CN107759491A - Schiff bases copper（II）Anticancer complex and its preparation method and application - Google Patents
Schiff bases copper（II）Anticancer complex and its preparation method and application Download PDFInfo
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- C07—ORGANIC CHEMISTRY
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- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
- C07C251/24—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to carbon atoms of six-membered aromatic rings
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Abstract
The invention discloses a kind of schiff bases copper (II) anticancer complex and its preparation method and application.A kind of schiff bases copper (II) anticancer complex of the present invention, chemical name are：2' hydroxypropiophenonepreparation ethylenediamine contractings diamine closes copper, and its structure is shown in formula I：The preparation method of schiff bases copper (II) anticancer complex of the present invention, it is characterised in that comprise the following steps：The antitumor activity of the present invention is good, has obvious inhibitory action to HeLa human cervical carcinoma cells, LoVo colon cancer cells, A549 human lung carcinoma cells or A549/CDDP human lung adenocarcinoma multidrug resistance cells.
Description
Technical field
The invention belongs to chemosynthesis technical field, more particularly, to schiff bases copper (II) anticancer complex and its preparation side
Method and application.
Background technology
Chemotherapy is one of three big means of current mankind other side's cancer, is clinically used widely.Chemotherapy
Key agents belong to cytotoxic compound, to cancer cell lack selectivity and specificity, while cancer cell is killed
The normal histocyte of great damage, causing serious toxic side effect, [Han Rui edits chemoprevention of cancer and drug therapy north
Capital China Concord Medical Science University of medical university combined publication society Beijing, 1991].The basis of chemotherapy is chemotherapeutics, and the world is each
State puts into the research that substantial amounts of manpower and materials and financial resources carry out cancer therapy drug every year.
Copper is micro- necessary to one kind in human body, is existed in vivo in the form of complex.Many parts
Such as the compound of the organic ligand of type containing schiff bases and copper also has antiproliferation.Trans-two (salicylaldoximes) close copper
(") and structure (18) shown in macrocyclic ligand and the compound of copper there is stronger resistivity [Eio to experimental animal models tumour
H O, Lunne P O.Cancer Treat.Rep., 1985,69：1021-1032.；] Sadier P J, Nasr M,
NarayananV L, Deu.Oncol.1984,17：290-301.].1,2- double (diphenylphosphine) ethane dppe) and related benzene
Have for diphosphor compound to many cancer cells inhibitory action [Johnson R K, Mirabeiii C K, Faucette L F,
Et ai.Proc. Am.Assoc.Cancer Res., 1985,26：254-262.], but when copper ion and the organic ligand coordinate
Afterwards, stronger active anticancer can be shown.This explanation copper plays an important role in anticancer mechanism.
At present, the Metal Drugs as cancer therapy drug are mainly platinum-containing anticancer drug.Because its active anticancer is strong, action spectrum
Relatively wide, mechanism of action is unique, does not produce cross resistance with non-platinum-containing anticancer drug, is the choice drug for treating many tumours,
It is used widely.But platinum-containing anticancer drug has larger toxic side effect, the cancer patient for receiving treatment generally occurs within bone
Marrow suppresses such as thrombocytopenia, nausea and vomiting, the serious toxic side effect such as kidney and neurotrosis, therefore the non-platinum class of research small toxicity
Cancer therapy drug is still one of Main way of anticarcinogen research.
The content of the invention
A kind of regarding the issue above, the present invention provides schiff bases copper (II) anticancer cooperation that antitumor activity is good
Thing and its preparation method and application.
To reach above-mentioned purpose, present invention employs following technical proposal：A kind of schiff bases copper (II) anticancer of the present invention
Complex, chemical name are：2'- hydroxypropiophenonepreparations-ethylenediamine contracting diamine closes copper, and its structure is shown in formula I：
Schiff bases copper complex title 2'- hydroxypropiophenonepreparations-ethylenediamine contracting diamine described in the object of the invention closes copper, molecule
Formula is：[C20H22CuN2O2], molecular weight FW=394.94, its chemical structural formula and crystal structure are respectively：
The preparation method of schiff bases copper (II) anticancer complex of the present invention, comprises the following steps：
(1) the methanol dissolving of ethylenediamine and 2'- hydroxypropiophenonepreparations respectively is weighed；Treat that oil bath pot temperature is maintained at 55~75
DEG C when, 2'- hydroxypropiophenonepreparations are stirred, then ethylenediamine is added dropwise in 2'- hydroxypropiophenonepreparations, reaction backflow 5~
7h, when observing that a large amount of yellow mercury oxides occurs in reaction, cooling, decompression filters, and is precipitated, and is dried in 70~80 DEG C in drying box
It is dry, obtain the product of yellow mercury oxide；(3.374g, yield：70.38%)；
(2) yellow mercury oxide obtained above adds DMF dissolvings；Weigh Cu (NO3)2·6H2O uses H in beaker2O dissolves；
By copper nitrate solution be added drop-wise to it is above-mentioned obtain in the lysate of yellow mercury oxide, add methanol；
(3) after agitator reacts 2~3h, precipitation is produced, precipitation is filtered, filtrate is stood, after one week, it was observed that
It is adapted to the block red crystals generation of X-ray single crystal diffraction, schiff bases copper (II) is made.Yield is 60%.
Described complex is red bulk crystals, the theoretical value of feature structure parameter (%)：C, 60.77；H,
5.57；N, 7.09, experiment value is：C, 60.49；H, 5.68；N, 7.28
The chemical characteristic parameter of dilute Buddhist alkali copper (II) compound obtained above is：
Elementary analysis Anal.Calcd.for C20H22CuN2O2:C, C, 60.77；H, 5.57；N, 7.09, experiment value is：
C, 60.49；H, 5.68；N, 7.28；Infrared spectrum IR (KBr disk):ν (cm-1)=1614,1511 (ν c=N), 750, (ν c-
cl)；Its molecular formula C20H22CuN2O2, its molecular weight FW=394.94.
Further, in step (1), the mol ratio of described ethylenediamine and 2'- hydroxypropiophenonepreparations is 1:2；The second
The molal volume of diamines and methanol ratio is 1~1.5mol:2L.
Further, in step (2), described yellow mercury oxide and DMF molal volume ratio are 1.5~3mol：1L, institute
The yellow mercury oxide and six nitric hydrate copper Cu (NO stated3)2·6H2O mol ratio is 1:1.
Further, in step (2), six described nitric hydrate copper Cu (NO3)2·6H2O and water H2O mole
Volume ratio is 1.5~3mol：1L.
Further, in step (2), described water H2The volume ratio of O and methanol is 1.5~3:1.
Application of schiff bases copper (II) anticancer complex of the present invention in treating cancer.
Further, the cancer cell of the cancer is HeLa human cervical carcinoma cells, LoVo colon cancer cells, A549 human lung cancers
Cell or A549/CDDP human lung adenocarcinoma multidrug resistance cells.
Beneficial effect：The antitumor activity of the present invention is good, to HeLa human cervical carcinoma cells, LoVo colon cancer cells, A549
Human lung carcinoma cell or A549/CDDP human lung adenocarcinoma multidrug resistance cells have obvious inhibitory action.
Compared with prior art, the invention has the advantages that：
(1) complex C of the present invention20H22CuN2O2IC50 values, be 5.13 μM for HeLa human cervical carcinoma cells, hence it is evident that low
In 9.74 μM of cis-platinum, active anticancer is 1.9 times of cis-platinum；It it is 6.65 μM for LoVo colon cancer cells, hence it is evident that less than cis-platinum
14.64 μM, active anticancer is 2.2 times of cis-platinum.
(2) it is 5.66 μM for A549 human lung carcinoma cells, hence it is evident that less than 11.29 μM of cis-platinum, active anticancer is cis-platinum
2.0 again；It is 7.91 μM for A549/CDDP human lung adenocarcinoma multiple medicine-resistant cell lines, hence it is evident that less than 44.79 μM of cis-platinum, anticancer
Activity is 5.7 times of cis-platinum, and show has good antitumor activity to this four quasi-cancer cell.
Brief description of the drawings
Fig. 1 is the infrared spectrum of schiff bases copper (II) anticancer complex of the present invention.
Embodiment
Following examples only exist in illustrative purpose, without being intended to limit the scope of the present invention.
Embodiment 1
A kind of schiff bases copper (II) anticancer complex of the present invention, chemical name are：2'- hydroxypropiophenonepreparations-ethylenediamine contracting
Diamine closes copper, and its structure is shown in formula I：
Schiff bases copper complex title 2'- hydroxypropiophenonepreparations-ethylenediamine contracting diamine described in the object of the invention closes copper, molecule
Formula is：[C20H22CuN2O2], molecular weight FW=394.94, its chemical structural formula and crystal structure are respectively：
As shown in figure 1, elementary analysis Anal.Calcd.for C20H22CuN2O2:C, C, 60.77；H, 5.57；N, 7.09,
Experiment value is：C, 60.49；H, 5.68；N, 7.28；Infrared spectrum IR (KBr disk):ν (cm-1)=1614,1511 (ν c=
N),750,(νc-cl)；Its molecular formula C20H22CuN2O2, its molecular weight FW=394.94.
The preparation method of described schiff bases copper (II) anticancer complex of the present invention, comprises the following steps：
(1) the methanol dissolving of ethylenediamine and 2'- hydroxypropiophenonepreparations respectively is weighed；Treat that oil bath pot temperature is maintained at 70 DEG C
When, 2'- hydroxypropiophenonepreparations are stirred, then ethylenediamine is added dropwise in 2'- hydroxypropiophenonepreparations, reaction backflow 7h, when
It was observed that when a large amount of yellow mercury oxides occurs in reaction, cooling, decompression filters, and is precipitated, and is dried in 70 DEG C in drying box, obtains Huang
Product (3.374g, the yield of color precipitation：70.38%)；The mol ratio of described ethylenediamine and 2'- hydroxypropiophenonepreparations is 1:2；Institute
The molal volume ratio for stating ethylenediamine and methanol is 1mol:2L.
(2) yellow mercury oxide obtained above adds DMF dissolvings；Weigh Cu (NO3)2·6H2O uses H in beaker2O is molten
Solution；By copper nitrate solution be added drop-wise to it is above-mentioned obtain in the lysate of yellow mercury oxide, add methanol；Described yellow mercury oxide with
NMF DMF molal volume ratio is 1.5mol：1L, described yellow mercury oxide and six nitric hydrate copper Cu (NO3)2·
6H2O mol ratio is 1:1.Six described nitric hydrate copper Cu (NO3)2·6H2O and water H2O molal volume ratio is 1.5mol：
1L.Described water H2The volume ratio of O and methanol is 1.5:1.
(3) after agitator reacts 2h, precipitation is produced, precipitation is filtered, filtrate is stood, after one week, it was observed that suitable
The block red crystals generation of X-ray single crystal diffraction is closed, schiff bases copper (II) is made.Yield is 60%.
Described complex is red bulk crystals, the theoretical value of feature structure parameter (%)：C, 60.77；H,
5.57；N, 7.09, experiment value is：C, 60.49；H, 5.68；N, 7.28
The chemical characteristic parameter of dilute Buddhist alkali copper (II) compound obtained above is：
Elementary analysis Anal.Calcd.for C20H22CuN2O2:C, C, 60.77；H, 5.57；N, 7.09, experiment value is：
C, 60.49；H, 5.68；N, 7.28；Infrared spectrum IR (KBr disk):ν (cm-1)=1614,1511 (ν c=N), 750, (ν c-
cl)；Its molecular formula C20H22CuN2O2, its molecular weight FW=394.94.
Application of schiff bases copper (II) anticancer complex of the present invention in treating cancer.
The cancer cell of the cancer is HeLa human cervical carcinoma cells.
Embodiment 2
The difference of embodiment 2 and embodiment 1 is：The system of described schiff bases copper (II) anticancer complex of the present invention
Preparation Method, comprise the following steps：
In step (1), the methanol dissolving of ethylenediamine and 2'- hydroxypropiophenonepreparations respectively is weighed；Treat that oil bath pot temperature is protected
Hold at 55 DEG C, 2'- hydroxypropiophenonepreparations are stirred, then ethylenediamine is added dropwise in 2'- hydroxypropiophenonepreparations, reacted back
5h is flowed, when observing that a large amount of yellow mercury oxides occurs in reaction, cooling, decompression filters, and is precipitated, and is dried in 75 DEG C in drying box
It is dry, obtain the product of yellow mercury oxide；The mol ratio of described ethylenediamine and 2'- hydroxypropiophenonepreparations is 1:2；The ethylenediamine and first
The molal volume ratio of alcohol is 1.5mol:2L.
In step (2), yellow mercury oxide obtained above adds DMF dissolvings；Weigh Cu (NO3)2·6H2O in beaker,
Use H2O dissolves；By copper nitrate solution be added drop-wise to it is above-mentioned obtain in the lysate of yellow mercury oxide, add methanol；Described Huang
It is 2.5mol that color, which is precipitated with DMF molal volume ratio,：1L, described yellow mercury oxide and six nitric hydrate copper Cu (NO3)2·6H2O
Mol ratio be 1:1.Six described nitric hydrate copper Cu (NO3)2·6H2O and water H2O molal volume ratio is 2mol：1L.Institute
The water H stated2The volume ratio of O and methanol is 3:1.
In step (3), after agitator reacts 3h, precipitation is produced, precipitation is filtered, filtrate is stood, after one week,
It was observed that being adapted to the block red crystals generation of X-ray single crystal diffraction, schiff bases copper (II) is made.
Application of schiff bases copper (II) anticancer complex of the present invention in treating cancer.The cancer cell of the cancer
For LoVo colon cancer cells.
Embodiment 3
The difference of embodiment 3 and embodiment 1 is：The system of described schiff bases copper (II) anticancer complex of the present invention
Preparation Method, comprise the following steps：
In step (1), the methanol dissolving of ethylenediamine and 2'- hydroxypropiophenonepreparations respectively is weighed；Treat that oil bath pot temperature is protected
Hold at 75 DEG C, 2'- hydroxypropiophenonepreparations are stirred, then ethylenediamine is added dropwise in 2'- hydroxypropiophenonepreparations, reacted back
6h is flowed, when observing that a large amount of yellow mercury oxides occurs in reaction, cooling, decompression filters, and is precipitated, and is dried in 80 DEG C in drying box
It is dry, obtain the product of yellow mercury oxide；The mol ratio of described ethylenediamine and 2'- hydroxypropiophenonepreparations is 1:2；The ethylenediamine and first
The molal volume ratio of alcohol is 1.3mol:2L.
In step (2), yellow mercury oxide obtained above adds DMF dissolvings；Weigh Cu (NO3)2·6H2O in beaker,
Use H2O dissolves；By copper nitrate solution be added drop-wise to it is above-mentioned obtain in the lysate of yellow mercury oxide, add methanol；Described Huang
It is 3mol that color, which is precipitated with DMF molal volume ratio,：1L.Six described nitric hydrate copper Cu (NO3)2·6H2O and water H2O mole
Volume ratio is 3mol：1L.Described water H2The volume ratio of O and methanol is 2.5:1.
In step (3), agitator react 2~3h after, produce precipitation, filter precipitation, filtrate stood, one week it
Afterwards, it was observed that being adapted to the block red crystals generation of X-ray single crystal diffraction, schiff bases copper (II) is made.
Application of schiff bases copper (II) anticancer complex of the present invention in treating cancer.The cancer cell of the cancer
For A549 human lung carcinoma cells.
Embodiment 4
The preparation method of described schiff bases copper (II) anticancer complex of the present invention, comprises the following steps：
In step (1), 15mmol ethylenediamines (0.9000g) and 30mmol 2'- hydroxypropiophenonepreparations (4.5051g) are weighed
Dissolved respectively with 30mL methanol；When oil bath pot temperature is maintained at 70 DEG C, 2'- hydroxypropiophenonepreparations are stirred, then
Ethylenediamine is added dropwise in 2'- hydroxypropiophenonepreparations, reaction backflow 7h.When observing that a large amount of yellow mercury oxides occurs in reaction, cooling,
Decompression filters, and is precipitated, and is dried in 70 DEG C in drying box, obtains product (3.374g, yield：70.38%).
In step (2), 0.15mmol yellow mercury oxides (0.024g) obtained above add 10mL DMF dissolvings；Weigh
0.15mmol Cu(NO3)2·6H2O (0.030g) is in beaker, with 10 ml H2O dissolves；By being added drop-wise to for copper nitrate solution
State to obtain in the lysate of yellow mercury oxide, add 10mL methanol.
In step (3), after agitator reacts 2h, precipitation is produced, precipitation is filtered, filtrate is stood, after one week,
It was observed that it is adapted to the block red crystals generation of X-ray single crystal diffraction, yield 60%.
Application of schiff bases copper (II) anticancer complex of the present invention in treating cancer.The cancer cell of the cancer
For A549/CDDP human lung adenocarcinoma multidrug resistance cells.
Experiment 1
The anti tumor activity in vitro experiment of complex of the present invention and result
Using the cell such as HeLa human cervical carcinoma cells, LoVo colon cancer cells, A549, A549/CDDP in present invention experiment
The synthesized complex external activity of strain evaluation, while positive control is used as using cis-platinum.
Experimental principle is to detect cell viability, influence of the observation sample to tumor cell proliferation, to evaluate sample with mtt assay
Antitumous effect.
Experiment includes：
1st, cell is inoculated with
When test cell to be studied passage number on culture dish be more than or equal to 3 times when, screened from test cell
Go out the logarithmic phase cell that growth behavior meets requirement of experiment, for the cell inoculation in experiment.Then experimental article is put into appropriate
Kind position.The process of cell inoculation is as follows：
1. cotton is soaked with absolute ethyl alcohol, with cotton blood counting chamber is cleaned clean and dried up with hair-dryer, just put
On the table, sheet glass is covered；
2. the taking-up of ready culture dish gently, old culture medium is lightly drawn along culture medium with filter paper and done
Only；
3. being carefully added into 2ml PBS solutions along the inwall of culture medium, cell is then lightly cleaned, finally with filter
Paper draws PBS solution clean.
4. 1ml dropper takes 0.25% quantitative pancreatin to add in culture medium again, culture dish is lightly shaken in hand
Shake 10 times, with same method exhaustion pancreatin；
5. in incubator, wellhandled culture dish is disappeared, and with 1-3min, (disappearing required for different cells to be measured is matched somebody with somebody
Time is different),
Match somebody with somebody 6. observing cell and becoming, in we can utilize microscope see that the following change of cell appearance in culture dish is matched somebody with somebody
When one or more, in the complete new culture medium of the preparation added with 10%FBS, treat disconnected disappear of test cell and match somebody with somebody processing.Change is matched somebody with somebody
Comprising：First, it is increasingly round；2nd, cell peripheral to be measured is more and more brighter；3rd, culture medium slides in culture dish.
7. the cell in culture medium is transferred in clean centrifuge tube with pipettor, then cell suspension is prepared with it；
8. from 7. 10 μ l cell liquid of middle taking-up, then carefully cell liquid is added along the cover glass on blood counting chamber.
Under 10 × eyepiece, stand upside down observation blood counting chamber, after sight debugging is clear, does not have dyeing in statistical number plate in four block plaids
Cell quantity (dead cell discoloration)；
9. finally calculate cell density.First, (four generous by the cell number/ml=included in the cell suspension of preparation
Lattice cell number/4) × 104 (it is the cell number for counting 4 block plaids to be divided by formula with 4；2nd, tally each block plaid
Volume is：1.0mm (length) × 1.0mm (width) × 0.1mm (height)=0.1mm3, and 1ml=1000mm3)；
10. the cell suspension by being diluted to suitable concn is instilled in 96 orifice plates, each hole instills 180 μ l.96 orifice plates
It is placed in incubator, and is at CO2Under atmosphere, cultivated in 37 DEG C.
2nd, agent-feeding treatment
Before dosing, prepare to be dissolved synthetic M series complex with DMSO, be diluted to the 10mM of needs,
The complex diluted is divided into equal portions to add in doff pipes.Preserved in refrigerator, -20 DEG C of low temperature environment is (after dosing, during preservation
Between as far as possible within 3 months, in order to prevent multigelation, experiment drug effect to be measured is weakened or is lost.).After 8-12h, it was observed that
Test cell to be measured and near-wall air curtain occurs, then just negative control group is designed on experiment basis and (is not added with appointing according to advance experiment
What medicine), positive control (cis-platinum of various concentrations, concentration 0.1,1,10,50,100 μM), (M series complex is or not experimental group
Same concentration, concentration 0.1,1,10,50,100 μM).Feeding operations are completed, are rule simultaneously with experiment marker pen on 96 orifice plates immediately
Medicine code name in experiment is marked out, prevents from obscuring experimental data after the test.96 orifice plates are placed on 72h in incubator, and make it
In CO2Under atmosphere, cultivated in 37 DEG C.
3rd, MTT is detected
After standard operation, 72h is cultivated, takes out orifice plate, is then observed in earnest under the microscope to be measured after dosing thing
Cell.Such as they upgrowth situation, cell density size, their figure.Then add again and add 20 μ l 5mg/ml thereto
MTT (last diluted concentration is 0.5mg/ml), in incubator, under the same conditions, cultivate 4h.Suction out hole working specification
Outmoded culture medium in plate, and 150 μ l DMSO are gently added to it, shake, reality of the orifice plate on 37 DEG C of constant temperature oscillators
Test the time for 10min so that the first a ceremonial jade-ladle, used in libation obtained after reaction can fully dissolve.Then at 490nm, standard enzyme mark is utilized
Instrument determines light absorption value.Obtained data are handled on the basis of OD values, the IC50 values in being tested.Complex pair
The IC of growth of cancer cells50Value is as shown in table 1：
Table 1
It was found from the data of table 1, complex C20H22CuN2O2 of the present invention IC50 values, it is for HeLa human cervical carcinoma cells
5.13 ± 0.22 μM, hence it is evident that less than 9.74 ± 0.31 μM of cis-platinum, active anticancer is 1.9 times of cis-platinum；For LoVo colon cancers
Cell is 6.65 ± 1.41 μM, hence it is evident that less than 14.64 ± 7.39 μM of cis-platinum, active anticancer is 2.2 times of cis-platinum；For
A549 human lung carcinoma cells are 5.66 ± 0.57 μM, hence it is evident that less than 11.29 ± 0.42 μM of cis-platinum, active anticancer is the 2.0 of cis-platinum
Times；7.91 ± 1.15 μM for A549/CDDP human lung adenocarcinoma multiple medicine-resistant cell lines, hence it is evident that less than cis-platinum 44.79 ±
2.75 μM, active anticancer is 5.7 times of cis-platinum, and show has good antitumor activity to this four quasi-cancer cell.
General principle, principal character and the advantages of the present invention of the present invention has been shown and described above.The technology of the industry
Personnel are it should be appreciated that the present invention is not limited to the above embodiments, and the simply explanation described in above-described embodiment and specification is originally
The principle of invention, without departing from the spirit and scope of the present invention, various changes and modifications of the present invention are possible, the present invention
Claimed scope is by appended claims, specification and its equivalent thereof.
Claims (8)
1. a kind of schiff bases copper (II) anticancer complex, chemical name are：2'- hydroxypropiophenonepreparations-ethylenediamine contracting diamine closes copper, its
Structure is shown in formula I：
2. the preparation method of schiff bases copper (II) anticancer complex described in claim 1, it is characterised in that comprise the following steps：
(1) the methanol dissolving of ethylenediamine and 2'- hydroxypropiophenonepreparations respectively is weighed；Treat that oil bath pot temperature is maintained at 55~75 DEG C
When, 2'- hydroxypropiophenonepreparations are stirred, then ethylenediamine is added dropwise in 2'- hydroxypropiophenonepreparations, reaction 5~7h of backflow,
When observing that a large amount of yellow mercury oxides occurs in reaction, cooling, decompression filters, and is precipitated, and is dried in 70~80 DEG C in drying box,
Obtain the product of yellow mercury oxide；
(2) yellow mercury oxide obtained above adds DMF dissolvings；Weigh Cu (NO3)2·6H2O uses H in beaker2O dissolves；By nitre
Sour copper solution be added drop-wise to it is above-mentioned obtain in the lysate of yellow mercury oxide, add methanol；
(3) after agitator reacts 2~3h, precipitation is produced, precipitation is filtered, filtrate is stood, after one week, it was observed that being adapted to
The block red crystals generation of X-ray single crystal diffraction, is made schiff bases copper (II).
3. the preparation method of schiff bases copper (II) anticancer complex according to claim 2, it is characterised in that：In step
(1) in, the mol ratio of described ethylenediamine and 2'- hydroxypropiophenonepreparations is 1:2；The molal volume ratio of the ethylenediamine and methanol is
1~1.5mol:2L.
4. the preparation method of schiff bases copper (II) anticancer complex according to claim 3, it is characterised in that：In step
(2) in, described yellow mercury oxide and DMF molal volume ratio are 1.5~3mol：1L, described yellow mercury oxide and six hydration nitre
Sour copper Cu (NO3)2·6H2O mol ratio is 1:1.
5. the preparation method of schiff bases copper (II) anticancer complex according to claim 4, it is characterised in that：In step
(2) in, six described nitric hydrate copper Cu (NO3)2·6H2O and water H2O molal volume ratio is 1.5~3mol：1L.
6. the preparation method of schiff bases copper (II) anticancer complex according to claim 5, it is characterised in that：In step
(2) in, described water H2The volume ratio of O and methanol is 1.5~3:1.
7. application of schiff bases copper (II) anticancer complex in treating cancer described in any one of claim 1 to 6.
8. application according to claim 7, it is characterised in that：The cancer cell of the cancer be HeLa human cervical carcinoma cells,
LoVo colon cancer cells, A549 human lung carcinoma cells or A549/CDDP human lung adenocarcinoma multidrug resistance cells.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN109053816A (en) * | 2018-09-27 | 2018-12-21 | 陕西理工大学 | A kind of preparation method and its antitumor application of the Schiff base complex of ruthenium |
| CN109125346A (en) * | 2018-08-14 | 2019-01-04 | 兰州大学 | A kind of reproducible copper carrier antitumor and anticancer agent and its application |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN1585976A (en) * | 2001-11-13 | 2005-02-23 | 西巴特殊化学品控股有限公司 | Compositions comprising at least one oxonol dye and at least one metal complex |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN1585976A (en) * | 2001-11-13 | 2005-02-23 | 西巴特殊化学品控股有限公司 | Compositions comprising at least one oxonol dye and at least one metal complex |
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| SHANKARWAR, SUNIL G.ET AL.: "Synthesis, spectral, thermal and antimicrobial studies of transition metal complexes of 14-membered tetraaza[N4] macrocyclic ligand", 《SPECTROCHIMICA ACTA PART A: MOLECULAR AND BIOMOLECULAR SPECTROSCOPY》 * |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109125346A (en) * | 2018-08-14 | 2019-01-04 | 兰州大学 | A kind of reproducible copper carrier antitumor and anticancer agent and its application |
| CN109053816A (en) * | 2018-09-27 | 2018-12-21 | 陕西理工大学 | A kind of preparation method and its antitumor application of the Schiff base complex of ruthenium |
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| CN107759491B (en) | 2019-02-22 |
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