KR101720623B1 - Compound for detecting cyanide, Complex compound thereof and Composition containing the same for detecting cyanide - Google Patents

Abstract

The present invention relates to a compound for detecting cyanide, a complex compound thereof, and a composition for detecting the cyanide comprising the same. A cyanide composition comprising the complex compound of the present invention can be dissolved in a 100% aqueous solution without an auxiliary organic solvent, and can selectively detect only the cyanide, which can be detected with a sensitivity of 1.9 M or less of a WHO maximum drinking water standard value. During detection, to excellently detect the cyanide is possible, by using a colorimetric change and a fluorescence change according to a concentration increase of the cyanide at the same time. Therefore, the cyanide composition comprising the complex compound of the present invention can be usefully used as a detection composition of the cyanide, in fields requiring high water treatment such as drinking water.

Description

TECHNICAL FIELD The present invention relates to a compound for detecting a cyanide, a complex thereof, and a composition for detecting a cyanide containing the compound,

The present invention relates to a compound for detecting a nucleotide, a complex thereof and a composition for detecting the same containing the same.

The cynamide anion is known to be an anion that is highly toxic even at very low concentrations. The cynamide anion inactivates the active site of the enzyme in vivo to induce cell suffocation leading to death as well as causing headache, syncope, and convulsions. Cynamide anions are naturally occurring in certain plants and are used in a variety of industrial processes, which can be a serious problem because they can be suddenly exposed to the aquatic environment. Thus, the World Health Organization (WHO) strictly limits the maximum allowable concentration of cynamide anions in drinking water to below 1.9 × 10 ^-6 M (Non-Patent Document 1).

Therefore, it is very important to develop a method capable of easily detecting the sideride in the aqueous solution. Of the various methods that can detect cynamide anions, methods using fluorescent chemosensors have received much attention in recent years. The sensing method using a fluorescent compound has a merit that a relatively simple instrument is used and a low concentration of the cyanoide can be observed with excellent sensitivity without any other pre-processing. Particularly, a method of detecting a cyanide anion using a copper (II) metal complex has attracted a great deal of attention. It has a property of quenching the fluorescence of a copper (II) metal by forming a complex with a copper (II) the quenching effect is used. When the fluorescence is extinguished after the complex formation, and the cyanide anion is not present, the copper (II) and the cyanide bound to the receptor form a very strong bond, II) is released from the receptor, the fluorescence of the fluorescent compound is amplified as the concentration of the anion of the cyanoide increases.

On the other hand, since most conventionally reported copper (II) complex-based fluorescent complexes require a very high concentration of organic solvent to operate, it is difficult to detect in a 100% aqueous solution and also, The sensitivity is not so good and it can not be measured in the range of the concentration of 1.9 × 10 ^-6 M or less which is the maximum drinking water limit set by the World Health Organization (WHO). Very few solid-state fluorescent chemical sensors can detect sensitivities in 100% aqueous solutions, but they have problems in quantifying and treating the concentration of the sensor due to the solid form (Non-Patent Document 2).

Therefore, it is very important to develop a novel fluorescence sensing method that can sensitively and selectively detect cyanide anions in a 100% aqueous solution.

Accordingly, the present inventors have made efforts to develop a novel fluorescence sensing method capable of dissolving a 100% aqueous solution, selectively detecting a cynamide anion, and sensitively detecting below the WHO reference value, The complex of the invention can be dissolved in an aqueous solution of 100% without an organic solvent and can selectively detect a cineride anion and can be detected at a micromolar concentration of 1.9 × 10 ^-6 M or less, The present inventors have found that fluorescence and color change can be simultaneously used by introducing a fluorescent chromophore capable of detecting fluorescence and color development appropriate for the complex compound.

1. Guidelines for Drinking-Water Quality; World Health Organization: Geneva, Switzerland, 1996. 2. Das, S .; Biswas, S .; Mukherjee, S .; Bandyopadhyay, J .; Samanta, S .; Bhowmick, I .; Hazra, D. K .; Ray, A .; Parui, P. P. RSC Adv. 2014, 4, 96569659.

An object of the present invention is to provide a fluorescent compound.

Another object of the present invention is to provide a complex containing the above compound and a metal ion.

It is still another object of the present invention to provide a composition for detecting a cynode containing the above compound.

It is another object of the present invention to provide a composition for detecting a complex containing the complex.

In order to achieve the above object,

The present invention provides a compound represented by the following formula (1): < EMI ID =

[Chemical Formula 1]

(In the formula 1,

,

,

또는

이고,L is

,

,

or

ego,

으로 표시되는 펩타이드이고,AB

, ≪ / RTI >

Wherein R ¹ and R ² are independently selected from the group consisting of glycine, alanine, valine, leucine, isoleucine, phenylalanine, tryptophan, methionine, cysteine, proline, serine, threonine, tyrosine, asparagine, glutamine, aspartic acid, , Arginine, and histidine).

In addition, the present invention provides a compound of the formula (1) and Ag ^+, Ca ^{2 +,} Cd ^{2 +,} Co ^{2 +,} Cs ^+, Cu ^{2 +,} Fe ^{2 +,} Fe ^{3 +,} Hg ^{2 +,} K ^+, There is provided a complex containing a metal ion selected from the group consisting of Li ⁺ , Mg ^{2 +} , Mn ^{2 +} , Na ⁺ , Ni ^{2 +} and Pb ^{2 +} .

Further, the present invention provides a composition for detecting a cynode containing the compound represented by the above formula (1).

In addition, the present invention provides a composition for detecting a complex containing the complex.

The cynamide composition containing the complex of the present invention can be dissolved in a 100% aqueous solution without an auxiliary organic solvent, and only the cynoid can be selectively detected, and the cynamide can be detected with a sensitivity of less than the WHO maximum drinking water standard of 1.9 [ The present invention can be used as a composition for the detection of cynids in a field where high water treatment such as drinking water is required because it is possible to detect the cyanoide using the color change and fluorescence change according to the increase in the concentration of the cyanoide at the time of detection Lt; / RTI >

FIG. 1A shows an ESI-MS graph of NBD-DDH, and FIG. 1B is an HPLC graph of NBD-DDH.
FIG. 2A shows an ESI-MS graph of SNBD-GGH, and FIG. 2B is an HPLC graph of SNBD-GGH.
FIG. 3A shows an ESI-MS graph of NBD-GGH, and FIG. 3B shows an HPLC graph of NBD-GGH.
FIG. 4A is a graph showing the change of light absorption with an increase in copper (II) metal ion concentration in an aqueous solution in which NBD-SSH (30 μM) is dissolved. FIG. 4B is a graph showing changes in fluorescence according to an increase in copper (II) metal ion concentration in an aqueous solution in which NBD-SSH (30 μM) is dissolved.
FIG. 5A is a graph showing the change of light absorption with an increase in copper (II) metal ion concentration in an aqueous solution in which NBD-DDH (30 μM) is dissolved. FIG. 5B is a graph showing changes in fluorescence according to an increase in Cu (II) metal ion concentration in an aqueous solution in which NBD-DDH (30 μM) is dissolved.
FIG. 6A is a graph showing the change in the absorption by an increase in copper (II) metal ion concentration in an aqueous solution in which SNBD-GGH (30 μM) is dissolved. FIG. 6B is a graph showing changes in fluorescence according to an increase in copper (II) metal ion concentration in an aqueous solution in which SNBD-GGH (30 μM) is dissolved.
FIG. 7A is a graph showing the change of light absorption according to an increase in copper (II) metal ion concentration in an aqueous solution in which NBD-GGH (30 μM) is dissolved. FIG. 7B is a graph showing changes in fluorescence according to an increase in copper (II) metal ion concentration in an aqueous solution in which NBD-GGH (30 μM) is dissolved.
FIG. 8A is a graph showing the change in absorption observed by increasing the concentration of the cynamide in an aqueous solution in which a composition for detecting a nucleus (30 μM) composed of NBD-SSH and Cu (II) was dissolved. FIG. 8B is a graph showing changes in fluorescence observed by increasing the concentration of the cynamide in an aqueous solution in which a composition for detecting a nucleus (30 μM) composed of NBD-SSH and Cu (II) was dissolved.
FIG. 9A is a graph showing the change in absorption exhibited by increasing the concentration of a nucleotide in an aqueous solution in which a composition for detecting a nucleus (30 μM) composed of NBD-DDH and Cu (II) was dissolved. FIG. 9B is a graph showing changes in fluorescence observed by increasing the concentration of a nucleotide in an aqueous solution in which a composition for detecting a nucleus (30 μM) composed of NBD-DDH and Cu (II) was dissolved.
FIG. 10A is a graph showing the change in absorption exhibited by increasing the concentration of a nucleotide in an aqueous solution in which a composition for detecting a nucleus (30 μM) composed of SNBD-GGH and Cu (II) was dissolved. FIG. 10B is a graph showing fluorescence changes caused by an increase in the concentration of the cDNA in an aqueous solution in which a composition for detecting a sinide (30 μM) composed of SNBD-GGH and Cu (II) was dissolved.
FIG. 11A is a graph showing the change in absorption exhibited by increasing the concentration of a nucleotide in an aqueous solution in which a composition for detecting a nucleus (30 μM) composed of NBD-GGH and Cu (II) was dissolved. FIG. 11B is a graph showing the change in fluorescence observed by increasing the concentration of the cynamide in an aqueous solution in which a composition for detecting a nucleus (30 μM) composed of NBD-GGH and Cu (II) was dissolved.
FIG. 12A is a graph showing the results of measurement of F ^- , Cl ^- , Br ^- , I ^- , NO ₃ ^- , CN ^- , SCN ^- , AcO ^- , HCO ₃ ^- , SO ₄ ^2- , ClO ₄ ^- , HPO ₄ ^{2 -} and HAsO ₄ ^{2 -} , FIG. 12B shows a fluorescence graph for the anion, and FIG. 12C shows a colorimetric change for the anion And FIG. 12D is a graph showing fluorescence change (UV, 365 nm) for the anion.
FIG. 13A is a graph of the absorption intensity for an aqueous solution of each of anions including NBD-SSH, cyanide, and anions including cyanide, and FIG. 13B is a graph showing the absorption peaks of anions other than NBD-SSH, And a fluorescent intensity for anions including cyanide.
Fig. 14A is a graph of the absorption intensity for an aqueous solution of each of anions including NBD-DDH, cyanide, and anions including cyanide, and Fig. 14B is an absorption intensity graph of anions including NBD-DDH, cyanide, And a fluorescent intensity for anions including cyanide.
FIG. 15A is a graph of the absorption intensity for aqueous solutions of anions including SNBD-GGH, cyanide, and anions including cyanide, and FIG. 15B is a graph showing the absorption peaks of anions except NBD-DDH, And a fluorescent intensity for anions including cyanide.
FIG. 16A is a graph of the absorption intensity for an aqueous solution of each of anions including NBD-GGH, cyanide, and anions including anions and cyanide, and FIG. 16B is a graph showing the absorption peaks of anions other than NBD-GGH, And a fluorescent intensity for anions including cyanide.
17 is a graph of fluorescence intensity according to the concentration of the syringe in a 100% aqueous solution of NBD-SSH-Cu (II) (0.5 μM).
Fig. 18 is a graph of fluorescence intensity according to the concentration of the syringe in a 100% aqueous solution of NBD-DDH-Cu (II) (30 μM).
19 is a graph of fluorescence intensity according to the concentration of the cDNA in a 100% aqueous solution of SNBD-GGH-Cu (II) (30 [mu] M).
Fig. 20 is a graph of fluorescence intensity according to the concentration of the cyanide in a 100% aqueous solution of NBD-GGH-Cu (II) (30 [mu] M).
21 is an ESI-Mass graph of the composition for the detection of a nucleoid (NBD-SSH-Cu (II)) of the present invention.
Fig. 22 is an ESI-Mass graph of the composition for the detection of a nucleotide of the present invention, which was changed upon detection of a sinide.

Hereinafter, the present invention will be described in detail.

The following description is provided to assist the understanding of the invention, and the present invention is not limited to the following description.

The present invention provides a compound represented by the following formula (1): < EMI ID =

[Chemical Formula 1]

In Formula 1,

The L is not limited to a compound having a fluorescent property,

,

,

또는

이고, 보다 바람직하게

또는

이고, 가장 바람직하게

이다.Preferably

,

,

or

, And more preferably

or

, And most preferably

to be.

Here, L is a fluorescent compound having an absorption wavelength band of 300-650 nm and a fluorescence wavelength band of 480-700 nm, although it is not limited to a compound having inherent fluorescence properties.

The above-mentioned A and B may be selected from an α-amino acid, but not limited to, an amino acid present in nature or obtained by synthesis, and may be independently selected from glycine, alanine, valine, leucine, isoleucine, phenylalanine, tryptophan, methionine, cysteine An amino acid selected from the group consisting of proline, serine, threonine, tyrosine, asparagine, glutamine, aspartic acid, glutamic acid, lysine, arginine and histidine,

Preferably an amino acid having a side chain including -OH and -COOH,

More preferably an amino acid selected from the group consisting of glycine, histidine, serine and aspartic acid,

Most preferably, A-B is glycine-glycine, serine-serine or aspartic acid-aspartic acid.

At this time, the compound represented by the general formula (1) of the present invention plays a role of a receptor of a metal ion, and forms a complex with a metal ion to completely dissolve it in an aqueous solution. In particular, the compound represented by formula (1) of the present invention can be dissolved in an aqueous solution without a separate organic solvent, and can be dissolved in a 100% aqueous solution, preferably forming a complex with a metal ion.

In addition, the present invention provides a compound of the formula (1) and Ag ^+, Ca ^{2 +,} Cd ^{2 +,} Co ^{2 +,} Cs ^+, Cu ^{2 +,} Fe ^{2 +,} Fe ^{3 +,} Hg ^{2 +,} K ^+, A metal ion selected from the group consisting of Li ⁺ , Mg ^{2 +} , Mn ^{2 +} , Na ⁺ , Ni ^{2 +} and Pb ^{2 +} , preferably a complexing compound containing Cu ²⁺ .

At this time, the metal ion forms a complex compound with the compound represented by the formula (1) of the present invention to extinguish the fluorescence property of the compound represented by the formula (1). For example, Cu ^{2 +} among the metal ions has the effect of forming a complex in the form of the compound represented by the formula (1) and N-tetradentate, thereby extinguishing the fluorescent light with excellent fluorescence characteristics.

Further, the present invention provides a composition for detecting a cynode containing the compound represented by the above formula (1).

At this time, the compound represented by the formula (1) may be combined with a metal ion to prepare a composition for detecting a cyanoide, which can be used for the detection of a cyanoide. The composition for detecting a sinide encounters a strong bond between the metal ion and the cyanide to separate the metal ion from the peptide receptor to amplify the fluorescence characteristic of the peptide receptor that has been quenched again and to detect fluorescence therefrom It is possible to perform the function of detecting the visible light and the visible light.

In addition, the composition for detecting a nucleotide can detect a cynode through color change in addition to fluorescence. Specifically, a metal ion separates from a peptide receptor and binds to the cynode, thereby causing a change in color of the composition for detecting a cynode, The cynode can be detected with the naked eye. For example, as shown in Reaction Scheme 1 below, it is possible to detect a cynode by structural change and fluorescence and color change of a composition for detecting NBD-SSH-Cu (II) nucleotide (NBD = 7-nitro- Benzooxadiazole, SSH = serine-serine-histidine tripeptide).

[Reaction Scheme 1]

(Wherein _{x in} [Cu (CN) _x ] ^n- is an integer representing the number of cations bonded to Cu and n is an integer of x - 2.

In addition, the present invention provides a composition for detecting a complex containing the complex.

At this time, the composition for detecting the above-mentioned cDNA binds to a metal ion, and fluorescence of the peptide receptor is extinguished. However, the fluorescence of the peptide receptor which has been extinguished by separating from the peptide receptor, Is amplified again. From this, it is possible to detect the cynode by detecting the cynode in the composition for detecting the cynode of the present invention, and at the same time, accompanied by the change of the color of the composition for detecting the cynode. For example, a cynode can be detected with a composition for detecting a cynode as shown in Reaction Scheme 1 above.

Further, the present invention provides a process for preparing a compound represented by the above formula (1) represented by the following Reaction Scheme 2:

[Reaction Scheme 2]

Protecting group (R ³⁾ protecting group by introducing a histidine in the solid phase -NH- (R ³⁾ - histidine (His) to obtain a compound represented by -NH- solid phase (phase 1),

Introducing an amino acid represented by B into the compound of Step 1 to prepare a compound represented by a protecting group (R ³ ) -B-histidine (His) -NH- solid phase (Step 2)

Introducing an amino acid represented by A into the compound of Step 2 to prepare a compound represented by a protecting group (R ³ ) -AB-histidine (His) -NH- solid phase (Step 3)

(Step 4) of preparing a compound represented by LAB-histidine (His) -NH-solid by removing R ³ from the compound of Step 3 and introducing L, and

Removing the solid phase of the compound of step 4 to prepare the compound represented by formula (1) (step 5).

Hereinafter, the method for preparing the compound represented by the formula (1) according to the present invention will be described in detail.

In the process for preparing the compound represented by the formula (1) according to the present invention, the above step 1 may be carried out by introducing histidine on the protecting group (R ³ ) -NH- to give the protected (R ³ ) -histidine Is prepared.

In this case, the protecting group (R ³ ) of the above step 1 can be generally used in the art and includes, but is not limited to, a 9-fluorenylmethyloxycarbonyl (Fmoc) Can be preferably used. The solid phase is not particularly limited as long as it is a solid phase commonly used in the art, but it is preferable to use a methylbenzohydrillamine (MBHA) resin, a Wang resin, a polyethylene glycol-polystyrene (PEG-PS) resin , Silica nanoparticles, titanium oxide nanoparticles, chitosan and the like, more preferably methylbenzohydrillamine (MBHA) resin and Wang resin.

Further, the above step 1 may be performed as follows. First, the protecting group (R ³ ) is removed from the compound of the protecting group (R ³ ) -NH- by using an amine base, followed by a coupling reaction with R ³ -histidine (trityl) -OH to introduce histidine .

At this time, the amine base is not particularly limited as long as it is usually used for removing a protecting group, but is preferably piperidine, pyrrolidine, morpholine, pyridine, N, N-dimethylaminopyridine, It's Dean.

The molar ratio of the solid phase to the amino acid is preferably 1: 2-10, more preferably 1: 3-7 in terms of the molar ratio of solid phase and amino acid.

In addition, the reagent of the coupling reaction is preferably selected from the group consisting of benzotriazol-1-yl-oxy-tris (dimethylamino) -phosphonium hexafluorophosphate (Py-BOP), 1 -hydroxy-benzotriazole (HBTU), 1-hydroxy-7-aza-benzotriazole (HATU), hydroxybenzotriazole (HOBt), dicyclohexylcarbodiimide (DCC), diisopropylcarbodiimide Is at least one reagent selected from the group consisting of ethyl-3- (3-dimethylaminopropyl) carbodiimide (EDC), carbonyldiimidazole (CDI) and the like, more preferably diisopropylcarbodiimide DIC) and hydroxybenzotriazole (HOBt).

In the method for producing the compound represented by the formula (1) according to the present invention, the step 2 is a step of introducing an amino acid represented by B into the compound of the step 1 to obtain a protecting group (R ³ ) -B-histidine (His) Is a step of preparing a compound represented by the formula

At this time, the step 2 is carried out in the same manner as in step 1, except that the amino acid represented by B is introduced instead of the histidine of the step 1.

The amino acid represented by the above-mentioned B may be, but is not limited to, glycine, alanine, valine, leucine, isoleucine, phenylalanine, tryptophan, methionine, cysteine, proline, serine, threonine, tyrosine, asparagine, glutamine, Is an amino acid selected from the group consisting of aspartic acid, glutamic acid, lysine, arginine and histidine, more preferably an amino acid selected from the group consisting of glycine, histidine, serine and aspartic acid.

In the method for preparing the compound represented by the formula (1) according to the present invention, the step 3 is a step of introducing an amino acid represented by A into the compound of the step 2 to obtain a protecting group (R ³ ) -AB-histidine (His) Is a step of preparing a compound represented by the formula

In this case, step 3 is carried out in the same manner as in step 1, except that the amino acid represented by A is introduced instead of the histidine of step 1 above.

The amino acid represented by A may be, but not limited to, glycine, alanine, valine, leucine, isoleucine, phenylalanine, tryptophan, methionine, cysteine, proline, serine, threonine, tyrosine, asparagine, glutamine, Is an amino acid selected from the group consisting of aspartic acid, glutamic acid, lysine, arginine and histidine, more preferably an amino acid selected from the group consisting of glycine, histidine, serine and aspartic acid.

In the method for preparing the compound represented by the formula (1) according to the present invention, the step 4 is a step of removing the R ³ from the compound of the step 3 and introducing L to obtain a compound represented by the LAB-histidine (His) -NH- .

In this case, Step 4 is a step of introducing a fluorescent compound represented by L instead of the histidine of Step 1 and replacing the coupling reagent DIC and HOBt of Step 1 with N, N-diisopropylethylamine (DIPEA ) Was used as the starting material.

In addition, although L is not limited to a compound having fluorescence property,

,

,

또는

이고, 보다 바람직하게

또는

이고, 가장 바람직하게

이다.Preferably

,

,

or

, And more preferably

or

, And most preferably

to be.

In the process for preparing the compound represented by the formula (1) according to the present invention, the step (5) is a step for preparing the compound represented by the formula (1) by removing the solid phase of the compound of the step (4).

At this time, the step of removing the solid phase in step 5 is a step of reacting the compound of step 4 under an inorganic acid condition. The inorganic acid is preferably one or more inorganic acids selected from the group consisting of trifluoroacetic acid, hydrochloric acid, hydrofluoric acid, formic acid and the like, more preferably trifluoroacetic acid, thioanisole, 3,6-dioxa- 8-octanedithiol and 1,2-ethanedithiol, more preferably at least one inorganic acid selected from the group consisting of trifluoroacetic acid, thioanisole and 3,6-dioxa-1,8 - mixed inorganic acids of octanedithiol or mixed inorganic acids of trifluoroacetic acid, thioanediol and 1,2-ethanedithiol. The inorganic acid may be mixed with distilled water. For example, three trifluoroacetic acid, thioanediol, and 3,6-dioxa-1,8-octanedithiol or 1,2-ethanedithiol were mixed with three mixed inorganic acids and distilled water at a volume ratio of 87.5: 2.5: 5: 2.5.

In addition,

Dissolving the composition for detecting a side chain in an aqueous solution to obtain a mixed aqueous solution (step A); And

And observing the color change by observing the mixture of step A visually or by UV irradiation (step B).

Hereinafter, the method of detecting the above-mentioned side by side will be described in detail.

In the method for detecting a solution according to the present invention, the step (A) is a step of dissolving the composition for detecting a solution of the present invention in an aqueous solution to obtain a mixed aqueous solution.

At this time, the step of obtaining the mixed aqueous solution may completely dissolve the composition for detecting a side of the present invention in an aqueous solution without an organic solvent, and the aqueous solution is not particularly limited, but may preferably be a 100% aqueous solution.

In the method for detecting a cinnamate according to the present invention, the step B is a step of observing a color change by visually observing the mixture of the step A or irradiating UV.

At this time, the step of observing the color change can detect the cynode by comparing the color development of the solution before and after the addition of the composition for detecting the cynode into the aqueous solution of the step A above. In addition, it is possible to detect the cyanide by observing the fluorescence appearing by the addition of the composition for the detection of the present invention of the present invention to an aqueous solution and irradiating with UV, and preferably, the UV irradiation can be performed in the range of 300-650 nm , The fluorescence may preferably be fluorescence of 480-700 nm.

The composition for the detection of the present invention can simultaneously detect the concentration of a solution in a 100% aqueous solution at a concentration lower than the allowable concentration of the drinking water of the World Health Organization using both changes in fluorescence and color development, Sensors, and advanced water treatment, the following Experiments 1 to 5 were carried out in the present invention.

First, as a result of experiments for evaluating the extinction effect according to the change of the metal ion concentration of the compound represented by the formula (1) according to the present invention, the compound represented by the formula (1) It is possible to quench the fluorescence of the compound by forming a complex, and it is possible to prepare the composition for detecting the present invention of the present invention (see Experimental Example 1 below).

As a result of carrying out an experiment for evaluating the detection of the cynide in the composition for detecting a cynode according to the present invention, the composition for detecting a cynode according to the present invention can detect the cynode with high sensitivity, A chemical sensor for detection of nides and an advanced water treatment field (see Experimental Example 2, below).

Further, as a result of conducting experiments for evaluating the selectivity of cynamide in the composition for detecting a cynode according to the present invention, the composition for detecting a cynode according to the present invention can selectively detect a cynode, It is possible to detect the cynode irrespective of the interference, so that it can be usefully used in a chemical sensor for the detection of a cynode and a high water treatment field including the same.

As a result of conducting an experiment for evaluating the detection limit of the composition for detecting a cynode of the present invention, the composition for detecting a cynode according to the present invention was found to be lower than the allowable drinking water value of 1.9 x 10 ^-6 M Can detect the cynide in the concentration of nM and can detect the cynide in the unit of nM and is useful as a composition for detecting a highly sensitive cyanoide in a field of a chemical sensor for detecting a cynode containing it, (See Experimental Example 4 below).

As a result of an experiment to confirm the method for detecting a cynide in the composition for detecting a cynode of the present invention, the composition for detecting a cynode of the present invention forms a complex with a metal ion at a ratio of 1: 1, (Hereinafter referred to as Experimental Example 5). In addition, it is possible to detect the cynoid by a method in which the metal ion is released from the composition for the detection of the cynode.

Hereinafter, the present invention will be described in detail with reference to Production Examples, Examples and Experimental Examples.

However, the following Production Examples, Examples and Experimental Examples are illustrative of the present invention, and the contents of the present invention are not limited thereto.

< Manufacturing example  1> NBD - SSH  Produce

Fmoc-histidine (trityl) -OH, 1-hydroxybenzotriazole (HOBt), and amide linked MBHA resin (100.200 mesh, 0.45 mmol / g) N, N'-diisopropylcarbodiimide (DIC) was purchased from TCI and was purchased from l4-chloro-7-nitro-2,1,3-benzoxadiazole and N, N- Dimethylformamide (DMF) was purchased from Acros Organics.

Chloro-7-nitro-2,1,3-benzoxadiazole (100 mg, 0.5 mmol, 5 equiv) dissolved in DMF (3 mL) containing DIPEA (104.5 μL, 0.6 mmol, 6 equiv) Was added to the solid phase-attached SSH peptide (0.1 mmol), and the resulting mixed solution was subjected to coupling reaction while maintaining it at room temperature for 6 hours. After completion of the coupling reaction, the mixture was treated with a mixture of TFA / TIS / H2O (95: 2.5: 2.5, v / v / v) at room temperature for 4 hours to perform solid phase separation and deprotection. Excess TFA was removed with nitrogen gas and the crude product was precipitated by the addition of cooling ether. The solid precipitate was centrifuged, rinsed with ether, and lyophilized under vacuum. NBD-SSH was prepared by HPLC purification with distilled water (0.1% TFA) / acetonitrile (0.1% TFA).

^{1 H NMR (400 MHz, D} 2 O, 25 ° C) δ 8.66 (s, 1H), 8.55 (d, J = 8.8 Hz, 1H), 7.35 (s, 1H), 6.41 (d, J = 8.4 Hz (M, IH), 4.754.71 (m, 2H), 4.554.53 (m, IH), 4.16 4.15 (m, 2H), 3.923.89 13 (m, 1H);

^{13 C NMR (100 MHz, D} 2 O, 25 ° C) δ 174.0,171.6, 171.2, 163.0, 162.6, 144.2, 143.7, 138.1, 133.6, 128.6, 122.4, 117.4, 61.6, 61.0, 59.4, 55.9, 52.4, 26.4;

HRMS (ESTIOF) calcd 492.1586 (m / z) [M + H ⁺ ] ⁺ , obsd 492.1586 (m / z) [M + H ⁺ ] ⁺ .

< Manufacturing example  2> NBD - DDH  Produce

Chloro-7-nitro-2,1,3-benzoxadiazole (100 mg, 0.5 mmol, 5 equiv) dissolved in DMF (3 mL) containing DIPEA (104.5 μL, 0.6 mmol, 6 equiv) Was added to the solid phase-attached DDH peptide (0.1 mmol), and the resulting mixed solution was subjected to coupling reaction while being maintained at room temperature for 6 hours. After completion of the coupling reaction, the mixture was treated with a mixture of TFA / TIS / H2O (95: 2.5: 2.5, v / v / v) at room temperature for 4 hours to perform solid phase separation and deprotection. Excess TFA was removed with nitrogen gas and the crude product was precipitated by the addition of cooling ether. The solid precipitate was centrifuged, rinsed with ether, and lyophilized under vacuum. NBD-DDH was prepared by HPLC purification with distilled water (0.1% TFA) / acetonitrile (0.1% TFA).

The ESI-MS and HPLC graphs of the prepared NBD-DDH are shown in FIG.

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< Manufacturing example  3> SNBD - Of GGH  Produce

To a solution of 4-chloro-7-nitro-2,1,3-benzothiadiazole (100 mg, 0.5 mmol, 5 equiv.) Dissolved in DMF (3 mL) containing DIPEA (104.5 μL, 0.6 mmol, 6 equiv) ) Was added to the solid phase-attached GGH peptide (0.1 mmol), and the resulting mixed solution was subjected to coupling reaction while maintaining it at room temperature for 6 hours. After completion of the coupling reaction, the mixture was treated with a mixture of TFA / TIS / H2O (95: 2.5: 2.5, v / v / v) at room temperature for 4 hours to perform solid phase separation and deprotection. Excess TFA was removed with nitrogen gas and the crude product was precipitated by the addition of cooling ether. The solid precipitate was centrifuged, rinsed with ether, and lyophilized under vacuum. SNBD-GGH was prepared by HPLC purification with distilled water (0.1% TFA) / acetonitrile (0.1% TFA).

The ESI-MS and HPLC graphs of the SNBD-GGH prepared above are shown in FIG.

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< Manufacturing example  4> NBD - Of GGH  Produce

Chloro-7-nitro-2,1,3-benzoxadiazole (100 mg, 0.5 mmol, 5 equiv) dissolved in DMF (3 mL) containing DIPEA (104.5 μL, 0.6 mmol, 6 equiv) Was added to the solid phase-attached GGH peptide (0.1 mmol), and the resulting mixed solution was subjected to coupling reaction while being maintained at room temperature for 6 hours. After completion of the coupling reaction, the mixture was treated with a mixture of TFA / TIS / H2O (95: 2.5: 2.5, v / v / v) at room temperature for 4 hours to perform solid phase separation and deprotection. Excess TFA was removed with nitrogen gas and the crude product was precipitated by the addition of cooling ether. The solid precipitate was centrifuged, rinsed with ether, and lyophilized under vacuum. NBD-GGH was prepared by HPLC purification with distilled water (0.1% TFA) / acetonitrile (0.1% TFA).

The ESI-MS and HPLC graphs of the prepared NBD-GGH are shown in FIG.

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< Experimental Example  1 > Cu (II) complex Quenching effect  evaluation

In order to evaluate the extinction effect according to the change of the metal ion concentration of the compound represented by the formula (1) according to the present invention, the following experiment was conducted.

Specifically, the above NBD-SSH (Production Example 1), NBD-DDH (Production Example 2), SNBD-GGH (Production Example 3) and NBD-GGH (Production Example 4) The concentrations of copper (II) metal ions were gradually increased, and the changes in absorption and fluorescence were evaluated.

In the fluorescence spectrum measurement, the excitation wavelength was set to 469 nm, and the fluorescence spectra of the prepared test solutions were measured at pH 7.4 (using PBS or HEPES buffer solution). At this time, the excitation and emission slit widths are 10 nm and 5.5 nm, respectively.

< Experimental Example  1-1> NBD - SSH Of the Cu (II) complex Quenching effect  evaluation

The absorption and fluorescence changes of the NBD-SSH prepared in Preparation Example 1 were evaluated, and the results are shown in FIG.

FIG. 4A is a graph showing the change of light absorption with an increase in copper (II) metal ion concentration in an aqueous solution in which NBD-SSH (30 μM) is dissolved. FIG. 4B is a graph showing changes in fluorescence according to an increase in copper (II) metal ion concentration in an aqueous solution in which NBD-SSH (30 μM) is dissolved.

As shown in FIG. 4A, it was confirmed that the greatest light absorption change was observed in the presence of about 30 μM (1 equivalent) of copper (II) metal ion and no further light absorption change was observed at a concentration of more than 30 μM. B, fluorescence is almost extinguished in the presence of about 30 μM (1 equivalent) of copper (II) metal ion, and it can be confirmed that fluorescence change does not occur at a higher concentration.

Therefore, it can be confirmed that NBD-SSH completely quenches fluorescence of NBD-SSH by forming a complex at a molar ratio of 1: 1 with Cu (II) metal ion.

< Experimental Example  1-2> NBD - DDH Of the Cu (II) complex Quenching effect  evaluation

The absorbance and fluorescence changes of the NBD-DDH prepared in Preparation Example 2 were evaluated, and the results are shown in FIG.

FIG. 5A is a graph showing the change of light absorption with an increase in copper (II) metal ion concentration in an aqueous solution in which NBD-DDH (30 μM) is dissolved. FIG. 5B is a graph showing changes in fluorescence according to an increase in Cu (II) metal ion concentration in an aqueous solution in which NBD-DDH (30 μM) is dissolved.

Referring to FIG. 5A, it was confirmed that the greatest light absorption change was observed in the presence of about 30 μM (1 equivalent) of copper (II) metal ion, and no further light absorption change was observed at a concentration of more than 30 μM. B, fluorescence is almost extinguished in the presence of about 30 μM (1 equivalent) of copper (II) metal ion, and it can be confirmed that fluorescence change does not occur at a higher concentration.

Therefore, it can be confirmed that the NBD-DDH of the present invention forms a complex with the Cu (II) metal ion at a molar ratio of 1: 1, whereby the fluorescence of NBD-DDH is completely extinguished.

< Experimental Example  1-3> SNBD - Of GGH Of the Cu (II) complex Quenching effect  evaluation

The absorption and fluorescence changes of SNBD-GGH prepared in Preparation Example 3 were evaluated, and the results are shown in Fig.

FIG. 6A is a graph showing the change in the absorption by an increase in copper (II) metal ion concentration in an aqueous solution in which SNBD-GGH (30 μM) is dissolved. FIG. 6B is a graph showing changes in fluorescence according to an increase in copper (II) metal ion concentration in an aqueous solution in which SNBD-GGH (30 μM) is dissolved.

6A, it was confirmed that the maximum absorption change was observed in the presence of about 30 μM (1 equivalent) of copper (II) metal ion, and no further change in the absorption was observed at a concentration exceeding 30 μM. B, fluorescence is almost extinguished in the presence of about 30 μM (1 equivalent) of copper (II) metal ion, and it can be confirmed that fluorescence change does not occur at a higher concentration.

Therefore, SNBD-GGH of the present invention forms a complex with a Cu (II) metal ion at a molar ratio of 1: 1, indicating that SNBD-GGH fluorescence is completely extinguished.

< Experimental Example  1-4> NBD - Of GGH Of the Cu (II) complex Quenching effect  evaluation

The absorption and fluorescence changes of the NBD-GGH prepared in Preparation Example 4 were evaluated, and the results are shown in Fig.

FIG. 7A is a graph showing the change of light absorption according to an increase in copper (II) metal ion concentration in an aqueous solution in which NBD-GGH (30 μM) is dissolved. FIG. 7B is a graph showing changes in fluorescence according to an increase in copper (II) metal ion concentration in an aqueous solution in which NBD-GGH (30 μM) is dissolved.

7A, it was confirmed that the greatest extinction change was observed in the presence of about 30 μM (1 equivalent) of copper (II) metal ion, and no further change in extinction was observed at a concentration exceeding 30 μM. B, fluorescence is almost extinguished in the presence of about 30 μM (1 equivalent) of copper (II) metal ion, and it can be confirmed that fluorescence change does not occur at a higher concentration.

Therefore, it can be confirmed that the NBD-GGH of the present invention forms a complex with the Cu (II) metal ion at a molar ratio of 1: 1, whereby the fluorescence of NBD-GGH is completely extinguished.

As described in Experimental Example 1, the compound represented by Formula 1 according to the present invention can quench the fluorescence of a compound by forming a complex to donate a metal to the tripeptide receptor, It is possible to prepare a composition for detection.

< Experimental Example  2> Sinain  Of the composition for detection Sinain  Detection evaluation

In order to evaluate the cynode detection of the composition for detecting a cynode according to the present invention, the following experiment was conducted.

The NBD-SSH (Preparation Example 1), NBD-DDH (Production Example 2), SNBD-GGH (Production Example 3) and NBD-GGH (Production Example 4) After the composition was prepared, the concentration of the cynamide in the aqueous solution in which the composition (30 μM) was dissolved was gradually increased to measure the absorption and fluorescence changes, and the cyanide detection evaluation was performed.

< Experimental Example  2-1> NBD - SSH -Cu (II) Sinain  Detection evaluation

The absorption and fluorescence changes of NBD-SSH-Cu (II) were measured and the results are shown in FIG.

FIG. 8A is a graph showing the change in absorption observed by increasing the concentration of the cynamide in an aqueous solution in which a composition for detecting a nucleus (30 μM) composed of NBD-SSH and Cu (II) was dissolved. FIG. 8B is a graph showing changes in fluorescence observed by increasing the concentration of the cynamide in an aqueous solution in which a composition for detecting a nucleus (30 μM) composed of NBD-SSH and Cu (II) was dissolved.

Referring to FIG. 8A, it can be seen that the extinction change was the largest in the presence of about 660 μM (22 equivalents) of the cinnamide, and no further change in the extinction was observed at the above concentrations. Fluorescence changes were observed to be greatest in the presence of about 660 [mu] M (22 equivalents) of the cynode, and no further fluorescence changes were observed at the above concentrations.

Therefore, the NBD-SSH-Cu (II) composition of the present invention can detect 22 equivalents of the cynamide in comparison with one equivalent of the metal ion composition with excellent sensitivity and increase the concentration of the cynamide, It is possible to detect the cynoid as a target, which can be usefully used for the detection of the cynode.

< Experimental Example  2-2> NBD - DDH -Cu (II) Sinain  Detection evaluation

The absorption and fluorescence changes of NBD-DDH-Cu (II) were measured and the results are shown in Fig.

FIG. 9A is a graph showing the change in absorption exhibited by increasing the concentration of a nucleotide in an aqueous solution in which a composition for detecting a nucleus (30 μM) composed of NBD-DDH and Cu (II) was dissolved. FIG. 9B is a graph showing changes in fluorescence observed by increasing the concentration of a nucleotide in an aqueous solution in which a composition for detecting a nucleus (30 μM) composed of NBD-DDH and Cu (II) was dissolved.

Referring to FIG. 9A, it can be seen that the extinction change was the largest in the presence of about 660 μM (22 eq.) Of the cynode, and no further change in the extinction was observed at the above concentrations. Fluorescence changes were observed to be greatest in the presence of about 660 [mu] M (22 equivalents) of the cynode, and no further fluorescence changes were observed at the above concentrations.

Accordingly, the NBD-DDH-Cu (II) composition of the present invention can detect 22 equivalents of the cynamide in comparison with one equivalent of the metal ion composition with excellent sensitivity and increase the fluorescence intensity with increasing concentration of the cynamide, It is possible to detect the cynoid as a target, which can be usefully used for the detection of the cynode.

< Experimental Example  2-3> SNBD - GGH -Cu (II) Sinain  Detection evaluation

The absorption and fluorescence changes of SNBD-GGH-Cu (II) were measured and the results are shown in FIG.

FIG. 10A is a graph showing the change in absorption exhibited by increasing the concentration of a nucleotide in an aqueous solution in which a composition for detecting a nucleus (30 μM) composed of SNBD-GGH and Cu (II) was dissolved. FIG. 10B is a graph showing fluorescence changes caused by an increase in the concentration of the cDNA in an aqueous solution in which a composition for detecting a sinide (30 μM) composed of SNBD-GGH and Cu (II) was dissolved.

Referring to FIG. 10A, it can be seen that the extinction change was the largest in the presence of about 660 μM (22 equivalents) of the cinnamide, and no further change in the extinction was observed at the above concentrations. Fluorescence changes were observed to be greatest in the presence of about 660 [mu] M (22 equivalents) of the cynode, and no further fluorescence changes were observed at the above concentrations.

Therefore, the SNBD-GGH-Cu (II) composition of the present invention can detect 22 equivalents of the cyanoide in comparison with one equivalent of the metal ion composition with excellent sensitivity, and the fluorescence intensity increases with the increase of the concentration of the cDNA, It is possible to detect the cynoid as a target, which can be usefully used for the detection of the cynode.

< Experimental Example  2-4> NBD - GGH -Cu (II) Sinain  Detection evaluation

The absorption and fluorescence changes of NBD-GGH-Cu (II) were measured and the results are shown in Fig.

FIG. 11A is a graph showing the change in absorption exhibited by increasing the concentration of a nucleotide in an aqueous solution in which a composition for detecting a nucleus (30 μM) composed of NBD-GGH and Cu (II) was dissolved. FIG. 11B is a graph showing the change in fluorescence observed by increasing the concentration of the cynamide in an aqueous solution in which a composition for detecting a nucleus (30 μM) composed of NBD-GGH and Cu (II) was dissolved.

 Referring to FIG. 11A, it can be seen that the extinction change was the greatest in the presence of about 660 μM (22 equivalents) of the cinnamide, and no further change in the extinction was observed at the above concentrations. Referring to FIG. 11B, Fluorescence changes were observed to be greatest in the presence of about 660 [mu] M (22 equivalents) of the cynode, and no further fluorescence changes were observed at the above concentrations.

Therefore, the NBD-GGH-Cu (II) composition of the present invention is capable of detecting 22 equivalents of the cynamide in comparison with one equivalent of the metal ion composition with excellent sensitivity, and the intensity of the fluorescence increases with the increase of the concentration of the cynode, It is possible to detect the cynoid as a target, which can be usefully used for the detection of the cynode.

As described in Experimental Example 2, the composition for detecting a sinider according to the present invention can detect a cynide with excellent sensitivity, and can be used in a chemical sensor for detecting a cynode and a high water treatment have.

< Experimental Example  3> Sinain  Of the composition Sinain  Selectivity evaluation

In order to evaluate the selectivity to the cynide of the composition for detecting a sinide according to the present invention, the following experiment was conducted.

The composition for detecting a sinide according to the present invention was tested with the following anions to evaluate the selectivity of the cynodes.

The anions used in the experiments were F ^- , Cl ^- , Br ^- , I ^- , NO ₃ ^- , CN ^- , SCN ^- , AcO ^- , HCO ₃ ^- , SO ₄ ^2- , ClO ₄ ^- , HPO ₄ ^2- and HAsO ₄ ^2- and anion-free group was used as a control group.

First, the absorption and fluorescence spectra were measured for each of the anion-treated group and the non-treated group, and the respective colorimetric changes and fluorescence changes (UV, 365 nm) were visually observed, and the results are shown in FIG.

In addition, by measuring the fluorescence and absorption change of an aqueous solution containing only cyanide, an aqueous solution containing anions other than cyanide, and an aqueous solution containing cyanide and an anion, The cyanide selectivity of the composition was evaluated.

At this time, the anion was dissolved in distilled water to prepare an anion reference solution. The test solution was adjusted so that the concentration of the composition for detecting the cynoid was 30 μM, the concentration of the anion was 660 μM, and the concentration of the PBS buffer solution was 10 mM. In fluorescence measurement, the prepared test solution was adjusted to have an excitation wavelength of 469 nm, an excitation slit and an emission slit width of 10 nm and 5.5 nm, respectively, and fluorescence spectra were measured.

FIG. 12A is a graph showing the results of measurement of F ^- , Cl ^- , Br ^- , I ^- , NO ₃ ^- , CN ^- , SCN ^- , AcO ^- , HCO ₃ ^- , SO ₄ ^2- , ClO ₄ ^- , HPO ₄ ^{2 -} and HAsO ₄ ^{2 -} , FIG. 12B shows a fluorescence graph for the anion, and FIG. 12C shows a colorimetric change for the anion And FIG. 12D is a graph showing fluorescence change (UV, 365 nm) for the anion.

12A, it can be seen that the absorption wavelength band of the sinide is formed at a shorter wavelength than the wavelength range of the anion and anion-free treatment except for the cinnidase. From this, it can be seen that the composition for detecting a cynode of the present invention selectively Referring to FIG. 12B, it can be confirmed that the composition for detecting a side of the present invention exhibits fluorescence which does not appear in the other anion with respect to the side chain. From this, it can be confirmed that the composition for detecting a nucleotide of the present invention selectively reacts with the cinnate. 12C and 12D, the composition for the detection of the present invention showed an orange coloration and no fluorescence on the UV lamp with respect to the anion other than the anion-untreated test solution and the anion, In the presence of the nide, it is possible to confirm that it shows a yellow color and shows fluorescence on the UV lamp.

Accordingly, it can be seen that the composition for detecting a cDNA according to the present invention can selectively detect a cDNA.

< Experimental Example  3-1> NBD - SSH Sinain  Selectivity evaluation

Fluorescence and absorption spectra were measured on an aqueous solution containing only NBD-SSH as a control and an aqueous solution containing only each of the cyanides, an aqueous solution containing anions other than cyanide, an aqueous solution containing cyanide and anions, The results are shown in Fig.

FIG. 13A is a graph of the absorption intensity for an aqueous solution of each of anions including NBD-SSH, cyanide, and anions including cyanide, and FIG. 13B is a graph showing the absorption peaks of anions other than NBD-SSH, And a fluorescent intensity for anions including cyanide.

Referring to FIG. 13A, it can be seen that the composition for the detection of the present invention exhibits a change in the light absorption intensity in an aqueous solution containing only anions and cyanide, and that in FIG. 13B, It can be confirmed that fluorescence appears only in the aqueous solution containing only the anion and the cynamide containing the cynamide.

Therefore, the composition for detecting a cDNA of the present invention does not react with other anions, does not show fluorescence, reacts selectively with the cDNA to show fluorescence, and selectively detects the cDNA even in an aqueous solution containing other anions and a mixture of anions It can be seen that the composition for the detection of the invention of the present invention can detect the sideride without interfering with other ions.

< Experimental Example  3-2> NBD - DDH Sinain  Selectivity evaluation

Fluorescence and absorption spectra were measured for an aqueous solution containing only NBD-DDH as a control and an aqueous solution containing only an individual anion, an aqueous solution containing anions other than cyanide, a solution containing cyanide and an anion, The results are shown in Fig.

Fig. 14A is a graph of the absorption intensity for an aqueous solution of each of anions including NBD-DDH, cyanide, and anions including cyanide, and Fig. 14B is an absorption intensity graph of anions including NBD-DDH, cyanide, And a fluorescent intensity for anions including cyanide.

Referring to FIG. 14A, it can be seen that the composition for detecting a side of the present invention shows a change in the absorption intensity in an aqueous solution containing only anions and cyanide, and that in FIG. 14B, It can be confirmed that fluorescence appears only in the aqueous solution containing only the anion and the cynamide containing the cynamide.

Therefore, the composition for detecting a cDNA of the present invention does not react with other anions, does not show fluorescence, reacts selectively with the cDNA to show fluorescence, and selectively detects the cDNA even in an aqueous solution containing other anions and a mixture of anions It can be seen that the composition for the detection of the invention of the present invention can detect the sideride without interfering with other ions.

< Experimental Example  3-3> SNBD - Of GGH Sinain  Selectivity evaluation

Fluorescence and absorption spectra were measured for an aqueous solution containing only SNBD-GGH as a control group and an aqueous solution containing only an individual anion, an aqueous solution containing anions except for cyanide, an aqueous solution containing cyanide and an anion, The results are shown in Fig.

FIG. 15A is a graph of the absorption intensity for aqueous solutions of anions including SNBD-GGH, cyanide, and anions including cyanide, and FIG. 15B is a graph showing the absorption peaks of anions except NBD-DDH, And a fluorescent intensity for anions including cyanide.

Referring to FIG. 15A, it can be seen that the composition for detecting a side of the present invention exhibits a change in the absorption intensity in an aqueous solution containing only anions and cyanide, and that in the case of FIG. 15B, It can be confirmed that fluorescence appears only in the aqueous solution containing only the anion and the cynamide containing the cynamide.

Therefore, the composition for detecting a cDNA of the present invention does not react with other anions, does not show fluorescence, reacts selectively with the cDNA to show fluorescence, and selectively detects the cDNA even in an aqueous solution containing other anions and a mixture of anions It can be seen that the composition for the detection of the invention of the present invention can detect the sideride without interfering with other ions.

< Experimental Example  3-4> NBD - Of GGH Sinain  Selectivity evaluation

Fluorescence and absorption spectra were measured for an aqueous solution containing only NBD-GGH as a control and an aqueous solution containing only an individual anion, an aqueous solution containing anions other than cyanide, an aqueous solution containing cyanide and an anion, The results are shown in Fig.

FIG. 16A is a graph of the absorption intensity for an aqueous solution of each of anions including NBD-GGH, cyanide, and anions including anions and cyanide, and FIG. 16B is a graph showing the absorption peaks of anions other than NBD-GGH, And a fluorescent intensity for anions including cyanide.

Referring to FIG. 16A, it can be seen that the composition for detecting a sinider of the present invention exhibits a change in the light absorption intensity in an aqueous solution containing only anion and cyanide containing cyanide. Referring to FIG. 16B, It can be confirmed that fluorescence appears only in the aqueous solution containing only the anion and the cynamide containing the cynamide.

Therefore, the composition for detecting a cDNA of the present invention does not react with other anions, does not show fluorescence, reacts selectively with the cDNA to show fluorescence, and selectively detects the cDNA even in an aqueous solution containing other anions and a mixture of anions It can be seen that the composition for the detection of the invention of the present invention can detect the sideride without interfering with other ions.

As described in Experimental Example 3, the composition for detecting a sinider according to the present invention can selectively detect a cynide, and can detect a cynode irrespective of interference of other anions, Sensors and advanced water treatment applications involving the same.

< Experimental Example  4> Sinain  Detection sensitivity evaluation

In order to evaluate the detection limit of the composition for detecting a side of the present invention, the following experiment was conducted.

Specifically, the composition for the detection of the present invention (0.5 μM) of the present invention was dissolved in an aqueous solution of 100%, the concentration of cinnide was gradually increased in units of nano-moles, and the change in fluorescence thereof was measured. Sensitivity and detection limits were assessed (10 mM HEPES buffer solution, pH 7.4, excitation 469 nm, fluorescence detection 525 nm, slit 15/15 nm).

The detection limit was calculated as the minimum cynical concentration at which fluorescence increase of three times or more as compared with the fluorescence intensity in the absence of the cynode.

< Experimental Example  4-1> NBD - SSH Sinain  Detection sensitivity evaluation

Fluorescence changes of the NBD-SSH-Cu (II) composition with respect to changes in the concentration of the cynode were measured, and the results are shown in Fig.

17 is a graph of fluorescence intensity according to the concentration of the syringe in a 100% aqueous solution of NBD-SSH-Cu (II) (0.5 μM).

Referring to FIG. 17, the composition for detecting a sinoid shows a linear behavior with respect to a sine of 0 to 1000 nM, and shows a sensitivity of 0.00278 to a considerably superior sensitivity to the concentration of the sine. The detection limit is 724 nM, which is significantly lower than the concentration of 1.9 × 10 ^-6 M, which is the maximum allowable concentration in the drinking water required by the World Health Organization (WHO).

Therefore, the NBD-SSH-Cu (II) composition for the detection of the sinider according to the present invention can sensitively detect the cyanoide at a value below the allowable concentration of the cynide defined by the World Health Organization, Can be used effectively.

< Experimental Example  4-2> NBD - DDH Sinain  Detection sensitivity evaluation

Fluorescence change of the NBD-DDH-Cu (II) composition with respect to the change of the concentration of the cynode was measured, and the result is shown in Fig.

Fig. 18 is a graph of fluorescence intensity according to the concentration of the syringe in a 100% aqueous solution of NBD-DDH-Cu (II) (30 μM).

Referring to FIG. 18, the composition for detecting a sinide exhibits a linear increase in fluorescence with respect to an increase in the concentration of a sinide, and a detection limit of 14.89 nM, which is the maximum allowable concentration of the cinnid in the drinking water required by the World Health Organization 1.9 x 10 &lt;&quot; ⁶ &gt; M.

Therefore, the NBD-DDH-Cu (II) composition for the detection of the sinider according to the present invention can sensitively detect the cyanoide at a concentration below the allowable concentration of the cynide defined by the World Health Organization, Can be used effectively.

< Experimental Example  4-3> SNBD - Of GGH Sinain  Detection sensitivity evaluation

Fluorescence changes of the SNBD-GGH-Cu (II) composition with respect to changes in the concentration of the cynode were measured, and the results are shown in Fig.

19 is a graph of fluorescence intensity according to the concentration of the cDNA in a 100% aqueous solution of SNBD-GGH-Cu (II) (30 [mu] M).

Referring to FIG. 19, the composition for detecting a sinide exhibits a linear increase in fluorescence with respect to an increase in the concentration of a dinucleotide, and a detection limit of 17.42 nM. This indicates that the maximum allowable concentration of the dinucleotide in the drinking water Which is considerably lower than the concentration of 1.9 x 10 &lt; ^-6 &gt; M.

Therefore, the SNBD-GGH-Cu (II) composition for the detection of the cDNA according to the present invention can detect the cyanoide sensitively at a value below the allowable concentration of the cyanoide determined by the World Health Organization, This can be useful in many cases.

EXPERIMENTAL EXAMPLE 4-4 Evaluation of Sensitivity of NBD-GGH to Cynode Detection

Fluorescence changes of the NBD-GGH-Cu (II) composition were measured for changes in the concentration of the cynode. The results are shown in Fig.

Fig. 20 is a graph of fluorescence intensity according to the concentration of the cyanide in a 100% aqueous solution of NBD-GGH-Cu (II) (30 [mu] M).

Referring to FIG. 20, the composition for detecting a sinide exhibits a linear behavior of increase in fluorescence with respect to an increase in the concentration of a sinide, and a detection limit of 69.42 nM. This indicates that the maximum concentration of the cinnid in the drinking water required by the World Health Organization It can be confirmed that the concentration is considerably lower than the allowable value of 1.9 × 10 ^-6 M.

Therefore, the NBD-GGH-Cu (II) composition for the detection of the sinider according to the present invention can sensitively detect the cyanoide at a value below the allowable concentration of the cynide defined by the World Health Organization, Can be used effectively.

As described in Experimental Example 4, the composition for the detection of sinuses according to the present invention can detect a concentration of a concentration lower than the allowable drinking water value of 1.9 × 10 ^-6 M of the World Health Organization, And can be usefully used in the fields of chemical sensors for the detection of cyanide, advanced water treatment, drinking water and the like.

< Experimental Example  5> High resolution ESI -Mass analysis

In order to confirm the method of detecting the cynode of the composition for detecting a cynode of the present invention, the following experiment was conducted.

Specifically, in order to confirm the change of the composition for the detection of a nucleotide of the present invention and the composition for the detection of a nucleotide at the time of the detection of the cDNA before the detection of the cDNA, analysis was performed by ESI-Mass. The results are shown in FIGS. 21 and 22 Respectively.

21 is an ESI-Mass graph of the composition for the detection of the present invention of the present invention.

Fig. 22 is an ESI-Mass graph of the composition for the detection of a nucleotide of the present invention, which was changed upon detection of a sinide.

21, it can be confirmed that a strong peak appears at m / z = 551.0567 in a high-resolution ESI-Mass analysis in the presence of the composition for detecting a nucleus of the present invention (NBD-SSH and copper (II) ions). This peak corresponds to [NBD-SSH-Cu ^{2 +} - 3H ⁺ ] ^- , whereby the composition for detecting a silver or silver complex of the present invention can be identified.

22, it is confirmed that a new peak of m / z = 492.1587 corresponding to [NBD-SSH + H ⁺ ] ⁺ appears after the addition of the cyanide to the composition for detecting a side of the present invention. From this peak, it can be confirmed that Cu (II) is separated from the composition for detecting a side of the present invention.

Accordingly, the composition for detecting a sinide of the present invention forms a complex with Cu (II) ions at a ratio of 1: 1, and Cu (II) ions are separated from the composition for detecting a side of the present invention upon detection of the side, It can be confirmed that the cyanide is detected by the method of coupling.

Claims (8)

A compound represented by the following formula (1):
[Chemical Formula 1]

(In the formula 1,
L is

,

or

ego,
AB

, &Lt; / RTI &gt;
Wherein R ¹ and R ² are independently selected from the group consisting of glycine, alanine, valine, leucine, isoleucine, phenylalanine, tryptophan, methionine, cysteine, proline, serine, threonine, tyrosine, asparagine, glutamine, aspartic acid, , Arginine, and histidine).
The method according to claim 1,
In the formula 1
AB is as defined in formula 1 of claim 1,
L is

or

&Lt; RTI ID = 0.0 &gt; 1. &Lt; / RTI &gt;
The method according to claim 1,
Wherein L is as defined in claim 1,
AB

, &Lt; / RTI &gt;
Wherein R ¹ and R ² are independently a side chain of one amino acid selected from the group consisting of glycine, histidine, serine, and aspartic acid.
The method according to claim 1,
The L

or

ego,
And AB is glycine-glycine, serine-serine or aspartic acid-aspartic acid.
The compound represented by the general formula (1)
^{Ag +, Ca 2 +, Cd} 2 +, Co 2 +, Cs +, Cu 2 +, Fe 2 +, Fe 3 +, Hg 2 +, K +, Li +, Mg 2 +, Mn 2 +, Na + , Ni &lt; ^{2 +} &gt;, and Pb &lt; ^{2 +} &gt;.
6. The method of claim 5,
Wherein the complex contains a compound represented by the general formula (1) of claim 1 and Cu ^{2 +} .
A compound represented by Formula 1 below; And
^{Ag +, Ca 2+, Cd 2+} , Co 2+, Cs +, Cu 2+, Fe 2+, Fe 3+, Hg 2+, K +, Li +, Mg 2+, Mn 2+, Na + , Ni ^2+, and Pb ²⁺ , and a complex containing the metal ion.
[Chemical Formula 1]

(In the formula 1,
L is

,

,

or

ego,
AB

, &Lt; / RTI &gt;
Wherein R ¹ and R ² are independently selected from the group consisting of glycine, alanine, valine, leucine, isoleucine, phenylalanine, tryptophan, methionine, cysteine, proline, serine, threonine, tyrosine, asparagine, glutamine, aspartic acid, , Arginine, and histidine).
A composition for detecting a cynode containing a compound represented by the following formula (1):
[Chemical Formula 1]

(In the formula 1,
L is

,

,

or

ego,
AB

, &Lt; / RTI &gt;
Wherein R ¹ and R ² are independently selected from the group consisting of glycine, alanine, valine, leucine, isoleucine, phenylalanine, tryptophan, methionine, cysteine, proline, serine, threonine, tyrosine, asparagine, glutamine, aspartic acid, , Arginine, and histidine).

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