CN1568966A - Usage of baicalin and its derivatives, analogs in the preparation process of tumor resisting medicine - Google Patents

Usage of baicalin and its derivatives, analogs in the preparation process of tumor resisting medicine Download PDF

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CN1568966A
CN1568966A CN 200410018368 CN200410018368A CN1568966A CN 1568966 A CN1568966 A CN 1568966A CN 200410018368 CN200410018368 CN 200410018368 CN 200410018368 A CN200410018368 A CN 200410018368A CN 1568966 A CN1568966 A CN 1568966A
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baicaligenin
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preparation
baicalin
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CN1267093C (en
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吴一心
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Shanghai Geluoli Biology Medicine Technology Co Ltd
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Abstract

The invention relates to baicalin and its derivatives, analogs, and the usage of baicalin and its derivatives, analogs in the preparation process of tumor resisting medicine.

Description

Baicaligenin and derivant thereof, the purposes of analog in the preparation antitumor drug
Technical field
The present invention relates to the pharmaceutical applications of a kind of baicaligenin and derivant thereof, analog, be specifically related to baicaligenin and derivant thereof, the purposes of analog in the preparation antitumor drug.
Background technology
Baikal skullcap root (Scutellaria baicalensis Georgi) head is stated from " (Sheng Nong's herbal classic ", has another name called Huang Wen, no a kind of reed mentioned in ancient books etc.Its pharmacological effect bitter in the mouth, cold in nature, function let out excess-fire, it is damp and hot to remove, and has effects such as antibacterial, heat extraction, detoxifcation, calmness, blood pressure lowering, function of gallbladder promoting.
Baicalin and baicaligenin are main flavone compounds contained in the Radix Scutellariae, and both have common flavone precursor structure:
Baicaligenin is one of main active of Radix Scutellariae.Molecular weight 270.25 can be got by the baicalin hydrolysis.Its chemical constitution is: 5,6,7 three hydrogen base-H are replaced by hydroxyl-OH on the flavone precursor structure.
The chemical constitution of baicalin is: 5,6 two hydrogen base-H are replaced by hydroxyl-OH on the flavone precursor structure, go up hydroxyl-OH and glucuronic acid condensation, i.e. baicaligenin-7-O-glucuronic acid for 7.
Bibliographical information is arranged in recent years, and baicalin and baicaligenin are to the growth of the breast cancer cell of In vitro culture inhibited (So F.V, et al.Cancer Lett., 112:127-133,1997).Also there are patent documentation report baicalin and baicaligenin that esophageal carcinoma and stomach cancer cell are had clearly lethal effect (Chinese patent application number 03109933.5; Chinese patent application number 03109942.4).
Do not see relevant baicalin and baicaligenin report so far to the active anticancer of other cancer strains.
Summary of the invention
Purpose of the present invention is intended to seek and develop the new medical usage of baicaligenin, its derivant, analog and their prodrug, officinal salt, and a kind of baicaligenin and derivant thereof, analog and their prodrug, the purposes of officinal salt in the preparation antitumor drug are provided.
The present invention relates to the baicaligenin shown in the following general formula (I), its derivant, analog and their prodrug, the purposes of officinal salt in the preparation antitumor drug:
Wherein, R 1Represent hydrogen, C 1～C 10Alkyl, C 1～C 10Thiazolinyl, C 1～C 10Alkynyl or glucose aldehyde radical, R 2, R 3Represent hydrogen, C separately 1～C 10Alkyl, C 1～C 10Thiazolinyl or C 1～C 10Alkynyl.
The inventor finds that after deliberation the chemical compound of following general formula (I) or its prodrug, officinal salt can obviously suppress the activity of kinds of tumor cells, so can be used for preparing antitumor drug:
Wherein, R 1Represent hydrogen, C 1～C 10Alkyl, C 1～C 10Thiazolinyl, C 1～C 10Alkynyl or glucose aldehyde radical, R 2, R 3Represent hydrogen, C separately 1～C 10Alkyl, C 1～C 10Thiazolinyl or C 1～C 10Alkynyl.
Particularly, work as R 1, R 2, R 3When representing hydrogen separately, described chemical compound is a baicaligenin, and described tumor includes but not limited to: leukemia, pulmonary carcinoma, hepatocarcinoma, cervical cancer, renal carcinoma or colorectal cancer.
Work as R 1Represent the glucose aldehyde radical, R 2, R 3When representing hydrogen separately, described chemical compound is a baicalin, and described tumor includes but not limited to: leukemia, pulmonary carcinoma, hepatocarcinoma, cervical cancer, renal carcinoma or colorectal cancer.
Above-claimed cpd all can extract from Radix Scutellariae or obtains by commercial sources by the conventional method of this area.
The officinal salt of chemical compound of the present invention comprises various inorganic or acylate example hydrochloric acid salt, hydrobromate, phosphate, sulfate, citrate, lactate, tartrate, maleate, fumarate, mandelate and oxalates; (TRIS is tromethane) with N-methyl-glucamine for various inorganic or organic alkali salts such as sodium hydroxide, Tris.
The prodrug of chemical compound of the present invention comprises that the carboxylate that contains this chemical compound (can be by the conventional method C of this area 1-4Pure and strong contraction get), the hydroxy ester that contains this chemical compound (can be by the conventional method C of this area 1-4Carboxylic acid, C 3-6Dicarboxylic acids or its anhydride, as maleic anhydride, fumaric acid anhydride etc. are concentrated to be made), the enamine that contains this chemical compound (can be by the conventional method C of this area 1-4Aldehydes or ketones concentrate make) or contain the acetal of this chemical compound or ketal (can concentrate with chloromethyl methyl ether or chloromethyl ether by the conventional method of this area and make) etc. (Albert S.Kearney Advanced Drug Reviews.19 (1996): 229-234)..
Baicaligenin of the present invention, baicalin and derivant thereof, analog can use separately or use with the form of pharmaceutical composition.Pharmaceutical composition comprises baicaligenin, baicalin and derivant thereof, analog and the pharmaceutically suitable carrier as active ingredient.
Described pharmaceutically suitable carrier is various excipient substances commonly used such as filler (Lactis Anhydrous, starch, lactose beadlet, glucose), binding agent (microcrystalline Cellulose), disintegrating agent (crosslinked carboxymethyl fecula sodium, cross-linking sodium carboxymethyl cellulose, low-substituted hydroxypropyl cellulose, cross-linked pvp), lubricant (magnesium stearate) and absorption enhancer, absorption carrier, flavouring agent, sweeting agent, diluent, excipient, wetting agent etc.
Described pharmaceutical composition can and can pass through intestinal or non-intestinal or topical routes by the preparation of this area conventional method.Oral formulations comprises tablet, granule, capsule, suspension, solution etc., and non-intestinal drug delivery agent comprises injection; Local administration preparation comprises as cream, ointment, patch, spray etc.
The route of administration of described medicine can be oral, Sublingual, subcutaneous, muscle, mucosa, urethra, vagina, vein etc.
The consumption of baicaligenin of the present invention, baicalin and derivant thereof, analog or its pharmaceutical composition can be according to route of administration, patient's age and body weight, the difference of the tumor type for the treatment of and the order of severity and difference, its daily dose can be 0.001～100mg/kg, can be in single or divided doses.
The specific embodiment
The invention will be further described below in conjunction with specific embodiment.But and do not mean that the present invention only limits to this.
Embodiment 1 baicalin and baicaligenin are tested the tumor cell in vitro Growth Inhibition
Be subjected to the reagent thing: baicalin and baicaligenin (existing goods) are dissolved in dimethyl sulfoxide (DMSO), use by 1/1000 dilution during actual the test.
The positive control medicine: 5-fluorouracil, be dissolved in DMSO, use by 1/1000 dilution during actual the test.
Method and result:
Determine baicalin and baicaligenin by the MTT algoscopy propagation of human lung carcinoma cell line A549, human leukemia cell line HL60, human cervical carcinoma cell strain Hela, human large intestine cancer cell strain HCT116, human hepatoma cell strain HepG2, human renal carcinoma cell strain RXF-631L is suppressed to measure each IC50 concentration, and the IC50 concentration of positive control medicine 5-fluorouracil.Simultaneously in contrast with people's normal fiber cell.
Assay method:
Above-mentioned each cell strain is suspended in the cell culture fluid that contains 10% (little) fetal bovine serum, with 2 * 10 4/ hole is seeded in 96 porocyte culture plates.After cultivating 24 hours, add baicalin or baicaligenin in culture fluid, ultimate density baicaligenin 0.3-200 μ g/ml, baicalin 0.6-350 μ g/ml, 5-fluorouracil 0.01-10 μ g/ml.Cultivate and make MTT mensuration after 3 days.With each cell of not adding baicalin and baicaligenin in contrast, test out each tumor cell 50% increased and stop concentration (IC50).
The results are shown in Table 1
Table 1
Cell category Baicalin IC50 concentration (μ M) Baicaligenin IC50 concentration (μ M) 5-fluorouracil IC50 concentration (μ M)
Human renal carcinoma cell strain RXF-631L ????35.1 ????19.2 ????2
Human cervical carcinoma cell strain Hela ????55.2 ????18.5 ????8
Human hepatoma cell strain HepG2 ????50.5 ????20.2 ????5
Human lung carcinoma cell line A549 ????45.3 ????25.5 ????2
Human leukemia cell line HL60 ????8 ????5 ????0.6
Human large intestine cancer cell strain HCT116 ????28.7 ????15，7 ????2
People's normal fiber cell ????＞1000 ????＞1000 ????10
The result shows that baicalin and baicaligenin are all had clearly inhibitory action to trying tumor cell.And compare with positive control medicine 5-fluorouracil, baicalin and baicaligenin do not have any toxic action to people's normal fiber cell.
Embodiment 2 baicaligenins suppress to be implanted in the growth of pulmonary carcinoma on the living animal
Experiment material: the BALB/cnu/nu Mus, male, 6 weeks are big, and body weight is about 20 grams.
Be subjected to the reagent thing: baicaligenin (existing goods) is dissolved in glycofurol and uses.
Experimental technique and result:
Earlier under the BALB/cnu/nu Corium Mus that the human lung cancer cell A549 is inoculated in, and with animal be divided into matched group and height (20mg/kg), in (10mg/kg), low (5mg/kg) dosage group and positive drug group, 6 every group.To inject the animal abdominal cavity to be dissolved in glycofurol baicaligenin 0.1ml after inoculating for two weeks, injection in per four days once.Take out lump 5-7 day after being to inject for the third time and measure volume.Average external volume and administration group with matched group are compared.
The assay method of gross tumor volume; { minor axis 2* major diameter } * 0.5
Tumor minification={ 1-(average external volume of the average external volume/matched group of administration group) } * 100%
The results are shown in Table 2
Table 2
Tumor minification %
Matched group 0
Low dose group 15
Middle dosage group 32
High dose group 62
Table 2 shows that baicaligenin has tangible inhibitory or killing effect to transplanting lung carcinoma cell, and is wherein obvious with high dose group.
Embodiment 3 baicaligenins suppress to be implanted in the growth of colorectal cancer on the living animal
Experiment material: the BALB/cnu/nu Mus, male, 6 weeks are big, and body weight is about 20 grams.
Be subjected to the reagent thing: baicaligenin (existing goods) is dissolved in glycofurol.
Experimental technique and result:
Earlier under the BALB/cnu/nu Corium Mus that human large intestine cancer cell HCT116 is inoculated in, and with animal be divided into matched group and height (20mg/kg), in (10mg/kg), low (5mg/kg) dosage group, 6 every group.To inject the animal abdominal cavity to be dissolved in glycofurol baicaligenin 0.1ml after inoculating for two weeks, injection in per four days once.Take out lump 5-7 day after being to inject for the third time and measure volume.Average external volume and administration group with matched group are compared.
The assay method of gross tumor volume; { minor axis 2* major diameter } * 0.5
Tumor minification={ 1-(average external volume of the average external volume/matched group of administration group) } * 100%
The results are shown in Table 3
Table 3
Tumor minification %
Matched group 0
Low dose group 29
Middle dosage group 40
High dose group 68
Table 3 shows that baicaligenin has tangible inhibitory or killing effect to transplanting colorectal cancer cells, and is wherein obvious with high dose group.
Embodiment 4 baicaligenins suppress to be implanted in the growth of hepatocarcinoma on the living animal
Experiment material; The BALB/cnu/nu Mus, male, 6 weeks are big, and body weight is about 20 grams.
Be subjected to the reagent thing; Baicaligenin (existing goods) is dissolved in glycofurol.
Experimental technique and result;
Earlier under the BALB/cnu/nu Corium Mus that human liver cancer cell HepG2 is inoculated in, and with animal be divided into matched group and height (20mg/kg), in (10mg/kg), low (5mg/kg) dosage group, 6 every group.To inject the animal abdominal cavity to be dissolved in glycofurol baicaligenin 0.1ml after inoculating for two weeks, injection in per four days once.Take out lump 5-7 day after being to inject for the third time and measure volume.Average external volume and administration group with matched group are compared.
The assay method of gross tumor volume; { minor axis 2* major diameter } * 0.5
Tumor minification={ 1-(average external volume of the average external volume/matched group of administration group) } * 100%
The results are shown in Table 4
Table 4
Tumor minification %
Matched group 0
Low dose group 18
Middle dosage group 32
High dose group 65
Table 4 shows that baicaligenin has tangible inhibitory or killing effect to the liver transplantation cancerous cell, and is wherein obvious with high dose group.
Embodiment 5 baicaligenins suppress to be implanted in the growth of cervical cancer on the living animal
Experiment material: the BALB/cnu/nu Mus, male, 6 weeks are big, and body weight is about 20 grams.
Be subjected to the reagent thing: baicaligenin (existing goods) is dissolved in glycofurol.
Experimental technique and result:
Earlier under the BALB/cnu/nu Corium Mus that human cervical carcinoma cell strain Hela is inoculated in, and with animal be divided into matched group and height (20mg/kg), in (10mg/kg), low (5mg/kg) dosage group, 6 every group.To inject the animal abdominal cavity to be dissolved in glycofurol baicaligenin 0.1ml after inoculating for two weeks, injection in per four days once.Take out lump 5-7 day after being to inject for the third time and measure volume.Average external volume and administration group with matched group are compared.
The assay method of gross tumor volume: { minor axis 2* major diameter } * 0.5
Tumor minification={ 1-(average external volume of the average external volume/matched group of administration group) } * 100%
The results are shown in Table 5
Table 5
Tumor minification %
Matched group 0
Low dose group 20
Middle dosage group 35
High dose group 69
The shown baicaligenin of table 5 has tangible inhibitory or killing effect to the transplanted kidney cancerous cell, and is wherein obvious with high dose group.
Embodiment 6 baicaligenins suppress to be implanted in the growth of renal carcinoma on the living animal
Experiment material: the BALB/cnu/nu Mus, male, 6 weeks are big, and body weight is about 20 grams.
Be subjected to the reagent thing: baicaligenin (existing goods) is dissolved in glycofurol.
Experimental technique and result:
Earlier under the BALB/cnu/nu Corium Mus that human renal carcinoma cell strain RXF-631L is inoculated in, and animal is divided into (10mg/kg) low (5mg/kg) dosage group in matched group and the height (20mg/kg), 6 every group.To inject the animal abdominal cavity to be dissolved in glycofurol baicaligenin 0.1ml after inoculating for two weeks, injection in per four days once.Take out lump 5-7 day after being to inject for the third time and measure volume.Average external volume and administration group with matched group are compared.
The assay method of gross tumor volume: { minor axis 2* major diameter } * 0.5
Tumor minification={ 1-(average external volume of the average external volume/matched group of administration group) } * 100%
The results are shown in Table 6
Table 6
Tumor minification %
Matched group 0
Low dose group 19
Middle dosage group 36
High dose group 69
Table 6 shows that baicaligenin has tangible inhibitory or killing effect to the transplanted kidney cancerous cell, and is wherein obvious with high dose group.
Embodiment 7 baicaligenins suppress to be implanted in the growth of leukaemia on the living animal
Experiment material: the BALB/cnu/nu Mus, male, 6 weeks are big, and body weight is about 20 grams.
Be subjected to the reagent thing: baicaligenin (existing goods) is dissolved in glycofurol.
Experimental technique and result:
Earlier with leukaemia HL601 * 10 8Be inoculated in the intraperitoneal of BALB/cnu/nu Mus, inoculate after 48 hours, with animal be divided into matched group and height (20mg/kg), in (10mg/kg), low (5mg/kg) dosage group, 6 every group.To be dissolved in glycofurol baicaligenin 0.1ml and inject the animal intraperitoneal.Injection in per four days is once injected three times altogether.The average survival time number of days and administration group with matched group are compared.
Life-delaying rate (ILS)=(the The average survival time number of days of the The average survival time number of days/matched group of administration group) * 100%
The results are shown in Table 7
Table 7
?ILS％
Matched group
Low dose group 120
Middle dosage group 150
High dose group 180
Table 7 shows that baicaligenin has the prolongation effect to the existence of transplanting the leukaemia Mus, and its result shows that baicaligenin has tangible leukemia resisting action.

Claims (9)

1. the chemical compound of following general formula (I) or its prodrug, the purposes of officinal salt in the preparation antitumor drug:
Figure A2004100183680002C1
Wherein, R 1Represent hydrogen, C 1～C 10Alkyl, C 1～C 10Thiazolinyl, C 1～C 10Alkynyl or glucose aldehyde radical, R 2, R 3Represent hydrogen, C separately 1～C 10Alkyl, C 1～C 10Thiazolinyl or C 1～C 10Alkynyl;
Described tumor is selected from leukemia, pulmonary carcinoma, hepatocarcinoma, cervical cancer, renal carcinoma or colorectal cancer.
2. the purposes of claim 1 is wherein worked as R 1, R 2, R 3When representing hydrogen separately, described chemical compound is a baicaligenin.
3. the purposes of claim 1 is wherein worked as R 1Represent the glucose aldehyde radical, R 2, R 3When representing hydrogen separately, described chemical compound is a baicalin.
4. baicaligenin is in the purposes of preparation in the anti-leukemia medicine.
5. baicaligenin is in the purposes of preparation in the anti-lung-cancer medicament.
6. baicaligenin is in the purposes of preparation in the medicines resistant to liver cancer.
7. baicaligenin is in the purposes of preparation in the medicament for resisting cervical cancer.
8. baicaligenin is in the purposes of preparation in the anti-renal carcinoma medicine.
9. the purposes of baicaligenin in preparation Chinese People's Anti-Japanese Military and Political College bowelcancer medicine.
CN 200410018368 2004-05-14 2004-05-14 Usage of baicalin and its derivatives, analogs in the preparation process of tumor resisting medicine Expired - Fee Related CN1267093C (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104586873A (en) * 2015-01-28 2015-05-06 苏州大学 Application of oroxin A in preparation of medicines for treating cancer
CN106336402A (en) * 2016-08-19 2017-01-18 福州大学 Baicalein derivative and preparation method thereof
CN113350329A (en) * 2020-03-06 2021-09-07 南京施江医药科技有限公司 Scutellaria compounds and application thereof in inhibiting mitochondrial oxidative phosphorylation pathway

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104586873A (en) * 2015-01-28 2015-05-06 苏州大学 Application of oroxin A in preparation of medicines for treating cancer
CN104586873B (en) * 2015-01-28 2017-08-25 苏州大学 Application of the oroxin A in treating cancer medicine is prepared
CN106336402A (en) * 2016-08-19 2017-01-18 福州大学 Baicalein derivative and preparation method thereof
CN113350329A (en) * 2020-03-06 2021-09-07 南京施江医药科技有限公司 Scutellaria compounds and application thereof in inhibiting mitochondrial oxidative phosphorylation pathway
WO2021175333A1 (en) * 2020-03-06 2021-09-10 南京施江医药科技有限公司 Scutellariae radix compounds and use thereof for inhibiting oxidative phosphorylation pathway of mitochondria

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