KR101121513B1 - Method for selectively detecting Cysteine via Conjugated Fluorescent Polyelectrolyte-Mercury-Thymine Complexation - Google Patents
Method for selectively detecting Cysteine via Conjugated Fluorescent Polyelectrolyte-Mercury-Thymine Complexation Download PDFInfo
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Abstract
The present invention is based on the principle that the fluorescence color changes due to exciton transfer due to association of the water-soluble conjugated polymer compound having an ionic group, and the water-soluble conjugated compound prepared using mercury ions having a specific interaction with sulfur atoms and thymine. The present invention relates to a selective fluorescence detection method of cysteine in an aqueous solution using a polymer-mercury-thymine complex. It relates to a fluorescence sensor in which the fluorescence color of the compound changes.
Description
The present invention relates to a method for the selective detection of cysteine using a water-soluble conjugated polymer compound-mercury-thymine complex having an ionic group, and more particularly, to the principle that the fluorescence color changes due to exciton migration according to the association of the water-soluble conjugated polymer compound. And a selective fluorescence detection method of cysteine in aqueous solution using mercury ions interacting with sulfur atoms and thymine.
Biosensors are materials and analytical devices that have excellent selectivity and sensitive sensitivity to an object to be measured of an animal or a biological material, and are capable of converting physical and chemical signals due to any interaction into electrical signals. As a biosensor material, the water-soluble conjugated polymer has an advantage of signal amplification, which increases sensitivity when expressing a signal in response to interaction with the measured object, which is characteristic of the conjugated polymer, and is ionic. Interaction with biomaterials such as various ions, proteins, DNA, etc. with opposite charges is possible (DT McQuade, AE Pullen, TM Swager, Chem. Rev. 100, 2537, 2000; I.-B. Kim, JN Wilson , UHF Bunz, Chem. Commun. 1273, 2005).
Typical detection signals of biosensors using water-soluble conjugated polymers utilize electrical properties such as electricity, resistance, and potential difference, or optical properties such as color and fluorescence. Among them, the change of color and fluorescent color can be easily distinguished by the naked eye, so it is one of the easy methods to measure even without special equipment.
In the present invention, the measurement of the measured object was detected through the change in the fluorescent color by the association of the water-soluble conjugated polymer, and the change in the fluorescence due to the association is due to the structural characteristics in which the energy donor and the receiver are present in the same polymer sensor material. In the aqueous solution state in which the polymer is well dissolved, the energy donor and the acceptor are far from each other, so that only one-dimensional excitons in the molecule appear, but in the solid state, when the association occurs, the three-dimensional intermolecular excitons move as the energy donor and the acceptor get closer. Become active. As described above, the fluorescence changes as the exciton transfer phenomenon of the polymer changes in the solid state as compared to the aqueous state (A. Sartijo, TM Swager. J. Am. Chem. Soc. 129, 16020, 2007; F. Wang, GC Bazan, J. Am. Chem. Soc. 128, 15786, 2006).
In the present invention, mercury ions capable of specific binding are used as a method for inducing association of the water-soluble conjugated polymer. Mercury ions form complexes of thymine-mercury-thymine through selective binding to one of the DNA bases, thymine (JS Lee, HY Jun, JS Kim, Adv. Mater. 21, 1, 2009; JS Li, JJ Yao , WW Zhong, Chem, Commun., 4962, 2009), because they form strong bonds with sulfur atoms, they form complex compounds or desulfurize when reacted with sulfur-containing compounds (W. Shi, H. Ma, Chem. Commun., 1856 , 2008; XQ Zhan, ZH Qian, H. Zheng, BY Su, Z. Lan, JG Xu, Chem. Commun., 1859, 2008; YK Yang, KJ Yook, JS Tae, J. Am. Chem, Soc., 127, 16760, 2005). For this reason, it is possible to interact with cysteine, which is also a substance containing sulfur. Cysteine has a 2: 1 bond with mercury ions, which is stronger than the interaction with mercury-thymine (J. S. Lee, P. A. Ulmann, M. S. Han, C. A. Mirkin, Nano Lett., 8, 529, 2008)
Cysteine is a substance containing sulfur among the 20 basic amino acids and contains only thiol groups. In the body, cysteines form disulfide bonds, resulting in intramolecular crosslinking of proteins, affecting secondary structure and function. In particular, it is a constituent of nails, toenails, skin, and hair and is necessary for the production of collagen and to maintain the elasticity of the skin. As such, it is involved in the growth of cells or tissues, the lack of cysteine can lead to growth, hair discoloration, lethargy, skin lesions. In addition, since the thiol group has an oxidation-reduction reaction, cysteine has an antioxidant ability to affect human metabolism and detoxify. For this reason, they belong to a group of non-essential amino acids but are essential for people with certain metabolic disorders or malabsorption of sulfur.
Efforts to detect cysteine based on the binding properties of the metal ions and amino acids as described above have been attempted by low molecular weight and high molecular materials. Most of the cysteine detection methods studied are in organic solvents, not in aqueous phase, and thus are not suitable for practical environmental conditions and have limited applicability. The present invention proposes a method for detecting cysteine using a polymer-mercury-thymine complex by simplifying the conventional method for the introduction of a cysteine receptor into a polymer in an aqueous solution.
An object of the present invention is to provide a method for selectively detecting cysteine by forming a complex of a polymer compound-mercury-thymine using a water-soluble fluorescent conjugated polymer compound having an ionic group as a biosensor.
The present invention relates to a method for selectively fluorescently detecting cysteine in an aqueous solution using a water-soluble conjugated polymer compound having an ionic group, and a water-soluble conjugated polymer compound-mercury-thymine complex by interaction between mercury ions and thymine. More specifically, the present invention relates to a fluorescent sensor in which the water-soluble fluorescent conjugated polymer compound having an ionic group, mercury ions, and thymine form a complex to change the fluorescent color of the polymer compound according to the concentration of cysteine.
Hereinafter, the present invention will be described in detail.
The water-soluble conjugated polymer compound having the ionic group according to the present invention has a polymerization unit selected from the following formula (1) or (2).
[Formula 1]
[Formula 2]
[In Formula 1 or 2,
R 1 and R 2 are each independently a linear or branched C 1 to C 6 alkyl group substituted with sulfonate or tri (C 1 -C 7) alkylammonium salt at the end;
Ar 1 and Ar 2 are independently of each other (C6-C20) arylene;
a, b, c and d are mole fractions, a and c are independently from each other a real number of 0.05 to 0.5, b is 1-a and d is 1-c.]
Terminals of the alkyl groups of R 1 and R 2 may be independently substituted with one or more from, for example, sulfonate, trimethylammonium salt, ethyldimethylammonium salt, diethylmethylammonium salt or triethylammonium salt independently of each other, and R 1 And the alkyl groups of R 2 are, for example, independently of one another, methyl, ethyl, i-propyl, n-propyl, i-butyl, n-butyl, t-butyl, n-pentyl, i-pentyl or n-hexyl, Ar 1 and Ar 2 are, for example, divalent phenylene, but the present invention is not limited thereto.
The molecular weight of the water-soluble conjugated polymer according to the present invention is not limited in principle, but is preferably 3,000 to 100,000 as the number average molecular weight (Mn), and the range can be appropriately adjusted according to the characteristics required for the use thereof.
The water-soluble conjugated polymer compound represented by Chemical Formulas 1 to 2 of the present invention uses benzothiadiazole or bisthienylbenzothiadiazole as an energy acceptor, and phenylene as an energy donor. The change is characterized by different appearances. The water-soluble fluorescent conjugated polymer compound used in the present invention is described in Korean Patent Application No. 10-2008-0103701 filed by the present inventors, and the change in fluorescence due to association occurs by varying the type and ratio of the energy donor and the acceptor. Has characteristics.
In addition, the water-soluble conjugated polymer compound of the present invention exhibits only a blue fluorescence having a phenylene structure having a large energy band gap of 90% in the polymer compound in an aqueous solution state, whereas a small energy band of 10% occurs in association with a solid state. The movement of excitons to benzothiadiazole or bisthienylbenzothiadiazole having a gap is active, resulting in green or red fluorescence.
The water-soluble conjugated polymer compound has a selective bond with mercury ions because it is composed of benzothiazole or bisthienylbenzothiazole containing sulfur in the main chain. Mercury ions also form thymine-mercury-thymine complexes through coordination with thymine. When the water-soluble conjugated polymer, mercury, and thymine are reacted to form the water-soluble conjugated polymer-mercury-thymine-mercury-polymer complex using these two specific bindings, the association of the water-soluble conjugated polymer occurs. As a result, the blue-fluorescence high molecular compound dissolved in the aqueous solution causes a fluorescence change of green or red by association. The water-soluble conjugated polymer-mercury-thymine complex used in the present invention is described in Korean Patent Application No. 10-2010-0018607 filed by the inventor.
Water-soluble conjugated polymer-mercury-thymine complexes utilizing specific binding of mercury ions are useful for detecting cysteine. The mercury ions forming the complex have a very strong interaction with the cysteine's thiol, and the two cysteine molecules combine with one mercury ion. As a result, mercury ions that form the water-soluble conjugated polymer-mercury-thymine complex are combined with the cysteine to escape, and as a result, the association of the water-soluble conjugated polymer is disrupted. Through this process, the cysteine can be efficiently detected as the polymer compound, which has a green or red fluorescence by association, is dissolved again in an aqueous solution to show a change in the original blue fluorescence. That is, the polymer-mercury-thymine complex can selectively detect cysteine by causing fluorescence color change through non-association, and the detection is measured using a fluorophotometer.
As described above, the detection system based on the water-soluble fluorescent conjugated polymer-mercury-thymine complex having an ionic group according to the present invention can be used as a cognitive substance for cysteine, and in particular, cysteine is combined with the water-soluble fluorescent conjugated polymer and thymine. By dissolving the association of the complex through strong selective bonding with mercuric ions that induce the association of the polymer compound, cysteine can be detected as an efficient fluorescent biosensor by changing from green or red fluorescence to the original blue fluorescence of the polymer. .
The water-soluble fluorescent conjugated polymer-mercury-thymine complex of the present invention described above can be applied to various technical fields such as chemical sensor materials and biosensor materials, and in particular, sulfur or Pb of mercury ions not covalently bonded to each other By using specific binding with OL and thymine, it has physical properties corresponding to sensor functions such as responsiveness and selectivity through association of polymers.
The present invention will be described in detail through the following examples. However, the present invention is not limited to the polymer compound used in the present embodiment, and may be any polymer compound in which the energy donor and the donor in which the fluorescent color changes in the state of association with mercury ions due to the formation of an aqueous solution and the complex formation by exciton migration are present in the same molecular chain. Do.
[ Manufacturing example 1] Water Soluble Conjugate Preparation of Polymer Compound
[ Manufacturing example 1-1] of Formula 1 Benzothiadiazole type Polymer compounds ( R One = R 2 = 4- Sulfonytobutyl , Ar One = 1,4- Phenylene Manufacturing
26.5 mg (0.090 mmol) of 4,7-dibromo-2,1,3-benzothiadiazole and 474.4 mg of 1,4-dibromo-2,5-bis (4-sulfonatobutoxy) benzenesodium salt (0.812 mmol) and 297.7 mg (0.902 mmol) of 1,4-benzenediboronic acid bis (pinacol) ester, and 3.5 mg (0.003 mmol) of tetrakis (triphenylphosphine) palladium catalyst with dehumidified 6 mL In DMF with 9 mL 2M Na 2 CO 3 It was dissolved in the mixed solution and refluxed at 90 ° C. for 48 hours. After the reaction, the mixture was cooled to room temperature, poured into a methanol / acetone / ether mixed solution having a volume ratio of 500 mL of 10:40:50 to precipitate crystals, and the precipitate was filtered. The solid obtained by filtration was dissolved in tertiary distilled water and then filtered through an osmosis membrane to obtain a polymer of Formula 1 having a molecular weight of 12,400 or more. The elemental analysis showed that a occupies a mole fraction of 10%.
1 H NMR (300 MHz, D 2 O) δ = 8.1 to 7.3 (2H, aromatic), 7.2 to 6.7 (2H, aromatic), 3.9 (4H, alkyl group), 2.8 (4H, alkyl group), 1.7 to 1.3 (7.8) H, alkyl group) ppm.
[ Manufacturing example 1-2] of Formula 1 Benzothiadiazole type Polymer compounds ( R One = R 2 = 3-N, N, N-T Lymethyl Ammonium profile. Ar One = 1,4- Phenylene Manufacturing
26.5 mg (0.090 mmol) of 4,7-dibromo-2,1,3-benzothiadiazole and 414 mg (0.812) of 1,4-bis (3-bromopropoxy) -2,5-dibromobenzene mmol) and 356.2 mg (1.08 mmol) of 1,4-benzenediboronic acid bis (pinacol) ester and 3.5 mg (0.003 mmol) of tetrakis (triphenylphosphine) palladium catalyst were dehumidified 9 mL of toluene. With 4.5 ml 2M Na 2 CO 3 It was dissolved in the mixed solution and refluxed at 90 ° C. for 48 hours. After the reaction, the mixture was cooled to room temperature and poured into 200 ml of methanol to precipitate crystals. The precipitate was filtered, and the obtained solid was washed with 200 ml of acetone and filtered. The solid obtained by filtration was dissolved in 10 ml of THF, cooled to −78 ° C., and 4 ml of trimethylamine was slowly added thereto. After raising the temperature of the reaction solution to room temperature, the mixture was stirred for 6 hours and poured into 200 ml of acetone to precipitate. The precipitated solid was dissolved in tertiary distilled water and filtered through an osmosis membrane to obtain a polymer of Formula 1 having a molecular weight of 12,400 or more. The elemental analysis showed that a occupies a mole fraction of 10%.
1 H NMR (300 MHz, D 2 O) δ = 8.1-7.3 (2H, aromatic), 7.2-6.7 (2H, aromatic), 4.1 (4H, alkyl group), 3.8-3.2 (6H, alkyl group), 2.9 (4H , Alkyl group), 1.7 (4H, alkyl group) ppm.
[ Manufacturing example 1-3] of Formula 2 Biscyclinylbenzothiadiazole series Polymer compounds ( R One = R 2 = 4- Sulfonytobutyl , Ar 2 = 1,4- Phenylene Manufacturing
21.6 mg (0.057 mmol) of 4,7-bis (5-bromothiophen-2-yl) benzo-2,1,3-thiadiazole and 1,4-dibromo-2,5-bis 300.0 mg (0.514 mmol) of sulfonatobutoxy) benzenesodium salt, 188.0 mg (0.571 mmol) of 1,4-benzenediboronic acid bis (pinacol) ester, and 3.5 mg of tetrakis (triphenylphosphine) palladium catalyst (0.003 mmol) was dissolved in dehumidified 8 mL of DMF and 12 mL of 2M Na 2 CO 3 solution and refluxed at 100 ° C. for 48 hours. After the reaction, the mixture was cooled to room temperature, poured into a methanol / acetone / ether mixed solution having a volume ratio of 500 ml of 10:40:50 to precipitate crystals, and the precipitate was filtered. The solid obtained by filtration was dissolved in tertiary distilled water and then filtered through an osmosis membrane to obtain a polymer of Formula 3 having a molecular weight of 12,400 or more. The elemental analysis showed that c occupied 8% mole fraction.
1 H NMR (300 MHz, D 2 O) δ = 8.1 to 7.3 (3.1H, aromatic), 7.2 to 6.7 (2H, aromatic), 4.0 (2.8H, alkyl group), 3.0 (3H, alkyl group), 2.0 to 1.5 (5H, alkyl group) ppm.
[ Manufacturing example 1-4] of Formula 2 Biscyclinylbenzothiadiazole series Polymer compounds ( R One = R 2 = 3-N, N, N- Trimethylammoniumpropyl , Ar 2 = 1,4-phenylene)
4,7-bis [5- (4,4,5,5, -tetramethyl-1,3,2-dioxaborolane-2-yl) thiophen-2-yl] benzo-2,1,3- 41.2 mg (0.090 mmol) of thiadiazole and 414 mg (0.812 mmol) of 1,4-bis (3-bromopropoxy) -2,5-dibromobenzene and 1,4-benzenediboronic acid bis (pina) 356.2 mg (1.08 mmol) of ester) and 3.5 mg (0.003 mmol) of tetrakis (triphenylphosphine) palladium catalyst were dehumidified with 9 mL of toluene and 4.5 ml of 2M Na 2 CO 3. It was dissolved in the mixed solution and refluxed at 100 ° C. for 48 hours. After the reaction, the mixture was cooled to room temperature and poured into 200 ml of methanol to precipitate crystals. The precipitate was filtered, and the obtained solid was washed with 200 ml of acetone and filtered. The solid obtained by filtration was dissolved in 10 ml of THF, cooled to −78 ° C., and 4 ml of trimethylamine was slowly added thereto. After raising the temperature of the reaction solution to room temperature, the mixture was stirred for 6 hours and poured into 200 ml of acetone to precipitate. The precipitated solid was dissolved in tertiary distilled water and filtered through an osmosis membrane to obtain a polymer of Formula 1 having a molecular weight of 12,400 or more. The elemental analysis showed that c occupies 10% mole fraction.
1 H NMR (300 MHz, D 2 O) δ = 8.1 to 7.3 (3.1H, aromatic), 7.2 to 6.7 (2H, aromatic), 4.0 (2.8H, alkyl group), 3.7 to 3.2 (4.7H, alkyl group), 3.0 (3H, alkyl group), 2.0 (3.1H, alkyl group) ppm.
Preparation Example 2 Preparation of Water-Soluble Conjugated Polymer-Mercury-Thymine Complex
Preparation Example 2-1 Preparation of Polymer-Mercury-Thymine Complex Using Polymer Compound Containing Benzothiadiazole
To prepare the water-soluble conjugated polymer-mercury-thymine complex using the benzothiazole-based water-soluble conjugated polymer compounds prepared in Preparation Examples 1-1 and 1-2, the polymer compounds were buffered with 0.1 molar concentration of sodium phosphate. It was dissolved in solution (pH 7.4) and adjusted to 5.44 × 10 −6 molarity. 6.0x10 <-4> molar concentration of mercury ion was added and dissolved here. Thymine was added to the reactants having a bond with mercury ions at a molar concentration of 2.37 × 10 −3 to form a polymer-mercury-thymine complex, and a solution of the solution by association of a polymer compound from blue fluorescence to green fluorescence was formed. Fluorescence changes were observed using a fluorophotometer.
Preparation Example 2-2 Preparation of Polymer-Mercury-Thymine Complex Using Polymer Compound Containing Biscyenylbenzothiadiazole
0.1 moles of the polymer compounds were formed to form a water-soluble conjugated polymer-mercury-thymine complex using the biscyclinylbenzothiadiazole-based water-soluble conjugated polymer compounds prepared in Preparation Examples 1-3 and Preparation Examples 1-4. It was dissolved in sodium phosphate buffer (pH 7.4) and adjusted to 5.44 × 10 −6 molarity. 6.0x10 <-4> molar concentration of mercury ion was added and dissolved here. Thymine was added to the reactants having a bond with mercury ions at a molar concentration of 2.37 × 10 −3 to form polymer-mercury-thymine complexes. Fluorescence changes were observed using a fluorophotometer.
EXAMPLES Performance Evaluation with Cysteine Sensors
Example 1 Detection of Cysteine Using Benzothiadiazole-based Polymer-Mercury Thymine Complex
In order to confirm the detection ability of the benzothiadiazole-based water-soluble conjugated polymer-mercury-thymine complex prepared in Preparation Example 2-1 for cysteine, the polymer-mercury-thymine complexes prepared from 0 to 1.25x10 -3 mol were used. Different concentrations of cysteine were dissolved in 0.1 molar sodium phosphate buffer (pH 7.4) and dissolved in small amounts, and then the fluorescence change of the solution was observed using a fluorophotometer.
As a result of observing with a fluorescence photometer, the polymer-mercury-thymine complexes formed using the compound of Preparation Example 1-1 or Preparation Example 1-2 showed a gradual change in fluorescence depending on the concentration of cysteine used in the experiment. When cysteine was added, the polymer-mercury-thymine complex using the compound of Preparation Example 1-1 had a 140% increase in blue fluorescence of 428 nm compared to the case where no cysteine was added when the cysteine was 1.25x10 -3 molar concentration. The green fluorescence of 530 nm was decreased by 82%, and the polymer-mercury-thymine complex using the compound of Preparation Example 1-2 increased by 125% in blue fluorescence of 428 nm and decreased by 82% in green fluorescence of 530 nm. In other words, the mercury ions that formed the polymer-mercury-thymine complex escaped by binding with cysteine and the association collapsed. As the concentration of cysteine increased, the fluorescent color changed from green fluorescence to blue fluorescence. This was possible.
Example 2 Detection of Cysteine Using Biscyclinylbenzothiadiazole-based Polymer-Mercury Thymine Complex
In order to confirm the detection ability of the biscyclinylbenzothiadiazole-based water-soluble conjugated polymer-mercury-thymine complex prepared in Preparation Example 2-2 for cysteine, the polymer-mercury-thymine complexes prepared above were 0 to 1.25. Different concentrations of cysteine up to x10 -3 molarity were dissolved in 0.1 molar sodium phosphate buffer solution (pH 7.4) and dissolved in small amounts, and then the fluorescence change of the solution was observed using a fluorophotometer.
As a result of observing with a fluorescence photometer, the polymer-mercury-thymine complexes formed using the compounds of Preparation Examples 1-3 or Preparation Examples 1-4 showed a gradual change in fluorescence depending on the concentration of cysteine used in the experiment. When cysteine was added, the polymer-mercury-thymine complex using the compound of Preparation Example 1-3 had a 152% increase in blue fluorescence of 428 nm compared to the case where cysteine was not added when the cysteine was 1.25x10 -3 molar concentration. The red fluorescence of 636 nm was reduced by 76%, and the polymer-mercury-thymine complex using the compound of Preparation Example 1-4 increased by 175% in blue fluorescence of 428 nm and decreased by 70% in red fluorescence of 636 nm. In other words, the mercury ions that formed the polymer-mercury-thymine complex escaped by binding with cysteine and the association collapsed. As the concentration of cysteine increased, the fluorescent color changed from red fluorescence to blue fluorescence. This was possible.
[ Comparative example 1] Evaluation of detection performance for other amino acids
Instead of using cysteine to confirm the selectivity of cysteine detection of the present invention, lysine, alanine, tyrosine, glycine, leucine, tryptophan, asparagine, valine, aspartic acid, arginine, serine, isoleucine, threonine, methionine, glutamine, Phenylalanine, glutamic acid and histidine were used. Based on the polymer compound of Preparation Example 1-3, a comparative amino acid was added to the biscyclinylbenzothiadiazole-based water-soluble conjugated polymer-mercury-thymine complex prepared in Preparation Example 2-2, and fluorescence was observed. As a result, water-soluble conjugated polymers-mercury-when lysine, alanine, tyrosine, glycine, leucine, tryptophan, asparagine, valine, aspartic acid, arginine, serine, isoleucine, threonine, methionine, glutamine, phenylalanine, glutamic acid and histidine are added respectively There was no change in the blue fluorescence of 428 nm and the red fluorescence of 636 nm of the thymine complex.
From the above results, it was confirmed that the prepared water-soluble conjugated polymer-mercury-thymine complex compositions can be used as biosensors selective for cysteine in which fluorescent color changes depending on the presence and concentration of cysteine.
Claims (7)
The water-soluble fluorescent conjugated polymer compound having an ionic group is a selective fluorescence detection method of cysteine having a polymerization unit selected from the formula (1) or (2).
[Formula 1]
(2)
[In Formula 1 or 2,
R 1 and R 2 are each independently a linear or branched C 1 to C 6 alkyl group substituted with sulfonate or tri (C 1 -C 7) alkylammonium salt at the end;
Ar 1 and Ar 2 are independently of each other (C6-C20) arylene;
a, b, c and d are mole fractions, a and c are independently from each other a real number of 0.05 to 0.5, b is 1-a and d is 1-c.]
The terminal of the alkyl group of the R 1 and R 2 is independently selected from each other, at least one selected from the group consisting of sulfonate, trimethylammonium salt, ethyldimethylammonium salt, diethylmethylammonium salt or triethylammonium salt substituted fluorescence detection method .
Ar 1 and Ar 2 are independently selected from each other phenylene fluorescence detection method of cysteine.
The water-soluble fluorescent conjugated polymer compound has a number average molecular weight (Mn) of 3,000 to 100,000 of the selective fluorescence detection of cysteine.
Selective fluorescence detection method of cysteine in which the polymer-mercury-thymine complex causes fluorescence color change through non-association.
The detection method of selective fluorescence detection of cysteine measured by using a fluorescence photometer.
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| KR101952801B1 (en) | 2017-04-10 | 2019-02-27 | 울산대학교 산학협력단 | Colorimetric sensor, and detection system of amino acid containing sulfur and mercury using the same |
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| KR102023344B1 (en) | 2018-01-25 | 2019-09-20 | 울산대학교 산학협력단 | Polymer based colorimetric sensor capable of selective detection and separation of copper ions |
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