CN103864685A - 一种荧光探针及其在检测二价铁离子中的应用 - Google Patents
一种荧光探针及其在检测二价铁离子中的应用 Download PDFInfo
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Abstract
一种荧光探针及其在检测二价铁离子中的应用涉及一类在二价铁离子存在下荧光发生增强的荧光探针。本发明提供了一种可用于选择性检测二价铁离子的荧光探针。本发明在荧光母体上引入有机碲醚结构作为与二价铁离子反应的活性中心，利用反应物与产物的荧光差别，实现选择性地检测二价铁离子。
Description
技术领域
本发明提供了一种可用于选择性检测二价铁离子的荧光探针。在荧光母体上引入有机碲醚结构作为与二价铁离子反应的活性中心，利用反应物与产物的荧光差别实现选择性地检测二价铁离子。
背景技术
铁作为生命体中含量最多的过渡元素，具有十分重要的生理功能，缺乏和过负荷都会引起疾病。现在已知铁参与造血、组成酶、能量代谢、人体免疫、基因表达等生理过程；缺乏铁会引起贫血，而铁过负荷则会引起癌症，肝肾损伤，心血管疾病，帕金森病以及内分泌系统疾病。铁在生命体系中的主要存在形式是二价的铁，然而，长久以来检测手段的缺乏阻碍了人们对二价铁离子在生命体系中作用的研究。
荧光探针是有效检测生命体内二价铁离子的手段之一。一个具有应用前景的荧光探针应具有作用前后荧光变化明显、对目标分子响应快、选择性好、合成简单等优点。基于有机自由基TEMPO对Fe2+的选择性氧化反应，Jin-Long Chen等以芘为荧光团设计了荧光探针pyrene-TEMPO（结构见图1，Jin-Long Chen et.al,Spectrochimica Acta Part A 63(2006)438–443）用于专一性地检测Fe2+。但是该探针在检测时需要硫酸的浓度达到0.2mol/L，故不能应用于生物体系的研究。Bo Tang等发表了一个用以检测细胞内Fe2+的荧光探针BDP-Cy-Tpy（结构见图1，Bo Tang et.al,Chem.Eur.J.2011,17,10520–10523），与Fe2+作用后花菁母体的荧光降低，BODIPY母体的荧光几乎不变，利用这两个荧光团发出荧光的比率来检测Fe2+。但是该荧光探针含有两个荧光团（与铁作用的荧光团发出的荧光降低），合成步骤十分复杂。L.Praveen等发表了检测二价铁离子的荧光探针DansSQ（结构见图1，L.Praveen et.al,Tetrahedron Letters 51(2010)6626–6629）,检测条件（乙腈：水=9:1）中有机溶剂比例过高决定了该探针不能用于生命体系中二价铁离子的检测。因此开发可用于生物体系中二价铁离子检测的荧光探针具有重要意义。
发明内容
本发明就是针对上述问题，提供了一种可用于选择性检测细胞内二价铁离子的荧光探针，此探针可以在生理条件下选择性地与二价铁离子作用，作用后荧光显著增强。
本发明采用如下技术方案：采用萘酰亚胺染料作为荧光母体，在萘酰亚胺母体上引入有机碲醚结构作为与二价铁离子反应的活性中心，利用反应物与产物的荧光差别，实现选择性地检测二价铁离子。
所述荧光探针的通式为通式Ⅰ，R1、R2、R3为烷基、芳基或含杂原子的取代基。R1、R2、R3为烷基、芳基时，一般为C1～C20，最佳为C1～ C10；R1、R2、R3为杂原子取代基时，为含有磺酸基、羧基、羟基、卤素、氨基、胺基、烷氧基、氰基或硝基的取代基。
通式Ⅰ
上述通式Ⅰ表示的化合物应用于检测二价铁离子，其特征在于反应生成具有通式II结构的化合物，从而导致荧光改变。
通式II
通式II中，R1、R2为烷基、芳基或含杂原子的取代基，R3为-OH或-O-。R1、R2为烷基、芳基时，一般为C1～C20，最佳为C1～C10。R1、R2为杂原子取代基时，为含有磺酸基、羧基、羟基、卤素、氨基、胺基、烷氧基、氰基或硝基的取代基。
通式Ⅰ可对Fe2+定性、定量的检测。将浓度呈梯度变化的Fe2+水溶液分别加入通式Ⅰ的水溶液中，反应达到平衡后，分别测定各样品的荧光强度，然后以Fe2+的浓度为横坐标、反应后体系的荧光强度为纵坐标作图，即可根据荧光强度从图中读出待测溶液中Fe2+的含量。
本发明的有益效果：这类化合物在Fe2+存在下荧光发生显著改变，可用于高选择性、高灵敏性地检测Fe2+。尤其是，这类化合物可用于细胞内的Fe2+检测，这对于深入研究Fe2+在生物体内的吸收、输送及累积等过程的动力学机理、进一步了解Fe2+的生理和病理作用具有重要意义。
附图说明
图1背景技术中所举的已公开的用于检测二价铁离子的荧光探针；
图2本发明提供的荧光探针Naph-Te检测Fe2+的原理示意图；
图3实施例1中合成荧光探针Naph-Te的流程图；
图4实施例2中荧光探针Naph-Te对Fe2+的选择性示意图；
图5实施例3中荧光探针Naph-Te水溶液的荧光强度随Fe2+浓度的变 化示意图；
图6实施例3中pH对荧光强度的影响示意图；
图7实施例4中荧光探针Naph-Te用于细胞内二价铁离子检测的激光共聚焦显微镜照片。
具体实施方式
实施例用于进一步说明本发明，但本发明不限于实施例。
实施例1（探针的合成）：
如图3所示，实施例所采用的探针化合物的结构用代号Naph-Te表示。
4-溴-氮-丁基-1，8-萘酰亚胺的合成：向250ml三口烧瓶中加入15g 4-溴-1，8萘酐，加入200ml无水乙醇，加热至回流；向滴液漏斗内加入8mL正丁胺的50mL无水乙醇溶液，将滴液漏斗内的溶液逐滴加入到三口烧瓶中，滴加完毕后，再回流反应6小时。过滤，将滤液减压蒸发，所得固体经柱层析纯化得4-溴-氮-丁基-1，8-萘酰亚胺。
Naph-Te的合成：向50mL三口烧瓶中加入0.50g联苯二碲（可购买获得），真空/氮气置换三次，加入20ml无水乙醇，得红色悬浊液，在冰浴条件下加入0.09g NaBH4，反应放出大量气泡，得到无色溶液；升温至乙醇回流，加入0.40g碘化亚铜和0.30g 4-溴-氮-丁基-1，8-萘酰亚胺，回流反应15分钟。过滤，将滤液减压蒸发，所得固体经柱层析纯化得目标化合物Naph-Te。
实施例2（Naph-Te对Fe2+的选择性）：
先后将7500μL PBS（pH=7.4，浓度为0.01M磷酸盐缓冲溶液）、1500uL乙腈、10μL探针乙腈溶液、50μL金属盐溶液加入到1cm ⅹ1cm ⅹ4cm的比色皿中，使得混匀后探针Naph-Te的浓度为5μM，各金属阳离子除Na+、K+、Ca2+、Mg2+浓度为1mM，其余均为50μM（空白加100μL水），V乙腈：V水=1:5。等待反应70min后测量工作液的荧光发射光谱，λex=465nm。
Naph-Te对Fe2+的选择性实验结果如图4所示,纵坐标表示荧光增强倍数，即反应后溶液在547nm的荧光强度与反应前在547nm的荧光强度的比值。图4表明Naph-Te对Fe2+具有很好的选择性，体系荧光显著增强。测定条件下，相比于Fe2+，其他金属离子导致的荧光增强可以忽略。
实施例3（Naph-Te对Fe2+的定量检测）：
先后将1500uLPB（浓度为0.2M磷酸盐缓冲溶液）、300uL探针乙腈溶液、1100uL水、100uL Fe2+溶液加入到1cm ⅹ1cm ⅹ4cm的比色皿中，使得混匀后V乙腈：V水=1:9，PB浓度为0.1M。等待反应20min后测量工作液的荧光发射光谱，λex=465nm。
图5表示在Naph-Te的浓度为1μM，V乙腈：V水=1:9，pH=7.4，PB浓度为0.1M的条件下，工作液在500nm到600nm的积分荧光强度F与加入的Fe2+的浓度成线性关系。工作曲线方程为：F=100474.4[Fe2+](μM)+137646.1，R=0.996。定容后Fe2+浓度：0，1.05,2.12, 3.18,4.26,5,34,6.43,8.63,9.75,15.38,21.05,26.76,32.50μM。表明该探针可以检测人体生理水平的Fe2+。
图6中圆点表示3μM Naph-Te在V乙腈：V水=1:5，PB浓度为20mM的条件下，反应30分钟后，550nm处荧光强度与pH的关系；方点表示均加入3μMFe2+30分钟后，以上各不同pH样品的荧光强度。说明在生理条件下，pH对Naph-Te的影响可以忽略。
实施例4（Naph-Te用于细胞内二价铁离子的检测）：
HL-7702细胞按照American type Tissue Culture Collection规定进行培养。先用10.0μM Naph-Te孵育HL-7702细胞10分钟，然后用pH=7.4、浓度为0.1M的PB洗涤3次，置于共聚焦荧光显微镜下拍照，结果如图7a)所示；然后再加入20.0μM FeCl2孵育细胞10分钟，用pH=7.4，浓度为0.1M的PB洗涤3次，用共聚焦显微镜拍照，结果如图7b)所示，荧光强度明显增强；图7c)为细胞的明场图。
Claims (5)
1.一种荧光探针，其特征在于，所述荧光探针的通式为：
通式Ⅰ
通式Ⅰ中，R1、R2、R3分别为C1～C20的烷基、含有杂原子集团的C1～C20的烷基、苯基、C7～C20取代苯基，含有杂原子集团的苯基、或含有杂原子集团的C7～C20取代苯基；
苯基上的取代基为C1～C14的烷基；
杂原子集团为磺酸基、羧基、羟基、卤素、氨基、胺基、烷氧基、氰基或硝基中的一种或二种以上。
2.根据权利要求1所述荧光探针，其特征在于：R1、R2、R3分别为C1～C10烷基、C7～C12取代苯基，苯基上的取代基为C1～C5的烷基。
3.一种权利要求1所述荧光探针在检测二价铁离子中的应用，其特征在于：通式Ⅰ表示的化合物在检测溶液中Fe2+的过程时，于溶液中，通式Ⅰ表示的化合物与Fe2+反应后生成具有通式II结构的化合物，从而导致荧光改变；
通式II
通式II中R1、R2分别与通式Ⅰ表示的化合物中的R1、R2相同，R3为-OH或-O-。
4.根据权利要求3所述荧光探针在检测二价铁离子中的应用，其特征在于：具有如下结构的化合物（Naph-Te），用于存在于模拟生理环境，即pH为7.4的磷酸盐缓冲溶液中的Fe2+检测，生成4-羟基-N-丁基-1,8萘酰亚胺，在pH为7.4时，有一部分4-羟基-N-丁基-1,8萘酰亚胺的羟基会脱去质子；
5.根据权利要求3所述荧光探针在检测二价铁离子中的应用，其特征在于：所述通式Ⅰ的化合物应用于检测Fe2+，Fe2+的测定包括以下工序：
（a）使具有通式I结构的化合物与Fe2+反应；
（b）测定由上述工序中的反应引起的体系荧光变化。
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| CN112209877A (zh) * | 2020-04-15 | 2021-01-12 | 广东省微生物研究所（广东省微生物分析检测中心） | 一种二价铁荧光探针及其应用 |
| CN114262304A (zh) * | 2021-12-13 | 2022-04-01 | 武汉大学中南医院 | 响应Fe(Ⅱ)离子的生物发光荧光素的合成方法及其应用 |
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| CN112209877A (zh) * | 2020-04-15 | 2021-01-12 | 广东省微生物研究所（广东省微生物分析检测中心） | 一种二价铁荧光探针及其应用 |
| CN114262304A (zh) * | 2021-12-13 | 2022-04-01 | 武汉大学中南医院 | 响应Fe(Ⅱ)离子的生物发光荧光素的合成方法及其应用 |
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