CN103232486A - Vanadium oxide complex as well as preparation method and application thereof - Google Patents

Vanadium oxide complex as well as preparation method and application thereof Download PDF

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CN103232486A
CN103232486A CN2013101656278A CN201310165627A CN103232486A CN 103232486 A CN103232486 A CN 103232486A CN 2013101656278 A CN2013101656278 A CN 2013101656278A CN 201310165627 A CN201310165627 A CN 201310165627A CN 103232486 A CN103232486 A CN 103232486A
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sulfydryl
amino
chloro
vanadyl
title complex
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袁彩霞
卢丽萍
朱苗力
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Shanxi University
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Abstract

The invention provides a vanadium oxide complexa and a preparation method thereof and an application of the complex as a protein tyrosine phosphatase 1B (PTP1B) inhibitor. The vanadium oxide complex provided by the invention is 5-chloro-salicyladehyde condens-4-amino-5-sulfydryl-1, 2, 4- triazole Schiff base vanadium oxide. The preparation method of the vanadium oxide complex comprises steps of: dissolving a 5-chloro-salicyladehyde condens-4-amino-5-sulfydryl-1, 2, 4- triazole Schiff base ligand into absolute ethyl alcohol; dripping triethylamine of the same molar weight; heating and stirring the ligand to be dissolved; and then adding the absolute ethyl alcohol solution with the dissolved triethylamine the molar weight of which is the same as that of absolute ethyl alcohol solution, stirring, refluxing, cooling, filtering, collecting a mother liquid and separating yellow massive crystals out. The complex is simple in synthesizing method, is prepared by easily obtained raw materials, and has an obvious inhibition function on the activity of PTP1B with nanomolar concentration; and the prepared complex can be used as the protein tyrosine phosphatase 1B inhibitor.

Description

A kind of vanadyl title complex and its preparation method and application
Technical field
The present invention relates to transition metal complex, be specifically related to a kind of vanadyl title complex and preparation method thereof, and this title complex is as the application of protein-tyrosine phosphatase 1B inhibitor.
Background technology
Protein-tyrosine-phosphatase (PTPs) is the metal-free enzyme of a class that extensively is present in the organism, it and this reversible dynamic process of the common modulin tyrosine phosphorylation of protein kinase, wherein, protein-tyrosine makes protein phosphorylation, and protein kinase then makes the albumen dephosphorylation.In human body, there be more than 100 kind of PTPs to be considered to relevant with the approach of various enhancings or inhibition signal transduction.PTPs can cell cycle regulation and the transduction of signal, and aspect the response of cell signal, it can be by uniting to come the effect degree of modulin tyrosine phosphorylation with the protein tyrosine phosphatase kinases.The unusual control path of these signalling systems is found relevant with numerous disease.Abnormal PTPs activity can cause comprising the generation of the numerous disease of cancer, diabetes and rheumatic arthritis etc.
PTP 1B (PTP1B) is the non-receptor type tyrosine phosphatase of classics in the PTPs family, in insulin signaling pathway, play important negative regulation effect, the inside and outside is discovered at present, the expression of PTP1B increases greatly in the insulin target tissue in the type ii diabetes patient body that is caused by insulin resistant, the activation of insulin receptor tyrosine and the signal conduction of Regular Insulin have been blocked in the overexpression of PTP1B, so PTP1B has become diabetes and the generally acknowledged treatment target spot of obesity, also become in the world the focus of a lot of R﹠D institutions and drugmaker's research and development new drug, specificity is combined and the small molecules of effect and searching is carried out with PTP1B, research small molecules and PTP1B interact, and then becoming research and development is the basis of the new drug of target spot with PTP1B.In recent years, the research of PTP1B inhibitor has caused people's interest widely, and is a lot of about the report of PTP1B inhibitor both at home and abroad at present, but major part all concentrates on the organic micromolecule compound aspect.Because the distinctive biological activity of metal ion, the inorganic molecules compound that can effectively suppress PTP1B more and more causes people's attention, and some are efficient, low toxicity, specific inorganic molecules compound are expected to become novel antidiabetic medicine.
People were the most active to VO (IV) the vanadyl class Study on Complexes with insulin activity in recent years, development is also the fastest, and each country is also all stepping up to develop this type of antidiabetic medicine.At present except BMOV, some coordination modes are that the title complex of VO (N2O2), VO (O2S2), VO (N2S2), VO (N4), VO (S4) also has para-insulin character, but coordination mode is the title complex para-insulin character of VO2 (NSO) yet there are no report, so our preparation has also been studied the Schiff's base vanadyl title complex with para-insulin character based on the PTP1B target spot, for treatment of diabetes provides a kind of new drug development approach.
Summary of the invention
The object of the present invention is to provide a kind of vanadyl title complex and preparation method thereof, and this title complex is as the application of inhibitors of protein tyrosine phosphatase.
A kind of vanadyl title complex provided by the invention is 5-chloro-salicylic aldehyde contracting-4-amino-5-sulfydryl-1,2,4-triazole Schiff's base vanadyl, and its molecular formula is C 9H 6ClN 4O 3SV, molecular weight are 336.63, and structural formula is:
The preparation method of a kind of vanadyl title complex provided by the invention comprises the steps:
(1) synthetic (as: chemical reagent, 2009,31 (10), 785-788) 4-amino-5-sulfydryl-1,2,4-triazole;
(2) synthetic 5-chloro-salicylic aldehyde contracting-4-amino-5-sulfydryl-1,2,4-triazole schiff base ligand: with equimolar amount 4-amino-5-sulfydryl-1,2,4-triazole and 5-chloro-salicylic aldehyde are dissolved in dehydrated alcohol respectively, stir down, 5-chloro-salicylic aldehyde's ethanol solution is added drop-wise to 4-amino-5-sulfydryl-1,2, in the ethanol solution of 4-triazole, drip the vitriol oil of 1-2 times of molar weight then, faint yellow precipitation occurs, reflux after 4 hours, cooling, filter, solid is recrystallization in dehydrated alcohol;
(3) synthetic vanadyl title complex of the present invention: with methyl ethyl diketone vanadyl and the 5-chloro-salicylic aldehyde contracting-4-amino-5-sulfydryl-1 of equimolar amount, 2,4-triazole schiff base ligand is dissolved in dehydrated alcohol respectively, heated and stirred 5-chloro-salicylic aldehyde contracting-4-amino-5-sulfydryl-1,2, the ethanol solution of 4-triazole schiff base ligand, the triethylamine that drips equimolar amount makes the part dissolving, then, add the ethanol solution of methyl ethyl diketone vanadyl again, stirring and refluxing is after 4 hours, cooling, filter, collect mother liquor, separate out yellow bulk crystals.
The reaction formula of above-mentioned synthetic method is:
Figure BDA00003153010400022
The title complex that the present invention makes can be used as protein-tyrosine phosphatase 1B inhibitor.This title complex is 78nm to the half-inhibition concentration of PTP1B.Suppressing type is the state of conflict inhibitor, suppresses constant K iValue is 109nM, and title complex is 0.95082 with the interactional bonding ratio of PTP1B, and the bonding constant is: 1.06 * 10 6M -1
Advantage of the present invention and effect
Title complex synthetic method of the present invention is simple, raw material is easy to get, just the activity to PTP 1B (PTP1B) has remarkable restraining effect when nmole level concentration, therefore, title complex of the present invention has the para-insulin activity, for treatment of diabetes provides a kind of new drug development approach.
Description of drawings
The crystalline structure figure of Fig. 1 vanadyl title complex of the present invention;
Fig. 2 vanadyl title complex of the present invention suppresses the IC of PTP1B activity 50The pH-value determination pH curve;
Fig. 3 vanadyl title complex of the present invention is to the inhibition type curve of PTP1B;
Fig. 4 vanadyl title complex of the present invention is to the inhibition constant curve of PTP1B;
Fig. 5 vanadyl title complex of the present invention is to the fluorescent quenching collection of illustrative plates of PTP1B;
Fig. 6 vanadyl title complex of the present invention compares curve with bonding constant and the bonding of PTP1B;
Embodiment
The invention will be further described below in conjunction with accompanying drawing and example.
Embodiment 1
The preparation of title complex
(1) synthetic 4-amino-5-sulfydryl-1,2,4-triazole: get 10mmol(1.06g) two thiosemicarbazide are in round-bottomed flask, add the 10mL formic acid solution, stirring and refluxing 4h is chilled to room temperature, underpressure distillation goes out unreacted formic acid, wash thick product, the water recrystallization obtains the white crystals product;
(2) synthetic 5-chloro-salicylic aldehyde contracting-4-amino-5-sulfydryl-1,2,4-triazole schiff base ligand: get 5mmol(0.58g) 4-amino-5-sulfydryl-1,2, the 4-triazole adds the 50ml anhydrous alcohol solution in round-bottomed flask, stir Dropwise 5 mmol(0.78g down) 5-chloro-salicylic aldehyde's ethanol solution 40ml and the 0.4ml vitriol oil, a large amount of faint yellow precipitations appear, after the reflux 4 hours, cooling is filtered, pressed powder is recrystallization in dehydrated alcohol, separates out faint yellow crystallite;
Determination of elemental analysis: C 9H 7ClN 4Be theoretical value (%): C42.56 (42.44) in the OS, bracket; H2.79 (2.77); N22.13 (22.00).
Infrared measurement: IR (KBr), ν: 3110,1613,1541,1474,1453,1283,947,663.
(3) 5-chloro-salicylic aldehyde contracting-4-amino-5-sulfydryl-1 synthetic vanadyl title complex of the present invention: get 1mmol(0.255g), 2,4-triazole schiff base ligand is put into round-bottomed flask, adds the 20ml dehydrated alcohol, drips 1mmol(150 μ l) triethylamine, heated and stirred makes the part dissolving, add then and be dissolved with 1mmol(0.364g) the ethanol solution 10ml of methyl ethyl diketone vanadyl, stirring and refluxing is after 4 hours, cooling, filter, separate out yellow bulk crystals in the filtrate;
Determination of elemental analysis: C 9H 6ClN 4O 3SVC 6H 15Be theoretical value (%): C 41.28 (41.15) in the N, bracket; H 4.90 (4.83); N 16.13 (16.00).
The complex monocrystal structure
Under powerful microscope, picking rule, yellow transparent bulk-shaped monocrystal particle are tested with X-ray crystalline diffraction method, and are parsed the match crystal body structure with SHELXTL-NT5.10 version routine package.The crystalline structure of title complex such as accompanying drawing 1(are for making clear in structure, the deletion solvent molecule), about some other detailed information of crystal is listed in table 1 and table 2.In this title complex, the central atom vanadium is pentavalent, in the complex structure except the two keys of two VO, vanadium atom also with 5-chloro-salicylic aldehyde contracting 4-amino-5-sulfydryl-1,2, imine nitrogen atom in the 4-triazole schiff base ligand, the sulphur atom coordination of phenolic group Sauerstoffatom and triazolinthione forms the distortion tetragonal pyramid structure (VO of pentacoordinate 3NS).
Table 1 title complex [VO 2(C 9H 6ClN 4OS) C 6H 15N] structure cell and measuring parameter
Table 2 title complex [VO 2(C 9H 6ClN 4OS) C 6H 15N] the main bond distance of part
Figure BDA00003153010400042
With the bond angle data (°).
Embodiment 2 vanadyl title complexs of the present invention detect the PTP1B inhibition.
With vanadyl match crystal body and function dimethyl sulfoxide (DMSO) (DMSO) dissolving, be made into 10 -2The mother liquor of M is diluted to the solution (10 of different concns again with DMSO -4M, 10 -5M, 10 -6M, 10 -7M, 10 -8M, 10 -9M, 10 -10M).The mensuration that enzymic activity suppresses experiment is to be that reaction substrate is 7.20 MOPS buffer system [20mM morpholino propane sulfonic acid (MOPS) at pH with 2mM p-nitrophenyl disodic alkaliine (pNPP), 50mM NaCl] in carry out, experimental technique is: this experiment is to carry out in 96 orifice plates, add 83 μ l successively and contain enzyme buffer solution, the inhibitor of 10 μ l different concns gradients, pNPP with 2 μ l (0.1M) starts reaction, after placing about 15 minutes, add 5 μ l(2M again) the NaOH termination reaction, measure the degradation production of substrate at A by microplate reader 405Uv-absorbing intensity, the amount of the p-NP (pNP) that determine to generate, each sample is parallel to be done three times, deduction is blank simultaneously, uses Origin by title complex the inhibition curve of PTP1B to be calculated its IC 50Be worth, show the IC5 of title complex inhibition 0Value is got the repeatedly mean value of experiment.Calculate vanadium complex of the present invention as shown in Figure 2 to the IC of PTP1B 50Be 78nM.Illustrate that this vanadyl title complex has efficient inhibition to the PTP1B enzymic activity.
Embodiment 3 vanadyl title complexs of the present invention suppress determining of type to PTP1B.
With vanadyl match crystal body and function dimethyl sulfoxide (DMSO) (DMSO) dissolving, be made into 10 -2The mother liquor of M is diluted to the solution (200nM, 100nM, 50nM, 25nM) of different concns again with DMSO, the concentration of substrate pNPP is respectively 4mM, 2mM, 1mM, 0.5mM, 0.3mM, 0.2mM.The experiment reaction system is: 88 μ l contain enzyme (PTP1B) buffered soln and contain: 20mM morpholino propane sulfonic acid (MOPS), 50mM NaCl, the inhibitor of 10 μ l different concns gradients adds 2 μ l different concns pNPP and starts reaction in the reaction system, measure the changing value of photoabsorption at the 405nm place.Measure each inhibitor concentration respectively to the absorbance of each concentration of substrate, according to formula A=ε bc(b=1cm, ε=1.78 * 10 4A is the 405nm absorbancy, C is reactant concn mol/L) draw the speed of reaction ν under each inhibitor concentration, as shown in Figure 3, with concentration of substrate 1/[S reciprocal] be X-coordinate, be ordinate zou mapping with 1/ ν, obtain one group of straight line that vertical axis intercept is constant, the inhibition type of representing this title complex is the state of conflict inhibitor.As shown in Figure 4, according to the slope of Lineweaver-Burk equation straight line title complex concentration being mapped is straight line, and the intersection point of this straight line and X-axle is K for suppressing constant iBe 109nM.
Embodiment 4 vanadyl title complexs of the present invention and the interactional bonding constant of PTP1B and bonding ratio.
To 2ml, concentration is 5.9 * 10 with MOPS buffered soln dilution PTP1B mother liquor -7M, the setting excitation wavelength is 280nm, excites and launch slit width to be 5nm, experimental temperature is 310K, measures the PTP1B fluorescence intensity of solution, uses the titration of vanadyl title complex then, adds 4 μ l(1 * 10 at every turn -3M) solution reacted after 5 minutes, measured the fluorescence spectrum of 290～500nm scope.Accompanying drawing 5 shows the adding along with title complex, the PTP1B fluorescence intensity constantly reduces, and shows that vanadyl title complex and PTP1B bonding form mixture, according to Sterm one Volme fluorescent quenching equation, as shown in Figure 6, the bonding constant that calculates vanadyl title complex and PTP1B is 1.06 * 10 -6M -1, the bonding ratio is 0.095082, experimental result explanation, and vanadyl title complex and PTP1B are with the ratio stable bond of 1:1.

Claims (3)

1. vanadyl title complex, its structural formula is:
2. the preparation method of a kind of vanadyl title complex as claimed in claim 1 is characterized in that, comprises the steps:
(1) synthetic 4-amino-5-sulfydryl-1,2, the 4-triazole;
(2) synthetic 5-chloro-salicylic aldehyde contracting-4-amino-5-sulfydryl-1,2,4-triazole schiff base ligand: with equimolar amount 4-amino-5-sulfydryl-1,2,4-triazole and 5-chloro-salicylic aldehyde are dissolved in dehydrated alcohol respectively, stir down, 5-chloro-salicylic aldehyde's ethanol solution is added drop-wise to 4-amino-5-sulfydryl-1, in the ethanol solution of 2,4-triazole, drip the vitriol oil of 1-2 times of molar weight then, reflux after 4 hours, cooling is filtered, and solid is recrystallization in dehydrated alcohol;
(3) synthetic vanadyl title complex of the present invention: with methyl ethyl diketone vanadyl and the 5-chloro-salicylic aldehyde contracting-4-amino-5-sulfydryl-1 of equimolar amount, 2,4-triazole schiff base ligand is dissolved in dehydrated alcohol respectively, heated and stirred 5-chloro-salicylic aldehyde contracting-4-amino-5-sulfydryl-1,2, the ethanol solution of 4-triazole schiff base ligand, the triethylamine that drips equimolar amount makes the part dissolving, then, add the ethanol solution of methyl ethyl diketone vanadyl again, stirring and refluxing is after 4 hours, cooling, filter, collect mother liquor, separate out yellow bulk crystals.
3. a kind of vanadyl title complex as claimed in claim 1 is as the application of protein-tyrosine phosphatase 1B inhibitor.
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Cited By (8)

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CN104447852A (en) * 2014-11-17 2015-03-25 云南大学 Novel schiff base vanadium oxide compound as well as preparation method and application thereof
CN104530185A (en) * 2014-12-13 2015-04-22 中国海洋大学 Oxo-vanadium glutathione
CN104910212A (en) * 2015-05-07 2015-09-16 山西大学 Platinum schiff base complex and preparation method and application thereof
CN105037402A (en) * 2015-06-19 2015-11-11 山西大学 Schiff base and zinc coordination compound and preparation method and application thereof
CN106749393A (en) * 2017-01-09 2017-05-31 山西大学 Picoline hydrazonic acid derivative dioxygen vanadium（V）Complex and preparation method thereof
CN108558935A (en) * 2018-04-08 2018-09-21 广西师范大学 Vanadic anhydride crystalline material and its synthetic method based on the modification of tartaric acid chiral derivatives
CN110078639A (en) * 2019-05-24 2019-08-02 云南大学 A kind of schiff bases vanadium complex and the preparation method and application thereof
CN113105499A (en) * 2021-04-16 2021-07-13 河北民族师范学院 Schiff base vanadyl complex and preparation method thereof

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Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104447852A (en) * 2014-11-17 2015-03-25 云南大学 Novel schiff base vanadium oxide compound as well as preparation method and application thereof
CN104447852B (en) * 2014-11-17 2017-02-22 云南大学 Schiff base vanadium oxide compound as well as preparation method and application thereof
CN104530185A (en) * 2014-12-13 2015-04-22 中国海洋大学 Oxo-vanadium glutathione
CN104910212A (en) * 2015-05-07 2015-09-16 山西大学 Platinum schiff base complex and preparation method and application thereof
CN104910212B (en) * 2015-05-07 2017-08-11 山西大学 A kind of schiff bases platinum complex and its preparation method and application
CN105037402A (en) * 2015-06-19 2015-11-11 山西大学 Schiff base and zinc coordination compound and preparation method and application thereof
CN105037402B (en) * 2015-06-19 2017-05-17 山西大学 Schiff base and zinc coordination compound and preparation method and application thereof
CN106749393A (en) * 2017-01-09 2017-05-31 山西大学 Picoline hydrazonic acid derivative dioxygen vanadium（V）Complex and preparation method thereof
CN108558935A (en) * 2018-04-08 2018-09-21 广西师范大学 Vanadic anhydride crystalline material and its synthetic method based on the modification of tartaric acid chiral derivatives
CN108558935B (en) * 2018-04-08 2019-06-14 广西师范大学 Vanadic anhydride crystalline material and its synthetic method based on the modification of tartaric acid chiral derivatives
CN110078639A (en) * 2019-05-24 2019-08-02 云南大学 A kind of schiff bases vanadium complex and the preparation method and application thereof
CN113105499A (en) * 2021-04-16 2021-07-13 河北民族师范学院 Schiff base vanadyl complex and preparation method thereof

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