CN110251515A - A kind of preparation method and application of Rho kinase inhibitor Y27632 load Lentinan compound - Google Patents
A kind of preparation method and application of Rho kinase inhibitor Y27632 load Lentinan compound Download PDFInfo
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- CN110251515A CN110251515A CN201910663250.6A CN201910663250A CN110251515A CN 110251515 A CN110251515 A CN 110251515A CN 201910663250 A CN201910663250 A CN 201910663250A CN 110251515 A CN110251515 A CN 110251515A
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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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4409—Non condensed pyridines; Hydrogenated derivatives thereof only substituted in position 4, e.g. isoniazid, iproniazid
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/73—Polysaccharides
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/08—Anti-ageing preparations
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/74—Biological properties of particular ingredients
- A61K2800/78—Enzyme modulators, e.g. Enzyme agonists
- A61K2800/782—Enzyme inhibitors; Enzyme antagonists
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Abstract
The invention discloses a kind of preparation method and applications of Rho kinase inhibitor Y27632 load Lentinan compound, this method blends Lentinan and Rho kinase inhibitor Y27632, it proves to obtain by the influence test experience that inflammatory factor TNF-α and IL-1 β, the swelling of mouse toes, Keratinocyte Proliferation, skin improve situation respectively, Lentinan makes the stability of Rho kinase inhibitor Y27632 be greatly improved, and obtains preferably inhibiting inflammation and repair to improve skin effects in skin-protection product.
Description
Technical field
The invention belongs to field of pharmaceutical chemistry technology, and in particular to a kind of Rho kinase inhibitor Y27632 load Lenlinus edodes
The preparation method and application of polysaccharide compound.
Background technique
Lentinan is both water-soluble and electroneutral, is suitably applied in skin-protection product.It possesses excellent
Senile-resistant efficacy can smooth fine wrinkles, improve dermatoglyph degree.Moreover, it can assign product good Transdermal absorption
Performance can be used as the release carrier of active ingredient, gives skin and moistens smooth sense of touch such as silk.
Rho kinase inhibitor Y27632 promotes the proliferation of epithelial cells and same by inhibiting Rho GTPase pathway activity
When can hinder the aging death for even preventing epithelial cells, and inhibit Rho GTPase access that MYC albumen also can be improved
Activity, the high expression of MYC also has very important meaning to the proliferation of epithelial cells.In conclusion Rho kinase inhibitor
Y27632 has anti-inflammatory, anti-aging, promotees Keratinocyte Proliferation, accelerate wound healing, maintain the skin-protecting functions such as skin kilter.
The skin problems such as acne can be caused by inflammation, pass through inhibit inflammation and improve skin condition can be effectively improved acne,
The problems such as skin aging, scar acne print.In skin-protection product, generally requiring to arrange in pairs or groups, a variety of to generate synergistic effect, to play inhibition scorching
Disease simultaneously repairs improvement skin.
Summary of the invention
It is an object of the invention to overcome the deficiencies of the prior art and provide a kind of Rho kinase inhibitor Y27632 load is fragrant
The preparation method and application of mushroom polysaccharide compound, it is therefore intended that fusion Lentinan and Rho kinase inhibitor Y27632 make
Research and development of the two synergistic effect for skin-protection product and drug.
The present invention is achieved by the following technical solutions:
A kind of preparation method of Rho kinase inhibitor Y27632 load Lentinan compound, according to the following steps into
Row:
Step 1: the mixture of Rho kinase inhibitor Y27632 and Lentinan are dissolved in deionized water；With DCC
(dicyclohexylcarbodiimide) is used as condensing agent, and reaction is stirred at room temperature；
Wherein, the mass percent of Rho kinase inhibitor Y27632 is 2%-15%, Lentinan in the mixture
Mass percentage content 85%-98%；The mixture and the mass volume ratio (g/ml) of deionized water are 1:50-1:100；
Step 2: dialysis removes extra DCC and unreacted Rho kinase inhibitor Y27632, obtained after freeze-drying
A kind of Rho kinase inhibitor Y27632 loads Lentinan compound.
In the above-mentioned technical solutions, the Rho kinase inhibitor Y27632, CAS:146986-50-7, molecular weight:
320.3 white solid；The Lentinan, CAS:37339-90-5, molecular weight: 1152.9995, it is in pale powder.
In the above-mentioned technical solutions, described to be stirred to react the time as 16-32h in step 1.
In the above-mentioned technical solutions, in step 2, the dialysis time is 16-32h.
In the above-mentioned technical solutions, the preparation method of the Lentinan is as described below:
Step 1: tealeaves, sucrose, peptone, potassium hydrogen phosphate are dissolved in deionized water, tealeaves culture is obtained after sterilizing
Base；Wherein, the mass volume ratio (g/ml) of the tealeaves, sucrose, peptone, potassium hydrogen phosphate and deionized water be respectively 0.3%,
2%, 1% and 1%；
Step 2: tealeaves culture medium described in step 1 and shiitake mushroom hypha are co-cultured, the fermentation to shiitake mushroom hypha
Product water extract-alcohol precipitation separation and Extraction, polishing obtain Lentinan.
In the above-mentioned technical solutions, in step 2, the sterilising temp is 121 DEG C, and sterilization time is 20-30 minutes.
In the above-mentioned technical solutions, in step 2, the reaction temperature of the co-cultivation is 26-28 degree, and the reaction time is
3-7 days.
The advantages and benefits of the present invention are:
1, according to the comparison in embodiment with existing product, the technical program shows excellent properties of product:
(1) it is obtained by the influence test experience to inflammatory factor TNF-α and IL-1 β: Rho kinase inhibitor Y27632 load
Lentinan compound significantly inhibits the rising of inflammatory factor TNF-α and IL-1 β content caused by LPS is induced, and effect is aobvious
It writes and is better than positive drug dipotassium glycyrrhizinate and bisabolol, it is suitable with glucocorticoid hydrocortisone effect to press down scorching effect；
(2) obtained by the influence test experience of mouse toes swelling: Rho kinase inhibitor Y27632 loads Lentinan
Compound significantly inhibits carrageenan swelling caused by mouse toes, and significant effect is better than positive drug dipotassium glycyrrhizinate and red
Bisabol presses down scorching effect and is slightly better than glucocorticoid hydrocortisone；
(3) obtained by the test experience that Keratinocyte Proliferation influences: Rho kinase inhibitor Y27632 loads Lentinan
Compound remarkably promotes Keratinocyte Proliferation, and effect is better than positive drug dipotassium glycyrrhizinate and bisabolol and glucocorticoid hydrogen
Change cortisone；
(4) obtained by the test experience that skin improves situation: it is compound that Rho kinase inhibitor Y27632 loads Lentinan
Object can be effectively improved the water retention property of skin, improve cortex collagen content, improve skin elasticity.To the highest of water retention property
Improvement rate is suitable with hydrocortisone effect better than bisabolol and dipotassium glycyrrhizinate；Three are better than to the improvement of collagen content
Kind positive drug；Hydrocortisone and dipotassium glycyrrhizinate are better than to the highest improvement rate of skin elasticity, it is suitable with bisabolol effect.
Compared with the control group, Rho kinase inhibitor Y27632 loads Lentinan compound and is better than to the synthesis improvement of skin
Dipotassium glycyrrhizinate, bisabolol and hydrocortisone.
2, in the above-described embodiments, Rho kinase inhibitor Y27632 loads Lentinan compound relative to Rho kinases
Inhibitor Y27632 has better properties of product, after illustrating that Rho kinase inhibitor Y27632 is mixed with Lentinan, so that
The stability of Rho kinase inhibitor Y27632 is greatly improved, and is able to slow release during the reaction, therefore in skin-protection product
In obtain preferably inhibiting inflammation and repair to improve skin effects.
Detailed description of the invention
Fig. 1 shows Rho kinase inhibitor Y27632 load Lentinan compound to the shadow of inflammatory factor TNF-α
It rings.
Fig. 2 shows Rho kinase inhibitor Y27632 load Lentinan compounds to the shadow of inflammatory factor IL-1 β
It rings.
Fig. 3 shows influence of the Rho kinase inhibitor Y27632 load Lentinan compound to mouse toes swelling.
Fig. 4 shows influence of the Rho kinase inhibitor Y27632 load Lentinan compound to Keratinocyte Proliferation.
Wherein:
Y27632-Lentinan:Rho kinase inhibitor Y27632 loads Lentinan compound；
Y27632:Rho kinase inhibitor Y27632；
LPS: lipopolysaccharides；
GK2: dipotassium glycyrrhizinate；
Drag: bisabolol；
Hydr: hydrocortisone.
(P < 0.01 n=3, * *)
It for those of ordinary skill in the art, without creative efforts, can be according to above attached
Figure obtains other relevant drawings.
Specific embodiment
In order to enable those skilled in the art to better understand the solution of the present invention, combined with specific embodiments below furtherly
Bright technical solution of the present invention.
In following embodiments, unless otherwise specified, method therefor is conventional method, and agents useful for same all derives from commercially available quotient
Product.
Influence detection of the embodiment 1 to inflammatory factor TNF-α and IL-1 β
One, detection method:
Mouse macrophage RAW264.7 is inoculated in 12 orifice plates, 37 DEG C, after 5%CO2 incubator culture for 24 hours, is added
40mg/L lipopolysaccharides (LPS) act on 4h induce inflammatory reaction, Y27632-Lentinan, Y27632 (10 μM), GK2 (5 μM),
Drag (2.5 μM) and Hydr (5 μM) 2h before LPS is added is added.After LPS acts on 4h, cell conditioned medium is collected, is tried according to ELISA
The content of agent box specification measurement TNF-α and IL-1 β.
Two, conclusion:
As shown in Figure 1 and Figure 2, Rho kinase inhibitor Y27632 loads Lentinan compound (hereinafter referred to as
Y27632-Lentinan the rising of inflammatory factor TNF-α and IL-1 β content caused by LPS is induced) is significantly inhibited, and effect is aobvious
It writes and is better than positive drug dipotassium glycyrrhizinate and bisabolol, it is suitable with glucocorticoid hydrocortisone effect to press down scorching effect.
Influence detection of the embodiment 2 to mouse toes swelling
One, detection method:
It is made up a prescription with the sodium carboxymethylcellulose of mass percent 1g/100ml, makes product formation gel, and right in every mouse
Lower toes tow sides uniformly smear drug.After half an hour, 1% carrageenan is subcutaneously injected about in two toes of every mouse or so
0.025mL, blank control group mouse are not processed.Neck is taken off after 5h to put to death, and subtracts lower two foot of left and right along ankle-joint, weighing calculates swollen
Expansibility and swelling rate, and statistically analyze.
Blank control group mouse is not processed.Neck is taken off after 5h to put to death, and subtracts lower two foot of left and right along ankle-joint, weighing calculates swollen
Expansibility and swelling rate, and statistically analyze.
Swelling=inflammation group toes weight-blank group toes weight
Two, conclusion:
As shown in figure 3, Y27632-Lentinan significantly inhibits carrageenan swelling caused by mouse toes, and effect
It is significantly better than positive drug dipotassium glycyrrhizinate and bisabolol, presses down scorching effect and is slightly better than glucocorticoid hydrocortisone.
The detection that embodiment 3 influences Keratinocyte Proliferation
Reparation of the skin care item to cutaneous lesion is further related in anti-inflammatory therapeutic process, and the proliferation of epithelial cells is main
The form of expression.This part experiment detection Y27632-Lentinan, Y27632 and three kinds of positive drug dipotassium glycyrrhizinates (GK2),
Bisabolol (Drag) and hydrocortisone (Hydr) are to the proliferative effect at epithelial cells.Experimental method and result are as follows:
One, detection method:
People's epithelial cells are inoculated in 96 orifice plates with 5000cells/ hole density, and 37 DEG C, 5%CO2 incubator culture 12h is left
The right side is adherent to cell, Y27632-Lentinan (10 μM), Y27632 (10 μM), GK2 (5 μM), Drag (2.5 μM) and Hydr (5 μ
M it) is added in corresponding aperture, while setting one group of blank control, every group of 5 repetitions.Continue after cultivating 48h, every empty plus 25 μ L MTT
And continue to be incubated for 4h.Subsequent DMSO dissolution first a ceremonial jade-ladle, used in libation simultaneously detects OD490 light absorption value with microplate reader, statisticallys analyze to data.
Two, conclusion:
As shown in figure 4, Y27632-Lentinan remarkably promotes Keratinocyte Proliferation, and effect is better than positive drug glycyrrhizic acid
Dipotassium and bisabolol and glucocorticoid hydrocortisone.
Embodiment 4 improves the detection of situation to skin
One, detection method:
Recruit 30 volunteers (wherein 15 male, 15 female), be randomly divided into 6 groups (control, Y27632-Lentinan,
Y37632, GK2, Drag, Hydr), wherein each 3 people of every group of men and women.Experimental group is with equimolar volume ratio, by above-mentioned each substance and carboxylic
Sodium carboxymethylcellulose pyce is mixed with to obtain skin-protection product to be tested, and sodium carboxymethylcellulose gel is as blank control.Experiment
When, it will first be cleaned out on the inside of right hand wrist with wet tissue or washing every time, then by isometric above-mentioned skin care of soybean grain size
Product is uniformly wiped in right hand wrist inside line, once in the morning and once at night, is used continuously totally 28 days 4 weeks.Respectively at the 0th, 7,
14, TEWL (losing through epidermis water flow), Ultrasound (ultrasound), Elasticity (bullet are detected using DermaLab instrument within 28 days
Property) and Skin Color (colour of skin) be total to four indices, wet tissue wiped clean and dry in the air on the inside of volunteer's right hand wrist when detection every time
It shines 20 minutes or so and starts to detect to after drying.Room where instrument is stuffy, and without sunlight direct projection, room temperature is maintained at 24-25 DEG C,
Humidity is maintained at 40%.Finally obtained data are statisticallyd analyze.
Two, conclusion:
1. control group skin of table improves situation
Improvement situation of the table 2.Y27632-Lentinan to skin
Improvement situation of the table 3.Y27632 to skin
Improvement situation (GK2: dipotassium glycyrrhizinate) of 4. dipotassium glycyrrhizinate of table to skin
Improvement situation (Drag: bisabolol) of 5. bisabolol of table to skin
Improvement situation (Hydr: hydrocortisone) of 6. hydrocortisone of table to skin
It is obtained by above-mentioned table 1- table 6, Y27632-Lentinan can be effectively improved the water retention property of skin, improve cortex glue
Former protein content improves skin elasticity.Bisabolol and dipotassium glycyrrhizinate and hydrogenation are better than to the highest improvement rate of water retention property
Cortisone effect is suitable；Three kinds of positive drugs are better than to the improvement of collagen content；The highest improvement rate of skin elasticity is better than
Hydrocortisone and dipotassium glycyrrhizinate are suitable with bisabolol effect.Compared with the control group, Y27632-Lentinan is to skin
Synthesis improvement be better than dipotassium glycyrrhizinate, bisabolol and hydrocortisone.
Illustrative description has been done to the present invention above, it should explanation, the case where not departing from core of the invention
Under, any simple deformation, modification or other skilled in the art can not spend the equivalent replacement of creative work equal
Fall into protection scope of the present invention.
Claims (8)
1. a kind of preparation method of Rho kinase inhibitor Y27632 load Lentinan compound, which is characterized in that under
Column step carries out:
Step 1: the mixture of Rho kinase inhibitor Y27632 and Lentinan are dissolved in deionized water；Using DCC as
Reaction is stirred at room temperature in condensing agent；
Wherein, the mass percent of Rho kinase inhibitor Y27632 is 2%-15%, Lentinan quality in the mixture
Degree 85%-98%；The mixture and the mass volume ratio of deionized water are 1:50-1:100；
Step 2: dialysis removes extra DCC and unreacted Rho kinase inhibitor Y27632, obtained after freeze-drying described
A kind of Rho kinase inhibitor Y27632 load Lentinan compound.
2. a kind of preparation side of Rho kinase inhibitor Y27632 load Lentinan compound according to claim 1
Method, it is characterised in that: described to be stirred to react the time as 16-32h in step 1.
3. a kind of preparation side of Rho kinase inhibitor Y27632 load Lentinan compound according to claim 1
Method, it is characterised in that: in step 2, the dialysis time is 16-32h.
4. a kind of preparation side of Rho kinase inhibitor Y27632 load Lentinan compound according to claim 1
Method, which is characterized in that the preparation method of the Lentinan is as described below:
Step 1: tealeaves, sucrose, peptone, potassium hydrogen phosphate are dissolved in deionized water, tealeaves culture medium is obtained after sterilizing；Its
In, the tealeaves, sucrose, peptone, potassium hydrogen phosphate and deionized water mass volume ratio be respectively 0.3%, 2%, 1% and
1%；
Step 2: tealeaves culture medium described in step 1 and shiitake mushroom hypha are co-cultured, to the tunning of shiitake mushroom hypha
Water extract-alcohol precipitation separation and Extraction, polishing obtain Lentinan.
5. a kind of preparation side of Rho kinase inhibitor Y27632 load Lentinan compound according to claim 4
Method, it is characterised in that: in step 2, the sterilising temp is 121 DEG C, and sterilization time is 20-30 minutes.
6. a kind of preparation side of Rho kinase inhibitor Y27632 load Lentinan compound according to claim 4
Method, it is characterised in that: in step 2, the reaction temperature of the co-cultivation is 26-28 degree, and the reaction time is 3-7 days.
7. a kind of application of Rho kinase inhibitor Y27632 load Lentinan compound, it is characterised in that: the compound
For anti-inflammatory, anti-aging, the preparation for promoting Keratinocyte Proliferation, accelerating wound healing or skin care.
8. a kind of application of Rho kinase inhibitor Y27632 load Lentinan compound according to claim 7,
Be characterized in that: the preparation is liquid type, type of latex type, cream kind, powder class or powder compacting class.
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Citations (5)
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|---|---|---|---|---|
| CN1124656A (en) * | 1994-12-12 | 1996-06-19 | 王京杭 | Medicinal biological response regulating agent of cooperative polysaccharide modification |
| CN102988999A (en) * | 2012-05-09 | 2013-03-27 | 中国药科大学 | Curcumin-polysaccharide conjugate as well as preparation method and application thereof |
| CN103656671A (en) * | 2013-12-25 | 2014-03-26 | 中国科学院长春应用化学研究所 | Lentinan-adriamycin bonding medicine and preparation method thereof |
| CN105535011A (en) * | 2014-10-28 | 2016-05-04 | 天津国际生物医药联合研究院 | Applications of mushroom mycelium polysaccharides |
| CN108812989A (en) * | 2018-06-21 | 2018-11-16 | 付小智 | A method of with Ganoderma Lucidum fermented tea |
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2019
- 2019-07-22 CN CN201910663250.6A patent/CN110251515A/en active Pending
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1124656A (en) * | 1994-12-12 | 1996-06-19 | 王京杭 | Medicinal biological response regulating agent of cooperative polysaccharide modification |
| CN102988999A (en) * | 2012-05-09 | 2013-03-27 | 中国药科大学 | Curcumin-polysaccharide conjugate as well as preparation method and application thereof |
| CN103656671A (en) * | 2013-12-25 | 2014-03-26 | 中国科学院长春应用化学研究所 | Lentinan-adriamycin bonding medicine and preparation method thereof |
| CN105535011A (en) * | 2014-10-28 | 2016-05-04 | 天津国际生物医药联合研究院 | Applications of mushroom mycelium polysaccharides |
| CN108812989A (en) * | 2018-06-21 | 2018-11-16 | 付小智 | A method of with Ganoderma Lucidum fermented tea |
Non-Patent Citations (5)
| Title |
|---|
| V D GANDHAM 等: "Effects of Y27632 on keratinocyte procurement and wound healing", 《CLIN EXP DERMATOL》 * |
| 万茜淋 等: "香菇多糖的药理活性研究进展", 《中国药房》 * |
| 牛天增 等: "香菇多糖结构修饰研究进展", 《中国现代应用药学》 * |
| 王伟 等: "缩合剂1,3-二环己基碳二亚胺（DCC）在有机合成中的应用", 《化学试剂》 * |
| 雷敬敷等: "香菇发酵工艺及香菇多糖的提取", 《中国食用菌》 * |
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