KR101000248B1 - Off-on ATP sensor using fluorescent ATP receptor and quencher - Google Patents
Off-on ATP sensor using fluorescent ATP receptor and quencher Download PDFInfo
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Abstract
본 발명은 ATP 형광 수용체인 [Zn2(9,10-비스[(2,2'-디피콜일아미노)메틸]안트라센)]4+과 그 형광 수용체와 결합이 가능한 소광체인 파이로카테콜 바이올렛을 단순하게 혼합하여 만들어진 복합체인 화학센서에 관한 것이다. 이러한 화학센서는 중성 수용액 상에서 수백 nM에서 수백 uM의 넓은 검출 범위와 수 백 nM의 검출 한계를 가진 ATP 선택적인 형광 센서이다.The present invention relates to [Zn 2 (9,10-bis [(2,2'-dipicolylamino) methyl] anthracene)] 4+ , an ATP fluorescent receptor, and pyrocatechol violet, a quencher that can bind to the fluorescent receptor. It relates to a chemical sensor that is a complex made by simply mixing. These chemical sensors are ATP selective fluorescent sensors with a broad detection range of several hundred nM to several hundred uM and a detection limit of several hundred nM in neutral aqueous solution.
ATP, 형광센서, [Zn2(9,10-비스[(2,2'-디피콜일아미노)메틸]안트라센)]4+, 화학 앙상블, 파이로카테콜 바이올렛 ATP, fluorescence sensor, [Zn2 (9,10-bis [(2,2'-dipicolylamino) methyl] anthracene)] 4+, chemical ensemble, pyrocatechol violet
Description
본 발명은 ATP를 선택적으로 검출할 수 있는 형광 센서에 관한 것이다.The present invention relates to a fluorescence sensor capable of selectively detecting ATP.
Adenosine-5'-triphosphate(ATP)는 생체내 주요 대사 물질로 생체내 에너지를 전달 및 저장하는 역할을 하며, 다양한 대사 산물의 전구체이고, DNA의 구성 요소가 되는 등 다양한 역할을 수행한다. ATP는 키나제 효소들의 기질로 세포내 ATP양에 따라 키나제 활성을 조절함으로써 생체 내 세포 사멸, 세포 분열, 생체 내 신호 전달 등 다양한 역할을 수행한다.Adenosine-5'-triphosphate (ATP) is a major metabolite in the body, which transmits and stores energy in vivo, is a precursor of various metabolites, and plays a variety of roles such as being a component of DNA. ATP is a substrate of kinase enzymes and regulates kinase activity according to the amount of intracellular ATP, thereby performing various roles such as cell death in vivo, cell division, and signal transmission in vivo.
ATP의 양을 측정하는 일반적인 방법은 루시페린(luciferine)과 ATP가 루시페라제(luciferase)에 의해 반응이 진행시 빛을 방출하게 되는 원리에 기초한다. 이때 방출되는 빛을 정량함으로써 ATP의 양을 측정할 수 있다. 하지만 이러한 방법은 효소를 사용함으로 인해 온도, pH, 염 농도 등 주의 환경에 매우 민감함으로 ATP의 양의 측정에 어려움이 따른다(Gilles R., "Effect of various ions on ATP determinations using the 'luciferine-luciferase' system." Arch Int Physiol Biochim. 1976 Oct;84(4):807-17).The general method of measuring the amount of ATP is based on the principle that luciferine and ATP emit light as the reaction proceeds by luciferase. At this time, the amount of ATP may be measured by quantifying the emitted light. However, this method is very sensitive to the environment of the state, such as temperature, pH, salt concentration, etc. due to the use of enzymes (Gilles R., "Effect of various ions on ATP determinations using the 'luciferine-luciferase) 'system.' Arch Int Physiol Biochim. 1976 Oct; 84 (4): 807-17).
초분자 화학을 이용하여 ATP를 인지하고 더 나아가 센싱하는 화학센서들이 최근 들어 다양한 연구 집단에 의해 개발되었다. 초기의 ATP의 화학 센서는 정전기적 상호작용, 수소결합 등을 이용하여 ATP 내의 음이온을 감지함으로써 ATP를 센싱하는 화학센서들이 개발되었다. 하지만 이러한 센서들은 정전기적 상호 작용을 이용하기 때문에 다른 음이온에 대한 선택성이 매우 낮을 뿐만 아니라 수용액 상에서는 ATP를 검출하는데 어려움이 있었다.Chemical sensors that recognize and further sense ATP using supramolecular chemistry have recently been developed by various research groups. Early chemical sensors of ATP developed chemical sensors that sense ATP by detecting anions in ATP using electrostatic interactions, hydrogen bonds, etc. However, because these sensors use electrostatic interactions, they have very low selectivity for other anions and have difficulty in detecting ATP in aqueous solution.
최근 들어 이러한 문제점을 극복하고자 금속-리간드 상호 작용을 이용한 ATP 형광 화학센서들이 개발되었다. 이러한 형태의 ATP 센서는 수용액 상에서 ATP를 검출할 수 있었을 뿐만 아니라 다른 음이온에 대해서도 높은 감도를 보였다. 하지만 상기 센서는 센서 자체의 큰 형광 세기에 의해 낮은 농도의 ATP 검출시 작은 형광 변화로 인해 어려움이 있었다.Recently, ATP fluorescent chemical sensors using metal-ligand interaction have been developed to overcome this problem. This type of ATP sensor not only detected ATP in aqueous solution, but also showed high sensitivity to other anions. However, the sensor has difficulty due to a small fluorescence change in detecting low concentrations of ATP due to the large fluorescence intensity of the sensor itself.
따라서 본 발명이 이루고자 하는 기술적 과제는 수용액 상에서 다른 음이온에 대한 높은 선택성 및 높은 감도를 가지는 off-on ATP 형광 화학센서를 제공하는 것이며, 또한 이러한 ATP 형광 화학센서를 이용하는 여러 가지 방법, 예를 들어, 효소의 활성 측정방법, 효소 억제제의 스크리닝 방법 등을 제공하는 것이다.Accordingly, the present invention is to provide an off-on ATP fluorescence chemical sensor having high selectivity and high sensitivity to other anions in aqueous solution, and also various methods using such ATP fluorescence chemical sensor, for example, It provides a method for measuring the activity of the enzyme, a method for screening the enzyme inhibitor and the like.
상기 기술적 과제를 달성하기 위하여, 본 발명은 ATP를 효과적으로 인지하는 형광 주인 화합물인 [Zn2(9,10-bis[(2,2'-dipicolyl-amino)methyl]antracene)]4+ 및 소광체인 파이로카테콜 바이올렛(pyrocatechol violet)을 포함하는 것을 특징으로 하는 ATP 검출용 조성물을 제공하며, 이러한 조성물 내에서 [Zn2(9,10-비스[(2,2'-디피콜일아미노)메틸]안트라센)]4+과 파이로카테콜 바이올렛(pyrocatechol violet)은 복합체를 형성한다.In order to achieve the above technical problem, the present invention is a fluorescent host compound that effectively recognizes ATP [Zn 2 (9,10-bis [(2,2'-dipicolyl-amino) methyl] antracene)] 4 + and quencher It provides a composition for detecting ATP, characterized in that it comprises pyrocatechol violet (Zn 2 (9,10-bis [(2,2'-dipicolylamino) methyl] in such a composition. Anthracene)] 4+ and pyrocatechol violet form a complex.
[Zn2(9,10-bis[(2,2'-dipicolyl-amino)methyl]antracene)]4+와 소광체인 파이로카테콜 바이올렛의 복합체 형성과 이러한 복합체에 ATP가 혼합되었을 때 일어나는 반응은 하기 반응식 1과 같이 표현될 수 있다.The complex formation of [Zn 2 (9,10-bis [(2,2'-dipicolyl-amino) methyl] antracene)] 4+ with the quencher pyrocatechol violet and the reaction that occurs when ATP is mixed with these complexes It may be represented by the following
본 발명은 또한 [Zn2(9,10-bis[(2,2'-dipicolyl-amino)methyl]antracene)]4+와 소광체인 파이로카테콜 바이올렛을 이용하는 것을 특징으로 하는 ATP 검출 방법을 제공하며, 이러한 ATP 검출 방법은 ATP를 기질로 사용하는 효소의 활성을 측정하거나, 이러한 효소의 억제제를 스크리닝 하는 데에 유용하게 사용될 수 있다.The present invention also provides a method for detecting ATP using [Zn 2 (9,10-bis [(2,2'-dipicolyl-amino) methyl] antracene)] 4+ and pyrocatechol violet as a quencher. In addition, the ATP detection method may be useful for measuring the activity of enzymes using ATP as a substrate or screening inhibitors of such enzymes.
본 발명은 ATP 형광 수용체인 [Zn2(9,10-bis[(2,2'-dipicolylamino)methyl]antracene)]4+과 그 형광 수용체와 결합이 가능한 소광체인 파이로카테콜 바이올렛(pyrocatechol violet)을 단순하게 혼합한 복합체로 중성 수용액 상에서 수백 nM에서 수백 uM의 넓은 검출 범위와 수백 nM의 검출 한계를 가지며, 다른 음이온에 대비 높은 ATP 선택성을 가진 ATP 형광 센서를 제공한다. 이때의 형광 증폭은 60여배 이상으로 매우 크다. 따라서 생체 시료 및 일반 시료에서 ATP를 효율적으로 검출할 수 있을 뿐만 아니라 ATP를 기질로 하는 다양한 효소의 활성 측정할 수 있고, 또한 그 효소의 억제제를 고속 스크리닝할 수 있다.The present invention relates to an ATP fluorescent receptor [Zn 2 (9,10-bis [(2,2'-dipicolylamino) methyl] antracene)] 4+ and a pyrocatechol violet which is a quencher capable of binding to the fluorescent receptor. ) Is a complex of a simple mixture, which provides a wide detection range of several hundred nM to several hundred uM and a few hundred nM detection limit in a neutral aqueous solution, and provides an ATP fluorescent sensor having high ATP selectivity against other anions. The fluorescence amplification at this time is very large, more than 60 times. Therefore, not only the ATP can be efficiently detected in biological samples and normal samples, but also the activity of various enzymes based on ATP can be measured, and the inhibitors of the enzyme can be screened at high speed.
또한 본 발명은 형광 주인 화합물과 그 형광 주인 화합물과 결합이 가능한 소광체를 이용하여 off-on 형광 센서 시스템을 개발할 수 있는 방법을 제공한다.The present invention also provides a method for developing an off-on fluorescent sensor system using a fluorescent host compound and a quencher that can be combined with the fluorescent host compound.
이하, 본 발명의 이해를 돕기 위하여 실시예 등을 들어 상세하게 설명하기로 한다. 그러나, 본 발명에 따른 실시예들은 여러 가지 다른 형태로 변형될 수 있으며, 본 발명의 범위가 하기 실시예들에 한정되는 것으로 해석돼서는 안 된다. 본 발명의 실시예들은 당업계에서 평균적인 지식을 가진 자에게 본 발명을 보다 완전하게 설명하기 위해 제공되는 것이다.Hereinafter, examples and the like will be described in detail to help understand the present invention. However, embodiments according to the present invention can be modified in many different forms, the scope of the invention should not be construed as limited to the following examples. Embodiments of the present invention are provided to more fully describe the present invention to those skilled in the art.
<실시예 1> ATP 인지 형광 주인 화합물(1)의 합성Example 1 Synthesis of ATP Recognized Fluorescent Host Compound (1)
ATP 인지 형광 주인 화합물(1)인 [Zn2(9,10-bis[(2,2'-dipicolylamino)methyl]antracene)]4+를 하기 반응식 2와 같이 합성하였다.[Zn 2 (9,10-bis [(2,2'-dipicolylamino) methyl] antracene)] 4+ , an ATP-recognized fluorescent host compound (1), was synthesized as in
보다 구체적으로, DMF 10ml에 9,10-비스(클로로메틸)안트라센 1.10g, 2,2'-디피콜일아민(dipicolyamine) 1.75g 및 칼륨 카보네이트 2.21g을 넣는다. 이후, KI 13mg은 소량의 DMF에 녹여 천천히 한방울씩 첨가한다. 이후, 상온에서 하루 동안 교반한다. 반응물에 1N의 HCl을 3 ml를 가하고 반응물을 10 ml 에틸 아세티이트로 2번 씻어준다. 수용액 층은 4N의 NaOH로 알칼리화시키고 에틸 아세테이트-THF 1:1 용액으로 2번 추출한다. 유기층을 받아내고 소금물로 씻어준 후 MgSO4로 감압하에서 건조한다. 생성물을 THF-AcOEt로 재결정하여 주인 화합물(1)를 얻는다.More specifically, 1.10 g of 9,10-bis (chloromethyl) anthracene, 1.75 g of 2,2'-dipicolylamine and 2.21 g of potassium carbonate are added to 10 ml of DMF. After that, 13 mg of KI is dissolved in a small amount of DMF and slowly added drop by drop. Thereafter, the mixture is stirred at room temperature for one day. 3 ml of 1N HCl is added to the reaction, and the reaction is washed twice with 10 ml ethyl acetate. The aqueous layer is alkalized with 4N NaOH and extracted twice with ethyl acetate-THF 1: 1 solution. The organic layer was taken out, washed with brine and dried under reduced pressure with MgSO 4 . The product is recrystallized from THF-AcOEt to give the master compound ( 1 ).
<실시예 2> 주인 화합물(1)과 파이로카테콜 바이올렛의 복합체 형성Example 2 Complex Formation of Host Compound (1) and Pyrocatechol Violet
이렇게 합성 되어진 형광 화합물은 자체적으로 매우 강한 형광을 발하게 되는데 본 발명에서는 효율적인 ATP 검출 형광센서를 제공하기 위해 ATP 인지 형광 주인화합물(1)과 결합이 가능한 파이로카테콜 바이올렛(pyrocatechol violet)을 가하여 ATP 인지 형광 주인화합물(1)의 초기 형광을 소광시켰고, 이러한 과정을 통하 여 복합체(1·pyrocatechol violet)을 합성하였다. 이러한 복합체를 "off-on ATP 형광 화학센서"라 명명하였다(반응식 3 참조).The synthesized fluorescent compound emits very strong fluorescence by itself. In the present invention, in order to provide an efficient ATP detection fluorescent sensor, ATP is added by adding pyrocatechol violet, which can be combined with ATP-recognized fluorescent host compound ( 1 ). The initial fluorescence of the cognitive fluorescence host compound ( 1 ) was quenched, and a complex ( 1 · pyrocatechol violet) was synthesized through this process. This complex was named "off-on ATP fluorescence chemistry sensor" (see Scheme 3).
<실시예 3> 소광 효과의 평가(도 1)Example 3 Evaluation of the matting effect (FIG. 1)
[Zn2(9,10-bis[(2,2'-dipicolylamino)methyl]antracene)]4+의 용액에 소광체인 파이로카테콜 바이올렛을 가할 때의 형광 변화를 측정하였다. 그 결과를 도 1에 나타내었다. 실험 조건은 Trizma buffer 0.05M(SIGMA) pH 7.2, 센서인 주인 화합물 5 uM이었으며, 소광체인 파이로카테콜 바이올렛은 0 내지 25 uM의 범위에서 단계적으로 첨가하였다. Fluorescence change was measured when pyrocatechol violet, a quencher, was added to a solution of [Zn 2 (9,10-bis [(2,2'-dipicolylamino) methyl] antracene)] 4+ . The results are shown in FIG. Experimental conditions were Trizma buffer 0.05M (SIGMA) pH 7.2, 5 uM of the host compound as a sensor, and pyrocatechol violet as a quencher was added stepwise in the range of 0 to 25 uM.
도 1에 나타나는 바와 같이, 파이로카테콜 바이올렛을 첨가함에 따라 주징 화합물인 [Zn2(9,10-bis[(2,2'-dipicolylamino)methyl]antracene)]4+의 형광이 감소하였다.As shown in FIG. 1, the fluorescence of the main compound [Zn 2 (9,10-bis [(2,2'-dipicolylamino) methyl] antracene)] 4+ decreased as pyrocatechol violet was added.
<실시예 4> 본 발명에 따른 복합체의 ATP 선택성 평가(도 2)Example 4 Evaluation of ATP Selectivity of the Complex According to the Present Invention (FIG. 2)
본 발명에 따른 복합체의 ATP 선택성을 평가하였다. 즉, 다른 음이온에 대한 off-on ATP 형광 화학센서의 ATP 선택성을 평가하였으며, 그 결과를 도 2에 나타내었다. 실험 조건은 Trizma buffer 0.05M(SIGMA) pH 7.2, 센서인 주인 화합물 5 uM, 파이로카테콜 바이올렛 10 uM 및 ATP 5 uM이었으며, 다른 음이온의 농도는 5 uM이었다. 다른 음이온으로는 HPO4, Br, HCO3, Cl, SO4, ClO4, HSO3, NO3, N3 및 NaOAc를 사용하였다.The ATP selectivity of the complexes according to the invention was evaluated. That is, the ATP selectivity of the off-on ATP fluorescence chemical sensor for other anions was evaluated, and the results are shown in FIG. 2. Experimental conditions were Trizma buffer 0.05M (SIGMA) pH 7.2, 5 uM of the host compound as a sensor, 10 uM of pyrocatechol violet and 5 uM of ATP, and the concentration of the other anions was 5 uM. As other anions, HPO 4 , Br, HCO 3 , Cl, SO 4 , ClO 4 , HSO 3 , NO 3 , N 3 and NaOAc were used.
도 2에 나타나는 바와 같이, 본 발명에 따른 off-on ATP 형광 화학센서는 생체 내에서 쉽게 발견되는 다양한 음이온이 존재하는 상황에서도 ATP에 대해 높은 선택성을 나타내었다.As shown in Figure 2, the off-on ATP fluorescence chemical sensor according to the present invention showed a high selectivity for ATP even in the presence of various anions easily found in vivo.
<실시예 5> ATP 검출 범위 및 검출 한도 평가(도 3 및 4)Example 5 ATP Detection Range and Detection Limit Evaluation (FIGS. 3 and 4)
본 발명에 따른 off-on ATP 형광 화학센서의 ATP 검출시 검출 범위 및 검출 한도를 평가하였다. 실험 조건은 Trizma buffer 0.05M(SIGMA) pH 7.2, 센서인 주인 화합물 5 uM 및 파이로카테콜 바이올렛 10 uM이었으며, ATP는 0 내지 80 uM의 범위에서 평가하였다. 그 결과를 도 3 및 4에 나타내었다.The detection range and detection limit of the ATP detection of the off-on ATP fluorescent chemical sensor according to the present invention were evaluated. Experimental conditions were Trizma buffer 0.05M (SIGMA) pH 7.2, 5 uM of the host compound as a sensor and 10 uM of pyrocatechol violet, and ATP was evaluated in the range of 0 to 80 uM. The results are shown in FIGS. 3 and 4.
도 3 및 4에 나타나는 바와 같이, 본 발명에 따른 복합체는 ATP 농도와 검출 형광의 상관성이 수백 nM에서 수백 uM의 넓은 농도 범위에서 뛰어났으며, 검출 한도가 수백 nM로 매우 낮았다. 또한 이때의 형광의 증폭은 60여배 이상으로 매우 컸다.As shown in Figures 3 and 4, the complex according to the present invention was excellent in the correlation between the ATP concentration and the detection fluorescence in a wide concentration range of several hundred nM to several hundred uM, the detection limit was very low, several hundred nM. In addition, the amplification of the fluorescence at this time was very large, more than 60 times.
도 1은 [Zn2(9,10-bis[(2,2'-dipicolylamino)methyl]antracene)]4+의 용액에 소광체인 파이로카테콜 바이올렛(pyrocatechol violet)를 가할 때의 형광변화를 측정한 결과이다.1 is a solution of [Zn 2 (9,10-bis [(2,2'-dipicolylamino) methyl] antracene)] 4+ This is a result of measuring the fluorescence change when pyrocatechol violet is added as a quencher.
도 2는 다른 음이온에 대한 off-on ATP 형광 화학센서의 ATP 선택성을 평가한 결과이다.Figure 2 is the result of evaluating the ATP selectivity of the off-on ATP fluorescence chemical sensor for other anions.
도 3 및 4는 off-on ATP 형광 화학센서의 ATP 검출시 검출 범위 및 검출 한도를 평가한 결과이다.3 and 4 are the results of evaluating the detection range and the detection limit when detecting the ATP of the off-on ATP fluorescent chemical sensor.
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