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CD-ROM molecular motor artificial ion transmission system with antibacterial and anti-tumor activity and application of CD-ROM molecular motor artificial ion transmission system

A molecular motor and optical drive technology, applied in the field of artificial ion transporters, can solve problems such as limiting the value of therapeutic applications, and achieve the effects of broad-spectrum antibacterial activity, controllable structure, and improving antibacterial activity.

Pending Publication Date: 2022-05-13
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most of the reported artificial ion transporters have limited their practical therapeutic applications due to relatively low ion transport activity and cell non-specificity.

Method used

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  • CD-ROM molecular motor artificial ion transmission system with antibacterial and anti-tumor activity and application of CD-ROM molecular motor artificial ion transmission system
  • CD-ROM molecular motor artificial ion transmission system with antibacterial and anti-tumor activity and application of CD-ROM molecular motor artificial ion transmission system
  • CD-ROM molecular motor artificial ion transmission system with antibacterial and anti-tumor activity and application of CD-ROM molecular motor artificial ion transmission system

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0069] Example 1 Synthesis of Molecule A of Optical Drive Molecular Motor Artificial Ion Transport System

[0070]

[0071] (1) Synthesis of Compound 1

[0072] AlCl 3 (10.4g, 78mmol) and methacryloyl chloride (3.8mL, 39mmol) in anhydrous dichloromethane (100mL) was cooled to -78°C, solid naphthalene was added slowly in portions, and the reaction was stirred at room temperature overnight. After the reaction was complete, the solution was poured into iced aqueous hydrochloric acid (1M, 100 mL), and the resulting mixture was extracted with diethyl ether (100 mL). Anhydrous NaSO for organic layer 4 It was dried, concentrated, and purified by silica gel column chromatography (petroleum ether:dichloromethane=10:1) to obtain oily compound 1.

[0073] The physical parameters of compound 1 are: 1 H NMR (400MHz, CDCl 3 ), δ9.16(d, J=8.5Hz, 1H), 8.01(d, J=8.5Hz, 1H), 7.86(d, J=8.3Hz, 1H), 7.65(t, J=7.9Hz, 1H ),7.54(t,J=8.0Hz,1H),7.46(d,J=7.5Hz,1H),3.45(dd,J=6.8Hz,1H),2.80(m,J=7...

Embodiment 2

[0107] Example 2 Synthesis of Molecule B of Optical Drive Molecular Motor Artificial Ion Transport System

[0108]

[0109] (1) The synthesis method of compound 1-9 refers to compound 1-9 in Example 1.

[0110] (2) Synthesis of Compound 10

[0111] Add isothiocyanate (2.92mmol) to 4-(4-aminophenyl)butanoic acid (0.50g, 2.92mmol) in dichloromethane, stir overnight at room temperature, spin dry, after recrystallization (dichloromethane : Petroleum ether=1:1) to obtain white solid compound 10. The physical parameters of compound 10 are: 1 H NMR (400MHz, CDCl 3 )δ11.93(s,1H),9.32(s,1H),7.86(s,1H),7.55–7.21(m,2H),7.06(dt,J=7.5,1.0Hz,2H),3.04(s ,3H),2.53(t,J=1.0Hz,2H),2.26(m,2H),1.76(m,2H). 13 C NMR (100MHz, CDCl 3 )δ181.45, 177.33, 139.32, 134.58, 127.69, 117.53, 34.33, 33.50, 30.05, 26.63. LR-MS (ESI) (m / z): [M] + calcd for C 12 h 16 N 2 o 2 S, 252.09, found 252.09.

[0112] (3) Synthesis of compound B

[0113] To a solution of compound 9 (0.1 g, 2.89 mmol) and com...

Embodiment 3

[0115] Example 3 Synthesis of Molecule C of Optical Drive Molecular Motor Artificial Ion Transport System

[0116]

[0117] (1) The synthesis method of compound 1-9 refers to compound 1-9 in Example 1.

[0118] (2) Synthesis of Compound 10

[0119] To a solution of 3,5-dibromophenol (4.0 g, 5 mmol) in acetonitrile (100 mL) was added 2-(tert-butoxycarbonylamino)ethyl bromide (7.1 g, 10 mmol) and potassium carbonate (4.4 g, 10 mmol), And the mixture was stirred overnight at 80 °C. Then the reaction solution was spin-dried, the resulting residue was dissolved in ethyl acetate and washed 3 times with saturated brine, the organic phase was dried with anhydrous sodium sulfate, spin-dried under reduced pressure, and the obtained crude product was further purified by column chromatography to obtain Compound 10 is a yellow liquid.

[0120] The physical parameters of compound 10 are: 1 H NMR (400MHz, CDCl 3 )δ7.24(s,1H),6.97(s,2H),5.06(s,1H),3.98(t,J=4.9Hz,2H),3.51(d,J=4.7Hz,2H)...

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Abstract

The invention discloses a light-driven molecular motor artificial ion transmission system with antibacterial and anti-tumor activity and application. The structural general formula of the optical drive molecular motor with large steric hindrance olefin and unidirectional rotation is as shown in any one of formula I to formula III. The optical drive molecular motor with polysubstituted large steric hindrance olefin provided by the invention is a transporter molecule which can be inserted into a phospholipid bilayer membrane to carry out optical controllable ion transmembrane transportation, and has the advantages of controllable structure, easiness in derivatization and the like. The transmembrane transport molecules can selectively carry out ion transmembrane transport, and the movement of the motor is driven by illumination to accelerate the ion transmembrane transport, so that the light space-time controllable precise gating ion transmembrane transport is realized. In addition, the molecule can realize transportation of light-regulated ions on cell membranes and bacterial membranes, destroys ion balance inside and outside cells to realize excellent photosensitive antibacterial and antitumor activity, and has a better application prospect in the field of biological medicines.

Description

technical field [0001] The invention belongs to the technical field of artificial ion transporters, and in particular relates to a light-gated artificial ion transport system with antibacterial and antitumor activities and its application in antibacterial and antitumor aspects. Background technique [0002] Cells are the basic unit of life activities. In order to maintain survival and promote metabolism, cells need to exchange nutrients and communicate information with the surrounding environment. Ion transporters are composed of special proteins produced by cells. They are alone or aggregated and embedded in the cell membrane to regulate the flow of corresponding ions into and out of cells, which is of great significance to the realization of various functions of cells. The transport of ions on the cell membrane is closely related to many life activities, and the abnormal function of ion transporters can cause many diseases, such as cystic fibrosis, congenital muscle spasm,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D409/14C07D335/12C07D405/14C07D519/00C07D323/00C07D335/08C07D409/04C07D407/14A61P35/00A61P35/02A61P31/04A61K41/00
CPCC07D409/14C07D335/12C07D405/14C07D519/00C07D323/00C07D335/08C07D409/04C07D407/14A61P35/00A61P35/02A61P31/04A61K41/0057
Inventor 包春燕曲大辉杨会婷易瑾昊叶凯庞施浩颜泽昕
Owner EAST CHINA UNIV OF SCI & TECH