CN109134452A - 一种荧光探针及其制备和应用 - Google Patents
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Abstract
本发明涉及一种荧光探针及其制备和应用,探针结构如式I。制备:将5,7‑二醛基‑8‑羟基喹啉和2‑氨基硫酚溶于溶剂中,回流反应,提纯,即得。本发明的荧光探针合成简单,反应产率高,对镉离子具有高度选择性,其它常见离子都无明显干扰;可在生理pH 7.4的水溶液环境条件下工作,具有在生物荧光成像中的应用前景。
Description
技术领域
本发明属于探针及其制备和应用领域,特别涉及一种荧光探针及其制备和应用。
背景技术
镉离子是典型的有毒重金属离子,可造成生物体神经系统的永久性损伤。重金属污染已成为目前环境污染中的重大污染源之一,因此发展镉离子的选择性检测方法,对水体环境中重金属污染的监测具有重要意义。分子荧光探针法具有简单快速、灵敏度高、选择性好、易于实现自动化和可视化成像等特点而备受关注。但由于重金属离子固有的猝灭荧光发射的性质,使得发展荧光增强型荧光探针依然具有一定挑战性。8-羟基喹啉荧光染料对重金属离子具有强的络合能力,在发展重金属离子荧光探针方面得到了广泛研究。但已报道的8-羟基喹啉荧光探针的选择性较差,多种金属离子均可造成荧光信号的改变。
发明内容
本发明所要解决的技术问题是提供一种荧光探针及其制备和应用,克服了现有技术中现有8-羟基喹啉荧光探针的选择性较差,多种金属离子均可造成荧光信号的改变的缺陷,本发明所涉及的荧光探针是通过在8-羟基喹啉结构中引入苯并噻唑基调控选择性,得到的荧光探针对镉离子具有高选择性,合成简单收率高,可在生理pH 7.4的水溶液环境条件下工作,具有生物荧光成像和环境水样中镉离子的高选择性荧光检测的应用前景。
本发明的一种结构如式I的荧光探针:
本发明的一种所述荧光探针的制备方法,步骤包括:
(1)将8-羟基喹啉和六次甲基四胺溶于溶剂中,回流反应,旋转蒸发,提纯,得到5,7-二醛基-8-羟基喹啉;
(2)将5,7-二醛基-8-羟基喹啉和2-氨基硫酚溶于溶剂中,回流反应,提纯,即得荧光探针。上述制备方法的优选方式如下:
所述步骤(1)中8-羟基喹啉、六次甲基四胺、溶剂的质量体积比为1g:1.5-3g:5-15mL。进一步优选8-羟基喹啉、六次甲基四胺、溶剂的质量体积比为1g:2g:10ml。
所述步骤(1)中溶剂为三氟乙酸。
所述步骤(1)中回流温度为110℃,时间为36-72h。优选时间为72h。
所述步骤(1)中提纯为稀盐酸洗涤,过滤,水洗至中性。所述稀盐酸的浓度为0.5M。
所述步骤(2)中5,7-二醛基-8-羟基喹啉、2-氨基硫酚、溶剂的质量体积比为1g:1-2g:500-1000mL。
进一步优选5,7-二醛基-8-羟基喹啉、2-氨基硫酚、溶剂的质量体积比为1g:1.5g:800mL。所述步骤(2)中溶剂为乙醇。
所述步骤(2)中回流反应温度为80℃,时间为36-72h。优选时间为72h。
所述步骤(2)中提纯为抽滤,乙醇洗涤提纯。
本发明的一种所述荧光探针的应用。
所述应用包括:
利用荧光探针溶液,测试526nm处的荧光强度,并利用标准曲线获得镉离子的浓度。
镉离子溶液的检测限为0-5μM。
标准曲线具体为:将呈梯度变化的镉离子的水溶液分别加入荧光探针的pH=7.4的Tris-HCl缓冲溶液中,以镉离子浓度为横坐标,荧光强度的变化为纵坐标作图,得到线性工作曲线。
荧光探针的激发波长313nm,发射波长526nm。
本发明的一种荧光探针的应用,如应用于生物荧光成像、在环境水样分析。
有益效果
本发明的荧光探针是8-羟基喹啉类衍生物,原料廉价,制备方法简单,收率高,达到79%;
本发明的荧光探针选择性高,对镉离子具有高度选择性,其它常见离子都无明显干扰(参见图2);可在pH7.4的生理环境条件下工作,具有应用于生物荧光成像和在环境水样分析中的前景;
本发明荧光探针对镉离子的检测线性范围宽为0-5μM,检测灵敏度高,检测限为0.1μM,较文献中的0.6μM低(Cheng,T.;Xu,Y.;Zhang,S.;Zhu,W.;Qian,X.;Duan,L.J.Am.Chem.Soc.2008,130,16160)。
附图说明
图1为本发明所涉及的反应型荧光探针的合成路线;
图2为本发明所涉及的荧光探针对镉离子的选择性响应荧光光谱图;
图3为本发明涉及的荧光探针随镉离子浓度变化的荧光光谱图;
图4为本发明涉及的荧光探针的荧光强度变化与镉离子浓度之间的线性关系。
具体实施方式
下面结合具体实施例,进一步阐述本发明。应理解,这些实施例仅用于说明本发明而不用于限制本发明的范围。此外应理解,在阅读了本发明讲授的内容之后,本领域技术人员可以对本发明作各种改动或修改,这些等价形式同样落于本申请所附权利要求书所限定的范围。
实施例1
荧光探针的合成:
(1)5,7-二醛基-8-羟基喹啉的合成:8-羟基喹啉(1.0g)和六次甲基四胺(2.0g)溶于三氟乙酸(10.0mL)中,在110℃回流反应72h,旋转蒸发除去溶剂,稀盐酸洗涤,过滤,水洗固体至中性,真空干燥,得到5,7-二醛基-8-羟基喹啉,产率82%。
1H NMR(400MHz,DMSO),δ(ppm):10.46(s,1H),10.04(s,1H),9.83(dd,J=1.44,8.59Hz,1H),8.97(dd,J=1.44,4.72Hz,1H),8.40(s,1H),8.05(dd,J=4.73,8.60Hz,1H);13C NMR(100MHz,DMSO),δ(ppm):191.75,188.03,166.85,145.10,139.27,138.28,138.16,130.36,126.77,119.13,116.67.ESI-MS:m/z cald for C11H7NO3,201.18;found:[M-H]-:200.1.
(2)荧光探针的合成:5,7-二醛-8-羟基喹啉(0.1g)和邻氨基苯硫酚(0.15g)溶于80mL乙醇,N2保护下,在85℃回流反应72h,冷却至室温,过滤,所得固体用热乙醇洗3次,真空干燥,即得目标产物,产率为79%。
1H NMR(400MHz,CDCl3),δ(ppm):9.88(d,1H),9.20(d,1H),8.58(s,1H),8.17(t,J=8.12,8.12Hz,2H),8.00(d,J=7.99Hz,2H),7.82(dd,J=4.42Hz,1H),7.60(dd,J=7.38,15.00Hz,2H),7.50(t,2H);MALDI-TOF-MS:m/z calculated for C23H13N3OS2,411.51,Found411.68.
荧光探针的合成路线如图1所示。
实施例2
荧光探针对镉离子荧光检测的选择性:
采用pH=7.4的Tris-HCl缓冲溶液控制实验条件。
在不同10ml比色管中分别依次加入0.1ml荧光探针的二甲亚砜溶液(1mM),2mL待测金属离子水溶液(金属离子浓度均为1mM),用Tris-HCl缓冲溶液定容至10mL,放置1小时。将3mL工作液转移至1cm荧光比色皿中测定荧光光谱,激发波长为313nm。空白实验为上述溶液中不加任何金属离子。对镉离子的选择性检测如图2所示。可见荧光仅在镉离子存在下显著增强,表明了本发明所涉及的荧光探针对镉离子的高度选择性。
实施例3
荧光探针对镉离子的定量荧光检测:
在不同10ml比色管中分别依次加入0.1mL荧光探针的二甲亚砜溶液(1mM),0-0.1mL不同体积的1mM的镉离子水溶液,并用Tris-HCl缓冲溶液定容至10mL,放置1h。定容后荧光探针的浓度为10 μM,镉离子浓度为0-10μM。将3mL工作液转移至1cm荧光比色皿中记录荧光光谱并读取记录526nm处的荧光强度。将荧光强度和相应镉离子浓度数据输入软件Origin8进行拟合,在镉离子浓度为0-5μM范围内得一线性工作曲线,回归方程为Y=1.75309×1011X+149270.0393,Y为荧光强度,X为镉离子浓度,线性回归常数为0.9962,表明探针可定量检测镉离子的浓度。随镉离子浓度变化的荧光光谱变化以及相应线性关系分别如图3和4所示。
实施例4
实际水样中镉离子荧光检测的回收率:
在10ml比色管中分别依次加入0.1mL荧光探针的二甲亚砜溶液(1mM),1mL自来水,0.03mL的1mM的镉离子水溶液,并用Tris-HCl缓冲溶液定容至10ml,放置1h。定容后荧光探针的浓度为10 μM,镉离子浓度为3μM。将3mL工作液转移至1cm荧光比色皿中记录荧光光谱并读取记录526nm处的荧光强度,并根据实施例3中所得回归方程计算镉离子的浓度为2.92μM(平行测定三次),相对标准偏差为0.7%,回收率为97.3%。
Claims (10)
1.一种结构如式I的荧光探针:
2.一种如权利要求1所述荧光探针的制备方法,步骤包括:
(1)将8-羟基喹啉和六次甲基四胺溶于溶剂中,回流反应,旋转蒸发,提纯,得到5,7-二醛基-8-羟基喹啉;
(2)将5,7-二醛基-8-羟基喹啉和2-氨基硫酚溶于溶剂中,回流反应,提纯,即得荧光探针。
3.根据权利要求2所述的制备方法,其特征在于,所述步骤(1)中8-羟基喹啉、六次甲基四胺、溶剂的质量体积比为1g:1.5-3g:5-15mL。
4.根据权利要求2所述的制备方法,其特征在于,所述步骤(1)中溶剂为三氟乙酸。
5.根据权利要求2所述的制备方法,其特征在于,所述步骤(1)中回流温度为110℃,时间为36-72h。
6.根据权利要求2所述的制备方法,其特征在于,所述步骤(2)中5,7-二醛基-8-羟基喹啉、2-氨基硫酚、溶剂的质量体积比为1g:1-2g:500-1000mL。
7.根据权利要求2所述的制备方法,其特征在于,所述步骤(2)中回流反应温度为80℃,时间为36-72h。
8.一种权利要求1所述荧光探针的应用。
9.根据权利要求8所述的应用,其特征在于,包括:
利用荧光探针溶液,测试526nm处的荧光强度,并利用标准曲线获得镉离子的浓度。
10.根据权利要求8所述的应用,其特征在于,镉离子溶液的检测范围为0-5μM,检测限为0.1μM。
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