object of the present invention is to provide a GEM-1MT amphiphilic small molecule compound and its preparation, preparation method and application. Poor tropism, and the shortcomings of GEM drug resistance, poor stability, high toxicity, and difficult drug delivery in vivo, and the synergistic treatment of GEM and 1MT in the form of GEM-1MT can reshape the tumor immune microenvironment and enhance the anti-tumor effect

Method used

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  • gem-1mt amphiphilic small molecule compound and its preparation, preparation method and application

Examples

Experimental program
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Effect test

Embodiment 1

[0055] Example 1 Synthesis of GEM-1MT

[0056] A certain amount of Boc-1MT was accurately weighed with an analytical balance, dissolved in anhydrous dichloromethane, and placed in a round bottom flask. Weigh a certain amount of NHS and EDC, dissolve it in a mixed solvent of anhydrous N,N-dimethylformamide (DMF) and ethanol, add it to the stirring solution of Boc-1MT above, under nitrogen protection, at room temperature React for 12 hours. Among them, the ratio of Boc-1MT: NHS: EDC is 1:2:2. After 12 hours, accurately weigh a certain amount of 4-N-3'-O-bis(Boc)GEM and DMAP with an analytical balance, dissolve in Anhydrous dichloromethane was added dropwise to the above-mentioned mixed solution after the reaction, and the reaction was continued at room temperature for 48 hours. After the reaction was completed, anhydrous DMF, dichloromethane and ethanol were removed by rotary evaporation under reduced pressure, and dried in vacuo overnight to obtain a crude product. The cru...

Embodiment 2

[0059] Example 2 H NMR spectrum ( 1 H-NMR) identification of Boc-protected GEM-1MT and the chemical structure of GEM-1MT

[0060] Take by weighing about 5 mg each of GEM-1MT and GEM-1MT protected by Boc prepared by the method of Example 1, and use deuterated chloroform (DMSO-d6) and deuterated water (D 2 O) dissolved and placed in a nuclear magnetic tube, using a 400MHz proton nuclear magnetic resonance spectrometer to measure its proton nuclear magnetic resonance spectrum, and record the chemical shift value (ppm) of the compound. The result is as figure 1 As shown, the NMR results can confirm that the peaks of the raw material molecules GEM and 1MT appear in the newly synthesized molecules, confirming the successful synthesis of Boc-protected GEM-1MT and GEM-1MT.

Embodiment 3

[0061] Example 3 Preparation of GEM-1MT NPs

[0062] Accurately weigh about 10 mg of GEM-1MT prepared by the method in Example 1, and dissolve it in 200 μL of methanol. Then, under ultrasonic conditions, it was added dropwise to 1 mL of water. The mixture was continued to be sonicated for half an hour, and nanoaggregates formed spontaneously. Finally, methanol was completely evaporated at 30°C using a rotary evaporator under vacuum to obtain GEM-1MT NPs with a uniform particle size of about 95±5nm, suitable for intravenous injection.

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Abstract

The invention provides a GEM-1MT amphiphilic small molecular compound as well as a preparation, a preparation method and application thereof. The GEM-1MT amphiphilic small molecular compound has a chemical structure as shown in a formula (I) which is described in the specification, the defects that 1MT is insufficient in efficacy, poor in water solubility, high in hydrophobicity, poor in targetingproperty, poor in GEM drug resistance, poor in stability, high in toxicity and difficult to deliver in a drug carrier are overcome, and through GEM and 1MT synergistic treatment, the tumor immune microenvironment can be remodeled, and the anti-tumor effect is enhanced.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to GEM-1MT amphiphilic small molecule compound and its preparation, 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 present invention, and is not necessarily taken as an acknowledgment or any form of suggestion that the information constitutes the prior art already known to those skilled in the art. [0003] The occurrence and development of tumors are closely related to the immune function of the body. Through immune surveillance, the body can generate an effective immune response against tumor cells, thereby eliminating tumor cells. However, tumor cells can induce the body to produce immune tolerance to itself through various ways, leading to immune escape of tumor cells. Indoleamine 2,3-dioxygenase (IDO) is an intracellular heme...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H19/073C07H1/00A61K31/7068A61P35/00A61K47/69A61K47/55
CPCA61K47/55A61K47/6929A61P35/00C07H1/00C07H19/073
Inventor 栾玉霞周诗瑶
Owner SHANDONG UNIV
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