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Bionic double-chain phospholipid film monolithic column, and making method and application thereof

A double-chain phospholipid, monolithic column technology, applied in the field of chromatographic separation, can solve the problems of inability to effectively simulate the phospholipid environment of cell membranes, unfavorable orderly arrangement of PC functional groups, and decreased ability to predict the effect of drug membranes, etc., so as to overcome residual amino groups and silanol groups. , good permeability, good effect of acid and alkali resistance

Active Publication Date: 2016-01-13
JINAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the monolithic column may still not be able to truly simulate biofilms, because it introduces a long alkyl hydrophobic chain outside the double-chain PC, which will not only affect the hydrophobic environment of the entire biomimetic system, but may also be detrimental to the presence of PC functional groups on the monolithic column. The ordered arrangement of the surface can not effectively simulate the phospholipid environment of the cell membrane, which eventually leads to a decrease in the predictive ability of the drug membrane effect

Method used

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  • Bionic double-chain phospholipid film monolithic column, and making method and application thereof
  • Bionic double-chain phospholipid film monolithic column, and making method and application thereof
  • Bionic double-chain phospholipid film monolithic column, and making method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Preparation of the functional monomer 1-dodecanoyl-2-(11-methacrylamide-N-undecanoyl)-SN-glycerol-3-phosphocholine (MDSPC) in this example:

[0037] (1) In a dry three-necked flask, add 4g of 11-aminoundecanoic acid, 50mL of ethanol, 7mL of water, add 3g of sodium hydroxide at room temperature, stir until the mixture becomes clear, the reaction temperature is lowered to 0°C, slowly drop 2.7mL of methacryloyl chloride solution, continue to react for 3h, then return to room temperature and stir overnight. After the reaction stopped, the reaction liquid was concentrated under reduced pressure and the pH was adjusted to 2.0 with 1 mol / L dilute hydrochloric acid, and a large amount of white flocs were found to be formed. Finally, the floc was vacuum filtered and dried to obtain 3 g of intermediate 11-methacrylamide-N-undecanoic acid (MDS). NMR identified as: 1 HNMR (300MHz, CDCl 3 )δ1.29(m,12H),1.49-1.65(m,4H),1.96(s,3H),2.32-2.37(t,2H),3.27-3.34(m,2H),5.31-5.32(t, 1H), ...

Embodiment 2

[0042] Preparation of the biomimetic double-stranded phospholipid membrane monolithic column in this example:

[0043] The 1-dodecanoyl-2-(11-methacrylamide-N-undecanoyl)-SN-glycero-3-phosphocholine (MDSPC) synthesized in Example 1, and the cross-linking agent ethylene glycol Alcohol dimethacrylate (EDMA), porogen isopropanol (Isopropanol) and cyclohexanol (Cyclohexanol) mixture and initiator azobisisobutyronitrile (AIBN) were mixed, ultrasonic degassed for 5 minutes, poured into a modified quartz capillary column at a reaction temperature of 60°C for 12 hours, then connected to a high-pressure pump and rinsed with methanol to obtain a biomimetic double-stranded phospholipid membrane monolithic column (poly(MDSPC-co-EDMA)). The schematic diagram of the above reaction is shown in figure 2 shown. Wherein the mass ratio of MDSPC and crosslinking agent is 45:55, the mass ratio of isopropanol and cyclohexanol in porogen is 83.3:16.7, the sum of MDSPC and crosslinking agent quali...

Embodiment 3

[0047] Preparation of the biomimetic double-stranded phospholipid membrane monolithic column in this example:

[0048] The 1-dodecanoyl-2-(11-methacrylamide-N-undecanoyl)-SN-glycero-3-phosphocholine (MDSPC) synthesized in Example 1, and cross-linking agent (B Glycol dimethacrylate, EDMA), porogen (isopropanol mixed with cyclohexanol) and initiator (azobisisobutyronitrile, AIBN) were mixed, ultrasonic degassed for 5 minutes, poured into modified In the quartz capillary column, the reaction temperature is 60°C, react for 12 hours, connect the high-pressure pump and wash with acetonitrile, and obtain the biomimetic double-stranded phospholipid membrane monolithic column. Wherein the mass ratio of MDSPC and crosslinking agent is 45:55, the mass ratio of isopropanol and cyclohexanol in porogen is 83.3:16.7, the sum of MDSPC and crosslinking agent quality, and the mass ratio of porogen is 34.43:65.57, the mass of the initiator is 1% of the sum of the mass of MDSPC and the crosslink...

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Abstract

The invention belongs to the technical field of chromatographic separation, and discloses a bionic double-chain phospholipid film monolithic column, and a making method and an application thereof. The monolithic column is prepared through in-situ polymerization of 1-lauroyl-2-(11-methacrylamide-N-undecanoyl)-SN-glycerol-3-phosphorylcholine as a functional monomer in the presence of a cross-linking agent, a pore foaming agent and an initiator through a thermocatalytic reaction in a modified quartz capillary tube; and the bionic double-chain phospholipid film monolithic column has a continuous monolithic porous structure. The bionic double-chain phospholipid film monolithic column is prepared from 1-lauroyl-2-(11-methacrylamide-N-undecanoyl)-SN-glycerol-3-phosphorylcholine as the functional monomer, and the functional monomer is prepared from 1-lauroyl lysolecithin only through two-step chemical modification, so the preparation cost is reduced; and the monolithic column has good separation performance and good application prospect.

Description

technical field [0001] The invention belongs to the technical field of chromatographic separation, and in particular relates to a bionic double-chain phospholipid membrane integral column and a preparation method and application thereof. Background technique [0002] Phospholipid membrane chromatography, also known as immobilized artificial membrane chromatography (Immobilized Artificial Membrane, IAM), is a widely used biomembrane chromatography in new drug research. Because the structure of the stationary phase is similar to that of the cell membrane phospholipid layer, it has good biomimetic characteristics and has been successfully Applied to the prediction of small intestine absorption, blood-brain barrier permeability, transdermal absorption, in vivo distribution, and pharmacodynamic activity of drugs [ValkóKL, Nunhuck SB, Hill AP. -862; LiuYY, LiLL, DaiRJ, QuF, GengLN, LiXM, DengYL. Assessment of the Enzymatic Activity and Inhibition using HPFA with a Microreactor, Tr...

Claims

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Application Information

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IPC IPC(8): B01J20/285B01J20/30B01D15/34
Inventor 江正瑾王启钦朱培杰吴慧慧周海波赵祥龙
Owner JINAN UNIVERSITY
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