CN102603642B - Nickel-containing sandwich polyoxometallate anti-cancer drug and synthesis method thereof - Google Patents
Nickel-containing sandwich polyoxometallate anti-cancer drug and synthesis method thereof Download PDFInfo
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- CN102603642B CN102603642B CN201110450744.XA CN201110450744A CN102603642B CN 102603642 B CN102603642 B CN 102603642B CN 201110450744 A CN201110450744 A CN 201110450744A CN 102603642 B CN102603642 B CN 102603642B
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Abstract
The invention relates to a nickel-containing sandwich polyoxometallate anti-cancer drug and a synthesis method thereof. The Na4Bi2Ni2W20C6H84N4O105 synthesized by the invention is a polyoxometallate modified by active imidazole, and has strong proliferation suppression effect to human liver cancer cells as well as inhibition ratio to human gastric cancer cells and human colon cancer cells. The method includes the following steps: 1) under the effect of magnetic agitation, dissolving 4.7 mmol of Na2WO4 in 100ml of deionized water and heating to 100 DEG C, then adding hydrochloric acid with concentration being 6mol/L to regulate pH to 6.0 to obtain solution A; and 2) adding 0.7 mmol of NiCl2, 1 mmol of solid imidazole and 0.5 mmol of Bi(NO3)3 dissolved in 10ml of HCl with concentration being 6mol/L into the solution A at the same time, evenly mixing, heating to 100 DEG C for reaction for 1.5h, cooling to room temperature, filtering and finally statically placing for 8 days. The nickel-containing sandwich polyoxometallate anti-cancer drug is used for inhibiting human gastric cancer cells and colon cancer cells.
Description
technical field:
the present invention relates to a kind of bismuth tungstate and synthetic method thereof to the activated transiting metal nickels of tool such as people's liver cancer and people's cancer of the stomach tumour cell and imidazoles modification, be specifically related to a kind of nickeliferous sandwich polyoxometallate cancer therapy drug and synthetic method thereof.
background technology:
in recent years, the pharmaceutical chemistry research of polyoxometallate has obtained impressive progress, and its pharmacology, physiologically active are identified, in research Showed Very Brisk antiviral, anti-tumor aspect.1971, first French scientist Raynaud found that Keggin type tungsten sila polyanionic can suppress mouse fibrosarcoma virus (MLSV), in succession found [BW later
12
o
40
]
5-
deng showing in vitro antiviral activity.1985, the discovery HPA-23 such as Dormont had restraining effect to the reversed transcriptive enzyme of HIV (human immunodeficiency virus), and were applied to clinical in France and the U.S. very soon.The Keggin structure silicotungstate that the discovery organosilicon such as Hill in 1992 the replaces HIV (human immunodeficiency virus) HIV-1 that can draw up.Nineteen ninety-five, the sandwich isostructural poly-tungstate of the discovery Keggin such as Yamase, vacant Keggin, Wells-Dawson and Keggin has anti-microbial activity to staphylococcus aureus, calendar year 2001, Hill etc. have adopted the study of computer simulation containing the Wells-Dawson structure of niobium and the interaction situation of HIV-1 albumen.These researchs only comprise inhibited proliferation, morphological observation, the detection of cell cycle etc.Therefore, polyoxometallate meets future studies and the development trend of field of medicaments anticancer chemotherapeutic agent as new drug development.
summary of the invention:
the object of this invention is to provide a kind of nickeliferous sandwich polyoxometallate cancer therapy drug and synthetic method thereof, obtain a kind of to activated novel cpds of cancer tool such as people's liver cancer, people's cancer of the stomach tumour cells.To have synthetic method simple for this technology simultaneously, and productive rate is high, is the anticancer newtype drug of a kind of potential broad-spectrum, has great application value.
above-mentioned object realizes by following technical scheme:
a kind of cancer therapy drug Na
4
bi
2
ni
2
w
20
c
6
h
84
n
4
o
105
synthetic method, the method comprises the steps:
(1) under magnetic agitation, by the Na of 4～5mmol
2
wO
4
be dissolved in the deionized water of 80～120ml, and be heated to 80～120 DEG C, then dropwise add the HCl of 6mol/L to regulate pH to 5.0～7.0, obtain solution A;
(2) by the NiCl of 0.5～1mmol
2
, 0.8～1.2mmol solid imidazoles, be dissolved in the Bi (NO of 0.3～0.8mmol in 10mL 6 mol/L HCl
3
)
3
join in solution A simultaneously, mix post-heating to 80～120 DEG C reaction 1～2h, be then cooled to room temperature, after filtering, leave standstill 5～10 days.
a kind of with the synthetic cancer therapy drug Na of aforesaid method 4 bi 2 ni 2 w 20 c 6 h 84 n 4 o 105 , its molecular formula is: Na 4 bi 2 ni 2 w 20 c 6 h 84 n 4 o 105 , molecular weight: 6196.87,
its structural formula is:
it under normal temperature, is green bulk crystals.
beneficial effect:
1. the synthetic Na of the present invention
4
bi
2
ni
2
w
20
c
6
h
84
n
4
o
105
be the polyoxometallate that the activated imidazoles of a kind of tool is modified, it has very strong inhibited proliferation, people's gastric tumor cells and human colon carcinoma tumour cell is also had to good inhibiting rate human liver cancer cell.The Na that the present invention is synthetic
4
bi
2
ni
2
w
20
c
6
h
84
n
4
o
105
adopt MTT method to detect the growth-inhibiting effect of this compound to tumour cell, its half-inhibition concentration IC
50
=0.081mmol/L, 24h.The fluorescence colour such as AO/EB, FITC/PI detects gained anticancer compound Na in the present invention
4
bi
2
ni
2
w
20
c
6
h
84
n
4
o
105
tumor cell line is had to apoptosis-induced effect.Adopt agarose gel electrophoresis (DNA ladder) laboratory method of SCGE experiment (comet assay) and apoptotic cell to detect gained anticancer compound Na in the present invention
4
bi
2
ni
2
w
20
c
6
h
84
n
4
o
105
the DNA damage situation that tumor cell line experiment in vitro is existed.Adopt transmission electron microscope and scanning electron microscope morphological observation, obtained gained anticancer compound Na in the present invention
4
bi
2
ni
2
w
20
c
6
h
84
n
4
o
105
the ultrastructure of cell death inducing, adopts Flow Cytometry to detect apoptotic per-cent.The present invention is significant and researching value in the antitumor pharmacy functional study of polyoxometallate, provide scientific basis using the feasibility for the treatment of new drug as malignant tumour clinical chemistry for polyoxometallate, for antitumor chemical new drug development is established scientific experiment basis.
. gained anticancer compound Na of the present invention
4
bi
2
ni
2
w
20
c
6
h
84
n
4
o
105
, detect the impact of its various dose on people's cancer of the stomach and colorectal carcinoma inhibition rate of tumor cell; Result as shown in Figure 3, visible, along with anticancer compound Na
4
bi
2
ni
2
w
20
c
6
h
84
n
4
o
105
the increase of consumption, people's cancer of the stomach and colorectal carcinoma inhibition rate of tumor cell increase gradually, and gained anticancer compound Na in the present invention is described
4
bi
2
ni
2
w
20
c
6
h
84
n
4
o
105
people's cancer of the stomach and colorectal carcinoma tumour cell are had to good inhibiting rate.Adopt the fluorescence colour such as AO/EB, FITC/PI to detect gained anticancer compound Na in the present invention simultaneously
4
bi
2
ni
2
w
20
c
6
h
84
n
4
o
105
tumor cell line is had to apoptosis-induced effect.Adopt two kinds of experimental techniques of agarose gel electrophoresis (DNA ladder) of single cell gel electrophoresis (comet assay) and apoptotic cell to detect gained anticancer compound Na in the present invention
4
bi
2
ni
2
w
20
c
6
h
84
n
4
o
105
to the external damaging action with inducing DNA of tumor cell line.Adopt transmission electron microscope and scanning electron microscope morphological observation, gained anticancer compound Na in the present invention is described
4
bi
2
ni
2
w
20
c
6
h
84
n
4
o
105
ultrastructure that can inducing apoptosis of tumour cell, adopts low cytometric analysis to detect apoptotic per-cent.Gained anticancer compound Na in the present invention
4
bi
2
ni
2
w
20
c
6
h
84
n
4
o
105
with the comparative studies of conventional clinical chemotherapy medicine (5 FU 5 fluorouracil) at tumor inhibition effect; Result as shown in Figure 4, visible, gained anticancer compound Na in the present invention
4
bi
2
ni
2
w
20
c
6
h
84
n
4
o
105
the restraining effect to human liver tumor cell be greater than 5 FU 5 fluorouracil, illustrate that it has good antitumour activity.
. the present invention, by conventional soln method, controls pH value, ingredient proportion and the temperature of solution, obtains a kind of to activated novel cpds of cancer tool such as people's liver cancer, people's cancer of the stomach tumour cells.To have synthetic method simple for this technology simultaneously, and productive rate is high, through a large amount of experimental results show that:
(1), in the time that other condition is constant, if regulate pH value to be less than after the same temporal filtering of 5.5 reaction, placing a couple of days is still clear solution, produces without crystal; Under similarity condition, if pH, higher than 7.5, can not obtain green precipitate.
(2), in the time that other condition is constant, if Heating temperature lower than 40 DEG C, is reacted after same temporal filtering, placing a couple of days is still clear solution, produces without crystal.Under similarity condition, if Heating temperature exceedes 80 DEG C, obtain thin and in small, broken bits crystal, can not meet test request.
(3), in the time that other condition is constant, when not enough 1.5h of reaction times, after filtration, placing a couple of days is still clear solution, produces without crystal; Under similarity condition, if when the reaction times exceedes 2.5h, can obtain green spherical noncrystal.
brief description of the drawings:
fig. 1 is the people's tumor cells of hepatocellular carcinoma aspect graph before the present invention uses;
fig. 2 is the people's tumor cells of hepatocellular carcinoma aspect graph after effect 24 h of the present invention;
fig. 3 is the graphic representation of this product of various dose impact on people's cancer of the stomach and colorectal carcinoma inhibition rate of tumor cell;
fig. 4 is the present invention and the graphic representation of 5 FU 5 fluorouracil on human liver cancer cell impact.
embodiment:
following examples are just for better explanation the present invention, and the present invention is not limited to following examples.
embodiment 1:
present embodiment anticancer compound Na
4
bi
2
ni
2
w
20
c
6
h
84
n
4
o
105
synthetic method realize according to the following steps: one, under magnetic agitation, by the Na of 4～5mmol
2
wO
4
be dissolved in the deionized water of 80～120ml, and be heated to 80～120 DEG C, then dropwise add the HCl of 6mol/L to regulate pH to 5.0～7.0, obtain solution A; Two, by the NiCl of 0.5～1mmol
2
, 0.8～1.2mmol solid imidazoles and be dissolved in the Bi (NO of 0.3～0.8mmol in 6mol/L HCl
3
)
3
join in solution A simultaneously, mix post-heating to 80～120 DEG C reaction 1～2h, be then cooled to room temperature, after filtering, leave standstill 5～10 days, complete anticancer compound Na
4
bi
2
ni
2
w
20
c
6
h
84
n
4
o
105
synthetic; Wherein in step 2, the consumption of HCl is 10mL.
gained anticancer compound Na in present embodiment 4 bi 2 ni 2 w 20 c 6 h 84 n 4 o 105 for green bulk crystals.Its molecular weight: 6196.87,
its structural formula is:
。
embodiment 2:
the present embodiment as different from Example 1 in step 1 by the Na of 4～5mmol
2
wO
4
be dissolved in the deionized water of 80ml, and be heated to 80 DEG C.Other step and parameter are identical with embodiment 1.
embodiment 3:
the present embodiment as different from Example 1 in step 1 by the Na of 5mmol
2
wO
4
be dissolved in the deionized water of 120ml, and be heated to 120 DEG C.Other step and parameter are identical with embodiment 1.
embodiment 4:
the present embodiment as different from Example 1 in step 1 by the Na of 4.2～4.8mmol
2
wO
4
be dissolved in the deionized water of 90～110ml, and be heated to 90～110 DEG C.Other step and parameter are identical with embodiment 1.
embodiment 5:
the present embodiment as different from Example 1 in step 1 under magnetic agitation, by the Na of 4.5mmol
2
wO
4
be dissolved in the deionized water of 100ml, and be heated to 100 DEG C.Other step and parameter are identical with embodiment 1.
embodiment 6:
the present embodiment as different from Example 1 in step 1 under magnetic agitation, by the Na of 4.7mmol
2
wO
4
be dissolved in the deionized water of 105ml, and be heated to 105 DEG C.Other step and parameter are identical with embodiment 1.
embodiment 7:
what the present embodiment was different from above-described embodiment 1-6 is in step 1, dropwise to add the HCl of 6mol/L to regulate pH to 5.0.Other step and parameter are identical with one of embodiment 1-6.
embodiment 8:
what the present embodiment was different from above-described embodiment 1-6 is in step 1, dropwise to add the HCl of 6mol/L to regulate pH to 7.0.Other step and parameter are identical with one of embodiment 1-6.
embodiment 9:
what the present embodiment was different from above-described embodiment 1-6 is in step 1, dropwise to add the HCl of 6mol/L to regulate pH to 5.5～6.0.Other step and parameter are identical with one of embodiment 1-6.
embodiment 10:
what the present embodiment was different from above-described embodiment 1-6 is in step 1, dropwise to add the HCl of 6mol/L to regulate pH to 6.0～6.5.Other step and parameter are identical with one of embodiment 1-6.
embodiment 11:
what the present embodiment was different from above-described embodiment 1-6 is in step 1, dropwise to add the HCl of 6mol/L to regulate pH to 6.5～7.0.Other step and parameter are identical with one of embodiment 1-6.
embodiment 12:
what the present embodiment was different from above-described embodiment 1-6 is in step 1, dropwise to add the HCl of 6mol/L to regulate pH to 5.5.Other step and parameter are identical with one of embodiment 1-6.
embodiment 13:
what the present embodiment was different from one of above-described embodiment 1-12 is by the NiCl of 0.5mmol in step 2
2
, 0.8mmol solid imidazoles and be dissolved in the Bi (NO of the 0.3mmol in 6mol/L HCl
3
)
3
join in solution A simultaneously, mix post-heating to 80 DEG C reaction 1h.Other step and parameter are identical with one of embodiment 1-12.
embodiment 14:
what the present embodiment was different from one of above-described embodiment 1-12 is by the NiCl of 1mmol in step 2
2
, 1.2mmol solid imidazoles and be dissolved in the Bi (NO of the 0.8mmol in 6mol/L HCl
3
)
3
join in solution A simultaneously, mix post-heating to 120 DEG C reaction 2h.Other step and parameter are identical with one of embodiment 1-12.
embodiment 15:
what the present embodiment was different from one of above-described embodiment 1-12 is by the NiCl of 0.8mmol in step 2
2
, 1.1mmol solid imidazoles and be dissolved in the Bi (NO of the 0.6mmol in 6mol/L HCl
3
)
3
join in solution A simultaneously, mix post-heating to 100 DEG C reaction 1.5h.Other step and parameter are identical with one of embodiment 1-12.
embodiment 16:
what the present embodiment was different from one of above-described embodiment 1-15 is to leave standstill 5 days after filtering in step 2.Other step and parameter are identical with one of embodiment 1-15.
embodiment 17:
what the present embodiment was different from one of above-described embodiment 1-15 is to leave standstill 10 days after filtering in step 2.Other step and parameter are identical with one of embodiment 1-15.
embodiment 18:
what the present embodiment was different from one of above-described embodiment 1-15 is to leave standstill 6～9 days after filtering in step 2.Other step and parameter are identical with one of embodiment 1-15.
embodiment 19:
what the present embodiment was different from one of above-described embodiment 1-15 is to leave standstill 7 days after filtering in step 2.Other step and parameter are identical with one of embodiment 1-15.
embodiment 20:
Present embodiment anticancer compound Na
4bi
2ni
2w
20c
6h
84n
4o
105synthetic method realize according to the following steps: one, under magnetic agitation, by the Na of 4.7mmol
2wO
4be dissolved in the deionized water of 100ml, and be heated to 100 DEG C, then dropwise add the HCl of 6mol/L to regulate pH to 6.0, obtain solution A; Two, by the NiCl of 0.7mmol
2, 1mmol solid imidazoles and be dissolved in the Bi (NO of the 0.5mmol in 6mol/L HCl
3)
3join in solution A simultaneously, mix post-heating to 100 DEG C reaction 1.5h, be then cooled to room temperature, after filtering, leave standstill 8 days, complete anticancer compound Na
4bi
2ni
2w
20c
6h
84n
4o
105synthetic; Wherein in step 2, the consumption of HCl is 10mL.
Claims (2)
1. a cancer therapy drug Na
4bi
2ni
2w
20c
6h
84n
4o
105synthetic method, it is characterized in that: the method comprises the steps:
(1) under magnetic agitation, by the Na of 4.7mmol
2wO
4be dissolved in the deionized water of 100ml, and be heated to 100 DEG C, then dropwise add the HCl of 6mol/L to regulate pH to 6.0, obtain solution A;
(2) by the NiCl of 0.7 mmol
2, 1 mmol solid imidazoles, be dissolved in the Bi (NO of 0.5 mmol in 10mL 6 mol/L HCl
3)
3join in solution A simultaneously, mix post-heating to 100 DEG C reaction 1.5 h, be then cooled to room temperature, after filtering, leave standstill 8 days.
2. the synthetic cancer therapy drug Na of method as claimed in claim 1
4bi
2ni
2w
20c
6h
84n
4o
105, it is characterized in that: molecular formula is: Na
4bi
2ni
2w
20c
6h
84n
4o
105, molecular weight: 6196.87, its structural formula is:
It under normal temperature, is green bulk crystals.
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| CN103011300B (en) * | 2012-12-24 | 2014-10-08 | 金华职业技术学院 | Preparation method of five-vacancy ferrum di-hepta-tungsten phosphorus oxygen cluster compound |
| CN103524567B (en) * | 2013-09-29 | 2016-03-23 | 哈尔滨工业大学 | A kind of anti-human osteosarcoma is containing the application of zinc heteropoly compound |
| CN104971359B (en) * | 2015-06-19 | 2017-11-28 | 昆明学院 | The purposes of the how cloudy oxometallic acid salt compound of organic inorganic hybridization |
| CN104922149B (en) * | 2015-06-19 | 2017-09-26 | 昆明学院 | Many the moon oxometallic acid salt compound [AlMo6H6O24]3‑Purposes |
| CN106986344B (en) * | 2017-04-18 | 2019-04-26 | 吉林大学 | Silicotungstate and its preparation method and application |
| CN107098392B (en) * | 2017-05-12 | 2019-03-05 | 昆明学院 | A kind of arsenowolframic acid sandwich type polyoxometalates compound and the preparation method and application thereof based on Manganic ion |
| CN107266507A (en) * | 2017-06-09 | 2017-10-20 | 扬州大学 | The sandwich type polymetallic tungstens hydrochlorate of imidazole covalent coordination, preparation method and applications |
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