CN105902533B - Purposes of the compound cercosporamide in immunopotentiator is prepared - Google Patents
Purposes of the compound cercosporamide in immunopotentiator is prepared Download PDFInfo
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- CN105902533B CN105902533B CN201610343657.7A CN201610343657A CN105902533B CN 105902533 B CN105902533 B CN 105902533B CN 201610343657 A CN201610343657 A CN 201610343657A CN 105902533 B CN105902533 B CN 105902533B
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- 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
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
- A61K31/343—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide condensed with a carbocyclic ring, e.g. coumaran, bufuralol, befunolol, clobenfurol, amiodarone
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Abstract
The present invention provides a kind of purposes of compound cercosporamide in immunopotentiator is prepared, which has immune-enhancing activity, for immuuoeorapromised hosts such as cancer, AIDS, immunodeficiency symptoms or agings.Cercosporamide English name Cercosporamide, 4 Dibenzofurancarboxamide of alias.Wherein, immunopotentiator includes active ingredient cercosporamide and auxiliary material.
Description
Technical field
, should the present invention relates to medicinal chemistry arts, specifically purposes of the cercosporamide in immunopotentiator is prepared
Compound has immune-enhancing activity in immune field.
Background technology
Pilot compound is found from natural products, is the important channel of new drug initiative.Microorganism is in nature
The main source of natural products, plant endogenesis epiphyte are relatively new research fields as one of those important monoid.It is interior
The secondary metabolite of raw mycetogenetic rich and varied tool multiple biological activities has in modern medicine and pesticide industry
Important application potential, they have in antibacterial, antiviral, desinsection, antitumor, anti-cardiovascular disease and the anti-ageing field of waiting for a long time
Wide application prospect.Exemplary is the discovery (Stierle et al., 1993) for the endogenetic fungus for producing taxol.It is another
Aspect have also discovered many new biological activity materials by plant endogenesis epiphyte, as being separated to from traditional medicinal plant tripterygium wilfordii
Endogenetic fungus Rhinocladiella sp. can produce 3 kinds of new cytochalasins (cytochalasin), to a variety of human tumor cells
There is very strong inhibitory action (Wagenaar et al, 2000)；The separated endogenetic fungus from sweet wormwood stem
Colletotrichum sp. can produce a variety of compounds for having good inhibitory action to disease fungus and plant pathogenetic bacteria, its
MIC value is generally at 25~50 μ g/L (Lu et al., 2000).Cercosporamide, English name Cercosporamide, alias 4-
Dibenzofurancarboxamide, empirical formula's (Xi Er representations)：C16H13NO7, molecular weight 331.28.Earliest, the change
Compound be in the tunning by Cercosporidium henningsii (cassava tail spore bacterium) separation and Extraction to.Thisization
Compound has the bacteriostatic activity of wide spectrum, has extraordinary effect to a variety of pathogens.Cercosporamide is also used as a hatching egg
The inhibitor of white kinases PKC1, can be as the ancillary drug for the treatment of diabetes.In addition, cercosporamide can block eucaryote
Promoter, have obvious effect in eIF4E Phosphorylation events, participate in apoptosis process.
For the immuuoeorapromised hosts such as cancer, AIDS, immunodeficiency symptoms and aging, carried using immunopotentiator
Its high immune function is critically important treatment means.Immunopotentiator, which removes, can improve the antitumor, anti-of immuuoeorapromised host
Outside virus, anti-microbial pathogen and anti parasitic ability, the immunologic adjuvant for being alternatively arranged as vaccine uses, and improves the immunogenicity of vaccine.
The immunopotentiator of Clinical practice is mainly the biological agents such as recombinant cytokine, thymic peptide, immunoglobulin at present, small molecule
Medicine levamisol, also has some Chinese medicines and its compound preparation.The immunological enhancement of micromolecular compound cercosporamide is exempted from
Epidemic disease adjustment effect has no document report so far.
The content of the invention
The present invention provides a kind of purposes of compound cercosporamide in immunopotentiator is prepared, which has immune
Enhancing activity, for immuuoeorapromised hosts such as cancer, AIDS, immunodeficiency symptoms or agings.Cercosporamide English name
Cercosporamide, alias 4-Dibenzofurancarboxamide.
In the immunopotentiator, the cercosporamide is the active ingredient of immunopotentiator, you can using as only
One active ingredient, can also be used as one of active ingredient.
The immunopotentiator is made of cercosporamide and auxiliary material.The weight of cercosporamide in the immunopotentiator
Percentage composition is 1%~99%, is more preferably 1%~5%, can specifically include the tail spore acyl of therapeutically effective amount as needed
Amine and one or more pharmaceutically acceptable auxiliary materials.
The pharmaceutically acceptable auxiliary material refers to the pharmaceutic adjuvant of pharmaceutical field, such as：Diluent, filler, glue
Mixture, wetting agent, sorbefacient, surfactant, disintegrant, absorption carrier, lubricant etc..It can in addition contain add other
Auxiliary material such as flavouring agent, sweetener etc..The i.e. described auxiliary material is diluent, filler, adhesive, wetting agent, sorbefacient, table
It is more than one or both of face activating agent, disintegrant, absorption carrier, lubricant, flavouring agent, sweetener.
The formulation of the immunopotentiator does not have stringent limitation, can be prepared into according to the existing method of pharmaceutical arts
Various formulations (such as making cercosporamide be mixed with one or more carriers, to be then made into required formulation), by taking orally,
The modes such as snuffing, rectum, parenteral or percutaneous dosing are applied to the patient for needing this treatment.
Immunopotentiator is tablet as mentioned, is made of the component of following weight percentage：
Further preferably, immunopotentiator is tablet, is made of the component of following weight percentage：
The immunopotentiator is capsule, is made of the component of following weight percentage：
Cercosporamide 3%~8%；
Lactose 89%~96.5%；
Magnesium stearate 0.5%~3%.
Preferably, the immunopotentiator is capsule, it is made of the component of following weight percentage：
Cercosporamide 5%；
Lactose 94%；
Magnesium stearate 1%.
The usage amount of the compounds of this invention can be according to route of administration, patient age, weight, the kinds of Diseases tune treated
Whole, its daily dose can be 0.01~100mg/kg weight.One or many it can use.
Brief description of the drawings
Fig. 1：Cercosporamide is under 0.078125,0.3125,1.25,5,20 μM of dosage to spleen lymphocyte proliferation and sword bean
The T cell proliferation experiment of albumin A induction, under 0.078125 μM of concentration, spleen lymphocyte proliferation rate is 11.5%, canavaline
The T cell proliferation rate of A inductions is 4%；Under 0.3125 μM of concentration, spleen lymphocyte proliferation rate is 15%, concanavalin A induction
T cell proliferation rate be 6%；Under 1.25 μM of concentration, spleen lymphocyte proliferation rate is 46%, the T cell of concanavalin A induction
Proliferation rate is 12%；Under 5 μM of concentration, spleen lymphocyte proliferation rate is 82%, and the T cell proliferation rate of concanavalin A induction is
20%；Under 20 μM of concentration, spleen lymphocyte proliferation rate is 53%, and the T cell proliferation rate of concanavalin A induction is 4%.Show
Cercosporamide shows as obvious immune-enhancing activity.
Embodiment
The embodiment of the present invention is described in further detail below in conjunction with the accompanying drawings.
Embodiment one：The immune-enhancing activity measure of compound cercosporamide：
1st, key instrument：MCO-15AC type cell incubators, SANYO GS company；SpX-250B-Z biochemical cultivation cases, on
Hai Boxun Industrial Co., Ltd.s；1700 type electronic balances, German Sartorius companies；SW-CJ-1F type superclean benches, Suzhou
Safe and sound air technique Co., Ltd；LD5-2A type centrifuges, Beijing Medical Centrifugal Machine Factory；1-13 type centrifuges, German SIGMA are public
Department；MH-1 type micro oscillators, its woods Bell's instrument manufacturing Co., Ltd of Jiangsu Haimen City；Synergy-2SLFPA all-wave lengths are more
Function microplate reader, BioTek companies of the U.S.；XDS-1B type biology inverted microscopes, Chongqing optical instrument factory.
2nd, experimental animal source：Female SPF C57BL/6 mouse, 6 week old, 18-22g, is purchased from the western Poole-Bi Kai in Shanghai
Experimental animal Co., Ltd, experimental animal are raised one week after buying, and are tested again after adapting to environment.The processing journey of experimental animal
Sequence is performed according to the regulation of Zhejiang Academy of Medical Sciences Laboratory Animal Welfare Ethics Committee.
3rd, reagent:1640 cell culture fluids of RPMI are purchased from Thermo Fisher companies, and it is blue or green to add 100IU/ml before use
Mycin, 100 μ g/ml streptomysins and 10% calf serum are configured to complete culture solution；Newborn calf serum is purchased from Hangzhou Chinese holly
Bioengineering Co., Ltd.Concanavalin A (concanavalin A, Con A), tetrazolium bromide (3- (4,5-
Dimethylthiazol-2-yl) -3,5-dipenyltetrazolium bromid, MTT), platform phenol is blue, dimethyl sulfoxide (DMSO) is molten
Liquid (DMSO) is purchased from Sigma companies；Cell strainer is purchased from Biologix companies between 40 μm of holes；Penicillin and Streptomycin Solution,
Hank ' s liquid is purchased from the green skies biotechnology research institute in Jiangsu.
4th, test sample compound cercosporamide is purchased from SIGMA companies, English name Cercosporamide, alias 4-
Dibenzofurancarboxamide, article No. SML-0172, CAS 131436-22-1, empirical formula's (Xi Er representations)：
C16H13NO7, molecular weight 331.28.Cercosporamide is first dissolved as 50mM concentration, -20 DEG C of freezen protectives with DMSO.Adopt again before use
Respective concentration is diluted to RPMI1640 cell culture fluids.Han Liang≤0.2% of DMSO in dilution, to the bioactivity of cell
Do not influence.
5th, prepared by single splenocyte suspension：Mouse is sterile to take spleen, after grinding, adds appropriate Hank ' s liquid to be suspended, with 40 μm of holes
Between cell strainer filter, 1500rpm centrifuge 5 minutes, abandon supernatant, add Hank ' s liquid repeated washing 2 times.Splenocyte is collected, is added
RPMI1640 complete culture solutions are suspended and single splenocyte suspension are made.The numeration of dye method is refused with 0.4% phenol indigo plant, viable count is many
In 95%.
6th, spleen lymphocyte proliferation measuring：In 96 hole flat-bottomed plates, per hole add 100 μ L splenocyte suspensions (5 ×
10 6Cell/ml), (0,0.078,0.313,1.25,5,20 μM) 100 μ l of dilution for supplying reagent thing of various concentrations is added, often
A concentration repeats 4 holes, separately sets normal cell controls hole.37 DEG C, 5%CO2Cultivate 44 it is small when after, each hole adds MTT solution (2mg/
Ml) 50 μ l, continue to cultivate 4h.Centrifuge (1800rpm, 5min), discard each hole supernatant, respectively Plus acidic DMSO solution (4%1N
HCl) 150 μ l, lucifuge vibration 15min, measure OD 490nm, and 0% is calculated as with the proliferation rate in 0 hole of drug concentration, calculate medicine and make
Relative cell proliferation rate after.MTT is a kind of powdered chemical reagent, and full name is 3- (4,5)-dimethylthiahiazo
(- z-y1) -3,5-di-phenytetrazoliumromide, entitled 3- (4,5- dimethylthiazole -2) -2, the 5- bis- of Chinese chemistry
Phenyl tetrazole bromide, trade name：Tetrazolium bromide, is a kind of dyestuff of yellow color.The testing principle of mtt assay is living cells mitochondria
In succinate dehydrogenase bluish violet crystallization first a ceremonial jade-ladle, used in libation that exogenous MTT can be made to be reduced to water-insoluble (Formazan) and be deposited on
In cell, and dead cell is without this function.Dimethyl sulfoxide (DMSO) (DMSO) can dissolve the first a ceremonial jade-ladle, used in libation in cell, with microplate reader in 490nm ripples
Strong point measures its absorbance value, and in the range of certain cell number, it is directly proportional to cell number that MTT crystallizes the amount to be formed.According to measuring
Absorbance (OD values), to judge Living cells proliferation quantity, OD values are bigger, and cytoactive is stronger, and appreciation rate is higher.
7th, the T cell proliferation experiment measure of Con A inductions：In 96 hole flat-bottomed plates, 100 μ L splenocytes are added to hang per hole
Liquid (5 × 106Cell/ml), and add 50 μ l Con solution As (2 μ g/ml), be eventually adding various concentrations (0,0.078,
0.313rd, 1.25,5,20 μM) 4 holes are repeated, separately set normal cell controls hole for the 50 μ l of dilution of reagent thing, each concentration.37
DEG C, 5%CO2Cultivate 44 it is small when after, each hole adds MTT solution (2mg/ml) 50 μ l, continues to cultivate 4h.Centrifugation (1800rpm,
5min), each hole supernatant is discarded, respectively Plus acidic 150 μ l of DMSO solution (4%1N HCl), lucifuge vibration 15min, measures OD
490nm, is calculated as 0% with the proliferation rate of Con A functional holes (drug concentration 0), calculates the Relative cell proliferation rate after drug effect.
After measured, which can not only directly promote in 0.078125,0.3125,1.25,5,20 μM of dosage
Into spleen lymphocyte proliferation, moreover it is possible to remarkably promote the T cell propagation of concanavalin A induction, under 0.078125 μM of concentration, spleen leaching
Bar cell proliferation rate is 11.5%, and the T cell proliferation rate of concanavalin A induction is 4%；Under 0.3125 μM of concentration, spleen lymph
Cell proliferation rate is 15%, and the T cell proliferation rate of concanavalin A induction is 6%；Under 1.25 μM of concentration, splenic lymphocytes increase
It is 46% to grow rate, and the T cell proliferation rate of concanavalin A induction is 12%；Under 5 μM of concentration, spleen lymphocyte proliferation rate is
82%, the T cell proliferation rate of concanavalin A induction is 20%；Under 20 μM of concentration, spleen lymphocyte proliferation rate is 53%, knife
The T cell proliferation rate of legumin A inductions is 4%.Data above all shows that cercosporamide shows as obvious Immune-enhancing effect and lives
Property (as shown in Figure 1).
Embodiment two
Preparation method：Active ingredient cercosporamide, lactose and cornstarch are mixed, uniformly moistened with water, after moistening
Mixture sieves and dries, re-sieving, adds magnesium stearate, then by mixture tabletting, every weight 250mg, active ingredient ratio
Example 1%, content 2.5mg.
Embodiment three
Preparation method：Active ingredient cercosporamide, lactose and cornstarch are mixed, uniformly moistened with water, after moistening
Mixture sieves and dries, re-sieving, adds magnesium stearate, then by mixture tabletting, every weight 250mg, active ingredient ratio
Example 4%, content 10mg.
Example IV
Capsule：Active ingredient cercosporamide 1.0g
Lactose 18.8g
Magnesium stearate 0.2g；
Preparation method：Active ingredient cercosporamide, lactose and magnesium stearate are mixed, sieving, loads hard shell capsules, each glue
Capsule weight 200mg, active ingredient ratio 5%, content 10mg.
Embodiment five
Capsule：Active ingredient cercosporamide 198g
Lactose 1.8g
Magnesium stearate 0.2g；
Preparation method：Active ingredient cercosporamide, lactose and magnesium stearate are mixed, sieving, loads hard shell capsules, each glue
Capsule weight 200mg, active ingredient ratio 99%, content 198mg.
Embodiment six
Capsule：Active ingredient cercosporamide 18g
Lactose 1.8g
Magnesium stearate 0.2g；
Preparation method：Active ingredient cercosporamide, lactose and magnesium stearate are mixed, sieving, loads hard shell capsules, each glue
Capsule weight 200mg, active ingredient ratio 90%, content 180mg.
Embodiment seven
Immunopotentiator is tablet, is made of the component of following weight percentage：
Embodiment eight
Immunopotentiator is tablet, is made of the component of following weight percentage：
Embodiment nine
Immunopotentiator is capsule, is made of the component of following weight percentage.
Cercosporamide 3%~8%；
Lactose 89%~96.5%；
Magnesium stearate 0.5%~3%.
Embodiment ten
Immunopotentiator is capsule, is made of the component of following weight percentage：
Cercosporamide 5%；
Lactose 94%；
Magnesium stearate 1%.
Compound or the usage amount of immunopotentiator can be according to route of administration, patients into embodiment ten for above-described embodiment two
Age, weight, the kinds of Diseases adjustment treated, its daily dose can be 0.01~100mg/kg weight.Can be once or more
Secondary use.
Finally, it should also be noted that it is listed above be only the present invention several specific embodiments.Obviously, this hair
It is bright to be not limited to above example, there can also be many deformations.Those of ordinary skill in the art can be from present disclosure
All deformations for directly exporting or associating, are considered as protection scope of the present invention.
Claims (8)
1. purposes of the compound cercosporamide in immunopotentiator is prepared, it is characterized in that：The compound cercosporamide is made
For the active ingredient of immunopotentiator, compound cercosporamide concentration is 0.078125~20 μM in the immunopotentiator.
2. purposes of the compound cercosporamide according to claim 1 in immunopotentiator is prepared, it is characterized in that：It is described
Immunopotentiator further include auxiliary material.
3. purposes of the compound cercosporamide according to claim 2 in immunopotentiator is prepared, it is characterized in that：It is described
Immunopotentiator in cercosporamide weight percentage be 1%~5%.
4. purposes of the compound cercosporamide according to claim 2 in immunopotentiator is prepared, it is characterized in that：It is described
Immunopotentiator in cercosporamide weight percentage be 4%.
5. purposes of the compound cercosporamide according to claim 2 in immunopotentiator is prepared, it is characterized in that：It is described
Immunopotentiator in cercosporamide weight percentage be 2%~6%.
6. purposes of the compound cercosporamide according to claim 2 in immunopotentiator is prepared, it is characterized in that：It is described
Immunopotentiator in cercosporamide weight percentage be 3%~8%.
7. according to purposes of any compound cercosporamides of claim 2-6 in immunopotentiator is prepared, its feature
It is：The auxiliary material includes diluent, adhesive, wetting agent, sorbefacient, disintegrant, lubricant, flavouring agent, sweetener
In one or more.
8. according to purposes of any compound cercosporamides of claim 2-6 in immunopotentiator is prepared, its feature
It is：The auxiliary material includes lactose or cornstarch or magnesium stearate.
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| CN101292039A (en) * | 2005-08-09 | 2008-10-22 | 第一三共株式会社 | Method for producing cercosporamide |
| CN101300244A (en) * | 2005-08-09 | 2008-11-05 | 第一三共株式会社 | Novel cercosporamide derivative |
| CN102154125A (en) * | 2011-03-31 | 2011-08-17 | 浙江大化生物科技股份有限公司 | Phoma strain and application thereof |
| WO2015050957A2 (en) * | 2013-10-02 | 2015-04-09 | Treatments For Systemic Lupus Erythematosus | Treatments for systemic lupus erythematosus |
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2016
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101292039A (en) * | 2005-08-09 | 2008-10-22 | 第一三共株式会社 | Method for producing cercosporamide |
| CN101300244A (en) * | 2005-08-09 | 2008-11-05 | 第一三共株式会社 | Novel cercosporamide derivative |
| CN102154125A (en) * | 2011-03-31 | 2011-08-17 | 浙江大化生物科技股份有限公司 | Phoma strain and application thereof |
| WO2015050957A2 (en) * | 2013-10-02 | 2015-04-09 | Treatments For Systemic Lupus Erythematosus | Treatments for systemic lupus erythematosus |
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| Therapeutic Inhibition of MAP Kinase Interacting Kinase Blocks Eukaryotic Initiation Factor 4E Phosphorylation and Suppresses Outgrowth of Experimental Lung Metastases;Bruce W. Konicek等;《Cancer Research》;20110113;第71卷;第1849-1857页 * |
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