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Curcumin and indole pharmaceutical co-crystal with high safety and anticancer activity and preparation method of curcumin and indole pharmaceutical co-crystal

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

Active Publication Date: 2021-07-23
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 pharmaceutical co-crystal with high safety and anticancer activity and preparation method of curcumin and indole pharmaceutical co-crystal
  • Curcumin and indole pharmaceutical co-crystal with high safety and anticancer activity and preparation method of curcumin and indole pharmaceutical co-crystal
  • Curcumin and indole pharmaceutical co-crystal with high safety and anticancer activity and preparation method of curcumin and indole pharmaceutical co-crystal

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 with 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 bottom flask, use a vacuum rotary evaporation evaporator at a water bath temperature of 40 ° C, a rotation speed of 200 r / min, rotary evaporation under vacuum conditions to completely remove the solvent, and then place it in a 40 ° C vacuum oven for drying Overnight, the solvent was completely evaporated to obtain an orange-red solid powder product.

[0050] The curcumin that embodiment 1 obtains and the indole cocrystal carry out X-ray powder diffraction (PXRD) characterization, and instrument is German Bruker D8 Advance, and the PXRD collection of illustrative plates that obtains is as attached figure 1 Shown in, wherein a is the PXRD collection of illustrative plates of curcum...

Embodiment 2

[0063] Preparation of curcumin-indole drug co-crystal: accurately weigh 100 mg of curcumin and 63.6 mg of indole with 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 bottom flask, use a vacuum rotary evaporation evaporator at a water bath temperature of 40 ° C, a rotation speed of 200 r / min, rotary evaporation under vacuum conditions to completely remove the solvent, and then place it in a 40 ° C vacuum oven for drying Overnight, the solvent was completely evaporated to obtain an orange-red solid powder product.

[0064] figure 1 The PXRD spectrum shown, image 3 The characteristics of the DSC spectrum shown and Figure 4 Shown infrared spectrogram feature, illustrates that the solid product gained in the present embodiment is curcumin and indole eutectic.

[0065] Carry out solubility test to embodiment 2, the result is similar to embodim...

Embodiment 3

[0070] Preparation of curcumin-indole drug co-crystal: accurately weigh 100 mg of curcumin and 95.4 mg of indole with 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 bottom flask, use a vacuum rotary evaporation evaporator at a water bath temperature of 40 ° C, a rotation speed of 200 r / min, rotary evaporation under vacuum conditions to completely remove the solvent, and then place it in a 40 ° C vacuum oven for drying Overnight, the solvent is completely volatilized to obtain a solid powder product, which is the co-crystal of curcumin and indole medicine.

[0071] figure 1 The PXRD spectrum shown, image 3 The DSC spectrum shown, Figure 4 The infrared spectrum features shown all illustrate that the solid product obtained in the present embodiment is a cocrystal of curcumin and indole medicine.

[0072] Carry out solubility test to embodi...

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Abstract

The invention discloses a curcumin and indole pharmaceutical co-crystal with high safety and anticancer activity and a preparation method of the curcumin and indole pharmaceutical co-crystal. The preparation method comprises the following steps that curcumin and indole are uniformly mixed according to a molar ratio of 1: 1 or 1: 2 or 1: 3, then an organic solvent is added, the solvent is evaporated, and separating out the curcumin and indole pharmaceutical co-crystal is separated out; when the molar ratio of curcumin to indole is 1: 2, the obtained co-crystal is a pure curcumin and indole co-crystal; and when the compound is radiated by Cu-K alpha, an X-ray diffraction pattern represented by 2 theta has characteristic peaks at 5.70 + / -0.2 degrees, 6.22 + / -0.2 degrees, 7.08 + / -0.2 degrees, 10.18 + / -0.2 degrees, 11.36 + / -0.2 degrees, 15.18 + / -0.2 degrees and 17.34 + / -0.2 degrees. An in-vitro cytotoxicity test shows that the co-crystal has a better inhibition effect on cancer cells, so that the survival rate of the cancer cells is reduced. The obtained crystal product has higher solubility, dissolution rate, hygroscopicity and stability compared with the raw material medicine curcumin. The preparation method of the co-crystal is simple, feasible, green, environment-friendly, repeatable and high in 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, 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, and the chemical structure is shown in formula 1. Curcumin is a natural polyphenolic compound extracted from the rhizomes of herbs such as turmeric, mustard, curcuma, and turmeric. It belongs to Class IV drugs 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 vivo r...

Claims

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Application Information

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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