CN111995610A - Application of urolithin compound in medicine for treating glioblastoma - Google Patents
Application of urolithin compound in medicine for treating glioblastoma Download PDFInfo
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- CN111995610A CN111995610A CN201910443193.0A CN201910443193A CN111995610A CN 111995610 A CN111995610 A CN 111995610A CN 201910443193 A CN201910443193 A CN 201910443193A CN 111995610 A CN111995610 A CN 111995610A
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- urolithin
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- glioblastoma
- medicament
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 27
- 208000005017 glioblastoma Diseases 0.000 title claims abstract description 23
- 229930186301 urolithin Natural products 0.000 title claims abstract description 19
- 239000003814 drug Substances 0.000 title claims description 12
- 239000002775 capsule Substances 0.000 claims abstract description 6
- 239000008187 granular material Substances 0.000 claims abstract description 6
- 239000007788 liquid Substances 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 7
- 239000002552 dosage form Substances 0.000 abstract 1
- 238000000338 in vitro Methods 0.000 abstract 1
- WXUQMTRHPNOXBV-UHFFFAOYSA-N Urolithin B Chemical compound C1=CC=C2C3=CC=C(O)C=C3OC(=O)C2=C1 WXUQMTRHPNOXBV-UHFFFAOYSA-N 0.000 description 22
- 206010028980 Neoplasm Diseases 0.000 description 12
- 241000699670 Mus sp. Species 0.000 description 10
- RIUPLDUFZCXCHM-UHFFFAOYSA-N urolithin-A Natural products OC1=CC=C2C3=CC=C(O)C=C3OC(=O)C2=C1 RIUPLDUFZCXCHM-UHFFFAOYSA-N 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 9
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 230000005764 inhibitory process Effects 0.000 description 4
- 206010018338 Glioma Diseases 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical group [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 208000009911 Urinary Calculi Diseases 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 239000002504 physiological saline solution Substances 0.000 description 3
- 229910002012 Aerosil® Inorganic materials 0.000 description 2
- 208000003174 Brain Neoplasms Diseases 0.000 description 2
- 206010007027 Calculus urinary Diseases 0.000 description 2
- 208000032612 Glial tumor Diseases 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 230000002159 abnormal effect Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000013642 negative control Substances 0.000 description 2
- 238000007873 sieving Methods 0.000 description 2
- JMGCAHRKIVCLFW-UHFFFAOYSA-N 1-O-Galloylcastalagin Natural products Oc1cc(cc(O)c1O)C(=O)OC2C3OC(=O)c4c2c(O)c(O)c(O)c4c5c(O)c(O)c(O)c6c5C(=O)OC3C7OC(=O)c8cc(O)c(O)c(O)c8c9c(O)c(O)c(O)cc9C(=O)OCC7OC(=O)c%10cc(O)c(O)c(O)c6%10 JMGCAHRKIVCLFW-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 201000010915 Glioblastoma multiforme Diseases 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- BPEGJWRSRHCHSN-UHFFFAOYSA-N Temozolomide Chemical compound O=C1N(C)N=NC2=C(C(N)=O)N=CN21 BPEGJWRSRHCHSN-UHFFFAOYSA-N 0.000 description 1
- 230000003187 abdominal effect Effects 0.000 description 1
- 229960004977 anhydrous lactose Drugs 0.000 description 1
- 230000000890 antigenic effect Effects 0.000 description 1
- 230000008436 biogenesis Effects 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 201000007983 brain glioma Diseases 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 206010061428 decreased appetite Diseases 0.000 description 1
- JMGCAHRKIVCLFW-CNWXVVPTSA-N ellagitannin Chemical compound OC1=C(O)C(O)=CC(C(=O)O[C@H]2C3=C4C(=O)O[C@@H]2[C@@H]2[C@@H]5OC(=O)C6=CC(O)=C(O)C(O)=C6C6=C(O)C(O)=C(O)C=C6C(=O)OC[C@H]5OC(=O)C5=CC(O)=C(O)C(O)=C5C=5C(O)=C(O)C(O)=C(C=5C(=O)O2)C4=C(O)C(O)=C3O)=C1 JMGCAHRKIVCLFW-CNWXVVPTSA-N 0.000 description 1
- 229920001968 ellagitannin Polymers 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 208000022080 low-grade astrocytoma Diseases 0.000 description 1
- 230000003211 malignant effect Effects 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 238000010172 mouse model Methods 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 238000001543 one-way ANOVA Methods 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000002980 postoperative effect Effects 0.000 description 1
- 238000001959 radiotherapy Methods 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 229960004964 temozolomide Drugs 0.000 description 1
- 238000004704 ultra performance liquid chromatography Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
-
- 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
- A61K31/365—Lactones
- A61K31/366—Lactones having six-membered rings, e.g. delta-lactones
- A61K31/37—Coumarins, e.g. psoralen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention relates to a urolithin compound which has the structure as shown on the right. The compound shows strong anti-glioblastoma activity in vitro, and can be used for preparing various pharmaceutical dosage forms for treating anti-glioblastoma by being matched with a medicinal carrier, such as capsules, granules, oral liquid or tablets.
Description
Technical Field
The invention relates to the field of medicines, in particular to a urolithin compound with an anti-glioblastoma effect.
Background
Gliomas are the most common invasive tumors of the central nervous system. Glioblastoma (GBM), also known as glioblastoma multiforme, is a quaternary glioma classified by the World Health Organization (WHO), accounting for 15% of brain tumors, a highly malignant and highly recurrent brain tumor. Glioblastomas can develop from normal cells or from existing low grade astrocytomas with a median survival time of 14.6 months. Generally, glioma treatment involves surgery, post-operative use of chemotherapy and radiation therapy, and temozolomide is the current first-line chemotherapeutic for glioblastoma. However, less than 3% -5% of people can live for 5 years, and there is still a lack of effective means for treating glioblastoma. Therefore, the search for new drugs for treating glioblastoma is urgent.
Our research reveals that the urolithin compound oral preparation has strong anti-glioblastoma effect and can be used as a potential drug for treating glioblastoma.
Disclosure of Invention
The invention aims to provide application of the urolithin compound oral preparation in preparation of a drug for treating glioblastoma.
The urolithin compound has a structure shown in figure 1.
The invention relates to an application of a urolithin compound urolithin B medicament in treating glioblastoma. The medicine is capsules, granules, oral liquid or tablets prepared by matching the compounds with pharmaceutically acceptable excipients.
The other urinary calculus compound oral preparation is better than other preparations in treating the glioblastoma.
Drawings
FIG. 1 Structure of urolithin B.
FIG. 2 shows the effect of orally administered urolithin B on glioblastoma inhibition. MRI images of saline group (NS) and urolithin B group (UB) at 0 day, 7 day, and 14 days of administration, respectively.
FIG. 3 is a statistical graph of the inhibitory effect of intraperitoneal administration of urolithin B on glioblastoma. The two groups are normal saline group and urolithin B group. *p<0.05, which shows that the ratio of the compound is different from the physiological saline, and the data are analyzed by single-factor variance.
FIG. 4 is a statistical graph of the inhibitory effect of oral urolithin B on glioblastoma. Divided into two groups, normal saline group, urinary calculus
And (B) element B. *p<0.05, which shows that the ratio of the compound is different from the physiological saline, and the data are analyzed by single-factor variance.
Detailed Description
Example 1: preparation of compound urolithin compound: taking 100 g of ellagitannin, adding 1000 ml of water, electrically stirring for 30 days, centrifuging the extracting solution, wherein the centrifugation conditions are as follows: 15000 rpm for 10 min to obtain the urolithin compound.
The mass spectrum guided preparation liquid chromatography is used for separating the urolithin compounds, main positive ions in a positive ion mode can be obtained from a UPLC spectrogram, and an MSD value to be detected is input into a workstation: 930, drying gas flow rate of 12L/min, drying gas temperature of 350 ℃, atomizing gas pressure of 350 psig and capillary voltage of 3000V. Balancing: the column was equilibrated with 50% of phase A and 50% of phase B for about 15 min. The sample introduction amount is set to 4.5 mL, the target fraction is collected by manual sample receiving, and the target fraction enters the fraction collector. Vacuum drying under reduced pressure to obtain the compound urolithin compound.
Example 2: antigenic glioblastoma effect of urolithin B
After the mice are modeled by using C6 cells, a T2 phase of the brain of the mice is scanned by using a mouse nuclear magnetic scanning system on the 7 th day, most of the left caudate nuclei of the mice have abnormal biogenesis, the inside of the caudate nuclei has a liquefaction phenomenon, the periphery of the caudate nuclei has edema, and the boundary is clear. The nmr images were screened to obtain 12 mice with tumors of similar size, their initial tumor size was recorded and marked. Of the 12 ICR model mice, 6 were used as negative control groups, and were gavaged with 0.2 mL of physiological saline per day, and 6 were used as the gavaged group of urolithin B, and the administration dose was 40 mg/kg according to the reference. Dosing was performed for 14 days, nuclear magnetic scans were performed every 7 days and tumor sizes were recorded. The control mice were in good condition at 0-5 days and had no apparent abnormal activity. After 5 days, the mice in the control group have obvious reduced activity and weight, and after 10 days, the mice in the control group have limb discordance. Compared with the control group mice, the mice in the administration group have inappetence in the initial stage, have improved later state, and have no limb discordance and obvious weight loss. No death of the mice was observed until the end of the experiment.
The formula for tumor volume V = length × width × (number of layers-1) × 0.5/2, 0.5 is the layer thickness in mm.
Percent tumor inhibition rate = (1-average tumor weight of administration group/average tumor weight of negative control group) × 100%
The size of the tumor volume is calculated according to the measured nuclear magnetic scans, and the one-way anova is carried out by using Graphpad Prism 7, and the graph is drawn, wherein the abscissa is a group, and the ordinate is the change of the tumor volume before and after the administration.
The experimental result shows that the urolithin B has an inhibiting effect on brain glioma under the intraperitoneal injection and oral administration routes, and the tumor inhibition rates respectively reach 46.91% (see figure 2 and figure 3) and 67.45% (see figure 4). The tumor inhibition effect of the oral administration of the urolithin B is better than that of the abdominal administration, and the growth state of a mouse is not obviously affected after the administration, so that the oral administration mode of the urolithin B is further determined.
Example 3: preparation of capsules
And (2) uniformly mixing the compound of the urinary stone compounds obtained in the example 1 and 280 mg of aerosil, sieving, adding a proper amount of magnesium stearate, uniformly mixing, granulating by using a dry granulating machine, sieving to obtain granules of 40-80 meshes, and filling into capsules, wherein each granule is 0.3 g.
Example 4: preparation of tablets
10 g of the compound urolithin compound obtained in example 1, 42 g of aerosil, 38 g of anhydrous lactose and 3 g of silicon oxide are mixed for 30 minutes, then 20 g of magnesium stearate is sieved, and the mixture is continuously mixed, and finally 12/32 of magnesium stearate is used
In inches.
Claims (6)
1. A urolithin compound having the formula:
urolithin compounds.
2. A medicament comprising one or more of the urolithin compounds described in claim 1, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.
3. Pharmaceutical according to claim 2, characterized in that it is in the form of capsules, granules, oral liquid or tablets.
4. Use of the urolithin derivative or combination thereof according to claim 2, in the manufacture of a medicament for the treatment or prevention of glioblastoma.
5. The medicament of claim 4, wherein the medicament is in the form of capsules, granules, oral liquid or tablets.
6. The use of the urolithin derivative or the composition thereof according to claim 2, in the manufacture of a medicament for treating glioblastoma.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910443193.0A CN111995610A (en) | 2019-05-27 | 2019-05-27 | Application of urolithin compound in medicine for treating glioblastoma |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910443193.0A CN111995610A (en) | 2019-05-27 | 2019-05-27 | Application of urolithin compound in medicine for treating glioblastoma |
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| Publication Number | Publication Date |
|---|---|
| CN111995610A true CN111995610A (en) | 2020-11-27 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN201910443193.0A Pending CN111995610A (en) | 2019-05-27 | 2019-05-27 | Application of urolithin compound in medicine for treating glioblastoma |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113730583A (en) * | 2021-08-27 | 2021-12-03 | 武汉大学 | Application of lipid droplets as drug targets of neurodegenerative diseases |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20090326057A1 (en) * | 2006-04-26 | 2009-12-31 | Seeram Navindra P | Therapeutic uses of urolithins |
| CN105142632A (en) * | 2012-06-27 | 2015-12-09 | 阿马曾提斯公司 | Enhancing autophagy or increasing longevity by administration of urolithins or precursors thereof |
| US20180125852A1 (en) * | 2015-05-08 | 2018-05-10 | Memorial Sloan Kettering Cancer Center | Compositions and methods for treatment of glioma |
| WO2018124135A1 (en) * | 2016-12-26 | 2018-07-05 | 株式会社ダイセル | Method for producing urolithins |
-
2019
- 2019-05-27 CN CN201910443193.0A patent/CN111995610A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20090326057A1 (en) * | 2006-04-26 | 2009-12-31 | Seeram Navindra P | Therapeutic uses of urolithins |
| CN105142632A (en) * | 2012-06-27 | 2015-12-09 | 阿马曾提斯公司 | Enhancing autophagy or increasing longevity by administration of urolithins or precursors thereof |
| US20180125852A1 (en) * | 2015-05-08 | 2018-05-10 | Memorial Sloan Kettering Cancer Center | Compositions and methods for treatment of glioma |
| WO2018124135A1 (en) * | 2016-12-26 | 2018-07-05 | 株式会社ダイセル | Method for producing urolithins |
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| Title |
|---|
| DONGLIANG WANG等: ""Ellagic acid inhibits human glioblastoma growth in vitro and in vivo"", 《ONCOLOGY REPORTS》 * |
| DONGLIANG WANG等: ""Ellagic acid inhibits human glioblastoma growth in vitro and in vivo"", 《ONCOLOGY REPORTS》, vol. 37, 22 December 2016 (2016-12-22), pages 1084 - 1092 * |
| WENHUA ZHAO等: "Preparative isolation and purification of urolithins from the intestinal metabolites of pomegranate ellagitannins by high-speed counter-current chromatography", JOURNAL OF CHROMATOGRAPHY B, vol. 990, pages 111 - 117 * |
| 尹培培等: "鞣花酸代谢产物――尿石素的研究进展", 《食品科学》 * |
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| 王丛丛等: "尿石素B对地塞米松诱导小鼠肌萎缩的改善作用及机制", 《中国老年学杂志》 * |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113730583A (en) * | 2021-08-27 | 2021-12-03 | 武汉大学 | Application of lipid droplets as drug targets of neurodegenerative diseases |
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