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Wound exudate responsive controlled released hydrogen sulfide probe and preparation method and application thereof

A technology of exudate and hydrogen sulfide, applied in the field of medical materials, can solve problems such as toxic by-products, achieve rapid and efficient release, good repair effect, fast and efficient real-time self-monitoring effect

Active Publication Date: 2021-09-17
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, it is difficult for existing materials to realize real-time self-monitoring of hydrogen sulfide release, and the release process may produce toxic by-products

Method used

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  • Wound exudate responsive controlled released hydrogen sulfide probe and preparation method and application thereof
  • Wound exudate responsive controlled released hydrogen sulfide probe and preparation method and application thereof
  • Wound exudate responsive controlled released hydrogen sulfide probe and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0048] Preparation of Precursor Compound III-2:

[0049] 5-(4-(Diphenylamine)phenyl)thiophene-2-carbaldehyde (354 mg, 1.0 mmol), 2-(3-cyano-4,5,5-trimethylfuran-2(5H)-ylidene Methyl)malononitrile (301mg, 1.5mmol) was placed in a mixed solvent of ethanol / tetrahydrofuran (6:4 by volume), and stirred under reflux for 5h under a nitrogen atmosphere. After the reaction was completed, purification was carried out by silica gel column chromatography to obtain III-2 with a yield of ~59%. 1 H NMR (CDCl 3 , 400MHz): δ7.81(d, J=16.0Hz, 1H), 8.20(dt, J 1 =8.8Hz,J 2 = 4.4Hz,J 3 =2.4Hz, 2H), 7.44(d, J=4.4Hz, 1H), 7.34(d, J=1.6Hz, 1H), 7.33-7.28(m, 4H), 7.19-7.09(m, 6H), 7.06 (d, J=8.8Hz, 2H), 6.62(d, J=15.6Hz, 1H), 1.76(s, 6H); 13 C NMR (CDCl 3 ,101MHz):δ175.65,173.06,153.94,149.56,146.67,139.61,137.89,137.47,129.57,127.19,125.48,124.26,124.06,121.89,112.08,112.00,111.30,110.87,104.97,97.05,96.71,77.33, 77.22, 77.01, 76.69, 29.70, 26.54. ESI-HRMS: m / z [M+H + ] Theory C 34 h 25 N ...

Embodiment 1

[0052] Preparation of probe I-2:

[0053] Weigh 10mg of precursor compound III-2, dissolve it with DMSO and configure it into a 10.5mmol / L solution; weigh 5mgNa 2 S, dissolved in ultrapure water and made into a 100mmol / L solution; take 950μL of the 10.5mmol / L solution of III-2, add 50μL Na 2 100mmol / L solution of S and mix well to obtain probe I-2.

[0054] The structure of I-2 is:

[0055]

Embodiment 2

[0057] Preparation of probe II-2:

[0058] Weigh 10mg of precursor compound III-2, dissolve it in DMSO and make it into a 10.5mmol / L solution; weigh 5mg of NaHS, dissolve it in ultrapure water and make it into a 200mmol / L solution; take III-2’s 10.5mmol / L Solution 950μL, add 50μL NaHS 200mmol / L solution and mix well to obtain probe II-2.

[0059] The structure of II-2 is:

[0060]

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Abstract

The invention belongs to the technical field of medical materials, and discloses a wound exudate responsive controlled released hydrogen sulfide probe and a preparation method and application thereof. The wound exudate responsive controlled released hydrogen sulfide probe is more than one of a formula I or a formula II; R in the formula I and R in the formula II are respectively phenylene, thienyl, furylidene, pyrrolidene and phosphoropentadiene without two hydrogen atoms; R1 and R2 are independent hydrogen, C1-6 alkyl groups, C1-6 alkyloxy groups and C1-6 alkyl sulfenyl groups. The method comprises the following steps: 1) dissolving a precursor compound in an organic solvent to obtain a precursor compound solution; preparing a compound containing S < 2-> or HS <-> into a solution to obtain a sulfur-containing solution; and 2) mixing the precursor compound solution with a sulfur-containing solution to obtain the probe. The probe provided by the invention can realize quick and efficient release of hydrogen sulfide in response to wound exudate or water and real-time self-monitoring; the wound repair can be promoted, and the repair effect is good.

Description

technical field [0001] The invention belongs to the technical field of medical materials, and in particular relates to a wound exudate-responsive controlled-release hydrogen sulfide probe, a preparation method and application thereof. Background technique [0002] The skin is in direct contact with the external environment. It is the largest organ of the human body, and also the largest and most active immune organ. It is the first defense barrier of the human body. The skin protects the various tissues within from pathogens, mechanical damage, and temperature extremes. In addition, the skin plays a vital role in thermoregulation, sensory perception, vitamin D synthesis, and protection from external insults, including UV rays, trauma, and microorganisms. As the outermost layer of the human body, skin is highly susceptible to various types of injuries such as trauma, cuts, burns, chemical injuries, ulcers and cancer, which have a major impact on patients and healthcare econo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/68C09K11/06A61K31/381A61P17/02
CPCC07D307/68C09K11/06A61K31/381A61P17/02C09K2211/1088
Inventor 高蒙李有镇朱文超
Owner SOUTH CHINA UNIV OF TECH
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