WO2023071402A1 - Profil des sucres basé sur la structure fucosylée spécifique à la salive, son procédé de détection et son application - Google Patents

Profil des sucres basé sur la structure fucosylée spécifique à la salive, son procédé de détection et son application Download PDF

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WO2023071402A1
WO2023071402A1 PCT/CN2022/111996 CN2022111996W WO2023071402A1 WO 2023071402 A1 WO2023071402 A1 WO 2023071402A1 CN 2022111996 W CN2022111996 W CN 2022111996W WO 2023071402 A1 WO2023071402 A1 WO 2023071402A1
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fucose
saliva
glycan
pipette
sugar
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PCT/CN2022/111996
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English (en)
Chinese (zh)
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杨霜
蒋军红
高子媛
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苏州大学
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    • 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
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P19/00—Preparation of compounds containing saccharide radicals
    • C12P19/18—Preparation of compounds containing saccharide radicals produced by the action of a glycosyl transferase, e.g. alpha-, beta- or gamma-cyclodextrins
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P19/00—Preparation of compounds containing saccharide radicals
    • C12P19/26—Preparation of nitrogen-containing carbohydrates
    • C12P19/28—N-glycosides
    • 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
    • G01N30/04—Preparation or injection of sample to be analysed
    • G01N30/06—Preparation

Definitions

  • the invention belongs to the technical field of biomolecular analysis reagents, and in particular relates to a sugar spectrum based on saliva-specific fucosylation structure and its detection method and application.
  • the purpose of the present invention is to provide a sugar profile based on saliva-specific fucosylation structure and its detection method and application.
  • a kind of technical scheme of the present invention is:
  • a sugar profile based on saliva-specific fucosylation structure including the following general structure:
  • F is fucose
  • G is galactose
  • M is mannose
  • N is acetylglucosamine
  • ⁇ 1,2 represents the link between carbon 2 of G monosaccharide and carbon 1 of F monosaccharide
  • ⁇ 1,3 represents the connection between carbon 3 of N monosaccharide and carbon 1 of F monosaccharide
  • ⁇ 1,6 represents that carbon 6 of the N monosaccharide is connected to carbon 1 of the F monosaccharide.
  • a detection method based on saliva-specific fucosylation structural sugar profile comprising the steps of:
  • step 1) the extraction of glycans from proteins includes:
  • filling pipette Fill the hollow pipette with nano-scale porous micro-spherical resin modified with aldehyde groups on the surface, and the hollow pipette after filling is called filling pipette;
  • N-glycosidase to the filling pipette, and use ammonium bicarbonate buffer solution to enzymatically hydrolyze N-glycan from the protein immobilized on the filling pipette resin into the ammonium bicarbonate buffer solution;
  • step (3) it also includes determining any one or more of ⁇ 1,2 fucose, ⁇ 1,3 fucose and ⁇ 1,6 fucose.
  • the determination of ⁇ 1,2 fucose comprises: adding ⁇ 1-2 fucosidase to the solid phase of the filled pipette resin to enzymatically hydrolyze ⁇ 1,2 fucose; through the enzymatic hydrolysis reaction , cleavage of ⁇ 1,2 fucose from the glycan, if the molecular weight of the obtained glycan differs by one fucose, it is inferred to contain one ⁇ 1,2 fucose, and if the molecular weight of the obtained glycan differs by two fucose, it is inferred to contain two ⁇ 1,2 fucose, and so on; if the glycan still contains fucose after ⁇ 1-2 fucosidase digestion, it is inferred that the glycan may contain ⁇ 1,3 fucose and/or core ⁇ 1, 6 fucose.
  • the determination of ⁇ 1,3 fucose includes: adding ⁇ 1-2,3,4 fucosidase to the solid phase of the filled pipette resin to enzymatically hydrolyze ⁇ 1,3 fucose; The above enzymatic hydrolysis reaction cuts ⁇ 1,3 fucose from the glycan. If the molecular weight of the obtained glycan differs by one fucose, it is inferred that it contains one ⁇ 1,3 fucose.
  • the glycan may be the core ⁇ 1,6 rock algalose.
  • the determination of ⁇ 1,6 fucose includes: adding ⁇ 1-2,4,6 fucosidase to the solid phase of the filled pipette resin to enzymatically hydrolyze ⁇ 1,6 fucose; The above enzymatic hydrolysis reaction cuts ⁇ 1,6 fucose from the glycan. If the molecular weight of the obtained glycan differs by one fucose, it is inferred that it contains a core ⁇ 1,6 fucose.
  • the molecular weight of the obtained glycan differs by two fucose, It is inferred to contain two core ⁇ 1,6 fucose, and so on; if the glycan still contains fucose after ⁇ 1-2,4,6 fucosidase digestion, it is confirmed that the glycan contains ⁇ 1,3 rock algalose.
  • the method for determining the glycan-fucose linkage includes: immobilizing the glycoprotein on the solid phase of the filled pipette resin, and enzymatically cutting the solid phase with fucosidase .
  • the present invention provides a glycan profile based on saliva-specific fucosylation structure and its detection method.
  • the fucosylated polysaccharide specific for lung cancer is identified.
  • Sugar markers are used in the diagnosis and detection of lung cancer.
  • Filling pipettes can be used to process samples on a large scale using automated liquid handling instruments.
  • filling pipettes can be set in 96-well or 384-well plates, and Agilent Bravo Automated Liquid Handling Platform can be used for 96 or 384 clinical samples at the same time to test;
  • the present invention can also analyze the glycan profile of other clinical samples, including urine, lung lavage fluid, gastric lavage fluid, blood, and brain and spinal cord.
  • Fig. 1 is a schematic structural diagram of a sugar spectrum based on saliva-specific fucosylation structure according to the present invention
  • Fig. 2 is a schematic workflow diagram of adopting pipette filling resin immobilization and enzymolytic removal of glycans in the present invention
  • Fig. 3 is a schematic diagram of the determination of glycan-fucose-linked fucosidase analysis in the present invention
  • Figure 4 is a schematic diagram of the analysis of the structure and abundance of saliva-specific fucose in the present invention.
  • Fig. 5 is a comparison chart of the composition and abundance of sialoglycan in lung cancer patients, non-lung cancer and healthy people in the present invention.
  • the invention discloses a detection method based on saliva-specific fucosylation structure sugar spectrum.
  • human saliva samples are collected, then proteins are extracted from saliva, and then glycans are hydrolyzed and enriched from glycoproteins, and then mass spectrometry is used to Analyze the glycan structure and quantitatively analyze the abundance, and finally determine the glycan spectrum in the sample.
  • mass spectrometry is used to Analyze the glycan structure and quantitatively analyze the abundance, and finally determine the glycan spectrum in the sample.
  • mass spectrometry is used to Analyze the glycan structure and quantitatively analyze the abundance, and finally determine the glycan spectrum in the sample.
  • mass spectrometry is used to Analyze the glycan structure and quantitatively analyze the abundance, and finally determine the glycan spectrum in the sample.
  • the sugar profile of high-abundance core fucose and branched chain fucose is identified, which can be used for clinical screening of lung cancer. This method
  • one embodiment or “embodiment” referred to herein refers to a specific feature, structure or characteristic that may be included in at least one implementation of the present invention. "In one embodiment” appearing in different places in this specification does not all refer to the same embodiment, nor is it a separate or selective embodiment that is mutually exclusive with other embodiments.
  • a sugar profile based on saliva-specific fucosylation structure including the following general structure:
  • F is fucose
  • G is galactose
  • M is mannose
  • N is acetylglucosamine
  • ⁇ 1,2 represents the link between carbon 2 of G monosaccharide and carbon 1 of F monosaccharide
  • ⁇ 1,3 represents the connection between carbon 3 of N monosaccharide and carbon 1 of F monosaccharide
  • ⁇ 1,6 represents that carbon 6 of N monosaccharide is connected with carbon 1 of F monosaccharide;
  • FIG. 1 is a schematic structural diagram of a sugar profile based on saliva-specific fucosylation structure according to the present invention.
  • FIG. 2 is a schematic workflow diagram of using a pipette to fill resin to immobilize and enzymatically remove glycans in the present invention. as shown in picture 2,
  • Adjusting the pH of the sample to pH 10 accelerates the binding of the protein to the aldehyde groups of the solid-phase resin in the filled pipette by adding a buffer solution of sodium citrate and sodium acetate to a final concentration of 100 mM sodium citrate , 50 millimolar sodium acetate, react at room temperature for 2-3 hours, the protein N-terminal and/or lysine react with the aldehyde group on the solid phase resin;
  • N-glycosidase PNGase F New England BioLabs, USA
  • FIG. 3 is a schematic diagram of fucosidase analysis for determination of glycan-fucose-linked fucosidase in the present invention.
  • the glycoprotein was immobilized on the solid phase of the filled pipette resin by the method of Example 1, and the glycan structure was (H 5 N 4 F3 or H 5 N 4 F(1,3)F(1 ,2 ) F(1,6)) was digested with fucosidase on the solid phase, where the solid circles represent mannose, the hollow circles represent galactose, and the squares represent N-acetylglucosamine or N-acetylgalactosamine , the triangle represents fucose.
  • the following steps (1), (2) and (3) are carried out before the preparation of N-glycans in step 3 of Example 1, and these 3 steps can be carried out in parallel;
  • This reaction enzymatically cleaves ⁇ 1,2 fucose from the glycan. If the molecular weight of the resulting glycan differs by one fucose, it is inferred to contain one ⁇ 1,2 fucose.
  • the molecular weight of the obtained glycan differs by two fucose, it is inferred Contains two ⁇ 1,2 fucose, and so on, the principle of the above reaction is: ⁇ 1,2 fucose is enzymatically cleaved from the glycan, and the resulting glycan has a molecular weight difference of 146.0-146.4Da, that is, it contains one ⁇ 1,2 fucose algalose, the resulting glycan has a molecular weight difference of 292.0-292.8Da, which means it contains two ⁇ 1,2 fucose, and so on;
  • the sugar may contain ⁇ 1,3 fucose and/or core ⁇ 1,6 fucose.
  • This reaction enzymatically cleaves ⁇ 1,3 fucose from the glycan. If the molecular weight of the resulting glycan differs by one fucose, it is inferred to contain one ⁇ 1,3 fucose, and if the molecular weight of the resulting glycan differs by two fucose, it is inferred to contain Two ⁇ 1,3 fucose, and so on, the principle of the above reaction is: ⁇ 1,3 fucose is enzymatically cleaved from the glycan, and the resulting glycan has a molecular weight difference of 146.0-146.4Da, which means that there is one ⁇ 1,3 fucose Sugar, the molecular weight difference of the obtained glycan is 292.0-292.8Da, that is, it contains two ⁇ 1,3 fucose, and so on; if the polysaccharide still contains fucose after ⁇ 1-2,3,4 fucosidase digestion
  • This reaction enzymatically cleaves ⁇ 1,6 fucose from the glycan. If the molecular weight of the resulting glycan differs by one fucose, it is inferred to contain a core ⁇ 1,6 fucose.
  • the molecular weight of the resulting glycan differs by two fucose molecular weights, it is inferred Contains two core ⁇ 1,6 fucose, and so on, the principle of the above reaction is: ⁇ 1,6 fucose is digested from the glycan, and the molecular weight difference of the obtained glycan is 146.0-146.4Da, which confirms that it contains a core ⁇ 1 ,6 fucose, the molecular weight difference of the obtained glycan is 292.0-292.8Da, that is, it is confirmed that it contains two core ⁇ 1,6 fucose, and so on; If fucose is still contained, it is confirmed that the glycan contains ⁇ 1,3 fucose.
  • Fig. 4 is a schematic diagram of the analysis of the structure and abundance of saliva-specific fucose in the present invention.
  • F2 ⁇ 1,2 fucosidase
  • FIG. 4 is a schematic diagram of the analysis of the structure and abundance of saliva-specific fucose in the present invention.
  • (a) use ⁇ 1,2 fucosidase (F2) to determine the result of ⁇ 1,2 fucose, accompanied by the increase of other fucose glycans, in the figure for H 5 N 4 F 4 and H 5 N 4
  • the two fucose glycans of F3 were analyzed by enzymatic hydrolysis of F2, and the structures of these two glycans were confirmed.
  • the structure contains four fucose, namely two ⁇ 1,2, one ⁇ 1,3 and one core ⁇ 1,6;
  • Mass spectrometry identified that H 5 N 4 F(1,2) 2 (1,6) decreased, H 5 N 4 F(1,2)(1,6) increased, and H 5 N 4 F(1,6) increased at the same time, It is determined that saliva contains the core ⁇ 1,6 structure; if saliva contains H 5 N 4 F(1,2) 2 (1,3)(1,6), after ⁇ 1-2,4,6 fucosidase (F234 ) digestion, H 5 N 4 F(1,2) 2 (1,6), H 5 N 4 F(1,2)(1,6) and H 5 N 4 F(1,6) all increased, determine the glycan structure and abundance;
  • Saliva-specific fucosylation structure sugar profile has different characteristics in lung cancer patients and non-lung cancer and healthy people
  • Figure 5 is the structure of sialoglycans of the present invention in lung cancer patients and non-lung cancer and healthy people Composition and abundance comparison.
  • sugar 6 and sugar 10 were highly expressed, and the abundance of other glycans was low or not detected; in non-cancer people, the abundance of glycans 9, 12, 14 and 16 was However, other glycans were less abundant or not detected; in lung cancer patients, fucose glycans were highly abundant, and the most prominent glycans were 1, 2, 3, 4, 7, 8, 11, 12, 13 , 14, 16, 17 and 19.
  • glycans all contain ⁇ 1,6 core fucose, and the high molecular weight ammoglycans contain one or more ⁇ 1,2 and ⁇ 1,3. It can be concluded that there are specific high-fucosylated glycans in the saliva of cancer patients, and the abundance is much higher than that of other groups.
  • the glycoprotein glycans in 500 grams of saliva were enriched and extracted, and the structure and abundance of the glycans were analyzed by mass spectrometry, measured using 1/10 of the extracted glycans, and the mass-to-charge ratio test range was from 1200Da to 3000Da.
  • the mass-to-charge ratios of healthy people, non-cancer (or other diseases) and lung cancer patients are aligned, and the coordinates of glycan abundance are adjusted to be consistent (10 4 ).
  • Each peak represents a component of glycan, and the height represents the relative content of glycan.
  • the specific glycans contained in lung cancer saliva include: sugar 1, sugar 2, sugar 3, sugar 4, sugar 5, sugar 7, sugar 10, sugar 11, sugar 13, sugar 15, sugar 16, sugar 17, sugar 19, Sugar 20, sugar 21; healthy people high-abundance glycans include: sugar 6, sugar 10, sugar 14.
  • the sialoglycans of non-cancer population include: sugar 9, sugar 12, sugar 14, sugar 16, sugar 20.
  • the specific fucose structure sugar profile of lung cancer saliva is obtained by analyzing clinical samples, and the glycan structure and abundance are prepared and analyzed for lung cancer patients, non-lung cancer patients and healthy people according to the method described in the present invention. Please refer to Table 1, Table 1 is the human saliva samples detected by the present invention.
  • the clinical samples included healthy people (10), non-cancer patients (20), and lung cancer patients (21).
  • the average age of these three groups is 44, 56 and 69, covering the age range from 20 to 84 years old, and includes male and female patients.
  • the number of smokers is healthy (3), non-cancer patient (11) and lung cancer patient (13).
  • the glycan profile of glycans is shown in Figure 5.
  • the glycan profiles of all samples have similar composition and abundance composition, and the hourly error of statistical analysis is 10-15%.
  • the saliva of patients with lung cancer contains glycan structures sugar 4, sugar 7, sugar 8, sugar 11, sugar 13, sugar 15, sugar 16, sugar 17, and sugar 19.
  • Non-cancer patients contain sugar 9 and sugar 12, and compared with healthy people, the content of sugar 6 and sugar 10 is extremely low.
  • the beneficial effects of the present invention are: the present invention provides a sugar profile based on saliva-specific fucosylation structure and its detection method and application, which is convenient for early diagnosis, easy to collect samples, and There is no harm to patients and has excellent application prospects.

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Abstract

L'invention concerne un profil des sucres basé sur la structure fucosylée spécifique à la salive, son procédé de détection, et son application. Le procédé comprend : tout d'abord la collecte d'un échantillon de salive humaine ; puis l'extraction de protéines à partir de la salive ; puis la réalisation d'une enzymolyse et d'un enrichissement en glycanes à partir des glycoprotéines ; et la réalisation d'une analyse de structure et d'une analyse quantitative de l'abondance sur les glycanes à l'aide de la spectrométrie de masse pour finalement déterminer un profil des glycanes dans l'échantillon. En analysant la salive saine, la salive non cancéreuse et la salive du cancer du poumon, des profils des sucres de fucose de noyau et de fucose ramifié à haute abondance sont identifiés. Le procédé peut être appliqué au dépistage clinique du cancer du poumon. Le profil des sucres basé sur la structure fucosylée spécifique à la salive et son procédé de détection facilitent un diagnostic précoce, caractérisent des échantillons faciles à collecter, et ne sont pas nocifs pour un patient, et ont ainsi une excellente perspective d'application et une importance significative dans les aspects du dépistage précoce et du traitement du cancer du poumon à forte morbidité et à taux de mortalité élevé.
PCT/CN2022/111996 2021-10-28 2022-08-12 Profil des sucres basé sur la structure fucosylée spécifique à la salive, son procédé de détection et son application WO2023071402A1 (fr)

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