CN108379276B - Application of manno-glucuronic acid oligosaccharide in preparation of medicine for treating or preventing cancer - Google Patents
Application of manno-glucuronic acid oligosaccharide in preparation of medicine for treating or preventing cancer Download PDFInfo
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
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- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
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- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
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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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/702—Oligosaccharides, i.e. having three to five saccharide radicals attached to each other by glycosidic linkages
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/125—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives containing carbohydrate syrups; containing sugars; containing sugar alcohols; containing starch hydrolysates
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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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7016—Disaccharides, e.g. lactose, lactulose
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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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
- A61K31/736—Glucomannans or galactomannans, e.g. locust bean gum, guar gum
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- 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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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
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- Polymers & Plastics (AREA)
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Abstract
The invention relates to the application of manno-glucuronic acid oligosaccharide in preparing anticancer drugs and anticancer health products thereof; the mannoglucuronic acid oligosaccharide has obvious anticancer effect and can be used for preparing medicaments and health-care products for preventing and treating cancers.
Description
Technical Field
The invention belongs to the field of biomedicine, and relates to application of mannoglucuronic acid oligosaccharide in medicaments for preventing and treating cancers.
Background
Cancer is a serious health and life threatening disease in humans, with mortality second only to cardiovascular disease in terms of non-infectious diseases. According to the expectation of the world health organization, the global cancer incidence rate will increase by 50% by 2020, that is, 1500 ten thousand cancer patients are newly added each year, and 20% of new cancer patients in China are newly found in the world. The current methods for treating cancer in clinical use mainly comprise surgical treatment, radiotherapy, chemotherapy and the like. While these treatment strategies greatly improve the symptoms and quality of life of patients, the overall survival rate of patients remains low. Therefore, the need to find and develop novel and effective drugs for preventing and treating cancer remains urgent.
The oligosaccharide has multiple functions, such as the function of influencing the ecology and physiology of the intestinal tract of the organism, anticoagulation, anti-inflammation, the activity of improving the immunity of the organism and the like. To date, there is no application of mannoglucuronic acid oligosaccharides in preventive and anticancer drugs.
Disclosure of Invention
The invention provides an application of mannoglucuronic acid oligosaccharide in preparing a medicament for preventing or treating cancer.
The mannoglucuronic acid oligosaccharide has the following characteristics:
(1) sugar composition: mannose and glucuronic acid or salts thereof;
(2) 2-linked mannose and 4-linked glucuronic acid or a salt thereof are alternately linked;
the invention recommends that the structural formula of the mannoglucuronic acid oligosaccharide is one or two of a formula (I) or a formula (II);
in the formula (I), R1Is one or more than two of H, Na or K, n1Is an integer between 0 and 8 (n ═ 0, i.e. the recurring units are absent, and the radicals on both sides of the recurring units are linked to each other to form the compound);
in the formula (II), R2Is one or more than two of H, Na or K, n2Is an integer between 0 and 8 (n)20, i.e., the repeating unit is absent and the groups on both sides of the repeating unit are linked to each other to form the compound).
Preferably, the oligomannose glucuronide is one of the following compounds:
the mannoglucuronic acid oligosaccharide is used as a medicament for treating or preventing cancers, and the suitable cancer cells mainly comprise human leukemia cells K562, human breast cancer cells MCF-10, human liver cancer cells Huh7.5, human lung cancer cells A549 and the like.
Further, the application is as follows: the mannoglucuronic acid oligosaccharide and a pharmaceutically acceptable carrier and/or excipient are prepared into an injection, an oral preparation or a local administration preparation to be used as a medicine for treating or preventing cancers. Further, the carrier comprises sodium alginate microspheres, liposome and the like.
Further, the excipient is, for example, mannitol, magnesium stearate, starch, cyclodextrin, etc.
The preparation method of the oligomannose glucuronide can be referred to the method of the literature (Marine Drug,2012, 2138) -2152, and is detailed in example 1.
The invention has the following advantages: the mannoglucuronic acid oligosaccharide has the functions of preventing and treating cancers, has small toxic and side effects, is safe and effective, and can be used for preparing the medicines for treating and preventing the cancers.
Drawings
FIG. 1 gel chromatogram of alcohol eluate during oligosaccharide preparation;
FIG. 2 ESI-MS and HPLC plots of mannoglucuronosyl oligosaccharides G1-G4; a is G4; b is G3; c is G2; d is G1.
Detailed Description
The present invention will be specifically described below with reference to examples, but the present invention is not limited to the scope of the following examples.
EXAMPLE 1 preparation of oligomannose-glucuronide
Extracting dried herba Zosterae Marinae with 30 times of distilled water at 100 deg.C for 3 hr, filtering the extractive solution, concentrating, adding ethanol to obtain precipitate with final concentration of 75%, standing for 12 hr, collecting precipitate, and vacuum drying to obtain laminarin. Dissolving laminarin sample in sulfuric acid solution with mass concentration of 4% (material-liquid ratio is 60mg/mL), heating and refluxing for 5 hours, neutralizing with barium hydroxide until pH is 6-7, centrifuging, concentrating supernatant to one fifth of original volume, performing activated carbon column chromatography on concentrated solution, firstly balancing with distilled water, then performing gradient elution with 50% -90% ethanol, concentrating 50% -90% ethanol eluent to one fifth of original volume, evaporating ethanol, directly performing Bio-gel P4 column chromatography, separating to obtain five components (shown in figure 1), and performing ESI-MS and HPLC analysis (shown in figure 2) on the collected sample. As a result, the structure of the oligosaccharide was confirmed. The results show that G1-G4 are mannoglucuronoctaose, hexaose, tetrasaccharide and disaccharide, respectively. The structures of the compounds all accord with the structural formula shown in the following figure:
wherein G1 is mannoglucuronoctasaccharide, wherein n is1＝3，R1Is H or NH4 +；
G2 is Vitis viniferaUronic acid hexasaccharide of formula (I), wherein n1＝2，R1Is H or NH4 +；
G3 is mannoglucuronotetraose, wherein n is1＝1，R1Is H or NH4 +；
G4 is mannoglucuronbiose, wherein n is1＝0，R1Is H or NH4 +；
Example 2: effect of mannoglucuronic acid oligosaccharide in vitro on cancer cell proliferation activity
Effect of mannoglucuronic acid oligosaccharide in vitro administration on cancer cell proliferation Activity
MTT colorimetry is a method of detecting cell survival and growth. The detection principle is that succinate dehydrogenase in mitochondria of living cells can reduce exogenous MTT into water-insoluble blue-purple crystalline formazan and deposit the formazan in the cells, and dead cells do not have the function. Dimethyl sulfoxide can dissolve formazan in cells, and the absorbance of formazan at 490nm wavelength is measured by a microplate reader, which can indirectly reflect the number of living cells. Within a certain range of cell number, MTT crystals are formed in an amount proportional to the cell number. The method is widely used for activity detection of some bioactive factors, large-scale anticancer drug screening, cytotoxicity test, tumor radiosensitivity test and the like. It features high sensitivity and economy.
Experimental methods
Collecting cancer cells (human liver cancer cell Huh7.5, human lung cancer cell A549) in logarithmic growth phase, digesting with trypsin to obtain (or blowing) single cell suspension, counting, and processing according to 1 × 104The density of each well is inoculated on a 96-well cell culture plate, and 5% CO is put in2Culturing in a cell culture box at 37 ℃; adding samples to be detected with different final concentrations into a 96-well plate the next day, setting 3 multiple wells for each group of concentration, and putting into an incubator to continue culturing for 24 hours; after sample treatment, adding 10 mul of MTT solution (the concentration is 5mg/ml) into each hole, putting the MTT solution into an incubator, then culturing for 4h, pouring out culture supernatant in a 96-hole plate, adding 100 mul of dimethyl sulfoxide into each hole, oscillating on a shaking table for 10min, uniformly mixing, and measuring the light absorption value at 490nm by using an enzyme-labeling instrument; push buttonThe inhibition rate of proliferation of cancer cells was calculated as follows: the proliferation inhibition ratio (%) was (OD control group — OD experimental group)/OD control group × 100%. The experiment was repeated five times, data to
And (4) showing.
The mannoglucuronosyl oligosaccharides prepared in example 1 had an inhibitory effect on the proliferation activity of cancer cells in vitro, and the results are shown in table 1. The mannoglucuronic acid oligosaccharides inhibit the in vitro proliferative activity of different cancer cells in a concentration-dependent manner. Of these, the activity of G4 was most pronounced.
TABLE 1 IC of sulfated mannoglucuronosyl acid oligosaccharides on cancer cells50
Claims (3)
1. Use of mannoglucuronic acid oligosaccharide in preparation of medicine for treating or preventing cancer; the structural formula of the mannoglucuronic acid oligosaccharide is one or two of a formula (I) or a formula (II);
in the formula (I), R1Is one or more than two of H, Na or K, n1Is an integer between 0 and 8;
in the formula (II), R2Is one or more than two of H, Na or K, n2Is an integer between 0 and 8;
the cancer cell is human liver cancer cell Huh7.5 or human lung cancer cell A549.
2. Use according to claim 1, characterized in that the oligomannoglucuronic acid is one of the following compounds:
3. the application according to claim 1, characterized in that the application is: the medicament for treating or preventing cancer is prepared by mixing the mannoglucuronic acid oligosaccharide and a pharmaceutically acceptable carrier and/or excipient to prepare an injection, an oral preparation or a local administration preparation.
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| Title |
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| The structure-activity relationship between polysaccharides from;Weihua Jin等;《International Journal of Biological Macromolecules》;20170715;第105卷;686-692 * |
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