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Conjugate of SSA, PEG and anticancer drugs and preparation thereof

A technology of polyethylene glycol and somatostatin, applied in antitumor drugs, drug combinations, pharmaceutical formulations, etc., to achieve the effects of improving targeting, prolonging residence time, and reducing drug toxicity and side effects

Inactive Publication Date: 2011-07-06
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 literature on the coupling of somatostatin analogues, polyethylene glycol and antineoplastic drugs by introducing linkers into macromolecular conjugates with tumor targeting and long circulation functions and applying them to antineoplastic drug delivery systems and patent coverage

Method used

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  • Conjugate of SSA, PEG and anticancer drugs and preparation thereof
  • Conjugate of SSA, PEG and anticancer drugs and preparation thereof

Examples

Experimental program
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Embodiment 1

[0031] Preparation of octreotide-polyethylene glycol-paclitaxel conjugate (OCT-PEG-PTX) (with succinic anhydride as the linking arm)

[0032] (1) Dissolve 35 mg of paclitaxel (PTX) in pyridine, add 4 mg of succinic anhydride, and stir for 4 hours at room temperature. Pyridine was removed by rotary evaporation and dried in vacuo. Add an appropriate amount of double-distilled water, stir for 30 minutes, collect the precipitate by filtration, dissolve the precipitate in an appropriate amount of acetone, slowly add double-distilled water, collect the crystals, and dry in vacuum to obtain 2'-succinylpaclitaxel. MRI 1 HNMR and mass spectrometry MS determined its structure.

[0033] (2) 2'-succinyl paclitaxel obtained in (1) was dissolved in acetonitrile, and 200 mg H 2 N-PEG-COOH (PEG 5000 ), add 16 mg 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDC·HCl) and 10 mg N-hydroxysuccinimide (NHS), and stir at room temperature for 12 h. Take the above reaction soluti...

Embodiment 2

[0036] Preparation of octreotide-polyethylene glycol-paclitaxel conjugate (OCT-PEG-PTX) (with succinic acid as the linker)

[0037] (1) Dissolve 35 mg of paclitaxel (PTX) in pyridine, add 4 mg of succinic acid, and stir at room temperature for 4 hours. Pyridine was removed by rotary evaporation and dried in vacuo. Add an appropriate amount of double-distilled water, stir for 30 minutes, collect the precipitate by filtration, dissolve the precipitate in an appropriate amount of acetone, slowly add double-distilled water, collect the crystals, and dry in vacuum to obtain 2'-succinylpaclitaxel. MRI 1 HNMR and mass spectrometry MS determined its structure.

[0038] (2) 2'-succinyl paclitaxel obtained in (1) was dissolved in acetonitrile, and 200 mg H 2 N-PEG-COOH (PEG 5000 ), add 16 mg 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDC·HCl) and 10 mg N-hydroxysuccinimide (NHS), and stir at room temperature for 12 h. Take the above reaction solution, add anhydro...

Embodiment 3

[0041] Preparation of vapreotide-polyethylene glycol-paclitaxel conjugate (VAP-PEG-PTX) (with succinic anhydride as the linking arm)

[0042] (1) Dissolve 35 mg of paclitaxel (PTX) in pyridine, add 4 mg of succinic anhydride, and stir for 4 hours at room temperature. Pyridine was removed by rotary evaporation and dried in vacuo. Add an appropriate amount of double-distilled water, stir for 30 minutes, collect the precipitate by filtration, dissolve the precipitate in an appropriate amount of acetone, slowly add double-distilled water, collect the crystals, and dry in vacuum to obtain 2'-succinylpaclitaxel. MRI 1 HNMR and mass spectrometry MS determined its structure.

[0043] (2) 200mg (Boc) HN-PEG-CONHS (PEG 2000 ) was dissolved in an appropriate amount of acetonitrile, 40 mg of vapreotide was dissolved in an appropriate amount of N, N-dimethylformamide (DMF), the PEG solution was added dropwise to the vapreotide solution, and then 5 mg of dimethylaminopyridine (DMAP) was ...

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Abstract

The invention provides a conjugate of SSA (somatostatin analog), PEG (polyethylene glycol) and anticancer drugs and the preparation thereof. The macromolecule conjugate is made from the targeting group SSA, the hydrophilic long-chain PEG and the anticancer drugs by adopting linking arms through conjugating. The macromolecule conjugate has tumor-targeting property and long circulation function, can obviously improve the antitumor activity, reduces toxic side effect of the drugs, is more suitable for clinical application, and provides new ideas for research and development of the anticancer drugs.

Description

technical field [0001] The invention relates to a somatostatin analog-polyethylene glycol-antitumor drug conjugate and a preparation method thereof. The conjugate is formed by coupling a targeting group somatostatin analogue, a hydrophilic long-chain polyethylene glycol and an antineoplastic drug by introducing a connecting arm. The invention also relates to the preparation method and application of the conjugate. Compared with antineoplastic drugs, the conjugate has better tumor targeting and long circulation function. Background technique [0002] Malignant tumor is one of the serious diseases that endanger human health. At present, there are about 17 million malignant tumor patients in the world. In my country, the number of cancer patients is about 2 million to 2.4 million every year, and the death rate is 1.6 million to 1.8 million. In the early 1970s, the number of cancer patients in my country was about 900,000, and the number of deaths was about 700,000; in 2005, t...

Claims

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Application Information

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IPC IPC(8): A61K47/48A61P35/00A61K47/60
Inventor 霍美蓉周建平朱钦女邹爱峰王竞李静姚成丽
Owner CHINA PHARM UNIV
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