CN109806278A - The application of the polyethyleneglycol modified microminiature cerium oxide nanocrystal of phosphatide - Google Patents
The application of the polyethyleneglycol modified microminiature cerium oxide nanocrystal of phosphatide Download PDFInfo
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- CN109806278A CN109806278A CN201910107728.7A CN201910107728A CN109806278A CN 109806278 A CN109806278 A CN 109806278A CN 201910107728 A CN201910107728 A CN 201910107728A CN 109806278 A CN109806278 A CN 109806278A
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Abstract
The present invention relates to a kind of applications of microminiature cerium oxide nanocrystal that phosphatide is polyethyleneglycol modified, and in particular to the polyethyleneglycol modified microminiature cerium oxide nanocrystal of phosphatide is in the application being used to prepare in acute liver damage drug caused by anti-paracetamol.The polyethyleneglycol modified microminiature cerium oxide nanocrystal of phosphatide can generate a variety of anti-oxidant analogue enztme activities, can be effectively reduced excessively high survey ROS level in vivo, alleviate inflammatory reaction, play protection and therapeutic effect to acute liver damage caused by APAP.
Description
Technical field
The present invention relates to the applications of nano meter biomaterial, and in particular to a kind of microminiature that phosphatide is polyethyleneglycol modified oxidation
Cerium is nanocrystalline in the application being used to prepare in acute liver damage drug caused by anti-paracetamol.
Background technique
Drug induced hepatic injury refers to after using certain or several drugs, the liver as caused by drug itself or its metabolite
Dirty damage.Drug induced hepatic injury can behave as the acute or chronic liver diseases of any type known today, but be damaged with Acute Hepatic
Hurt most common, accounts for about 90% or more of reported cases number, the fulminant or severe liver function of life-threatening can occur for small number of patients
Failure is the emphasis of use in medicament-induced hepatotoxicity clinical monitoring and prevention and treatment.
Paracetamol is a kind of mild analgesic-antipyretic, non-toxic under therapeutic dose, but for susceptible person, or in day
When dosage is greater than 4g (adult) or 150mg/kg (children), then it can become strong Hepatoxic substance, cause the lesion of hepatic tissue cell
And damage.Toxicity key mechanism caused by paracetamol (APAP) is the APAP metabolism activation of Cytochrome P450 catalysis,
It generates active metabolite N- acetyl group -1,4-benzoquinone imines 90% (NAPQI) and causes toxicity in rodent and the mankind.
Metabolism generates excessive NAPQI formation and exhausts cellular glutathione (GSH) after APAP excess, and adduction protein includes mitochondria egg
White matter, and inducing mitochondrial oxidative stress and dysfunction.This leads to core DNA fragmentation and necrotic cell death and subsequent
Inflammatory reaction, the activation of release and immunocyte including proinflammatory cytokine.
In recent years, mitochondria is gradually considered as the main source of oxidative stress after APAP excess.Have determined APAP mistake
Excessive NAPQI formation exhausts GSH and in conjunction with the sulfydryl of cell protein after amount.Although protein adduct is not enough to cause straight
Cell death is connect, but cell protein combines, especially mitochondrial protein adduct, mitochondrial respiratory can be damaged and cause to aoxidize
Stress reaction.Also, it is known that they can interfere mitochondrial electron transport chain (ETC), leaked from chain so as to cause electronics, finally
ROS is caused to be formed.
With the fast development of nanotechnology, new hope is brought for acute liver damage caused by treatment APAP.
Summary of the invention
In view of the above-mentioned deficiencies in the prior art, it is an object of the present invention to provide a kind of microminiature oxygen that phosphatide is polyethyleneglycol modified
Change the nanocrystalline application of cerium, protection and therapeutic effect are played to acute liver damage caused by APAP.
Technical solution provided by the present invention are as follows:
A kind of microminiature cerium oxide nanocrystal that phosphatide is polyethyleneglycol modified causes being used to prepare anti-paracetamol
Acute liver damage drug in application.
The polyethyleneglycol modified microminiature cerium oxide nanocrystal of phosphatide in the present invention can generate a variety of anti-oxidant simulations
Enzymatic activity can be effectively reduced excessively high survey ROS level in vivo, alleviate inflammatory reaction, play to acute liver damage caused by APAP
Protection and therapeutic effect.Wherein, microminiature cerium oxide nanocrystal can raised ROS in statocyte, and then reduce ROS and cause
Oxidativestress damage, reach therapeutic effect；Secondly, phosphatide polyethylene glycol is nontoxic nonirritant, there is very high bio-safety
Property, the biocompatibility of microminiature cerium oxide nanocrystal can be improved.
The size of heretofore described microminiature cerium oxide nanocrystal is 0.1~10nm.Size is extra small between 0.1~10nm
Type cerium oxide nanocrystal can generate more oxygen vacancy, and making its surface, there are a large amount of trivalent cerium ion Ce3+, and it is with firefly
Stone structure makes Ce3+With tetravalence cerium ion Ce4+Mutual fast transition, generate a variety of anti-oxidant analogue enztme activities, can be effective
It is horizontal to reduce ROS excessively high in vivo, to alleviate inflammatory reaction.
The size of the polyethyleneglycol modified microminiature cerium oxide nanocrystal of heretofore described phosphatide is 10~50nm.
The preparation method of the polyethyleneglycol modified microminiature cerium oxide nanocrystal of heretofore described phosphatide includes:
1) cerous acetate and oleyl amine are added in dimethylbenzene and are reacted, precipitated through poor solvent, obtained microminiature cerium oxide and receive
Meter Jing；
2) phosphatide polyethylene glycol is dissolved in chloroform, is ultrasonically treated after microminiature cerium oxide nanocrystal is added, revolving removes
Chloroform, and good solvent aquation is added, obtain the polyethyleneglycol modified microminiature cerium oxide nanocrystal of phosphatide.
It is stirred preferably, cerous acetate and oleyl amine are added in dimethylbenzene in the step 1), by said mixture liter
Temperature keeps temperature to stir 2-6 hours to 85-95 DEG C, forms complex compound, precipitates through poor solvent, obtain microminiature cerium oxide and receive
Meter Jing.
Poor solvent is selected from anhydrous ether, ethyl alcohol, dimethyl sulfoxide, N, N- dimethyl methyl in heretofore described step 1)
One of amide and acetone are a variety of.
The mass ratio of cerous acetate and oleyl amine is 1:7~9 in heretofore described step 1).
Preferably, the time being ultrasonically treated in the step 2) is 1-30min.
Preferably, the temperature rotated in the step 2) is 45-55 DEG C, the revolving time is 1-3h.
The mass ratio of phosphatide polyethylene glycol and microminiature cerium oxide nanocrystal is 4~6:1 in heretofore described step 2).
The molecular weight ranges of phosphatide polyethylene glycol are 1000~10000 in heretofore described step 2).
In heretofore described step 2) good solvent in deionized water, phosphate buffer, cell culture medium one
Kind is a variety of.
Compared with the existing technology, the beneficial effects of the present invention are embodied in:
(1) the polyethyleneglycol modified microminiature cerium oxide nanocrystal of phosphatide in the present invention has fabulous morphosis,
Uniform particle diameter is controllable.
(2) the polyethyleneglycol modified microminiature cerium oxide nanocrystal of phosphatide in the present invention has in good scavenger-cell
The performance of ROS, and the acute liver damage of paracetamol induction can be significantly inhibited.
Detailed description of the invention
Fig. 1 is the TEM figure of the microminiature cerium oxide nanocrystal prepared in embodiment 1；
Fig. 2 is the TEM figure for the microminiature cerium oxide nanocrystal that the phosphatide for preparing is polyethyleneglycol modified in embodiment 1；
Fig. 3 is the dynamic light scattering for the microminiature cerium oxide nanocrystal that the phosphatide for preparing is polyethyleneglycol modified in embodiment 1
Particle size distribution figure；
Fig. 4 is the polyethyleneglycol modified microminiature cerium oxide nanocrystal of the different phosphatide containing concentration to normal liver cell strain
(HL7702) Sulforhodamine B colorimetric method (Sulforhodamine B, SRB) cell activity quantitative analysis knot of biocompatibility
Fruit figure；
Fig. 5 is the HL7702 that the polyethyleneglycol modified microminiature cerium oxide nanocrystal of phosphatide inhibits paracetamol induction
The SRB cell activity quantitative analysis results figure of cell death.
Specific embodiment
The invention will be further described with Figure of description combined with specific embodiments below.
Embodiment 1
(1) synthesis of microminiature cerium oxide nanocrystal:
0.4g cerous acetate hydrate and 3.2g oleyl amine are added in 15ml dimethylbenzene and stirred, with 2 centigrade per minutes
Heating rate rises to 90 degrees Celsius, stirs 4 hours formation complex compounds altogether；It is anti-that 1ml deionized water is injected into inert gas shielding
It answers in system, aging three hours, anhydrous ether precipitating, centrifugation obtains microminiature cerium oxide nanocrystal.
Morphology characterization is carried out with transmission electron microscope to microminiature cerium oxide nanocrystal, as shown in Figure 1, partial size be about 0.1~
10nm。
(2) synthesis of the polyethyleneglycol modified microminiature cerium oxide nanocrystal of phosphatide:
0.01g phosphoric acid polyethylene glycol (molecular weight 2000) and 2mg microminiature cerium oxide nanocrystal are added to 5ml chlorine
It is imitative, the ultrasound 3min in water bath sonicator pot.After 50 degrees Celsius of above-mentioned mixed liquor are rotated 2 hours, 1ml deionized water water is added
Change, obtains the polyethyleneglycol modified microminiature cerium oxide nanocrystal of phosphatide.
The microminiature cerium oxide nanocrystal polyethyleneglycol modified to phosphatide carries out morphology characterization, as shown in Fig. 2, partial size is about
10~50nm carries out particle size determination by dynamic light scattering to it, as shown in figure 3, partial size is about 10~50nm.
Embodiment 2
(1) synthesis of microminiature cerium oxide nanocrystal:
0.4g cerous acetate hydrate and 3.2g oleyl amine are added in 15ml dimethylbenzene and stirred, with 2 centigrade per minutes
Heating rate rises to 95 degrees Celsius, stirs 6 hours formation complex compounds altogether；It is anti-that 1ml deionized water is injected into inert gas shielding
It answers in system, aging three hours, anhydrous ether precipitating, centrifugation obtains microminiature cerium oxide nanocrystal.
(2) synthesis of the polyethyleneglycol modified microminiature cerium oxide nanocrystal of phosphatide:
0.01g phosphoric acid polyethylene glycol (molecular weight 2000) and 2mg microminiature cerium oxide nanocrystal are added to 5ml chlorine
It is imitative, the ultrasound 5min in water bath sonicator pot.After 50 degrees Celsius of above-mentioned mixed liquor are rotated 1.5 hours, 1ml deionized water water is added
Change, obtains the polyethyleneglycol modified microminiature cerium oxide nanocrystal of phosphatide.
Embodiment 3
(1) synthesis of microminiature cerium oxide nanocrystal:
0.4g cerous acetate hydrate and 3.2g oleyl amine are added in 15ml dimethylbenzene and stirred, with 2 centigrade per minutes
Heating rate rises to 85 degrees Celsius, stirs 3 hours formation complex compounds altogether；It is anti-that 1ml deionized water is injected into inert gas shielding
It answers in system, aging three hours, anhydrous ether precipitating, centrifugation obtains microminiature cerium oxide nanocrystal.
(2) synthesis of the polyethyleneglycol modified microminiature cerium oxide nanocrystal of phosphatide:
0.01g phosphoric acid polyethylene glycol (molecular weight 2000) and 2mg microminiature cerium oxide nanocrystal are added to 5ml chlorine
It is imitative, the ultrasound 30min in water bath sonicator pot.After 50 degrees Celsius of above-mentioned mixed liquor are rotated 2.5 hours, 1ml deionized water is added
Aquation obtains the polyethyleneglycol modified microminiature cerium oxide nanocrystal of phosphatide.
Performance test
(1) biocompatibility in vitro is evaluated
The preparation of various concentration drug: the polyethyleneglycol modified microminiature oxidation of the phosphatide for selecting embodiment 1 to be prepared
Cerium is nanocrystalline to be distributed in aqueous solution, and obtaining final microminiature cerium oxide nanocrystal concentration is 8323 μ g/ml.
Human normal hepatocyte strain (HL7702) is selected to investigate the biocompatibility in vitro of the cerium oxide of various concentration.With difference
The cell training liquid of volume disperse to obtain again concentration be respectively 0.064 μM, 0.32 μM, 1.6 μM, 8 μM, 200 μM, the drug of 1mM.
HL7702 cell activity quantitative analysis results are as shown in figure 4, cell culture fluid is only used in blank control group (con) expression
It is incubated for, concentration is microminiature cerium oxide nanocrystal of 200 μM or less the cell survival rates 90% or more, after showing modification
With good biocompatibility in vitro.
(2) inhibit hepatocyte death
The preparation of drug: the polyethyleneglycol modified microminiature cerium oxide nanocrystal of the phosphatide for selecting embodiment 1 to be prepared
It is distributed in aqueous solution, obtaining final microminiature cerium oxide nanocrystal concentration is 8323 μ g/ml.Cell model is established:
The cell culture fluid for containing paracetamol (Acetaminophen, APAP) is added in HL7702 cell, again with cell training liquid
Dispersion obtains the drug that concentration is 8mM.
Treatment group: the cell culture fluid of the cerium oxide containing 8mM is added simultaneously while addition in HL7702 cell to APAP
It is allowed to final concentration of 8 μM.
Positive controls: it is only added in HL7702 cell thin containing paracetamol (Acetaminophen, APAP)
Born of the same parents' culture solution.
Blank control group: normal cell gives fresh culture solution.
After 24 hours, cell activity is quantified with SRB, cerium oxide inhibits result such as Fig. 5 of the hepatocyte death of APAP induction
Shown, APAP has the function of significantly promoting hepatocyte death, and cell activity is only 57.9%.Give liver cell after cerium oxide
Death is inhibited, and cell activity is more than 91.7%, it was demonstrated that it has the function of inhibiting the hepatocyte death of APAP induction.
Technical solution of the present invention and beneficial effect is described in detail in embodiment described above, it should be understood that with
Upper described is only specific embodiments of the present invention, be not intended to restrict the invention, all to be done in spirit of the invention
Any modification, supplement and equivalent replacement etc., should all be included in the protection scope of the present invention.
Claims (9)
1. a kind of microminiature cerium oxide nanocrystal that phosphatide is polyethyleneglycol modified is caused by being used to prepare anti-paracetamol
Application in acute liver damage drug.
2. application according to claim 1, which is characterized in that the size of the microminiature cerium oxide nanocrystal be 0.1~
10nm。
3. application according to claim 1, which is characterized in that the polyethyleneglycol modified microminiature cerium oxide of the phosphatide is received
The size of meter Jing is 10~50nm.
4. application according to claim 1, which is characterized in that the polyethyleneglycol modified microminiature cerium oxide of the phosphatide is received
The preparation method of meter Jing includes:
1) cerous acetate and oleyl amine are added in dimethylbenzene and are reacted, precipitated through poor solvent, obtain microminiature cerium oxide nanocrystal；
2) phosphatide polyethylene glycol being dissolved in chloroform, is ultrasonically treated after microminiature cerium oxide nanocrystal is added, revolving removes chloroform,
And good solvent aquation is added, obtain the polyethyleneglycol modified microminiature cerium oxide nanocrystal of phosphatide.
5. application according to claim 4, which is characterized in that poor solvent is selected from anhydrous ether, second in the step 1)
One of alcohol, dimethyl sulfoxide, N,N-dimethylformamide and acetone are a variety of.
6. application according to claim 4, which is characterized in that the mass ratio of cerous acetate and oleyl amine is 1 in the step 1):
7~9.
7. application according to claim 4, which is characterized in that phosphatide polyethylene glycol and microminiature aoxidize in the step 2)
The nanocrystalline mass ratio of cerium is 4~6:1.
8. application according to claim 4, which is characterized in that the molecular weight ranges of phosphatide polyethylene glycol in the step 2)
It is 1000~10000.
9. application according to claim 4, which is characterized in that good solvent is selected from deionized water, phosphoric acid in the step 2)
One of salt buffer, cell culture medium are a variety of.
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| CN112516294A (en) * | 2020-12-22 | 2021-03-19 | 浙江大学 | Application of cerium oxide nano stabilizer in preparation of medicine for preventing allergic diseases and medicine composition for preventing allergic diseases |
| CN113876803A (en) * | 2021-10-14 | 2022-01-04 | 浙江大学 | ROS (reactive oxygen species) -responsive nano assembly diagnosis and treatment agent as well as preparation method and application thereof |
| CN114053300A (en) * | 2021-05-10 | 2022-02-18 | 浙江大学 | Application of cerium oxide nanoenzyme with active oxygen scavenging capacity in treating alopecia |
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