CN105837619A - Triphenyltin parahydroxybenzoate ester complex and preparation method and application thereof - Google Patents
Triphenyltin parahydroxybenzoate ester complex and preparation method and application thereof Download PDFInfo
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- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- -1 Triphenyltin parahydroxybenzoate ester Chemical class 0.000 title abstract description 7
- 238000010668 complexation reaction Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 39
- VCAJGENTXYWRPX-UHFFFAOYSA-M triphenylstannyl 4-hydroxybenzoate Chemical compound C1=CC(O)=CC=C1C(=O)O[Sn](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 VCAJGENTXYWRPX-UHFFFAOYSA-M 0.000 claims description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- 239000003814 drug Substances 0.000 claims description 15
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 12
- 239000013078 crystal Substances 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 229940079593 drug Drugs 0.000 claims description 8
- 206010009944 Colon cancer Diseases 0.000 claims description 7
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 7
- BFWMWWXRWVJXSE-UHFFFAOYSA-M fentin hydroxide Chemical compound C=1C=CC=CC=1[Sn](C=1C=CC=CC=1)(O)C1=CC=CC=C1 BFWMWWXRWVJXSE-UHFFFAOYSA-M 0.000 claims description 7
- 238000011275 oncology therapy Methods 0.000 claims description 7
- QNRATNLHPGXHMA-XZHTYLCXSA-N (r)-(6-ethoxyquinolin-4-yl)-[(2s,4s,5r)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]methanol;hydrochloride Chemical compound Cl.C([C@H]([C@H](C1)CC)C2)CN1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OCC)C=C21 QNRATNLHPGXHMA-XZHTYLCXSA-N 0.000 claims description 6
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 claims description 6
- 206010006187 Breast cancer Diseases 0.000 claims description 6
- 208000026310 Breast neoplasm Diseases 0.000 claims description 6
- 208000019065 cervical carcinoma Diseases 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 6
- 238000002447 crystallographic data Methods 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 6
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 5
- 238000002425 crystallisation Methods 0.000 claims description 5
- 230000008025 crystallization Effects 0.000 claims description 5
- 208000029742 colonic neoplasm Diseases 0.000 claims description 4
- 201000008275 breast carcinoma Diseases 0.000 claims description 3
- 206010028980 Neoplasm Diseases 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 201000011510 cancer Diseases 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 abstract description 5
- 229940041181 antineoplastic drug Drugs 0.000 abstract description 5
- 210000004027 cell Anatomy 0.000 description 30
- 238000004458 analytical method Methods 0.000 description 9
- 230000001093 anti-cancer Effects 0.000 description 9
- 238000012360 testing method Methods 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 229910020813 Sn-C Inorganic materials 0.000 description 6
- 229910018732 Sn—C Inorganic materials 0.000 description 6
- 229910020923 Sn-O Inorganic materials 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 230000004071 biological effect Effects 0.000 description 4
- 201000007270 liver cancer Diseases 0.000 description 4
- 208000014018 liver neoplasm Diseases 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 201000005202 lung cancer Diseases 0.000 description 3
- 201000005296 lung carcinoma Diseases 0.000 description 3
- 208000020816 lung neoplasm Diseases 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000012531 culture fluid Substances 0.000 description 2
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 229960003742 phenol Drugs 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 230000001954 sterilising effect Effects 0.000 description 2
- 238000004659 sterilization and disinfection Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229910052718 tin Inorganic materials 0.000 description 2
- ASJSXUWOFZATJM-UHFFFAOYSA-N 2-(3,5-diphenyl-1h-tetrazol-2-yl)-4,5-dimethyl-1,3-thiazole Chemical compound S1C(C)=C(C)N=C1N1N(C=2C=CC=CC=2)NC(C=2C=CC=CC=2)=N1 ASJSXUWOFZATJM-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 206010008342 Cervix carcinoma Diseases 0.000 description 1
- 241001062009 Indigofera Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 239000012980 RPMI-1640 medium Substances 0.000 description 1
- 102000019259 Succinate Dehydrogenase Human genes 0.000 description 1
- 108010012901 Succinate Dehydrogenase Proteins 0.000 description 1
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 description 1
- 208000009956 adenocarcinoma Diseases 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 201000010881 cervical cancer Diseases 0.000 description 1
- 229920001795 coordination polymer Polymers 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 238000003255 drug test Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 210000004251 human milk Anatomy 0.000 description 1
- 235000020256 human milk Nutrition 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 210000003470 mitochondria Anatomy 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000007524 organic acids Chemical group 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- SBXWFLISHPUINY-UHFFFAOYSA-N triphenyltin Chemical compound C1=CC=CC=C1[Sn](C=1C=CC=CC=1)C1=CC=CC=C1 SBXWFLISHPUINY-UHFFFAOYSA-N 0.000 description 1
- 230000002476 tumorcidal effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/22—Tin compounds
- C07F7/2224—Compounds having one or more tin-oxygen linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention discloses a triphenyltin parahydroxybenzoate ester complex and a preparation method and application thereof. The complex has a following structural formula (1). The invention discloses the preparation method of the triphenyltin parahydroxybenzoate ester complex and application thereof to preparation of antitumor drugs.
Description
Technical field
The present invention relates to triphenyltin p-Hydroxybenzoate coordination compound, and preparation method thereof, and this coordination compound is in system
Application in standby antitumor drug.
Background technology
Organotin is the metallo-organic compound that a class contains Sn-C key, has higher biological activity, in sterilization, kills
Worm, cancer therapy drug the field such as are prepared and are had a wide range of applications.There are some researches show, the alkyl R in organotin is decisionization
The principal element of compound active anticancer, e.g., the active anticancer of cyclohexyl, normal-butyl and phenyltin compound is relatively strong, and ethyl takes second place,
Methyl is then almost without active anticancer.Active anticancer and the tumoricidal broad spectrum activity of organotin complex are also risen by the structure of part
Important effect, the biological activity of organotin carboxylate coordination compound is often high than corresponding organo-tin compound, such as: European patent
Disclosed in EP0177785B1, double [three (2-methyl-2-phenyl propyl) stannum] monocarboxylates are than double [three (2-methyl-2-phenyl third
Base) stannum] oxide has higher biological activity；Document (SCI, 2008,29 (9): 1781-1785.) is reported
Road, dibutyl tin carboxylate is significantly stronger than Dibutyltin oxide to the inhibitory activity of Gram-negative and positive bacteria, and relatively low
There is under concentration the function of tumor inhibition more higher than Dibutyltin oxide.Document (Chinese Journal of Inorganic Chemistry, 2011,27 (1): 107-
113.) proving, Tricyclohexyltin carboxylate has the sterilization more higher than tin tricyclohexylhydroxide, active anticancer, etc..
Being the material that the experiment proved that and have active anticancer based on organic tin compound, the present invention selects para hydroxybenzene first
Acid is organic acid part, reacts under certain condition with triphenyl tin hydroxide, and synthesis has obtained human colon cancer cell
(Colo205), human liver cancer cell (HepG2), human breast cancer cell (MCF7), human cervical carcinoma cell (Hela), human lung carcinoma cell
(NCI-H460) compound that inhibitory activity is stronger, provides new way for exploitation cancer therapy drug.
Summary of the invention
The problem existed for above-mentioned prior art, the first object of the present invention there is provided triphenyltin para hydroxybenzene first
Acid esters coordination compound.
The second object of the present invention is to provide the preparation method of above-mentioned triphenyltin p-Hydroxybenzoate coordination compound.
3rd mesh of the present invention is to provide above-mentioned triphenyltin p-Hydroxybenzoate coordination compound answering in preparing medicine
With.
In order to realize foregoing invention purpose, the technical solution adopted in the present invention is:
As the triphenyltin p-Hydroxybenzoate coordination compound of first aspect present invention, it is following structural formula (1)
Compound:
Wherein: Ph represents phenyl.
The triphenyltin p-Hydroxybenzoate coordination compound of the present invention is through elementary analysis, infrared spectrum analysis, nuclear magnetic resonance, NMR
Spectrum and x-ray crystal structure analysis, result is as follows:
Elementary analysis (C34H35O9Sn): theoretical value: C, 57.81；H, 5.00.Measured value: C, 57.85；H, 4.91.
IR(KBr,cm-1):3410v(O-H),3071,3049,905v(C-H),1607vas(COO-),1369vs(COO-),
550v(Sn-C),455v(Sn-O)。
The triphenyltin p-Hydroxybenzoate coordination compound of the present invention is crystal structure, its crystallographic data: rhombic system,
Space group Fdd2, a=3.7411 (2) nm, b=1.06477 (6) nm, c=1.75171 (10) nm, α=β=γ=90 °, Z=
8, V=6.9778 (7) nm3, Dc=1.345Mg m-3, μ (MoKa)=0.781mm-1, F (000)=2888,2.30 ° of ＜ θ ＜
27.54 °, crystalline size: 0.20x 0.19x 0.17mm, R=0.0318, wR=0.0838.
The triphenyltin p-Hydroxybenzoate coordination compound of the present invention, is structurally characterized in that: center tin atom and three carbon are former
Son and two oxygen atom ligands, define pentacoordinate distortion trigonal biyramid configuration.
As the preparation method of the triphenyltin p-Hydroxybenzoate coordination compound of second aspect present invention, at reaction vessel
In be sequentially added into P-hydroxybenzoic acid 1～3mmol, triphenyl tin hydroxide 0.5～1.5mmol, solvent absolute methanol in order
30～80mL, it is being stirred at reflux lower reaction 8～12h；Cooling, filters；Under the conditions of 25～35 DEG C, control solvent volatilization crystallization,
Obtain colourless transparent crystal, be triphenyltin p-Hydroxybenzoate coordination compound.
As the application in preparing medicine of the triphenyltin p-Hydroxybenzoate coordination compound of third aspect present invention, its
It it is the application in preparing antitumor drug.
Applicant has carried out anti tumor activity in vitro and has confirmed research above-mentioned coordination compound, confirms that this is joined and has antitumor with thing
Biological activity, say, that the purposes of above-mentioned coordination compound is the application in preparing antitumor drug, is exactly specifically in system
Application in standby inhibitor against colon carcinoma cells or hepatocarcinoma or breast carcinoma or human cervical carcinoma or lung-cancer medicament.
The triphenyltin p-Hydroxybenzoate coordination compound of the present invention, has preferable active anticancer, can be with it as raw material
Prepare inhibitor against colon carcinoma cells, anti-liver cancer and anti-, anti-breast cancer, anti-cervical cancer, anti-lung-cancer medicament.With the platinum-containing anticancer drug commonly used at present
Comparing, the organotin coordination polymeric compound of the present invention has the features such as active anticancer height, low cost, preparation method are simple, for exploitation
Cancer therapy drug provides new way.
Accompanying drawing explanation
Fig. 1 is triphenyltin p-Hydroxybenzoate complex crystal molecular structure.
Detailed description of the invention
Further describe the present invention by following example, but it should be noted that the scope of the present invention is not implemented by these
Any restriction of example.
Embodiment 1:
The preparation of triphenyltin p-Hydroxybenzoate coordination compound:
P-hydroxybenzoic acid 1mmol, triphenyl tin hydroxide 0.5mmol, molten it is sequentially added in order in round-bottomed flask
Agent absolute methanol 30mL, is being stirred at reflux lower reaction 8h；Cooling, filters；Under the conditions of 25～35 DEG C, control solvent volatilization knot
Crystalline substance, obtains colourless transparent crystal, is triphenyltin p-Hydroxybenzoate coordination compound.Productivity: 63%, fusing point: 162～164 DEG C.
Elementary analysis (C34H35O9Sn): theoretical value: C, 57.81；H, 5.00.Measured value: C, 57.85；H, 4.91.
IR(KBr,cm-1):3410v(O-H),3071,3049,905v(C-H),1607vas(COO-),1369vs(COO-),
550v(Sn-C),455v(Sn-O)。
Crystallographic data: rhombic system, space group Fdd2, a=3.7411 (2) nm, b=1.06477 (6) nm, c=
1.75171 (10) nm, α=β=γ=90 °, Z=8, V=6.9778 (7) nm3, Dc=1.345Mg m-3, μ (MoKa)=
0.781mm-1, F (000)=2888,2.30 ° of ＜ θ ＜ 27.54 °, crystalline size: 0.20x 0.19x 0.17mm, R=0.0318,
WR=0.0838.
Embodiment 2:
The preparation of triphenyltin p-Hydroxybenzoate coordination compound:
Round-bottomed flask is sequentially added in order P-hydroxybenzoic acid 1.6mmol, triphenyl tin hydroxide 0.8mmol,
Solvent absolute methanol 340mL, is being stirred at reflux lower reaction 9h；Cooling, filters；Under the conditions of 25～35 DEG C, control solvent volatilization
Crystallization, obtains colourless transparent crystal, is triphenyltin p-Hydroxybenzoate coordination compound.Productivity: 62%, fusing point: 162～164
℃。
Elementary analysis (C34H35O9Sn): theoretical value: C, 57.81；H, 5.00.Measured value: C, 57.85；H, 4.91.
IR(KBr,cm-1):3410v(O-H),3071,3049,905v(C-H),1607vas(COO-),1369vs(COO-),
550v(Sn-C),455v(Sn-O)。
Crystallographic data: rhombic system, space group Fdd2, a=3.7411 (2) nm, b=1.06477 (6) nm, c=
1.75171 (10) nm, α=β=γ=90 °, Z=8, V=6.9778 (7) nm3, Dc=1.345Mg m-3, μ (MoKa)=
0.781mm-1, F (000)=2888,2.30 ° of ＜ θ ＜ 27.54 °, crystalline size: 0.20x 0.19x 0.17mm, R=0.0318,
WR=0.0838.
Embodiment 3:
The preparation of triphenyltin p-Hydroxybenzoate coordination compound:
P-hydroxybenzoic acid 2mmol, triphenyl tin hydroxide 1mmol, solvent it is sequentially added in order in round-bottomed flask
Absolute methanol 60mL, is being stirred at reflux lower reaction 10h；Cooling, filters；Under the conditions of 25～35 DEG C, control solvent volatilization crystallization,
Obtain colourless transparent crystal, be triphenyltin p-Hydroxybenzoate coordination compound.Productivity: 65%, fusing point: 162～164 DEG C.
Elementary analysis (C34H35O9Sn): theoretical value: C, 57.81；H, 5.00.Measured value: C, 57.85；H, 4.91.
IR(KBr,cm-1):3410v(O-H),3071,3049,905v(C-H),1607vas(COO-),1369vs(COO-),
550v(Sn-C),455v(Sn-O)。
Crystallographic data: rhombic system, space group Fdd2, a=3.7411 (2) nm, b=1.06477 (6) nm, c=
1.75171 (10) nm, α=β=γ=90 °, Z=8, V=6.9778 (7) nm3, Dc=1.345Mg m-3, μ (MoKa)=
0.781mm-1, F (000)=2888,2.30 ° of ＜ θ ＜ 27.54 °, crystalline size: 0.20x 0.19x 0.17mm, R=0.0318,
WR=0.0838.
Embodiment 4:
The preparation of triphenyltin p-Hydroxybenzoate coordination compound:
P-hydroxybenzoic acid 3mmol, triphenyl tin hydroxide 1.5mmol, molten it is sequentially added in order in round-bottomed flask
Agent absolute methanol 80mL, is being stirred at reflux lower reaction 12h；Cooling, filters；Under the conditions of 25～35 DEG C, control solvent volatilization knot
Crystalline substance, obtains colourless transparent crystal, is triphenyltin p-Hydroxybenzoate coordination compound.Productivity: 64%, fusing point: 162～164 DEG C.
Elementary analysis (C34H35O9Sn): theoretical value: C, 57.81；H, 5.00.Measured value: C, 57.85；H, 4.91.
IR(KBr,cm-1):3410v(O-H),3071,3049,905v(C-H),1607vas(COO-),1369vs(COO-),
550v(Sn-C),455v(Sn-O)。
Crystallographic data: rhombic system, space group Fdd2, a=3.7411 (2) nm, b=1.06477 (6) nm, c=
1.75171 (10) nm, α=β=γ=90 °, Z=8, V=6.9778 (7) nm3, Dc=1.345Mg m-3, μ (MoKa)=
0.781mm-1, F (000)=2888,2.30 ° of ＜ θ ＜ 27.54 °, crystalline size: 0.20x 0.19x 0.17mm, R=0.0318,
WR=0.0838.
Test example: the triphenyltin p-Hydroxybenzoate coordination compound of the present invention, it is to pass through that its Anticancer Activity in vitro measures
MTT experiment method realizes.
MTT analyses method:
With metabolism reduction 3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazol
Based on iumbromide.Succinate dehydrogenase in living cells mitochondrion can make exogenous MTT be reduced to water-insoluble indigo plant
Purple crystal first a ceremonial jade-ladle, used in libation (Formazan) is also deposited in cell, and dead cell is without this function.Dimethyl sulfoxide (DMSO) can dissolve
First a ceremonial jade-ladle, used in libation in cell, measures the optical density of characteristic wavelength, can indirectly reflect living cells quantity by microplate reader.
Use mtt assay measure organotin coordination thing to human colon cancer cell (Colo205), human liver cancer cell (HepG2),
Human breast cancer cell (MCF7), human cervical carcinoma cell (Hela), the inhibitory activity of human lung carcinoma cell (H460).
Cell strain and cultivating system: Colo205, HepG2, MCF7, Hela and H460 cell strain is taken from American. tissue and cultivated
Storehouse (ATCC).By RPMI 1640 (GIBICO company) culture medium containing 10% hyclone, at 5% (volume fraction) CO2、37
In vitro culture is carried out in DEG C saturated humidity incubator.
Test process: test medicinal liquid (0.1nM-10uM) is added separately in each hole according to the Concentraton gradient of concentration,
Each concentration sets 6 parallel holes.Experiment is divided into drug test group (being separately added into the test medicine of variable concentrations), matched group (only to add
Culture fluid and cell, be not added with testing medicine) and blank group (only adding culture fluid, be not added with cell and test medicine).By the orifice plate after dosing
It is placed in 37 DEG C, 5%CO2Incubator is cultivated 72h.The activity of control drug measures according to the method for test sample.Cultivating
In orifice plate after 72h, every hole adds MTT40uL (being made into 4mg/mL with D-Hanks buffer).After placing 4h at 37 DEG C, remove
Clear liquid.Every hole adds 150uL DMSO, and vibrate 5min, makes Formazan crystallization dissolve.Finally, utilize automatic microplate reader at 570nm
The optical density in each hole is detected at wavelength.
Data process: data process and use Graph Pad Prism version5.0 program, compound IC50Pass through program
In there is the nonlinear regression model (NLRM) of S-shaped dose response be fitted obtaining.
With MTT analytic process to human colon cancer cell (Colo205) cell strain, human liver cancer cell (HepG2) cell strain, human milk
Adenocarcinoma cell (MCF7) cell strain, human cervical carcinoma cell (Hela) cell strain, human lung carcinoma cell (H460) cell strain are analyzed,
Measure its IC50Value, result is as shown in table 1, and conclusion is: from data in table, the cancer therapy drug of the present invention, to human colon carcinoma,
People's hepatocarcinoma, human breast carcinoma, human cervical carcinoma, people's lung cancer activity are higher, can be as the candidate compound of cancer therapy drug.
Table 1 triphenyltin p-Hydroxybenzoate coordination compound cancer therapy drug external activity test data
Claims (5)
1. triphenyltin p-Hydroxybenzoate coordination compound, is characterized by the compound of following structural formula (1):
Wherein: Ph represents phenyl.
2. triphenyltin p-Hydroxybenzoate coordination compound as claimed in claim 1, it is characterised in that described structural formula (1)
Coordination compound be crystal structure, crystallographic data: rhombic system, space group Fdd2, a=3.7411 (2) nm, b=1.06477
(6) nm, c=1.75171 (10) nm, α=β=γ=90 °, Z=8, V=6.9778 (7) nm3, Dc=1.345Mg m-3；Point
Center stannum in son and coordination atom constitute pentacoordinate distortion trigonal biyramid configuration.
3. the preparation method of the triphenyltin p-Hydroxybenzoate coordination compound described in claim 1 or 2, it is characterised in that
Reaction vessel is sequentially added into P-hydroxybenzoic acid 1～3mmol, triphenyl tin hydroxide 0.5～1.5mmol, solvent in order
Absolute methanol 30～80mL, is being stirred at reflux lower reaction 8～12h；Cooling, filters；Under the conditions of 25～35 DEG C, control solvent and wave
Send out crystallization, obtain colourless transparent crystal, be triphenyltin p-Hydroxybenzoate coordination compound.
4. the answering in preparing cancer therapy drug of a kind of triphenyltin p-Hydroxybenzoate coordination compound described in claim 1 or 2
With.
5. the application described in claim 4, wherein said cancer is colon cancer, hepatocarcinoma, breast carcinoma, human cervical carcinoma or pulmonary carcinoma.
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| CN201610182810.2A Pending CN105837619A (en) | 2016-03-28 | 2016-03-28 | Triphenyltin parahydroxybenzoate ester complex and preparation method and application thereof |
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| Country | Link |
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| CN (1) | CN105837619A (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0177785B1 (en) * | 1984-09-18 | 1988-07-27 | Yashima Chemical Industrial Co., Ltd. | Tris(beta,beta-dimethylphenethyl)tin compounds |
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2016
- 2016-03-28 CN CN201610182810.2A patent/CN105837619A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0177785B1 (en) * | 1984-09-18 | 1988-07-27 | Yashima Chemical Industrial Co., Ltd. | Tris(beta,beta-dimethylphenethyl)tin compounds |
Non-Patent Citations (4)
| Title |
|---|
| ADAMA MOUSSA SAKHO: "新型二和三有机锡羧酸酯的合成、晶体结构及抗癌活性", 《东北师范大学博士学位论文》 * |
| 何锡凤等，: "二苄基锡二苯甲酸酯的合成及催化性能", 《化工时刊》 * |
| 徐浩东: "单一和混合配体有机锡（IV）羧酸酯及肟类有机锡化合物的研究", 《聊城大学硕士论文》 * |
| 毛武涛: "官能基取代烃基锡及其羧酸酯配合物的合成、表征和性质研究", 《曲阜师范大学硕士论文》 * |
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