CN104725429A - Synthesis method and application of complex Mn(H2L3)2 with anti-tumor activity - Google Patents
Synthesis method and application of complex Mn(H2L3)2 with anti-tumor activity Download PDFInfo
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- CN104725429A CN104725429A CN201510071714.6A CN201510071714A CN104725429A CN 104725429 A CN104725429 A CN 104725429A CN 201510071714 A CN201510071714 A CN 201510071714A CN 104725429 A CN104725429 A CN 104725429A
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- title complex
- analytically pure
- synthesis method
- complex
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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
- C07F13/00—Compounds containing elements of Groups 7 or 17 of the Periodic System
- C07F13/005—Compounds without a metal-carbon linkage
Abstract
The invention discloses a synthesis method and an application of a complex Mn(H2L3)2 with anti-tumor activity. Mn(H2L3)2 is characterized in that the molecular formula of Mn(H2L3)2 is C22H24Cl4MnN2O6, and the molecular weight is 609.17. The synthesis method comprises the steps that (1) 1.91g of analytically pure 3,5-dichloro salicylaldehyde is placed in a three-mouth flask, and mixed with 15ml of absolute ethyl alcohol, 1.051g of analytically pure 2-amido-2-methyl-1,3-propylene glycol and 10ml of absolute ethyl alcohol are added, heated, subjected to reflux agitation, cooled, and crystallized, and stood, and H3L3(H3L3=2-((3,5-dichloro-2-hydroxybenzmethylene) amido)-2-methyl-1,3-propylene glycol) is obtained; (2) 0.139g of H3L3 and 0.245g of analytically pure manganese acetate tetrahydrate are dissolved in 15-20ml of mixed solution of absolute ethyl alcohol and self-made distilled water with the volume ratio of 5:5; and (3) the formed solution in the step (2) is transferred to a reaction kettle, reacts, and is cooled, filtered and crystallized. Mn(H2L3)2 can serve as an anti-tumor drug to be applied; the synthesis method is simple in process, low in cost, good in repeatability and high in yield; and chemical constituents are easy to control.
Description
Technical field
The present invention relates to a kind of title complex Mn (H with anticancer activity
2l
3)
2synthesis and application.
Background technology
Recent study finds that salicylic aldehyde Schiff bases title complex has good antibacterial, anti-inflammatory, the biological activity such as antitumor, the synthesis of salicylic aldehyde presence of Schiff-base complex and bioactive research thereof have become the important topic of pharmaceutical chemistry, biologist's research, for social development and technical progress play the effect become more and more important.Particularly in short supply present of efficient new drug, the medicine of exploitation tool high anti-cancer activity solves one of efficient new drug problem method in short supply.Title complex Mn (H
2l
3)
2there is unique biological activity, low toxicity that design and synthesis has the application prospect medicine such as antibacterial, antitumor efficiently can be used as, there is potential use.
Summary of the invention
Object of the present invention is exactly be design and synthesis title complex Mn with anticancer activity (H
2l
3)
2, utilize solvent structure title complex Mn (H
2l
3)
2and as the application of antitumor drug.
Title complex Mn (the H that the present invention relates to
2l
3)
2molecular formula be: C
22h
24cl
4mnN
2o
6, molecular weight is: 609.17, and crystal structural data is in table one, and bond distance's bond angle data are in table two.All restraining effect is had to human hepatoma cell strain (BEL-7404), human liver cancer cell (HepG2), cervical cancer cell (HeLa), human bladder cancer cell (T-24) and normal liver cell's strain (HL-7702) growth of tumour cell.
Table one: Mn (H
2l
3)
2crystallographic parameter
Table two: Mn (H
2l
3)
2's
with bond angle (°)
| Mn1–O2 | 2.0253(18) | Mn1–N2 | 2.096(2) |
| Mn1–O3 | 1.8638(17) | Mn1–N1 | 2.015(2) |
| Mn1–O1 | 1.9040(17) | Mn1–O4 | 2.336(2) |
| O3–Mn1–O2 | 93.14(9) | N1–Mn1–O1 | 90.12(8) |
| O1–Mn1–O2 | 91.78(8) | N1–Mn1–N2 | 165.44(8) |
| O1–Mn1–O3 | 172.17(8) | O4–Mn1–O2 | 162.62(8) |
| N2–Mn1–O2 | 87.53(7) | O4–Mn1–O3 | 88.23(8) |
| N2–Mn1–O3 | 91.75(8) | O4–Mn1–O1 | 88.89(8) |
| N2–Mn1–O1 | 94.55(8) | O4–Mn1–N2 | 75.10(7) |
| N1–Mn1–O2 | 106.13(8) | O4–Mn1–N1 | 91.24(8) |
| N1–Mn1–O3 | 82.66(8) |
Described title complex Mn (H
2l
3)
2synthetic method concrete steps be:
(1) by analytically pure for 1.91g 3,5-dichloro-salicylaldehyde is placed in there-necked flask, the dehydrated alcohol heated and stirred adding 15ml treats that it dissolves completely, then the analytically pure 2-amino-2-methyl-1 of 1.051g is added, ammediol, then the dehydrated alcohol adding 10ml, heating in water bath, design temperature is 65 DEG C, return stirring about 120 minutes; The solution obtained cools under room temperature, crystallization of naturally volatilizing, and leaves standstill after 3 days, obtains yellow bulk crystals H
3l
3(H
3l
3=2-((3,5 two chloro-2-phenol methylene) is amino)-2-methyl isophthalic acid, ammediol).
(2) 0.139 gram of H step (1) synthesized
3l
315-20 ml volumes is dissolved in than being the dehydrated alcohol of 5:5 and making by oneself in the mixing solutions of distilled water with 0.245 gram of analytical pure four water manganous acetate.
(3) solution obtained by step (2) is proceeded in the reactor of tetrafluoroethylene, react 120 hours at 80-90 DEG C, be cooled to room temperature, filter, filtrate is volatilized under being placed in room temperature crystallization naturally, obtains monocrystalline level title complex Mn (H after 10 days
2l
3)
2; Title complex Mn (H is measured by single crystal diffractometer
2l
3)
2structure.
The present invention has that technique is simple, with low cost, chemical composition is easy to control, reproducible and output advantages of higher.
Accompanying drawing explanation
Fig. 1 is part H of the present invention
3l
3enforcement figure.
Fig. 2 is title complex Mn (H of the present invention
2l
3)
2enforcement figure.
Fig. 3 is title complex Mn (H of the present invention
2l
3)
2structure iron.
Fig. 4 is title complex Mn (H of the present invention
2l
3)
2three-dimensional structure accumulation graph.
Embodiment
Embodiment:
Title complex Mn (the H that the present invention relates to
2l
3)
2molecular formula be: C
22h
24cl
4mnN
2o
6, molecular weight is: 609.17, and crystal structural data is in table one, and bond distance's bond angle data are in table two.
Title complex Mn (H
2l
3)
2synthetic method concrete steps be:
(1) by analytically pure for 1.91g 3,5 dichloro-salicylaldehydes are placed in there-necked flask, the dehydrated alcohol heated and stirred adding 15ml treats that it dissolves completely, then the analytically pure 2-amino-2-methyl-1 of 1.051g is added, ammediol, then the dehydrated alcohol adding 10ml, heating in water bath, design temperature is 65 DEG C, return stirring about 120 minutes.The solution obtained cools under room temperature, crystallization of naturally volatilizing, and leaves standstill after 3 days, obtains yellow bulk crystals H
3l
3(H
3l
3=2-((the chloro-2-phenol methylene of 3,5-bis-) is amino)-2-methyl isophthalic acid, ammediol).
(2) 0.139 gram of H step (1) synthesized
3l
315-20 ml volumes is dissolved in than being the dehydrated alcohol of 5:5 and making by oneself in the mixing solutions of distilled water with 0.245 gram of analytical pure four water manganous acetate.
(3) solution obtained by step (2) is proceeded in the reactor of tetrafluoroethylene, react 120 hours at 80-90 DEG C, be cooled to room temperature, filter, filtrate is volatilized under being placed in room temperature crystallization naturally, obtains monocrystalline level title complex Mn (H after 10 days
2l
3)
2; Title complex Mn (H is measured by single crystal diffractometer
2l
3)
2structure.
Title complex Mn (H with anticancer activity
2l
3)
2the proliferation inhibition activity of various human tumor cell line is tested:
(1) cell strain and cell cultures:
Human hepatoma cell strain (BEL-7404) is selected in this experiment, human liver cancer cell (HepG2), cervical cancer cell (HeLa), human bladder cancer cell (T-24), 5 kinds of human cell lines such as normal liver cell's strain (HL-7702).All cells strain is all cultivated in the RPMI-1640 nutrient solution containing 10wt% calf serum, 100U/mL penicillin, 100U/mL Streptomycin sulphate, puts 37 DEG C containing volumetric concentration 5%CO
2cultivate in incubator.
(2) preparation of testing compound:
Title complex Mn (H used
2l
3)
2purity>=95%, will its DMSO liquid storage physiological buffer dilute after be mixed with the whole solution of 20 μm of ol/L, wherein final concentration≤1% of solubility promoter DMSO, under testing this concentration, compound is to the suppression degree of various growth of tumour cell.
(3) cell growth inhibition test (mtt assay):
1) tumour cell of taking the logarithm vegetative period, after tryptic digestion, the cell suspension that concentration is 5000/ml is mixed with the nutrient solution containing 10% calf serum, be inoculated in 96 well culture plates with every hole 190 μ l, make hole, cell density to 1000 ~ 10000 to be measured (the aseptic PBS of marginal pore fills);
2) 5%CO
2, hatch 24 hours for 37 DEG C, be paved with at the bottom of hole to cell monolayer, every hole adds the medicine 10 μ L of finite concentration gradient, and each concentration gradient establishes 4 multiple holes;
3) 5%CO
2, hatch 48 hours for 37 DEG C, observe under inverted microscope;
4) every hole adds the MTT solution (5mg/mL PBS, i.e. 0.5%MTT) of 10 μ L, continues cultivation 4 hours;
5) stop cultivating, carefully suck nutrient solution in hole, the DMSO that every hole adds 150 μ L fully dissolves first a ceremonial jade-ladle, used in libation precipitation, and after vibrator mixing, be 570nm at microplate reader wavelength, reference wavelength is the optical density value that 450nm measures each hole;
6) zeroing hole (substratum, MTT, DMSO) is set simultaneously, control wells (the medicine dissolution medium of cell, same concentrations, nutrient solution, MTT, DMSO).
7) according to the optical density value (OD value) recorded, judge viable cell quantity, OD value is larger, and cytoactive is stronger.Utilize formula:
Calculate the inhibiting rate of drug on tumor Growth of Cells, then calculate the IC of each test-compound to various human tumor cell line and Human normal hepatocyte strain respectively with Bliss method
50value.
Title complex Mn (H
2l
3)
2to the inhibiting rate of human hepatoma cell strain (BEL-7404), human liver cancer cell (HepG2), cervical cancer cell (HeLa), human bladder cancer cell (T-24) and normal liver cell's strain (HL-7702) growth of tumour cell in table three, to the IC of various human tumor cell line and Human normal hepatocyte strain
50value is in table four.
Table three: Mn (H
2l
3)
2to the inhibiting rate of different cell strain
| BEL-7404 | HepG2 | HeLa | T-24 | HL-7702 |
| 37.18±1.21 | 41.66±0.99 | 51.82±0.91 | 51.98±1.11 | 55.48±1.22 |
Table four: Mn (H
2l
3)
2to the half-inhibition concentration (IC of different cell strain
50, μM)
| BEL-7404 | HepG2 | HeLa | T-24 | HL-7702 |
| 30.22±1.15 | 21.91±1.07 | 13.67±0.88 | 15.35±1.63 | 18.58±1.16 |
Claims (2)
1. a title complex Mn (H with anticancer activity
2l
3)
2, it is characterized in that title complex Mn (H
2l
3)
2molecular formula is: C
22h
24cl
4mnN
2o
6, molecular weight is: 609.17, title complex Mn (H
2l
3)
2have good antitumour activity, crystal structural data is in table one, and bond distance's bond angle data are in table two;
Described title complex Mn (H
2l
3)
2synthetic method concrete steps be:
(1) by analytically pure for 1.91g 3,5-dichloro-salicylaldehyde is placed in there-necked flask, the dehydrated alcohol heated and stirred adding 15ml treats that it dissolves completely, then the analytically pure 2-amino-2-methyl-1 of 1.051g is added, ammediol, then the dehydrated alcohol adding 10ml, heating in water bath, design temperature is 65 DEG C, return stirring 120 minutes; The solution obtained cools under room temperature, crystallization of naturally volatilizing, and leaves standstill after 3 days, obtains yellow bulk crystals H
3l
3, H
3l
3for 2-((the chloro-2-phenol methylene of 3,5-bis-) is amino)-2-methyl isophthalic acid, ammediol;
(2) by H that 0.139 gram of step (1) is synthesized
3l
315-20 ml volumes is dissolved in than being the dehydrated alcohol of 5:5 and making by oneself in the mixing solutions of distilled water with 0.245 gram of analytical pure four water manganous acetate;
(3) solution obtained by step (2) is proceeded in the reactor of tetrafluoroethylene, react 120 hours at 80-90 DEG C, be cooled to room temperature, filter, filtrate is volatilized under being placed in room temperature crystallization naturally, obtains monocrystalline level title complex Mn (H after 10 days
2l
3)
2; Title complex Mn (H is measured by single crystal diffractometer
2l
3)
2structure;
Table one: Mn (H
2l
3)
2crystallographic parameter
Table two: Mn (H
2l
3)
2bond distance
with bond angle (°)
2. title complex title complex Mn (H according to claim 1
2l
3)
2application, it is characterized in that title complex Mn (H
2l
3)
2apply as antitumor drug.
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|---|---|---|---|
| CN201510071714.6A CN104725429A (en) | 2015-02-11 | 2015-02-11 | Synthesis method and application of complex Mn(H2L3)2 with anti-tumor activity |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510071714.6A CN104725429A (en) | 2015-02-11 | 2015-02-11 | Synthesis method and application of complex Mn(H2L3)2 with anti-tumor activity |
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|---|---|
| CN104725429A true CN104725429A (en) | 2015-06-24 |
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ID=53449905
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|---|---|---|---|
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106939023A (en) * | 2017-04-01 | 2017-07-11 | 聊城大学 | Manganese ion complex and preparation method and application based on chiral tetrahedron-type metal cluster |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101528673A (en) * | 2006-10-26 | 2009-09-09 | 住友化学株式会社 | Method for producing asymmetric copper complex crystal |
-
2015
- 2015-02-11 CN CN201510071714.6A patent/CN104725429A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101528673A (en) * | 2006-10-26 | 2009-09-09 | 住友化学株式会社 | Method for producing asymmetric copper complex crystal |
Non-Patent Citations (2)
| Title |
|---|
| D.L.PENG: "Synthesis and Crystal Structures of Manganese(IV) Complexes with Tridentate Schiff Bases", 《RUSSIAN JOURNAL OF COORDINATION CHEMISTRY》 * |
| ERNEST M. HODNETT ET AL.: "Schiff Bases of Salicylaldehyde and Their Cobalt(II) Derivatives as Anititumor Agents", 《PROCEEDINGS OF THE OKLAHOMA ACADEMY OF SCIENCE》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106939023A (en) * | 2017-04-01 | 2017-07-11 | 聊城大学 | Manganese ion complex and preparation method and application based on chiral tetrahedron-type metal cluster |
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