CN117018000B - Application of 4-cholestene-3-one in preparing medicine for preventing or treating inflammatory bowel disease - Google Patents
Application of 4-cholestene-3-one in preparing medicine for preventing or treating inflammatory bowel disease Download PDFInfo
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- 208000022559 Inflammatory bowel disease Diseases 0.000 title claims abstract description 39
- 239000003814 drug Substances 0.000 title claims abstract description 28
- NYOXRYYXRWJDKP-GYKMGIIDSA-N cholest-4-en-3-one Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 NYOXRYYXRWJDKP-GYKMGIIDSA-N 0.000 title claims abstract description 23
- NYOXRYYXRWJDKP-UHFFFAOYSA-N cholestenone Natural products C1CC2=CC(=O)CCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 NYOXRYYXRWJDKP-UHFFFAOYSA-N 0.000 claims abstract description 19
- 229940079593 drug Drugs 0.000 claims abstract description 13
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 4
- 208000011231 Crohn disease Diseases 0.000 claims description 4
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 4
- 239000000725 suspension Substances 0.000 claims description 4
- 239000002552 dosage form Substances 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 2
- 241000699670 Mus sp. Species 0.000 abstract description 22
- 210000001072 colon Anatomy 0.000 abstract description 13
- 230000000694 effects Effects 0.000 abstract description 13
- 230000002550 fecal effect Effects 0.000 abstract description 9
- 230000009266 disease activity Effects 0.000 abstract description 8
- 238000011282 treatment Methods 0.000 abstract description 8
- TVZRAEYQIKYCPH-UHFFFAOYSA-N 3-(trimethylsilyl)propane-1-sulfonic acid Chemical compound C[Si](C)(C)CCCS(O)(=O)=O TVZRAEYQIKYCPH-UHFFFAOYSA-N 0.000 abstract description 7
- 208000032843 Hemorrhage Diseases 0.000 abstract description 7
- 208000031648 Body Weight Changes Diseases 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- 230000004579 body weight change Effects 0.000 abstract 1
- 229960000633 dextran sulfate Drugs 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 208000002551 irritable bowel syndrome Diseases 0.000 description 18
- 229920003045 dextran sodium sulfate Polymers 0.000 description 9
- 206010009887 colitis Diseases 0.000 description 8
- 230000037396 body weight Effects 0.000 description 6
- 230000000740 bleeding effect Effects 0.000 description 5
- 102100039497 Choline transporter-like protein 3 Human genes 0.000 description 4
- 206010012735 Diarrhoea Diseases 0.000 description 4
- 101000889279 Homo sapiens Choline transporter-like protein 3 Proteins 0.000 description 4
- 239000008280 blood Substances 0.000 description 4
- 210000004369 blood Anatomy 0.000 description 4
- KBOPZPXVLCULAV-UHFFFAOYSA-N mesalamine Chemical compound NC1=CC=C(O)C(C(O)=O)=C1 KBOPZPXVLCULAV-UHFFFAOYSA-N 0.000 description 4
- 208000024891 symptom Diseases 0.000 description 4
- 208000016261 weight loss Diseases 0.000 description 4
- 230000004580 weight loss Effects 0.000 description 4
- 229960004963 mesalazine Drugs 0.000 description 3
- 238000010172 mouse model Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- BLFLLBZGZJTVJG-UHFFFAOYSA-N benzocaine Chemical compound CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000008213 purified water Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 1
- 238000011740 C57BL/6 mouse Methods 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 208000004232 Enteritis Diseases 0.000 description 1
- UETNIIAIRMUTSM-UHFFFAOYSA-N Jacareubin Natural products CC1(C)OC2=CC3Oc4c(O)c(O)ccc4C(=O)C3C(=C2C=C1)O UETNIIAIRMUTSM-UHFFFAOYSA-N 0.000 description 1
- 206010038063 Rectal haemorrhage Diseases 0.000 description 1
- 238000000692 Student's t-test Methods 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 230000003044 adaptive effect Effects 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000003266 anti-allergic effect Effects 0.000 description 1
- 230000002924 anti-infective effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 230000036765 blood level Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000002354 daily effect Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 230000001200 fecal consistency Effects 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 239000003862 glucocorticoid Substances 0.000 description 1
- 244000005709 gut microbiome Species 0.000 description 1
- 208000026278 immune system disease Diseases 0.000 description 1
- 239000002955 immunomodulating agent Substances 0.000 description 1
- 229940121354 immunomodulator Drugs 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 230000003780 keratinization Effects 0.000 description 1
- 230000037356 lipid metabolism Effects 0.000 description 1
- 208000019423 liver disease Diseases 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 235000000891 standard diet Nutrition 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- -1 steroid compound Chemical class 0.000 description 1
- 239000003270 steroid hormone Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- NCEXYHBECQHGNR-QZQOTICOSA-N sulfasalazine Chemical compound C1=C(O)C(C(=O)O)=CC(\N=N\C=2C=CC(=CC=2)S(=O)(=O)NC=2N=CC=CC=2)=C1 NCEXYHBECQHGNR-QZQOTICOSA-N 0.000 description 1
- 229960001940 sulfasalazine Drugs 0.000 description 1
- NCEXYHBECQHGNR-UHFFFAOYSA-N sulfasalazine Natural products C1=C(O)C(C(=O)O)=CC(N=NC=2C=CC(=CC=2)S(=O)(=O)NC=2N=CC=CC=2)=C1 NCEXYHBECQHGNR-UHFFFAOYSA-N 0.000 description 1
- 229940037128 systemic glucocorticoids Drugs 0.000 description 1
- 238000012353 t test Methods 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000011285 therapeutic regimen Methods 0.000 description 1
Classifications
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- 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
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/575—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of three or more carbon atoms, e.g. cholane, cholestane, ergosterol, sitosterol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention discloses application of 4-cholesten-3-one in preparing medicines for preventing or treating inflammatory bowel disease. The effect of 4-cholesten-3-one on mice body weight changes, fecal viscosity and fecal hemorrhage, disease Activity Index (DAI), and colon length was calculated by modeling sodium dextran sulfate (DSS) induced Inflammatory Bowel Disease (IBD) mice. The result shows that 4-cholesten-3-one has remarkable treatment effect on DSS induced colonitis, and provides a new medicament for clinically treating IBD.
Description
Technical Field
The invention relates to the technical field of medicines, in particular to application of 4-cholesten-3-one in preparing medicines for preventing or treating inflammatory bowel diseases.
Background
Inflammatory bowel disease (Inflammatory Bowel Disease, IBD) is a chronic, non-specific, inflammatory bowel disease caused mainly by the gut microbiota and immune system disorders, including Crohn's Disease (CD) and ulcerative colitis (ulcerative colitis, UC). The current treatments for IBD rely primarily on traditional therapeutic agents including 5-aminosalicylic acid, glucocorticoids, immunomodulators, and the like. Traditional drugs have poor control efficacy for partially moderately severe patients and have serious side effects. Thus, finding a positive and effective therapeutic regimen for IBD is a clinical problem that needs to be addressed urgently.
The steroid compound is used as a second large class of medicine next to antibiotics, plays an important role in medicine, is widely used for treating cardiovascular diseases, anti-tumor, anti-infection, anti-allergy and the like, and 4-cholesten-3-one is a precondition substance of a series of steroid hormone medicines, is a metabolic intermediate product of intestinal bacteria, participates in lipid metabolism, can be directly used as a medicine, has a certain health care function and potential medicinal value, and can be used for inhibiting fat accumulation in human bodies, treating liver diseases and preventing skin keratinization. However, no report on the preparation of medicines for preventing or treating inflammatory bowel disease by using 4-cholesten-3-one is currently known.
Disclosure of Invention
In view of the above, the present invention aims to provide an application of 4-cholesten-3-one in preparing a medicament for preventing or treating inflammatory bowel disease, and to provide a novel medicament for treating inflammatory bowel disease clinically.
Inflammatory bowel disease (Inflammatory bowel disease, IBD) as described herein includes ulcerative colitis and crohn's disease.
The 4-cholesten-3-one can be used in combination with other medicines for preventing and treating inflammatory bowel diseases, and can also be used as the only active ingredient.
The invention detects the weight change, the fecal viscosity and the fecal hemorrhage of mice by inducing an IBD mouse model by dextran sodium sulfate (Dextran Sulfate Sodium, DSS), calculates the disease activity Index (DISEASE ACTIVITY Index, DAI), and observes the influence of 4-cholesten-3-one (4 CTL 3) on the colon length of the mice. The results show that the 4-cholesten-3-one has no obvious reversal effect on the weight loss caused by the enteritis, the DAI is calculated by observing the viscosity and the bleeding condition of the feces of the mice every day, the DAI score of a model group is found to be obviously higher than that of a 4CTL3 group, and the colon length of the mice is measured, and the 4CTL3 is found to obviously prolong the colon length of the IBD mice. The results show that 4-cholesten-3-one (4 CTL 3) has remarkable treatment effect on DSS induced colonitis and can obviously improve IBD symptoms.
The medicine contains effective content of 4-cholesten-3-one and pharmaceutically acceptable carrier. The medicine for preventing or treating inflammatory bowel disease can be prepared into a proper dosage form by a conventional method in the field. The pharmaceutically acceptable carrier is selected from pharmaceutically acceptable suspensions. The medicament may thereby be formulated in a form suitable for administration of a clinical pharmaceutical formulation.
Preferably, the dosage form of the medicament is a suspension.
Compared with the prior art, the invention has the following excellent effects:
The invention provides a new application of 4-cholesten-3-one in preparing medicines for preventing or treating inflammatory bowel diseases, and the result shows that 4-cholesten-3-one has remarkable treatment effect on colitis induced by DSS by establishing a dextran sodium sulfate (Dextran Sulfate Sodium, DSS) induced IBD mouse model, can obviously improve IBD symptoms, and provides a new medicine for clinically treating IBD.
Drawings
FIG. 1 shows the effect of 4CTL3 on the weight of mice with colon inflammation, *** P <0.001 (model group VS blank group), ### P <0.001 (4 CTL3 group VS model group).
FIG. 2 shows the effect of 4CTL3 on the disease activity index of mice with colitis, *** P <0.001 (model group vs blank group), ## P <0.01 (4 CTL3 group vs model group).
FIG. 3 shows the effect of 4CTL3 on colon length in colon inflammatory mice, *** P <0.001 (model VS blank), ##P<0.01,### P <0.001 (5-ASA, 4CTL3 VS model).
Detailed Description
The present invention will be further illustrated by the following examples, which are not intended to limit the scope of the invention.
EXAMPLE 1 therapeutic Effect of 4-cholesten-3-one on mouse IBD
1. Materials and methods
1.1 Medicaments
(+) -4-Cholesten-3-one (4 CTL 3) was purchased from sigma (CAS: 601-57-0), prepared as a suspension using 5% CMCNA, and sulfasalazine (lot: J2212276) was purchased from Shanghai Ala Biochemical technologies Co. Dextran sodium sulfate was purchased from MP Biomedicals (lot: S7980).
1.2 Instruments
MTB1000D electronic balance (Shenzhen Mobil electronic Co., ltd.)
1.3 Animals
C57BL/6 mice (purchased from medical laboratory animal center, guangdong province, license number SCXK (Yue) 2022-0002 Yue license 2006A 018) were male, and had a body weight of 19-21g. Mice were kept in the university of medical science laboratory animal center, guangdong, 12 hours light/dark, free diet.
1.4 Method
After 7 days of adaptive feeding (24-25 ℃ C., humidity 70-75%,12 hours light/dark) with standard diet and water, the mice were randomly divided into 4 groups of 6 animals each, including control group, model group, 5-ASA group (200 mg/kg), 4CTL3 group (50 mg/kg). The 4CTL3 group was prophylactically orally administered for 5 days, the model group was continuously orally administered purified water for 5 days (from day 0 to day 5), mice were free to drink 2.5% dss at day 5, and the blank group was continuously administered purified water for 7 days (from day 5 to day 12). Mice were observed daily and recorded for body weight, fecal consistency, and fecal bleeding. On day 12, anesthetized mice were sacrificed after blood collection. The length was measured from colon tissue of the mice.
According to the Disease Activity Index (DAI), the disease activity index score (no loss record 0 score, 1% -5% loss record 1 score, 5% -10% loss record 2 score, 10% -5% loss record 3 score, and more than 15% loss record 4 score) is determined according to the weight loss condition, the fecal viscosity (normal stool score 0 score, soft stool score 1 score, thin wet stool score 2 score, diarrhea dry stool score 3 score, diarrhea wet stool score 4 score) and the fecal bleeding (no blood record 0 score, slight blood record 1 score, occult blood record 2 score, bleeding record less than 3 score and major bleeding record 4 score) of the IBD mice are determined. DAI calculation dai= (weight loss score + fecal viscosity score + fecal blood level score)/3
1.5 Statistical methods
The results were analyzed using Graphpad prism7.0 statistical analysis software. Each set of data x- ±sd represents that the sample-to-sample comparison uses a t-test.
2. Results
2.1 Effect of 4CTL3 on IBD mouse body weight
Experimental results indicate that 4CTL3 had no significant effect on the body weight caused by IBD, and that 4CTL3 group had significant differences (P < 0.001) compared to the body weight of the model group, and that the model group had significant differences (P < 0.001) compared to the body weight of the blank group. The results are shown in Table 1 and FIG. 1.
Table 1.4CTL3 influence on the weight of mice with colon inflammation (x- + -SD N=6)
*** P <0.001 (model VS blank), ### P <0.001 (4 CTL3 VS model).
2.2 Influence of 4CTL3 on the disease Activity index of mice with colon inflammation
After 4CTL3 treatment, the IBD mice had significantly reduced diarrhea, rectal bleeding and weight loss symptoms and significantly reduced DAI scores. The 4CTL3 group had significant differences (P < 0.01) compared to the model group DAI, the 4CTL3 group DAI values were significantly lower than the model group, and the model group had significant differences (P < 0.010) compared to the blank group DAI. The results are shown in Table 2 and FIG. 2.
Table 2.4CTL3 influence on the disease Activity index of mice with colon inflammation (x- + -SD N=6)
*** P <0.001 (model group vs blank group), ## P <0.01 (4 CTL3 group vs model group).
2.3 Effect of 4CTL3 treatment on colon length
The colon length was significantly shortened in the model group compared to the blank group (P < 0.001), whereas the colon length shortening was significantly reversed 12 days after 4CTL3 treatment, and the 4CTL3 group was significantly different from the model group colon length (P < 0.001). The results are shown in Table 3 and FIG. 3.
Table 3.4CTL3 Effect on colon length in mice with colon inflammation (x- + -SD N=6)
*** P <0.001 (model VS blank), ##P<0.01,### P <0.001 (5-ASA, 4CTL3 VS model).
In conclusion, by establishing a dextran sodium sulfate induced IBD mouse model, the 4CTL3 group is significantly different from the model group in terms of DAI score and colon length 2 index evaluation, so that the conclusion can be drawn that the 4CTL3 has significant therapeutic effect on DSS induced colitis, can significantly improve IBD symptoms, and provides a new medicament for clinical treatment of IBD.
Claims (5)
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| CN102083849A (en) * | 2008-07-30 | 2011-06-01 | 特罗福斯公司 | Novel cholest-4-en-3-one oxime derivatives, pharmaceutical compositions containing same, and preparation method |
| EP3777865A1 (en) * | 2018-03-29 | 2021-02-17 | Morinaga Milk Industry Co., Ltd. | Anti-aging composition |
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| DE69818673T2 (en) * | 1997-07-17 | 2004-08-05 | F. Hoffmann-La Roche Ag | DIHOMO-SECO-CHOLESTAN COMPOUNDS WITH TWO UNSATURATED BINDINGS IN THE SIDE CHAIN |
| US6998392B2 (en) * | 2003-04-02 | 2006-02-14 | Mti Meta Tech Inc. | Formulation to treat or prevent parasitic infection |
| CN101484001A (en) * | 2006-04-07 | 2009-07-15 | 顺天生物科技股份有限公司 | Anthracene dione compound |
| WO2010045180A1 (en) * | 2008-10-13 | 2010-04-22 | Metabolon, Inc. | Biomarkers for inflammatory bowel disease and methods using the same |
| WO2018011691A1 (en) * | 2016-07-12 | 2018-01-18 | Nestec S.A. | Competitive immunoassay methods |
| CN120732855A (en) * | 2020-03-18 | 2025-10-03 | 伊莱利利公司 | Fanisolide X receptor agonists for the treatment of disease |
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| CN102083849A (en) * | 2008-07-30 | 2011-06-01 | 特罗福斯公司 | Novel cholest-4-en-3-one oxime derivatives, pharmaceutical compositions containing same, and preparation method |
| EP3777865A1 (en) * | 2018-03-29 | 2021-02-17 | Morinaga Milk Industry Co., Ltd. | Anti-aging composition |
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