WO2008146966A1 - Kits et procédés de détection biologique utilisant des points quantiques - Google Patents

Kits et procédés de détection biologique utilisant des points quantiques Download PDF

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Publication number
WO2008146966A1
WO2008146966A1 PCT/KR2007/002748 KR2007002748W WO2008146966A1 WO 2008146966 A1 WO2008146966 A1 WO 2008146966A1 KR 2007002748 W KR2007002748 W KR 2007002748W WO 2008146966 A1 WO2008146966 A1 WO 2008146966A1
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Prior art keywords
qds
oxidase
bioconjugate
glucose
mpa
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PCT/KR2007/002748
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English (en)
Inventor
Jong Il Rhee
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Industry Foundation Of Chonnam National University
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Publication of WO2008146966A1 publication Critical patent/WO2008146966A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
    • C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
    • C12Q1/26—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving oxidoreductase
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y15/00—Nanotechnology for interacting, sensing or actuating, e.g. quantum dots as markers in protein assays or molecular motors
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
    • C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
    • C12Q1/26—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving oxidoreductase
    • C12Q1/28—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving oxidoreductase involving peroxidase
    • 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
    • G01N33/533—Production of labelled immunochemicals with fluorescent label
    • 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
    • G01N33/588—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances with semiconductor nanocrystal label, e.g. quantum dots

Definitions

  • the present invention relates to the biological detection
  • the present invention relates to bioconjugates of QDs having CdSe core and
  • QDs consisting of CdSe core and ZnS shell are spherical materials having a diameter of several to tens of nanometers .
  • QDs have a property of emitting fluorescence at different wavelengths depending on their 0 particle sizes, and thus, they can be used not only for basic biology such as cell biology but also for applied biology including various protein chips and biosensors, etc.
  • QDs can be excited by light of any wavelength ranging from UV to red and have a controllable narrow emission spectrum. They are inorganic, and so stable against chemical reactions and can be easily linked with biological materials through a surface treatment. Jaiswal et al . reported that avidin-conjugated QDs were linked with a biotinylated primary antibody and the resulting QD bioconjugates were used to image live cells
  • QDs have a high photo-stability and allow for continuous real-time monitoring, and thus, are attractive materials in the field of biosensors.
  • the application of QDs in this field is still limited because the photoluminescence quantum yield of the QDs decreases significantly when they are transformed from the hydrophobic to hydrophilic form or when they are conjugated with other materials.
  • Recently, researches have been focused on the development of sensors for some target analytes, wherein QDs are used as electron donors for fluorescence resonance energy transfer (FRET) between the QDs (donor) and an acceptor molecule.
  • FRET fluorescence resonance energy transfer
  • many advantageous properties of QDs have been exploited for the development of sensors based on the change in the emission wavelength, voltage or fluorescence intensity.
  • Glucose is an important nutrient source for microorganisms in biotechnological processes.
  • the measurement of glucose concentration is always useful in controlling various food and biotechnological processes, as well as in diagnosing many metabolic disorders, especially in the diagnosis and therapy of diabetes.
  • Many methods have been used for the detection of glucose, but none of the methods developed so far have used QDs for glucose detection.
  • the present inventors have performed extensive studies for efficient application of QDs consisting of CdSe core and ZnS shell to biosensors. As a result, the inventors found that bioconjugates of QDs and various oxidases, which are obtained by coating QDs with a hydrophilic surfactant, and then, conjugating the coated QDs with the oxidases, can be efficiently used for the detection of many biological materials including monosaccharides, polysaccharides, organic acids, etc., and therefore, completed the present invention.
  • the first object of the present invention is to provide QDs-oxidase bioconjugates .
  • the second object of the present invention is to provide sensing membranes onto which said bioconjugates are immobilized .
  • the third object of the present invention is to provide biological detection kits comprising said membranes.
  • the fourth object of the present invention is to provide methods for biological detection using said detection kits.
  • the first aspect of the present invention relates to a bioconjugate, in which a QD having CdSe core and ZnS shell is coated with a hydrophilic surfactant, and the coated QD is conjugated with an oxidase.
  • said oxidase is selected from the group consisting of glucose oxidase (GOD) , lactate oxidase (LOD) , tyramine oxiade (TOD) , cholesterol oxidase, choline oxidase, alcohol oxidase, ascorbic acid oxidase, and xanthine oxidase.
  • Said hydrophilic surfactant is preferably mercaptopropionic acid (MPA) , mercaptoacetic acid (MAA) , mercaptosuccinic acid (MSA) , dithiothreitol (DTT) , glutathione, histidine or thiol- containing silane.
  • Bioconjugate of the present invention can be further conjugated to peroxidase, particularly to horseradish peroxidase (HRP) .
  • the second aspect of the present invention relates to a sensing membrane onto which said bioconjugate is immobilized.
  • the immobilization may be performed by a sol-gel method.
  • the third aspect of the present invention relates to a biological detection kit comprising said bioconjugate or said
  • the kit of the present invention may be used for detection of a substance selected from the group consisting of monosaccharides, polysaccharides, organic acids, alcohols, cholesterol, choline, xanthine, and mixtures thereof.
  • the kit of the present invention may have the bioconjugate or the
  • the fourth object of the present invention relates to a method for biological detection comprising the steps of;
  • said reaction is preferably carried out in the presence of Fe 3+ ions .
  • Fluorescence intensity may be measured by an optical method or by converting it to an electrical signal.
  • the present invention relates to the detection of biological materials using CdSe/ZnS core-shell QDs.
  • hydrophilic CdSe/ZnS core-shell QDs are hydrophilic CdSe/ZnS core-shell QDs
  • the fluorescence quenching of the QDs is used to measure the fluorescence
  • the quenching process is based on the transfer of electrons from the QDs to enzymes including glucose oxidase (GOD) and horseradish peroxidase (HRP) , which catalyze the oxidation/reduction reactions of glucose.
  • the QDs are able to be used to detect
  • FIG. 1 depicts the reaction scheme of glucose oxidation to gluconic acid using GOD/HRP conjugated to CdSe/ZnS QDs.
  • glucose is detected by measuring a change in fluorescence intensity by the above chemical modification.
  • any detection method known in the art may be used, and examples thereof include, but are not limited to, optical methods and other methods involving conversion into electrical signals.
  • CdSe/ZnS core-shell QDs that are used in the present invention are synthesized using a modified version of the conventional synthetic method, and they can be coated with a hydrophilic surfactant (for example, MPA, MAA, MSA, DTT, glutathione, histidine, thiol-comprising silane, etc.).
  • a hydrophilic surfactant for example, MPA, MAA, MSA, DTT, glutathione, histidine, thiol-comprising silane, etc.
  • examples of the enzyme include, but are not limited to, glucose oxidase (GOD) , lactate oxidase (LOD) , tyramine oxiade (TOD), cholesterol oxidase, choline oxidase, alcohol
  • said enzyme-QDs can be immobilized onto a sol-gel layer containing 3-glicydoxypropyl-trimethoxysilane
  • sol-gel which is used for immobilization of enzymes or encapsulation of organic T) materials and biomaterials , contribute significantly to the stability and sensitivity of the membranes for detection of the biological materials.
  • Mixing ratio of silane in sol-gel results in different properties including different response rates of sensing membranes for measurement of biological
  • GPTMS and MTES are used preferably in the volume ratio of 1:1-2, particularly of 1:2.
  • GPTMS and APTMS are used preferably in the volume ratio of 2-4:1, particularly of 4:1. Therefore, for example, the
  • IT) sensing membranes comprise QDs, which are immobilized onto sol-gel comprising GPTMS and MTES in the volume ratio of 1:1-2, particularly of 1:2, and the enzymes, which are immobilized onto sol-gel comprising GPTMS and GPTMS in the volume ratio of 2-4:1, particularly of
  • said bioconjugates or sensing membranes can be formed on a substrate to manufacture a biological detection kit.
  • a substrate any ones known in the art can be chosen and used. Examples thereof include, but are not specially limited to, a glass plate, a polystyrene plate, a microtiter plate, etc.
  • Figure 1 depicts the reaction scheme of glucose oxidation to gluconic acid using GOD/HRP conjugated to CdSe/ZnS QDs;
  • Figure 2 shows absorption spectra of CdSe (550 nni) , CZ-QDs (580 nni) and MPA-QDs (580 urn),
  • Figure 2 (b) shows emission spectra of CdSe (560 nni) , CZ-QDs (590 nm) and MPA- i ⁇ QDs (590 nni ) at excitation wavelength of 480 nm
  • Figure 2 (c) shows the overlap of absorption and emission spectra of the enzymes (GOD, HRP) and QDs
  • Figure 2 (d) shows the image of CdSe (left) and CdSe/ZnS (right) under UV light;
  • Figure 3 (a) is a photo image of gel electrophoresis of
  • Figure 5 shows change in fluorescence intensities of the QD-FRET-based probe at different glucose concentrations and various volume ratios of QDs/GOD/HRP added to glucose solution;
  • Figure 6 shows effect of pH and temperature of reaction solution during glucose measurements; and, Figure 7 shows effect of Fe 3+ ions on the fluorescence emission of MPA-QDs during the measurement of glucose solution
  • CdSe/ZnS core-shell QDs were based on a modified version of the existing method. Firstly, CdSe nanoparticles were synthesized using a modified version of the methods m L. Qu, X. Peng, J. Am. Chem. Soc . 124 (2002) 2049- 2051, and J. A. Gaunt et al . , J. Coll. Interf . Sci. 290 (2005). Cadmium acetate dehydrate (0.6 mM, 147 mg) and stearic acid (2.13 mM, 607 mg) were loaded into a 50 mi three-neck flask, and the mixture was heated to 150 ° C under vacuum conditions until a colorless liquid was obtained.
  • hexadecylamme (1.94 g) and trioctylphosphme oxide (TOPO; 2.2 g) were added to the flask.
  • the mixture was then degassed using a pump and heated at 120-150 ° C under
  • reaction vessel was then filled with nitrogen gas and heated to 310-320 ° C , and at this point, a solution of selenium (211 g) m trioctylphosphme (TOP; 2.5 ml-) was rapidly injected into the vigorously stirred reaction mixture. The solution was heated for 25 seconds before removing the flask i r ) from the heating mantle and then allowing it to cool to room temperature. The resulting CdSe nanoparticles were purified by dissolving the reaction mixture in chloroform, followed by precipitation with an equal volume of methanol.
  • TOP trioctylphosphme
  • these purified CdSe particles were used to synthesize 0 the CdSe/ZnS core-shell QDs (CZ-QDs) .
  • a mixture of hexadecylamme (2 g) and TOPO (2.5 g) was loaded into a 50 mf three-neck flask. The mixture was degassed and heated to 180 V. At 180 ° C , the purified CdSe particles dispersed m chloroform (2 ml) were added to this solution. After chloroform was completely pumped out, the flask was filled with nitrogen gas. The temperature of the reaction then increased to 180-185 ° C .
  • Example 1 Synthesis of bioconjugates of MPA-coated CdSe/ZnS 5 core- shell QDs and oxidases
  • Example 2 Optical characterization of QDs
  • the absorption and emission spectra of CdSe nanoparticles, MPA-QDs and enzyme-conjugated MPA-QDs were determined using a Multiskan spectrum (Thermo electron corporation, Finland) and Fluorescence spectrophotometer (Model: F-4500, Hitachi Co., r> Japan), respectively.
  • the synthesized CdSe/ZnS core-shell QDs had a high fluorescence intensity with a quantum yield (QY) of 64% and their particle size ranged from 2 nm to 4.5 lira.
  • Figure 2 (a) shows the absorption spectra of the CdSe particles, CZ-QDs and
  • MPA-QDs was 590 nm with a FWHM (full width at half maximum for emission spectrum) of 40 nm, which overlapped with the absorption band of GOD and HRP (see Figure 2(c)). This property was exploited in order to utilize the QDs for glucose 0 sensing via the electron transfer from the QDs to the enzymes.
  • the quantum yield of the QDs after converting the carboxyl groups (MPA) on their surface was decreased to about 50% of its initial value.
  • the amine groups of the enzymes are easily bound to the carboxyl groups located on the surface of QDs.
  • the sizes of the QD increased after their conjugation with the enzymes, and increasing the amount of GOD i .1 resulted in an increase in the amount of the enzymes bound to the binding sites of the QD surface (see Figure 3 (a) ) .
  • Their movement in the gel plate was slower than that of the enzyme- conjugated MPA-QDs (Enz-QDs) containing a larger amount of enzymes and, therefore, their migration distances in the gel 0 were slightly shorter than those of the MPA-QDs comprising a smaller amount of GOD.
  • Figure 3 (a) shows the fluorophore quenching of the QDs at an emission wavelength of 590 nm when the amount of GOD is increased.
  • the enzymes were able to receive energy from the excited QDs, resulting in an increase in their fluorescence intensity.
  • GOD a structurally rigid glycoprotein of 160,000 Da, has a hydrodynamic radius of 43 A and consists of two identical polypeptide chains.
  • the rigidity and ruggedness of GOD are derived from the polysaccharide that forms its outer hydrophilic envelope.
  • the electrons are transferred between the redox enzyme and the electrochemically reduced form of H 2 O 2 , which is generated upon the 0 2 -biocatlayzed oxidation of glucose, the turnover rate of the electron exchange between the substrates (e.g., glucose, H 2 O 2 or O 2 ) and the biocatalysts (including GOD and HRP) , as well as between the QDs and enzymes, is rapidly increased.
  • the transduced physical energy of the QDs associated with the quenched fluorophores reflects the substrate concentration in the system.
  • the fluorescence emission of the enzymes and their activities were considerably changed after their conjugation with the MPA-QDs.
  • the fluorescence intensity (Excitation: 445 ran/ Emission: 525 ran) increased to about 30% or 43% of its original value, respectively.
  • the fluorescence intensity of GOD decreased rapidly to about 20% or 41% of its original value, respectively.
  • Glucose was measured using a mixture of MPA-QDs, GOD and HRP.
  • the enzymes (GOD, HRP) and MPA-QDs were added to the wells of a microtiter plate which included 100 j ⁇ . of various concentrations of glucose solution. Mixtures of the MPA-QDs,
  • the pathway of electron transfer from the excited QDs to the H 2 O 2 reduction reaction was depressed or i F) prevented. Therefore, a decrease of the electron numbers resulted in a decrease of the turnover rate of the electron exchange, reflecting the lower photoluminescence quenching of the QDs and lower sensitivity to glucose.
  • Sensing membranes were prepared using a sol-gel method, m accordance with the method described in Korean Patent Application No. 10-2007-0050538. Specifically, a mixture (GM2)
  • sol-gel IT comprising GPTMS and MTES in the volume ratio of 1:2
  • G2 a mixture
  • GPTMS and APTMS in the volume ratio of 4:1 were mixed in 99% ethanol, respectively, to give sol- gel.
  • 35% HCl was added at the volume of 40 ⁇ t/ml. After the addition of HCl, the resulting sol-gel 0 was stored at room temperature for at least two hours prior to use in the next step.
  • the MPA-coated QDs of 50 j ⁇ synthesized in Preparation Example 2 was added to the sol-gel GM2 of 200 [ ⁇ to give a transducer. After completely mixing the MPA-coated QDs and the sol-gel by mechanical stirring, the mixture was stored at room temperature for two hours. 5 ⁇ i of the MPA-coated QDs mixture was injected into the bottom of a 96-well microtiter plate, and then, dried at 95 ° C for 18 hours. After the heat 5 treatment, the sol-gel GA2 was added onto the transducer, on which 40 fd of the enzyme solution (GOD: 100 unit, LOD: 1 unit, or TOD: 0.005 unit) was added to the well of 96-well microtiter plate. The enzymes were immobilized at room temperature for 18 hours.
  • the effects of pH and temperature on the glucose sensing were investigated by using a mixture of GOD, HRP and MPA-QDs.
  • the universal buffer used in this example contained 0.1 M i.) Na 2 SO 4, 0.04 M NaOAc, 0.04 M H 3 BO 3 and 0.04 M NaH 2 PO 4 , whose pH was adjusted with 3 N NaOH and 3 M HCl, and measured using a pH meter (Metrohm Co., Switzerland) to obtain the pH range of 4-11. 100 ⁇ l of glucose solution (1 g/ I ) prepared in universal buffer at a given pH and 20 ⁇ jt of the mixture of GOD, HRP and O MPA-QDs were introduced into a well of a microtiter plate and then the fluorescence intensity was measured.
  • 120 j ⁇ of the reaction mixture solution at a glucose concentration of 1.0 g/ I in the well was incubated at temperatures between 23 ° C and 37 ° C , and the fluorescence intensity was then measured at an excitation/emission wavelength of 485/525 ran .
  • the temperature and pH had only a r> slight effect on the glucose measurement of the present invention.
  • the change in the fluorescence intensity was different at low (i.e., 4-5) or high (i.e., 11) pH .
  • the fluorescence intensity at low or high pH seems to be higher than that at neutral pH, in practice the QD
  • Ti range of the ions was from 0.01 to 200 mM. 100 ⁇ l of the ion solution was added to a well of a microtiter plate and then mixed with 10 g/ i glucose to obtain a final glucose concentration of 1 g/ t . Each solution of ions at the different concentrations was prepared on a microtiter plate in
  • the fluorescence emission of the MPA-QDs was quenched at an Fe Jf ion concentration of 0.1 mM and absolutely quenched at higher concentrations (>0.5 mM) (see Figure 7).
  • the fluorescence intensity of the MPA-QDs decreased at low concentrations of Fe 3+ (0.5 mM and 1.0 mM) .
  • the Fe 3+ ion acts as a mediator, which has appropriate oxidation potentials, to replace oxygen in the glucose T) oxidation. Therefore, the response of the signal after adding the enzymes was too fast and tenfold higher fluorescence intensity was observed at high concentrations of Fe 3+ .
  • CdSe/ZnS core-shell QDs that have been coated with a hydrophilic surfactant can be conjugated with oxidases.
  • the bioconjugates of the present invention have the property of energy transfer between neighboring molecules, and thus, can be widely used in the

Abstract

L'invention concerne des conjugués biologiques de points quantiques qui comprennent un noyau CdSe et une enveloppe ZnS et diverses oxydases, des membranes de détection sur lesquelles lesdits conjugués biologiques sont immobilisés, des kits de détection biologique qui comprennent lesdites membranes de détection et des procédés de détection biologique qui utilisent lesdits kits de détection. Les points quantiques présentent plusieurs avantages par rapport aux fluorophores organiques et peuvent donc être utilisés pour la détection de monosaccharides, de polysaccharides, d'acides organiques, etc. et notamment pour la détection du glucose sur une large plage de concentration.
PCT/KR2007/002748 2007-05-28 2007-06-07 Kits et procédés de détection biologique utilisant des points quantiques WO2008146966A1 (fr)

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CN104215617A (zh) * 2014-09-13 2014-12-17 福建医科大学 基于金纳米团簇的脲酶活性荧光测定方法
CN109239041A (zh) * 2018-10-22 2019-01-18 天津科技大学 一种用于检测酪胺的碳点-分子印迹聚合物试纸条及其制备方法和应用
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