CN1448389A - L-amino acid acyl-( 8-quinolyl ) amine platinum (II) complex and prep. and use thereof - Google Patents
L-amino acid acyl-( 8-quinolyl ) amine platinum (II) complex and prep. and use thereof Download PDFInfo
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- CN1448389A CN1448389A CN03113344.4A CN03113344A CN1448389A CN 1448389 A CN1448389 A CN 1448389A CN 03113344 A CN03113344 A CN 03113344A CN 1448389 A CN1448389 A CN 1448389A
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- quinolyl
- amine
- acyl
- title complex
- platinum
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- 150000001412 amines Chemical class 0.000 title claims description 58
- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 title claims description 38
- 150000008575 L-amino acids Chemical class 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 24
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 14
- 239000004471 Glycine Substances 0.000 claims description 13
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims description 13
- 239000007864 aqueous solution Substances 0.000 claims description 10
- 229930182817 methionine Natural products 0.000 claims description 10
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 5
- 239000002246 antineoplastic agent Substances 0.000 claims description 4
- 229940041181 antineoplastic drug Drugs 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- 230000000694 effects Effects 0.000 abstract description 7
- 230000001093 anti-cancer Effects 0.000 abstract 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 31
- 210000004027 cell Anatomy 0.000 description 19
- 102000015782 Electron Transport Complex III Human genes 0.000 description 11
- 108010024882 Electron Transport Complex III Proteins 0.000 description 11
- 229960004452 methionine Drugs 0.000 description 9
- 229910052697 platinum Inorganic materials 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- 239000003814 drug Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 210000004881 tumor cell Anatomy 0.000 description 5
- 230000000259 anti-tumor effect Effects 0.000 description 4
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 231100000135 cytotoxicity Toxicity 0.000 description 3
- 230000003013 cytotoxicity Effects 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- 206010009944 Colon cancer Diseases 0.000 description 2
- FFEARJCKVFRZRR-UHFFFAOYSA-N L-Methionine Natural products CSCCC(N)C(O)=O FFEARJCKVFRZRR-UHFFFAOYSA-N 0.000 description 2
- 229930195722 L-methionine Natural products 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- 235000001014 amino acid Nutrition 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 208000029742 colonic neoplasm Diseases 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 201000006585 gastric adenocarcinoma Diseases 0.000 description 2
- 238000011005 laboratory method Methods 0.000 description 2
- 201000007270 liver cancer Diseases 0.000 description 2
- 208000014018 liver neoplasm Diseases 0.000 description 2
- 150000003057 platinum Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WREVVZMUNPAPOV-UHFFFAOYSA-N 8-aminoquinoline Chemical compound C1=CN=C2C(N)=CC=CC2=C1 WREVVZMUNPAPOV-UHFFFAOYSA-N 0.000 description 1
- 208000024893 Acute lymphoblastic leukemia Diseases 0.000 description 1
- 208000014697 Acute lymphocytic leukaemia Diseases 0.000 description 1
- 208000036762 Acute promyelocytic leukaemia Diseases 0.000 description 1
- 208000010507 Adenocarcinoma of Lung Diseases 0.000 description 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
- 206010029350 Neurotoxicity Diseases 0.000 description 1
- 206010034133 Pathogen resistance Diseases 0.000 description 1
- 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 description 1
- 208000033826 Promyelocytic Acute Leukemia Diseases 0.000 description 1
- 206010044221 Toxic encephalopathy Diseases 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000000118 anti-neoplastic effect Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 229960004562 carboplatin Drugs 0.000 description 1
- 190000008236 carboplatin Chemical compound 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 201000005249 lung adenocarcinoma Diseases 0.000 description 1
- 201000005202 lung cancer Diseases 0.000 description 1
- 208000020816 lung neoplasm Diseases 0.000 description 1
- 231100000417 nephrotoxicity Toxicity 0.000 description 1
- 231100000228 neurotoxicity Toxicity 0.000 description 1
- 230000007135 neurotoxicity Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- -1 nitrogen heterocyclic ring amide Chemical class 0.000 description 1
- 230000002611 ovarian Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Images
Abstract
The present invention is one kind of L-amino acyl-(8-quinolyl) amine-platinum (II) compound with anticancer cell activity. Their preparation process is also disclosed.
Description
One. technical field the present invention relates to platinum (II) title complex of L-amino acid acyl-(8-quinolyl) amine and derivative thereof.
Two. the background technology cis-platinum is the platinum series antineoplastic medicament that is widely used in the various cancers of treatment, but it has serious toxic side effect (as renal toxicity, neurotoxicity etc.) and secondary resistance, thereby its application is very limited.Though other platinum medicine after cis-platinum, occurred,,, be easy to generate cross-resistance because their structure is similar to cis-platinum as carboplatin and Ao Ke platinum etc.The structure of single function platinum (II) class title complex AAQPT and said medicine is obviously different, and has in the middle of them and much demonstrate higher anti-tumor activity, so is expected to therefrom filter out the antitumor drug of a kind of (class) high-efficiency low-toxicity.
Three. summary of the invention the present invention is a part with nitrogen heterocyclic ring amide ligands L-amino acid acyl-(8-quinolyl) amine and the derivative (general designation AAQ) thereof that 8-quinolylamine and derivative thereof and various different aminoacids condensation form, and has synthesized the novel single function platinum of a class (II) title complex AAQPT.Activity test in vitro shows that this class title complex shows very high cytotoxicity to different tumour cells, and therefore L-amino acid acyl of the present invention-(8-quinolyl) amine platinum (II) title complex can be used to prepare antitumor drug.
Technical scheme of the present invention is as follows:
One class L-amino acid acyl-(8-quinolyl) amine closes platinum (II) title complex, and they have following general structure:
Wherein
A＝H，CH
3，CH
2CH
2SCH
3
X＝N，S
The method that a kind of L-of preparation amino acid acyl-(8-quinolyl) amine closes platinum (II) title complex, it be with the acetone soln of glycine acyl-(8-quinolyl) amine, L-Ala acyl-(8-quinolyl) amine, methionine(Met) acyl-(8-quinolyl) amine or N '-tertbutyloxycarbonyl methionine(Met) acyl-(8-quinolyl) amine and etc. the K of amount of substance
2PtCl
4 Aqueous solution reflux 2～3 hours, cooling promptly gets glycine acyl of the present invention-(8-quinolyl) amine and closes that platinum (II) title complex, L-Ala acyl-(8-quinolyl) amine close platinum (II) title complex, methionine(Met) acyl-(8-quinolyl) amine closes platinum (II) title complex or N '-tertbutyloxycarbonyl methionine(Met) acyl-(8-quinolyl) amine closes platinum (II) title complex.
For N '-t-butoxycarbonyl glycine acyl-(8-quinolyl) amine or N '-tertbutyloxycarbonyl L-Ala acyl-(8-quinolyl) amine, they and K
2PtCl
4During reaction, tertbutyloxycarbonyl can be sloughed automatically, therefore, glycine acyl-(8-quinolyl) amine close platinum (II) title complex or L-Ala acyl-(8-quinolyl) amine close platinum (II) title complex also can following method preparation:
A kind of glycine acyl-(8-quinolyl) amine for preparing closes platinum (II) title complex or method that the L-Ala acyl-(8-quinolyl) amine closes platinum (II) title complex, it be with the acetone soln of N '-t-butoxycarbonyl glycine acyl-(8-quinolyl) amine or N '-tertbutyloxycarbonyl L-Ala acyl-(8-quinolyl) amine and etc. the K of amount of substance
2PtCl
4Aqueous solution reflux, cooling gets promptly that glycine acyl of the present invention-(8-quinolyl) amine closes platinum (II) title complex or L-Ala acyl-(8-quinolyl) amine closes platinum (II) title complex.
L-amino acid acyl of the present invention-(8-quinolyl) amine closes when platinum (II) title complex carries out the cell in vitro activity test and shows, they have tangible killing action to human liver cancer cell (BEL-7402), human colon cancer cell (HCT-116), the sick cell cancer cells such as (P-338) of mouse hundred blood, therefore, they can be applied to prepare anti-tumor drug.
Four, description of drawings
Fig. 1 is the X-ray crystalline diffraction structure iron of title complex II, part bond distance (_) and bond angle (°): Pt (1)-N (1) 2.009 (10), Pt (1)-N (2) 2.023 (10), Pt (1)-N (3) 1.954 (10), Pt (1)-Cl (1) 2.318 (3); N (1)-Pt (1)-N (3) 83.7 (4), N (1)-Pt (1)-Cl (1) 97.6 (3), N (2)-Pt (1)-N (3) 83.5 (4), N (2)-Pt (1)-Cl (1) 95.4 (3), N (3)-Pt (1)-Cl (1) 178.0 (3);
Fig. 2 is the X-ray crystalline diffraction structure iron of title complex III, part bond distance (_) and bond angle (°): Pt (1)-N (1) 2.032 (5), Pt (1)-N (2) 2.053 (5), Pt (1)-S (1) 2.278 (2), Pt (1)-Cl (1) 2.313 (2); N (1)-Pt (1)-N (2) 80.5 (2), N (1)-Pt (1)-Cl (1) 93.2 (2), N (2)-Pt (1)-S (1) 100.9 (2), N (2)-Pt (1)-Cl (1) 172.6 (2), S (1)-Pt (1)-Cl (1) 85.9 (7);
Fig. 3 is title complex I, II, the III IC to different clones
50Value;
Fig. 4 is the IC of title complex III to different clones
50Value.a：HCT-116；b：SPC-A4；c：BEL-7402；d：MOLT-4；e：HO-8910；f:P-388；g：HL-60；h?A-549；i：SGC-7901；j：MKN-28。
Four. embodiment
Universal method: with K
2PtCl
4The aqueous solution and the acetone soln of L-amino acid (N '-8-quinolyl) acid amides or derivatives thereof (general designation AAQ) with 1: 1 mixed in molar ratio, backflow 2h.Be cooled to room temperature and get title complex.Title complex slowly can get complex monocrystal after the volatilization with acetone and water dissolution, solvent.
The preparation that embodiment 1, N '-tertbutyloxycarbonyl methionine(Met) acyl-(8-quinolyl) amine closes platinum (II) title complex
With K
2PtCl
4The aqueous solution (0.2mmol, 2ml) with the acetone soln (0.2mmol of N '-tertbutyloxycarbonyl-L-methionine(Met) acyl-(8-quinolyl) amine, 2ml) ratio with 1: 1 amount of substance mixes, mixture backflow 2h, be cooled to room temperature, filter to such an extent that yellow N '-tertbutyloxycarbonyl methionine(Met) acyl-(8-quinolyl) amine closes platinum (II) title complex (III) precipitation.Title complex precipitates with acetone and water dissolution, can get the monocrystalline of title complex III after solvent slowly volatilizees.
Part is used L-methionine(Met) acyl-(8-quinolyl) amine of protecting group instead, can make L-methionine(Met) acyl-(8-quinolyl) amine with same procedure and close platinum (II) title complex.
Be the structural characterization data of title complex I, II and III below.
In the ultimate analysis data of title complex I, bracket is calculated value (%): C, 29.0 (29.4); H, 2.63 (2.68); N, 9.39 (9.36).Title complex I is at D
6Among-the DMSO
1H nuclear magnetic data (ppm): 8.99 (d, 1H), 8.68 (d, 1H), 8.58 (d, 1H), 7.69 (m, 1H), 7.57 (t, 1H), 7.50 (d, 1H), 6.00 (s, 2H).
In the ultimate analysis data of title complex II, bracket is calculated value (%): C, 30.8 (31.1); H, 3.00 (3.03); N, 9.13 (9.08).Title complex II is at D
6Among-the DMSO
1H nuclear magnetic data (ppm): 9.01 (d, 1H), 8.67 (d, 1H), 8.60 (d, 1H), 7.70 (m, 1H), 7.57 (t, 1H), 7.50 (d, 1H), 3.81 (q, 1H), 1.33 (d, 3H).
In the ultimate analysis data of title complex III, bracket is calculated value (%): C, 32.0 (32.2); H, 3.40 (3.44); N, 8.07 (8.04).Title complex III is at CDCl
3In
1H nuclear magnetic data (ppm): at CDCl
3In have two groups
1The H nuclear magnetic data, 1 group: 9.365 (d, 1H), 8.735 (d, 1H), 8.426 (t, 1H), 8.638 (m, 1H), 7.572 (m, 1H), 7.495 (m, 1H), 6.002 (m, 1H), 3.425 (m, 1H), 3.065 (m, 2H), 2.857 (s, 3H), 2.305 (m, 2H), 1.481 (s, 9H); 2 groups: 9.300 (d, 1H), 8.645 (d, 1H), 8.426 (t, 1H), 8.638 (m, 1H), 7.572 (m, 1H), 7.495 (m, 1H), 6.656 (m, 1H), 3.114 (m, 1H), 2.620 (m, 2H), 2.761 (s, 3H), 2.171 (m, 2H), 1.481 (s, 9H).
The X-ray crystalline diffraction structure iron of title complex II and III is seen Fig. 1 and Fig. 2.
The crystal data of table 1. title complex II and III
Compound title complex II title complex III
Empirical formula C
12H
14ClN
3O
2Pt C
19H
24ClN
3O
3PtS molecular weight 462.8 605.01
Temperature/K 293 (2) 293 (2) crystallographic dimensions/mm 0.30 * 0.10 * 0.10 0.35 * 0.05 * 0.02
Crystallographic system monocline quadrature
Spacer P2 (1) P2 (1) 2 (1) 2 (1)
a/_????????????????9.502(2)?????????????????5.441(1)
b/A?????????????????4.724(1)?????????????????12.978(3)
c/_????????????????14.800(3)????????????????29.438(6)
α/°???????????????????????????????????90.00?????????????????????90
β/°?????????????????????????????????95.17(3)???????????????????90
γ/°????????????????????????????????????90.00?????????????????????90
V/_
3??????????????661.7(2)?????????????????2078.9(7)
Z?????????????????????2?????????????????????????4
D
Calcd/ gcm
-32.323 the anti-tumor biological of 1.933 embodiment 4, title complex:
Single function platinum complexes AAQPT shows very high cytotoxicity to different tumour cells.Provide part title complex I, II and III cell in vitro activity test result (table 2) below to human liver cancer cell (BEL-7402), human colon cancer cell (HCT-116), mouse leukemia cell (P-388), people's acute promyelocytic leukemia cell (HL-60) and people's lung cancer in non-cellule type cell (A-549).Table 2. title complex I, II, III under different concns (μ g/ml) to the cytotoxicity of part tumour cell, with inhibiting rate
Express (%).
*With the test of SRB laboratory method, cell and medicine are cultivated 72h.
*With the test of MTT laboratory method, cell and medicine are cultivated 48h.
| Tumour cell | ?????????????? The concentration of title complex I??10??????3.3?????1.1?????0.4??????0.1 | ???????? The concentration of title complex II??10??????3.3????1.1????0.4????0.1 | ???????????? The concentration of title complex III??10???????3.3????1.1?????0.4?????0.1 |
| ????BEL-7402 *????HCT-116 *????P-388 **????HL-60 **????A-549 * | ??84.5????92.6????18.3????12.6?????4.1 ??95.5????88.9????21.3????5.7??????28.3 ??86.2????64.2????25.7????15.6?????9.6 ??100?????61.5?????0???????0????????0 ??95.3????58.7????7.6??????0????????0 | ??83.5????94?4???45.4???0.4????0 ??97.0????84.6????0??????0?????0 ??73.7????58.1????0??????0?????0 ??100?????57.4????0??????0?????0 ??92.2????51.7???2.5?????0?????0 | ??89?3????93.2????90.9????75.1????13.9 ??97.5????96.3????92.4????30.4????45.5 ??85.9????52.3????45.2????15.4????13.2 ??98.7????89.6????21.0????4.0?????0.6 ??94.2????75?9????8.1??????0???????0 |
Title complex III has the activity similar or higher with cis-platinum to BEL-7402 and P-388.
Title complex I, II and III are to the IC of these cells
50Value as shown in Figure 3.
Except that above-mentioned clone, title complex III is to the IC of more tumour cells
50Be worth as shown in Figure 4, comprising human lung adenocarcinoma cell (SPC-A4), people's acute lymphoblastic leukemia cell (MOLT-4), Proliferation of Human Ovarian Cell (HO-8910), people's adenocarcinoma of stomach cell (SGC-7901) and people's adenocarcinoma of stomach cell (MKN-28).
Title complex III is higher nearly 6 times than cis-platinum to the anti-tumor activity of BEL-7402, but cis-platinum is to P-388, the IC of A-549 and HL-60
50Value (μ M) is respectively 0.38,0.54 and 0.87, specific activity title complex III height.Because the structure difference of two kinds of compounds, antitumor mechanism are also different, therefore do not have comparability completely, are incorporated herein partial data usefulness only for referencial use.
Claims (4)
1, a class L-amino acid acyl-(8-quinolyl) amine closes platinum (II) title complex, it is characterized in that they have following general structure:
Wherein
A＝H，CH
3，CH
2CH
2SCH
3
X＝N，S
2, a kind ofly prepare the method that the described L-amino acid of claim 1 acyl-(8-quinolyl) amine closes platinum (II) title complex, it is characterized in that: with the acetone soln of glycine acyl-(8-quinolyl) amine, L-Ala acyl-(8-quinolyl) amine, methionine(Met) acyl-(8-quinolyl) amine or N '-tertbutyloxycarbonyl methionine(Met) acyl-(8-quinolyl) amine and etc. the K of amount of substance
2PtCl
4Aqueous solution reflux 2～3 hours, cooling promptly gets glycine acyl of the present invention-(8-quinolyl) amine and closes that platinum (II) title complex, L-Ala acyl-(8-quinolyl) amine close platinum (II) title complex, methionine(Met) acyl-(8-quinolyl) amine closes platinum (II) title complex or N '-tertbutyloxycarbonyl methionine(Met) acyl-(8-quinolyl) amine closes platinum (II) title complex.
3, a kind of described glycine acyl of claim 1-(8-quinolyl) amine for preparing closes platinum (II) title complex or method that the L-Ala acyl-(8-quinolyl) amine closes platinum (II) title complex, it is characterized in that: with the acetone soln of N '-t-butoxycarbonyl glycine acyl-(8-quinolyl) amine or N '-tertbutyloxycarbonyl L-Ala acyl-(8-quinolyl) amine and etc. the K of amount of substance
2PtCl
4Aqueous solution reflux, cooling gets promptly that glycine acyl of the present invention-(8-quinolyl) amine closes platinum (II) title complex or L-Ala acyl-(8-quinolyl) amine closes platinum (II) title complex.
4, the described L-amino acid of claim 1 acyl-(8-quinolyl) amine closes the application of platinum (II) title complex in the preparation antitumor drug.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN03113344.4A CN1211369C (en) | 2003-04-30 | 2003-04-30 | L-amino acid acyl-( 8-quinolyl ) amine platinum (II) complex and prep. and use thereof |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN03113344.4A CN1211369C (en) | 2003-04-30 | 2003-04-30 | L-amino acid acyl-( 8-quinolyl ) amine platinum (II) complex and prep. and use thereof |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101891769A (en) * | 2010-06-18 | 2010-11-24 | 河北大学 | Anti-tumor platinum complexes |
| CN101239990B (en) * | 2007-02-07 | 2011-04-20 | 首都医科大学 | N-(2,3,4,5,6-pentahydroxyhexyl)-L-amino acid platinum ligand, preparation method and application thereof |
| CN101492539B (en) * | 2008-10-09 | 2011-11-16 | 北京联合大学 | Dichloro-platinum aspartate |
-
2003
- 2003-04-30 CN CN03113344.4A patent/CN1211369C/en not_active Expired - Fee Related
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101239990B (en) * | 2007-02-07 | 2011-04-20 | 首都医科大学 | N-(2,3,4,5,6-pentahydroxyhexyl)-L-amino acid platinum ligand, preparation method and application thereof |
| CN101492539B (en) * | 2008-10-09 | 2011-11-16 | 北京联合大学 | Dichloro-platinum aspartate |
| CN101891769A (en) * | 2010-06-18 | 2010-11-24 | 河北大学 | Anti-tumor platinum complexes |
| CN101891769B (en) * | 2010-06-18 | 2013-01-16 | 河北大学 | Anti-tumor platinum complexes |
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| Publication number | Publication date |
|---|---|
| CN1211369C (en) | 2005-07-20 |
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