CN1206717A - Beta-D-(1-4)-dextran sulfate compound - Google Patents
Beta-D-(1-4)-dextran sulfate compound Download PDFInfo
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- CN1206717A CN1206717A CN 98118102 CN98118102A CN1206717A CN 1206717 A CN1206717 A CN 1206717A CN 98118102 CN98118102 CN 98118102 CN 98118102 A CN98118102 A CN 98118102A CN 1206717 A CN1206717 A CN 1206717A
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- dextran sulfate
- sulfate compound
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Abstract
The present invention relates to a medicinal compound for resisting AIDS-beta-D-(1-4)-dextran sulfate. Said compound is prepared by using hot-water (94 deg.C) extract of root of cynanchum otophyllum as raw material and treating said extract with pyridine-chlorosulfonic acid.
Description
The present invention relates to the compound field, particularly, relate to the medical compounds of anti-AIDS.
As everyone knows, acquired immune deficiency syndrome (AIDS) is a kind of to the very serious transmissible disease of human health threat, also is the difficult medical problem of the world today.At present, screening anti AIDS virus and immunity function restructuring medicine from plant amedica, also is an important channel of development anti-AIDS drug.Also do not have so far from the water extract of plant Cynanchum otophvllum, the sulfate compound of handling gained through pyridine-chlorsulfonic acid has the report of stronger anti-AIDS toxic action.
The object of the present invention is to provide a kind of β-D-(1-4)-dextran sulfate compound.
Structural formula of compound of the present invention is as follows:
β-D-of the present invention (1-4)-dextran sulfate compound can get with following method preparation:
Get hot water (94 ℃) extract of the root of Cynanchum otophvllum (Cynanchum otophyllum) plant, handle and get through pyridine-chlorsulfonic acid.
Pharmacological action with Cynanchum otophvllum-β of the present invention-D-(1-4)-dextran sulfate compound illustrates beneficial effect of the present invention below:
Cynanchum otophvllum-β-D-(1-4)-dextran sulfate compound (replacement M-33) is soluble in water, anti-HIV and anti-other virus experiments are carried out at U.S. NCI and Bayer A.G respectively, with cell culture method or in vitro tests method (In-Vitro Anti-HIV testing), anti-HIV test repeats repeatedly favorable reproducibility.The activity of anti-HIV all reaches " level of signification " (Active), and each test all compares with anti-HIV active drug AZT, and antiviral activity intensity is with therapeutic index (TI)=IC
50/ EC
50Size come classification, TI works energetically 100 for effectively.Test-results sees Table 1.
The antivirus test result at Bayer drug research center shows β-D-(1-4)-dextran sulfate compound except that having anti-HIV effect, visna virus (Visna), simplexvirus I and II type (Herpes I and II), influenza virus A and Type B (Influenza A and B) all there is activity, in addition hepatitis B virus being had restraining effect, is a kind of broad-spectrum antiviral medicament.Table 1 Cynanchum otophvllum-β-D-(1-4)-dextran sulfate compound (using code name M-33 in the table)
The therapeutic index of anti AIDS virus
| The medicine numbering | ?BC 50(mg/m1) | ?IC 50(mg/ml) | Therapeutic index TI=IC 50/EC 50 |
| ?M-33 | ?8.86×10 -1 | ?1.87×10 2 | ????211 |
| ?M-33 | ?5.62×10 -2 | ?1.87×10 2?????? | ????333 |
| ?M-33 | ?6.91×10 0 | ?2.50×10 3 | ????361 |
| ?M-33 | ?5.74×10 -2 | ?1.87×10 1 | ????326 |
| ?M-33 | ?4.88×10 0 | ?1.43×10 3 | ????288 |
| ?M-33 | ?4.18×10 0 | ?2.50×10 3 | ????366 |
| Contrast AZT | ????583 |
Can obtain conclusion from table, the therapeutic index of the anti AIDS virus of β-D-of the present invention (1-4)-dextran sulfate compound is 362.
Cell culture method that U.S. NCI is used or in vitro tests method (In-Vitro testing) are anti AIDS virus (Human Immunodeficiency Virus) drug screening methods general on present state-border.These method concrete steps are: place responsive susceptible host cell in culture dish, wherein half is infected with virus (HIV), and second half is a control group, adds that the medicine of different concns is sieved sample, places seven days in thermostatic chamber.It is most of or all damaged by virus not add the cell of medicine.Measure in above-mentioned two portions culture dish with fluorescent beam split photometry after seven days and remain viable count.With the cell survival percentage is ordinate zou, is X-coordinate with experiment drug concentrations mcg/ml, and the result of each test is found out corresponding point on coordinate, connects these points and obtains two curves (solid black lines, another is represented by dotted lines).Dotted line represents to add without the host cell that HIV infects the result of medicine, and solid line represents to be subjected to the performance of cell under the experiment drug effect of HIV infection to scheme.Middle two horizontal lines are respectively 0% and 50% reference line.Because medicine has the inhibiting while restraining effect also to be arranged to normal cell to virus.Above the concentration of intersection point of dotted line and 50% reference line be called IC
50, the expression medicine makes normal cell growth produce 50% drug level when suppressing, below solid line and 50% reference line intersection point be called EC
50, the expression medicine makes the cell disease of virus reduce by 50% drug level.IC
50With EC
50Ratio get therapeutic index TI=IC50/EC
50The therapeutic index of AZT is 583.Exactness for the antivirus action that helps to be subjected to the reagent thing has the AZT experimental result of HIV (human immunodeficiency virus)-resistant activity to do reference with known.
The toxicity test result of β-D-(1-4)-dextran sulfate compound: when being 500mg/kg for mouse vein (IV) or oral (P.O) dosage, the overt toxicity reaction do not occur, the LD of this compound is described
50＞500mg/kg.
Further specify flesh and blood of the present invention below in conjunction with accompanying drawing with embodiment, but content of the present invention is not limited thereto.
Fig. 2 is the anti-HIV pharmacological evaluation graphic representation of contrast AZT;
The anti-HIV pharmacological evaluation graphic representation of β-D-of Fig. 1 (1-4)-dextran sulfate compound.
Embodiment one:
Get root 500 gram of Cynanchum otophvllum (Cynanchum otophyllum) plant, be ground into behind the powder, merge vat liquor, cool off and left standstill 4 hours with hot water (94 ℃) lixiviate 2-3 time, centrifugation (4000 times/minute), the upper strata liquid that comes down in torrents, throw out is removed and is abandoned it.Upper strata liquid adds with the methyl alcohol of its 2-3 times volume, and shaking stirring is the cotton-shaped polysaccharide precipitation of adularescent, places liquid, the clarification of upper strata liquid, and lower sediment is tight.Remove upper strata liquid with the pipette suction, the lower sediment centrifugation, discard upper strata liquid, the lower sediment thing is transferred to suction funnel and takes out the oxygen filtration, the precipitation that leaches is used earlier washing with acetone, the back is with ether washing and press filtration, and throw out (has the Vanadium Pentoxide in FLAKES temperature absorption agent) in the device in the vacuum drier vacuum-drying 6 hours of bleeding must white polysaccharide 10 grams.
The affirmation of polysaccharide and sulfuric ester thereof: the white solid by above-mentioned gained dissolves in hot water on a small quantity, and taking out the ethanol that 1ml adds 2 times 95% has precipitation to produce.Get 2ml solution again, add 2ml10%HCl solution, heating made it hydrolysis in 20 minutes in boiling water, and PH is regulated to neutral in the cooling back, and hydrolyzed solution produces reduction reaction, promptly red copper oxidule precipitation to Fehling reagent (alkaline cupric tartrate reagent).Sugar in the hydrolyzed solution is through silica gel thin-layer chromatography and the contrast of known glucose, and Rf value and spot colors are consistent with grape, and have only spot of grape, so the polysaccharide of Cynanchum otophvllum is a dextran, in its infrared spectra 885em are arranged
-1, the oxidation of periodic acid potassium produces the red tinea phenol of D-(adjacent dibasic alcohol), shows between the glucose to be 1 → 4 connection.1100-1200em among its IR
-1Cutting edge of a knife or a sword shows C-O=S-OH, and complete because of the appearance demonstration esterification of no hydroxyl peak among the IR, activity is stronger.
The structural formula of β-D-of the present invention (1-4)-dextran sulfate compound is:
Claims (1)
1, β-D-(the 1-4)-dextran sulfate compound shown in (I) formula:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 98118102 CN1206717A (en) | 1998-07-28 | 1998-07-28 | Beta-D-(1-4)-dextran sulfate compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 98118102 CN1206717A (en) | 1998-07-28 | 1998-07-28 | Beta-D-(1-4)-dextran sulfate compound |
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| Publication Number | Publication Date |
|---|---|
| CN1206717A true CN1206717A (en) | 1999-02-03 |
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|---|---|---|---|
| CN 98118102 Pending CN1206717A (en) | 1998-07-28 | 1998-07-28 | Beta-D-(1-4)-dextran sulfate compound |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100494222C (en) * | 2006-04-30 | 2009-06-03 | 华南理工大学 | Preparation method of beta-1,4-glucan-6,2,3-sulfate |
| CN101891834A (en) * | 2010-07-20 | 2010-11-24 | 江苏先声药物研究有限公司 | Polysaccharide sulfate fragment (PSC), preparation method and application thereof |
| CN103479663A (en) * | 2012-06-11 | 2014-01-01 | 上海市公共卫生临床中心 | Application of yeast-origin glucan on preparation of drugs for curing hepatitis B virus infection |
-
1998
- 1998-07-28 CN CN 98118102 patent/CN1206717A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100494222C (en) * | 2006-04-30 | 2009-06-03 | 华南理工大学 | Preparation method of beta-1,4-glucan-6,2,3-sulfate |
| CN101891834A (en) * | 2010-07-20 | 2010-11-24 | 江苏先声药物研究有限公司 | Polysaccharide sulfate fragment (PSC), preparation method and application thereof |
| CN101891834B (en) * | 2010-07-20 | 2012-01-18 | 江苏先声药物研究有限公司 | Polysaccharide sulfate fragment (PSC), preparation method and application thereof |
| CN103479663A (en) * | 2012-06-11 | 2014-01-01 | 上海市公共卫生临床中心 | Application of yeast-origin glucan on preparation of drugs for curing hepatitis B virus infection |
| CN103479663B (en) * | 2012-06-11 | 2016-01-20 | 上海市公共卫生临床中心 | The application of yeast sources glucosan in the medicine of preparation treatment hepatitis B virus infection |
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