A kind of acylhydrazone molecular switch, its preparation method and application

A technology of compound and general formula, which is applied in the field of acylhydrazone molecular switch and its preparation, can solve the problems of low E-Z conversion rate, no reports of loading and controlled release, low photo-induced E-Z conversion rate, etc.

Inactive Publication Date: 2020-05-19
HUAZHONG UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this type of acylhydrazone molecular switch must be able to form intramolecular hydrogen bonds in the Z-isomer, otherwise its E-Z conversion rate is very low, and the quantum yield is also very low (J.Am.Chem.Soc.2015,137 ,14982-14991)
In addition, the photoinduced E-Z conversion rate of all acylhydrazone molecular switches in aqueous solution is very low, and there is no report on drug loading and controlled release in aqueous solution.

Method used

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  • A kind of acylhydrazone molecular switch, its preparation method and application
  • A kind of acylhydrazone molecular switch, its preparation method and application
  • A kind of acylhydrazone molecular switch, its preparation method and application

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Experimental program
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Effect test

Embodiment 1

[0058] Molecular switch I (in general formula (I), R 1 =R 2 =R 3 =-(OCH 2 CH 2 ) 5 OH; R 4 =CH 3 ; 5 = H; R 6 =-OCH 2 (CH 2 ) 12 CH 3 )Synthesis:

[0059]

[0060] A compound of formula (II) (0.2-2 g) and ethanol (10-50 mL) were added to a round bottom flask, followed by a solution of compound of formula (III) (0.3-5 g) in ethanol (10-50 mL). After heating and stirring at 40-80°C for 1-10min, filter. The collected solids were washed with ethanol to obtain the compound of formula (I) in greater than 95% yield.

[0061] Formula (I) compound in DMSO-d6 1 H-NMR spectrum see figure 2 , 13 C-NMR spectrum see image 3 , HRMS spectrum see Figure 4 .

Embodiment 2

[0063] The compound of formula I (in general formula (I), R 1 =R 2 =R 3 =-(OCH 2 CH 2 ) 5 OH; R 4 =CH 3 ; 5 = H; R 6 =-OCH 2 (CH 2 ) 12 CH 3 ) was dissolved in water, and the obtained aqueous solution was irradiated with 365nm light of a portable ultraviolet lamp to measure the 1 H-NMR spectrum, 90% of the E-isomer was converted to the Z-isomer. its in D 2 Before and after illumination in O 1 H-NMR spectrum, see Figure 5 .

Embodiment 3

[0065] Compounds of formula (I) (in general formula I, R 1 =R 2 =R 3 =-(OCH 2 CH 2 ) 5 OH; R 4 =CH 3 ; 5 = H; R 6 =-OCH 2 (CH 2 ) 12 CH 3 ) is dissolved in DMSO, with 388nm ultraviolet light for different time, measure the ultraviolet-visible spectrum of different light time, see Figure 6 (a); It is found that the absorption band at 377nm gradually weakens, while the absorption band at 273nm gradually increases, see Figure 6 (b).

[0066] Figure 6 is a compound of formula (I) (in general formula I, R 1 =R 2 =R 3 =-(OCH 2 CH 2 ) 5 OH; R 4 =CH 3 ; 5 = H; R 6 =-OCH 2 (CH 2 ) 12 CH 3 ) UV-Vis spectra in DMSO as a function of illumination time (a) and absorbance at 377nm and 273nm as a function of illumination time (b). [Formula I]=6.0×10 -5 M, light source 388nm light.

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Abstract

The invention provides a novel acylhydrazone molecular switch and synthesis thereof and a method for photoinduced slow release of a drug. The molecular switch is formed by condensation of 2-methoxynaphthaldehyde and benzoyl hydrazine. As both sides adjacent to an imine group of hydrazide have groups with high steric hindrance, an E-isomer is easily converted into a Z-isomer under illumination, andthe E-Z isomer conversion efficiency is up to 99 percent, and the quantum yield is up to 89 percent. After being prepared in an amphiphilic molecular switch, the hydrazide can be self-assembled in water to form nano-vesicles, and the vesicles can also undergo E-Z isomer conversion with high conversion rate under the illumination. The vesicles can carry an anticancer drug procarbazine in an inclusion manner, so that the solubility of the drug in water is increased by 225 times. The included procarbazine is released from the vesicles under the illumination.

Description

technical field [0001] The invention belongs to the field of chemistry, and more specifically relates to an acylhydrazone molecular switch, its preparation method and application. Background technique [0002] Photoinduced molecular switches have great potential applications in information storage, photoactivators, photopharmacology, remote control of reactions, photocontrolled electronic devices, controllable drug delivery and release, etc., and have attracted extensive attention and research. The 2016 Nobel Prize in Chemistry The prize goes to scientists who study molecular machines, including molecular switches. However, common photoinduced molecular switches, such as molecular switches based on derivatives of azobenzene, diaromatic ethylene, and spiropyran, have good photoswitching properties, but their synthesis is very difficult (Chem.Soc.Rev. 2012, 41, 1809-1825; Chem. Soc. Rev. 2013, 43, 148-184; Chem. Rev. 2014, 114, 12174-12277). [0003] The recently appeared ac...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C249/16C07C251/86A61K9/127A61K47/10A61K31/166C08G65/331A61P35/00C07B35/08
CPCA61K9/1273A61K31/166A61K47/34A61P35/00C07C251/86
Inventor 郑炎松袁迎雪
Owner HUAZHONG UNIV OF SCI & TECH
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