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Supramolecular surfactant constructed by cyclodextrin and hydrophobic medicine and preparation method thereof

A technology of surfactants and hydrophobic drugs, applied in drug combinations, pharmaceutical formulations, organic active ingredients, etc.

Inactive Publication Date: 2019-06-07
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the treatment of guest molecules (such as azobenzene, adamantane, ferrocene, etc.) is only reflected in the simple modification of a long alkyl chain on it as the hydrophobic end; to report

Method used

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  • Supramolecular surfactant constructed by cyclodextrin and hydrophobic medicine and preparation method thereof
  • Supramolecular surfactant constructed by cyclodextrin and hydrophobic medicine and preparation method thereof
  • Supramolecular surfactant constructed by cyclodextrin and hydrophobic medicine and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055]

[0056] Synthesis of compound 2: p-hydroxyazobenzene (1.98g, 10mmol, 1eq), 1,4-dibromobutane (7.1mL, 60mmol, 6eq) and solid potassium hydroxide (1.12g, 20mmol, 2eq) were dissolved In ethanol (150 mL), reflux under nitrogen atmosphere for 12 hours, cool to room temperature and remove the solvent under reduced pressure. The residue was resuspended in dichloromethane (100 mL), and the solid was filtered off to obtain crude compound 2, which was purified by flash preparative column chromatography (ethyl acetate:petroleum ether, 1:10 to 1:5 v / v) to obtain brown granular pure product (1.5g, 45%).

[0057] Rf=0.9 (ethyl acetate / petroleum ether, 1 / 8v / v); 1 H NMR (400MHz, CDCl 3 ,δ,ppm):7.92(d,J=8.8Hz,2H,H-4,5),7.88(d,J=7.6Hz,2H,H-6,7),7.51(t,J=7.6Hz ,2H,H-2,3),7.45(dd,J1=6.0Hz,J2=7.6Hz,1H,H-1),7.01(d,J=8.8Hz,2H,H-8,9),4.09 (t,J=6.4Hz,2H,H-10,11),3.51(t,J=6.4Hz,2H,H-16,17),2.09(m,2H,H-14,15),2.00( m,2H,H-12,13); 13 CNMR (150MHz, CDCl 3 ,δ,ppm):160.8,152.1,146.3,129.8(...

Embodiment 2

[0059]

[0060] Synthesis of Compound 3: Compound 2 (0.19g, 0.57mmol, 1eq) and thiourea (0.22g, 2.89mmol, 5eq) were dissolved in ethanol (10mL), and heated to reflux for 12 hours. After cooling down to room temperature, potassium hydroxide (0.19g, 3.47mmol) was dissolved in water (10mL), added to the above solution, heated to reflux under nitrogen atmosphere for 3 hours to room temperature, and the pH was adjusted to 1.0 with hydrochloric acid (1N). Extract with diethyl ether (30 mL×3). The combined organic phases were washed with saturated brine, dried over anhydrous sodium sulfate, ether was removed under vacuum, and purified by flash preparative column chromatography (ethyl acetate:petroleum ether, 1:5v / v) to obtain pure brown oily product (0.12g, 75%).

[0061] Rf=0.8 (ethyl acetate:petroleum ether, 1:5v / v); 1 H NMR (400MHz, CDCl 3 ,δ,ppm):7.92(d,J=8.8Hz,2H,H-4,5),7.88(d,J=7.6Hz,2H,H-6,7),7.51(t,J=7.6Hz ,2H,H-2,3),7.45(dd,J1=6.0Hz,J2=7.6Hz,1H,H-1),7.00(d,J=8.8Hz,2H,...

Embodiment 3

[0063]

[0064] Compounds 5-8 were synthesized according to previous reports.

[0065]

[0066] Synthesis of compound SN-38-azophenyl group coupler: Compound 7 (180mg, 0.27mmol, 1.5eq) was dissolved in acetic acid / ethanol mixture (1 / 20v / v, 5mL, saturated with nitrogen gas at room temperature 3 minutes), compound 3 (51mg, 0.18mmol, 1eq) was dissolved in acetic acid / ethanol mixture (1 / 20v / v, 5mL, saturated with nitrogen bubbling for 3 minutes), and slowly dropped to above solution, and reacted at room temperature for 12 hours. After removal of the solvent under reduced pressure, purification by flash preparative column chromatography (ethyl acetate: dichloromethane, 1:2 v / v) gave the pure product (55 mg, 36%) as dark yellow granules.

[0067] Rf=0.7 (ethyl acetate: dichloromethane, 1:1 v / v); 1 H NMR (400MHz, CDCl 3 ,δ,ppm):8.22(d,J=9.6Hz,1H,H-25),7.88-7.81(m,5H,H-4,5,6,7,24),7.65-7.59(m,4H ,H-18,19,26,34),7.55-7.53(m,1H,H-1),7.48-7.40(m,4H,H-2,3,20,21),6.95(d,J= 8.8Hz...

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Abstract

The invention belongs to the technical field of biology, and relates to a supramolecular surfactant constructed by cyclodextrin and hydrophobic medicine and a preparation method thereof. According tothe invention, hydrophobic medicine molecules are used as a hydrophobic end of the supramolecular surfactant, and a novel supramolecular surfactant is constructed by forming a hydrophilic end by modification of a self-sacrificing covalent bond with an azo group and inclusion by cyclodextrin. The surfactant can self-assemble into a vesicle structure in water to achieve effective hydration and loading of the hydrophobic medicine and stimulation response to light and reducing agents. The invention provides the novel strategy of construction of the supramolecular surfactant and realizes the effective loading of the hydrophobic medicine and stimulation response release.

Description

technical field [0001] The invention belongs to the field of biotechnology, and in particular relates to a supramolecular surfactant constructed from cyclodextrin and hydrophobic drugs and a preparation method thereof. Background technique [0002] As one of the most exposed chemicals in daily life, surfactants have been continuously developed along with the progress of human history. Data show that surfactants also play an irreplaceable role in cutting-edge research, including molecular machines, targeted drug delivery, and smart materials. Surfactants traditionally refer to molecules whose hydrophilic and hydrophobic ends are linked by covalent bonds. Supramolecular surfactant is a new type of surfactant that has emerged in the past ten years. Its hydrophilic and hydrophobic ends are connected by non-covalent bonds (that is, supramolecular forces), including host-guest recognition, hydrophobic and hydrophobic interactions, hydrogen bonds, π-ion interaction, metal-ligand ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K9/127A61K31/704A61K31/4745A61K31/165A61K31/4166A61P35/00
Inventor 孙涛蒋晨
Owner FUDAN UNIV
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