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Amino-containing diphosphonate modified Brij compound used as surfactant, and preparation method thereof

An amino bisphosphonate and surfactant technology, applied in the field of medicine, can solve the problems of non-universality, decrease and loss of drug activity, achieve high temperature stability and chemical stability, simple steps, and less environmental pollution Effect

Inactive Publication Date: 2014-10-08
SOUTHWEST JIAOTONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These modification methods are specific to the types of nanoparticles and their surface properties, and are not universal.
At the same time, the modification of nanoparticles is usually after the active drug is loaded, and the chemical reaction of the modification is likely to reduce or lose the activity of the drug.

Method used

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  • Amino-containing diphosphonate modified Brij compound used as surfactant, and preparation method thereof
  • Amino-containing diphosphonate modified Brij compound used as surfactant, and preparation method thereof
  • Amino-containing diphosphonate modified Brij compound used as surfactant, and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Embodiment 1: the preparation of the Brij78 that p-toluenesulfonyl chloride modifies

[0024] Weigh Brij78 (11.5g, 10mmol) and dissolve it in dichloromethane, add triethylamine (3.03g, 30mmol), add p-toluenesulfonyl chloride (3.8g, 20mmol) in batches while stirring in an ice bath, continue Stir overnight to make the reaction complete, remove dichloromethane by distillation under reduced pressure, redissolve the solid in ethanol, add concentrated hydrochloric acid, place the solution in a -20°C refrigerator, let it rest overnight, centrifuge at -10°C, 5000g for 5min, and obtain the correct solution. Crude product of Brij78 modified with methylbenzenesulfonyl chloride (13.22g).

Embodiment 2

[0025] Embodiment 2: the Brij78 of pamidronate disodium modification of the present invention

[0026] The Brij78 (13.22 g, 10 mmol) modified by p-toluenesulfonyl chloride obtained in Example 1 was dissolved in distilled water, sodium bicarbonate (4.2 g, 50 mmol) and disodium pamidronate (3.7 g, 10 mmol) were added, The solution was refluxed overnight to make the reaction complete, the solvent was distilled off under reduced pressure, the solid was redissolved in ethanol, filtered, the filtrate was evaporated to dryness, the solid was redissolved in petroleum ether, filtered, the solid was washed with the filtrate, and then washed three times with petroleum ether to obtain this product Pamidronate disodium-modified Brij78 (9.3 g) according to the invention.

[0027] see figure 1 , which is the proton nuclear magnetic resonance spectrum of Brij78 modified by disodium pamidronate provided in this example.

[0028] Combined with NMR images and compared figure 2 It can be seen...

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Abstract

The invention discloses an amino-containing diphosphonate modified Brij compound used as a surfactant, and a preparation method thereof. The compound is a surfactant with a calcium affinity effect, and is prepared through the steps of reacting a Brij serial compound with p-toluenesulfonyl chloride to prepare an intermediate and reacting the intermediate with diphosphonate. The amino-containing diphosphonate modified Brij compound reserves the good surface activity of the Brij serial compound and increases the affinity capability to calcium. The preparation method of the amino-containing diphosphonate modified Brij compound has the advantages of reliable principle, simple steps, easy operation, high safety of reactants and solvents used in the invention, and small pollution to environment. The amino-containing diphosphonate modified Brij compound has good high temperature stability and chemical stability, and varieties of medicine loaded nano-particles prepared by using the amino-containing diphosphonate modified Brij compound have calcium endophilicity and bone targeting property, and can be used in the technical field of medicines.

Description

technical field [0001] The invention belongs to the technical field of medicine, and relates to drug-loaded bioremediation materials, in particular to Brij series surfactants modified with amino-containing bisphosphonates and a preparation method thereof. Background technique [0002] Amino group-containing bisphosphonates (such as pamidronate disodium) have the following structural formula: [0003] [0004] R 1 for -CH 3 Or -OH; R is hydrogen, a monovalent metal salt or an alkyl group containing 1-4 carbons; n is 0-10. [0005] The bisphosphonates utilized in the present invention are a class of drugs used to strengthen bones. Bone is in a constant state of bone remodeling, in which new bone is produced by cells called osteoblasts and old bone is removed by cells called osteoclasts. Bisphosphonates inhibit bone removal (resorption) by osteoclasts. Bisphosphonates are used to treat bone pain from osteoporosis and diseases such as metastatic breast cancer, multiple m...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G65/00A61K47/34
Inventor 晏为力张家彬刘新荣
Owner SOUTHWEST JIAOTONG UNIV
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