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Uses of 2-hydroxy-N-(4-hydroxyphenyl)-benzamide compounds in preparation of tyrosinase inhibitors

A compound and composition technology, applied in the field of medicine and food, can solve the problems of long-term safety and unsatisfactory tyrosinase inhibitory activity

Inactive Publication Date: 2016-06-22
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Although some substances have been developed as tyrosinase inhibitors or as whitening ingredients, their long-term safety and tyrosinase inhibitory activity are still unsatisfactory

Method used

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  • Uses of 2-hydroxy-N-(4-hydroxyphenyl)-benzamide compounds in preparation of tyrosinase inhibitors
  • Uses of 2-hydroxy-N-(4-hydroxyphenyl)-benzamide compounds in preparation of tyrosinase inhibitors
  • Uses of 2-hydroxy-N-(4-hydroxyphenyl)-benzamide compounds in preparation of tyrosinase inhibitors

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 14

[0098] Example 14-Hydroxy salicylanilide compound is tested for the impact on the viability of B16 cells (C57BL / 6 mouse melanoma cells)

[0099] 1.1 Experimental method

[0100] Using MTT method: B16 cells were seeded in 96-well plates, 2×10 3 Each well, 100 μL / well, set up quadruple wells, add an equal volume of culture medium (high glucose DMEM containing 10% fetal bovine serum FBS) to zero wells (no cells, only containing the same amount of medium as the experimental wells) . After 24 hours, different concentrations (3.125 μM, 6.25 μM, 12.5 μM, 25 μM, 50 μM, 100 μM) of 4-hydroxysalicylanilide (prepared in culture medium) were added, and equal concentrations of DMSO (0.1%) solution (culture medium) were added to control wells. preparation). After 48 hours of administration, discard the medium, add 100 μL MTT solution (0.5 mg / mL, prepared in DMEM), discard the supernatant after 4 hours, add 100 μL DMSO, shake for 5 minutes to completely dissolve the crystals, and measure t...

Embodiment 24

[0109] Example 2 Test of the influence of 4-hydroxy salicylanilide compound on intracellular tyrosinase activity in B16 cells

[0110] 2.1 Experimental method

[0111] B16 cells were seeded in 96-well plates, 2×10 3 Each well was cultured in high-glucose DMEM containing 10% fetal bovine serum FBS. After 24 hours, different concentrations (3.125 μM, 6.25 μM, 12.5 μM, 25 μM) of 4-hydroxysalicylanilide solution (prepared in culture medium containing 200 μM IBMX) were added. Discard the medium after 72 hours, add 100 μL of PBS solution containing 2 mM of the substrate levodopa, TritonX-1000.2%, react at 37 °C for 60 min, and measure OD with a microplate reader MultiskanMK3 492 .

[0112] 2.2 Experimental results

[0113] Table 2 Inhibitory activity to intracellular tyrosinase

[0114] compound

IC 50 (μM)

Kojic acid

>100

4-Hydroxysalicylanilide

30.34±5.30

[0115] The results are shown in Table 2 and figure 1 As shown, kojic acid did...

Embodiment 34

[0118] Example 3 Effect test of 4-hydroxy salicylanilide compound on melanin production in B16 cells

[0119] 3.1 Experimental method

[0120] B16 cells were seeded in 24-well plates, 2×10 4 cells / well, 1 mL / well, cultured with high-glucose DMEM containing 10% fetal bovine serum FBS. After 24 hours, 1 mL / well of medium containing 3-isobutyl-1-methylxanthine (IBMX, 200 μM) was added, and 4-hydroxyl Salicylanilide solution, using kojic acid as a positive control. After 72 hours of action, draw 100 μL of medium, and use a microplate reader MultiskanMK3 to measure OD 492 , measure the content of secreted melanin; discard the medium, wash twice with PBS, add 100 μL NaOH (1M) solution to each well, bathe in 70°C water for 20 minutes, draw the solution into a 96-well plate, and measure OD with a microplate reader MultiskanMK3 492 , Determination of intracellular melanin content.

[0121] 3.2 Experimental results

[0122] The result is as figure 2 , image 3 , Table 3 and Tab...

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Abstract

Uses of 2-hydroxy-N-(4-hydroxyphenyl)-benzamide compounds in preparation of tyrosinase inhibitors are disclosed. The uses include aspects of (a) preparing the tyrosinase inhibitors or compositions inhibiting tyrosinase, (b) preparing compositions inhibiting melanogenesis and (c) preparing compositions for preventing or treating pigmentary dermatoses. Test results prove that the 2-hydroxy-N-(4-hydroxyphenyl)-benzamide can inhibit activity of intracellular tyrosinase of B16 cells at the cellular level, thus effectively reducing the amount of melanin synthesized by the B16 cells, and therefore the 2-hydroxy-N-(4-hydroxyphenyl)-benzamide compounds can be used for preventing food brownness degeneration, preparing medicines treating hyperpigmentation skin diseases and preparing whitening cosmetics.

Description

technical field [0001] The invention belongs to the technical field of medicine and food, and in particular relates to the application of 4-hydroxy salicylanilide (2-Hydroxy-N-(4-hydroxyphenyl)-benzamide) compounds in the preparation of tyrosinase inhibitors and the like. Background technique [0002] Tyrosinase is a metalloenzyme combined with divalent copper ions and enzyme protein. It is the key enzyme for the synthesis of melanin in organisms and can catalyze the oxidation of phenolic compounds (such as tyrosine, dopa, etc.) into dopa Quinone forms melanin after a series of intermediate reactions, and the synthesis and distribution of melanin are directly related to the pigmentation of mammalian skin and hair, and also have an important relationship with the browning of fruits and vegetables. [0003] Therefore, by screening tyrosinase inhibitors and inhibiting the activity of tyrosinase to control the synthesis of melanin, it has become an effective method to prevent br...

Claims

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Application Information

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IPC IPC(8): C07C235/64A61K31/609A61P1/16A61P35/00A61P17/00A61K8/42A61Q19/02A61Q19/10A23L1/30A23B7/154C12N5/071C12N5/09
Inventor 王贺瑶徐志建朱敬杰张勇蔡婷婷朱维良陈凯先
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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