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Curcumin and indole drug co-crystal with high safety and anticancer activity and preparation method thereof

An anti-cancer activity, indole co-crystal technology, applied in drug combinations, anti-tumor drugs, organic chemical methods, etc., can solve the problems of thermodynamic instability, prone to agglomeration, poor stability, etc. The effect of transformation and environmental pollution is small

Active Publication Date: 2022-05-24
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

(2) As a crystalline drug, due to its known structure and stable properties, it can stabilize the structure of curcumin and improve its poor stability in the process of making medicine and storage. Other drug dosage forms often cannot do it, but it is easy to agglomerate. Phenomena such as light instability
Selected polyphenolic co-crystal formers, explored the method of using kinetics, and successfully used the rapid nucleation of the rotary evaporation method to prepare potential thermodynamically unstable drug co-crystals that were difficult to find by traditional methods, and the obtained crystals showed better performance than raw materials. The drug has better dissolution rate, moisture absorption stability and tablet performance, which proves the feasibility of fast solvent volatilization nucleation method to prepare drug co-crystals, but the selected co-crystal formers are not non-toxic and low-toxic drugs according to GRAS standards

Method used

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  • Curcumin and indole drug co-crystal with high safety and anticancer activity and preparation method thereof
  • Curcumin and indole drug co-crystal with high safety and anticancer activity and preparation method thereof
  • Curcumin and indole drug co-crystal with high safety and anticancer activity and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Preparation of curcumin-indole drug co-crystal: Accurately weigh 100 mg of curcumin and 31.8 mg of indole in a molar ratio of 1:1 with an electronic balance, mix well with a vortex mixer, add 30 mL of acetone, and ultrasonically dissolve the drug completely And mix evenly, transfer to a round-bottomed flask, use a vacuum rotary evaporator at a water bath temperature of 40 °C, a rotation speed of 200 r / min, and rotary evaporation under vacuum conditions to completely remove the solvent, and then place it in a 40 °C vacuum drying oven to dry. Over night, the solvent was completely evaporated to obtain an orange-red solid powder product.

[0050] The curcumin and indole co-crystals obtained in Example 1 were characterized by powder X-ray diffraction (PXRD), and the instrument was Bruker D8 Advance from Germany, and the obtained PXRD pattern was as attached. figure 1 As shown in, wherein a is the PXRD pattern of the curcumin bulk drug, b is the PXRD pattern of the indole bu...

Embodiment 2

[0063] Preparation of curcumin-indole drug co-crystal: Accurately weigh 100 mg of curcumin and 63.6 mg of indole in a molar ratio of 1:2 with an electronic balance, mix well with a vortex mixer, add 30 mL of acetone, and ultrasonically dissolve the drug completely And mix evenly, transfer to a round-bottomed flask, use a vacuum rotary evaporator at a water bath temperature of 40 °C, a rotation speed of 200 r / min, and rotary evaporation under vacuum conditions to completely remove the solvent, and then place it in a 40 °C vacuum drying oven to dry. Over night, the solvent was completely evaporated to obtain an orange-red solid powder product.

[0064] figure 1 The PXRD spectrum shown, image 3 The DSC spectral characteristics shown and Figure 4 The characteristics of the infrared spectrum shown indicate that the solid product obtained in this example is a co-crystal of curcumin and indole.

[0065] The solubility test of Example 2 was carried out, and the result was similar...

Embodiment 3

[0070] Preparation of curcumin-indole drug co-crystal: Accurately weigh 100 mg of curcumin and 95.4 mg of indole in a molar ratio of 1:3 with an electronic balance, mix well with a vortex mixer, add 30 mL of acetone, and ultrasonically dissolve the drug completely And mix evenly, transfer to a round-bottomed flask, use a vacuum rotary evaporator at a water bath temperature of 40 °C, a rotation speed of 200 r / min, and rotary evaporation under vacuum conditions to completely remove the solvent, and then place it in a 40 °C vacuum drying oven to dry. Overnight, the solvent was completely volatilized to obtain a solid powder product, namely the co-crystal of curcumin and indole drug.

[0071] figure 1 The PXRD spectrum shown, image 3 The DSC spectrum shown, Figure 4 The infrared spectrum characteristics shown all illustrate that the solid product obtained in this example is a co-crystal of curcumin and indole drug.

[0072] The solubility test of Example 3 was carried out, an...

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Abstract

The invention discloses curcumin and indole drug co-crystal with high safety and anticancer activity and a preparation method thereof; the molar ratio of curcumin and indole is 1:1 or 1:2 or 1:3, and then added Organic solvent, after the solvent evaporates, the curcumin and indole drug co-crystals are precipitated; when the molar ratio of curcumin and indole is 1:2, the resulting co-crystals are pure curcumin and indole co-crystals; with Cu-Kα radiation, it is The X-ray diffraction spectrum represented by 2θ has characteristic peaks at 5.70±0.2°, 6.22±0.2°, 7.08±0.2°, 10.18±0.2°, 11.36±0.2°, 15.18±0.2°, 17.34±0.2°; Toxicity tests show that the co-crystal has a better inhibitory effect on cancer cells and reduces the survival rate of cancer cells. The crystal product obtained in the present invention has better solubility, dissolution rate, hygroscopicity and stability than the crude drug curcumin. The preparation method of the co-crystal is simple, feasible, environmentally friendly, repeatable and has a high yield.

Description

technical field [0001] The invention relates to curcumin medicine, in particular to a co-crystal of curcumin and indole medicine and a preparation method thereof, belonging to the technical field of medicinal chemistry. Background technique [0002] Curcumin (Curcumin, CUR), 1,7-bis(4-hydroxy-3-methoxybenzyl)-1,6-heptadiene-3,5-dione, also known as curcumin, acid yellow, The molecular formula is C 21 H 20 O 6 , the molecular weight is 368.38, the melting point is about 183 ° C, the powder is orange-yellow, insoluble in water, easily soluble in acetone, ethanol, methanol and other organic solvents, the chemical structural formula is as formula 1. Curcumin is a natural polyphenolic compound extracted from the rhizomes of herbs such as turmeric, mustard, curcuma, curcuma, etc. It belongs to the Class IV drug of the Biopharmaceutical Classification System (BCS) and has the characteristics of low solubility and low permeability. Over the centuries, a wealth of in vitro and in...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/08C07C49/255C07C45/81A61P35/00
CPCC07D209/08C07C49/255A61P35/00C07B2200/13
Inventor 江燕斌吴艳婷宋阳刘诗苑赵望
Owner SOUTH CHINA UNIV OF TECH