CN109674805A - Application of the benzyl carbinol glycoside compound in the drug for promoting periodontosis Bone Defect Repari - Google Patents

Application of the benzyl carbinol glycoside compound in the drug for promoting periodontosis Bone Defect Repari Download PDF

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Publication number
CN109674805A
CN109674805A CN201910111212.XA CN201910111212A CN109674805A CN 109674805 A CN109674805 A CN 109674805A CN 201910111212 A CN201910111212 A CN 201910111212A CN 109674805 A CN109674805 A CN 109674805A
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cistantubuloside
drug
periodontosis
benzyl carbinol
glycoside compound
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张静莹
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Dalian University
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Dalian University
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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
    • A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
    • A61K31/7032—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a polyol, i.e. compounds having two or more free or esterified hydroxy groups, including the hydroxy group involved in the glycosidic linkage, e.g. monoglucosyldiacylglycerides, lactobionic acid, gangliosides
    • 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
    • A61K31/716—Glucans
    • A61K31/722—Chitin, chitosan
    • 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
    • A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth 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)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Molecular Biology (AREA)
  • Epidemiology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Rheumatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention belongs to drug field, application of the specific benzyl carbinol glycoside compound in the drug for promoting periodontosis Bone Defect Repari.The present invention provides the new applications of benzyl carbinol glycoside compound, benzyl carbinol glycoside compound is applied in the drug of the treatment and prevention of periodontosis, it is able to suppress periodontal inflammatory absorption of alveolar bone, promotes osteoblast differentiation, it can promote the relevant Bone Defect Repari of periodontosis, it is shared with chitosan, effect is more excellent.

Description

Application of the benzyl carbinol glycoside compound in the drug for promoting periodontosis Bone Defect Repari
Technical field
The invention belongs to drug field, specific benzyl carbinol glycoside compound answering in the drug for promoting periodontosis Bone Defect Repari With.
Background technique
Periodontosis refers to that one kind betides the one chronic of periodontium (including gum, parodontium, alveolar bone, cementum etc.) Diseases associated with inflammation.Periodontosis is not only the clinical member for causing the oral problems such as periodontal abscess, bleeding gums, gingival atrophy, halitosis One of act of violence can also cause the degradation of periodontium, the absorption of alveolar bone, and eventually lead to the loosening of tooth or even fall off, wherein The destruction of periodontium and absorption of alveolar bone are the typical clinical pathological changes of periodontosis.
For periodontosis, clinic spininess is to its pathogenic factor at present, and use is anti-inflammatory, Dental Erosion, the methods of root canal treatment, Can alleviate the development of periodontosis to a certain extent, postpone absorption of alveolar bone, thus avoid to a certain extent tooth mobility and It falls off, but current treatment method effect is single, works slow, needs operative treatment, at high cost, patient compliance is poor, and is difficult to The absorption of alveolar bone generated is reversed, therefore, the treatment of absorption of alveolar bone caused by periodontosis, especially periodontosis is imitated Fruit is still undesirable.
Benzyl carbinol glycoside compound is that this kind of acrylic acid and benzyl carbinol part pass through ester bond and glycosidic bond and β-pyrrole respectively The compound formed after glucopyranoside connection, can specifically be divided into:
(1) position C-3 ' of glucose is by the sugar-substituted benzyl carbinol glycosides of α-L- sandlwood, such as:
(2) position C-3 ' of glucose is unsubstituted or by the sugar-substituted benzyl carbinol glycosides other than α-L- rhamnose, such as:
(3) benzyl carbinol glycosides of the C-7 substd of benzyl carbinol base, such as:
(4) containing Isosorbide-5-Nitrae-dioxy hexatomic ring benzyl carbinol glycosides, such as:
(5) benzyl carbinol glycosides containing iridoid base, such as:
(6) glucose is connected to the benzyl carbinol glycosides of -4 hydroxyl of phenethyl, such as:
(7) core sugar is the benzyl carbinol glycosides of the glycosyl other than glucose, such as:
It has been reported that benzyl carbinol glycoside compound is active with multi-biological, including antitumor, antiviral, antibacterial, anti-inflammatory, Liver protecting, anti-oxidant, immunological regulation, neuroprotection etc., but benzyl carbinol glycoside compound is used for periodontosis, especially promotes tooth The purposes of all disease Bone Defect Reparis has not been reported.
Summary of the invention
The object of the present invention is to provide application of the benzyl carbinol glycoside compound in the drug for promoting periodontosis Bone Defect Repari.
For achieving the above object, the invention adopts the following technical scheme:
On the one hand, application of the benzyl carbinol glycoside compound in the drug for promoting periodontosis Bone Defect Repari.
In above-mentioned application, the benzyl carbinol glycoside compound is had the following structure:
Wherein, R1, R2 are independent is selected from hydrogen or glycosyl；R3, R5 are independent to be selected from hydrogen or hydroxyl；R4 is selected from hydrogen, acetyl group Or glycosyl.
Optionally, the glycosyl is selected from: glucopyranosyl, α-L- rhamnopyranosyl, galactosyl.
Optionally, the benzyl carbinol glycoside compound is selected from: Cistantubuloside A, Cistantubuloside B1, pipe flower meat desert The one or more of Rong's glycosides B2, Cistantubuloside C1, Cistantubuloside C2.
On the other hand, the composition of benzyl carbinol glycoside compound and chitosan promotes the drug of periodontosis Bone Defect Repari in preparation Application in composition.
Optionally, the chitosan is selected from: carboxymethyl chitosan.
Compared with prior art, the invention has the benefit that the present invention provides the new use of benzyl carbinol glycoside compound On the way, benzyl carbinol glycoside compound is applied in the drug for the treatment of and prevention of periodontosis, is able to suppress periodontal inflammatory alveolar bone It absorbs, promote osteoblast differentiation, can promote the relevant Bone Defect Repari of periodontosis, shared with chitosan, effect is more excellent.
Specific embodiment
Below in conjunction with specific embodiment, the present invention will be further described.
A kind of gelling agent for promoting periodontosis Bone Defect Repari of embodiment 1
6 parts of Cistantubuloside B2,11 parts of carboxymethyl chitosan, 50 parts of aqua sterilisa, 1 part of corrigent, in accordance with the following methods Preparation:
(1) it crushes: being uniformly mixed to obtain mixing after Cistantubuloside B2, carboxymethyl chitosan crushed 40 meshes respectively Powder, it is spare；
(2) preparation: stirring evenly after corrigent and aqua sterilisa is added in mixed powder, sufficiently dispenses after swelling up to this hair The bright gelling agent for promoting periodontosis Bone Defect Repari.
A kind of gelling agent for promoting periodontosis Bone Defect Repari of embodiment 2-6
Component Embodiment 2 Embodiment 3 Embodiment 4 Embodiment 5 Embodiment 6
Cistantubuloside B2 8.5 2
Cistantubuloside A 6
Cistantubuloside B1 6
Cistantubuloside C1 6
Cistantubuloside C2
Carboxymethyl chitosan 8.5 15 11 11 11
Corrigent 1 1 1 1 1
Aqua sterilisa 50 50 50 50 50
According to the gelling agent of promotion periodontosis Bone Defect Repari described in 1 the method for embodiment preparation embodiment 2-6.
Influence of the 1 benzyl carbinol glycoside compound of effect example to proliferation of rat osteoblasts
1.1 experimental drugs:
Cistantubuloside A, Cistantubuloside B1, Cistantubuloside B2, Cistantubuloside C1, Cistanche tubulosa Glycosides C2, the liquid for being configured to 0.25g/L using sterile PBS solution are spare.
1.2 experimental method
(1) it takes cranium: taking newborn SD rat cranium under aseptic condition, reject the connective adhered on rat calvarial bone Tissue and blood vessel are rinsed 5 times using sterile PBS solution, are shredded using sterilizing operating scissors；
(2) remove fibroblast: the trypsase that 3g/L is added in the rat calvarial bone after shredding digests at 37 DEG C 15min is rinsed 3 times after absorbing digestive juice using sterile PBS；
(3) collagenase type I for the 1.5g/L that volume ratio is 1:1 and the hyaluronic acid of 1g/L the digestion of osteoblast: is added Enzyme, digests 20min at 37 DEG C, and digestive juice is sucked out spare, and sufficiently digestion 5 times collects the 3-5 time digestive juice, is centrifuged, discards Clearly, it is centrifuged, discards supernatant after being rinsed using the DMEM culture medium without serum, the DMEM culture medium for containing 10% fetal calf serum is added Piping and druming is uniform, with 3 × 105Acquired cell inoculation in Tissue Culture Flask, is placed in 37 DEG C, 5%CO by the concentration of/mL2Culture In case, every 48h is changed liquid 1 time, after cell fusion, using passing on after the trypsin digestion of 2.5g/L.The 3rd generation cell is taken, with 3 ×104The density of/mL is inoculated in 96 orifice plates, and the DMEM culture medium for containing 10% fetal calf serum is added, and every 100 μ L of hole will be inoculated with Cell is divided into blank group, experiment 1-5 group, every group of 3 repeating holes, and inoculation sucks supernatant after 24 hours, rejoins containing 10% The DMEM culture medium of fetal calf serum, every 90 μ L of hole are added by group and blow and beat uniform experimental drug, every 10 μ L of hole, wherein blank Sterile PBS solution is added in group, continues to cultivate 48h, and the MTT solution of 5g/L is then added, and every 20 μ L of hole continues to cultivate 4h, suck DMSO, every 150 μ L of hole are added after culture solution, uses microplate reader after shaking 5min, detects the absorbance of 570nm, calculate each experiment Drug the results are shown in Table 1 to the promotion rate of osteoblastic proliferation, specific experiment, in which:
Promotion rate (%)=(experimental group absorbance-blank group absorbance)/blank group absorbance × 100%.
1.3 experimental result
The multifactor analysis of variance module of applied statistics software SPSS carries out data analysis, wherein indicating poor as P < 0.05 It is different statistically significant.
Influence of the 1 benzyl carbinol glycoside compound of table to proliferation of rat osteoblasts
Group Absorbance Promotion rate (%)
Blank group 0.596±0.047
Cistantubuloside A 0.675±0.068* 13.26%
Cistantubuloside B1 0.742±0.054* 24.50%
Cistantubuloside B2 0.839±0.076** 40.77%
Cistantubuloside C1 0.663±0.051* 11.24%
Cistantubuloside C2 0.724±0.065* 21.48%
Compared with blank group, P < 0.01 * P < 0.05, * *.
1 experimental result of table shows Cistantubuloside A, Cistantubuloside B1, Cistantubuloside B2, pipe flower meat desert Rong's glycosides C1 and Cistantubuloside C2 show the facilitation to proliferation of rat osteoblasts, wherein especially with pipe flower meat desert The effect of Rong's glycosides B1, Cistantubuloside B2 and Cistantubuloside C2 are more excellent, more specifically with Cistantubuloside B2 Effect it is the most excellent, the promotion rate relative to blank group has been more than 40%, it is shown that benzyl carbinol glycoside compound is especially managed Flower herba cistanches glycosides B2 has the effect of significantly promoting proliferation of rat osteoblasts.
Effect example 2: influence of the combination of Cistantubuloside B2 and carboxymethyl chitosan to proliferation of rat osteoblasts
2.1 experimental drug
The liquid that following experimental drug is configured to 0.25g/L using sterile PBS solution is spare.
2 experimental drug of table
Group Experimental drug
Drug 1 Cistantubuloside B2
Drug 2 Carboxymethyl chitosan
Drug 3 Cistantubuloside B2: carboxymethyl chitosan=6: 1
Drug 4 Cistantubuloside B2: carboxymethyl chitosan=6: 2
Drug 5 Cistantubuloside B2: carboxymethyl chitosan=6: 4
Drug 6 Cistantubuloside B2: carboxymethyl chitosan=6: 6
Drug 7 Cistantubuloside B2: carboxymethyl chitosan=6: 8
Drug 8 Cistantubuloside B2: carboxymethyl chitosan=6: 9
Drug 9 Cistantubuloside B2: carboxymethyl chitosan=6: 10
Drug 10 Cistantubuloside B2: carboxymethyl chitosan=6: 11
Drug 11 Cistantubuloside B2: carboxymethyl chitosan=6: 12
Drug 12 Cistantubuloside B2: carboxymethyl chitosan=6: 13
Drug 13 Cistantubuloside B2: carboxymethyl chitosan=6: 16
Drug 14 Cistantubuloside B2: carboxymethyl chitosan=6: 20
2.2 experimental method
According to 1 the method for embodiment, each experimental drug is measured to the promotion rate of rat osteoblast, specific experiment result It is shown in Table 3.
2.3 experimental result
The multifactor analysis of variance module of applied statistics software SPSS carries out data analysis, wherein indicating poor as P < 0.05 It is different statistically significant.
3 experimental result of table shows that individual carboxymethyl chitosan does not simultaneously have the shadow for promoting proliferation of rat osteoblasts It rings, it is bright that the ratio of Cistantubuloside B2 and carboxymethyl chitosan combination promotes it effect of proliferation of rat osteoblasts to have Aobvious influence, and three phases can be greatly classified into: the first stage: when Cistantubuloside B2 content is more than carboxymethyl chitosan When, with the increase of carboxymethyl chitosan sugared content, composition promotes the effect of proliferation of rat osteoblasts to gradually decrease；Second-order Section: when Cistantubuloside B2 content is less than carboxymethyl chitosan, and Cistantubuloside B2: carboxymethyl chitosan is greater than or waits When 6: 11, composition promotes the effect of proliferation of rat osteoblasts to gradually increase, and works as Cistantubuloside B2: carboxymethyl chitosan When sugar=6: 11, composition has the effect of significantly promoting proliferation of rat osteoblasts, and the effect is better than the colored meat of independent pipe The effect of desert cistanche glycosides B2, it is shown that Cistantubuloside B2: carboxymethyl chitosan=6: when 11, with synergy promotion rat at The effect of bone cell proliferation；Phase III: when Cistantubuloside B2: when carboxymethyl chitosan is less than 6: 11, composition promotes The effect of proliferation of rat osteoblasts gradually decreases, when Cistantubuloside B2: carboxymethyl chitosan=6: when 20, composition is several Do not have the effect for promoting rat skeletonization proliferation.
Influence of the combination of 3 Cistantubuloside B2 of table and carboxymethyl chitosan to proliferation of rat osteoblasts
Group Trial drug Absorbance Promotion rate (%)
Blank group 0.531±0.044
Drug 1 Cistantubuloside B2 0.725±0.057** 36.53%
Drug 2 Carboxymethyl chitosan 0.486±0.061 - 8.47%
Drug 3 Cistantubuloside B2: carboxymethyl chitosan=6: 1 0.659±0.068* 24.11%
Drug 4 Cistantubuloside B2: carboxymethyl chitosan=6: 2 0.592±0.053 11.49%
Drug 5 Cistantubuloside B2: carboxymethyl chitosan=6: 4 0.617±0.066* 16.20%
Drug 6 Cistantubuloside B2: carboxymethyl chitosan=6: 6 0.580±0.076 9.23%
Drug 7 Cistantubuloside B2: carboxymethyl chitosan=6: 8 0.629±0.054* 18.46%
Drug 8 Cistantubuloside B2: carboxymethyl chitosan=6: 9 0.658±0.069* 23.92%
Drug 9 Cistantubuloside B2: carboxymethyl chitosan=6: 10 0.714±0.081** 34.46%
Drug 10 Cistantubuloside B2: carboxymethyl chitosan=6: 11 0.787±0.079** 48.21%
Drug 11 Cistantubuloside B2: carboxymethyl chitosan=6: 12 0.705±0.094** 32.77%
Drug 12 Cistantubuloside B2: carboxymethyl chitosan=6: 13 0.673±0.061* 26.74%
Drug 13 Cistantubuloside B2: carboxymethyl chitosan=6: 16 0.624±0.048* 17.51%
Drug 14 Cistantubuloside B2: carboxymethyl chitosan=6: 20 0.539±0.053 1.51%
Compared with blank group, P < 0.01 * P < 0.05, * *.
The foregoing describe the preferred embodiment for the present invention, and however, it is not to limit the invention.Those skilled in the art couple Embodiment disclosed herein can carry out the improvements and changes without departing from scope and spirit.

Claims (6)

1. application of the benzyl carbinol glycoside compound in the drug for promoting periodontosis Bone Defect Repari.
2. application as described in claim 1, which is characterized in that the benzyl carbinol glycoside compound has the following structure:
Wherein, R1, R2 are independent is selected from hydrogen or glycosyl；R3, R5 are independent to be selected from hydrogen or hydroxyl；R4 is selected from hydrogen, acetyl group or sugar Base.
3. application as claimed in claim 2, which is characterized in that the glycosyl is selected from: glucopyranosyl, α-L- rhamnose Base, galactosyl.
4. application as claimed in claim 1 or 2, which is characterized in that the benzyl carbinol glycoside compound is selected from: Cistanche tubulosa The one or more of glycosides A, Cistantubuloside B1, Cistantubuloside B2, Cistantubuloside C1, Cistantubuloside C2.
5. the composition of benzyl carbinol glycoside compound and chitosan is in the pharmaceutical composition that preparation promotes periodontosis Bone Defect Repari Using.
6. application as claimed in claim 2, which is characterized in that the chitosan is selected from: carboxymethyl chitosan.
CN201910111212.XA 2019-02-12 2019-02-12 Application of the benzyl carbinol glycoside compound in the drug for promoting periodontosis Bone Defect Repari Pending CN109674805A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112604672A (en) * 2020-12-01 2021-04-06 石河子大学 Functionalized carboxymethyl chitosan composite adsorbent and preparation method and application thereof

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CN112604672B (en) * 2020-12-01 2022-08-16 石河子大学 Functionalized carboxymethyl chitosan composite adsorbent and preparation method and application thereof

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