CN101036653A - Application of compound 6-furfuryl aminopurine in the preparing of medicine for preventing hepatic injury - Google Patents
Application of compound 6-furfuryl aminopurine in the preparing of medicine for preventing hepatic injury Download PDFInfo
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Abstract
The invention discloses a use of compounds of 6-furfuryl-aminopurine for preparing drugs for preventing liver injury. It is proved by experiment that the compounds of 6-furfuryl-aminopurine can improve anti-oxidative damage capacity of the liver in the body and have a certain protecting action from aging of the body and liver diseases such as hepatonecrosis, hepatocirrhosis, etc. Accordingly, the compounds of 6-furfuryl-aminopurine, as exogenous purine compounds, have function like zoohormone or phytohormone, can help mice resisting extraneous oxidative damage, promote antioxidase synthesis and directly catch and remove free radical, so that oxygen free radical reaction and lipid peroxidation reaction are prevented or suppressed and cell membrane integrity is maintained.
Description
Technical field
(be commonly called as kinetins, a kind of new purposes Kinetin) refers to that specifically compound known 6-furfuryl group amidopurin is used to prepare the purposes of anti-liver injury medicament to the present invention relates to 6-furfuryl group amidopurin.
Background technology
Liver is the substantive body of gland organ maximum in the human body, that function is maximum, is called " chemical plant of human body maximum ", and it participates in processes such as digestion in the body, metabolism, drainage, detoxifcation and immunity, is the organ with important and complicated metabolic function.It has Hepatic artery and the dual blood supply of portal vein, and there are hepatic vein and biliary system to go out liver, add abundant blood sinus and exquisite lobules of liver structure, and be rich in mitochondrion, endoplasmic reticulum, ribosome and a large amount of enzyme in the hepatocyte, thereby can finish complicated and diversified metabolic function.But, natural or synthetic chemical substance transform owing to mainly entering liver by gastrointestinal tract portal vein or body circulation, therefore the easier toxicant infringement that is subjected in the chemicals of liver is caused by chemical substance at about 25% acute hepatic failure of American-European countries (ALF).
Excessive formation active oxygen product is the major reason of hepatocyte injury in the liver.N,N'-dimethyl-.gamma..gamma.'-dipyridylium chemical compounds such as (herbicide) can stimulate oxygen-derived free radicals to form when P-450 handles, and the latter also can be produced by activated Kupffer Cell and polymorphonuclear leukocyte (PMNs).Oxygen-derived free radicals is mainly derived from xanthine oxidase system and mitochondrion, xanthine oxidase is present in the body with the xanthine dehydrogenase form usually, its catalytic reaction does not form free radical. but when ATP exhaustion or oxidative stress, xanthine dehydrogenase is converted into xanthine oxidase. and the xanthine oxidase that catalysis ATP metabolism produces changes into uric acid and generates O
2 -With
1O
2, O
2 -Reactive poor in aqueous medium. disperse is fast, and very fast dismutation by enzyme is converted into O
2, generate OH through reduction reaction
-Mitochondrial respiratory chain under normal circumstances can produce a small amount of oxygen-derived free radicals, causes a large amount of oxygen-derived free radicals when mitochondrial function is impaired and generates.
Oxygen-derived free radicals is the main cause that causes animal body aging and disease.Oxygen is element the abundantest on the earth, and atomic density is 53.8%.Oxygen in the earth atmosphere itself is exactly free radical, is again the main booster of radical reaction in the living cells, when oxygen slightly exceeds normal concentration aerobe is poisoned.The toxicity of oxygen is not because the respond of oxygen molecule itself, but, comprise superoxide anion, hydrogen peroxide molecule, hydroxy radical, hydroperoxy, hydroperoxides, alkoxyl, alkane peroxy and singlet oxygen etc. because oxygen molecule is reduced into the many intermediate products that produce in the water process.These intermediate products comprise free radical and molecule, are referred to as active oxygen, but custom calls free radical to them.Free radical is meant that those have the atom of unpaired electronics, molecule or ion, and they have the tendency that obtains or lose electronics.Therefore, the character of free radical is active especially, has very high reactivity, and very easily reacting with other material generates new free radical or oxide.In organic vital movement process, the generation of free radical, cancellation, utilization and damaging action are the unity of opposites processes of almost carrying out simultaneously.Under normal circumstances, the generation and the removing of oxygen-derived free radicals are in dynamic equilibrium in the body, have the complete system of defense of a cover to protect body not to be subjected to damage of radicals in the animal body.Therefore under physiological condition, concentration of oxygen free radicals is in normal condition, not only can damaged tissue, but also demonstrate its unique physiological action, effects such as for example detoxifcation of the microorganism of phagocyte kill harmful, synthesis of prostaglandins and thrombinogen, medicine and poisonous substance, the cell of eliminating sudden change and immunomodulating.But under the situation of morbid state and aging, body can not effectively be removed the oxygen-derived free radicals of generation, can cause that the concentration of oxygen free radicals rising causes tissue injury and disease takes place in the body.From the molecular biology angle, oxygen-derived free radicals is mainly shown off toxic action by biomolecule such as lipid peroxidation, injury protein matter and nucleic acid.
Therefore, the liver oxidative damage is the very common and serious damage that animal and human's body is faced, and can cause the aging of animal and human's body and the generation of other diseases, increases the weight of the aging and the pathological changes of body.At present, the material of many anti-liver oxidative damages is arranged on the market, but great majority have all the extraction of being difficult for to obtain, purity is not high, and effective ingredient is indeterminate, and shortcomings such as price height have been brought very big trouble to application.It is wide to develop a kind of source, the purity height, and definite ingredients, effective, very urgent of the material of the anti-liver oxidative damage that safety non-toxic is harmless and being significant.
6-furfuryl group amidopurin is 1956, and MLiller has found a kind of active micromolecular compound of the cell division of promotion that has in the herring sperm dna extract that heat sterilization is crossed.It is a kind of non-natural basic element of cell division, be commonly called as kinetins (kinetin, KT), molecular formula C
10H
9N
5O.Pure product are white solid, and fusing point is 265～266 ℃, are amphoteric compound.Be soluble in dilute hydrochloric acid or dilute alkaline soln; Be insoluble in water, ethanol, ether and acetone.Its structural formula is:
6-furfuryl group amidopurin is that first is found in the material that has basic element of cell division effect on the plant.It also has the organ senescence of delaying except that having the effect that promotes cell division, differentiation and growth, the induced bud differentiation, increase stomatal aperture, callus induction sprouts, and removes apical dominance, break the lateral bud dormancy and promote germination, delay the effect of protein and chlorophyllous degraded.Be mainly used in plant tissue culture, promote cell division and regulate cell differentiation, slow down aging, preserving fruit and vegetable utilizing is regulated the transportation of nutrient substance, promotes aspects such as solid.
Existing document proves, antioxidation, the antidotal effect of 6-furfuryl group amidopurin aspect plant is very tangible, also have bibliographical information 6-furfuryl group amidopurin to improve to comprise and reverse old and feeble ill effect, but the application on the internal organs of animal and human's body is also had no talent and done trial mammalian cell.
Summary of the invention
The objective of the invention is to, the application that amidopurin is used to prepare anti-liver injury medicament of chemical compound 6-furfuryl group is provided.
Above-mentioned hepatic injury is meant alcoholic liver injury and chemical liver injury.
Alcoholic liver injury comprises the fatty liver, hepatic fibrosis and the liver cirrhosis that are caused by ethanol or the disease of liver system.
Chemical liver injury comprises:
By aspirin, Phenylbutazone, ibuprofen, tetracycline, erythromycin, isoniazid, nitrofurantoin, intrahepatic cholestasis and hepatic necrosis that chlorpromazine, methyldopa, his horse azoles, estrogen or some antineoplastic agent cause; Liver necrocytosis, steatosis, liver cirrhosis and the hepatocarcinoma in various degree that chemical substances such as perhaps fine by trinitrotoluene, carbon tetrachloride, chloronaphthalene, acrylic aldehyde, arsenic, hydrargyrum, antimony, aniline, chloroform, dimethyl formamide, nitrophenols, acetaldehyde, organophosphor, propylene, lead cause.
The administering mode of chemical compound 6-furfuryl group amidopurin is oral administration, drug administration by injection or transdermal administration.
Chemical compound 6-furfuryl group amidopurin is used to prepare anti-liver injury medicament, can be used for powder, tablet, injection, nano-emulsion or the Application and Development of all dosage forms at present, and consumption is limited in the 450mg/kg.b.w.
Description of drawings
Fig. 1 is that transmission electron microscope observing is respectively organized mouse liver cell ultrastructure figure (TEM * 25000), wherein, and A: blank group mouse liver cell clear in structure, mitochondrion, endoplasmic reticulum structural integrity; B: vacuolar degeneration appears in the model group hepatocyte, and kernel disappears, and chromatin increases the limit collection; C: chemical compound 6-furfuryl group amidopurin low dose group hepatocyte structural integrity, the mitochondrion Mild edema, ridge is fuzzy; D: chemical compound 6-furfuryl group amidopurin high dose hepatocyte injury is slight, with blank group no significant difference.
The concrete test example that provides below in conjunction with accompanying drawing and inventor further specifies.
The specific embodiment
The applicant is through a large amount of evidences, chemical compound 6-furfuryl group amidopurin has the effect of anti-oxidative damage to animal and human's body liver, the anti-oxidative damage of having found chemical compound 6-furfuryl group amidopurin first acts on animal and human's body equally also to have, and has proved that chemical compound 6-furfuryl group amidopurin can be used in the medicine of preparation anti-liver injury.
1 material
1.1 test drug and reagent
Chemical compound 6-furfuryl group amidopurin is purchased in the Xiamen star is grand and is reached the chemical reagent company limited, is produced by U.S. Sanland company.Be mixed with the storing solution of 1000mg/L, 2000mg/L with the hydrochloric acid of 0.06mol/L, standby.Bifendate drop pill, Zhejiang Prov WanBang Pharmaceutical Co., Ltd, lot number 050907 faces with preceding and is made into 10gL with distilled water
-1Medicinal liquid; Malonaldehyde (MDA) detection kit, bio-engineering research institute, lot number: 20060320 are built up in Nanjing.Catalase (Catalasa CAT) detection kit, bio-engineering research institute is built up in Nanjing, lot number: 20060325, superoxide dismutase (SOD) detection kit, bio-engineering research institute is built up in Nanjing, lot number: 20060322, and the Coomassie brilliant blue test kit, bio-engineering research institute, lot number: 20060323 are built up in Nanjing.Albumin (Alb) detection kit, lot number 050251, Zhongsheng Beikong Biological Science ﹠ Technology Co., Ltd.; Alanine aminotransferase (ALT) detection kit (lot number D051262) and aspartate aminotransferase (AST) detection kit (lot number D060122) are available from Shanghai Foxing Changzheng medical science Co., Ltd.
1.2 key instrument
OPECORD50 type ultra-violet and visible spectrophotometer, German analytikjena company makes; The sub very much electronic balance of BS224S, Beijing Sai Duolisi instrument system company limited; HS10268 type 10～100 μ L pipettors, DRAGONMED company produces; The TD24-WS low speed autobalancing centrifuge, Hunan, Changsha instrument centrifuge instrument company limited; The H-600 transmission electron microscope, HIT; The CL8000 automatic clinical chemistry analyzer, day island proper Tianjin company;
1.3 experimental animal and damage model duplicate
A cleaning level ICR mice (Mus muscculus), female, body weight (20.0 ± 2.0) g, available from Xi'an Jiaotong University Medical College's Experimental Animal Center, the quality certification number: Shan moving card word 08-004 number.
6-furfuryl group amidopurin gastric infusion, dosage is calculated according to mg/Kg.b.w, once a day, a continuous week.Two hours lumbar injection CCl of last administration
4Solution duplicates the chmice acute liver injury model.
2 methods
2.1 grouping
Mice is divided into 5 groups immediately, specifically is grouped as follows:
A mistake! Do not find Reference source.Group: the blank group, irritate stomach 0.06mol/L hydrochloric acid 0.4mL, once a day, in a continuous week, last is irritated two hours lumbar injection solvent naphthas of stomach solution 0.2mL, animal fasting subsequently.
A mistake! Do not find Reference source.Group: CCl
4Model group is irritated stomach 0.06mol/L hydrochloric acid 0.4mL, and once a day, in a continuous week, last is irritated two hours lumbar injection 3.2%CCl of stomach
4Oil solution 0.2mL duplicates the chmice acute liver injury model, animal fasting subsequently.
A mistake! Do not find Reference source.Group: bifendate group: irritate stomach 10g/L bifendate medicinal liquid 0.4mL, dosage is 200mg/Kg.b.w, and once a day, in a continuous week, last is irritated two hours lumbar injection 3.2%CCl of stomach
4Oil solution 0.2mL duplicates the chmice acute liver injury model, animal fasting subsequently.
A mistake! Do not find Reference source.Group: chemical compound 6-furfuryl group amidopurin low dosage protection group: irritate stomach 1000mg/L 6-furfuryl group amidopurin medicinal liquid 0.4mL, dosage is 20mg/Kg.b.w, and once a day, in a continuous week, last is irritated two hours lumbar injection 3.2%CCl of stomach
4Oil solution 0.2mL duplicates the chmice acute liver injury model, animal fasting subsequently.
A mistake! Do not find Reference source.Group: chemical compound 6-furfuryl group amidopurin high dose protection group: irritate stomach 2000mg/L 6-furfuryl group amidopurin medicinal liquid 0.4mL, dosage is 40mg/Kg.b.w, and once a day, in a continuous week, last is irritated two hours lumbar injection 3.2%CCl of stomach
4Oil solution 0.2mL duplicates the chmice acute liver injury model, animal fasting subsequently.
2.2 sample to be tested collection
Mice is put to death in fasting fast after 24 hours, and separation of serum.Get the part hepatic tissue, centrifugal with the liver homogenate of making 1% and 10% after the cold saline rinsing, get supernatant, prepare to detect every index.Other gets the part hepatic tissue, is cut into about 1mm fast on ice
3Fritter, 4 ℃ of 4% glutaraldehydes down fixedly ethanol dewater step by step, electron microscopic section is made in the epoxy resin embedding, the H-600 transmission electron microscope is observed ultrastructure of hepatic cell down.
2.3 serum detects index
Adopt automatic clinical chemistry analyzer to measure ALT, AST activity and Alb content.
2.4 the mensuration of total protein
The requirement of by specification before measuring antioxidase and MDA, is measured the total protein content of 10% liver homogenate earlier, with the Coomassie brilliant blue method, respectively manages the A value with ultraviolet-uisible spectrophotometer in 540nm mensuration, calculates the protein content of each pipe by following formula.
Protein content (g/L)=(measuring pipe A value/standard pipe A value) * standard pipe concentration (g/L)
2.5 T-SOD measures in the liver homogenate
Get 1% liver homogenate, require operation according to test kit, with ultra-violet and visible spectrophotometer 550nm place colorimetric (distilled water returns to zero, the 1cm cuvette).Calculate the T-SOD unit of activity according to following formula:
2.6 liver homogenate MDA Determination on content
Get 10% liver homogenate, require operation according to test kit, with ultra-violet and visible spectrophotometer 532nm place colorimetric (distilled water returns to zero, the 1cm cuvette).Calculate MDA content according to following formula:
2.7 the active mensuration of liver homogenate CAT
Get 1% liver homogenate, require operation according to test kit, with ultra-violet and visible spectrophotometer 240nm place colorimetric (distilled water returns to zero, the 1cm cuvette).Calculate the CAT enzyme activity according to following formula:
In the formula, 2.303 expressions must multiply by 2.303 when natural logrithm is converted into common logarithm log
A*** represents the extension rate of hemoglobin or histone.
B**** represents every milliliter of hemoglobin gram number or every milliliter of histone gram number in the sample.
3 results
3.1 chemical compound 6-furfuryl group amidopurin is to the influence of mice serum biochemical indicator
Model group Serum ALT and AST obviously increase, and serum Alb obviously reduces, and with the blank group highly significant difference (P＜0.01) are arranged more all, and the chmice acute hepatic injury modeling success of this experiment is described.6-furfuryl group amidopurin low dose group Serum ALT vigor obviously reduces (P＜0.01) than model group, the AST vigor obviously reduces (P＜0.05), Alb content than model group obviously raise (P＜0.05) than model group, chemical compound 6-furfuryl group amidopurin high dose group Serum ALT, AST and Alb and model group more all have highly significant difference (P＜0.01), its effect similar to positive control bifendate group (P＞0.05).See Table 1.
Table 1 chemical compound 6-furfuryl group amidopurin is to the n=6 that influences of mice serum ALT, AST and Alb, X ± S
| Group | Dosage/mgKg -1·d -1 | ALT/U·L -1 | AST/U·L -1 | Alb/g·L -1 |
| The blank group | - | 83.9±1.60 c | 154.2±5.6 c | 33.6±0.6 c |
| CCl 4Model group | - | 287.1±9.1 | 314.3±13.2 | 24.94±0.6 |
| The bifendate group | 200 | 172.0±7.1 c | 256.6±6.8 c | 31.7±0.8 c |
| 6-furfuryl group amidopurin low dose group | 20 | 211.8±9.8a c | 281.5±9.9 ab | 26.4±0.4 ab |
| 6-furfuryl group amidopurin high dose group | 40 | 180.04±8.2 ac | 238.5±6.5 ac | 31.3±1.0 ac |
ALT: alanine aminotransferase; AST: aspartate aminotransferase; Alb: albumin.Compare with positive control bifendate group,, compare in twos through variance analysis:
aCompare with model group P＞0.05, through variance analysis, compares in twos:
bP＜0.05,
cP＜0.01
3.2 chemical compound 6-furfuryl group amidopurin is to the influence of murine liver tissue biochemical indicator
6-furfuryl group amidopurin low dose group hepatic tissue CAT vigor is than model group obviously raise (P＜0.01), the SOD vigor than model group obviously raise (P＜0.05), MDA content is starkly lower than model group (P＜0.05), 6-furfuryl group amidopurin high dose group hepatic tissue CAT, SOD and MDA and model group more all have highly significant difference (P＜0.01), its effect similar to positive control bifendate group (P＞0.05).See Table 2.
Table 2 chemical compound 6-furfuryl group amidopurin is to the n=6 that influences of murine liver tissue CAT, SOD and MDA, X ± S
| Group | Dosage/mgKg -1·d -1 | CAT/ U·g -1pro | SOD/ U·mg -1pro | MDA/ nmol·mg -1pro |
| The blank group | - | 162.2±9.5 c | 117.1±6.4 c | 0.754±0.09 c |
| CCl 4Model group | - | 92.6±3.3 | 75.8±5.5 | 1.60±0.10 |
| The bifendate group | 200 | 122.9±8.5 c | 101.2±6.3 c | 1.25±0.05 c |
| 6-furfuryl group amidopurin low dose group | 20 | 114.9±8.6 ac | 91.9±4.0 ab | 1.42±0.05 ab |
| 6-furfuryl group amidopurin high dose group | 40 | 143.8±9.5 ac | 107.7±6.8 ac | 1.13±0.03 ac |
SOD: superoxide dismutase; CAT: catalase; MDA: malonaldehyde.Compare with positive control bifendate group,, compare in twos through variance analysis:
aCompare with model group P＞0.05, through variance analysis, compares in twos:
bP＜0.05,
cP＜0.01
3.3 transmission electron microscope is to acute liver damage mouse liver cell Ultrastructural observation
Blank group mouse liver cell organelle is abundant, the rough endoplasmic reticulum regularity of distribution, structure of mitochondria is normal, and ridge is flourishing and high-visible, and nuclear is justified greatly, between two parties, the heteronuclear film is clear, and nuclear periphery is slick and sly, and chromatin is few and disperse, euchromatin is many and concentrate blood sinus endothelial system no abnormality seen variation (Figure 1A).The most hepatocyte enlargements of CCl4 model group mice a large amount of fat occur and drip in the Cytoplasm, drip based on medium and small fat; There are the most cavitys that differ in size to form in the cell, are the kitchen range shape more and distribute; The swelling of mitochondrion height, localized degradation or all degradeds take place in the ridge arrangement disorder, and internal structure disappears, and double membrane structure is unclear; Rough endoplasmic reticulum (RER) mild swelling, but be in the function disabled state, there is part to take off the granule phenomenon; Smooth endoplasmic reticulum (SER) hypertrophy is blister; The glycogen granule obviously reduces; The nucleus edge is irregular, and kernel disappears, and chromatin increases the limit collection, and perinuclear space is fuzzy.Blood sinus generally narrows down, and has the erythrocyte stasis of blood in heaps long-pending more, and the Kupffer phagocytic function is active, and the hole endotheliocyte does not have obvious swelling, the Di Shi gap turn narrow, and hepatocyte hole face microvillus reduces (Figure 1B).6-furfuryl group amidopurin low dose group nucleus edge is irregular, and is light than model group, and perinuclear space is fuzzy, the mitochondrion Mild edema, and ridge blurs (Fig. 1 C).6-furfuryl group amidopurin high dose group liver cell nuclear is normal substantially, and perinuclear space is clear, and mitochondrion is high-visible, ridge reduces than model group and obviously improves near the blank group, blood sinus width and blank group do not have significant difference, and the long-pending phenomenon of the kitchen range erythrocyte stasis of blood disappears, Di Shi gap broaden (Fig. 1 D).
4 conclusions
Experimental result shows that chemical compound 6-furfuryl group amidopurin is to CCl
4It is inhibited that the hepatic tissue CAT that acute injury causes reduces, SOD reduces, MDA raises, and the every index of 6-furfuryl group amidopurin group is compared with model group all has significant difference (P＜0.01); Simultaneously can keep the hepatocyte normal ultrastructure, protect the cell rough endoplasmic reticulum simultaneously, cell membrane, nuclear membrane, subcellular structures such as mitochondrion by electron microscopic observation chemical compound 6-furfuryl group amidopurin.Can prove that by this experiment 6-furfuryl group amidopurin has protection chmice acute hepatic injury effect.
Claims (6)
1. the chemical compound 6-furfuryl group amidopurin application that is used to prepare anti-liver injury medicament.
2. application as claimed in claim 1 is characterized in that, described hepatic injury is alcoholic liver injury and chemical liver injury.
3. application as claimed in claim 1 is characterized in that, described alcoholic liver injury comprises the fatty liver, hepatic fibrosis and the liver cirrhosis that are caused by ethanol or the disease of liver system.
4. application as claimed in claim 1 is characterized in that, described chemical liver injury comprises:
By aspirin, Phenylbutazone, ibuprofen, tetracycline, erythromycin, isoniazid, nitrofurantoin, intrahepatic cholestasis and hepatic necrosis that chlorpromazine, methyldopa, his horse azoles, estrogen or some antineoplastic agent cause; Liver necrocytosis, steatosis, liver cirrhosis and the hepatocarcinoma in various degree that chemical substances such as perhaps fine by trinitrotoluene, carbon tetrachloride, chloronaphthalene, acrylic aldehyde, arsenic, hydrargyrum, antimony, aniline, chloroform, dimethyl formamide, nitrophenols, acetaldehyde, organophosphor, propylene, lead cause.
5. application as claimed in claim 1 is characterized in that, the administering mode of described chemical compound 6-furfuryl group amidopurin is oral administration, drug administration by injection or transdermal administration.
6. application as claimed in claim 1 is characterized in that, the pharmaceutical dosage form of described chemical compound 6-furfuryl group amidopurin is powder, tablet, injection, nano-emulsion or existing all dosage forms.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102670615A (en) * | 2012-01-04 | 2012-09-19 | 河南科技大学 | Application of 6-benzyl aminopurine compound in terms of preparation of composition for suppressing oxidative injury to brain tissues |
| CN102670614A (en) * | 2012-01-04 | 2012-09-19 | 河南科技大学 | Application of compound 6-benzylaminopurine (BA) in preparation of composition for inhibiting oxidative damage of hepatic tissues |
-
2007
- 2007-04-03 CN CNA2007100176155A patent/CN101036653A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102670615A (en) * | 2012-01-04 | 2012-09-19 | 河南科技大学 | Application of 6-benzyl aminopurine compound in terms of preparation of composition for suppressing oxidative injury to brain tissues |
| CN102670614A (en) * | 2012-01-04 | 2012-09-19 | 河南科技大学 | Application of compound 6-benzylaminopurine (BA) in preparation of composition for inhibiting oxidative damage of hepatic tissues |
| CN102670614B (en) * | 2012-01-04 | 2013-09-04 | 河南科技大学 | Application of compound 6-benzylaminopurine (BA) in preparation of composition for inhibiting oxidative damage of hepatic tissues |
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