Application of nano-microsphere containing orlistat in preparing antineoplastic drugs

An anti-tumor drug, the technology of orlistat, which is applied in the field of medicine, can solve the problems of low solubility of orlistat, inability to obtain stable microspheres, and inability to administer orally

Active Publication Date: 2018-09-28
ZHONGSHAN WANHAN PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The development of orlistat antineoplastic drugs faces the following two restrictive problems: ① The bioavailability of orlistat in conventional oral preparations is extremely low (<2%), making it impossible to use oral administration for the treatment of HBV; Treatment; ② The solubility of orlistat in water is extremely low (<0.001g/100mL), making i...

Method used

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  • Application of nano-microsphere containing orlistat in preparing antineoplastic drugs
  • Application of nano-microsphere containing orlistat in preparing antineoplastic drugs
  • Application of nano-microsphere containing orlistat in preparing antineoplastic drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0090] Example 1 Preparation and structural confirmation of vitamin A methacrylate (compound 3a)

[0091]

[0092] Preparation: Take 28.65g vitamin A (0.100mol), place it in a 500mL three-necked flask, add petroleum ether to it under stirring until vitamin A is completely dissolved, and then add 5mg DCC(N,N'-dicyclohexyldi Imine), then add 13.21 g of methacrylic acid (compound 2, 0.15 mol) in saturated petroleum ether solution, slowly increase the temperature to 50° C. for reaction under stirring, and use high performance liquid chromatography to track the reaction to the end. The petroleum ether was distilled off under reduced pressure, and the obtained solid was washed with water and freeze-dried to obtain 31.55 g (0.089 mol) of a light yellow solid with a melting point of 51-52° C. and a yield of 89%.

[0093] Structure confirmation:

[0094] Compound 2: 1 H-NMR(CDCl 3 ) δ (ppm): 6.69 (1H, s), 6.55 (1H, s), 2.03 (3H, s).

[0095] Vitamin A: 1 H-NMR(CDCl 3 )δ(ppm): 6.55(1H, d), 6.5...

Embodiment 2

[0097] Example 2 Preparation and structural confirmation of vitamin E methacrylate (compound 3b)

[0098]

[0099] Preparation: Take 43.72g vitamin E (0.100mol) and place it in a 500mL three-necked flask, add ether to it with stirring until the vitamin E is completely dissolved, then add 5mg DMAP (4-dimethylaminopyridine) to it, and then add A saturated ether solution of 13.23 g of methacrylic acid (compound 2, 0.16 mol) was slowly heated to 50° C. for reaction under stirring, and the reaction was followed to the end by high performance liquid chromatography. The ether was distilled off under reduced pressure, and the obtained solid was washed with water and freeze-dried to obtain 45.39 g (0.091 mol) of an off-white solid with a melting point of 42-43° C. and a yield of 91%.

[0100] Structure confirmation:

[0101] Compound 2: 1 H-NMR(CDCl 3 ) δ (ppm): 6.69 (1H, s), 6.55 (1H, s), 2.03 (3H, s).

[0102] Vitamin E: 1 H-NMR(CDCl 3 )δ(ppm): 2.74 (2H, t), 2.12 (3H, s), 2.11 (3H, s), 2.11...

Embodiment 3

[0104] Example 3 Vitamin D 2 Preparation and structural confirmation of methacrylate (compound 3c)

[0105]

[0106] Preparation: Take 36.69g vitamin D 2 (0.101mol), placed in a 500mL three-necked flask, add ether to it under stirring until the vitamin E is completely dissolved, then add 5mg DMAP (4-dimethylaminopyridine), and then add 13.22g methacrylic acid (compound 2, 0.15 mol) of saturated ether solution, slowly heated to 50° C. for reaction under stirring, and followed the reaction to the end by high performance liquid chromatography. The ether was distilled off under reduced pressure, and the obtained solid was washed with water and freeze-dried to obtain 44.15 g (0.095 mol) of off-white solid with a melting point of 85-87° C. and a yield of 95%.

[0107] Structure confirmation:

[0108] Compound 2: 1 H-NMR(CDCl 3 ) δ (ppm): 6.69 (1H, s), 6.55 (1H, s), 2.03 (3H, s).

[0109] Vitamin D 2 : 1 H-NMR(CDCl 3 )δ(ppm): 6.43 (1H, d), 6.23 (1H, d), 5.48 (2H, s), 5.21 (1H, s), 5.17 (1H,...

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Abstract

The invention relates to the technical field of medicines, and in particular to an application of nano-microsphere containing orlistat in preparing antineoplastic drugs. The nano-microsphere consistsof the orlistat as well as any copolymer which is selected from a vitamin A methacrylate-2-methacryloyloxyethyl phosphorylcholine copolymer, a vitamin E methacrylate-2-methacryloyloxyethyl phosphorylcholine copolymer and a vitamin D methacrylate-2-methacryloyloxyethyl phosphorylcholine copolymer. Based upon in vitro test results, it is indicated that antineoplastic activity of the nano-microsphereprovided by the invention on human prostate cancer cells DU145, human melanoma cells A375 and human pancreatic cancer cell lines bxpc-3 is obviously higher than that caused by independent administration of the orlistat, and the antineoplastic activity is better than that of control nano-microsphere which is prepared by taking PMB30 as a carrier as well as nano-microsphere which contains the orlistat and polyethylene glycol-polycaprolactone.

Description

Technical field [0001] The present invention relates to the technical field of medicine, in particular to the use of nano-microspheres containing orlistat in preparing anti-tumor drugs. Background technique [0002] Fatty acid synthase (Fatty acid synthase, hereinafter referred to as FAS) is a key enzyme for fatty acid synthesis. This enzyme is in a state of low expression and low activity in normal cell tissues, while in breast cancer, prostate cancer, melanoma, pancreatic cancer, and retinoblastoma Tumor tissues such as tumors have high expression levels. Therefore, FAS is currently widely regarded as an ideal anti-tumor treatment target. [0003] Orlistat is a lipase inhibitor weight-loss drug marketed in Europe and the United States in the late 1990s and in China at the beginning of this century. It also has lipase inhibitor activity, so the drug is anti-tumor The role has attracted more and more attention in recent years. Pharmacological tests have shown that orlistat can ex...

Claims

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Application Information

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IPC IPC(8): A61K9/52A61K47/32A61K31/365A61P35/00
CPCA61K9/5026A61K31/365A61P35/00
Inventor 向飞杜志博彭韪
Owner ZHONGSHAN WANHAN PHARM CO LTD
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