CN105300936A - Determination of yeast RNA (Ribonucleic Acid) by photoluminescence of ruthenium-based metal complex - Google Patents
Determination of yeast RNA (Ribonucleic Acid) by photoluminescence of ruthenium-based metal complex Download PDFInfo
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Abstract
The invention discloses a method for quantitatively determining the concentration of yeast RNA (Ribonucleic Acid) in a water solution with a fluorescent spectrometry by applying three types of ruthenium complexes. The method has high sensitivity.
Description
Technical field
The invention belongs to optochemical sensor field, relate to the synthetic method of three kinds of similar many pyridines ruthenium (II) complexs and sending out the application in the association areas such as photoluminescence mensuration yeast rna.
Background technology
A large amount of hereditary information is stored in the base of nucleic acid (DNA and RNA), it is the important composition material of biosome, they play key effect in the biosynthesizing of protein, closely bound up with vital movements such as the Growth and Reproduction growths of biology, be also the target spot of the medical diagnosis on disease such as cancer and AIDS and chemotherapeutic agent.Therefore research preparation can specific binding the molecular probe measuring nucleic acid to the sound development of the progress and the whole mankind that promote life science and medical science all tool be of great significance [Campisi, D.; Morii, T.; Barton, J.K.Biochemistry1994,33,4130.].In the past few decades, various metal complex is the focus in nucleic acid probe research and development field, especially many pyridines ruthenium (II) complex, because it has abundant optical physics, photochemistry and redox property, and the interaction between nucleic acid obtains extensive and deep research.Nineteen ninety, the people such as Barton report [Ru (bpy)
2(dppz)]
2+(bpy=2,2 '-dipyridine, dppz=bis-pyrido [3,2-a:2 ', 3 '-c] azophenlyene) and [Ru (phen)
2(dppz)]
2+(phen=1,10-o-phenanthroline) can be used as molecular light switch [Pyle, the A.M. of DNA in aqueous; Morii, T.; Barton, J.K.J.Am.Chem.Soc.1990,112,9432. (b) Sitlani, A.; Long, E.C.; Pyle, A.M.; Barton, J.K.J.Am.Chem.Soc.1992,114.2303.].On this basis, many researchers are devoted to research and develop the more excellent complex of photoswitch performance.First modification is carried out to the part dppz of above-mentioned two kinds of complexs and obtain derivant, but photoswitch performance there is no the improvement of expection.In recent years, researcher is by diversion on the complex containing dpq (dpq=bis-pyrido [3,2-d:2 ', 3 '-f]-quinoxaline) part, and this ligand structure is similar to dppz, but conjugacy is not so good as dppz.Containing the complex [Ru (phen) of dpq derived ligand
2(dcdpq)]
2+(dcdpq=6,7-dicyano two pyrido [3,2-d:2 ' 3 '-f] quinoxaline) and [Ru (phen) (dcdpq)
2]
2+show the behavior of DNA photoswitch, be respectively 16 and 8 with the Fluorescence Increasing factor after DNA bonding, complex [Ru (phen)
2(dpqa)]
2+after (dpqa=2-(N-amyl group amide group) two pyridos [3,2-f:2 ', 3 '-h]-quinoxaline) and DNA bonding, fluorescence significantly strengthens [Ambroise, A.; Maiya, B.G.Inorg.Chem.2000,39,4264.O ' Donoghue, K.A.; Penedo, J.C.; Kelly, J.M.; Kruger, P.E.DaltonTrans.2005,1123.O ' Donoghue, K.A.; Kelly, J.M.; Kruger, P.E.DaltonTrans.2004,13.Daleney, S.; Pascaly, M.; Bhattacharya, P.K.; Han, K.; Barton, J.K.Inorg.Chem.2002,41,1966.Collins, J.G.; Sleeman, A.D.; Aldrich-Wright, J.R.; Greguric, I.; Hambley, T.W.Inorg.Chem.1998,37,3133.Greguric, I.; Aldrich-Wright, J.R.; Norden, B.J.Am.Chem.Soc.1997,119,3621.].Our seminar once reported dpq with carboxyl as the complex [Ru (phen) of part
2(Hcdpq)]
2+(Hcdpq=2-carboxyl two pyrido [3,2-d:2 ', 3 '-f]-quinoxaline) DNA photoswitch character, and prove this complex can by DNA and yeast rna difference come, because before and after it and RNA bonding, fluorescence intensity does not almost have significant change [Zhang, A.G.; Zhang, Y.Z.; Duan, Z.M.; Wang, K.Z.; Wei, H.B.; Bian, Z.Q.; Huang, C.H.Inorg.Chem.2011,50,6425-6436.].Up to the present, existing many DNA molecular photoswitches based on ruthenium (II) complex, but the interactional research of ruthenium (II) between complex and RNA mainly concentrates on the research such as bond characters, bonding pattern aspect, rarely has the molecular light switch of RNA to be in the news.Our seminar also once reported three complex [Ru (bpy) respectively using the derivant of dpq as part
2(bipp)]
2+, [Ru (bpy)
2(bopp)]
2+[Ru (bpy)
2(btpp)]
2+(benzimidazolyl, benzoxazolyl and benzothiazolyl are connected on dpq and obtain by part bipp, bopp and btpp respectively) shows excellent DNA molecular photoswitch character [Han, M.J.; Duan, Z.M.; Hao, Q.; Wang, K.Z.J.Phys.Chem.C2007,111,16577-16585.], in order to advance the research of RNA molecule photoswitch, we further study these three kinds of complexs in aqueous systems with the interaction of yeast rna, result shows, obvious Enhancement of Fluorescence has all been there is after these three kinds of complexs and yeast rna effect, can be used as the RNA molecule photoswitch that a class is new, realized the detection to yeast rna by photoluminescence fast, easily, there is very important using value in the mensuration of yeast rna.
Summary of the invention
The object of the invention is ruthenium (II) complex [Ru (bpy) utilizing three kinds of structures similar
2(bipp)] (ClO
4)
2, [Ru (bpy)
2(bopp)] (ClO
4)
2[Ru (bpy)
2(btpp)] (ClO
4)
2under yeast rna exists, the character of luminescence enhancement, realizes quantitative measurement by photoluminescence to the yeast rna in the water buffer system under physiological pH.
Technical scheme of the present invention is as follows: first, synthesizes main part bipp, bopp and btpp respectively; Then make main part respectively with [Ru (bpy)
2cl
2] 2H
2o reacts, and obtains complex [Ru (bpy)
2(bipp)] (ClO
4)
2, [Ru (bpy)
2(bopp)] (ClO
4)
2[Ru (bpy)
2(btpp)] (ClO
4)
2, and purified by column chromatography methods; Finally, measure complex fluorescence emission spectrum change of generation along with the concentration of yeast rna increases in Tris-HCl buffer solution, in the scope of fluorescence intensity with RNA concentration linear increase, make working curve, thus reached the object quantitatively detecting yeast rna by the photoluminescence of complex.
Compared with prior art, advantage of the present invention is:
Ruthenium complex [Ru (bpy) prepared by the present invention
2(bipp)] (ClO
4)
2, [Ru (bpy)
2(bopp)] (ClO
4)
2[Ru (bpy)
2(btpp)] (ClO
4)
2in water buffer solution, luminescence is very weak or not luminous, and after adding yeast rna, complex luminescence all significantly strengthens, and three kinds of complexs are that the molecule light of excellent yeast rna opens the light, and can realize the quantitative detection to yeast rna fast, easily by photoluminescence means.Can carry out in the aqueous systems being in physiological pH the detection of yeast rna, the concentration of the yeast rna that can detect is very low, [Ru (bpy)
2(bipp)] (ClO
4)
2, [Ru (bpy)
2(bopp)] (ClO
4)
2[Ru (bpy)
2(btpp)] (ClO
4)
20.06 μM is respectively to the detection limit concentration of yeast rna, 0.3 μM and 0.6 μM.Therefore, to the mensuration of yeast rna, there is important using value in three kinds of ruthenium (II) complexs aqueous systems at physiological ph in the present invention.
Accompanying drawing explanation
Fig. 1 is complex [Ru (bpy)
2(bipp)] (ClO
4)
2, [Ru (bpy)
2(bopp)] (ClO
4)
2[Ru (bpy)
2(btpp)] (ClO
4)
2structural representation.
Fig. 2 is complex [Ru (bpy)
2(bipp)] (ClO
4)
2the Tris-HCl solution (5mM, pH=7.1) of (4.6 μMs) is emission spectrum (λ within the scope of 0-160 μM at yeast RNA concentration
ex=450nm), illustration is the working curve of the mensuration yeast rna (0-17 μM) according to emission spectra data drafting.
Fig. 3 is complex [Ru (bpy)
2(bopp)] (ClO
4)
2the Tris-HCl solution (5mM, pH=7.1) of (6 μMs) is emission spectrum (λ within the scope of 0-160 μM at yeast RNA concentration
ex=450nm), illustration is the working curve of the mensuration yeast rna (0-40 μM) according to emission spectra data drafting.
Fig. 4 is complex [Ru (bpy)
2(btpp)] (ClO
4)
2the Tris-HCl solution (5mM, pH=7.1) of (6 μMs) is emission spectrum (λ within the scope of 0-150 μM at yeast RNA concentration
ex=450nm), illustration is the working curve of the mensuration yeast rna (0-22 μM) according to emission spectra data drafting.
Embodiment
Embodiment 1: complex [Ru (bpy)
2(bipp)] (ClO
4)
2, [Ru (bpy)
2(bopp)] (ClO
4)
2[Ru (bpy)
2(btpp)] (ClO
4)
2synthesis
Complex [Ru (bpy)
2(bipp)] (ClO
4)
2, [Ru (bpy)
2(bopp)] (ClO
4)
2[Ru (bpy)
2(btpp)] (ClO
4)
2the method [Han, the M.J. that have reported according to this seminar; Duan, Z.M.; Hao, Q.; Wang, K.Z.J.Phys.Chem.C2007,111,16577-16585.] synthesis.
Part bipp, bopp and btpp respectively by pyrazine [2,3-f] [1,10] o-phenanthroline-2-carboxylic acid and o-phenylenediamine, Ortho-Aminophenol and 2-aminothiophenol by 1: 1 mol ratio in polyphosphoric acid, be heated to 200 DEG C condensation reactions occur obtain.After reaction end is cooled to room temperature, potpourri is under agitation poured in 400mL cold water, then uses strong aqua regulation system pH to 7.The precipitation that suction filtration obtains, obtains thick product, then in methyl alcohol twice, recrystallization.Bipp, bopp, btpp productive rate is respectively 55%, 25% and 58%.The hydrogen nuclear magnetic resonance modal data of bipp is:
1hNMR (500Hz, DMSO-d
6): δ 13.52 (s, 1H), 9.82 (s, 1H), 9.81 (d, 1H), (9.35 d, J=8.0Hz, 1H), 9.22 (d, J=3.3Hz, 1H), 9.19 (d, J=3.1Hz, 1H), 7.96 (dd, J
1=7.7Hz, J
2=4.2Hz, 1H), 7.88 (dd, J
1=8.0Hz, J
2=4.3Hz, 1H), 7.83 (d, J=7.9Hz, 1H), 7.69 (d, J=7.7Hz, 1H), 7.38 (t, J=7.0Hz, 1H), 7.31 (t, J=7.1Hz, 1H).Bopp and btpp solubleness in common organic solvents is all very poor, so do not carry out hydrogen nuclear magnetic resonance spectrum sign.Complex [Ru (bpy)
2(bipp)] (ClO
4)
2, [Ru (bpy)
2(bopp)] (ClO
4)
2[Ru (bpy)
2(btpp)] (ClO
4)
2building-up process identical.With complex [Ru (bpy)
2(bopp)] (ClO
4)
2the example that synthesizes be described.By [Ru (bpy)
2cl
2] 2H
2o (1.1mmol) and bopp (1.0mmol) is scattered in the mixed solution of 50mL ethanol/water (V/V=4: 1), in N
2reflux under protection 6h.After reaction terminates, revolve and steam the most of solvent of removing, then in remaining liquid, dropwise add the saturated NaClO of excessive 4 times
4solution, obtains red perchlorate precipitation.Thick product uses acetonitrile/water/saturated KNO on a silica gel column
3the mixed solution of solution (V/V/V=60: 6: 1) carries out pillar layer separation purification as developping agent, adds saturated NaClO in the most backward reaction mixture obtained
4solution separates out precipitation, and suction filtration gained precipitates, and vacuum drying obtains product.
[Ru (bpy)
2(bipp)] (ClO
4)
23H
2the productive rate of O is 53%.Ultimate analysis: [C
41h
28n
10cl
2o
8ru3H
2o (F.W.=1014.78)] calculated value: C, 48.53; H, 3.377; N13.81%; Measured value: C, 48.93; H, 3.499; N, 13.72%.Hydrogen nuclear magnetic resonance spectrum:
1hNMR (500MHz, Me
2sO-d
6): δ 13.75 (brs, 1H), 10.11 (s, 1H), 10.01 (d, J=8.2Hz, 1H), 9.58 (d, J=8.2Hz, 1H), 8.91 (d, J=8.2Hz, 2H), 8.87 (d, J=8.2Hz, 2H), 8.29 (d, J=5.3Hz, 2H), 8.26 (td, J
1=8.0Hz, J
2=1.4Hz, 2H), 8.14 (m, 3H), 8.05 (dd, J
1=5.4Hz, J
2=4.1Hz, 1H), 7.85 (t, J=5.0Hz, 2H), 7.75 (m, 4H), 7.62 (t, J=6.0Hz, 2H), 7.38 (m, 4H).Infrared spectrum (KBr, cm
-1): 3430,3073,1603,1557,1465,1445,1423,1399,1370,1317,1090,766,729,623.MALDI-TOF mass spectrum: m/z778.82 ([M-2ClO
4 -+ H
2o-H
+]
+), 760.80 ([M-2ClO
4 --H
+]
+), 605.04 ([M-2ClO
4 --bpy-H
+]
+).Uv-visible absorption spectra in water: λ/nm (ε × 10
4m
-1cm
-1): 285 (6.7); 370 (3.2); 449 (1.7).
[Ru (bpy)
2(bopp)] (ClO
4)
2productive rate be 43%.Ultimate analysis: [C
41h
27n
9cl
2o
9ru (F.W.=961.72)]: calculated value: C, 49.36; H, 3.132; N, 12.63%; Measured value: C, 49.06; H, 3.435; N, 12.61%.Hydrogen nuclear magnetic resonance spectrum:
1hNMR (500MHz, Me
2sO-d
6): δ 10.16 (s, 1H), 9.66 (d, J=8.0Hz, 1H), 9.61 (d, J=8.1Hz, 1H), 8.89 (dd, J
1=17.0Hz, J
2=8.2Hz, 4H), 8.33 (m, 2H), 8.25 (t, J=7.9Hz, 2H), 8.15 (m, 2H), 8.06 (m, 4H), 7.85 (d, J=5.5Hz, 2H), 7.74 (m, 2H), 7.62 (m, 4H), 7.38 (t, J=6.6Hz, 2H).Infrared spectrum (KBr, cm
-1): 3076,1603,1465,1405,1375,1089,762,730,622.MALDI-TOF mass spectrum: m/z862.04 ([M-ClO
4 -]
+), 763.08 ([M-2ClO
4 -]
2+).Uv-visible absorption spectra in water: λ/nm (ε × 10
4m
-1cm
-1): 284 (7.9); 361 (3.6); 447 (1.8).
[Ru (bpy)
2(btpp)] (ClO
4)
23H
2the productive rate of O is 87%.Ultimate analysis: [C
41h
27n
9cl
2o
8ruS3H
2o (F.W.=1031.82)]: C, 47.73; H, 3.220; N, 12.22%.Measured value: C, 47.97; H, 3.563; N, 12.06%.Hydrogen nuclear magnetic resonance spectrum:
1hNMR (500MHz, Me
2sO-d
6): δ 10.13 (s, 1H), 9.59 (t, J=7.1Hz, 2H), 8.90 (d, J=8.0Hz, 2H), 8.87 (dd, J
1=8.1Hz, J
2=3.3Hz, 2H), 8.30 (m, 4H), 8.24 (t, J=8.0Hz, 2H), 8.13 (m, 3H), 8.06 (dd, J
1=8.2Hz, J
2=5.4Hz, 1H), 7.86 (br, 2H), 7.76 (d, J=5.6Hz, 1H), 7.72 (d, J=5.6Hz, 1H), 7.68 (m, 4H), 7.38 (m, 2H).Infrared spectrum (KBr, cm
-1): 3446,1603,1446,1384,1087,764,625.MALDI-TOF mass spectrum: m/z878.06 ([M-ClO
4 -]
+), 779.11 ([M-2ClO
4 -]
2+).Uv-visible absorption spectra in water: λ/nm (ε × 10
4m
-1cm
-1): 284 (7.8); 368 (3.4); 450 (1.8).
Embodiment 2: complex [Ru (bpy)
2(bipp)] (ClO
4)
2, [Ru (bpy)
2(bopp)] (ClO
4)
2[Ru (bpy)
2(btpp)] (ClO
4)
2the drafting of photoluminescence determination yeast rna and working curve
Fluorescence emission spectrum measures on ShimadzuRF-5301PC fluorospectrophotometer, and excitation wavelength is 450nm.
To [the Ru (bpy) that concentration is 4.6 μMs
2(bipp)] (ClO
4)
2tris-HCl (5mM, pH=7.1) solution in constantly add yeast rna solution, measure the change of the increase emission spectrum along with yeast RNA concentration, until the emission spectrum of complex no longer changes.When yeast RNA concentration reaches 160 μMs, the emission spectrum of complex no longer changes, the increase of the intensity RNA concentration of the emission peak at 623nm place and increasing gradually, and is attended by the blue shift of 9nm.Be wherein within the scope of 0-17 μM at yeast RNA concentration, the fluorescence intensity of complex at 623nm place is with the increase linear increase of RNA concentration, with fluorescence intensity I, RNA concentration is mapped, can obtain the working curve of the mensuration yeast rna as shown in illustration in Fig. 2, the equation of its correspondence is: I=16.67387+5.52749 [RNA].Utilize the quantitative measurement that this working curve can realize yeast rna.
To [the Ru (bpy) that concentration is 6 μMs
2(bopp)] (ClO
4)
2tris-HCl (5mM, pH=7.1) solution in constantly add yeast rna solution, measure the change of the increase emission spectrum along with yeast RNA concentration, until the emission spectrum of complex no longer changes.When yeast RNA concentration reaches 160 μMs, the emission spectrum of complex no longer changes, the increase of the intensity RNA concentration of the emission peak at 634nm place and increasing gradually, and is attended by the blue shift of 4nm.Be wherein within the scope of 0-40 μM at yeast RNA concentration, the fluorescence intensity of complex at 634nm place is with the increase linear increase of RNA concentration, with fluorescence intensity I, RNA concentration is mapped, can obtain the working curve of the mensuration yeast rna as shown in illustration in Fig. 3, the equation of its correspondence is: I=35.05116+8.66484 [RNA].Utilize the quantitative measurement that this working curve can realize yeast rna.
To [the Ru (bpy) that concentration is 6 μMs
2(btpp)] (ClO
4)
2tris-HCl (5mM, pH=7.1) solution in constantly add yeast rna solution, measure the change of the increase emission spectrum along with yeast RNA concentration, until the emission spectrum of complex no longer changes.When yeast RNA concentration reaches 150 μMs, the emission spectrum of complex no longer changes, the increase of the intensity RNA concentration of the emission peak at 627nm place and increasing gradually, and is attended by the blue shift of 4nm.Be wherein within the scope of 0-22 μM at yeast RNA concentration, the fluorescence intensity of complex at 627nm place is with the increase linear increase of RNA concentration, with fluorescence intensity I, RNA concentration is mapped, can obtain the working curve of the mensuration yeast rna as shown in illustration in Fig. 4, the equation of its correspondence is: I=29.76276+4.68273 [RNA].Utilize the quantitative measurement that this working curve can realize yeast rna.
Embodiment 3: complex [Ru (bpy)
2(bipp)] (ClO
4)
2, [Ru (bpy)
2(bopp)] (ClO
4)
2[Ru (bpy)
2(btpp)] (ClO
4)
2measure the detection limit of yeast rna
Fluorescence emission spectrum measures on ShimadzuRF-5301PC fluorospectrophotometer, and excitation wavelength is 450nm.
Get 6 parts of [Ru (bpy)
2(bipp)] (ClO
4)
2tris-HCl (5mM, the pH=7.1) solution of (4.6 μMs), measures the emission spectrum of solution respectively, obtains 6 parallel determinations.From the emission spectrum at every turn recorded, draw the luminous intensity of complex solution at 623nm, be respectively 8.138,8.039,8.291,8.275,8.141,8.342, calculate the standard deviation of 6 luminous intensity values
1=0.1064.[Ru (bpy)
2(bipp)] (ClO
4)
2measure the slope K of the working curve of yeast rna
1=5.52749 μMs
-1, utilize 3 σ/K to draw to detect and be limited to 0.06 μM.
Get 6 parts of [Ru (bpy)
2(bopp)] (ClO
4)
2tris-HCl (5mM, the pH=7.1) solution of (6 μMs), measures the emission spectrum of solution respectively, obtains 6 parallel determinations.From the emission spectrum at every turn recorded, draw the luminous intensity of complex solution at 634nm, be respectively 16.642,17.745,18.611,16.552,17.894,16.454, calculate the standard deviation of 6 luminous intensity values
2=0.8682.[Ru (bpy)
2(bopp)] (ClO
4)
2measure the slope K of the working curve of yeast rna
2=8.66484 μMs
-1, utilize 3 σ/K to draw to detect and be limited to 0.3 μM.
Get 6 parts of [Ru (bpy)
2(bopp)] (ClO
4)
2tris-HCl (5mM, the pH=7.1) solution of (6 μMs), measures the emission spectrum of solution respectively, obtains 6 parallel determinations.From the emission spectrum at every turn recorded, draw the luminous intensity of complex solution at 627nm, be respectively 38.898,37.888,38.242,36.389,37.138,38.577, calculate the standard deviation of 6 luminous intensity values
3=0.9283.[Ru (bpy)
2(bopp)] (ClO
4)
2measure the slope K of the working curve of yeast rna
3=4.68273 μMs
-1, utilize 3 σ/K to draw to detect and be limited to 0.6 μM.
Claims (4)
1. ruthenium complex [Ru (bpy)
2(bipp)] X
2, [Ru (bpy)
2(bopp)] X
2[Ru (bpy)
2(btpp)] X
2measure the purposes of yeast rna in aqueous solution, wherein bpy is 2,2'-dipyridine, and benzimidazolyl, benzoxazolyl and benzothiazolyl are connected on two pyridos [3,2-d:2 ', 3 '-f]-quinoxaline to obtain by bipp, bopp and btpp; X is counter ion counterionsl gegenions.
2. purposes as claimed in claim 1, is characterized in that, described X is negative monovalent ion, is selected from Cl
-, PF
6 -, ClO
4 -, NO
3 -, BF
4 -and CF
3sO
3 -in one.
3. purposes as claimed in claim 1, is characterized in that, complex one of 1a, 1b and 1c that the structure of described ruthenium complex is shown below:
4. the purposes as described in as arbitrary in claims 1 to 3, is characterized in that, utilizes described ruthenium complex to measure the content of yeast rna in aqueous solution, comprises the following steps:
1) in a series of aqueous solution of known yeast RNA concentration, add described ruthenium complex, measured the fluorescence intensity of system by excited by visible light, obtain the typical curve of fluorescence intensity relative to yeast RNA concentration;
2) in containing the aqueous solution of described ruthenium complex, add a certain amount of yeast rna solution to be measured, measure its fluorescence intensity by excited by visible light;
3) according to step 2) value of luminous intensity that records, by step 1) typical curve that obtains determines the concentration of yeast rna in solution to be measured.
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Cited By (2)
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|---|---|---|---|---|
| CN106770101A (en) * | 2016-12-05 | 2017-05-31 | 北京师范大学 | Application of the ruthenium complex in DNA and the difunctional phosphorescence sensing of acid pH |
| CN112067593A (en) * | 2020-09-16 | 2020-12-11 | 江西农业大学 | Preparation and detection method of Tb-MOF fluorescent material for rapidly detecting thiabendazole in navel orange |
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| CN112067593A (en) * | 2020-09-16 | 2020-12-11 | 江西农业大学 | Preparation and detection method of Tb-MOF fluorescent material for rapidly detecting thiabendazole in navel orange |
| CN112067593B (en) * | 2020-09-16 | 2021-07-13 | 江西农业大学 | Preparation and detection method of Tb-MOF fluorescent material for rapidly detecting thiabendazole in navel orange |
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