WO2007121668A1 - Réactif de chimiluminescence directe pour séparation magnétique, et méthode de dosage immunologique utilisant le réactif - Google Patents

Réactif de chimiluminescence directe pour séparation magnétique, et méthode de dosage immunologique utilisant le réactif Download PDF

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Publication number
WO2007121668A1
WO2007121668A1 PCT/CN2007/001295 CN2007001295W WO2007121668A1 WO 2007121668 A1 WO2007121668 A1 WO 2007121668A1 CN 2007001295 W CN2007001295 W CN 2007001295W WO 2007121668 A1 WO2007121668 A1 WO 2007121668A1
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Prior art keywords
magnetic separation
magnetic
isoluminol
fitc
direct chemiluminescence
Prior art date
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PCT/CN2007/001295
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English (en)
Chinese (zh)
Inventor
Wei Rao
Hongtao Song
Tinghua Li
Jia Shao
Ying Yan
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Shenzhen New Industries Biomedical Engineering Co., Ltd.
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Application filed by Shenzhen New Industries Biomedical Engineering Co., Ltd. filed Critical Shenzhen New Industries Biomedical Engineering Co., Ltd.
Publication of WO2007121668A1 publication Critical patent/WO2007121668A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
    • C07D237/36—Benzo-cinnolines
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • C09K11/07—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials having chemically interreactive components, e.g. reactive chemiluminescent compositions
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
    • G01N33/531—Production of immunochemical test materials
    • G01N33/532—Production of labelled immunochemicals
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
    • G01N33/543—Immunoassay; Biospecific binding assay; Materials therefor with an insoluble carrier for immobilising immunochemicals
    • G01N33/54313—Immunoassay; Biospecific binding assay; Materials therefor with an insoluble carrier for immobilising immunochemicals the carrier being characterised by its particulate form
    • G01N33/54326—Magnetic particles
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/58—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances

Definitions

  • the present invention relates to a magnetic separation direct chemiluminescence reagent and a test method using the same, in particular, an isoluminol derivative is used as a label, nano magnetic micro Beads are used as reagents for separating materials.
  • an isoluminol derivative is used as a label
  • nano magnetic micro Beads are used as reagents for separating materials.
  • methods for accurate quantitative analysis of trace active substances in human serum or urine mainly include radioimmunoassay methods, enzyme immunoassay methods, direct chemiluminescence methods for enzymatic chemiluminescence or acridinium ester labeling, and pyridinium-labeled Electrochemiluminescence method.
  • Radioimmunoassay uses a radioisotope I 125 as a tracer, labeled on an antigen or a corresponding antibody, and determines the content of the substance to be tested by measuring the intensity of 5 radiation on a gamma ray detector.
  • the purpose of quantitative analysis of trace active substances is better solved, but the defects are obvious:
  • the radioactive isotope I 125 is used as a tracer technology to pollute the environment during the manufacture, storage and application of reagents.
  • Enzyme immunoassay method uses HRP horseradish peroxidase as luminescent marker, plastic microplate as carrier and separation technology, 0PD o-phenylenediamine as chromogenic substrate, 1M3 ⁇ 4S0 4 as stop solution for enzyme color reaction
  • concentration of the substance to be tested is analyzed by measuring the absorbance value of the enzyme reaction product at a wavelength of 492 rai.
  • This method is mainly used for qualitative screening of large-scale human serum samples, and the defect is that the color intensity of the color-developing product is with time. Change and change, can not be fixed, chromogenic substrate 0PD, etc. are strong carcinogens, and the sensitivity of a considerable part of the micro-skills is not enough, the reaction time is too long, it is difficult to confirm the operation To standardize.
  • the enzymatic chemiluminescence immunoassay method uses alkaline phosphatase AKP or horseradish HRP as a label, and AMPPD (adamantane) or luminol, 3 ⁇ 40 2 as a luminescent substrate; the advantage is that the analyte is converted into a The measured optical signal significantly improves the sensitivity of the analysis.
  • the disadvantage is that many factors affecting the enzyme activity, such as ambient temperature, incubation temperature and time, storage conditions, etc., will directly affect the measurement results, and the stability of the reagent is not good;
  • the luminescence reaction of the method starts slowly, and it takes a certain time to incubate at 37 ° C to reach the illuminating platform, which will more strongly affect the luminescence measurement results.
  • the object of the present invention is to provide a magnetic separation direct chemiluminescence reagent for the above-mentioned deficiencies in the prior art, in particular, magnetic materials using isoluminol derivatives as labels and nano magnetic beads as separation materials. Chemical direct luminescent reagent.
  • the magnetic separation direct chemiluminescence reagent comprises a luminescent label, a separation reagent, a FITC-antibody conjugate and a standard antigen or antibody, wherein the luminescent label is different
  • the luminol derivative, the isoluminol derivative structure is: Wherein: R1 is C 2 3 ⁇ 4 , C 3 H 7 or C 4 , and R 2 is NH 2 - (CH 2 ) 4 , 3 ⁇ 4- (CH 2 ) 6 , N 3 ⁇ 4- ( CH 2 ) 8 or Leg 2 - ( C3 ⁇ 4 ) 10
  • ABEI and AHEEI wherein R1 is C 2 H 5 , R 2 is NH 2 - (CH 2 ) 4 or NH 2 - (CH 2 ) 6 ;
  • the separating reagent is a nano magnetic microbead described by a goat anti-FITC coated nano magnetic microbead, which is coated with Fe 3 0 4 or Fe 2 0 3 and contains - 0H, - C00H, - H outside. 2 reactive group microbeads, preferably -C00H and -H 2 , having a reactive group content of 0.05-0.5 eqm/g; said goat anti-FITC coated nanomagnetic microbeads are on the monoclonal antibody or antigen mark.
  • the following steps are carried out by the present invention for analysis and testing:
  • the immune nano magnetic beads coated with the FITC polyclonal antibody are added to the goat;
  • the antigen-antibody complex is specifically separated, and after washing with a washing liquid, the bottom tube is placed in the measuring chamber;
  • the monoclonal antibody of the isoluminol derivative luminescent label is obtained by linking an illuminating marker of an isoluminol derivative with carbon dichloride or N-hydroxysuccinic acid, and then with a monoclonal antibody.
  • the bottom of the test tube is a nano magnetic microbead as a carrier.
  • the magnetic separation direct chemiluminescence immunoassay test method can be divided into a sandwich method and a competition method, and the design formulas thereof are shown in FIG. 1 and FIG. 2 respectively.
  • A* and Ag* respectively indicate that the label is on the Ab fl Ag.
  • the Mino derivatives ABEI or AHEI, Add AbTM indicate that FITC small molecules are labeled on Ab 2 Ab, and FITC is fluorescein isothiocyanate.
  • nano-immunomagnetic microbeads are used as the carrier of the antibody and the separation reagent of the antigen-antibody immune complex, which greatly shortens the time of the immune reaction, wherein the isolation reaction time takes only 5 minutes, and the entire immune reaction time takes only 20 minutes, and High accuracy and high precision of test results;
  • Figure 1 is a schematic diagram of a magnetic separation direct chemiluminescence immunospinning method
  • Figure 2 is a design diagram of magnetic separation direct chemiluminescence immunocompetition
  • the invention adopts artificial synthesis of isoluminol derivatives as luminescent markers, which are directly labeled in the antigen Or on the antibody, the NH 2 on the side chain of the isoluminol ring is activated by CSC1 2 to form an isothiocyanate derivative, and the -N di-OS bond is directly linked to the antigen or the amine group on the antibody, and is separated and purified.
  • the chemiluminescence reaction of isoluminol is an alkaline environment caused by the excitation reagent NaOH in the presence of metals Mn 2+ , Fe 2+ , CIO-, etc.
  • the visible light having a wavelength of 400-600 nm is generated by the oxidation reaction of the isoluminol derivative with the excitation reagent 3 ⁇ 40 2 to form a typical direct chemiluminescence reaction.
  • the nano magnetic beads measuring surface groups the beads are dispersed in 10- 2 M Nacl solution, measuring a C00H or -NH 2 content of the bead surface by potentiometric titration with a titrant 5X 10 a 3 M NaOH solution, dual endpoint titration obtain the parallel line method, calculated per gram of bead surface carboxyl, amino or hydroxyl group content of 0. 05-0.
  • the analyzer includes power supply circuit, automatic injection pump 1 and 2, measuring room, illuminating chamber, photomultiplier tube counter and output system. It is also equipped with Windows and control software for computer and Chinese interface. Data entry, result summary, quality Control, result storage and result inquiry, can complete a variety of analysis mode programming, quantitative or qualitative report results, automatically generate and store, update functions, two points automatically correct the standard curve.
  • Example 1
  • the preparation of the monoclonal antibody labeled with the isoluminol derivative Take 3 in 2 AB of ABAI, dissolved in 0. 2 ml of secondary water, 3. 5 mmol of CSCl 2 dissolved in 0.3 ml of DMF, the two are evenly mixed, room temperature After 2 h of reaction, take 10 mg of anti-CEA- ⁇ , anti-AFP- ⁇ and 10 mg of anti-PSA- ⁇ monoclonal antibody, adjust the volume to 1 ml with PH9.5 buffer solution, add the above activated ABEI solution, and mix. After that, it was reacted at room temperature for 20 h, and purified by a G-25 gel column; 2, FITC labeled CEA, AFP, PSA monoclonal antibody
  • the preparation of the nano magnetic microbeads is prepared according to the Chinese patent, and the patent number is CN92105584. 6.
  • the surface of the magnetic beads is a group containing -NH 2 , and its content is 0.17 eq/g; 10 ml magnetic beads are obtained, and the concentration is 30 mg/
  • the glutaraldehyde concentration is 0. 01-, and the glutaraldehyde solution is added to a solution of 10% glutaraldehyde in a PBS solution. 0. 01MPH7. 4 PBS, 0. 01- 1% BSA was added to the supernatant. The 5% of NaN 3 is added.
  • Table 1 4 # and 6 # patients are primary early stage liver cancer patients, AFP values continue to increase for a long time, 1 1 # and 1 4 # for liver cancer resection and in patients with radiotherapy and chemotherapy, the serum AFP concentration has decreased, but Still did not fall to the normal range, suggesting that the efficacy is not obvious, there is still the possibility of turning evil; 2 # , 8 # and 6 # patients' AFP value also exceeds the normal value, but the clinical diagnosis is rectal cancer, its CEA value is significantly higher, In particular, 16 # and CEA are as high as 1270 mIU/ml, which may indicate that there is a certain relationship or cross between different tumor markers.
  • the 1 # and 8 # patients are prostate and simple prostatic hypertrophy, respectively, and their PSA values are slightly elevated.
  • Example 2 Preparation of Isoluminol Derivative Monoclonal Antibody and Preparation of Nanomagnetic Bead Surface Coated Sheep Anti-FITC Polyclonal Antibody The same procedure as in Example 1 was used.
  • the luminescent label used in this example was AHEI, magnetic beads. The surface is 0. 3eq/g;
  • TSH, T3, T4, FT3 and FT4 standards were taken separately. Serum samples were 20 ⁇ l each, and ⁇ and FITC monoclonal antibodies were added to the luminescent label monoclonal antibody and 40 ⁇ l each, and then mixed at 37 ° C.
  • TDH values were significantly increased in 37 patients with hypothyroidism, and T3, T4, T3, T4, FT3, and FT4 were significantly lower, which was consistent with clinical diagnosis.
  • TSH was significantly decreased
  • T3, T4, FT3, and FT4 were significantly increased.
  • Statistical analysis of five mutations in 26 patients with hyperthyroidism in treatment showed that T4 values all recovered or were close to normal values. , T3, the rate of decline is significantly slower than the T4 value, the results obtained by the magnetic luminescence immunoassay test method described in the present invention have a good clinical consistency.
  • the test items of the reagents according to the examples of the present invention are exemplified by the determination of thyroid hormones and tumor markers, but the present invention is not limited to testing both items.
  • Industrial applicability The magnetic separation direct chemiluminescence analysis method of the invention adopts an isoluminol derivative as a luminescent label, completely overcomes the defect of easy hydrolysis of the traditional acridinium ester, and as a direct chemiluminescence mode, not only the analysis speed is fast, but also close to the whole 180 tests/hour of automatic direct chemiluminescence completely avoids the defect that the enzyme activity of enzymatic luminescence is easy to decrease; using nano-immunomagnetic microbeads as a carrier for antibodies and an isolation reagent for antigen-antibody immune complexes, greatly shortening the immune response Time, in which the time of isolation of the immune reaction is only 5 minutes, the entire immune reaction time is only 20 minutes, and the test results are highly accurate and high-precision; FITC

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  • Chemical & Material Sciences (AREA)
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Abstract

L'invention concerne un réactif de chimiluminescence directe pour séparation magnétique, et une méthode de dosage immunologique utilisant le réactif. Le réactif comprend: un dérivé d'isoluminol utilisé comme étiquette luminescente; des nanobilles immuno-magnétiques enrobées d'anticorps polyclonaux anti-FITC de caprin utilisés comme agents de séparation; NaOH et H2O2 utilisés comme substrats chimiluminescents. Le réactif est stable et non décomposable et n'est donc pas sensible aux facteurs du milieu. La méthode de dosage immunologique est rapide et très précise.
PCT/CN2007/001295 2006-04-21 2007-04-20 Réactif de chimiluminescence directe pour séparation magnétique, et méthode de dosage immunologique utilisant le réactif WO2007121668A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CNB2006100604488A CN100464189C (zh) 2006-04-21 2006-04-21 磁分离直接化学发光试剂及用该试剂的测试方法
CN200610060448.8 2006-04-21

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