Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Sulfated hyaluronic acid 2-octyldodecyl ester

A technology of octyldodecyl ester and hyaluronic acid, which is applied in the direction of microcapsules, capsule delivery, nanocapsules, etc.

Active Publication Date: 2019-08-06
CHINA PHARM UNIV
View PDF6 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] At present, there is no report on the use of sulfated hyaluronic acid grafted with Y-type fatty alcohol esters as anti-tumor nanomaterials

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Sulfated hyaluronic acid 2-octyldodecyl ester
  • Sulfated hyaluronic acid 2-octyldodecyl ester
  • Sulfated hyaluronic acid 2-octyldodecyl ester

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] The preparation of embodiment 1 hyaluronic acid tetrabutylammonium salt

[0029] Sodium hyaluronate (MW5000, HA-Na, 2.0g) was dissolved in 400mL double-distilled water, and magnetically stirred overnight at room temperature; another 20g DowexWX8 cation exchange resin (tetrabutylammonium type) was weighed and added to HA-Na, and magnetically stirred at room temperature Overnight, filter, lyophilize and vacuum-dry at 40°C to obtain hyaluronic acid tetrabutylammonium salt (HA-TeBA).

Embodiment 2

[0030] The preparation of embodiment 2 sulfated hyaluronic acid (sHA)

[0031] Accurately weigh the HA-TeBA (MW5000, 1000mg) in Example 1 and dissolve it in 50ml of N,N'-dimethylformamide (DMF), stir magnetically at 50°C for 2h to dissolve it; in addition, accurately weigh 1540mg of sulfated Sulfur trioxide DMF complex (SO 3DMF) was dissolved in 50mL DMF, stirred at room temperature until dissolved, then added to HA-TeBA, protected with nitrogen, stirred magnetically for 1h after ice bathing; adjusted pH to neutral with 1M NaOH solution, added ethanol for precipitation, centrifuged, and dialyzed with distilled water for 2d , freeze-dried in vacuum to obtain sulfated hyaluronic acid (sHA). The IR spectrum confirmed the structure of sHA (see figure 1 ). The degree of sulfation was determined by elemental analysis, and the sulfur content (S%) was 4.392%.

Embodiment 3

[0032] Example 3 Preparation of Sulfated Hyaluronic Acid 2-Octyldodecanyl Ester (sHA-OCD)

[0033] Accurately weigh the sHA (100 mg) in Example 2 and dissolve it in 5 ml of formamide, stir magnetically at room temperature for 20 minutes to dissolve, then ice-bath, add 1-ethyl-(3-dimethylaminopropyl)carbodiethylene Amine hydrochloride (EDC, 95mg), N-hydroxysuccinimide (NHS, 58mg), react in ice bath for 2h; another precise amount of 2-octyldodecanol (OCD) was dissolved in 9mL of DMF , was added dropwise to the sHA solution, and stirred magnetically at 35°C for 24 hours; the reaction solution was precipitated with ethanol, centrifuged, dissolved in water, dialyzed in distilled water for 2 days, and freeze-dried in a vacuum to obtain sulfated hyaluronic acid 2-octyldodecyl ester ( sHA-OCD). 1 H-NMR spectrum (see figure 2 ) confirmed the sHA-OCD structure, and the substitution degree was about 10%.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

PropertyMeasurementUnit
degree of substitutionaaaaaaaaaa
Login to View More

Abstract

The invention relates to and provides a novel medicinal carrier sulfated hyaluronic acid 2-octyldodecanol ester, as well as a preparation method and application thereof. The sulfated hyaluronic acid 2-octyldodecanol ester is amphipathic since hydrophobic Y-shaped radical 2-octyldodecanol and hydrophilic sulfate radical are grafted on a hyaluronic acid framework, can be spontaneously assembled in water to form a non-linear polymeric micelle, can form a larger lyophobic cavity in comparison with a linear polymer micelle, and can carry more insoluble medicinal materials. The sulfated hyaluronic acid 2-octyldodecanol ester can be used for inhibiting tumor growth, nano-particles formed by the sulfated hyaluronic acid 2-octyldodecanol ester has the characteristics of small grain size, good stability, strong drug-loading capability, high encapsulation rate and simple preparation process.

Description

technical field [0001] The invention relates to the fields of polymer carrier materials and pharmaceutical preparations, in particular to a sulfated hyaluronic acid 2-octyldodecyl ester, a preparation method thereof, and an application as a drug carrier. Background technique [0002] Hyaluronic acid (Hyaluronan, HA) is a natural linear polysaccharide composed of N-acetyl-D-glucosamine and D-glucuronic acid linked by β-1,4 glycosidic bonds. HA has good water solubility, good biocompatibility, easy chemical modification, and has been widely used as a variety of drug carriers. The HA receptor CD44 on the surface of tumor cells is overexpressed, and hyaluronic acid can specifically bind to the receptor, which can target nanoparticles to tumors, and at the same time, endocytosis mediated by CD44 can allow drugs to enter tumor cells , to increase the bioavailability of poorly soluble drugs. However, the effects of HA with different molecular weights on the proliferation and meta...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C08B37/08A61K9/51A61K47/36
CPCA61K9/5161C08B37/0072
Inventor 栾立标易芳莲
Owner CHINA PHARM UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com