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Functionally synergistic zwitterionic lipids mediated by "water bridges" mediated superresponsiveness, and preparation methods and applications thereof

A zwitterion-mediated technology, which is applied in the field of material science and technology, and relates to a super-field of "water bridge" mediation, which achieves the effects of good blood compatibility, good circulation characteristics, and long circulation characteristics.

Active Publication Date: 2022-07-26
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

Method used

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  • Functionally synergistic zwitterionic lipids mediated by "water bridges" mediated superresponsiveness, and preparation methods and applications thereof
  • Functionally synergistic zwitterionic lipids mediated by "water bridges" mediated superresponsiveness, and preparation methods and applications thereof
  • Functionally synergistic zwitterionic lipids mediated by "water bridges" mediated superresponsiveness, and preparation methods and applications thereof

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Embodiment Construction

[0036] The lipid involved in the present invention is quaternized on the pyridine nitrogen atom in the final step of the synthesis process, and can be efficiently and massively prepared by microwave-assisted heating. figure 2 The yields of the quaternary amination reaction of the microwave-assisted heating of the present invention and conventional heating methods are shown.

[0037] The lipid DCPA described in the present invention can be assembled into nanoliposomes (DCPA-H 2 O), the average particle size is 100 nm, respectively; and the particle size and distribution coefficient are basically unchanged after one week of storage at room temperature. image 3 Liposome DCPA-H is shown 2 Particle size distribution of O.

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

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Abstract

The present invention relates to a functional synergistic zwitterionic lipid mediated by a "water bridge" mediated super-response, and a preparation method and application thereof. By fine-tuning the structure of carboxybetaine, the numerical value of its highest-level occupied orbital (HOMO) was increased, giving it pH responsiveness to composite water. A novel lipid named DCPA was synthesized by means of microwave-assisted heating. DCPA can be assembled into liposomes (DCPA‑H 2 O) Hydrophilic head groups can hydrogen bond with water to form "water bridges", which are protonated at pH<7. Neutral net charge under physiological conditions, prolongs blood circulation. In vivo experiments show that DCPA‑H 2 O liposome does not cause the increase of Ig M, and the half-life can reach 39h. In addition, through the observation of real-time imaging, DCPA‑H 2 O can target the infection site within 10 minutes, and the accumulation in the tumor site within 12 hours can reach 11 times as high as that of the whole body. Therefore, the present invention provides a brand-new and practical functional group, and the preparation method is simple and environmentally friendly, and has the potential of mass production.

Description

technical field [0001] The invention belongs to the technical field of material science, and relates to the preparation and application of a functional synergistic zwitterionic lipid mediated by "water bridge" mediated super-response, and specifically designs 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] In preclinical studies, self-targeting nanodrug carriers have made promising progress in the treatment of tumors and bacterial biofilm infections. A large number of literatures have reported that numerous self-targeting nanocarriers target tumor tissue and bacterial biofilm infection in weakly acidic microenvironment through the positive charge obtained by reversing their own charge through pH change and the electrostatic interaction of cell membrane. [0003] Among these numerous smart nanodrug carriers, pH-responsive function...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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