Chitose derivates using octreotide as target ligand and use thereof in medicament

A technology for chitosan derivatives and drugs, which is applied in the field of polymer chemistry to reduce toxic side effects and improve delivery efficiency.

Inactive Publication Date: 2009-04-01
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there is no research report on the modification of polymer materials and nanocarriers such as micelles and liposomes with octreotide

Method used

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  • Chitose derivates using octreotide as target ligand and use thereof in medicament
  • Chitose derivates using octreotide as target ligand and use thereof in medicament
  • Chitose derivates using octreotide as target ligand and use thereof in medicament

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] 1. Preparation of N-octyl chitosan (NOC)

[0039] Add 3.5g of chitosan, 105mL of water, and 2.2mL of acetic acid into a 500mL three-necked bottle and stir for 2 hours, raise the temperature to 30°C, and keep stirring for 2h. Add 105 mL of anhydrous methanol and 1 mL of acetic anhydride to the three-necked flask, keep the reaction for 6 hours, and adjust the pH of the reaction solution to 7 with 1 molL NaOH. Add 10.6mL octanal, react at room temperature for 36h, slowly add 5g KBH 4 , reduction reaction at room temperature for 24 hours, adjusted the pH of the reaction solution to 7, filtered, washed twice with water, four times with methanol, twice with ether, and dried to obtain 4.0 g of yellow powder (octyl substitution degree 65%).

[0040] 2. Preparation of N-octyl-N-succinyl chitosan (NONSC)

[0041] Take 1g of N-octyl chitosan, suspend it in 50mL dimethyl sulfoxide, stir for 1h, add 0.56g of succinic anhydride, stir vigorously at 80°C for 24h, adjust the pH of the...

Embodiment 2

[0049] 1. Preparation of N-nonyl chitosan (NNC)

[0050] Use chitosan to react with acetic anhydride and nonanal, use KBH 4 Reduction, that is, the preparation method is the same as that of NOC in Example 1.

[0051] 2. Preparation of N-nonyl-N-succinyl chitosan (NNNSC)

[0052] It is prepared by reacting N-nonyl chitosan with succinic anhydride, and the preparation method is the same as that of NONSC in Example 1.

[0053] 3. Preparation of N-nonyl-N-succinyl chitosan grafted with octreotide (NNNSOC)

[0054] It is prepared by reacting N-nonyl-N-succinyl chitosan with octreotide, and the preparation method is the same as that of NONSOC in Example 1.

[0055] NNNSOC:

[0056] FT-IR: 3428, 2951, 2871, 1728, 1669, 1656, 1551, 1426, 1381, 1315, 1258, 1231, 1151, 1116, 1071,

[0057] 1036,868cm -1 .

[0058] 1 H NMR (500MHz, D 2 O): 7.5-6.9 (arom Phe), 4.6-4.5 (Hα Thr, Hα Lys, H 1 ), 4.2 (Hβ Thr), 4.1-4.0 (Hβ Thr-ol), 4.0-3.4 (H 3 , H 4 , H 5 , H 6 ), 3.2 (-NH-C H ...

Embodiment 3

[0061] 1. Preparation of N-Lauryl Chitosan (NLC)

[0062] Use chitosan to react with acetic anhydride and lauryl aldehyde, use KBH 4 Reduction, that is, the preparation method is the same as that of NOC in Example 1.

[0063] 2. Preparation of N-dodecyl-N-succinyl chitosan (NLNSC)

[0064] It is prepared by reacting N-dodecyl chitosan with succinic anhydride, and the preparation method is the same as that of NONSC in Example 1.

[0065] 3. Preparation of N-dodecyl-N-succinyl chitosan grafted with octreotide (NLNSOC)

[0066] It is prepared by reacting N-dodecyl-N-succinyl chitosan with octreotide, and the preparation method is the same as that of NONSOC in Example 1.

[0067] NLNSOC:

[0068] FT-IR: 3423, 2956, 2863, 1729, 1668, 1656, 1549, 1420, 1381, 1316, 1259, 1236, 1158, 1112, 1066, 1033, 869cm -1 .

[0069] 1 H NMR (500MHz, D 2 O): 7.5-6.9 (arom Phe), 4.6-4.5 (Hα Thr, Hα Lys, H 1 ), 4.2 (Hβ Thr), 4.1-4.0 (Hβ Thr-ol), 4.0-3.3 (H 3 , H 4 , H 5 , H 6), 3.2 (-NH...

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Abstract

The invention relates to the field of polymer chemistry and the field of pharmaceutical excipients. The invention particularly relates to targeted chitosan derivatives (I) or (II) containing octreotide, in particular to the N-succinyl-N-alkylate chitosan derivative and the N-alkylate carboxymethyl chitosan and a preparation method thereof, the invention further relates to an effect thereof as a solubilizer of an insoluble drug, a modification effect on micelles, liposomes and other vectors and a pharmaceutical composition which leads the derivatives to have the target function and contains the derivatives.

Description

technical field [0001] The invention relates to the field of polymer chemistry and the field of pharmaceutical auxiliary materials. Specifically related to targeted chitosan derivatives containing octreotide, especially N-succinylated-N-alkylated chitosan derivatives and N-alkylated carboxymethylated chitosan derivatives capable of forming amphiphilic polymer molecules Chitosan and its preparation method, the present invention also relates to its function as a poorly soluble drug solubilizer, its modification to micelles, liposomes and other carriers, so that it has targeting function and the pharmaceutical composition containing it. Background technique [0002] Nanotechnology and biodegradable polymer materials are the current research hotspots in drug delivery systems. Combining the advantages of the two, polymer micelles are biodegradable and can form drug nanocarriers. As drug carriers, they can provide a series of incomparable advantages: solubilizing insoluble drugs,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K47/48A61K9/00A61K9/127A61K38/12A61K31/337A61K31/4745A61K31/704C08B37/08A61P35/00A61K9/107A61K47/36
Inventor 平其能张灿张鹏申慰王宇
Owner CHINA PHARM UNIV
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