CN115501336B - Water-soluble curcumin compound with antibacterial capability and preparation method and application thereof - Google Patents

Water-soluble curcumin compound with antibacterial capability and preparation method and application thereof Download PDF

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CN115501336B
CN115501336B CN202211056451.8A CN202211056451A CN115501336B CN 115501336 B CN115501336 B CN 115501336B CN 202211056451 A CN202211056451 A CN 202211056451A CN 115501336 B CN115501336 B CN 115501336B
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CN115501336A (en
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李培源
吕应斌
鄢宏俊
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Guangxi University of Chinese Medicine
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61K41/00—Medicinal preparations obtained by treating materials with wave energy or particle radiation ; Therapies using these preparations
    • A61K41/0057—Photodynamic therapy with a photosensitizer, i.e. agent able to produce reactive oxygen species upon exposure to light or radiation, e.g. UV or visible light; photocleavage of nucleic acids with an agent
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61K31/00—Medicinal preparations containing organic active ingredients
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Abstract

The invention discloses a preparation method of a water-soluble curcumin compound with antibacterial capability, which comprises the following steps: step one, preparing carbon dots: citric acid is used as a carbon source, thiourea is used as a nitrogen source and a sulfur source, and a carbon point is prepared by a one-step hydrothermal method; step two, preparing a curcumin compound: stirring the carbon dots, EDC, NHS and dimethyl sulfoxide prepared in the first step for a period of time, standing for a period of time, adding cholesterol dissolved in the dimethyl sulfoxide, continuously stirring for a period of time, then adding a curcumin solution, continuously stirring for a period of time, dialyzing, taking the solution in a dialysis bag, and freeze-drying to obtain the curcumin compound. The invention has the advantages of simple preparation method, good water solubility of the prepared curcumin compound and strong sterilization capability. The invention discloses an application of curcumin compound in antibiosis.

Description

Water-soluble curcumin compound with antibacterial capability and preparation method and application thereof
Technical Field
The invention relates to the field of ginger traditional Chinese medicine nano materials. More particularly, the invention relates to a water-soluble curcumin compound with antibacterial capability, and a preparation method and application thereof.
Background
In recent years, bacterial infections, particularly those occurring after antibiotic treatment, have become a major problem worldwide because of the increasing resistance of microorganisms to antibiotics and other antibacterial agents. Thus, new bactericidal strategies that do not require antibiotics should be developed and employed to treat infections caused by pathogenic microorganisms. Researchers are increasingly interested in the role of curcumin as a natural substitute for chemical drugs in the treatment of several diseases. In fact, curcumin has been reported to have a variety of pharmacological activities including antimalarial, antibacterial, antiviral, antifungal, antioxidant, anti-inflammatory, antidiabetic, anti-human immunodeficiency virus and anticancer activities. Unfortunately, their use is limited due to their hydrophobicity, low bioavailability, chemical instability, photodegradation and fast metabolism.
The carbon dots are novel nano carbon materials with extremely small size (below 10 nm) and fluorescent property, which are formed by dispersed spherical-like carbon material particles. The carbon dots have a series of excellent performances such as wide sources of raw materials, easiness in preparation, good optical properties, extremely small size, excellent water solubility, stable chemical properties, lower cytotoxicity, good biocompatibility, low cost, environmental friendliness, stronger quantum confinement effect, stable fluorescence performance and the like. The method has good potential application prospects in various fields such as biological imaging, chemical analysis, energy development, drug delivery, organic matter analysis, photocatalysis and the like, and has great research value.
Disclosure of Invention
It is an object of the present invention to solve at least the above problems and to provide at least the advantages to be described later.
To achieve these objects and other advantages and in accordance with the purpose of the invention, there is provided a method for preparing a water-soluble curcumin complex having antibacterial ability, comprising the steps of:
step one, preparing carbon dots: citric acid is used as a carbon source, thiourea is used as a nitrogen source and a sulfur source, and a carbon point is prepared by a one-step hydrothermal method;
step two, preparing a curcumin compound: stirring the carbon dots, EDC, NHS and dimethyl sulfoxide prepared in the first step for a period of time, standing for a period of time, adding cholesterol dissolved in the dimethyl sulfoxide, continuously stirring for a period of time, then adding a curcumin solution, continuously stirring for a period of time, dialyzing, taking the solution in a dialysis bag, and freeze-drying to obtain the curcumin compound.
Preferably, the molar ratio of citric acid to thiourea in the first step is 1-2:3.
Preferably, pure water of water in the one-step hydrothermal process in the step one is used.
Preferably, the reaction temperature in the one-step hydrothermal method in the first step is 160-180 ℃ and the reaction time is 4-6 h.
Preferably, the reaction solution obtained after the reaction in the first step is subjected to centrifugal filtration to remove substances with larger particles, then a dialysis bag is adopted for dialysis for a period of time, the substances with larger particles are removed from the solution in the dialysis bag through centrifugal filtration again, and the obtained solution in the dialysis bag is carbon dot solution, and the carbon dot is obtained through freeze drying.
Preferably, the dialysis bags in step one have a molecular weight cut-off of 500-1000 Da.
Preferably, in the second step, the mass ratio of the carbon dots, EDC and NHS is 10:10:14.9.
Preferably, the standing time in the second step is more than 60min, the stirring time is 24h, the dialysis time is 48h, and the dialysate is replaced every 6h.
A curcumin compound prepared by the preparation method is provided.
Provides an application of the curcumin complex in antibiosis.
The invention at least comprises the following beneficial effects: firstly, carbon dots with nitrogen and sulfur elements and cholesterol are combined with curcumin to obtain the composite medicine with good water solubility, so that the bioavailability of the curcumin is improved. Secondly, cholesterol can significantly promote hydrophobic binding of curcumin to bacterial surfaces, enabling bacterial cell surface engineering based on hydrophobic interactions. In addition, the compound synthesized by the method has a unique sea urchin-shaped nano cluster crystal structure and wraps more curcumin and carbon points. The compound has targeting photodynamic ability and can provide good antibacterial effect.
Additional advantages, objects, and features of the invention will be set forth in part in the description which follows and in part will become apparent to those having ordinary skill in the art upon examination of the following or may be learned from practice of the invention.
Drawings
FIG. 1 is an electron microscopic view of a curcumin complex prepared in example 1 of the present invention;
FIG. 2 is an electron microscopic image of the cholesterol-free curcumin complex prepared in comparative example 1 of the present invention;
FIG. 3 is a graph showing antibacterial data of the products prepared in example 1 and comparative example 1, which are carbon dots according to the present invention;
fig. 4 is a diagram of a bacteriostatic electron microscope according to example 1 of the present invention.
Detailed Description
The present invention is described in further detail below with reference to the drawings to enable those skilled in the art to practice the invention by referring to the description.
The experimental methods described in the following embodiments are conventional methods unless otherwise indicated, and the reagents and materials are commercially available.
Example 1 ]
1. Preparation of carbon dots:
citric acid is used as a carbon source, thiourea is used as a nitrogen source and a sulfur source, and the carbon dots are prepared by a one-step hydrothermal method. The method comprises the following steps: 1.15g of citric acid and 1.56g of thiourea are taken and dissolved in 20mL of pure water, the mixture is stirred for 10min at 25 ℃ under 40KHz ultrasonic, and then the mixture is added into a tetrafluoroethylene reaction kettle for reaction for 4h at 160 ℃. After cooling to room temperature, the reaction solution was centrifuged at 10000r/min for 10min, the large particulate matters in the solution were removed by filtration, and then dialyzed with a dialysis bag (mwco=500 to 1000 Da) for 24h. Centrifuging the inner liquid of the dialysis bag for 10min at a rotating speed of 10000r/min again, filtering to remove large granular substances in the solution, obtaining the inner liquid of the dialysis bag, namely the carbon dot solution, and then freeze-drying to obtain the carbon dot solid.
2. Preparation of the composite:
10mg of carbon dots, 10mg of EDC (1-ethyl- (3-dimethylaminopropyl) carbodiimide), 14.9mg of NHS (N-hydroxysuccinimide) were taken, 10mL of dimethyl sulfoxide was added thereto, and the mixture was stirred for 30 minutes and allowed to stand at room temperature for 60 minutes. Then, 10mg of cholesterol was dissolved in 1mL of dimethyl sulfoxide, and the mixture was mixed with the above-mentioned solution after standing, followed by stirring for 24 hours. Then adding 1mL of curcumin solution (1 mg/mL), stirring for 24h, dialyzing for 48h by using a dialysis bag, replacing the dialyzate every 6h, and freeze-drying the dialyzate to obtain the curcumin compound.
Comparative example 1 ]
10mg of carbon dots, 10mg of EDC (1-ethyl- (3-dimethylaminopropyl) carbodiimide), 14.9mg of NHS (N-hydroxysuccinimide) were taken, 10mL of dimethyl sulfoxide was added thereto, and the mixture was stirred for 30 minutes and allowed to stand at room temperature for 60 minutes. Then adding 1mL of curcumin solution (1 mg/mL), stirring for 24h, dialyzing for 48h by using a dialysis bag, replacing the dialyzate every 6h, and freeze-drying the dialyzate to obtain the curcumin compound without cholesterol.
< Performance detection >
1. Water solubility detection
The curcumin, the samples prepared in the example 1 and the comparative example 1 are dissolved in water, and the samples in the example 1 are imaged by a transmission electron microscope, so that the samples are similar to nano-cluster crystals of sea urchins in shape, have good dispersibility and are not stacked and adhered. Through the magnification, a plurality of carbon points are uniformly distributed in the crystal, the carbon points are similar in size and spherical, and the shape of the carbon points is consistent with the shape of common carbon points. Indicating that the complex was successfully synthesized and had a significant drug loading (shown in figure 1).
The sample prepared in comparative example 1 only has a spherical shape, and has small drug loading and uneven dispersion. (shown in FIG. 2)
2. Antibacterial property detection
Gram negative bacteria such as E.coli (E.coli) were selected as representatives. A 405nm light source is selected as a photodynamic antibacterial light source. Samples prepared in example 1 and comparative example 1 were diluted with 0.9wt% physiological saline to different concentrations, and 10. Mu.L of each of the bacterial suspensions in the logarithmic phase was mixed with 90. Mu.L of each of the sample solutions of different concentrations, and the final administration concentrations were 0.05. Mu.g/mL, 0.1. Mu.g/mL, 0.25. Mu.g/mL, 0.5. Mu.g/mL, 1. Mu.g/mL, 2.5. Mu.g/mL, 5. Mu.g/mL, and 10. Mu.g/mL. The light source was set at 405nm (20 mW/cm 2 ) The bacteria were treated with light source irradiation for 10min. The treated bacterial suspension was diluted with 0.9wt% physiological saline, and 30. Mu.L of the suspension was plated on LB nutrient agar plates, and after culturing for 24 hours, plate colony counts were performed.
The bacteria after the administration of light were photographed by a scanning electron microscope, and it was found that the bacteria of example 1 and comparative example 1 became incomplete in surface and many wrinkles occurred, indicating that the samples of example 1 and comparative example 1 had antibacterial properties.
All experiments were performed in triplicate. The results show that the sample of example 1 has very good inactivation to E.coli and is much stronger than free curcumin and also much stronger than the sample of comparative example 1 (as shown in FIGS. 3, 4).
The English release in FIG. 3 is as follows: coli survivin rate: gram negative E.coli survival rate, cur-Light: carbon dot, CDs/Cur-Light: cholesterol-free curcumin complex prepared in comparative example 1, chol-CDs/Cur-Light: concentration of curcumin Complex prepared in example 1
Although embodiments of the present invention have been disclosed above, it is not limited to the details and embodiments shown and described, it is well suited to various fields of use for which the invention would be readily apparent to those skilled in the art, and accordingly, the invention is not limited to the specific details and illustrations shown and described herein, without departing from the general concepts defined in the claims and their equivalents.

Claims (10)

1. The preparation method of the water-soluble curcumin compound with antibacterial capability is characterized by comprising the following steps of:
step one, preparing carbon dots: citric acid is used as a carbon source, thiourea is used as a nitrogen source and a sulfur source, and a carbon point is prepared by a one-step hydrothermal method;
step two, preparing a curcumin compound: stirring the carbon dots, EDC, NHS and dimethyl sulfoxide prepared in the first step for a period of time, standing for a period of time, adding cholesterol dissolved in the dimethyl sulfoxide, continuously stirring for a period of time, then adding a curcumin solution, continuously stirring for a period of time, dialyzing, taking the solution in a dialysis bag, and freeze-drying to obtain the curcumin compound.
2. The method for preparing a water-soluble curcumin complex with antibacterial ability according to claim 1, wherein the molar ratio of citric acid to thiourea in the first step is 1-2:3.
3. The method for preparing a water-soluble curcumin complex having antibacterial ability according to claim 1, wherein water in the one-step hydrothermal method in the step one is pure water.
4. The method for preparing a water-soluble curcumin complex with antibacterial ability according to claim 1, wherein the reaction temperature in the one-step hydrothermal method in the step one is 160-180 ℃ and the reaction time is 4-6 h.
5. The method for preparing a water-soluble curcumin complex with antibacterial ability according to claim 1, wherein the reaction solution obtained in the first step is centrifuged to remove substances with larger particles, then dialyzed for a period of time by a dialysis bag, and the substances with larger particles are removed by centrifugation again from the solution in the dialysis bag, and the obtained solution in the dialysis bag is a carbon dot solution, and freeze-dried to obtain carbon dots.
6. The method of claim 5, wherein the dialysis bags in step one have a molecular weight cut-off of 500-1000 Da.
7. The method for preparing the water-soluble curcumin complex with antibacterial capability according to claim 1, wherein the mass ratio of carbon dots, EDC and NHS in the second step is 10:10:14.9.
8. The method for preparing a water-soluble curcumin complex with antibacterial ability according to claim 1, wherein the standing time in the second step is more than 60min, the stirring time is 24h, the dialysis time is 48h, and the dialysate is replaced every 6h.
9. Curcumin complex prepared by the preparation method as claimed in any one of claims 1 to 8.
10. Use of the curcumin complex as claimed in claim 9 for the preparation of an antibacterial agent.
CN202211056451.8A 2022-08-31 2022-08-31 Water-soluble curcumin compound with antibacterial capability and preparation method and application thereof Active CN115501336B (en)

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104192827A (en) * 2014-08-26 2014-12-10 上海交通大学 Method for synthesizing carbon quantum dots on basis of organic micromolecule microwave solid-phase reaction
WO2019232701A1 (en) * 2018-06-06 2019-12-12 Huang Chih Ching Curcumin carbon quantum dots and use thereof
CN114106823A (en) * 2021-12-10 2022-03-01 福建医科大学 Preparation method and broad-spectrum antibacterial application of quaternary ammonium salt curcumin carbon quantum dots

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104192827A (en) * 2014-08-26 2014-12-10 上海交通大学 Method for synthesizing carbon quantum dots on basis of organic micromolecule microwave solid-phase reaction
WO2019232701A1 (en) * 2018-06-06 2019-12-12 Huang Chih Ching Curcumin carbon quantum dots and use thereof
CN114106823A (en) * 2021-12-10 2022-03-01 福建医科大学 Preparation method and broad-spectrum antibacterial application of quaternary ammonium salt curcumin carbon quantum dots

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