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Method of modulating membrane potential of a cell

A technology of cell membrane and membrane potential, applied in pharmaceutical formulations, medical preparations containing active ingredients, cardiovascular system diseases, etc.

Active Publication Date: 2011-08-31
VERSITECH LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, to date, no synthetic ion channels have been reported capable of establishing membrane potential and / or modulating native voltage-dependent ion channels in living systems.

Method used

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  • Method of modulating membrane potential of a cell
  • Method of modulating membrane potential of a cell
  • Method of modulating membrane potential of a cell

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0204] Preparation of Example 1

[0205]

[0206] Process A

[0207] Example 1 was prepared according to Scheme A above. According to Yang et al., J.Org.Chem, 2001, 66, 7303-7312 described procedure synthesis starting material 2-phthalimidoxy (phthalimidoxy)-4-methylpentanoic acid D-tert-butyl ester ( Compound 1). Compound 1 is a white crystalline solid characterized by the following data: melting point 92-93 °C; [α] 20 D +77.0° (c 1.01, CHCl 3 ); 1 H NMR (300MHz, CDCl 3 )δ7.85-7.81 (m, 2H), 7.78-7.74 (m, 2H), 4.74 (dd, J=8.5, 5.4Hz, 1H), 2.05-1.91 (m, 2H), 1.72-1.63 (m, 1H), 1.46(s, 9H), 1.07(d, J=6.3Hz, 3H), 1.00(d, J=6.3Hz, 3H); 13 C NMR (75MHz, CDCl 3 )δ169.13, 163.21, 134.50, 128.87, 123.53, 84.74, 83.39, 39.89, 27.82, 24.47, 22.90, 21.96; IR (CHCl 3 )3032, 1793, 1738cm -1 ; LRMS (EI, 70ev) m / z 333 (M + , 1), 278(6), 232(17), 164(15), 148(100); C 18 h 23 NO 5 (M + ) HRMS (EI): theoretical value 333.1576, measured value 333.1573.

[0208] To the CH of c...

Embodiment 2

[0210] Preparation of Example 2

[0211]

[0212] Process B

[0213] Example 2 was prepared according to Scheme B above. CH 2 Cl 2 (5mL) solution was carefully added an equal volume of CF 3 COOH (5 mL). After stirring at room temperature for 3 hours, the reaction mixture was concentrated in vacuo. The residue was azeotroped twice with toluene to give the free acid compound 3 as a white solid which was used directly for peptide coupling.

[0214] Freshly distilled CH 2 Cl 2 (50 mL) was added to the flask containing dry free acid compound 3, followed by HOAt (354 mg, 2.6 mmol), isobutylamine (0.21 mL, 2.1 mmol) and finally EDCI (891 mg, 3.0 mmol). After overnight stirring, CH 2 Cl 2 Dilute the reaction mixture. Organic layer with 5% NaHCO 3 and brine, followed by anhydrous MgSO 4 Dried and concentrated. The crude oil was purified by flash column chromatography to afford 492 mg of Example 2 (92% yield) as a white solid. Example 2 is characterized by the followin...

Embodiment 3

[0215] Preparation of Example 3

[0216]

[0217] Process C

[0218] Example 3 was prepared following Scheme C above similar to Scheme B for Example 2, except that decylamine was substituted for isobutylamine. Example 3 isolated as a colorless oil. Example 3 is characterized by the following data: [α] 20 D +34.5° (c 1.00, CHCl 3 ); 1 H NMR (400MHz, CDCl 3 )δ11.32(s, 2H), 8.28(br, 2H), 8.19(s, 1H), 8.05(d, J=7.5Hz, 2H), 7.52(t, J=7.5Hz, 1H), 4.38( br, 2H), 3.13-3.02(m, 4H), 1.82(m, 2H), 1.65-1.55(m, 4H), 1.42(br, 4H), 1.35-1.25(m, 28H), 0.89-0.85( m,18H); 13 C NMR (100MHz, CDCl 3 )δ172.30, 165.91, 132.05, 131.29, 129.37, 124.98, 85.31, 41.17, 39.47, 31.89, 29.55, 29.53, 29.30, 29.12, 26.91, 24.73, 23.18, 22.67, 21.79; IR, 14.Cl 3 )3446, 1662cm -1 ; LRMS (FAB) m / z 704 (M + , 1); C 40 h 71 N 4 o 6 (M + , 1) HRMS (FAB): theoretical value 703.5374, measured value 703.5354.

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Abstract

Provided herein are methods of modulating membrane potential of a cell membrane using self-assembling compounds. Also provided herein are methods of regulating a natural voltage-dependent ion channel in a cell membrane using the self-assembling compounds disclosed herein. Further provided herein are methods of treating, preventing and / or managing a disease that is related to the abnormal membrane potential responses by using the self-assembling compounds disclosed herein.

Description

field of invention [0001] Provided herein are methods of modulating the membrane potential of a cell membrane using self-assembling compounds. Also provided herein are methods of modulating native voltage-dependent ion channels in cell membranes using the self-assembling compounds disclosed herein. Further provided herein are methods of treating, preventing and / or managing diseases associated with abnormal membrane potential responses by using the self-assembling compounds disclosed herein. Background of the invention [0002] Membrane potential, the potential difference across the membrane of a living cell, is an intrinsic feature of living cells. Many important physiological processes, such as neuronal signaling, muscle contraction, cardiovascular function, and immune responses, involve changes in membrane potential. In general, the membrane potential of a cell depends inter alia on 3 factors: 1) the concentration of ions inside and outside the cell; 2) the permeability ...

Claims

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Application Information

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IPC IPC(8): A61K31/16A61K31/215A61K31/4412C07C239/14C07C239/20C07C217/48C07C217/46C07C237/42C07C225/08C07C225/14C07C225/16C07D213/63C07D213/79C07D213/81A61P9/12A61P27/00A61P13/12A61P25/14A61P25/08A61P25/00A61P19/08
CPCA61K31/166A61P9/12A61P13/12A61P19/08A61P25/00A61P25/08A61P25/14A61P27/00
Inventor 杨丹李祥沈兵姚晓强
Owner VERSITECH LTD
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