CN114014891B - 一种嘌呤环修饰的荧光探针及其在检测钴离子上的应用 - Google Patents
一种嘌呤环修饰的荧光探针及其在检测钴离子上的应用 Download PDFInfo
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
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- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
- C07F9/65616—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings containing the ring system having three or more than three double bonds between ring members or between ring members and non-ring members, e.g. purine or analogs
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- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
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Abstract
本发明公开了一种嘌呤环修饰的荧光探针及其在检测钴离子上的应用，所述嘌呤环修饰的荧光探针的结构式如下所示：该荧光探针通过席夫碱反应形成C＝N键，杂化轨道上的N原子具有孤对电子，具有良好的灵活性和配位性，对钴离子表现出高的灵敏性和选择性，并且响应时间快，可作为荧光探针检测金属离子和药物在生物体内的分布。
Description
技术领域
本发明属于钴离子检测技术领域，具体涉及一种嘌呤环修饰的荧光探针及其在检测钴离子上的应用。
背景技术
钴是一种存在于岩石、矿物质、土壤和海水中的必需微量元素。在生物系统方面，钴是维生素B12和酶的重要成分，在铁代谢和血红蛋白合成中起着关键作用。过量摄入钴会导致许多疾病，包括血管舒张、哮喘和甲状腺功能减退。缺乏钴还会导致不良反应，如生长迟缓、贫血、食欲不振和泌乳减少。在环境污染方面，燃煤向大气中注入了大量的钴气体，对大气造成一定程度的污染。当海水或河水中富集一定量的钴时，对鱼类和水生动物造成一定危害。当钴浓度达到10mg/L时，会导致鲫鱼和丝鱼死亡。土壤中钴的含量为0.05～65ppm，当土壤被钴污染，浓度达到10mg/L时，会导致农作物死亡。
目前，已经开发出多种检测钴离子的方法，最常见的是原子吸收光谱(AAS)、电感耦合等离子体原子发射光谱(ICP-AES)、色谱和电化学检测等。但由于这些方法存在仪器成本高、操作人员专业性高、实时检测困难等缺点，不适合现场检测和实际应用。相比之下，荧光分析方法操作简单、检测时间短、响应速度快、选择性高、灵敏度高，能够实时原位检测，视觉感知方便。它们在医学、分析化学和环境科学等领域发展快速是一种很有前途的分析方法。
嘌呤广泛存在于生物体内，其碱性支架具有良好的共轭特性，在荧光探针和生物成像中表现出优异的生物学和光学特性。
发明内容
针对现有的不足，本发明提供了一种嘌呤环修饰的荧光探针及其在检测钴离子上的应用，该荧光探针通过席夫碱反应形成C＝N键，杂化轨道上的N原子具有孤对电子，具有良好的灵活性和配位性，对钴离子表现出高的灵敏性和选择性，并且响应时间快，可作为荧光探针检测金属离子和药物在生物体内的分布。
针对现有技术的不足，本发明采取的技术方案为：
一种嘌呤环修饰的荧光探针，所述荧光探针的结构式如下所示：
上述嘌呤环修饰的荧光探针的制备方法，包括以下步骤：
步骤1，以4,6-二氯-5-氨基嘧啶和1-萘胺为原料，通过取代反应得到6-氯-N4-(萘-1-基)嘧啶-4,5-二胺，记为中间体化合物A；
步骤2，将中间体化合物A、1-萘酸、DTAC和多聚磷酸溶解在有机溶剂中反应得6-氯-9-(萘-1-基)-8-(萘环-1-基)-9H-嘌呤，记为化合物B；
步骤3，化合物B再与水合肼在有机溶剂中反应得6-肼基-9-(萘-1-基)-8-(萘环-1-基)-9H-嘌呤，记为化合物C；
步骤,4，将化合物C和2-二苯基膦苯甲醛缩合得(E)-6-(2-(2-(二苯基膦基)亚苄基)肼基)-9-(萘-1-基)-8-(萘-2-基)-9H-嘌呤，记为嘌呤环修饰的荧光探针D。
反应的基本路线如下所示：
作为改进的是，将4,6-二氯-5-氨基嘧啶和1-萘胺溶于甲醇中，加入浓HCl，回流反应，反应结束后，冷却至室温，减压除去甲醇，用NaOH溶解并用乙酸乙酯萃取，旋蒸得到的粗产品用甲醇和水重结晶可得到纯净的中间体化合物A。
作为改进的是，步骤2中中间体化合物A、1-萘酸、DTAC和多聚磷酸溶解在三氯氧磷中，搅拌回流，反应完全后，旋蒸除去三氯氧磷，得到油状物质，向油状物质中加入冰水，得到固体物质，柱层析纯化得到中间体化合物B。
作为改进的是，步骤3中中间体化合物B、水合肼溶解于甲醇中，回流搅拌，反应完全后，旋蒸除去甲醇，再用氯仿萃取，旋干即得固体化合物中间体C。
作为改进的是，步骤4中中间体化合物C、2-二苯基膦苯甲醛溶于甲醇中，回流搅拌，反应完全后，冷却至室温，抽滤反应液析出的固体得到粗产品，粗产品经重结晶后烘干即得检测钴离子的荧光探针化合物D。
上述任一种荧光探针D在检测钴离子上应用。
有益效果：
与现有的技术相比，本发明一种嘌呤环修饰的荧光探针及其在检测钴离子上的应用，有以下三个优势，一是该合成采用的是席夫碱反应的原理，反应过程简单，易于操作，并且最终产物是稳定的固体粉末，易于储存。二是该反应选用嘌呤环为母体，其碱性支架具有良好的共轭特性，在荧光探针和生物成像中表现出优异的生物学和光学特性。三是在Co2+检测方面，该荧光探针表现出了高的选择性和灵敏性，响应时间短能以固体状态检测钴离子，有很好的便携性和稳定性，在监测环境和生理系统中的Co2+含量方面显示出广阔的前景。
附图说明
图1为实施例1中合成的荧光探针的核磁共振1H NMR谱图；
图2为实施例1中合成的荧光探针的核磁共振13C NMR谱图；
图3为实施例1中合成的荧光探针的质谱MS谱图；
图4为在DMSO-H2O(v/v＝9:1)的溶液中，实施例1合成的荧光探针对各种金属离子的荧光选择图；
图5为在DMSO-H2O(v/v＝9:1)的溶液中，实施例1合成的荧光探针对钴离子的紫外吸收光谱图；
图6为在DMSO-H2O(v/v＝9:1)的溶液中，各种金属离子对实施例1合成的荧光探针检测钴离子的影响图；
图7为在DMSO-H2O(v/v＝9:1)的溶液中，实施例1合成的荧光探针与钴离子的络合Job-plot谱图；
图8为实施例1合成的荧光探针对钴离子的时间响应图谱；
图9为在DMSO-H2O(v/v＝9:1)的溶液中，实施例1合成的荧光探针对不同浓度的钴离子的荧光光谱图；
图10为实施例1合成的荧光探针溶液浸泡的试纸在不同浓度钴离子溶液中浸泡后的颜色变化。
具体实施方式
以下结合附图对本发明进行详细说明。
本发明中使用的实验方法如无特殊说明，均为常规方法。实验所用的材料、试剂等，如无特殊说明，均可从商业途径得到。实施例中所选用的以下所有试剂皆为市售分析纯或化学纯。
其中，实施例中各种金属离子溶液是由纯度为99％以上的氯化盐化学试剂如无水氯化锌、无水氯化铁等加去离子水配置而成的。
按照如下反应式进行以下实施例。
实施例1
1、制备中间体A(6-氯-N4-(萘-1-基)嘧啶-4,5-二胺)
在100mL圆底烧瓶中加入4、6-二氯-5-氨基嘧啶(5.00g，30mmol)和1-萘胺(8.58g，60mmol)，然后加入50mL甲醇，加热溶解，冷却至室温后，加入5mL 12mol/L HCl，将反应液在65℃下搅拌回流5天，反应完成后，将反应液冷却至室温，旋蒸除去反应液的甲醇，将粗产物溶解在50mL 1M NaOH水溶液中，并用乙酸乙酯萃取3次，合并有机相，然后依次用1.2M HCl、饱和NaHCO3，饱和NaCl洗涤有机相。上述过程完成后将有机相用无水硫酸钠干燥，减压蒸馏除去有机溶剂，可得到粗产品。该粗产品用CH3OH/H2O(v/v，1∶5)进行重结晶，烘干后可得到浅紫色的固体粉末即为中间体化合物A(5.75g，收率71％)。ESI-MS m/z calcd forC14H10ClN4[M-H]-269.0,found 269.0.
2、制备中间体B(6-氯-9-(萘-1-基)-8-(萘环-1-基)-9H-嘌呤)
在100mL圆底烧瓶中加入化合物A(1.00g，3.70mmol)、1-萘酸(3.18g，18.50mmol)、DTAC(0.10g，10％mmol)和25mL三氯氧磷。待上述固体物质全部溶解后加入多聚磷酸(5.00g，14.80mmol)。在80℃回流搅拌72小时，TLC板监测直到反应完成。将反应液冷却至室温，减压蒸馏除去有机溶剂，得到褐色油状物质。在冰浴条件下，向反应液中加入100mL冰水，搅拌可析出大量固体，抽滤出固体，干燥即为粗产品。CH3OH/CH2Cl2(v/v，1/250)柱层析纯化得到浅黄色的固体粉末即为中间体化合物B(0.56g，收率42％)。ESI-MS m/zcalcd forC25H16ClN4[M+H]+407.1,found 406.9.
3、制备中间体C(6-肼基-9-(萘-1-基)-8-(萘环-1-基)-9H-嘌呤)
在100ml圆底烧瓶中加入化合物B(0.32g，0.80mmol)和10ml甲醇，65℃加热使其完全溶解。之后，将水合肼(0.25g，4mmol)溶于10ml甲醇中，用恒压滴液漏斗缓慢滴入上述反应液中。在65℃下回流搅拌，并通过TLC板监测反应，直到反应完成。接着，将反应液冷却至室温，减压除去溶剂，用氯仿萃取数次。合并有机相，干燥，旋干得到浅黄色的中间体化合物C(0.23g，收率70％)。ESI-MS m/z calcd for C25H19N6[M+H]+403.2,found 403.2.
4、制备钴离子检测荧光探针化合物D
将6-肼基-9-(萘-1-基)-8-(萘-2-基)-9H-嘌呤(108.2mg,0.373mmol)和2-二苯基膦苯甲醛(100mg,0.248mmol)加入到100mL圆底烧瓶，然后加入甲醇(10mL)溶解，回流搅拌4小时。之后，将反应溶液冷却至室温，将反应溶液中沉淀的固体抽滤得到粗产物。重结晶粗产物，得到白色固体即为纯净的钴离子荧光探针化合物D(131.2mg，72％)。
1H NMR(400MHz,DMSO-d6)δ12.21(s,1H),9.14(s,1H),8.33(s,2H),8.27(s,1H),7.96(t,J＝7.9Hz,2H),7.92–7.85(m,2H),7.66(d,J＝7.4Hz,1H),7.50(ddt,J＝15.6,7.5,3.9Hz,5H),7.45–7.34(m,9H),7.34–7.22(m,6H),6.80(dd,J＝8.0,4.4Hz,1H).13C NMR(101MHz,DMSO-d6)δ153.40,150.86,139.26,139.07,136.28,136.18,135.98,134.20,134.01,133.50,133.44,131.88,131.62,130.66,130.35,130.17,129.95,129.71,129.49,129.42,128.78,128.70,128.02,127.91,127.47,127.30,127.23,126.93,126.47,126.09,125.90,125.06,122.97,118.94.ESI-MS m/z calcd for C44H32N6P[M+H]+675.2,found675.3.
从核磁共振1H NMR(图1)和核磁共振的13C NMR(图2)以及质谱MS谱图(图3)可确定该检测钴离子的探针结构正确。
实施例2
将实施例1中合成的嘌呤环修饰的荧光探针溶解于DMSO中制备成1.0mM的探针储备液。将各种金属离子(Zn2+,Ni2+,Al3+,Cr3+,Mn2+,Mg2+,Pb2+,K+,Ca2+,Fe2+,Na+,Ag+,Cd2+,Pd2 +,Fe3+,Cu2+,Cu+,Ba2+和Sn2+,)用蒸馏水配置成3.0mM的金属离子储备液。取3mL提前配置的空白储备样DMSO-H2O(v/v＝9:1)于5mL的离心管中，加入30μL的探针储备液和50μL的金属离子储备液，静置1小时。用荧光光谱仪和紫外分光光度计进行测试，得知最大激发波长为298nm，最大发射波长为410nm。
图4展示的是荧光探针对各种金属离子的选择图。在3mL的空白储备样DMSO-H2O(v/v＝9:1)中依次加入30μL的探针储备液，然后加入50μL各种不同的金属离子储备液，静置1小时。荧光光谱测试这些样液的荧光强度，结果表明，在410nm处加入钴离子的样液荧光打开并且荧光强度最大，而加入其他离子没有明显的变化。以上的现象证明该探针对钴离子有很高的选择性。
图5是荧光探针对钴离子的紫外吸收光谱图。这项测试的过程是分别取3mL的空白储备样DMSO-H2O(v/v＝9:1)于两个比色皿中，分别加入30μL的探针储备液，之后在一个比色皿中加入50μL的钴离子储备液，另一个则不加。用紫外分光光度计进行测试。谱图情况表明，荧光探针本身在λ＝355nm处有较强的紫外吸收。加入钴离子后，吸收峰减弱，与此同时，在λ＝424nm处的吸收峰增强。以上这些结果表明荧光探针是一种有效的检测Co2+的化合物。
图6是其他金属离子对荧光探针检测钴离子的干扰图。在3mL的空白储备样DMSO-H2O(v/v＝9:1)中依次加入30μL的探针储备液和50μL的钴离子储备液，然后再向各个空白样中加入50μL各种干扰离子储备液，静置1个小时候测试其荧光强度，并和只加钴离子的样液的荧光强度对比。从最终比对的柱状图可知，其他离子几乎不能使原先的荧光强度发生明显变化。因此，本发明的荧光探针对钴离子的选择不会被其他共存的金属离子干扰。
图7是荧光探针与Co2+络合的比例图。在3mL的空白储备样DMSO-H2O(v/v＝9:1)中加入一定量的探针储备液和一定量的钴离子储备液。两种储备液按照1：9，2：8，3：7，4：6，5：5，6：4，7：3，8：2，9：1的比例来添加。静置1小时后，用紫外分光光度计测试。以离子占总浓度的比例为横坐标，上述样品在λ＝424nm处的吸收峰强度为纵坐标作图。从Job's plot图可知最大吸收强度出现在0.3处，由此可以推断出荧光探针与Co2+离子的结合比为2:1。
图8为本发明的荧光探针对钴离子的时间响应图。在3mL的空白储备样DMSO-H2O(v/v＝9:1)中加入30μL的探针储备液和50μL的钴离子储备液，每隔1分钟进行一次荧光强度的测试。记录时间和对应的强度，绘制图谱。图谱的趋势表明在1分钟之内荧光探针就可与钴离子结合打开荧光，并且在10分钟之内达到稳定。上述结果表明本发明的荧光探针对于Co2+检测是快速而且稳定的。
图9是荧光探针对Co2+的荧光滴定光谱图即不同浓度Co2+存在时的荧光强度谱图。在3mL的空白储备样DMSO-H2O(v/v＝9:1)中加入30μL的探针储备液和0～15μL(0、1、2、3...15μL)的钴离子储备液，静置一段时间后测试。最终得到的图谱显示出：随着离子浓度的不断增加，荧光的强度也逐渐变强，并且在7μL这一状态之后保持稳定。与此同时，该探针溶液在365nm灯光下的颜色也由青色变成了绿色。以上现象表明，本发明的荧光探针对Co2+有高的敏感性。
图10是在365nm灯光下，被探针储备液和不同浓度离子储备液浸泡后的试纸颜色变化。首先把5张滤纸浸泡在1mM的探针储备液中，充分浸泡半个小时后取出干燥。随后，将这5张滤纸分别浸泡在0、0.05、0.1、0.5和1.0mM的Co2+溶液中，30分钟后取出干燥。在365nm的灯光下可观察到滤纸的颜色由淡青色荧光转变成了较强的绿色荧光。由此可知，本发明的荧光探针可制作为便携的试纸条用于监测Co2+。
以上所述，仅为本发明较佳的具体实施方式，本发明的保护范围不限于此，任何熟悉本技术领域的技术人员在本发明披露的技术范围内，可显而易见地得到的技术方案的简单变化或等效替换均落入本发明的保护范围内。
Claims (7)
1.一种嘌呤环修饰的荧光探针，其特征在于，所述荧光探针的结构式如下所示：
。
2.基于权利要求1所述的嘌呤环修饰的荧光探针的制备方法，其特征在于，包括以下步骤：
步骤1，以4,6-二氯-5-氨基嘧啶和1-萘胺为原料，通过取代反应得到6-氯-N4-（萘-1-基）嘧啶-4,5-二胺，记为中间体化合物A；
步骤2，将中间体化合物A、1-萘酸、DTAC和多聚磷酸溶解在有机溶剂中反应得6-氯-9-（萘-1-基）-8-（萘环-1-基）-9H-嘌呤，记为化合物B；
步骤3，化合物B再与水合肼在有机溶剂中反应可得6-肼基-9-（萘-1-基）-8-（萘环-1-基）-9H-嘌呤，记为化合物C；
步骤4，将化合物C和2-二苯基膦苯甲醛缩合得(E)-6-(2-(2-(二苯基膦基)亚苄基)肼基)-9-(萘-1-基)-8-（萘-2-基）-9H-嘌呤，记为嘌呤环修饰的荧光探针D。
3.根据权利要求2所述的嘌呤环修饰的荧光探针的制备方法，其特征在于，将4,6-二氯-5-氨基嘧啶和1-萘胺溶于甲醇中，加入浓HCl进行回流反应，反应结束后，冷却至室温，减压除去甲醇，再用NaOH溶解并用乙酸乙酯萃取，旋蒸得到的粗产品用甲醇和水重结晶可得到纯净的中间体化合物A。
4.根据权利要求2所述的嘌呤环修饰的荧光探针的制备方法，其特征在于，步骤2中中间体化合物A、1-萘酸、DTAC和多聚磷酸溶解在三氯氧磷中，搅拌回流，反应完全后，旋蒸除去三氯氧磷，得到油状物质，再向油状物质中加入冰水，得到固体物质，柱层析纯化得到中间体化合物B。
5.根据权利要求2所述的嘌呤环修饰的荧光探针的制备方法，其特征在于，步骤3中化合物B、水合肼溶解于甲醇中，回流搅拌，反应完全后，旋蒸除去甲醇，再用氯仿萃取，旋干即得固体化合物中间体C。
6.根据权利要求2所述的嘌呤环修饰的荧光探针的制备方法，其特征在于，步骤4中中间体化合物C、2-二苯基膦苯甲醛溶于甲醇中，回流搅拌，反应完全后，冷却至室温，抽滤反应液析出固体得到粗产品，粗产品经重结晶后，烘干即得检测钴离子的荧光探针化合物D。
7.基于权利要求1-6中任一种荧光探针D在检测钴离子上应用，所述检测为非疾病的诊断方法。
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