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Stearic acid grafted tetracycline, and preparation and application thereof

A technology of stearic acid and tetracycline, applied in the application field of tetracycline stearic acid graft and its preparation, and bone-targeted lipid nano drug delivery system, which can solve low bioavailability and non-targeted tissue and organ toxic side effects , No bone tissue targeting ability, etc.

Active Publication Date: 2016-08-24
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, as a water insoluble drug, statins have low bioavailability in the human body; they themselves do not have the ability to target bone tissue, so a large drug dosage must be required to achieve an osteogenic induction effect. Increased concentration in bone tissue
But this will bring unnecessary toxic side effects to other non-targeted tissues and organs, so it is of great significance to develop a targeting carrier suitable for statins

Method used

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  • Stearic acid grafted tetracycline, and preparation and application thereof
  • Stearic acid grafted tetracycline, and preparation and application thereof
  • Stearic acid grafted tetracycline, and preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Embodiment one: the synthesis of tetracycline stearic acid graft

[0021] Tetracycline stearic acid graft is synthesized by chemical reaction between the hydroxyl group of tetracycline and the carboxyl group of stearic acid. Specifically, it is realized through the following steps:

[0022] Accurately weigh 213mg of stearic acid, 216mg of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide, EDC), 150mg of 1-Hydroxybenzotriazole (Hydroxybenzotriazole, HOBT) was placed in a 100ml dry round bottom flask (the molar ratio of stearic acid, EDC and HOBT was 1:1.5:1.5), and 20ml of anhydrous dimethyl formazan was added Amide, stir at 60°C to dissolve all the reactants, and keep warm for 30min to activate the carboxyl group of stearic acid. Add 469 mg of tetracycline hydrochloride (Tetracycline, TC) (the molar ratio of stearic acid to tetracycline hydrochloride is 1:1.3) in the round bottom flask, and continue to react for 24 hours unde...

Embodiment 2

[0025] Example 2: Preparation of bone-targeted lipid nanocarrier containing 30% tetracycline stearic acid graft and its in vitro bone affinity

[0026] 1. Preparation of non-targeting lipid nanocarriers and their in vitro bone affinity.

[0027] Weigh 10 mg of lipid material (one of monoglyceride, stearic acid, glyceryl tristearate, and glyceryl behenate) and dissolve it in 1 ml of fluorescein isothiocyanate stearylamine graft respectively. In water ethanol, heat and dissolve in a water bath at 70°C (glyceryl tristearate and glyceryl behenate are 74°C), and the obtained organic phase is rapidly dispersed at 400rm to the same temperature of 70°C (glyceryl tristearate, glyceryl behenate is 70°C). Glyceryl behenate (74 DEG C) in 10ml poloxamer solution (0.1%, w / v), continued to stir for 5 minutes under water-bath conditions, cooled to room temperature, and obtained non-targeting lipid nanocarrier (being called for short lipid nanocarriers).

[0028] Take 2ml of poloxamer soluti...

Embodiment 3

[0035] Example 3. Preparation of bone-targeted lipid nanocarrier containing 50% tetracycline stearic acid graft and its in vitro bone affinity

[0036] Weigh 5 mg of monoglyceride, 1 mg of fluorescein isothiocyanate stearylamine graft and 5 mg of tetracycline stearic acid graft, dissolve in 1 ml of absolute ethanol, heat and dissolve in a water bath at 70 ° C, and obtain the organic phase at 400 rm Rapidly dispersed in 10ml poloxamer solution (0.1%, w / v) at the same temperature of 70°C, continued to stir for 5 minutes under water bath conditions, and cooled to room temperature to obtain the bone-targeting lipid containing tetracycline stearic acid graft nanocarriers.

[0037] Take 2ml of poloxamer solution + 20mg of hydroxyapatite, stir for 1h, centrifuge at 10000r for 5min, take the supernatant + 2ml of bone-targeting lipid nanocarriers and mix evenly to measure the fluorescence value as the control group. Take another 2ml of bone-targeting lipid nanocarrier + 2ml of poloxam...

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Abstract

The invention provides a stearic acid grafted tetracycline. A stearic acid grafted tetracycline is mixed with a lipid material for preparing a bone targeted lipid nanometer carrier; the bone affinity capability is realized; the bone targeting effect is achieved; the lipid material can more easily coat statin medicine. The stearic acid grafted tetracycline provided by the invention has the good affinity; the bone affinity is higher when the proportion of the stearic acid grafted tetracycline is higher; the stearic acid grafted tetracycline can be used for bone targeted carrier building; the prepared bone targeted nanometer carrier can also be used for oral administration. The structural formula of the stearic acid grafted tetracycline is shown as the accompanying description.

Description

technical field [0001] The invention belongs to the field of pharmacy, and relates to a tetracycline stearic acid graft, a preparation method thereof and an application in a bone-targeted lipid nano drug delivery system. Background technique [0002] Osteoporosis is a disease of the skeletal system characterized by degeneration of bone tissue microarchitecture, decreased bone mass, increased bone fragility, and increased risk of secondary fractures. According to the estimates of the World Health Organization (WHO), in 2012, there were more than 300 million people in the world who were at risk of osteoporosis; the data from the National Bureau of Statistics of China showed that in 2012, the total number of elderly people in my country was 117 million. , accounting for 8.7% of the total population, 0.9 percentage points higher than the world average, and the total elderly population is 1.3 times that of the United States, Japan and Russia combined. With the continuous expansio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C221/00C07C225/32A61K9/127A61K47/14
CPCA61K9/127A61K47/14C07C221/00C07C225/32
Inventor 赵蕊袁弘陈定伟陶珊王建卫胡富强
Owner ZHEJIANG UNIV
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