CN1450075A - Group No.1 oligose and sulfated products, their preparation process and medicine composition containing said oligose - Google Patents
Group No.1 oligose and sulfated products, their preparation process and medicine composition containing said oligose Download PDFInfo
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- CN1450075A CN1450075A CN 02116614 CN02116614A CN1450075A CN 1450075 A CN1450075 A CN 1450075A CN 02116614 CN02116614 CN 02116614 CN 02116614 A CN02116614 A CN 02116614A CN 1450075 A CN1450075 A CN 1450075A
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Abstract
Said invention refers to gluco oligose with function of anti-virus anti-infection, anti-tumor and raising immunity, and sulfated products structure and preparation. Said oligose is composed of alternate connected 1-3 alpha and 1-3 beta, the trisaccharides is prepared by diose added with monose, the tetrose is prepared by diose added with diose, and so on and so forth, the pentasaccharides, hexasaccharides, heptasaccharides and octasaccharides can be prepared. The sulfated oligose can be prepared by common process of sulfating obtained oligose.
Description
Technical field
The invention relates to antivirally, anti-infective, antitumor and to improve immunizing power active, particularly related to and can be used as strengthening immunity, antitumor, the product of the healthcare products of AIDS resisting or the oligosaccharides of medicine and sulphating thereof.Be specifically related to contain 1,3-β-and 1, the ligoglucoside of 3-α-alternately connect the invention still further relates to the preparation method of described oligosaccharides and sulfation product thereof and contains the pharmaceutical composition of this oligosaccharides.
Background technology
The World Health Organization's report, had the infection that 1,800 ten thousand adults and 1,500,000 children have been subjected to acquired immune deficiency syndrome (AIDS) in 1993 in the world, and end-stage patients have been developed into, at present, whole world AIDS patient has increased to 4,000 ten thousand, according to scholarly forecast, and the coming years, the AIDS patient of China also will be multiplied, and reach millions of.In order to defeat this century plague, in the past recent two decades, drop into a huge sum of money with the developed country headed by the U.S. and developed and comprise AZT, DDI, DDC etc. be at the medicine of interior kind more than ten treatment acquired immune deficiency syndrome (AIDS), yet, take these chemical synthetic drugs for a long time, HIV (human immunodeficiency virus) has produced resistance soon.The mankind also can subdue this demon far away.So WHO wishes to develop natural drug and derivative thereof.The derivative of finding polysaccharide over past ten years especially controlling sulfate polyose has unique effect, uses clinically as antithrombotic reagent; D-glucose-D-semi-lactosi sulfuric ester and some steroidal share the medicine as the disease of some angiogenic of treatment.But the more important thing is that it has antivirus action (J.Med.Chem.1987,30,810; Biochem.Pharmacol.1990,39,793), its application on treating AIDS is confirmed.The Sulfate of polysaccharide that wherein condenses will have entered I/II phase clinical stage from the end of the year 1992 in the U.S..But controlling sulfate polyose can produce a kind of serious anticoagulation side effect when suppressing HIV (human immunodeficiency virus).Studies have shown that further the oligose fragment in the polysaccharide has almost same high antiviral activity behind sulphating and side effect almost can be ignored, is the medicine of ideal AIDS resisting poison.To condense the polysaccharide acidolysis after the high performance liquid chromatography separation obtains 1 as Japanese scientist Toshiyuki Uryu people such as (Carbohydrate Research 260 (1994) 51-64), the poly-pentasaccharides in the Portugal that 3-β connects, six sugar and seven sugar, behind the reducing end alkylglycoside, be prepared into the sulfuric ester oligosaccharides, find its AIDS resisting cytotoxic activity even be better than the polysaccharide that condenses of sulphating, and the anticoagulation side effect is almost nil.The Australia scientist has delivered one piece of patent (world patent PCT WO96/33726) that reaches 68 pages, has described the pharmaceutical use of various sulphated oligosaccharides.We will synthesize new oligosaccharides of a class and sulfation product thereof among the present invention.
The objective of the invention is to confirm that main chain contains 1,3-β-and 1, the ligoglucoside and the sulfating product thereof of 3-α-alternately connection have antiviral, anti-tumor activity, can be as immunostimulant, antitumor, and the healthcare products of AIDS resisting or medicine.
By oligosaccharides their activity test is carried out in the influence of the gene expression dose of healthy human peripheral blood monocyte IL-2 and TNF-α and the situation of inhibition tumor effect;
By what these tests were determined immunity, anti-tumor activity and can be as strengthening immunity, antitumor be arranged, the new texture of the oligosaccharides in the sulfated oligosaccharide of AIDS resisting is:
Wherein n is the integer of 2-8, R=glucose, R
1Be terminal group, represent glucose, semi-lactosi or seminose or other sugar, but also representation hydrocarbyl such as alkyl, thiazolinyl, aryl glycosides or oligose peptide, and its alkyl carbon chain lengths is 1-20, preferably 6-18.Alternately be connected with 1 → 3 β with 1 → 3 α between the sugar unit.
As: β-Glu-1 → 3-α-Glu-1 → 3-β-Glu-1 → 3-α-Glu-1 → 3-β-Glu-1 → 3-Glu α-Glu-1 → 3-β-Glu-1 → 3-α-Glu-1 → 3-β-Glu-1 → 3-α-Glu-1 → 3-Glu β-Glu-1 → 3-α-Glu-1 → 3-β-Glu-1 → 3-α-Glu-1 → 3-β-Glu-1 → 3-Glu-OC
12H
25α-Glu-1 → 3-β-Glu-1 → 3-α-Glu-1 → 3-β-Glu-1 → 3-α-Glu-1 → 3-Glu-OC
12H
25Or the like.
2. one kind has antivirally, anti-infective, antitumor and improve the oligosaccharides and the sulfation product thereof of pharmacological actions such as immunizing power, it is characterized in that: the synthetic methods of 2 sugar described in the right 1,3 sugar, 4 sugar, 6 sugar, 7 sugar and bigger sugar:
This method comprises that the tribromo-acetyl imines ester 1 with the acyl glucose of 3 allylations is a glycosyl donor; with 3 is that the acyl glucose alkyl glucoside 2 of free hydroxyl group is a glycosyl acceptor; at first obtain 1; the disaccharide of 3-β-connection; optionally 3 allyl group is fallen in hydrolysis; promptly obtain two saccharide acceptors 3, shown in the following structural formula:
Synthetic 3 is two saccharide donors of the allylic glucose in position with similar method; promptly use 3-O-allyl group-2; 4, the glycosyl donor 4 of 6-three-O-acyl-alpha--D-glucose makes itself and monose acceptor 5 under Louis acid catalysis; coupling obtains corresponding 1 under the stirring at room; the disaccharide of 3-β-connection, optionally hydrolysis fall 1 to anisole, it is activated; obtain two saccharide donors 6, shown in the following structural formula:
With etc. two saccharide donors 6 of mol ratio and two saccharide acceptors 3 under Louis acid catalysis, coupling under the stirring at room obtains 1,3-β-and 1,4 sugar of 3-α-alternately connect, optionally 3 allyl group is fallen in hydrolysis, promptly obtains tetrose acceptor 7, shown in the following structural formula:
With etc. two saccharide donors 6 and the tetrose acceptor 7 of mol ratio under Louis acid catalysis, coupling under the stirring at room obtains 1,3-β-and 1, six sugar 8 of the protection of 3-α-alternately connect go protection promptly to obtain needed six sugar 9 again.Shown in the following structural formula:
With identical method, the disaccharide that connects with α-1 → 3-is donor and acceptor, can prepare α-Glu-1 → 3-β-Glu-1 → 3-α-Glu-1 → 3-β-Glu-1 → 3-α-Glu-1 → 3-Glu-OC easily
12H
25Use similar method, can synthesize pentasaccharides, seven sugar, eight sugar, nine sugar etc.
Described oligosaccharides, non-sugared body are divided into alkyl such as alkyl, thiazolinyl, aryl, and its carbon chain lengths is 1-20, preferably 6-12; Non-sugared body portion also can be amino acid and peptide chain,
Described acyl group is a benzoyl, ethanoyl or other acyl group.
Described Lewis acid is silver salt such as silver carbonate, silver trifluoromethanesulfonate, or is boron trifluoride, or is the trifluoromethanesulfonic acid trimethylsilyl group.
2. one kind has antivirally, anti-infective, antitumor and improve the oligosaccharides and the sulfation product thereof of pharmacological actions such as immunizing power, and it is characterized in that: the degree of the sulfovinic acidization of the oligose sulfate product described in the right 1 is greater than 1/5, preferably 1/3-2/3.
Oligose sulfate product described in oligosaccharides described in the right 1 and the right 3 can be separately with or share with other material, as antiviral, anti-infective, antitumor and improve the healthcare products or the medicine of immunizing power.
Below in conjunction with embodiment the present invention is described in detail.
The preparation of embodiment 1. 2 saccharide acceptors 3:
The tribromo-acetyl imines ester 1 of the acyl glucose of 3 allylations (5.6 grams; 7.56 mmole) be dissolved in 40 milliliters of methylene dichloride; solution A, 3 be that the acyl glucose alkyl glucoside 2 (2.8 restrain, 10.77. mmole) of free hydroxyl group is dissolved in 20 milliliters of methylene dichloride; get solution B; with B mix with A solution C, in C, add trifluoromethanesulfonic acid trimethylsilyl group (TMSOTF, 0.08 mmole); after two hours, thin-layer chromatographic analysis shows to react to be finished at room temperature reaction.Obtain corresponding disaccharides.It is dissolved in 100 milliliters of exsiccant methanol solutions, add Palladous chloride 0.5 gram, under room temperature, stirring, react, and detect with tlc analysis, when detection shows that allyl group has been removed by selectivity, filter, decompression is solvent evaporated down, and crude product is refining with silica gel column chromatography, with ethyl acetate/petroleum ether (1/1) as leacheate drip washing, collect respective components, obtain disaccharides 3 (4.22 gram), productive rate: 87%.2. disaccharides is given the preparation of body 6
By 1 and 2 link coupled conditions, promptly use 3-O-allyl group-2,4,6-three-O-ethanoyl-alpha-D-glucose tribromo-acetyl imines ester 4 (4.10 grams, 8.38 millimoles) and monose acceptor 5 (2.13 grams, 8.20 millimoles) coupling obtain corresponding disaccharides.With its optionally hydrolysis fall 1 to anisole, be dissolved in 40 milliliters of methylene dichloride, add 3 milliliters in three chloroethene eyeballs, salt of wormwood 3 grams, stirred under the room temperature 23 hours, tlc analysis shows to react to be finished, and carries out aftertreatment with ordinary method, and crude product is refining with silica gel column chromatography, with ethyl acetate/petroleum ether (1/1) as leacheate drip washing, collect respective components, obtain two pure saccharide donors 6 (6.01 gram), productive rate: 91%.Shown in the following structural formula:
3. the preparation of tetrose acceptor 7
Method according to preparation two saccharide acceptors 3, make two saccharide donors 6 (3.12 grams, 2.13 millimole) with two saccharide acceptors 3 (0.80 gram, 2.50 millimole) coupling obtains 1,3-β-and 1,4 sugar of 3-α-alternately connect, optionally 3 allyl group is fallen in hydrolysis, promptly obtains tetrose acceptor 7 (2.34 grams, productive rate 69%).Shown in the following structural formula:
4. the preparation of six sugar 9
Two saccharide donors 6 (3 grams, 1.92 millimoles) and tetrose acceptor 7 (2.12 grams, 1.91 millimoles) are dissolved in 40 milliliters of methylene dichloride; under cryosel bath cooling, add TMSOTf (0.02 mmole), return to room temperature then naturally, in nitrogen protection; room temperature; react under stirring; detect with tlc analysis, after reaction is finished, use the ordinary method aftertreatment; crude product is refining with silica gel column chromatography; as leacheate drip washing, collect respective components with ethyl acetate/petroleum ether (2/1), obtain 1; 3-β-and 1; six sugar 8 of the protection of 3-α-alternately connect, with 8 its be dissolved in 40 ml methanol, saturated with ammonia; ambient temperature overnight; use the tlc analysis detection reaction, after reaction is finished, the evaporated under reduced pressure solvent; use washed with dichloromethane; discard washings, obtain pulverous needed six sugar 9 (681 milligrams), overall yield 55%.As shown below:
Use similar method, can synthesize pentasaccharides, seven sugar, eight sugar, nine sugar etc.5. the preparation of sulfation six sugar
Sulphur trioxide-pyridine complex 4 grams are dissolved among 5 milliliters of DMF, be heated to 80 ℃, stir the solution of 00 milligram of six sugar 9 of Dropwise 5 in 15 milliliters of pyridines down, reactant reacted 100 minutes down at 80 ℃ again, under the condition of heat, outwell supernatant, with the dope of remainder with 10 ml methanol washing three times, remove remaining methyl alcohol, product is dissolved in 15 ml waters, under agitation is neutralized to pH and is 6 with barium acetate, centrifugal, divide to fall supernatant, remaining barium salt water is given a baby a bath on the third day after its birth inferior, and supernatant and washings are merged, and is refining with Zeo-karb DOWEX 50W-X8-400, is neutral with water wash up to leacheate, leacheate is neutralized with sodium acetate, and solution is with 1 liter of acetone diluted, and is centrifugal, free six sugar are obtained sulfating product 10 amount to 0.88 gram, productive rate 55%.As shown below:
Wherein R represents sulfate group or hydrogen.
Described sulfated oligosaccharide is injectable or oral (separately with or share with other material) in use.Can be used as strengthening immunity, antitumor, the healthcare products of AIDS resisting or medicine.
Below in conjunction with embodiment the present invention is described in detail.
1. described sulfated oligosaccharide (10) has remarkably influenced to gene expression dose and the activity of healthy human peripheral blood monocyte IL-2 and TNF-α, in the concentration range of 0.5 mg/litre-10 mg/litre, increase this gene expression dose and active increasing, induction of immunity reaction with concentration.
2. described sulfated oligosaccharide (10) is complete by way of the swollen tumour of oligosaccharides inject time to the situation tumor host oligosaccharides dosage of the anticancer and anticancer transferance of the described sulfated oligosaccharide of the restraining effect of tumour (10)
(knurl inhibiting rate extinction rate sarcoma 180 CD-1/JCR 1 * 10 i.p. 1t,o10 10010/10 of 1mg/kg * d)
A/J 5×4 i.p 1to4 93.79/10
DBA/2N 5×4 i.p. 1to4 9510/10
SWM/Ms 1 * 10 i.p. 1t,o10 10010/10 Emhorn abdominal cavity cancer CD-1/ICR 1 * 10 i.p. 1to10 53.20/5CCM gland cancer SWM/Ms 1 * 10 i.p. 1to10 63.50/10MC.S1 fibrosarcoma A/J 1 * 10 i.p. 1to10 10018/18MC.CS1 fibrosarcoma DBA/2N 1 * 10 i.p. 1t,o10 78.52/7 methyl cholanthrene SWM/Ms 1 * 10 i.p. 21t,o31 81 → 32% methyl cholanthrene DBA/2N 1 * 10 i.p. 14t,o24 76 → 35% adenopathies 12 type C3H/HeN 3 * 10 i.p. 14t,o18 77 → 37%
This shows that described sulfated oligosaccharide is not only to transplanting cancer of the same race such as S180 but also to the homology cancer, the growth of spontaneous cancer also can obviously suppress, and to chemocarcinogenesis, virus is carcinogenic all preventive effect.
The characteristics of described sulfated oligosaccharide function of tumor inhibition are: tumour cell is not had direct cytotoxicity, and its effect depends on the host; Dose,optimum is arranged, and excessive use weakens function of tumor inhibition and immuno-potentiation; There were significant differences because of mouse kind system is different in its effect.A/J, DBA/2, mouse such as CD-1 are the most responsive to sulfated oligosaccharide, but the tumour completely dissolve.C3H/He is not disappeared, BALB/C, CBA is medium.To responsive mouse inoculation methyl-cholanthrene (MC), set up the fibrosarcoma strain, transplant behind inbred mouse with this, give with sulfated oligosaccharide after tumour disappear.
Described sulfated oligosaccharide has strong restraining effect to chemocarcinogenesis.Inoculation MC35 after week nearly all mouse cancer all takes place, but throw and sulfated oligosaccharide in inoculation MC2～begin after 3 weeks abdominal cavity, carcinogenic rate is reduced to 30% approximately.This is because the minority cancer cells that inoculation MC produces has strengthened immunologic function owing to the injection oligosaccharides and eliminated.Oligosaccharides also can make the carcinogenic rate of adenovirus be reduced to 40% by 80%.Show that sulfated oligosaccharide singly is not to promote the material of immunological rejection and is cancer-resisting substance.
In addition, described oligosaccharides is to various bacteriums, virus, and parasitic infection also has outstanding effect.
Pharmaceutical composition Example formulations embodiment 1
6 sugars of 1000 milligrams, 5000 milligrams and 10000 milligrams formulas 10 are not dissolved in 1000 milliliters 1% normal saline solution, being configured to concentration respectively is the injectable drug of 1 mg/ml, 5 mg/ml and 10 mg/ml, and this injectable drug is configuration in use usually.
Claims (4)
1. one kind has antivirally, anti-infective, antitumor and improve the oligosaccharides of pharmacological actions such as immunizing power and the structure of sulfation product thereof, and it is characterized in that: its oligosaccharides has following structural formula:
Wherein n is the integer of 2-8,
R=glucose, R
1Be terminal group, represent glucose, semi-lactosi or seminose or other sugar, but also representation hydrocarbyl such as alkyl, thiazolinyl, aryl glycosides or oligose peptide, and its alkyl carbon chain lengths is 1-20, preferably 6-18.Alternately be connected with 1 → 3 β with 1 → 3 α between the sugar unit.
As: β-Glu-1 → 3-α-Glu-1 → 3-β-Glu-1 → 3-α-Glu-1 → 3-β-Glu-1 → 3-Glu α-Glu-1 → 3-β-Glu-1 → 3-α-Glu-1 → 3-β-Glu-1 → 3-α-Glu-1 → 3-Glu β-Glu-1 → 3-α-Glu-1 → 3-β-Glu-1 → 3-α-Glu-1 → 3-β-Glu-1 → 3-Glu-OC
12H
25α-Glu-1 → 3-β-Glu-1 → 3-α-Glu-1 → 3-β-Glu-1 → 3-α-Glu-1 → 3-Glu-OC
12H
25Or the like.
2. one kind has antivirally, anti-infective, antitumor and improve the oligosaccharides and the sulfation product thereof of pharmacological actions such as immunizing power, it is characterized in that: the synthetic methods of 2 sugar described in the right 1,3 sugar, 4 sugar, 6 sugar, 7 sugar and bigger sugar:
This method comprises that the tribromo-acetyl imines ester 1 with the acyl glucose of 3 allylations is a glycosyl donor; with 3 is that the acyl glucose alkyl glucoside 2 of free hydroxyl group is a glycosyl acceptor; at first obtain 1; the disaccharide of 3-β-connection; optionally 3 allyl group is fallen in hydrolysis; promptly obtain two saccharide acceptors 3, shown in the following structural formula:
Synthetic 3 is two saccharide donors of the allylic glucose in position with similar method; promptly use 3-O-allyl group-2; 4, the glycosyl donor 4 of 6-three-O-acyl-alpha--D-glucose makes itself and monose acceptor 5 under Louis acid catalysis; coupling obtains corresponding 1 under the stirring at room; the disaccharide of 3-β-connection, optionally hydrolysis fall 1 to anisole, it is activated; obtain two saccharide donors 6
Shown in the following structural formula:
With etc. two saccharide donors 6 of mol ratio and two saccharide acceptors 3 under Louis acid catalysis, coupling under the stirring at room obtains 1,3-β-and 1,4 sugar of 3-α-alternately connect, optionally 3 allyl group is fallen in hydrolysis, promptly obtains tetrose acceptor 7, shown in the following structural formula:
With etc. two saccharide donors 6 and the tetrose acceptor 7 of mol ratio under Louis acid catalysis, coupling under the stirring at room obtains 1,3-β-and 1, six sugar 8 of the protection of 3-α-alternately connect go protection promptly to obtain needed six sugar 9 again.Shown in the following structural formula:
With identical method, the disaccharide that connects with α-1 → 3-is donor and acceptor, can prepare α-Glu-1 → 3-β-Glu-1 → 3-α-Glu-1 → 3-β-Glu-1 → 3-α-Glu-1 → 3-Glu-OC easily
12H
25Use similar method, can synthesize pentasaccharides, seven sugar, eight sugar, nine sugar etc.
Described oligosaccharides, non-sugared body are divided into alkyl such as alkyl, thiazolinyl, aryl, and its carbon chain lengths is 1-20, preferably 6-12; Non-sugared body portion also can be amino acid and peptide chain,
Described acyl group is a benzoyl, ethanoyl or other acyl group.
Described Lewis acid is silver salt such as silver carbonate, silver trifluoromethanesulfonate, or is boron trifluoride, or is the trifluoromethanesulfonic acid trimethylsilyl group.
3. one kind has antivirally, anti-infective, antitumor and improve the oligosaccharides and the sulfation product thereof of pharmacological actions such as immunizing power, and it is characterized in that: the degree of the sulfovinic acidization of the oligose sulfate product described in the right 1 is greater than 1/5, preferably 1/3-2/3.
Oligose sulfate product described in oligosaccharides described in the right 1 and the right 3 can be separately with or share with other material, as antiviral, anti-infective, antitumor and improve the healthcare products or the medicine of immunizing power.
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| CN100338084C (en) * | 2004-07-02 | 2007-09-19 | 北京大学 | Synthetic method for pentose antigen for inhibiting heterogenic organ transplant immune rejection reaction |
| CN103788141A (en) * | 2004-03-04 | 2014-05-14 | 普罗吉恩制药有限公司 | Sulfated oligosaccharide derivatives |
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| CN105017346A (en) * | 2015-07-02 | 2015-11-04 | 中国农业大学 | 3,6-branched mannopentaose and hexaose on methoxy phenyl glycoside and preparation method and application thereof |
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| CN104119404A (en) * | 2004-03-04 | 2014-10-29 | 普罗吉恩制药有限公司 | Sulfated oligosaccharide derivatives |
| CN103788141B (en) * | 2004-03-04 | 2016-08-17 | 普罗吉恩制药有限公司 | Sulfated oligosaccharide derivatives |
| CN100338084C (en) * | 2004-07-02 | 2007-09-19 | 北京大学 | Synthetic method for pentose antigen for inhibiting heterogenic organ transplant immune rejection reaction |
| JP2015164947A (en) * | 2007-10-16 | 2015-09-17 | プロジェン ファーマシューティカルズ リミテッド | Novel sulfated oligosaccharide derivatives |
| USRE46955E1 (en) | 2007-10-16 | 2018-07-17 | Progen Pg500 Series Pty Ltd | Sulfated oligosaccharide derivatives |
| CN105017346A (en) * | 2015-07-02 | 2015-11-04 | 中国农业大学 | 3,6-branched mannopentaose and hexaose on methoxy phenyl glycoside and preparation method and application thereof |
| CN105017346B (en) * | 2015-07-02 | 2017-09-12 | 中国农业大学 | Three or six branched sugared p-methoxyphenyl glucosides of mannopentaose six and preparation method and application |
| CN108096273A (en) * | 2017-11-27 | 2018-06-01 | 浙江工业大学 | The application of Glucose sulfate aldehydic acid oligosaccharides |
| CN108096273B (en) * | 2017-11-27 | 2021-02-02 | 浙江工业大学 | Application of sulfated glucuronic acid oligosaccharide |
| CN108210504A (en) * | 2017-12-27 | 2018-06-29 | 中国科学院海洋研究所 | The application of sulphation galactooligosacchari(es and pharmaceutical composition |
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