Water-soluble host-guest compound as well as preparation and application thereof

A water-soluble, host-guest technology, which can be used in pharmaceutical combinations, organic active ingredients, and non-active ingredients medical preparations, etc., and can solve the problems of poor water solubility, few solubilizers and stabilizers

Active Publication Date: 2021-11-23
TIANJIN NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of the present invention is to develop a method for the practical problem that the leukemia treatment drug busulfan is easy to hydrolyze and has poor water solubility, and there are still few effective solubilizers and stabilizers. Water-soluble host-guest complex, which greatly improves the water solubility and stability of Busulfan

Method used

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  • Water-soluble host-guest compound as well as preparation and application thereof
  • Water-soluble host-guest compound as well as preparation and application thereof
  • Water-soluble host-guest compound as well as preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Synthesis of water-soluble host-guest complexes

[0018] Dissolve water-soluble pillararene (CP5A) in water and configure 8 × 10 -4 mol / L solution, add 0.5 equivalent of anticancer drug busulfan solid to the above solution, keep the temperature at 25°C, stir or ultrasonic for 30 minutes to dissolve, and the solution of water-soluble host-guest complex is obtained

[0019] The synthetic route of water-soluble host-guest complex is as follows:

[0020]

[0021] The structures of the water-soluble pillar aromatic hydrocarbon (CP5A) and busulfan are as follows:

[0022]

[0023] Water-soluble pillararene (CP5A) was synthesized according to literature (Ogoshi, T.; Hashizume, M.; Yamagishi, T.Chem. Commun. 2010, 46, 3708–3710.), and busulfan was purchased commercially.

[0024] The NMR data of the water-soluble host-guest complex are as follows:

[0025] 1 H NMR (400 MHz, D 2 O) δ 7.07 (s, 10H), 6.75 (s, 10H), 4.52 (dd, 20H), 4.27 (s, 20H), 3.91 (d, 20H), 3.14 (s, ...

Embodiment 2

[0027] Application of a water-soluble host-guest complex in the stabilization of the anticancer drug busulfan.

[0028] Such as figure 1 , adding water-soluble pillararene (CP5A) to busulfan, it can be clearly seen that the hydrogen on the methylene group of the guest busulfan moved to the high field by 2.3 and 3.6 ppm respectively, and the methyl hydrogen also moved to the high field 0.1 ppm, indicating that the butyl moiety of busulfan was included into the cavity of the main body CP5A. At the same time, the hydrogen on the water-soluble pillararene moved downfield by 0.3, 0.2, and 0.1 ppm, respectively, further indicating the formation of host-guest complexes. Such as figure 2 and 3 , Through nuclear magnetic monitoring, we found that busulfan itself will be rapidly hydrolyzed into tetrahydrofuran and methanesulfonic acid in aqueous solution. After 24 days, 90.7% of busulfan was hydrolyzed. For the complex, only 25.2% of busulfan was hydrolyzed at the same time, indica...

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Abstract

The invention discloses a water-soluble host-guest compound as well as a preparation and application thereof. Water-soluble pillararene is used as a macrocyclic carrier to act with an anticancer drug busulfan, so that the stability of the water-soluble host-guest compound is greatly improved, the hydrolysis rate of the water-soluble host-guest compound is reduced, and the water solubility of the water-soluble host-guest compound is improved. The water-soluble host-guest compound as well as the preparation and application thereof has the advantages that the raw materials of the water-soluble pillararene can be commercially purchased, the synthesis is simple and convenient, the yield is high, the operation of stabilizing anticancer drugs is simple and convenient, the stabilizing effect is good, the hydrolysis rate is greatly inhibited, the water solubility is improved, the problem of hydrolysis of busulfan drugs is expected to be solved. The application prospect in the aspects of treating leukemia and reducing toxic and side effects and the like is wide.

Description

technical field [0001] The invention belongs to the technical field of medicine preparation, and relates to the application of supramolecular macrocyclic water-soluble pillar aromatics in stabilizing the anticancer drug busulfan and increasing its water solubility. Background technique [0002] Leukemia is a malignant disease that threatens human health. Among them, chronic myelogenous leukemia is a malignant tumor that commonly occurs in the blood system of middle-aged people. Patients with this disease will produce a large number of neutrophils after illness. These granulocytes will accumulate in the bone marrow, thereby affecting the normal hematopoietic function of the body, leading to anemia, infection, and even death in patients. Busulfan (Busulfan in English) is the main chemotherapy drug for the treatment of chronic myelogenous leukemia, the remission rate can reach 80-90%, its main component is 1, 4-butanediol dimesylate, but during the Among them, busulfan has the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K47/69A61K31/255A61P35/02
CPCA61K31/255A61K47/6949A61P35/02
Inventor 张治元薛慧峰黄煜茜李春举刘越
Owner TIANJIN NORMAL UNIVERSITY
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