CN106083870A - 一种新型磷酸二氢根荧光离子探针及制备方法与应用 - Google Patents
一种新型磷酸二氢根荧光离子探针及制备方法与应用 Download PDFInfo
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- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
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Abstract
一种用于磷酸二氢根离子检测的荧光分子探针试剂，为罗丹明6G内酰胺萘基衍生物，其与磷酸二氢根作用导致螺环打开，荧光上升来检测磷酸二氢根离子。制备方法是：首先罗丹明6G与氨气反应生成罗丹明6G内酰胺，继续与1‑萘异硫氰酸酯反应生成罗丹明6G内酰胺萘基衍生物。本发明的优点是：本发明制备的罗丹明6G萘基衍生物，合成简单方便，产率高，易于制备，适于放大合成及实际生产应用。其作为新型磷酸二氢根阴离子荧光探针可以应用于生物以及离子检测领域。采用荧光光谱监测手段，探针分子在乙腈和水混合溶液中显示对于磷酸二氢根离子的专一性识别且灵敏度高，具有广阔的应用前景。
Description
【技术领域】
本发明属于阴离子检测的荧光分子探针领域，特别是一种用于磷酸二氢根离子检测的荧光分子探针试剂及其制备方法。
【背景技术】
荧光离子探针能够将离子存在信息转换成易被检测的荧光信号，进而获得特定离子的识别功能。在体系中与特定离子的相互作用会发生特定的物理化学变化，从而导致相应的荧光信号发生改变。荧光离子探针具有高灵敏度，简单易行等诸多优点。
罗丹明类荧光分子由于具有摩尔消光系数高、光稳定性好、荧光量子产率高、较长的激发波长和发射波长等优异的光物理和光化学性能，已成为制备荧光探针的理想材料之一。罗丹明荧光探针主要用于检测金属阳离子方面，而对于检测阴离子方面应用较少。
磷酸阴离子在生物以及生态系统中有着非常重要的影响，参与生物体内的生命过程，磷酸阴离子浓度过高会导致肾脏疾病以及高磷血病。水生态系统中磷酸阴离子的浓度过高会导致水体的富营养化。因此发展磷酸二氢根阴离子的检测方法对发展在水环境中具有高选择性的阴离子传感分子具有重要的意义。但是现有的磷酸阴离子传感器大多选择性较差，难于区分磷酸二氢根阴离子与醋酸根等其它阴离子(Chem.-Eur.J.2008,14,9065-9073)。因此合成新型的磷酸二氢根阴离子荧光探针，无论在化学应用还是理论研究上都是十分重要的挑战，本发明设计合成的罗丹明6G内酰胺萘基衍生物对于磷酸二氢根有很好地选择性，在离子检测领域以及生物领域展示了重要的应用前景。
【发明内容】
本发明的目的是针对上述技术分析和存在问题，提供一种用于磷酸二氢根离子检测的荧光分子探针试剂以及制备方法。
本发明的技术方案：
一种用于磷酸二氢根离子检测的荧光分子探针试剂RH-nap，为罗丹明6G内酰胺萘基衍生物，其化学式为C37H34N4O2S，结构式为：
一种所述用于磷酸二氢根离子检测的荧光分子探针试剂的制备方法，步骤如下：
1)罗丹明6G内酰胺的制备
罗丹明6G溶于甲醇中，回流0.5小时，通入氨气，继续回流反应0.5小时，冷却至室温，减压抽滤，用甲醇洗涤2～3次，得粉红色固体罗丹明6G内酰胺。
2)罗丹明6G内酰胺萘基衍生物的制备
罗丹明6G内酰胺溶于干燥的N,N-二甲基甲酰胺，加入氢化钠冰浴下反应0.5小时，以1mL/min的速度将1-萘异硫氰酸酯的N,N-二甲基甲酰胺溶液滴入，搅拌至完全溶解，升温至室温继续反应2小时。将反应液以2mL/min的速度滴入250mL蒸馏水中，用二氯甲烷萃取2～3次，合并有机层，干燥、过滤、减压蒸馏浓缩至0.2mol/L，静置析出黄色固体，抽滤，二氯甲烷洗涤沉淀，真空干燥，得到罗丹明6G内酰胺萘基衍生物。
所述罗丹明6G、甲醇和氨气的用量比为1mol:9L:100m3。
所述罗丹明6G内酰胺、N,N-二甲基甲酰胺、氢化钠和1-萘异硫氰酸酯的用量比为1mol:8L:1mol:1mol。
所述N,N-二甲基甲酰胺反应液与蒸馏水的容积比为1:5。
本发明的优点是：本发明制备的罗丹明6G萘基衍生物，合成简单方便，产率高，易于制备，适于放大合成及实际生产应用。其作为新型磷酸二氢根阴离子荧光探针可以应用于生物以及离子检测领域。采用荧光光谱监测手段，探针分子在乙腈和水混合溶液中显示对于磷酸二氢根离子的专一性识别且灵敏度高，具有广阔的应用前景。
【附图说明】
图1为该荧光离子探针试剂的合成路线示意图。
图2为10μM的RH-nap的乙腈和水体积比1:1混合溶液中加入当量不同阴离子后的荧光发射光谱。
图3为10μM的RH-nap的乙腈和水体积比1:1混合溶液中逐步加入磷酸二氢根离子后的荧光发射光谱。
【具体实施方式】
实施例：
1)罗丹明6G内酰胺中间体的制备
将6.0g(13.5mmol)罗丹明6G溶于120mL甲醇中，回流0.5小时，通入1.4L氨气，继续回流反应0.5小时。冷却至室温，减压抽滤，用甲醇洗涤2～3次，得粉红色固体罗丹明6G内酰胺，收率82.4％。
2)罗丹明6G内酰胺萘基衍生物的制备
2.0g(4.8mmol)罗丹明6G内酰胺溶于40mL干燥的N,N-二甲基甲酰胺，加入0.12g(4.8mmol)氢化钠冰浴下反应0.5小时。0.89g(4.8mmol)1-萘异硫氰酸酯溶于10mL干燥的N,N-二甲基甲酰胺，以1mL/min的速度将1-萘异硫氰酸酯的N,N-二甲基甲酰胺溶液滴入，升温至室温继续反应2小时。将反应液以2mL/min的速度滴入250mL水中，用二氯甲烷萃取2～3次，合并有机层，干燥、过滤、减压蒸馏浓缩至0.2mol/L，静置析出黄色固体，抽滤，二氯甲烷洗涤沉淀，真空干燥，得到罗丹明6G内酰胺萘基衍生物，收率47.1％。熔点：227.2～231.5℃。1H NMR(CD3SOCD3,500MHz,TMS):δ＝1.20(t,6H,J＝7Hz)；1.88(s,6H)；3.12-3.07(m,4H)；4.96(t,2H)；6.17(s,2H)；6.40(s,2H)；6.98-6.97(d,1H,J＝9Hz)；7.42-7.39(t,1H,J＝7.5Hz)；7.51-7.45(m,3H)；7.59(t,1H,J＝7.5Hz)；7.65-7.54(d,1H,J＝7.5Hz)；7.69-7.67(d,1H,J＝8.5Hz)；7.84-7.82(m,1H)；8.04-8.03(d,1H,J＝7Hz)；12.30(s,1H).13C NMR(CD3SOCD3,500MHz,TMS):δ＝14.70,17.33,37.93,55.30,69.41,96.08,107.04,117.88,123.07,124.41,124.71,125.24,125.86,126.54,126.08,127.09,127.62,128.60,129.25,129.36,134.20,134.85,135.68,147.75,151.02,155.08,169.64,179.47.2)。
本发明的具体应用及效果如下：
RH-nap配成10μM的乙腈-水体积比1:1的溶液，用荧光分光光度计对其识别H2PO4 -性能进行了研究。当量加入不同的阴离子(F-，Cl-，Br-，I-，AcO-，CN-，HSO4 -，H2PO4 -，NO3 -)，如图2所示，只有在H2PO4 -存在时，荧光探针RH-nap的螺环打开，于561nm处出现很强的荧光发射峰，溶液颜色变成粉红色，而在等量的其它阴离子(F-，Cl-，Br-，I-，AcO-，CN-，HSO4 -，NO3 -)存在下荧光强度及溶液颜色均没有明显变化。如图3所示，在RH-nap配成10μM的乙腈-水体积比1:1的溶液中，分别加入不同当量的H2PO4 -(0，0.1，0.2，0.3，0.4，0.5，0.6，0.7，0.8，0.9，1.0，1.1，1.2，1.5，1.75，2.0，2.25，2.5当量)，随着H2PO4 -的浓度上升，溶液在558nm处的荧光发射峰强度不断增加，同时溶液颜色也由无色变成粉红色，说明RH-nap对于磷酸二氢根阴离子有很好的识别能力。
Claims (7)
1.一种用于磷酸二氢根离子检测的荧光分子探针试剂RH-nap，其特征在于，该探针试剂RH-nap为罗丹明6G内酰胺萘基衍生物，其化学式为C37H34N4O2S，结构式为：
。
2.一种如权利要求1所述用于磷酸二氢根离子检测的荧光分子探针试剂RH-nap的制备方法，其特征在于包括下述步骤：
1)罗丹明6G内酰胺的制备
罗丹明6G溶于甲醇中，回流0.5小时，通入氨气，继续回流反应0.5小时，冷却至室温，减压抽滤，用甲醇洗涤2～3次，得粉红色固体罗丹明6G内酰胺，罗丹明6G的结构式为：
2)罗丹明6G内酰胺萘基衍生物的制备
罗丹明6G内酰胺溶于干燥的N,N-二甲基甲酰胺，加入氢化钠冰浴下反应0.5小时，以1mL/min的速度将1-萘异硫氰酸酯的N,N-二甲基甲酰胺溶液滴入，搅拌至完全溶解，升温至室温继续反应2小时，将反应液以2mL/min的速度滴入250mL蒸馏水中，用二氯甲烷萃取2～3次，合并有机层，干燥、过滤、减压蒸馏浓缩至0.2mol/L，静置析出黄色固体，抽滤，二氯甲烷洗涤沉淀，真空干燥，得到罗丹明6G内酰胺萘基衍生物，即荧光分子探针试剂RH-nap。
3.根据权利要求2所述用于磷酸二氢根离子检测的荧光分子探针试剂RH-nap的制备方法，其特征在于：所述罗丹明6G、甲醇和氨气的用量比为1mol:9L:100m3。
4.根据权利要求2所述用于磷酸二氢根离子检测的荧光分子探针试剂RH-nap的制备方法，其特征在于：所述罗丹明6G内酰胺、N,N-二甲基甲酰胺、氢化钠和1-萘异硫氰酸酯的用量比为1mol:8L:1mol:1mol。
5.根据权利要求2所述用于磷酸二氢根离子检测的荧光分子探针试剂RH-nap的制备方法，其特征在于：所述N,N-二甲基甲酰胺反应液与蒸馏水的容积比为1:5。
6.根据权利要求2所述用于磷酸二氢根离子检测的荧光分子探针试剂RH-nap的制备方法，其特征在于其制备步骤如下：取2.0g罗丹明6G内酰胺溶于40mL干燥的N,N-二甲基甲酰胺，加入0.12g氢化钠冰浴下反应0.5小时，0.89g的1-萘异硫氰酸酯溶于10mL干燥的N,N-二甲基甲酰胺，以1mL/min的速度将1-萘异硫氰酸酯的N,N-二甲基甲酰胺溶液滴入，升温至室温继续反应2小时，将反应液以2mL/min的速度滴入250mL水中，用二氯甲烷萃取2～3 次，合并有机层，干燥、过滤、减压蒸馏浓缩至0.2mol/L，静置析出黄色固体，抽滤，二氯甲烷洗涤沉淀，真空干燥，得到罗丹明6G内酰胺萘基衍生物，即荧光分子探针试剂RH-nap，收率47.1％。
7.一种如权利要求1所述用于磷酸二氢根离子检测的荧光分子探针试剂RH-nap作为检测磷酸二氢根离子的用途。
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