Lys and oligopeptide-modified curcumin derivatives, and synthesis and medical application thereof

A technology of -ala-gly-asp-val and -arg-gly-asp-val, applied in the direction of medical preparations containing active ingredients, cyclic peptide ingredients, drug combinations, etc., can solve the problem that curcumin has no thrombolytic activity, etc. question

Inactive Publication Date: 2013-06-19
CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although curcumin has shown expected activity in the in vitro anti-platelet aggregation model, in vitro free radical scavenging model, rat arteriovenous bypass cannulation antithrombotic model and mouse ear swelling anti-inflammatory model, and these activities have no effect on cerebral ischemia Reperfusion injury, myocardial ischemia-reperfusion injury, and lung reperfusion injury all have protective effects, but curcumin has no thrombolytic activity, that is, the prerequisite for ischemia-reperfusion does not exist

Method used

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  • Lys and oligopeptide-modified curcumin derivatives, and synthesis and medical application thereof
  • Lys and oligopeptide-modified curcumin derivatives, and synthesis and medical application thereof
  • Lys and oligopeptide-modified curcumin derivatives, and synthesis and medical application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] Embodiment 1 prepares Boc-Pro-Ala-Lys (Boc)

[0059] 1) Preparation of Boc-Pro-Ala

[0060] 1.075g (5.0mmol) of Boc-Pro was dissolved in 20mL of anhydrous THF, and 0.637g (5mmol) of N-hydroxysuccinimide (HOSu) was added to the solution under ice cooling, and completely dissolved. Under ice-cooling, 1.236 g (6.0 mmol) of dicyclohexylcarbodiimide (DCC) dissolved in a small amount of anhydrous THF was added to the reaction solution. Stir at room temperature for 7 h, and monitor the disappearance of Boc-Pro by TLC (petroleum ether / ethyl acetate, 3:1). Dicyclohexylurea (DCU) was filtered off, and the filtrate was concentrated under reduced pressure to remove THF. The residue was dissolved with ethyl acetate, and the solution was successively washed with saturated NaHCO 3 After washing with aqueous solution and saturated NaCl aqueous solution, the ethyl acetate layer was concentrated to dryness under reduced pressure, the residue was dissolved by adding an appropriate amou...

Embodiment 2

[0065] Example 2 Preparation of Arg-Gly-Asp(OBzl)-Val-OBzl

[0066] 1) Preparation of Boc-Arg-Gly-OBzl

[0067] According to the preparation method of item 2) in Example 1, 1.600 g (5.0 mmol) Boc-Arg and 1.689 g (5.0 mmol) Gly-OBzl were reacted to obtain 2.26 g (97%) of the title compound as a pale yellow solid. ESI-MS(m / e): 421.7[M+H] + .

[0068] 2) Preparation of Boc-Arg-Gly

[0069] According to the preparation method in item 3) of Example 1, 1.630 g (3.5 mmol) of Boc-Arg-Gly-Obzl was hydrolyzed to obtain 1.236 g (94%) of the title compound as a colorless solid. ESI-MS(m / e): 331.3[M-H] - .

[0070] 3) Preparation of Boc-Asp(OBzl)-Val-OBzl

[0071] According to the preparation method of item 2) in Example 1, 2.871 g (97%) of the title compound was obtained as a colorless oil from 1.620 g (5.0 mmol) Boc-D (OBzl) and 1.607 g (5.0 mmol) Val-OBzl. ESI-MS(m / e): 512[M+H] + .

[0072] 4) Preparation of Asp(OBzl)-Val-OBzl

[0073] Dissolve 5.12g (10mmol) Boc-Asp(OBzl)-Val...

Embodiment 3

[0078] Example 3 Preparation of Ala-Gly-Asp(OBzl)-Val-OBzl

[0079] 1) Preparation of Boc-Ala-Gly-OBzl

[0080] According to the preparation method of item 2) in Example 1, 1.600 g (5.0 mmol) Boc-Ala and 1.689 g (5.0 mmol) Gly-OBzl were reacted to obtain 2.26 g (97%) of the title compound as a pale yellow solid. ESI-MS(m / e): 337[M+H] + .

[0081] 2) Preparation of Boc-Ala-Gly

[0082] According to the preparation method of item 3) in Example 1, 1.236 g (94%) of the title compound was hydrolyzed from 1.630 g (3.5 mmol) of Boc-R-G-OBzl as a colorless solid. ESI-MS(m / e): 245[M-H] - .

[0083] 3) Preparation of Boc-Asp(OBzl)-Val-OBzl

[0084] According to the preparation method of item 2) in Example 1, 2.871 g (97%) of the title compound were obtained from 1.620 g (5.0 mmol) Boc-Asp (OBzl) and 1.607 g (5.0 mmol) Val-OBzl as a colorless oil. ESI-MS(m / e): 512[M+H] + .

[0085] 4) Preparation of Asp(OBzl)-Val-OBzl

[0086] According to the preparation method in item 4) of E...

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Abstract

The present invention discloses six pseudo-peptides of the general formula I, wherein R1 is H or CH3, and R2 is Lys or Lys (Pro-Ala-Lys)-Arg-Gly-Asp-Val or Lys (Pro-Ala-Lys)-Ala-Gly-Asp-Val. The present invention further discloses a preparation method and use thereof. The compounds of the present invention have excellent thrombolytic activity, antithrombotic activity, anti-inflammatory activity, and OH radical scavenging activity, and a nanostructure.

Description

technical field [0001] The present invention relates to 6 kinds of pseudopeptides of general formula I, wherein R 1 for H or CH 3 , R 2 is Lys or Lys(Pro-Ala-Lys)-Arg-Gly-Asp-Val or Lys(Pro-Ala-Lys)-Ala-Gly-Asp-Val. The invention further relates to their preparation and use. The compound of the present invention has excellent thrombolytic activity, antithrombotic activity, anti-inflammatory activity, OH free radical scavenging activity and nanometer structure. The invention belongs to the field of biomedicine. [0002] Background technique [0003] Curcumin is one of the active ingredients of turmeric. It has antithrombotic, anti-inflammatory and free radical scavenging activities. It is a safe and low-toxic natural product. The inflammatory response promotes the release of coagulation factors and platelet activation, while down-regulating natural anticoagulants and inhibiting fibrinolytic activity. The process of thrombus formation is accompanied by the transformati...

Claims

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Application Information

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IPC IPC(8): C07K7/52C07C235/20C07C231/12A61K38/12A61K31/198A61P7/02A61P29/00A61P39/06
CPCY02P20/55
Inventor 赵明彭师奇吴建辉王玉记王枫
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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