CN110128452A - A kind of gold complex and its synthetic method and application - Google Patents
A kind of gold complex and its synthetic method and application Download PDFInfo
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- CN110128452A CN110128452A CN201910372292.4A CN201910372292A CN110128452A CN 110128452 A CN110128452 A CN 110128452A CN 201910372292 A CN201910372292 A CN 201910372292A CN 110128452 A CN110128452 A CN 110128452A
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- synthetic method
- chloroaurate
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- 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
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic System
- C07F1/12—Gold compounds
Abstract
The invention discloses a kind of gold complex and its synthetic method and applications.The synthetic method of the gold complex includes: that four hydration gold chlorides or chloroaurate and phenyl ethylamine class ligand is taken to be placed in organic solvent, is coordinated under the conditions of being protected from light, and reactant is cooling, stands crystallization, collect crystal to get；Wherein, the chloroaurate is sodium chloraurate or potassium chloroaurate, and the phenyl ethylamine class ligand is homopiperony lamine.The experiment of applicant shows that complex of the present invention has good proliferation inhibition activity and anti-drug resistance to certain tumor cell lines, and lower to the toxicity of human normal cell line HL-7702, while physiological stability also with higher.Shown in complex structure of the present invention such as following formula (I):
Description
The application is the divisional application of " organic golden (III) complex of metal and its synthetic method and application ", original application
The applying date are as follows: on 2 5th, 2018, application No. is: 201810111445.5, denomination of invention are as follows: organic golden (III) cooperation of metal
Object and its synthetic method and application.
Technical field
The present invention relates to pharmaceutical technology fields, and in particular to organic golden (III) complex of a metalloid and its synthetic method
And application.
Background technique
Cis-platinum and the like carboplatin and oxaliplatin have been successfully used to treat a variety of solid tumors, but serious resistance to
Pharmacological property and side effect limit the clinical efficacy of these platinum medicines, therefore the gold with stronger anticancer activity and more low side effect
Metal complex becomes the research interest of numerous scholars.The non-platinum metals complex in part shows the drug design of high-efficiency low-toxicity
Attribute, part of gold complex also show that the anticancer mechanism for differing markedly from platinum medicine, however, general gold complex
Low physiological stability hinders their therapeutic effects in vivo.
1,2,3,4- tetrahydroisoquinoline (THIQ) is a kind of special alkaloid compound, is widely present in natural products
In, it has certain bioactivity.Currently, the metal of (different) quinoline is ground extensively with compound and its various bioactivity
Study carefully, but not yet by the synthesis for replacing one of carbon atom in the N- heterocycle structure of metallic atom insertion THIQ and its activity research
Seeing has relevant report.
Summary of the invention
The technical problem to be solved in the present invention is to provide organic golden (III) complex of the metal of a kind of structure novel and its conjunctions
At methods and applications.
Organic golden (III) complex of metal of the present invention be with compound shown in following formula (I)s or its pharmaceutically
Acceptable salt:
Wherein, R1Indicate OMe or OCH2O, R2Indicate OMe or OCH2O。
The synthetic method of organic golden (III) complex of metal of the present invention are as follows: take four hydration gold chlorides or gold chloride
Salt and phenyl ethylamine class ligand are placed in organic solvent, are coordinated under the conditions of being protected from light, and reactant is cooling, stand crystallization, are collected
Crystal is to get target product；Wherein, the chloroaurate is sodium chloraurate or potassium chloroaurate, the phenyl ethylamine class ligand
3,4- dimethoxy-phenylethylamine or homopiperony lamine.
In above-mentioned synthetic method, the ratio between the amount of substance of the four hydration gold chloride or chloroaurate and phenyl ethylamine class ligand
For stoichiometric ratio, in actual operation, the molar ratio of four hydration gold chlorides or chloroaurate and phenyl ethylamine class ligand is usual
It can be 1~5:1.
In above-mentioned synthetic method, the organic solvent be can be selected from methylene chloride, acetone, ethyl alcohol, methanol and chloroform
In any one or two or more combinations.Proportion when organic solvent is the combination more than above two, between them
It can be any proportion.The organic solvent is preferably first used using precedingMolecular sieve is dehydrated, to be more advantageous to anti-
The progress answered.The dosage of organic solvent can determine as needed, can usually dissolve the raw material for participating in reaction, specifically
, it is calculated on the basis of the four hydration gold chlorides or chloroaurate and 0.1mmol phenyl ethylamine class ligand of 0.1mmol, whole raw materials
Total dosage of organic solvent used generally uses 10~150mL, preferably 15~50mL.When the additional amount of organic solvent is larger
When, after stopping reaction, the most of organic solvent of the methods of vacuum distillation removing can be first passed through and (usually remove and occupy solvent
The 80~95% of input amount), then target product will can equally be precipitated after reaction solution cooling, standing.
In above-mentioned synthetic method, the reaction can carry out under conditions of being heated or not heated.When reaction is in fire-bar
When carrying out under part, the temperature of reaction is lower than the boiling temperature of organic solvent, and preferably reaction carries out under the conditions of 50~80 DEG C.Instead
Whether thin-layer chromatography (TLC) tracing detection should can be used completely.After completion of the reaction, it is cooled down again after preferably first filtering reactant
Stand crystallization.The time of standing is usually 1~5 day.
The yield of organic golden (III) complex of metal is prepared 40% or more, specially 40~90% by the above method.Institute
Organic golden (III) complex of metal obtained can also achieve the purpose that be further purified by the method for recrystallization, tie again
Solvent used is identical as aforementioned organic solvents when brilliant.
The invention also includes organic golden (III) complex of above-mentioned metal or its pharmaceutically acceptable salt prepare it is antitumor
Application in drug.
The present invention further comprises a kind of pharmaceutical composition, contains the above-mentioned of the upper effective dose for the treatment of in the pharmaceutical composition
Organic golden (III) complex of metal or its pharmaceutically acceptable salt.
Compared with prior art, the present invention provides organic golden (III) complex of the metal of two structure novels and its conjunctions
At methods and applications, our experiments show that, they have good proliferation inhibition activity to certain tumor cell lines and resist
Drug resistance, and it is lower to the toxicity of human normal cell line HL-7702, while physiological stability also with higher.It is of the present invention
The synthetic method of complex is simple, reaction condition is mild, and reaction raw materials are cheap and easy to get, low in cost.
Detailed description of the invention
Fig. 1 is the mono-crystalline structures figure of final product made from the embodiment of the present invention 1；
Fig. 2 is the mono-crystalline structures figure of final product made from the embodiment of the present invention 6；
Fig. 3 is to act on for 24 hours under the conditions of physiological buffered solution by Cyc-Au-1 made from 1 the method for the embodiment of the present invention
And the HPLC testing result figure of 48h；
Fig. 4 is to act on for 24 hours under the conditions of physiological buffered solution by Cyc-Au-2 made from 6 the method for the embodiment of the present invention
And the HPLC testing result figure of 48h.
Specific embodiment
The present invention is described in further detail combined with specific embodiments below, content to better understand the invention, but
The present invention is not limited to following embodiments.
Embodiment 1: the synthesis of target product Cyc-Au-1
Take KAuCl4(0.2mmol) and 3,4- dimethoxy-phenylethylamine (0.2mmol) are placed in container, and 30mL is then added
The in the mixed solvent (volume ratio of methylene chloride and methanol is 1:1) being made of methylene chloride and methanol, gained mixture is protected from light
Under the conditions of return stirring reaction for 24 hours, gained reactant filtering collects filtrate, stands, there is a yellow crystals precipitation, collects crystal, very
Sky is dry, obtains yellow solid product, yield 55%.
The present embodiment products therefrom is characterized:
1) nucleus magnetic hydrogen spectrum is analyzed, and gained spectral data is as follows:
Nucleus magnetic hydrogen spectrum:1H NMR(400MHz,DMSO-d6) δ 6.84 (d, J=8.1Hz, 1H), 6.70 (dd, J=8.1,
1.6Hz, 1H), 3.74 (s, 3H), 3.72 (s, 3H), 2.81-2.67 (t, J=5.4Hz 2H), 2.57 (t, J=7.2Hz, 2H).
2) Electrospray Ionization Mass Spectrometry: m/z 490.4 [M-Cl+DMSO]+。
3) X-ray single crystal diffraction is analyzed:
Monocrystalline X- is carried out to blackish green flat crystal obtained by the present embodiment as agilent company SuperNova single crystal diffractometer
Ray analysis, crystallographic data is as described in Table 1, and the crystal structure figure of products therefrom is as shown in Figure 1.
The crystallographic data of table 1:Cyc-Au-1 and Cyc-Au-2
Accordingly, it can be determined that yellow solid product obtained by the present embodiment is target product Cyc-Au-1, molecular formula is
C10H14NO2Cl2Au, structure are shown below:
Embodiment 2: the synthesis of target product Cyc-Au-1
Embodiment 1 is repeated, unlike: the mixed solvent being made of methylene chloride and methanol is replaced with chloroform.Yield
58%.
Nucleus magnetic hydrogen spectrum, electrospray ionization mass spectrum and the analysis of X-ray single crystal diffraction are carried out to the present embodiment products therefrom, determine this reality
Applying a products therefrom is target product Cyc-Au-1.
Embodiment 3: the synthesis of target product Cyc-Au-1
Embodiment 1 is repeated, unlike: reaction carries out under the conditions of 25 DEG C, and the time of reaction is 48h.Yield 46%.
Nucleus magnetic hydrogen spectrum, electrospray ionization mass spectrum and the analysis of X-ray single crystal diffraction are carried out to the present embodiment products therefrom, determine this reality
Applying a products therefrom is target product Cyc-Au-1.
Embodiment 4: the synthesis of target product Cyc-Au-1
Embodiment 1 is repeated, unlike: use HAuCl4·4H2O replaces KAuCl4.Yield 59%.
Nucleus magnetic hydrogen spectrum, electrospray ionization mass spectrum and the analysis of X-ray single crystal diffraction are carried out to the present embodiment products therefrom, determine this reality
Applying a products therefrom is target product Cyc-Au-1.
Embodiment 5: the synthesis of target product Cyc-Au-1
Embodiment 1 is repeated, unlike: use NaAuCl4Instead of KAuCl4.Yield 58%.
Nucleus magnetic hydrogen spectrum, electrospray ionization mass spectrum and the analysis of X-ray single crystal diffraction are carried out to the present embodiment products therefrom, determine this reality
Applying a products therefrom is target product Cyc-Au-1.
Embodiment 6: the synthesis of target product Cyc-Au-2
Take NaAuCl4(0.2mmol) and 3, the sub- methoxyphenethylamine (0.2mmol) of 4- bis- are placed in container, are then added
The in the mixed solvent (volume ratio of methylene chloride and methanol is 1:1) that 30mL is made of methylene chloride and methanol, gained mixture
For 24 hours, gained reactant filtering is collected filtrate, is stood, there is yellow crystals precipitation for return stirring reaction under the conditions of being protected from light, and collects brilliant
Body, vacuum drying, obtains yellow solid product, yield 43%.
The present embodiment products therefrom is characterized:
1) nucleus magnetic hydrogen spectrum is analyzed, and gained spectral data is as follows:
Nucleus magnetic hydrogen spectrum:1H NMR(400MHz,DMSO-d6) δ 6.81 (dd, J=7.7,3.6Hz, 1H), 6.65 (dd, J=
7.9,1.7Hz, 1H), 5.96 (s, 2H), 2.73 (t, J=7.2Hz, 1H), 2.56 (t, J=7.2Hz, 1H).
2) Electrospray Ionization Mass Spectrometry: m/z 474.9 [M-Cl+DMSO]+。
3) X-ray single crystal diffraction is analyzed:
Monocrystalline X- is carried out to blackish green flat crystal obtained by the present embodiment as agilent company SuperNova single crystal diffractometer
Ray analysis, crystallographic data is as shown in Table 1 above, and the crystal structure figure of products therefrom is as shown in Figure 2.
Accordingly, it can be determined that yellow solid product obtained by the present embodiment is target product Cyc-Au-2, molecular formula is
C9H10NO2Cl2Au, structure are shown below:
Embodiment 7: the synthesis of target product Cyc-Au-2
Embodiment 6 is repeated, unlike: it replaces being made of methylene chloride and methanol with the mixture of ethyl alcohol and chloroform mixed
Bonding solvent, wherein the volume ratio of ethyl alcohol and chloroform is 3:1.Yield 53%.
Nucleus magnetic hydrogen spectrum, electrospray ionization mass spectrum and the analysis of X-ray single crystal diffraction are carried out to the present embodiment products therefrom, determine this reality
Applying a products therefrom is target product Cyc-Au-2.
Embodiment 8: the synthesis of target product Cyc-Au-2
Embodiment 6 is repeated, unlike: the mixed solvent being made of methylene chloride and methanol is replaced with acetone, reaction exists
It is carried out under the conditions of 40 DEG C, the time of reaction is for 24 hours.Yield 43%.
Nucleus magnetic hydrogen spectrum, electrospray ionization mass spectrum and the analysis of X-ray single crystal diffraction are carried out to the present embodiment products therefrom, determine this reality
Applying a products therefrom is target product Cyc-Au-2.
Embodiment 9: the synthesis of target product Cyc-Au-2
Embodiment 6 is repeated, unlike: use HAuCl4·4H2O replaces KAuCl4.Yield 45%.
Nucleus magnetic hydrogen spectrum, electrospray ionization mass spectrum and the analysis of X-ray single crystal diffraction are carried out to the present embodiment products therefrom, determine this reality
Applying a products therefrom is target product Cyc-Au-2.
Embodiment 10: the synthesis of target product Cyc-Au-2
Embodiment 6 is repeated, unlike: use KAuCl4Instead of NaAuCl4.Yield 48%.
Nucleus magnetic hydrogen spectrum, electrospray ionization mass spectrum and the analysis of X-ray single crystal diffraction are carried out to the present embodiment products therefrom, determine this reality
Applying a products therefrom is target product Cyc-Au-2.
Experimental example 1: complex of the present invention carries out external inhibitory activity experiment to a variety of human tumour strains:
1, cell strain and cell culture
Human liver cancer cell BEL-7404, bladder cancer cell HepG-2, ovarian cancer cell SK-OV-3, lung cancer are selected in this experiment
Cell A549, the lung cancer cell of resistance to cis-platinum A549/CDDP, colon cancer cell HCT116 and Human normal hepatocyte HL-7702.
All cell strains are cultivated in the RPMI- for containing 10% fetal calf serum, 100U/mL penicillin, 100U/mL streptomysin
In 1640 or DMEM culture solution, 37 DEG C of 5%CO containing volumetric concentration are set2It is cultivated in incubator.Inverted microscope observes cell and grows feelings
Condition, the passage of 0.25% trypsin digestion, logarithmic growth phase cell is for testing.
2, the preparation of untested compound
Cyc-Au-1 and Cyc-Au-2 used presses 6 the method products therefrom of the embodiment of the present invention 1 and embodiment respectively
With 2 gained of recrystallize with dichloromethane, its DMSO liquid storage (concentration 0.002mol/L) is passed through RPMI- by purity >=95%
1640 or DMEM culture medium is successively diluted to five concentration gradients, respectively 40,20,10,5,2.5 μm of ol/L, wherein cosolvent
DMSO final concentration≤1%.Target product under different gradient concentrations is tested respectively to use the Proliferation Ability degree of various tumour cells
With the Fitting Calculation half-inhibitory concentration, i.e. IC50Value.All tests at least independence is in triplicate.
3, cell growth inhibition test (mtt assay)
(1) tumour cell of logarithmic growth phase is matched after trypsin digestion with the culture solution containing 10% fetal calf serum
Cell suspension processed is inoculated in 96 well culture plates with every 180 μ L of hole, makes cell density to be measured to 1000-10000/hole (edge
It is filled with sterile PBS in hole)；
(2) 5%CO2, 37 DEG C are incubated for for 24 hours, until cell monolayer is paved with bottom hole 60~70%, a certain concentration gradient is added in every hole
20 μ L of drug, each concentration gradient sets 5 multiple holes；
(3) 5%CO2, 37 DEG C of incubation 48h observe under inverted microscope；
(4) the MTT solution (5mg/mL) of 20 μ L is added in every hole, continues to cultivate 4h
(5) culture is terminated, culture solution in hole is carefully sucked, every hole is added 150 μ L DMSO and sufficiently dissolves first a ceremonial jade-ladle, used in libation precipitating, vibration
It swings after device mixes, with wavelength is 570nm in microplate reader, reference wavelength is the OD value that 630nm measures each hole；
(6) it is arranged zeroing hole (culture medium, MTT, DMSO) simultaneously, (the drug dissolution of cell, same concentrations is situated between control wells
Matter, culture solution, MTT, DMSO)；
(7) according to the OD value (OD value) measured, to judge living cells quantity, OD value is bigger, and cell activity is stronger.Benefit
With formula:
Calculate the inhibiting rate of compound on tumor cell growth.Test result is as follows for it shown in table 2:
Growth inhibition ratio (%) of the table 2:Cyc-Au-1 and Cyc-Au-2 to 6 kinds of tumor cell lines, 1 plant of normal cell strain
Note: human liver cancer cell BEL-7404, bladder cancer cell HepG-2, ovarian cancer cell SK-OV-3, lung carcinoma cell
A549, the lung cancer cell of resistance to cis-platinum A549/CDDP, colon cancer cell HCT116, Human normal hepatocyte HL-7702, selected change
Closing object primary dcreening operation concentration is 20 μm of ol/L.
It is further fitted by inhibiting rate data of the Bliss software to five concentration gradients, finds out product to difference
Half-inhibitory concentration (the IC of tumor line50Value, unit μm ol/L), as a result as shown in table 3 below:
IC of the table 3:Cyc-Au-1 and Cyc-Au-2 to 6 kinds of tumor cell lines, one plant of normal cell strain50It is worth (μM)
From the point of view of anti tumor activity in vitro test result, it is living that complex Cyc-Au-1 and Cyc-Au-2 all have broad spectrum anticancer
Property, while two kinds of gold complexs show lower cytotoxic activity to normal liver cell HL-7702.It can be seen that complex Cyc-
Au-1 and Cyc-Au-2 shows a degree of selectivity to cancer cell.Two kinds of gold complexs are compared, Cyc-Au-2 tool
There is higher inhibiting tumour cells activity.Compared with clinical anti-cancer drugs Cisplatin, also overall performance goes out better swell to Cyc-Au-2
Tumor growth inhibitory activity and to the lower cytotoxicity of normal liver cell HL-7702, thus Cyc-Au-2 have than cis-platinum it is more preferable
Cell toxicant selectivity.Simultaneously from the point of view of the drug resistance to cisplatin resistance strain A549/DDP, wherein Cyc-Au-1 and Cyc-Au-2
Drug-resistance factor RF to A549/DDP is respectively 1.42 and 1.15, and the drug-resistance factor of cis-platinum is 7.12, the result shows that Cyc-
Au-1 and Cyc-Au-2 shows lower drug resistance than cis-platinum.
In conclusion organic golden (III) the complex conjunction object aggregate performance of metal of the present invention has gone out centainly external and has resisted
Tumor promotion has apparent toxicity selectivity and anti-drug resistance effect to cancer cell, has good potential medical value, have
Hope the preparation for being used for various anti-tumor drugs.
Experimental example 2: the biological stability experiment of complex of the present invention
(1) 10 μ L DMSO liquid storages (2 × 10 of Cyc-Au-1 (being made by 1 the method for the embodiment of the present invention) are taken-3mol/
L it) is added in 1mLPBS solution, is incubated at 37 DEG C for 24 hours and 48h, detect its variation feelings with Waters 2950HPLC after being incubated for
Condition, result are as shown in Figure 3.
(2) 10 μ L DMSO liquid storages (2 × 10 of Cyc-Au-2 (being made by 6 the method for the embodiment of the present invention) are taken-3mol/
L it) is added in 1mLPBS solution, is incubated at 37 DEG C for 24 hours and 48h, detect its variation feelings with Waters 2950HPLC after being incubated for
Condition, result are as shown in Figure 4.
As can be seen from figs. 3 and 4 the peak without obvious other ingredients occurs after two complexs act on 24 and 48h respectively, say
Bright two complexs are stable in physiological buffered solution.
Claims (9)
1. compound shown in following formula or its pharmaceutically acceptable salt:
2. the synthetic method of compound described in claim 1, it is characterised in that: mainly comprise the steps that and take four hydration chlorine gold
Acid or chloroaurate and phenyl ethylamine class ligand are placed in organic solvent, are coordinated under the conditions of being protected from light, and reactant is cooling, are stood
Crystallization collects crystal to get target product；Wherein, the chloroaurate is sodium chloraurate or potassium chloroaurate, the benzene second
Amine ligand is homopiperony lamine.
3. synthetic method according to claim 2, it is characterised in that: the organic solvent be selected from methylene chloride, acetone,
Any one in ethyl alcohol, methanol and chloroform or two or more combinations.
4. synthetic method according to claim 2, it is characterised in that: it is described reaction under conditions of being heated or not heated into
Row.
5. synthetic method according to claim 4, it is characterised in that: when reaction is performed under heating conditions, reaction temperature
Degree is lower than the boiling temperature of organic solvent.
6. synthetic method according to claim 5, it is characterised in that: the reaction carries out under the conditions of 50~80 DEG C.
7. the synthetic method according to any one of claim 2-6, it is characterised in that: further include purification step: being specifically
Target product obtained is recrystallized to obtain target product after purification.
8. compound described in claim 1 or its pharmaceutically acceptable salt application in preparation of anti-tumor drugs.
9. a kind of pharmaceutical composition goes up compound described in the claim 1 of effective dose containing treatment or its is pharmaceutically acceptable
Salt.
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| CN114316951A (en) * | 2021-12-23 | 2022-04-12 | 南京邮电大学 | Cadmium-based two-dimensional hybrid perovskite long-afterglow material and preparation method and application thereof |
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| CN114316951B (en) * | 2021-12-23 | 2023-12-22 | 南京邮电大学 | Cadmium-based two-dimensional hybridization perovskite long afterglow material, and preparation method and application thereof |
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| CN108148080A (en) | 2018-06-12 |
| CN110128452B (en) | 2020-12-01 |
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