CN108653267A - Dihydroquercetin is preparing the purposes in protecting drug induccd acute liver damage drug - Google Patents
Dihydroquercetin is preparing the purposes in protecting drug induccd acute liver damage drug Download PDFInfo
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- CN108653267A CN108653267A CN201710203674.5A CN201710203674A CN108653267A CN 108653267 A CN108653267 A CN 108653267A CN 201710203674 A CN201710203674 A CN 201710203674A CN 108653267 A CN108653267 A CN 108653267A
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- dihydroquercetin
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- acetaminophen
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- CXQWRCVTCMQVQX-LSDHHAIUSA-N (+)-taxifolin Chemical compound C1([C@@H]2[C@H](C(C3=C(O)C=C(O)C=C3O2)=O)O)=CC=C(O)C(O)=C1 CXQWRCVTCMQVQX-LSDHHAIUSA-N 0.000 title claims abstract description 43
- XCGZWJIXHMSSQC-UHFFFAOYSA-N dihydroquercetin Natural products OC1=CC2OC(=C(O)C(=O)C2C(O)=C1)c1ccc(O)c(O)c1 XCGZWJIXHMSSQC-UHFFFAOYSA-N 0.000 title claims abstract description 42
- 239000003814 drug Substances 0.000 title claims abstract description 26
- 229940079593 drug Drugs 0.000 title claims abstract description 15
- 206010067125 Liver injury Diseases 0.000 title claims abstract description 10
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 claims abstract description 68
- 229960005489 paracetamol Drugs 0.000 claims abstract description 35
- 210000003494 hepatocyte Anatomy 0.000 claims abstract description 12
- 238000011740 C57BL/6 mouse Methods 0.000 claims abstract description 8
- 230000003908 liver function Effects 0.000 claims abstract description 6
- 230000009036 growth inhibition Effects 0.000 claims abstract description 5
- 230000002159 abnormal effect Effects 0.000 claims abstract description 4
- 230000001575 pathological effect Effects 0.000 claims abstract description 4
- 230000034994 death Effects 0.000 claims abstract description 3
- 208000008964 Chemical and Drug Induced Liver Injury Diseases 0.000 claims description 13
- 206010072268 Drug-induced liver injury Diseases 0.000 claims description 7
- 231100000439 acute liver injury Toxicity 0.000 claims description 3
- 231100000753 hepatic injury Toxicity 0.000 abstract description 5
- 230000006698 induction Effects 0.000 abstract description 5
- 210000004027 cell Anatomy 0.000 abstract description 2
- 230000000704 physical effect Effects 0.000 abstract 1
- 102000003855 L-lactate dehydrogenase Human genes 0.000 description 8
- 108700023483 L-lactate dehydrogenases Proteins 0.000 description 8
- PWKSKIMOESPYIA-BYPYZUCNSA-N L-N-acetyl-Cysteine Chemical compound CC(=O)N[C@@H](CS)C(O)=O PWKSKIMOESPYIA-BYPYZUCNSA-N 0.000 description 7
- 229960004308 acetylcysteine Drugs 0.000 description 7
- 210000005228 liver tissue Anatomy 0.000 description 7
- 241000699666 Mus <mouse, genus> Species 0.000 description 6
- 102100036475 Alanine aminotransferase 1 Human genes 0.000 description 5
- 108010082126 Alanine transaminase Proteins 0.000 description 5
- 108010003415 Aspartate Aminotransferases Proteins 0.000 description 5
- 102000004625 Aspartate Aminotransferases Human genes 0.000 description 5
- 238000000034 method Methods 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 102000029816 Collagenase Human genes 0.000 description 2
- 108060005980 Collagenase Proteins 0.000 description 2
- 229920000858 Cyclodextrin Polymers 0.000 description 2
- 239000001116 FEMA 4028 Substances 0.000 description 2
- 241000544657 Larix gmelinii Species 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- ZONYXWQDUYMKFB-UHFFFAOYSA-N SJ000286395 Natural products O1C2=CC=CC=C2C(=O)CC1C1=CC=CC=C1 ZONYXWQDUYMKFB-UHFFFAOYSA-N 0.000 description 2
- 230000005856 abnormality Effects 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 208000029618 autoimmune pulmonary alveolar proteinosis Diseases 0.000 description 2
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 description 2
- 235000011175 beta-cyclodextrine Nutrition 0.000 description 2
- 229960004853 betadex Drugs 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 229960002424 collagenase Drugs 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 229930003949 flavanone Natural products 0.000 description 2
- -1 flavanone compound Chemical class 0.000 description 2
- 235000011981 flavanones Nutrition 0.000 description 2
- RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 239000007928 intraperitoneal injection Substances 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
- 210000005229 liver cell Anatomy 0.000 description 2
- 230000010412 perfusion Effects 0.000 description 2
- 239000013641 positive control Substances 0.000 description 2
- 238000010186 staining Methods 0.000 description 2
- 206010067484 Adverse reaction Diseases 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 108010024636 Glutathione Proteins 0.000 description 1
- 206010019663 Hepatic failure Diseases 0.000 description 1
- 206010019837 Hepatocellular injury Diseases 0.000 description 1
- 238000000134 MTT assay Methods 0.000 description 1
- 231100000002 MTT assay Toxicity 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 210000000683 abdominal cavity Anatomy 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 230000006838 adverse reaction Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000003064 anti-oxidating effect Effects 0.000 description 1
- 230000002155 anti-virotic effect Effects 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000002238 attenuated effect Effects 0.000 description 1
- 230000004663 cell proliferation Effects 0.000 description 1
- 230000003833 cell viability Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000009509 drug development Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 229960003180 glutathione Drugs 0.000 description 1
- 206010019692 hepatic necrosis Diseases 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000010874 in vitro model Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 231100000849 liver cell damage Toxicity 0.000 description 1
- 231100000835 liver failure Toxicity 0.000 description 1
- 208000007903 liver failure Diseases 0.000 description 1
- 231100000149 liver necrosis Toxicity 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000009456 molecular mechanism Effects 0.000 description 1
- 230000036542 oxidative stress Effects 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 230000000451 tissue damage Effects 0.000 description 1
- 231100000827 tissue damage Toxicity 0.000 description 1
- 208000037816 tissue injury Diseases 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
The invention belongs to pharmaceutical fields, are related to dihydroquercetin and are preparing the purposes of the purposes in protecting drug induccd acute liver damage drug, especially dihydroquercetin in the drug induccd liver injury medicament for preparing protection paracetamol induction.The present invention passes through cell and zoopery, it confirms that dihydroquercetin can weaken primary hepatocyte growth inhibition and the death of paracetamol induction, and improves abnormal raising and the change of pathologic structure of the C57BL/6 mouse liver function related biochemical indicators of paracetamol induction.The dihydroquercetin can be used for preparing the drug for medicine physical property hepatic injury, the especially medicine of the acute liver damage of paracetamol induction.
Description
Technical Field
The invention belongs to the field of pharmacy, and relates to application of dihydroquercetin in preparation of a drug-induced acute liver injury protection drug, in particular to application of dihydroquercetin in preparation of a drug-induced liver injury protection drug induced by acetaminophen.
Background
The prior art discloses that Drug-induced liver injury (DILD) is an inevitable problem in Drug development and clinical medication, wherein Acetaminophen (APAP) -induced liver injury is the most common and can cause severe liver necrosis, liver failure and even death. The currently common treatment method in clinical practice is the method of intravenous drip of the antioxidant N-acetylcysteine (NAC), which studies have shown that NAC, a precursor of glutathione, can relieve oxidative stress in the liver, and has the disadvantages of short half-life, effectiveness only in early stages, and a series of adverse reactions.
Dihydroquercetin (DHQ), also known as Taxifolin (TAX), is prepared from Larix Gmelini (Larix Gmelini) belonging to PinaceaeLarix gmelinii Rupr.) The flavanone compound separated and extracted from the raw materials has various pharmacological activities such as anti-inflammatory, antioxidation, antivirus and the like, and the research of recent years finds that the flavanone compound hasHas protective effect on cardiovascular diseases. So far, no research report on the application of the compound in protecting acetaminophen-induced liver injury exists.
Based on the current research situation of the prior art, the inventor of the application intends to provide a new application of dihydroquercetin in preparing a medicine for protecting drug-induced acute liver injury, in particular to an application of dihydroquercetin in preparing a medicine for protecting drug-induced liver injury induced by acetaminophen.
Disclosure of Invention
The invention aims to provide a new application of dihydroquercetin in preparing a medicine for protecting drug-induced acute liver injury, in particular to an application of dihydroquercetin in preparing a medicine for protecting drug-induced liver injury induced by acetaminophen, aiming at the defects in the prior art.
The invention researches and detects the function and molecular mechanism of natural antioxidant dihydroquercetin in liver protection in acetaminophen-induced liver injury through animal experiments; wherein,
according to the invention, primary cultured mouse liver cells are adopted, and the effect and mechanism of protecting acetaminophen-induced liver cell damage by dihydroquercetin in vitro are detected, and experimental results show that the dihydroquercetin can remarkably weaken the growth inhibition and lactate dehydrogenase release (shown in figures 1 and 2) of acetaminophen-induced primary mouse liver cells and has dose dependence;
according to the invention, an acetaminophen-induced acute liver injury model is injected into the abdominal cavity of a C57BL/6 mouse, the morbidity process is similar to that of the model, and experimental results show that dihydroquercetin can obviously weaken abnormal rise of acetaminophen-induced liver function related biochemical indicators, namely alanine Aminotransferase (ALT) and aspartate Aminotransferase (AST) (as shown in figure 3), and the pathological results are obviously improved (as shown in figure 4).
The invention provides a new application of dihydroquercetin in preparing a medicine for protecting drug-induced acute liver injury, in particular to an application of dihydroquercetin in preparing a medicine for protecting acetaminophen-induced drug-induced liver injury; the dihydroquercetin can be used for preparing medicines for treating acetaminophen-induced drug-derived acute liver injury, and can be further used for developing liver-protecting medicines.
Drawings
FIG. 1 shows that dihydroquercetin attenuates acetaminophen-induced hepatocyte growth inhibition in primary mice, wherein primary mouse hepatocytes are derived from C57BL/6 mice, extracted by IV collagenase in situ perfusion, cells are pretreated with different concentrations of dihydroquercetin (0-200 μ M) for 1 hour, and are then subjected to acetaminophen (10 mM) induction in an in vitro model of acute drug-induced liver injury, and after 24 hours, the cell viability is measured by MTT method, wherein p is 0.05, p is 0.01, and # is 0.01, compared with a model control group.
FIG. 2 shows that dihydroquercetin attenuates acetaminophen-induced lactate dehydrogenase release from primary hepatocytes, wherein the LDH detection kit is used to detect primary hepatocyte damage by p < 0.05;. p < 0.01;. p # p <0.01, as compared to model controls.
FIG. 3 shows the abnormality of liver function-related biochemical indicators of acetaminophen-induced C57BL/6 mice protected by dihydroquercetin, wherein the C57BL/6 mice were fasted for 12 hours before the experiment, administered by intraperitoneal injection of 25 mg/kg, 50 mg/kg and 100 mg/kg dihydroquercetin (dissolved in 25% β -cyclodextrin), NAC 600 mg/kg was used as a positive control, acetaminophen was injected intraperitoneally for 500 mg/kg after 1 hour, and sacrificed after 24 hours, whole blood and liver tissues were taken, ALT, AST were used to evaluate liver functions, and p is < 0.05;. p is < 0.01.
Fig. 4 is a graph of dihydroquercetin attenuating acetaminophen-induced liver tissue damage, wherein H & E staining is shown.
Detailed Description
Example 1 Dihydroquercetin protects acetaminophen-induced damage to primary hepatocytes
Primary mouse hepatocytes were taken from C57BL/6 mice, extracted by IV collagenase in situ perfusion, inoculated into 96-well plates, divided into blank control group, model control group (APAP 10 mM), dihydroquercetin-treated group (12.5, 25, 50, 100, 200 μ M), and positive drug-treated group (NAC 2.5 mM), and cultured at 37 ℃ for 24 hours, followed by MTT assay, and the cell proliferation rate was calculated, and the results showed that dihydroquercetin significantly reduced the growth inhibition of acetaminophen-induced primary hepatocytes with increasing dose (as shown in fig. 1).
Example 2 Dihydroquercetin attenuated Acetaminophen-induced lactate dehydrogenase Release from Primary hepatocytes
Primary hepatocytes were inoculated in 96-well plates and cultured overnight, dihydroquercetin (12.5, 25, 50, 100, 200 μ M) and a positive drug (NAC 2.5 mM) were pretreated in advance, acetaminophen (10 mM) was added after 1 hour for treatment, Lactate Dehydrogenase (LDH) assay was performed after 24 hours of culture at 37 ℃, and LDH release rate was calculated, and the results showed that dihydroquercetin significantly reduced the release of acetaminophen-induced primary hepatocyte LDH with increasing dose (as shown in fig. 2).
Example 3 Dihydroquercetin modulation of Acetaminophen-induced abnormalities in Biochemical indicators of liver function in mice
The C57BL/6 mouse is fasted for 12 hours before the experiment, 25 mg/kg, 50 mg/kg and 100 mg/kg dihydroquercetin (dissolved in 25% β -cyclodextrin) is administrated by intraperitoneal injection, NAC 600 mg/kg is taken as a positive control, acetaminophen is injected intraperitoneally for 500 mg/kg after 1 hour, the dihydroquercetin is killed after 24 hours, whole blood and liver tissues are taken, and ALT and AST detection results show that the dihydroquercetin can obviously reduce the abnormal elevation of ALT and AST in the mouse serum induced by acetaminophen (as shown in figure 3).
Example 4 Dihydroquercetin ameliorates Acetaminophen-induced liver tissue injury
The liver tissue of a mouse is taken and fixed in 4% paraformaldehyde overnight, the liver tissue is sliced after being embedded by paraffin and is subjected to H & E staining, a pathological structure is observed by a microscope and is photographed, and the experimental result shows that the dihydroquercetin can obviously improve the acetaminophen-induced liver tissue lesion (as shown in figure 4).
Claims (4)
1. Application of dihydroquercetin in preparing medicine for protecting drug-derived acute liver injury is provided.
2. The use according to claim 1, wherein said drug induced acute liver injury is acetaminophen-induced drug induced liver injury.
3. The use of claim 2, wherein said dihydroquercetin attenuates acetaminophen-induced primary hepatocyte growth inhibition and death.
4. The use according to claim 2, wherein said dihydroquercetin ameliorates acetaminophen-induced abnormal elevations of biochemical markers associated with liver function and pathological structural changes in C57BL/6 mice.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710203674.5A CN108653267A (en) | 2017-03-30 | 2017-03-30 | Dihydroquercetin is preparing the purposes in protecting drug induccd acute liver damage drug |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710203674.5A CN108653267A (en) | 2017-03-30 | 2017-03-30 | Dihydroquercetin is preparing the purposes in protecting drug induccd acute liver damage drug |
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| Publication Number | Publication Date |
|---|---|
| CN108653267A true CN108653267A (en) | 2018-10-16 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201710203674.5A Pending CN108653267A (en) | 2017-03-30 | 2017-03-30 | Dihydroquercetin is preparing the purposes in protecting drug induccd acute liver damage drug |
Country Status (1)
| Country | Link |
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| CN (1) | CN108653267A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109864987A (en) * | 2019-03-18 | 2019-06-11 | 广东药科大学 | Application of the Quercetin in the drug of preparation protection and the hepatic injury of medicine physical property |
-
2017
- 2017-03-30 CN CN201710203674.5A patent/CN108653267A/en active Pending
Non-Patent Citations (6)
| Title |
|---|
| 佟苗苗等: "花旗松素对异烟肼-利福平诱导小鼠肝损伤的保护作用", 《第十届中国中药鉴定学教学研讨会暨第十三届全国中药标本馆学术研讨会论文汇编》 * |
| 苏少慧: "《临床实用肝脏病学》", 30 June 2011, 河北科学技术出版社 * |
| 赵香兰: "《临床药理学》", 31 August 2003, 中山大学出版社 * |
| 邱德凯: "《慢性肝病临床并发症：现代诊治概念》", 31 October 2001, 上海科学技术出版社 * |
| 郝丽英: "《药物毒理学 第2版》", 30 September 2016, 上海科学技术出版社 * |
| 郭丁妮: "异烟肼和利福平合用致小鼠肝细胞毒_省略_择性抑制剂对其保护作用的机制探讨", 《中国优秀硕士学位论文全文数据库 医药卫生科技辑》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109864987A (en) * | 2019-03-18 | 2019-06-11 | 广东药科大学 | Application of the Quercetin in the drug of preparation protection and the hepatic injury of medicine physical property |
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Application publication date: 20181016 |