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Design and synthesis of artificial ion channels of amphiphilic molecules based on supramolecular self assembly

Author: LinYao
Tutor: BaoChunYan; ZhuZuoYong
School: East China University of Science and Technology
Course: Applied Chemistry
Keywords: Artificial ion channels Crown ether Azobenzene Photo-responsive Supramolecular self-assembly
CLC: O621.3
Type: Master's thesis
Year: 2013
Downloads: 107
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The normal function of ion channels in the cell membrane is the premise to maintain the normal metabolism of the cells and the exchange with the surrounding environment. The collapse of the structure or the function abnormalities of ion channel always lead to physiological dysfunction in the body to form various of congenital or acquired ion channel disease. So far, the study of ion channel diseases mainly involve K+, Na+, Ca2+and Cl-channel diseases which are always hard to be checked and diagnosed by conventional instruments in time. Therefore, the design and preparation artificial ion channels with the properties of ion selectivity and gating control (open or close by the external environment stimulus) as the normal ones by chemical synthesis methods will have important theoretical and practical significance for in-depth studying the action and disease mechanism of nature ion channels and thus resolving the plight of ion channel disease. Herein, based on the design principles of constructing artificial ion channels by supramolecular self-assembly, series of amphiphilic small molecules were designed and synthesized, which are expected to form ion channels in the bilayer lipid membranes by supramolecular self-assembly. By changing each functional component, a molecular engineering for constructing artificial ion channels based on supramolecular self-assembly is carried out to achieve the best model of such artificial ion channels. Besides diversing the types of artificial ion channels, it will also be able to provide potential applications in the biomedical fields, such as channel diseases etc. The work of this paper includes the following two contents:1. The design and synthesis of new photo-responsive artificial ion channels based on crown ether and azobenzene functional moietiesFive series of amphiphilic small molecules were designed and synthesized using benzocrown ether as channel structure and azobenzene as the light-responsive unit. By changing the functional components of the molecules, the supramolecular self-assembly performance of the molecules were compared by gel tests, from which A4-B4series with stronger supramolecular self-assembly ability was selected as the key object, and similar A5-B5series as the contrast, to study their ion channel performance, including their light-gating properties. Dye-encapsuled large unilamellar vesicles (LUVs) fluorescence measurements (HPTS) confirmed that the designed compounds not only could self-assembled in the membrane to form ion channel, but also showed ion selectively with different size of crown ether. Finally, the ion transport properties before and after light irradiation were also performed.2. The design and synthesis of oligo phenylene acetylene artificial ion channels In accordance with the double-layer film structure and the required structure of transmembrane molecules, oligo phenylene acetylene rigid-rod structure was synthesized as a main transmembrane structure which can be optimized to match the membrane thickness by changing the oligomeric number. And then, the branched chains with suitable size and structure for ion coordination (such as crown ether, semilumar substituents etc.) was introduced and arrayed to form ion channels through intramolecular supramolecular self-assembly. This part of the work so far mainly focused on the synthesis of "semilunar-like" side chain substituents and phenylene acetylene rigid-rod monomer, the polymerization and coupling reactions will be continued by other team members in laboratory.

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