CN102584871A - Rare earth coordination compound containing Schiff base and bipyridyl and preparation method and bacteriostasis application thereof - Google Patents
Rare earth coordination compound containing Schiff base and bipyridyl and preparation method and bacteriostasis application thereof Download PDFInfo
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- CN102584871A CN102584871A CN201210003832XA CN201210003832A CN102584871A CN 102584871 A CN102584871 A CN 102584871A CN 201210003832X A CN201210003832X A CN 201210003832XA CN 201210003832 A CN201210003832 A CN 201210003832A CN 102584871 A CN102584871 A CN 102584871A
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Abstract
The invention provides a rare earth coordination compound containing a salicylidene glycine Schiff base and bipyridyl and a preparation method thereof. The rare earth coordination compound can be applied to bacteriostasis of colon bacillus. The rare earth coordination compound is characterized in that: the chemical formula of the coordination compound is RE(Sal-Gly)(Bipy)L.H2O, wherein RE is a rare earth ion; Sal-Gly is a salicylidene glycine Schiff base; Bipy is 2,2'-bipyridyl; and L is a negative univalent inorganic negative ion. The preparation method disclosed by the invention has the advantages of easiness and convenience for operating, mild conditions, high controllability, short treatment time and low energy consumption. A rare earth coordination compound bacteriostat has a small using amount of rare earth, and a good bacteriostasis effect is achieved under the synergetic action of rare earth ions and an organic ligand.
Description
Technical field
The present invention relates to a kind of rare earth organic complex and preparation method thereof and antibacterial application, relate in particular to a kind of rare earth compounding that contains salicylidene glycocoll Schiff's base and dipyridyl and preparation method thereof and antibacterial application.
Background technology
The research and development of different types of antiseptic-germicide have in recent years obtained noticeable progress, wherein are the antibacterial agent of representative with the rare earth compounding class, owing to it has low toxicity, spinoff is little and broad spectrum antibiotic activity receives much concern.Though the antifungal mechanism of rare earth compounding early has research, there is not unified explanation so far.Generally relatively a kind of antifungal mechanism of approval is proposed by A.Chaudhary.After this mechanism thought that rare earth ion generates title complex, it was because chelate effect has increased the fat-soluble of title complex that the bacteriostatic action of title complex strengthens, so that title complex can better penetrate the lipoid layer of microorganism cells film, thereby influenced the normal physiological process of cell.The bacteriostatic activity of transition and REE title complex generally is higher than part, explains that synergy has taken place for metals ion and part, has played certain promoter action to its biological activity.Part has strengthened the ability of the fat-soluble and permeate through cell membranes of title complex, has brought into play the effect of similar substrates, is carrying metals ion and is arriving acceptor, has improved the effective dose in metals ion combination target site.Metals ion maybe with cell walls, cytolemma, enzyme, protein, DNA, RNA effect; Stronger complexing action has taken place with O, S, N atom in these structures; Disturbed its normal biochemical functions, thereby suppressed the growth of bacterium even caused its death.Rare earth ion can with the phosphoryl bonding in the transfer ribonucleic acid (tRNA) that supplies the examination bacterium, suppress the activity and the function of its nucleicacidase, thereby the growth of bacterium be suppressed.
Amino-acid schiff base contains a plurality of nitrogen-atoms and Sauerstoffatom; It is one type of important bio-ligand; Because cancerous tumor cell is more much bigger to amino acid whose demand than normal cell, thus amino-acid schiff base just maybe anticancer base be carried in the cancerous tumor cell, thereby increase the selectivity kill and wound cancerous tumor cell.Years of researches find that some Schiff's base have good sterilization antitumous effect, and its title complex is because of having stronger fat-soluble and cell-penetrating property, and difficult generation resistance, have better pharmaceutical value.
Summary of the invention
One of the object of the invention provides a kind of rare earth compounding that contains salicylidene glycocoll Schiff's base and dipyridyl and preparation method thereof.
Another object of the present invention provides a kind of rare earth compounding fungistat that contains salicylidene glycocoll Schiff's base and dipyridyl, and this fungistat can be used for colibacillary antibacterial.
The object of the invention is realized through following technical scheme:
A kind of ternary complex that contains rare earth ion and salicylidene glycocoll Schiff's base and dipyridyl, the chemical formula that it is characterized in that it are (Bipy) LH of RE (Sal-Gly)
2O, wherein RE is a rare earth ion, and Sal-Gly is a salicylidene glycocoll Schiff's base, and Bipy is 2,2 '-dipyridyl, L is negative univalent inorganic anion, the structural formula of salicylidene glycocoll Schiff's base (Sal-Gly) is:
Described RE rare earth ion is selected from La
3+, Ce
3+, Pr
3+, Nd
3+, Pm
3+, Sm
3+, Gd
3+, Tb
3+, Dy
3+, Ho
3+, Y
3+, Er
3+, Tm
3+, Yb
3+In one or more.
Described negative univalent inorganic anion (L) is selected from Cl
-, Br
-, I
-, ClO
4 -, NO
3 -In one or more.
The ternary complex RE (Sal-Gly) that a kind of preparation contains rare earth ion and salicylidene glycocoll Schiff's base and dipyridyl is LH (Bipy)
2The method of O may further comprise the steps:
(1) Bipy is used dissolve with methanol,, stir dissolving down, add a certain amount of inorganic salt of rare earth REL at 30-65 ℃
3Methanol solution, stirring reaction 0.5-10 hour, add a certain amount of Sal-Gly methanol solution then, regulate the pH value to 5-8, deposition appears, continued heated and stirred 0.5-24 hour, left standstill 1-10 hour.
Wherein, the concentration of the methanol solution of described Bipy is 0.001-1.0mol/L;
Wherein, described inorganic salt of rare earth REL
3With the mol ratio of Bipy be 1: 1;
Wherein, the mol ratio of described Sal-Gly and Bipy is 1: 1;
Wherein, described temperature of reaction further is optimized for 50 ℃ to 65 ℃, and said pH value scope further is optimized for 6-7, and the time of said stirring reaction further is optimized for 1-5 hour, and the time of said continuation heated and stirred further is optimized for 1-5 hour;
(2) mixture with step (1) gained filters, and filter cake is used methanol wash, and oven dry gets rare earth organic complex.
A kind of organic rare-earth ligand fungistat is in the application that suppresses on the intestinal bacteria." disinfection technology standard " standard that bacteriostatic experiment is issued according to Ministry of Health of the People's Republic of China 2002; Adopt dull and stereotyped filter paper method, nutrient broth dilution method, substratum diffusion process and vibration flask method to represent to antibiotic performance test; And, anti-microbial property is estimated with reference to " the People's Republic of China's chemical industry standard: inorganic antiseptic------performance and evaluation " of the National Development and Reform Commission of the People's Republic of China issue.Before using, all experimental articles of this research all need could use at 121 ℃ of high-temperature sterilization 15min, and operation under Bechtop.What this experiment was adopted is the substratum diffusion process.
The invention has the advantages that: (1) the present invention has studied the fungistatic effect of multiple REE title complex under different concns; (2) rare earth consumption of the present invention is few, good antimicrobial effect; (3) the present invention has widened the range of application of REE.
Specific embodiments
Embodiment 1
Take by weighing 2,2 '-dipyridyl 5mmol is dissolved in the 50mL methyl alcohol, 50 ℃ of heating for dissolving, constantly stir down, and be the La (NO of 0.1mol/L with 50mL concentration
3)
3Methanol solution dropwise joins in the above-mentioned ligand solution, heated and stirred 1h.Be that the methanol solution of the salicylidene glycocoll Schiff's base of 0.1mol/L dropwise joins in the above-mentioned reaction system with 50mL concentration then,, continue heated and stirred 2h, produce deposition in a large number, leave standstill 10h with the methanol solution regulation system pH value to 6 of Pottasium Hydroxide.Solid precipitation after filtering, with methanol wash for several times, the gained solid is dried to constant weight, the pressed powder that obtains is (Bipy) (NO of rare earth ternary complexes La (Sal-Gly)
3) H
2The O product.Its elementary composition analytical results is: experimental value (theoretical value), C%, 40.93 (41.32); H%, 3.41 (3.10); N%, 9.81 (10.14); La%, 25.06 (25.15).
Embodiment 2
Take by weighing 2,2 '-dipyridyl 5mmol is dissolved in the 50mL methyl alcohol, 60 ℃ of heating for dissolving, constantly stir down, and be the Nd (NO of 0.1mol/L with 50mL concentration
3)
3Methanol solution dropwise joins in the above-mentioned ligand solution, heated and stirred 1.5h.Be that the methanol solution of the salicylidene glycocoll Schiff's base of 0.1mol/L dropwise joins in the above-mentioned reaction system with 50mL concentration then,, continue heated and stirred 2h, produce deposition in a large number, leave standstill 10h with the methanol solution regulation system pH value to 6.5 of Pottasium Hydroxide.Solid precipitation after filtering, with methanol wash for several times, the gained solid is dried to constant weight, the pressed powder that obtains is (Bipy) (NO of rare earth ternary complexes Nd (Sal-Gly)
3) H
2The O product.Its elementary composition analytical results is: experimental value (theoretical value), C%, 40.77 (40.93); H%, 3.25 (3.07); N%, 9.59 (10.05); Nd%, 25.61 (25.87).
Embodiment 3
Take by weighing 2,2 '-dipyridyl 5mmol is dissolved in the 50mL methyl alcohol, 65 ℃ of heating for dissolving, constantly stir down, and be the Sm (NO of 0.1mol/L with 50mL concentration
3)
3Methanol solution dropwise joins in the above-mentioned ligand solution, heated and stirred 5h.Be that the methanol solution of the salicylidene glycocoll Schiff's base of 0.1mol/L dropwise joins in the above-mentioned reaction system with 50mL concentration then,, continue heated and stirred 1h, produce deposition in a large number, leave standstill 10h with the methanol solution regulation system pH value to 6.2 of Pottasium Hydroxide.Solid precipitation after filtering, with methanol wash for several times, the gained solid is dried to constant weight, the pressed powder that obtains is (Bipy) (NO of rare earth ternary complexes Sm (Sal-Gly)
3) H
2The O product.Its elementary composition analytical results is: experimental value (theoretical value), C%, 40.17 (40.48); H%, 3.22 (3.04); N%, 9.67 (9.94); Sm%, 26.45 (26.67).
Embodiment 4
Take by weighing 2,2 '-dipyridyl 5mmol is dissolved in the 50mL methyl alcohol, 60 ℃ of heating for dissolving, constantly stir down, and be the Y (NO of 0.1mol/L with 50mL concentration
3)
3Methanol solution dropwise joins in the above-mentioned ligand solution, heated and stirred 2h.Be that the methanol solution of the salicylidene glycocoll Schiff's base of 0.1mol/L dropwise joins in the above-mentioned reaction system with 50mL concentration then,, continue heated and stirred 2h, produce deposition in a large number, leave standstill 5h with the methanol solution regulation system pH value to 6.7 of Pottasium Hydroxide.Solid precipitation after filtering, with methanol wash for several times, the gained solid is dried to constant weight, the pressed powder that obtains is (Bipy) (NO of rare earth ternary complexes Y (Sal-Gly)
3) H
2The O product.Its elementary composition analytical results is: experimental value (theoretical value), C%, 45.09 (45.44); H%, 3.70 (3.41); N%, 10.93 (11.15); Y%, 17.52 (17.70).
Embodiment 5
Take by weighing 2,2 '-dipyridyl 5mmol is dissolved in the 50mL methyl alcohol, 65 ℃ of heating for dissolving, constantly stir down, and be the Tb (NO of 0.1mol/L with 50mL concentration
3)
3Methanol solution dropwise joins in the above-mentioned ligand solution, heated and stirred 2h.Be that the methanol solution of the salicylidene glycocoll Schiff's base of 0.1mol/L dropwise joins in the above-mentioned reaction system with 50mL concentration then,, continue heated and stirred 2h, produce deposition in a large number, leave standstill 5h with the methanol solution regulation system pH value to 6.2 of Pottasium Hydroxide.Solid precipitation after filtering, with methanol wash for several times, the gained solid is dried to constant weight, the pressed powder that obtains is (Bipy) (NO of rare earth ternary complexes Tb (Sal-Gly)
3) H
2The O product.Its elementary composition analytical results is: experimental value (theoretical value), C%, 39.97 (39.88); H%, 2.85 (2.99); N%, 9.95 (9.79); Tb%, 27.59 (27.77).
EXPERIMENTAL EXAMPLE 1
Inhibition zone method is adopted in this test.
Take by weighing 1g peptone, 0.5g yeast powder, 1.5g agar powder, 1gNaCl successively and put into Erlenmeyer flask.Add 100mL zero(ppm) water again, mixing boils 15min, and packing is poured in the petridish, leaves standstill the solid that congeals under the room temperature and is substratum.
Take by weighing 0.1g peptone, 0.05g yeast powder, 0.1g NaCl successively, use the 10mL dissolved in distilled water, add 10 μ L Escherichia coli bacteria liquids, 37 ℃ of constant temperature water bath vibration 1h add substratum with the cultured bacterium liquid of 0.3mL, continue to cultivate 4h in 37 ℃ of baking ovens.
With DMF is solvent, with (Bipy) (NO of each free part (Sal-Gly, Bipy) and title complex RE (Sal-Gly)
3) H
2O (RE=La, Nd, Sm, Tb and Y) is mixed with 0.004,0.008 and 0.012molL respectively
-1Solution, test them respectively to colibacillary restraining effect.With diameter is that the circular filter paper sheet of 1.0cm is affixed on the peptone solid medium of inoculating bacterium liquid, and free ligand (Sal-Gly, Bipy) and the RE (Sal-Gly) that gets 20 μ L solvents, each concentration respectively be (NO (Bipy)
3) H
2The O complex solution drips in the middle of filter paper, after 37 ℃ of constant temperature are cultivated 16-18h, through fungistat to the colibacillary growth of the diffusion suppressing of substratum; Measure their antibacterial circle diameter respectively with vernier callipers, parallel laboratory test three times, and statistics; Calculating mean value, the result sees table 1.
Table 1 solvent, part, rare earth nitrate, rare earth compounding RE (Sal-Gly) be (NO (Bipy)
3) H
2The antibacterial circle diameter of O (mm)
The antibacterial circle diameter of measured matter shows that more greatly bacteriostatic activity is strong more.Visible from table 1, antibacterial circle diameter is all less than 10mm under each concentration for solvent DMF, part Bipy, each rare earth nitrate, and the antibacterial circle diameter of part Sal-GlyK is no more than 11mm, and visible solvent, part, each rare earth nitrate do not have bacteriostatic action basically.RE (Sal-Gly) is (NO (Bipy)
3) H
2O title complex concentration is at 0.004molL
-1The time, antibacterial circle diameter 13-16mm.RE (Sal-Gly) is (NO (Bipy)
3) H
2O title complex concentration is at 0.008molL
-1The time, antibacterial circle diameter 16-19mm.RE (Sal-Gly) is (NO (Bipy)
3) H
2O title complex concentration is at 0.012molL
-1The time, antibacterial circle diameter 18-24mm.Show thus: the fungistatic effect of (1) rare earth ternary complexes is better than independent rare earth nitrate, Sal-GlyK, Bipy; (2) for a kind of rare earth compounding, its bacteriostatic activity strengthens with the increase of title complex concentration.
Claims (9)
1. ternary complex that contains rare earth ion and salicylidene glycocoll Schiff's base and dipyridyl, the chemical formula that it is characterized in that it is (Bipy) LH of RE (Sal-Gly)
2O, wherein RE is a rare earth ion, and Sal-Gly is a salicylidene glycocoll Schiff's base, and Bipy is 2,2 '-dipyridyl, L is for being selected from Cl
-, Br
-, I
-, ClO
4 -, NO
3 -In one or more negative monovalence inorganic anion, the structural formula of salicylidene glycocoll Schiff's base (Sal-Gly) is:
2. one kind prepares (Bipy) LH of ternary complex RE (Sal-Gly) that contains rare earth ion and salicylidene glycocoll Schiff's base and dipyridyl
2The method of O may further comprise the steps:
(1) Bipy is used dissolve with methanol,, stir dissolving down, add a certain amount of inorganic salt of rare earth REL at 30-65 ℃
3Methanol solution, stirring reaction 0.5-10 hour, add a certain amount of Sal-Gly methanol solution then, regulate the pH value to 5-8, deposition appears, continued heated and stirred 0.5-24 hour, left standstill 1-10 hour;
(2) mixture with step (1) gained filters, and filter cake washs with anhydrous methanol, and oven dry gets rare earth organic complex.
3. title complex as claimed in claim 1 is characterized in that, described RE rare earth ion is selected from La
3+, Ce
3+, Pr
3+, Nd
3+, Pm
3+, Sm
3+, Gd
3+, Tb
3+, Dy
3+, Ho
3+, Y
3+, Er
3+, Tm
3+, Yb
3+In one or more.
4. method as claimed in claim 2 is characterized in that, the concentration of the methanol solution of said Bipy is 0.001-1.0mol/L.
5. method as claimed in claim 2 is characterized in that, said inorganic salt of rare earth REL
3With the mol ratio of Bipy be 1: 1, the mol ratio of said Sal-Gly and Bipy is 1: 1.
6. method as claimed in claim 2 is characterized in that, said temperature of reaction can further be optimized for 50 ℃ to 65 ℃.
7. method as claimed in claim 2 is characterized in that, said pH value scope can further be optimized for 6-7.
8. method as claimed in claim 2 is characterized in that the time of said stirring reaction further is optimized for 1-5 hour, and the time of said continuation heated and stirred further is optimized for 1-5 hour.
One kind contain right require 1 described title complex as fungistat in the application that suppresses on the intestinal bacteria.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112673006A (en) * | 2018-09-13 | 2021-04-16 | 住友化学株式会社 | Bipyridine compound and use thereof |
| FR3108609A1 (en) * | 2020-03-26 | 2021-10-01 | Compagnie Generale Des Etablissements Michelin | SYNTHESIS OF OLEFIN POLYMERS |
| FR3108612A1 (en) * | 2020-03-26 | 2021-10-01 | Compagnie Generale Des Etablissements Michelin | Cationic yttrium organometallic complex |
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2012
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| US20040223915A1 (en) * | 2001-08-06 | 2004-11-11 | Faustus Forschungs Cie. Translational Cancer Research Gmbh | Cytostatic cerium compounds |
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Cited By (4)
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|---|---|---|---|---|
| CN112673006A (en) * | 2018-09-13 | 2021-04-16 | 住友化学株式会社 | Bipyridine compound and use thereof |
| CN112673006B (en) * | 2018-09-13 | 2024-05-03 | 住友化学株式会社 | Bipyridine compound and use thereof |
| FR3108609A1 (en) * | 2020-03-26 | 2021-10-01 | Compagnie Generale Des Etablissements Michelin | SYNTHESIS OF OLEFIN POLYMERS |
| FR3108612A1 (en) * | 2020-03-26 | 2021-10-01 | Compagnie Generale Des Etablissements Michelin | Cationic yttrium organometallic complex |
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Application publication date: 20120718 |