CN116068110A - Synthesis method and application of azide mass spectrometry probe - Google Patents
Synthesis method and application of azide mass spectrometry probe Download PDFInfo
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- 239000000523 sample Substances 0.000 title claims abstract description 31
- 150000001540 azides Chemical class 0.000 title claims abstract description 27
- 238000004949 mass spectrometry Methods 0.000 title claims abstract description 27
- 238000001308 synthesis method Methods 0.000 title claims abstract description 8
- 239000000126 substance Substances 0.000 claims abstract description 16
- 238000004458 analytical method Methods 0.000 claims abstract description 12
- 150000001345 alkine derivatives Chemical class 0.000 claims abstract description 10
- 238000004454 trace mineral analysis Methods 0.000 claims abstract description 4
- -1 Hexafluorophosphate Chemical compound 0.000 claims description 27
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- PQXPAFTXDVNANI-UHFFFAOYSA-N 4-azidobenzoic acid Chemical compound OC(=O)C1=CC=C(N=[N+]=[N-])C=C1 PQXPAFTXDVNANI-UHFFFAOYSA-N 0.000 claims description 7
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 claims description 7
- 239000012535 impurity Substances 0.000 claims description 6
- 239000012317 TBTU Substances 0.000 claims description 4
- CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 claims description 4
- 239000003153 chemical reaction reagent Substances 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000005619 boric acid group Chemical group 0.000 claims description 2
- 238000012650 click reaction Methods 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000003550 marker Substances 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 230000002194 synthesizing effect Effects 0.000 claims description 2
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 238000010189 synthetic method Methods 0.000 claims 1
- 238000005481 NMR spectroscopy Methods 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000001514 detection method Methods 0.000 description 5
- 238000001819 mass spectrum Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000011159 matrix material Substances 0.000 description 4
- UHOVQNZJYSORNB-MZWXYZOWSA-N deuterated benzene Substances [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- 239000007790 solid phase Substances 0.000 description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- 206010070834 Sensitisation Diseases 0.000 description 2
- 150000001448 anilines Chemical class 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 238000006352 cycloaddition reaction Methods 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000012216 screening Methods 0.000 description 2
- 230000008313 sensitization Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000012377 drug delivery Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 238000004896 high resolution mass spectrometry Methods 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000000155 isotopic effect Effects 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 239000003068 molecular probe Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 239000000700 radioactive tracer Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C247/00—Compounds containing azido groups
- C07C247/16—Compounds containing azido groups with azido groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C247/18—Compounds containing azido groups with azido groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by carboxyl groups
-
- 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid compounds
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/62—Detectors specially adapted therefor
- G01N30/72—Mass spectrometers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/05—Isotopically modified compounds, e.g. labelled
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Other Investigation Or Analysis Of Materials By Electrical Means (AREA)
Abstract
The application discloses a synthesis method and application of an azide mass spectrometry probe. The azide mass spectrometry probe is applied to trace analysis or identification analysis of alkyne substances, and has the following molecular structural formula,
wherein R is selected from the group consisting of-H-D
The technical scheme can better realize trace analysis or identification analysis of alkyne substances.
Description
Technical Field
The application relates to the technical field of mass spectrometry probes, in particular to a synthesis method and application of an azide mass spectrometry probe.
Background
The azide-alkynyl cycloaddition reaction is a classical click chemistry reaction, has the advantages of high selectivity, good biocompatibility, mild reaction conditions, high reaction yield and the like, and has been applied to the research fields of molecular imaging, drug delivery, metabolite identification and the like. Click chemistry applications typically require the incorporation of highly efficient molecular probes to increase the sensitivity of detection. Mass spectrometry is the dominant tool in the analysis of small molecules of compounds and large molecules of proteins. Aiming at the characteristics of mass spectrum detection, the design and synthesis of the high-efficiency mass spectrum probe based on the click chemistry principle have important significance for improving the detection sensitivity of target molecules, improving the recognition selectivity of molecules and the like. Through reasonable design, the molecular structure of the mass spectrum probe can comprise an azide reaction group which has cycloaddition reaction with alkynyl, an easy-ionization group which promotes mass spectrum signal sensitization, and an isotope coding group which improves mass spectrum recognition performance.
Disclosure of Invention
In view of the above, the application provides a synthesis method and application of an azide mass spectrometry probe, which can potentially realize trace analysis or identification analysis of alkyne substances.
In a first aspect, the present application provides the use of an azide mass spectrometry probe in the tracer analysis of acetylenic substances, the azide mass spectrometry probe having the following molecular structural formula,
wherein R is selected from
In a second aspect, the present application provides the use of an azide mass spectrometry probe in the identification analysis of acetylenic species, the azide mass spectrometry probe having the following molecular structural formula,
wherein R is selected from
Suitably, but not by way of limitation, the identification analysis specifically comprises the steps of:
A. marking the alkyne substance to be detected by adopting an azide mass spectrometry probe through the click reaction of azide and alkynyl to form a marker conjugate;
B. obtaining liquid chromatography-mass spectrometry results for the label conjugate;
C. and obtaining qualitative and quantitative results of the alkyne substances by analyzing the liquid chromatography-mass spectrometry results.
Suitably, but not limitatively, the identification assay further comprises impurity removal enrichment after step a.
Suitably, but not limitatively, the reagent used for the impurity removal and enrichment is an azide mass spectrometry probe containing a boric acid group.
The structure of the azide mass spectrometry probe is designed based on the adaptation of a liquid chromatography-mass spectrometry system.
In a third aspect, the present application provides a method for synthesizing an azide mass spectrometry probe, wherein 4-azidobenzoic acid and an aniline derivative are dissolved in a solvent, and a condensing agent and triethylamine are added to react.
As an exemplary specific example, the solvent is methylene chloride or N, N-dimethylformamide;
here, the molar ratio of 4-azidobenzoic acid to aniline derivative is (1.0-1.5): 1;
here, the condensing agent is O-benzotriazol-N, N, N ', N' -tetramethyluronium Hexafluorophosphate (HBTU) or O-benzotriazol-N, N, N, N-tetramethyluronium tetrafluoroborate (TBTU);
here, the reaction temperature is 25 to 30℃and the reaction time is 5 to 10 hours.
Drawings
Technical solutions and other advantageous effects of the present application will be made apparent from the following detailed description of specific embodiments of the present application with reference to the accompanying drawings.
FIG. 1 is an NMR chart of 4-azidobenzamidobenzene provided herein.
FIG. 2 is an NMR chart of 4-azidobenzamido deuterated benzene provided herein.
FIGS. 3a-b provide NMR diagrams of (4- (4-azidobenzamido) phenylboronic acid for the present application.
Detailed Description
The technical solutions in the embodiments of the present application will be clearly and completely described below in connection with the embodiments of the present application. It will be apparent that the described embodiments are only some, but not all, of the embodiments of the present application. All other embodiments, which can be made by those skilled in the art based on the embodiments herein without making any inventive effort, are intended to be within the scope of the present application.
In the description of the present application, it should be understood that the terms "first," "second," and the like are used for descriptive purposes only and are not to be construed as indicating or implying a relative importance or an implicit indication of the number of technical features being indicated. Thus, a feature defining "a first" or "a second" may explicitly or implicitly include one or more of the described features. In the description of the present application, the meaning of "a plurality" is two or more, unless explicitly defined otherwise.
In the description of the present application, it should be noted that, unless explicitly specified and limited otherwise, the terms "mounted," "connected," and "connected" are to be construed broadly, and may be either fixedly connected, detachably connected, or integrally connected, for example; can be mechanically connected, electrically connected or can be communicated with each other; can be directly connected or indirectly connected through an intermediate medium, and can be communicated with the inside of two elements or the interaction relationship of the two elements. The specific meaning of the terms in this application will be understood by those of ordinary skill in the art as the case may be.
The following disclosure provides many different embodiments or examples for implementing different structures of the present application. In order to simplify the disclosure of the present application, the components and arrangements of specific examples are described below. Of course, they are merely examples and are not intended to limit the present application. Furthermore, the present application may repeat reference numerals and/or letters in the various examples, which are for the purpose of brevity and clarity, and which do not in themselves indicate the relationship between the various embodiments and/or arrangements discussed. In addition, the present application provides examples of various specific processes and materials, but one of ordinary skill in the art may recognize the application of other processes and/or the use of other materials.
The structural formula of the synthesis process and related products of the azide mass spectrometry probe are as follows:
wherein R is selected from
Example 1
Synthesis of 4-azidobenzamido benzene (1 a)
4-azidobenzoic acid (15 mmoL) and aniline (10 mmoL) were dissolved in methylene chloride (30 mL) at room temperature, TBTU (10 mmoL) and triethylamine (20 mmoL) were added thereto, and the mixture was stirred at room temperature for 5 hours. After the reaction, quench the reaction with water, extract three times with dichloromethane, wash the combined organic layers once with saturated brine, dry with anhydrous sodium sulfate and filter, rotary evaporate the filtrate to give crude product, purify with silica gel column chromatography (petroleum ether/dichloromethane=4:1) to give 4-azidobenzamide benzene (1 a) as a white solid, yield 90.2%; HRMS [ M+H ]] + 239.0924 theoretical value [ M+H ]] + = 239.0927;1H NMR (400 MHz, DMSO-d 6) delta 10.24 (s, 1H), 8.13-7.98 (m, 2H), 7.84-7.74 (m, 2H), 7.40-7.23 (m, 4H), 7.15-7.06 (m, 1H) (nuclear magnetic resonance spectrum is shown in FIG. 1).
Example two
Synthesis of 4-azidobenzamido benzene (1 a)
4-azidobenzoic acid (11 mmoL) and aniline (10 mmoL) were dissolved in N, N-dimethylformamide (20 mL) at room temperature, TBTU (10 mmoL) and triethylamine (20 mmoL) were added thereto, and the mixture was stirred at room temperature for 10 hours. After the reaction was completed, water (100 mL) was added and stirred, and a precipitate was precipitated, then filtered, and the filter cake was rinsed with water (2 ml×5), and dried in vacuo to give 4-azidobenzamide benzene (1 a) as a white solid in a yield of 95.5%.
Example III
Synthesis of 4-azidobenzamido benzene (1 a)
4-azidobenzoic acid (11 mmoL) and aniline (10 mmoL) were dissolved in N, N-dimethylformamide (20 mL) at room temperature, HBTU (10 mmoL) and triethylamine (20 mmoL) were added thereto, and the mixture was stirred at room temperature for 10 hours. After the reaction was completed, water (100 mL) was added and stirred, and a precipitate was precipitated, then filtered, and the filter cake was rinsed with water (2 ml×5), and dried in vacuo to give 4-azidobenzamide benzene (1 a) as a white solid in 94.9% yield.
Example IV
Synthesis of 4-azidobenzamido deuterated benzene (1 b)
The synthesis method is described in example two. Obtaining white solid 4-azidobenzamido deuterated benzene (1 b) with the yield of 95.0 percent; HRMS [ M+H ]] + 244.1227 theoretical value [ M+H ]] + ＝244.1241； 1 H NMR (400 MHz, DMSO-d 6) δ10.24 (s, 1H), 8.07-8.00 (m, 2H), 7.28 (d, J=8.6 Hz, 2H) (nuclear magnetic resonance spectrum as shown in FIG. 2).
Example five
Synthesis of (4- (4-azidobenzamido) phenylboronic acid (1 c)
The synthesis method is described in example two. Obtaining pale yellow solid (4- (4-azidobenzamido) phenylboronic acid (1 c) with the yield of 92.0%; 1 H NMR(400MHz,DMSO-d6)δ10.26(s,1H),8.08–7.99(m,2H),7.95(s,2H),7.84–7.68(m,4H),7.33–7.22(m,2H). 13 c NMR (101 MHz, DMSO-d 6) delta 165.01,143.21,141.23,135.18,131.79,130.13,119.56,119.46 (nuclear magnetic resonance spectroscopy is shown in FIGS. 3 a-b).
Application example 1
Screening and quantification of alkyne markers on a liquid phase mass spectrometry analysis technology platform are realized by using a pair of isotope reagents, and the mechanism is shown as the formula:
the physicochemical properties of the derivative products based on isotopic reagents are the same, and therefore the chromatographic retention is the same. And screening the acetylenic substances by combining the mass-to-charge ratio difference values of the acetylenic substances with fixed values. And (3) taking the standard substance marked by the 1b as an internal standard to realize quantitative detection of alkyne substances.
Application example 2
Liquid chromatography-mass spectrometry analysis of acetylenic substances is realized by utilizing boron affinity products of 1c and a solid phase matrix, and the mechanism is shown as the formula:
the 1c and the cis-diol solid phase matrix form a chemoselective probe with the functions of impurity removal, enrichment and sensitization through boron affinity reaction. After the azide probe reacts with the sample containing the alkyne substance, the sample matrix can be removed by washing under neutral or alkaline conditions due to the insolubility of the solid phase product, and then the labeled product molecules are released under acidic conditions so as to be suitable for liquid chromatography mass spectrometry analysis. The method integrates the impurity removal and derivatization of the sample, is beneficial to reducing the matrix effect of mass spectrometry and improving the detection sensitivity of the to-be-detected object. In addition, according to 10 B and 11 the characteristic that the abundance ratio of the two natural isotopes is 0.248 can realize the rapid identification of the marked products during high-resolution mass spectrometry.
The foregoing is merely a preferred embodiment of the present application, but the scope of the present application is not limited thereto, and any changes or substitutions easily contemplated by those skilled in the art within the technical scope of the present application should be covered by the scope of the present application.
Claims (10)
1. An application of an azide mass spectrometry probe in the trace analysis of acetylenic substances is characterized in that the azide mass spectrometry probe has the following molecular structural formula,
wherein R is selected from-H, -D,
2. An application of an azide mass spectrometry probe in the identification and analysis of acetylenic substances is characterized in that the azide mass spectrometry probe has the following molecular structural formula,
wherein R is selected from-H, -D,
3. The use according to claim 2, characterized in that said authentication analysis comprises in particular the following steps:
A. marking the alkyne substance to be detected by adopting an azide mass spectrometry probe through the click reaction of azide and alkynyl to form a marker conjugate;
B. obtaining liquid chromatography-mass spectrometry results for the label conjugate;
C. and obtaining qualitative and quantitative results of the alkyne substances by analyzing the liquid chromatography-mass spectrometry results.
4. The use according to claim 3, wherein the identification analysis further comprises impurity removal enrichment after step a.
5. The method according to claim 4, wherein the reagent used for removing impurities and enriching is an azide mass spectrometry probe containing a boric acid group.
6. A method for synthesizing an azide mass spectrometry probe, wherein the azide mass spectrometry probe is a compound corresponding to the application of claim 1; the synthesis method comprises the steps of dissolving 4-azidobenzoic acid and aniline derivatives in a solvent, and adding condensing agent and triethylamine to react.
7. The method according to claim 6, wherein the solvent is methylene chloride or N, N-dimethylformamide.
8. The method according to claim 6, wherein the molar ratio of the 4-azidobenzoic acid to the aniline derivative is 1 (1.0-1.5): 1.
9. The synthetic method of claim 6, wherein the condensing agent is O-benzotriazol-N, N' -tetramethyluronium Hexafluorophosphate (HBTU) or O-benzotriazol-N, N-tetramethyluronium tetrafluoroborate (TBTU).
10. The method according to claim 6, wherein the reaction temperature is 25 to 30℃and the reaction time is 5 to 10 hours.
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