WO2017155172A1 - Composite de point de carbone-hémoglobine pour la détection du cholestérol - Google Patents

Composite de point de carbone-hémoglobine pour la détection du cholestérol Download PDF

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WO2017155172A1
WO2017155172A1 PCT/KR2016/009440 KR2016009440W WO2017155172A1 WO 2017155172 A1 WO2017155172 A1 WO 2017155172A1 KR 2016009440 W KR2016009440 W KR 2016009440W WO 2017155172 A1 WO2017155172 A1 WO 2017155172A1
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cholesterol
hemoglobin
carbon
cds
fluorescence
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Korean (ko)
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박수영
부이티트랑
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경북대학교 산학협력단
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    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
    • G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
    • G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
    • G01N21/64—Fluorescence; Phosphorescence
    • 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
    • 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
    • G01N33/72—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving blood pigments, e.g. haemoglobin, bilirubin or other porphyrins; involving occult blood
    • 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
    • G01N33/92—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving lipids, e.g. cholesterol, lipoproteins, or their receptors

Definitions

  • the present invention relates to a carbon point-hemoglobin complex for cholesterol detection.
  • Cholesterol is a fat produced in the liver and is distributed throughout the body. It is a precursor of steroid hormones, vitamin D, and bile, and as an important component of cell membranes, in the human body, the equilibrium properties of cholesterol are important. If the amount of cholesterol exceeds the appropriate level, the blood vessels are damaged. This can lead to cardiovascular disease.
  • Analytical methods for detecting cholesterol include electrochemical methods, thin layer chromatography and high performance liquid chromatography (HPLC). However, these methods have disadvantages such as complicated procedures, slow reaction time, low selectivity and specificity. And most cholesterol sensors use cholesterol oxidants. This is expensive and has the disadvantage of easy denaturation.
  • hemoglobin is an important protein in red blood cells that carry oxygen throughout the body. It is rough spherical, has a diameter of 5.5 nm, has a molecular weight of 68,000 and contains four polypeptide chains. Each chain is bound to four Heme prosthetic groups consisting of tetrapyrrole rings chelated to Fe 2+ ions.
  • Carbon dots are carbon nanomaterials with a high fluorescence intensity and sizes of less than 10 nm, and have a chemical group on their edges and surfaces. It has the characteristics of biocompatibility, easy synthesis, non-toxicity and environmental friendliness. Therefore, these characteristics are used for biosensors and drug delivery.
  • carbon dots may have "off-on" fluorescence because of their surface structure and function. That is, when bio-compound and metal ions including a conjugate system are absorbed on the surface of the carbon spot through van der Waals bonding and chelation, the fluorescence is quenched and the fluorescence is "off", and the analyte and the metal ion If a bond is formed between them, the fluorescence is restored.
  • Zeng et al. Reported that DNA can be determined after quenching the carbon point of fluorescence and the methylene blue solution.
  • cholesterol detection based on "off-on" fluorescence using carbon dots and hemoglobin.
  • the present inventors confirmed that cholesterol can be detected by carbon point and hemoglobin through the quenching-enhance approach of carbon point fluorescence and completed the present invention.
  • the present invention is to provide a carbon point-hemoglobin complex for cholesterol detection as a technical problem.
  • the present invention is to provide a composition for detecting cholesterol comprising the carbon point-hemoglobin complex for detecting cholesterol as another problem.
  • the present invention to solve the above problems,
  • a carbon dot and a hemoglobin chelate bound to the carbon dot surface A carbon dot and a hemoglobin chelate bound to the carbon dot surface
  • carbon point-hemoglobin complexes for cholesterol detection Provided are carbon point-hemoglobin complexes for cholesterol detection.
  • composition for detecting cholesterol comprising the carbon point-hemoglobin complex.
  • optical cholesterol sensor comprising the carbon point-hemoglobin complex.
  • the carbon point-hemoglobin complex of the present invention can exhibit high selectivity for cholesterol and high detection sensitivity and fast reaction time, thereby having an effect of detecting cholesterol.
  • according to the present invention can provide a biosensor capable of detecting cholesterol simply and economically, in particular, there is an effect that can provide a biosensor capable of medical applications.
  • FIG. 1 schematically shows the fluorescence principle of the carbon point-hemoglobin complex for cholesterol detection according to the present invention.
  • FIG. 2 shows the results of the dynamic light scattering (DLS) of the carbon dots according to an embodiment of the present invention.
  • Figure 3 shows the analysis results of the carbon point according to an embodiment of the present invention
  • Figure 3a is an FT-IR spectrum
  • Figure 3b is a UV-vis spectrum for absorption, excitation-emission of the carbon point
  • Figures 3c and 3d Shows the analysis results by photoluminescence spectroscopy of carbon dots.
  • FIG. 4 is a carbon point according to an embodiment of the present invention, and other metal ions (Cu 2+ , Mg 2+ , Na + , Fe 2+ , Fe 3+ ) or bio compound (Hb, Lys, Glu, Vit. C, Urea), where F0 and F are the fluorescence intensity of the carbon point before and after adding each substance.
  • other metal ions Cu 2+ , Mg 2+ , Na + , Fe 2+ , Fe 3+
  • bio compound Hb, Lys, Glu, Vit. C, Urea
  • Figure 5 shows the analysis results according to the photoluminescence spectroscopy method of (a) carbon dots (CDs) according to an embodiment of the present invention, (b) a: CDs, b: CDs and Hb, c: CDs under ultraviolet light, respectively; / Hb shows a cholesterol solution, and (c) shows the selectivity of CDs / Hb of cholesterol and different biomolecules (urea, glucose, galactose and L-ascorbic) at the same concentration (F0 and F is the fluorescence intensity of CDs / Hb before and after adding each substance).
  • CDs carbon dots
  • FIG 6 shows the relative fluorescence intensity of the carbon point according to the concentration of hemoglobin, according to an embodiment of the present invention, wherein F0 is the fluorescence intensity of the carbon point solution before hemoglobin addition, F is the carbon point solution of the hemoglobin addition Fluorescence intensity)
  • Figure 7 shows the effect of the reaction time on the fluorescence intensity of the CDs / Hb system according to an embodiment of the present invention.
  • Figure 8 shows the fluorescence intensity according to the reaction time of the CDs / Hb / Cho system according to an embodiment of the present invention.
  • Figure 9 shows the fluorescence effect according to the pH of the CDs / Hb / Cho system according to an embodiment of the present invention (F0 is the fluorescence intensity of the CDs / Hb solution before cholesterol addition, F is the CDs / Hb after cholesterol addition Fluorescence intensity of the solution).
  • FIG. 10 shows cholesterol detection characteristics according to an embodiment of the present invention
  • FIG. 10A shows a PL spectrum of a CDs / Hb solution under different concentrations of cholesterol
  • FIG. 10B shows a fluorescence intensity of a CDs / Hb / Cho solution.
  • F0 is the strength of the CDs / Hb solution before cholesterol addition
  • F is the strength of the CDs / Hb solution after cholesterol addition.
  • the present invention includes a carbon dot and hemoglobin chelate-bonded to the surface of the carbon dot, and the fluorescence of the carbon dot is quenched by the binding of the hemoglobin and reacts with cholesterol to react with the carbon.
  • a carbon point-hemoglobin complex characterized in that the fluorescence of a point is enhanced to detect cholesterol.
  • the present invention detects cholesterol by the carbon point and hemoglobin through “quenching-enhance” (off-on) of the carbon point fluorescence.
  • quenching of carbon point fluorescence is formed by the presence of hemoglobin in the carbon point solution, fluorescence of the carbon point is off, and “enhance” is formed by adding cholesterol thereto, and carbon points (CDs) To restore the fluorescence of (on).
  • hemoglobin (Hb) may be detected from 0 to 14 ⁇ M in the fluorescence disappearance process, and 56 to 800 ⁇ M of cholesterol may be detected in the recovery process of the fluorescence.
  • the cholesterol detection time according to the recovery of the fluorescence of the carbon point is 1 to 5 minutes, according to an embodiment of the present invention, the fluorescence emission balance of the carbon point-hemoglobin complex was 1 minute and 30 seconds.
  • the carbon point-hemoglobin complex of the present invention exhibits high selectivity to cholesterol, high detection sensitivity, and fast reaction time.
  • the present invention relates to a composition for detecting cholesterol including the carbon point-hemoglobin complex. .
  • the carbon point-hemoglobin complex of the present invention can detect cholesterol using quenching and recovery of fluorescence.
  • the present invention relates to an optical cholesterol sensor including the carbon point-hemoglobin complex.
  • Carbon dots are a well-known method ( Shoujun Zhu et al., Highly Photoluminescent Carbon Dots for Multicolor Patterning, Sensors, and Bioimaging, Angewandte Chemie International Edition, Volume 52, Issue 14, pages 3953-3957, April 2, 2013.) It was prepared by. Specifically, 0.4 g citric acid (CA) and 270 ⁇ l ethylenediamine (EDA) are dissolved in 80 ml of deionized water, and then the solution is placed in an autoclave and heated at 200 ° C. for 4 hours. In addition, carbon point synthesis was carried out by hydrothermal carbonization reaction. After this reaction, the reactor was naturally cooled to room temperature by water to obtain a transparent reaction product having a brown-red color. Next, carbon dots (CDs) were finally obtained using dialysis. The concentration of the finally obtained CDs solution is approximately 6.13 mg / ml.
  • the obtained CDs solution was diluted in distilled water to a concentration of 0.02 mg / ml. Then, to detect hemoglobin, hemoglobin was added to the CDs solution by concentration (50 ⁇ L, 0.02 mg / ml).
  • the fluorescence intensity was measured in an excited state of 380 nm using a fluorescence spectrophotometer.
  • the selectivity of hemoglobin detection was also tested through the addition of 8 ⁇ M of other metal ions and biocompounds at the same concentration.
  • urea glucose, galactose, L-ascorbic and cholesterol were added to the hemoglobin solution.
  • CDs Carbon Points
  • Figure 2 shows the results of the DLS, it can be seen that the size of the carbon spot is about 1.5-2nm.
  • FIG. 3a is a reference when it shows an FT-IR absorption peak at 2935-2868cm -1 result indicates a antisym and symstretching of CH, 679cm -1 is a peak bending motion of the CH (bending out-of-plane deformation)
  • the carbon dots (CDs) are small in size and have a multifunction group on the surface, they are highly compatible with conjugate compounds and have high solubility with various hydrophilic solvents.
  • the analysis was performed by using UV / vis spectroscopy and photoluminescence spectroscopy.
  • FIG. 3B shows a UV / vis spectrum.
  • the carbon point solution is transparent in normal white light but blue in the ultraviolet region of 365 nm, shows a center peak at 210 nm and 340 nm, and a shoulder peak at 250 nm.
  • 3C and 3D show the results of an analysis according to photoluminescence spectroscopy of carbon dots.
  • a wide color band from blue to yellow-green for different excitation wavelengths is shown. (color band) is shown. It is clear from this that the carbon dots are called multi-colors and can be used for cell labeling, bioimaging, and so on.
  • Figure 4 also shows the selectivity for carbon points and other metal ions (Cu 2+ , Mg 2+ , Na + , Fe 2+ , Fe 3+ ) or biocompounds (Hb, Lys, Glu, Vit.C, Urea). As shown, it was confirmed that the carbon point shows high selectivity for binding to hemoglobin in other metal ions or bio compounds.
  • Figure 5 shows the results of the analysis according to the photoluminescence spectroscopy of (a) carbon dots (CDs), (b) each containing a: CDs, b: CDs and Hb, c: CDs / Hb under ultraviolet light Cholesterol solution, and (c) selectivity of CDs / Hb of cholesterol and different biomolecules (urea, glucose, galactose and L-ascorbic) at the same concentration.
  • CDs carbon dots
  • b each containing a: CDs, b: CDs and Hb
  • c CDs / Hb under ultraviolet light Cholesterol solution
  • selectivity of CDs / Hb of cholesterol and different biomolecules urea, glucose, galactose and L-ascorbic
  • (b) shows the fluorescence changes according to different conditions (CDs, CDs and Hb, CDs / Hb and cholesterol (Cho)). Specifically, CDs and CDs / Cho showed almost similarly high fluorescence, and Hb / Cho showed little fluorescence. In addition, CDs / Hb / Cho showed stronger fluorescence than CDs / Hb, and it was confirmed that the fluorescence intensity increased after adding cholesterol to the CDs / Hb complex.
  • the fluorescence intensity decreases to about 25% of the CDs / Hb complex than the original CDs solution (CDs / Cho), but in the case of cholesterol-linked CDs / Hb / Cho The fluorescence intensity was nearly doubled compared to the CDs / Hb complex fluorescence intensity, which is about 50% less than the original CDs solution.
  • the fluorescence of the carbon dots is quenched as the fluorescence of the carbon dots and the hemoglobin form a complex, and the complex is again bound with cholesterol to enhance fluorescence.
  • cholesterol is an amphiphilic substance with both -OH and alkyl chains, and these cholesterols interact with the iron of the hemoglobin heme group, and the hemoglobin polypeptide chains absorb the hydrophobic portion to the surface through hydrophobic interactions.
  • hemoglobin binds to cholesterol, thereby restoring the fluorescence of carbon dots.
  • the reason why the fluorescence intensity of the carbon spots increased after adding cholesterol to the CDs / Hb complex in FIG. 5 is that the CDs / Hb complex has a ⁇ - ⁇ stacking between the aromatic ring of the carbon spot and the heme group of hemoglobin. Van der Waals forces) because the complex of hemoglobin and cholesterol is thermodynamically more stable than the complex of hemoglobin and carbon points.
  • the energy of hydrophobic interaction is about 40 kJ / mol
  • the energy of van der Waals action is 0.4-4.0 kJ / mol
  • the energy of hydrophobic interaction is 10 times higher than van der Waals action, so that between cholesterol and hemoglobin
  • the carbon dots can be freely released from the hemoglobin complex and the fluorescence of the carbon dots can be recovered.
  • Figure 9 shows the fluorescence effect according to the pH of the CDs / Hb / Cho system, it showed an effect in the pH range of pH 6.2 ⁇ 7.8 is distilled water. Referring to this, it can be seen that the change between the pH 6.4-7.0 in the fluorescence recovery process is minimal, it was confirmed that distilled water can be used as a medium for the bio-sensing system.
  • FIG. 10 shows cholesterol detection characteristics based on the results of FIGS. 6 to 9.
  • FIG. 10A shows PL spectra according to wavelengths when cholesterol of different concentrations were dissolved in a CDs / Hb solution. Referring to this, it was confirmed that the fluorescence intensity gradually recovered as the concentration of cholesterol was increased.
  • Figure 10b shows the fluorescence intensity of the CDs / Hb / Cho solution as a recovery factor F / F0.
  • F and F0 are the fluorescence intensity of CDs / Hb according to the presence or absence of cholesterol at 450 nm, and the logarithm of the fluorescence recovery factor F / F0 is
  • the carbon point-hemoglobin complex of the present invention was confirmed that the high selectivity for cholesterol, high detection sensitivity, fast response time, and can be applied as a simple and economical biosensor, successfully detecting cholesterol in human serum It could be confirmed. It is believed that this invention may contribute to the application of carbon dots, including the study of optical cholesterol sensors, and may be applicable to cell labeling, bioimaging, and printing.

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Abstract

La présente invention concerne un composite de point de carbone-hémoglobine pour la détection du cholestérol. Spécifiquement, selon la présente invention, l'invention concerne un composite point de carbone-hémoglobine pour la détection du cholestérol, le composite comprenant : des points de carbone ; et de l'hémoglobine liée par chélate à des surfaces des points de carbone, la fluorescence des points de carbone étant limitée par la conjugaison avec l'hémoglobine, et la fluorescence des points de carbone étant améliorée par la réaction avec le cholestérol, ce qui permet de détecter le cholestérol.
PCT/KR2016/009440 2016-03-11 2016-08-25 Composite de point de carbone-hémoglobine pour la détection du cholestérol WO2017155172A1 (fr)

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Cited By (5)

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CN108414483A (zh) * 2018-02-28 2018-08-17 西华师范大学 一种用于多巴胺测定的荧光探针及其制备方法和应用
CN109897633A (zh) * 2019-03-20 2019-06-18 南宁师范大学 钴掺杂磁性碳量子点的制备方法及检测胆固醇的方法
CN111122531A (zh) * 2020-01-06 2020-05-08 闽南师范大学 一种可视化识别多种有机溶剂的比率荧光传感方法
CN113777088A (zh) * 2021-09-30 2021-12-10 湖北大学 一种基于碳点的乙酰胆碱酯酶的荧光检测方法
CN115381967A (zh) * 2022-08-05 2022-11-25 江南大学 一种用于感染成像及抗菌的碳点-铁血红素复合材料及其制备方法

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108414483A (zh) * 2018-02-28 2018-08-17 西华师范大学 一种用于多巴胺测定的荧光探针及其制备方法和应用
CN109897633A (zh) * 2019-03-20 2019-06-18 南宁师范大学 钴掺杂磁性碳量子点的制备方法及检测胆固醇的方法
CN109897633B (zh) * 2019-03-20 2022-04-08 南宁师范大学 钴掺杂磁性碳量子点的制备方法及检测胆固醇的方法
CN111122531A (zh) * 2020-01-06 2020-05-08 闽南师范大学 一种可视化识别多种有机溶剂的比率荧光传感方法
CN113777088A (zh) * 2021-09-30 2021-12-10 湖北大学 一种基于碳点的乙酰胆碱酯酶的荧光检测方法
CN113777088B (zh) * 2021-09-30 2023-08-29 马鞍山普梅森医学检验实验室有限公司 一种基于碳点的乙酰胆碱酯酶的荧光检测方法
CN115381967A (zh) * 2022-08-05 2022-11-25 江南大学 一种用于感染成像及抗菌的碳点-铁血红素复合材料及其制备方法
CN115381967B (zh) * 2022-08-05 2024-03-15 江南大学 一种用于感染成像及抗菌的碳点-铁血红素复合材料及其制备方法

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