CN113390951A - Application of AgOTf as reaction matrix in detection of bromine-containing compound in MALDI mass spectrometry - Google Patents
Application of AgOTf as reaction matrix in detection of bromine-containing compound in MALDI mass spectrometry Download PDFInfo
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Abstract
The invention discloses application of adding silver trifluoromethanesulfonate (AgOTf) as a novel reaction type matrix and combining with an auxiliary matrix (AgOTf/auxiliary matrix) in high-throughput qualitative and quantitative detection of a bromine-containing compound. In MALDI mass spectrometry, a target plate reaction strategy based on AgOTf/auxiliary matrix can realize high-throughput qualitative and quantitative analysis of bromine-containing compounds. AgOTf has silver group, and can be easily reacted with halogen atom to generate [ AgBr + Br ] as reaction type matrix]‑、[2AgBr+Br]‑、[AgOTf+Br]‑And [2AgOTf + Br]‑A series of compounds. An auxiliary matrix for assisting the ionization of the compound to be generated. The AgOTf/auxiliary matrix is suitable for detecting organic and inorganic bromine-containing compounds as the matrix.
Description
Technical Field
The invention relates to the field of biochemical analysis of bromine-containing compounds, in particular to application of AgOTf as a reaction matrix in detection of bromine-containing compounds in MALDI mass spectrometry.
Background
Bromine-containing compounds are widely present in the environment and have a significant impact on human health. Bromine is an essential element of the human body and plays an important role in many life processes. The lack or excessive intake of bromine is not good for human health. Bromine-containing compounds in the atmosphere can affect earth reflectivity and global climate and participate in various atmospheric photochemical reactions, destroying the ozone layer. Bromine in the wastewater can react with soluble organic matters in the disinfection process to form bromine-containing disinfection byproducts which are more harmful than chlorine-containing disinfection byproducts. The establishment of a high-flux qualitative and quantitative detection method has important significance in environmental, food and toxicological analysis taking bromine-containing compounds as research objects.
Mass spectrometry is one of the important tools for detecting substances. For the determination of bromine, the currently adopted method is an Inductively Coupled Plasma Mass Spectrometry (ICP-MS) method, which has high sensitivity but slow analysis speed, and a single sample needs several minutes, so that high-throughput analysis is difficult to realize. Matrix-Assisted Laser Desorption/ionization mass Spectrometry (MALDI-MS) has the advantages of simple operation, less sample consumption, high analysis speed and the like, can realize high-throughput detection, and is widely applied to the detection of organic compounds. However, many bromine-containing organic compounds are poorly ionized in MALDI, which greatly limits the sensitivity of MALDI techniques to such species. In addition, there is currently no MALDI matrix suitable for analysis of inorganic bromine-containing compounds, which limits the scope of MALDI techniques to some extent. Therefore, the existing detection method for the bromine-containing compound still has defects and needs to be improved.
In view of the above problems, designing and developing a MALDI target plate reaction strategy based on a novel combined matrix is of great value for realizing high-throughput qualitative and quantitative detection of bromine-containing compounds.
Disclosure of Invention
The invention provides application of silver trifluoromethanesulfonate (AgOTf) as a novel reaction type matrix and auxiliary matrix for combination (AgOTf/auxiliary matrix) to detection of bromine-containing compounds. In MALDI mass spectrometry, a target plate reaction strategy based on AgOTf/auxiliary matrix can realize high-throughput qualitative and quantitative analysis of bromine-containing compounds. AgOTf has silver group, and can be easily reacted with halogen atom to generate [ AgBr + Br ] as reaction type matrix]-、[2AgBr+Br]-、[AgOTf+Br]-And [2AgOTf + Br]-A series of compounds. Auxiliary matrix, can be supplementedAiding in the ionization of the product compound. The AgOTf/common matrix is suitable for detecting organic and inorganic bromine-containing compounds as a combined matrix.
The AgOTf is applied to the detection of bromine-containing compounds in MALDI mass spectrometry. The AgOTf and auxiliary matrix combined matrix is applied to the detection of bromine-containing compounds in MALDI mass spectrometry. AgOTf is a reactive matrix, has silver groups, and can react with bromine in bromine-containing compounds. And the auxiliary matrix can obviously improve the signal intensity of a series of mass spectrum peaks generated. The auxiliary matrix is at least one of Sinapic Acid (SA), 2, 5-dihydroxybenzoic acid (DHB), alpha-cyano-4-hydroxycinnamic acid (CHCA), 1, 5-Naphthalenediamine (NDA), 3-aminoquinoline (3-AQ), naphthalene ethylenediamine hydrochloride (NEDC), trans-2- [3- (4-tert-butylphenyl) -2-methyl-2-propylene ] malononitrile (DCTB), 2,4, 6-Trihydroxyacetophenone (THAP) and 3-hydroxy-2-picolinic acid (HPA), namely one or more (including two). Further preferably, the auxiliary substrate is Sinapic Acid (SA).
The application of the AgOTf and common matrix combined matrix in the detection of bromine-containing compounds in MALDI mass spectrometry specifically comprises the following steps:
preparing a sample by using AgOTf, an auxiliary matrix and a solution of a bromine-containing compound to be detected, and spotting the prepared sample on a polishing target spot sample hole to obtain a spotted target plate; and placing the spotted target plate to a mixed sample spot for natural drying, and performing MALDI mass spectrometry.
The detection of the bromine-containing compound is high-flux qualitative and quantitative detection of the bromine-containing compound, and the application specifically comprises the following steps:
1. reagent preparation
Preparing an auxiliary matrix methanol solution; preparing an AgOTf methanol solution, wherein AgOTf is silver trifluoromethanesulfonate; preparing a methanol solution of the bromine-containing compound to be detected.
2. Spotting is carried out
And (3) preparing samples by using a dry drop method by respectively taking methanol solution, AgOTf methanol solution and auxiliary matrix methanol solution of bromine-containing compounds to be detected with equal volumes, and spotting the prepared samples on the polished target spot sample holes to obtain the spotted target plate.
3. Target plate reaction
And placing the sample-spotted target plate at normal temperature and normal pressure to a mixed sample spot for natural drying, and performing MALDI mass spectrometry.
In the step 1, methanol for dissolving a matrix and a sample is an agricultural residue solvent;
the concentration of AgOTf in the AgOTf methanol solution is 5-25 mg/mL;
the concentration of the auxiliary matrix in the auxiliary matrix methanol solution is 5-25 mg/mL;
in the step 2, the sample preparation volume of the methanol solution containing the bromine compound to be detected is 0.5-2 mu L;
the sample preparation volume of the AgOTf solution is 0.5-2 mu L;
the sample preparation volume of the SA solution is 0.5-2 mu L;
the sample application volume of the prepared sample solution is 0.5-2 mu L;
in step 3, the spotted target plate is placed at room temperature to be naturally dried;
the ion source detection mode adopted by the MALDI mass spectrometry is a negative ion mode;
the ion detector detection mode adopted by the MALDI mass spectrometry is a reflection mode or a linear mode.
The MALDI mass spectrum refers to matrix assisted laser desorption ionization time-of-flight mass spectrum (MALDI-TOF-MS), and is referred to as MALDI mass spectrum for short. MALDI operates on the principle of laser irradiation of a sample to form a co-crystal with a matrix, which absorbs energy from the laser and transfers it to the sample molecules to ionize them. MALDI is a soft ionization technique.
The 'reaction type matrix' in the invention is used as a conventional matrix to assist the ionization of a bromine-containing compound, and can quickly react with bromine of the bromine-containing compound to form a series of compounds in a combined manner, so that the detection sensitivity is improved.
The target plate reaction strategy in the invention means that sample application and reaction of a sample on a target plate are synchronously carried out, so that the operation steps are greatly simplified, and the high-throughput characteristic of MALDI is compatible.
The bromine-containing compounds referred to in the present invention are organic and inorganic compounds having a bromine atom.
Compared with the prior art, the invention has the following advantages:
1.AgOTf has silver group, and can easily react with bromine atom to generate [ AgBr + Br ] as reaction type matrix]-、[2AgBr+Br]-、[AgOTf+Br]-And [2AgOTf + Br]-A series of compounds. An auxiliary matrix for assisting the ionization of the compound to be generated. The sample is pretreated in the sample application process, and the method is suitable for target plate reaction to carry out high-throughput detection on bromine-containing compounds.
2. Due to multiple effects of oxidation, catalysis, promotion of ionization and the like, the AgOTf/auxiliary matrix combined matrix has excellent matrix characteristics, can obviously improve the detection sensitivity of bromine-containing compounds, and is suitable for detection of different types of bromine-containing compounds.
3. The AgOTf/auxiliary matrix combined matrix is suitable for qualitative and quantitative detection of bromine-containing compounds, the bromine-containing compounds have good linear relation in the range of 3.33-500 mu g/mL, and R is2＞0.98。
Drawings
FIG. 1 is a MALDI mass spectrum for the detection of tetrabromobisphenol A (TBBPA), tris (2, 3-dibromopropyl) isocyanurate (TBC) and tetraethylammonium bromide (TEAB); FIG. 1A is a MALDI mass spectrum of AgTFA/SA as a combined matrix for detection of TBBPA; FIG. 1B is a MALDI mass spectrum of the combination matrix AgOTf/SA for detecting TBBPA; FIG. 1C is a MALDI mass spectrum of AgTFA/SA as a combined matrix for detection of TBC; FIG. 1D is a MALDI mass spectrum of AgOTf/SA as a combined matrix for detection of TBC; FIG. 1E is a MALDI mass spectrum of AgTFA/SA as a combined matrix for detection of TEAB; FIG. 1F is a MALDI mass spectrum of AgOTf/SA as a combined matrix for detection of TEAB.
FIG. 2 is a graph of the effect of AgOTf in combination with different co-substrates on the signal-to-noise ratio of TBBPA, TBC and TEAB at a mass-to-charge ratio of 592.63 Da.
FIG. 3 is a mass spectrum graph showing the mass to charge ratio of detecting bronopol, 5, 7-dibromo-8-hydroxyquinoline, benzbromarone, bromoindigo, dibromohydantoin, tetrabromobisphenol A bis (2, 3-dibromoallyl) ether, tribromophenol, tris (tribromophenoxy) triazine and LiBr at 592.63 Da; FIG. 3A is a MALDI mass spectrum of AgOTf/SA as a combined matrix at a mass to charge ratio of 592.63 Da; FIG. 3B is a MALDI mass spectrum of detecting bronopol with AgOTf/SA as a combined matrix; FIG. 3C is a MALDI mass spectrum of AgOTf/SA as a combined matrix for detecting 5, 7-dibromo-8-hydroxyquinoline; FIG. 3D is a MALDI mass spectrum of the detection of benzbromarone with AgOTf/SA as a combined matrix; FIG. 3E is a MALDI mass spectrum of AgOTf/SA as a combined matrix for detecting bromoindigo; FIG. 3F is a MALDI mass spectrum of AgOTf/SA as a combined matrix for detecting dibromohydantoin; FIG. 3G is a MALDI mass spectrum of detecting tetrabromobisphenol A bis (2, 3-dibromoallyl) ether with AgOTf/SA as a combined matrix; FIG. 3H is a MALDI mass spectrum of AgOTf/SA as a combined matrix for detecting tris (tribromophenoxy) triazine; FIG. 3I is a MALDI mass spectrum of tribromophenol detected with AgOTf/SA as a combined matrix; FIG. 3J is a MALDI mass spectrum of AgOTf/SA as a combined matrix for detecting LiBr.
FIG. 4 is a linear range of mass to charge ratio of 266.74Da for LiBr detection using AgOTf/SA as the matrix.
FIG. 5 shows the detection of Br in tap water using AgOTf/SA as the matrix-MALDI mass spectrum of (a).
Detailed Description
The present invention will be further illustrated by the following examples, but the present invention is not limited to the following examples.
The samples, reagents and the like used in the following examples are commercially available unless otherwise specified. The present invention will be described below with reference to specific examples, but the present invention is not limited thereto.
The specific model of matrix-assisted laser desorption ionization time-of-flight mass spectrometer used in the following examples is UlraflexTMMALDI-TOF/TOFMS (BrukerDaltonic, Germany), laser using a 355nm wavelength Nd: YAG laser. Detecting the bromine-containing compound in a negative ion mode; bromine-containing compounds are detected in reflectance mode. Negative ion reflection mode parameters: acceleration voltage, 20.00 kV; delayed extraction voltage, 17.75 kV; delay pull-out time, 100 ns; reflector voltage 1, 21.10 kV; reflector voltage 2, 10.7 kV; lens voltage, 8.50 kV; frequency, 2000 Hz. The target plate used was a 384polished plate (MTP 384polish Steel) and the mass spectrometric data analysis was performed using BrukerFlexanalysis 3.4 software.
The following shorthand or foreign language terms are used throughout this invention:
AgTFA silver trifluoroacetate
Silver AgOTf trifluoromethanesulfonate;
HPA 3-hydroxy-2-pyridinecarboxylic acid;
SA sinapic acid;
DHB2, 5-dihydroxybenzoic acid;
CHCA α -cyano-4-hydroxycinnamic acid;
NDA1, 5-naphthalenediamine;
3-AQ 3-aminoquinoline;
NEDC naphthylethylenediamine hydrochloride salt;
DCTB trans-2- [3- (4-tert-butylphenyl) -2-methyl-2-propen ] malononitrile;
THAP2,4, 6-trihydroxyacetophenone;
TBC tris (2, 3-dibromopropyl) isocyanurate;
TBBPA tetrabromobisphenol A;
TEAB tetraethylammonium bromide;
LiBr lithium bromide;
br bromine;
μ L microliter;
mg/mL;
μ g/mL;
m/z mass to charge ratio;
S/N signal-to-noise ratio;
R2a correlation coefficient;
example 1: SA and reactive matrix are combined to construct a bromine-containing compound target plate reaction strategy
(1) Preparing 10mg/mLSA methanol solution, and storing in a refrigerator at 4 ℃;
(2) respectively preparing AgTFA and AgOTf matrixes, respectively preparing 10mg/mL AgTFA and AgOTf solutions by using methanol as a solvent and AgTFA and AgOTf as solutes, and storing the AgTFA and AgOTf solutions in a refrigerator at 4 ℃;
(3) respectively preparing 500 mu g/mL methanol solutions of TBBPA, TBC and TEAB, and storing in a refrigerator at 4 ℃;
(4) taking 1 μ L of TBBPA, TBC and TEAB solution in the step (3), 1 μ L of AgOTf in the step (2) and 1 μ L of SA matrix solution in the step (1), preparing samples by using a dry drop method, and taking 1 μ L to sample on a sample application hole of a polished steel target plate. Naturally drying at room temperature of 25 ℃;
(5) as a control, 1. mu.L of TBBPA, TBC and TEAB solution in step (3) and 1. mu.L of AgTFA in step (2) and 1. mu.L of SA matrix solution in step (1) were sampled by dry drop method, and 1. mu.L was spotted on a polishestel target plate spotting well. Naturally drying at room temperature of 25 ℃;
(6) the target plate is sent into a MALDI mass spectrometer, and a negative ion reflection mode is selected for data acquisition.
In example 1, table 1 illustrates the signal-to-noise ratios of a series of mass spectral peaks obtained for TBBPA, TBC and TEAB with AgTFA or AgOTf as the reactive matrix, respectively, in combination with SA. 266.74Da corresponding to [ AgBr + Br]-Peak, 454.56Da vs. [2AgBr + Br]-Peak, 336.77Da vs. [ AgOTf + Br]-Peak, 592.63Da vs. [2AgOTf + Br]-Peak, 300.80Da vs [ AgTFA + Br]-Peak, 520.70Da vs [2AgTFA + Br]-Peak(s). FIG. 1 shows the mass spectra obtained by detecting TBBPA, TBC and TEAB with AgTFA or AgOTf as the reactive matrix in combination with SA, respectively, 266.74Da corresponding to [ AgBr + Br]-Peak(s). Fig. 1A is a higher signal-to-noise ratio than fig. 1B, fig. 1C is a higher signal-to-noise ratio than fig. 1D, and fig. 1E is a higher signal-to-noise ratio than fig. 1F. As can be seen, the reaction efficiency of the target plate based on AgOTf/SA is higher than that of AgTFA/SA.
TABLE 1
Example 2: reaction strategy for combining AgOTf with commercial matrix to construct bromine-containing compound target plate
(1) Preparing 10mg/mL of DHB, CHCA, NDA, NEDC,3-AQ, DCTB and THAP methanol solution, and storing in a refrigerator at 4 ℃;
(2) samples were prepared using dry drop method using 1 μ L of TBBPA, TBC and TEAB solutions from example 1 and 1 μ L of AgOTf from example 1, 1 μ L of SA matrix solution from example 1 or 1 μ L of DHB, CHCA, NDA, NEDC,3-AQ, DCTB or THAP matrix solution formulated in step (1), respectively, and 1 μ L was spotted onto a polished plate spotting well. Naturally drying at room temperature of 25 ℃;
(3) as controls, 1. mu.L of TBBPA, TBC and TEAB solutions of example 1 and 1. mu.L of AgOTf of example 1 were taken, respectively, sampled using the dry drop method, and 1. mu.L was spotted onto a polished steel target plate spotting well. Naturally drying at room temperature of 25 ℃;
(4) the target plate is sent into a MALDI mass spectrometer, and a negative ion reflection mode is selected for data acquisition.
In example 2, FIG. 2 shows [2AgOTf + Br obtained by AgOTf detecting TBBPA, TBC and TEAB in combination with or without SA, DHB, CHCA, NDA, NEDC,3-AQ, DCTB, THAP auxiliary substrate]-Mass peak signal to noise ratio. [2AgOTf + Br of TBBPA, TBC and TEAB when AgOTf/SA is used as the combined matrix]-The mass spectrum peak signal-to-noise ratio is high compared with other combined matrixes. It can be seen that the target plate based on AgOTf/SA reacted most efficiently for the three types of bromine-containing compounds tested.
Example 3: qualitative investigation of ability of AgOTf/SA matrix to detect different bromine-containing compounds
(1) Respectively preparing 500 mu g/mL methanol solutions of bronopol, 5, 7-dibromo-8-hydroxyquinoline, benzbromarone, bromoindigo, dibromohydantoin, tetrabromobisphenol A bis (2, 3-dibromoallyl) ether, tribromophenol, tris (tribromophenoxy) triazine and lithium bromide, and storing the methanol solutions in a refrigerator at 4 ℃;
(2) mu.L of AgOTf from example 1 and 1. mu.L of SA matrix solution from example 1 were mixed with the methanol solutions of bronopol, 5, 7-dibromo-8-hydroxyquinoline, benzbromarone, bromoindigo, dibromohydantoin, tetrabromobisphenol A bis (2, 3-dibromoallyl) ether, tribromophenol, tris (tribromophenoxy) triazine or lithium bromide from step 1, respectively, and samples were prepared by dry drop method, and 1. mu.L was spotted onto a polishel target plate spotting well.
Naturally drying at room temperature of 25 ℃;
(3) as a control, 1. mu.L of AgOTf from example 1 and 1. mu.L of SA matrix solution from example 1 were sampled by dry drop method, and 1. mu.L was spotted on a polished steel target plate spotting well.
Naturally drying at room temperature of 25 ℃;
(4) the target plate is sent into a MALDI mass spectrometer, and a negative ion reflection mode is selected for data acquisition.
In example 3, FIG. 3 is a graph showing the qualitative detection of [2AgOTf + Br ] by AgOTf/SA combination matrix of bronopol, 5, 7-dibromo-8-hydroxyquinoline, benzbromarone, bromoindigo, dibromohydantoin, tetrabromobisphenol A bis (2, 3-dibromoallyl) ether, tribromophenol, tris (tribromophenoxy) triazine and lithium bromide]-MALDI mass spectrum of (a). It can be seen that the various bromine-containing compounds tested, the AgOTf/SA combination matrix, produced corresponding mass spectra signals without background interference.
Example 4: quantitative investigation of the Linear Range of the AgOTf/SA-based method
(1) Respectively preparing 500 mu g/mL methanol solutions of LiBr, and then diluting to 200, 100, 50, 10, 5, 50 and 1 mu g/mL to obtain gradient methanol solutions of LiBr;
(2) mu.L of the AgOTf matrix solution of example 1, 1. mu.L of the SA matrix solution of example 1 and the different concentrations of LiBr solution of step 1 were taken, respectively, and samples were prepared using the dry drop method, and 1. mu.L was applied to the sample application wells of a polished steel target plate. Naturally drying at room temperature of 25 ℃;
(3) the target plate is sent into a MALDI mass spectrometer, and a negative ion reflection mode is selected for data acquisition.
In example 4, FIG. 5 shows the linear range of detection of LiBr using AgOTf/SA as the matrix. FIG. 4 shows the linear range of LiBr in the negative ion mode at 266.74Da mass-to-charge ratio, where R is found to be in good linear relationship at 3.33-500 μ g/mL2Is greater than 0.98. Therefore, the AgOTf/SA is taken as a matrix to perform quantitative analysis on the bromine-containing compounds respectively, and the target plate reaction strategy based on the AgOTf/SA can realize high-throughput quantitative detection on the bromine-containing compounds.
Example 5: AgOTf/SA quantitative determination of bromine content in water
In the invention, water samples do not need to be pretreated, and tap water, rainwater, drinking water and bromine in ultrapure water are taken as examples for explanation.
(1) Samples were taken from 1. mu.L of tap water, 1. mu.L of the AgOTf solution of example 1, and 1. mu.L of the SA matrix solution of example 1, using dry drop method, and 1. mu.L was spotted onto the spotting wells of a polished steel target plate. Naturally drying at room temperature of 25 ℃; the target plate is sent into a MALDI mass spectrometer, and data are acquired in a negative ion reflection mode;
(2) br in water sample by standard curve method-To obtain Br in each water sample-The content of (a).
In example 5, FIG. 5 shows the detection of Br in tap water using AgOTf/SA as a substrate-MALDI mass spectrum of (a). Table 2 illustrates Br in the respective water samples-And (4) content. The results show that low levels of Br were measured only in tap water-Br in the rest of the water samples-The contents are all lower than LOQ. As Br-The invention can provide important technical support and theoretical guidance for the rapid detection of bromine in environmental samples.
TABLE 2
The foregoing is a more detailed description of the invention in connection with specific preferred embodiments and it is not intended that the invention be limited to these specific details. For those skilled in the art to which the invention pertains, several simple deductions or substitutions may be made without departing from the concept, which should be construed as falling within the scope of the present invention.
Claims (10)
- Use of AgOTf as a reactive matrix in the detection of bromine-containing compounds in MALDI mass spectrometry.
- Use of AgOTf as a reaction matrix and an auxiliary matrix in combination for the detection of bromine-containing compounds in MALDI mass spectrometry.
- 3. The use according to claim 2, wherein the auxiliary substrate is at least one of sinapic acid, 2, 5-dihydroxybenzoic acid, α -cyano-4-hydroxycinnamic acid, 1, 5-naphthalenediamine, 3-aminoquinoline, naphthylethylenediamine hydrochloride, trans-2- [3- (4-tert-butylphenyl) -2-methyl-2-propen-ylannitrile, 2,4, 6-trihydroxyacetophenone, 3-hydroxy-2-picolinic acid.
- 4. The application according to claim 2, characterized in that it specifically comprises:preparing a sample by using AgOTf, an auxiliary matrix and a solution of a bromine-containing compound to be detected, and spotting the prepared sample on a polishing target spot sample hole to obtain a spotted target plate; and placing the spotted target plate to a mixed sample spot for natural drying, and performing MALDI mass spectrometry.
- 5. The use according to claim 4, wherein the preparation of the sample using the solution of AgOTf, the auxiliary matrix and the bromine-containing compound to be tested comprises:preparing AgOTf methanol solution, auxiliary matrix methanol solution and methanol solution of bromine-containing compound to be detected, respectively taking methanol solution of bromine-containing compound to be detected, AgOTf methanol solution and auxiliary matrix methanol solution with equal volumes, preparing a sample by using a dry drop method, and spotting the prepared sample on a polishing target spot sample hole to obtain a spotted target plate.
- 6. The use according to claim 5, wherein the concentration of AgOTf in the methanol solution of AgOTf is from 5 to 25 mg/mL.
- 7. The use according to claim 5, wherein the concentration of the co-substrate in the methanol solution of the co-substrate is 5-25 mg/mL.
- 8. The use according to claim 4, wherein the MALDI mass spectrometry is performed in a negative ion mode.
- 9. The use according to claim 4, wherein the MALDI mass spectrometry is performed using an ion detector in either a reflection mode or a linear mode.
- 10. The use according to claim 2, wherein said bromine-containing compounds are organic and inorganic compounds having bromine atoms.
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