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Water bridge mediated superresponse functional synergistic zwitter-ion lipid as well as preparation method and application thereof

A zwitterion, lipid technology, applied in the field of material science and technology, involving a "water bridge" mediated super field

Active Publication Date: 2021-09-07
NANKAI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, usually the above mentioned functional groups face some big problems in terms of cytotoxicity and biocompatibility

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  • Water bridge mediated superresponse functional synergistic zwitter-ion lipid as well as preparation method and application thereof
  • Water bridge mediated superresponse functional synergistic zwitter-ion lipid as well as preparation method and application thereof
  • Water bridge mediated superresponse functional synergistic zwitter-ion lipid as well as preparation method and application thereof

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Embodiment Construction

[0036] The quaternization of the lipid in the last step of the pyridine nitrogen atom in the synthesis process involved in the present invention can be efficiently and massively prepared by means of microwave-assisted heating. figure 2 Shown are the yields of the quaternization reaction for microwave assisted heating of the present invention and conventional heating methods.

[0037] Lipid DCPA described in the present invention can be assembled into nano liposome (DCPA-H 2 (0), the average particle diameter is respectively 100nm; and the particle diameter and the distribution coefficient are substantially unchanged under room temperature conditions for a week. image 3 Liposome DCPA-H is shown 2 O particle size distribution.

[0038] The lipid DCPA described in the present invention can be complexed with water through hydrogen bonds. When the complexed water is at pH Figure 4 Proton NMR spectra are shown showing protonation in bound water at pH Figure 5 Proton NMR spectra...

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Abstract

The invention relates to a water bridge mediated superresponse functional synergistic zwitter-ion lipid as well as a preparation method and an application thereof. The value of the highest occupied molecular orbital (HOMO) of carboxy betaine is increased by finely adjusting the structure of the carboxy betaine, and the composite water pH responsiveness is given to the carboxy betaine. A novel lipid named as DCPA is synthesized by means of microwave-assisted heating. The DCPA can be assembled into a liposome (DCPA-H2O) hydrophilic head group, the hydrophilic head group can be combined with water through hydrogen bonds to form a water bridge, and protonation occurs when the pH value is smaller than 7. Under physiological conditions, the charge is neutral net charge, and blood circulation is prolonged. In-vivo experiments show that the DCPA-H2O liposome does not cause Ig M increase, and the half-life period can reach 39 h. Besides, through real-time imaging observation, DCPA-H2O can target an infected part within 10 minutes, and the cumulant of DCPA-H2O at a tumor part within 12 hours can be 11 times higher than that of the whole body. Therefore, the invention provides a brand-new practical functional group, and the preparation method is simple, convenient, green and environment-friendly, and has the potential of batch production.

Description

technical field [0001] The invention belongs to the field of material science and technology, and relates to the preparation and application of a super-responsive functional synergistic zwitterionic lipid mediated by a water bridge, specifically designing a novel lipid 2-(4-((1,5-bis( Synthesis and application of octadecyloxy)-1,5-dioxopentan-2-yl)carba-moyl)pyridin-1-ium-1-yl)acetate(DCPA) and its hydrophilic head. Background technique [0002] Self-targeting nano-drug carriers have made promising progress in the treatment of tumors and bacterial biofilm infections in preclinical studies. A large number of literatures have reported that numerous self-targeting nanocarriers target tumor tissue and bacterial biofilm infection in a weakly acidic microenvironment by changing the pH value to reverse their own charge to obtain positive charges and electrostatic interactions with cell membranes. [0003] Among these numerous smart nano-drug carriers, the pH-responsive functional ...

Claims

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Application Information

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IPC IPC(8): A61K9/127A61K47/24C07D213/81
CPCA61K9/127A61K47/24C07D213/81
Inventor 史林启王达远汉克·布什尔杨光亨尼·范德梅任意锦
Owner NANKAI UNIV
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