CN107474055B - 基于罗丹明-吲哚衍生物的荧光探针及其制备方法和应用 - Google Patents
基于罗丹明-吲哚衍生物的荧光探针及其制备方法和应用 Download PDFInfo
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Abstract
本发明提供了一种基于罗丹明‑吲哚衍生物的荧光探针及其制备方法和应用，其中所述罗丹明‑吲哚衍生物的化学结构式如下：本发明的罗丹明‑吲哚衍生物能选择性的与二价钯离子作用，荧光由蓝色变为桔黄色，具有比率荧光效应，可实现裸眼辨别检测，特别是作为荧光探针在细胞内钯离子的方便检测的应用。
Description
技术领域
本发明属于有机合成领域，具体涉及基于罗丹明-吲哚衍生物的荧光探针及其制备方法和应用。
背景技术
钯是重要的催化剂，在精细化学品合成过程中起着十分重要的作用。但体内的钯离子可以与DNA，含硫醇的氨基酸，蛋白质和维生素B6作用，从而导致疾病。此外，由于钯离子大量地使用，使得钯也成为一个重要的金属污染物。鉴于其对生命和环境的重要性，科学家们一直致力于采用选择性荧光和荧光传感探针实现对钯离子在生物和环境系统中检测的研究。
近年来，分子探针技术由于具有灵敏度高、操作简单、成本低等特点，已经成为检测金属离子污染的重要手段。罗丹明衍生物具有较大的摩尔消光系数，在可见光区域内具有较长的发射和吸收波长等特点，在重金属离子识别的领域得到越来越广泛的重视。
发明内容
基于金属钯离子能够使罗丹明酰腙衍生物内酰胺螺环开环，故罗丹明-吲哚衍生物具有较好的二价钯离子识别性能。本发明主要目的在于提供一种可检测二价钯离子的灵敏度高、选择性好的金属离子荧光探针；另一目的是提供该探针的制备方法和应用。
本发明的技术方案是，一种基于罗丹明-吲哚衍生物的荧光探针，所述罗丹明-吲哚衍生物具有如下结构式：
本发明还提供了一种基于罗丹明-吲哚衍生物的荧光探针的制备方法，具体制备方法如下：
S1：将吲哚-3-甲酸，1-乙基-(3-二甲基氨基丙基)碳二亚胺盐酸盐和4-二甲氨基吡啶首先用二氯甲烷溶解，再加入罗丹明B乙二胺,得到混合物；
S2：将S1所得混合物在常压下回流，反应时间10-15h，得到溶液；
S3：将S2所得溶液浓缩，硅胶柱层析得到基于所述罗丹明-吲哚衍生物的荧光探针。
3、根据权利要求2所述的基于罗丹明-吲哚衍生物的荧光探针的制备方法，其特征在于，S1中，所述吲哚-3-甲酸,1-乙基-(3-二甲基氨基丙基)碳二亚胺盐酸盐,4-二甲氨基吡啶和所述罗丹明B乙二胺摩尔比为1：1：1：1。
将吲哚-3-甲酸(1-10mmol)，1-乙基-(3-二甲基氨基丙基)碳二亚胺盐酸盐(1-10mmol)和4-二甲氨基吡啶(1-10mmol)溶于二氯甲烷(20-200ml)中，再加入罗丹明B乙二胺(1-10mmol)，常压回流12h，真空浓缩，硅胶柱层析法纯化[CH2Cl2/CH3OH＝100:1(v/v)]得到黄色固体即为目标产物，所述罗丹明-吲哚衍生物的荧光探针。
本发明还提供了上述罗丹明-吲哚衍生物的荧光探针一种用途，即在作为二价钯离子荧光探针方面的应用。
本发明还提供了一种用于检测水样中二价钯离子的荧光探针，所述荧光探针主要由上述罗丹明-吲哚衍生物组成。
本发明通过用吲哚修饰改性罗丹明衍生物制备罗丹明-吲哚衍生物荧光探针，合成简单，原料易得，在多种常见金属离子中，对二价钯离子表现出较高的选择性和识别性能，使含有二价钯离子的溶液由无色变为粉红色，可实现裸眼辨别检测，更为重要的是也可用于水样中钯离子的检测，具有快速、简便、灵敏度高、选择性强的特点，以及广泛的潜在应用价值。
附图说明
图1为本发明实施例1制得的罗丹明-吲哚衍生物荧光探针的核磁共振氢谱谱图；
图2为本发明实施例1制得的罗丹明-吲哚衍生物荧光探针的质谱谱图；
图3为本发明实施例1制得的罗丹明-吲哚衍生物荧光探针的乙腈/水(体积比9:1)溶液(5×10-6mol/L)对1当量不同金属离子(Ag+，Al3+，Au3+，Ca2+，Cd2+，Co2+，Cr3+，Cu2+，Fe3+，Hg2+，K+，Mg2+,Mn2+，Na+，Ni2+，Pb2+，Pd2+，Pt2+，Zn2+，5×10-6mol/L)的荧光光谱图；
图4为本发明实施例1制得的罗丹明-吲哚衍生物荧光探针的乙腈/水(体积比9:1)溶液(5×10-6mol/L)滴定不同浓度Pd2+的荧光光谱图；
图5在Hela细胞中，荧光探针与Pd2+的荧光成像图；Hela细胞用5×10-6mol/L荧光探针培育30分钟后加入2×10-5mol/L Pd2+，继续培育30分钟后使用Olympus FV500-IX70激光共聚焦显微镜进行荧光成像。
其中：a为荧光探针蓝色通道荧光成像图；b为荧光探针红色通道荧光成像图；c为荧光探针明场图；d为荧光探针明场图和荧光图叠加后的图片；e为荧光探针+Pd2+蓝色通道荧光成像图；f为荧光探针+Pd2+红色通道荧光成像图；g为荧光探针+Pd2+明场图；h为荧光探针+Pd2+明场图和荧光图叠加后的图片。
具体实施方式
下面结合附图和具体实施例进一步详细说明本发明，本发明实施例采用的试剂和原料为常规市场购买或参考文献合成得到。
实施例1：
罗丹明-吲哚衍生物的合成
将吲哚-3-甲酸(161mg,1mmol)，1-乙基-(3-二甲基氨基丙基)碳二亚胺盐酸盐(191mg,1mmol)和4-二甲氨基吡啶(122mg,1mmol)溶于二氯甲烷(20ml)中，再加入罗丹明B乙二胺(456mg，1mmol)，常压回流12h，真空浓缩，硅胶柱层析法纯化[CH2Cl2/CH3OH＝100:1(v/v)]得到黄色固体即为目标产物，目标产物的产率为69％。
罗丹明-吲哚衍生物核磁共振分析结果如下：
核磁共振氢谱：1H NMR(400MHz,d6-DMSO),δ(ppm):8.01-8.03(t,1H,NH),7.75-7.76(m,1H,Aryl-H),7.44-7.46(m,2H,Aryl-H),7.30-7.32(m,1H,Aryl-H),7.02-7.06(t,1H,Aryl-H),6.94-6.97(m,1H,Aryl-H),6.58-6.60(m,1H,Aryl-H),6.39-6.41(m,1H,Aryl-H),6.30-6.37(m,7H,Aryl-H),3.24-3.29(d,8H,4CH2),3.13-3.17(m,2H,CH2),2.92-2.97(m,2H,CH2),1.02-1.05(s,12H,4CH3).具体核磁共振氢谱图见图1。
质谱：ESI-MS:m/z＝625.84for[M-2H]+；641.82for[M+CH3]+.具体质谱谱图见图2。
实施例2
罗丹明-吲哚衍生物对二价钯离子的光学性质测定
将上述实施例1制得的罗丹明-吲哚衍生物作为探针在乙腈/水(体积比9：1)介质中配制成摩尔浓度为5×10-6mol/L的溶液，分别在含摩尔浓度为5×10-6mol/L的Ag+，Al3+，Au3+，Ca2+，Cd2+，Co2+，Cr3+，Cu2+，Fe3+，Hg2+，K+，Mg2+,Mn2+，Na+，Ni2+，Pb2+，Pd2+，Pt2+，Zn2+等金属离子的溶液中加入等量的上述探针溶液，采用荧光光谱仪对实施例1制得的罗丹明-吲哚衍生物进行荧光光谱分析，所得的荧光光谱图见图3。本发明实施例1制得的罗丹明-吲哚衍生物与二价钯离子作用在590nm处的发射峰明显上升，而410nm处的发射峰明显下降，同时365nm紫外灯下产生肉眼明显可见蓝色到桔黄色荧光颜色变化，可用于二价钯离子的快速检测。而本发明制得的罗丹明-吲哚衍生物对其它金属离子如Ag+，Al3+，Au3+，Ca2+，Cd2+，Co2+，Cr3+，Cu2+，Fe3+，Hg2+，K+，Mg2+,Mn2+，Na+，Ni2+，Pb2+，Pt2+，Zn2+等无明显荧光响应。
实施例3
浓度为5×10-6mol/L的罗丹明-吲哚衍生物作为荧光探针的乙腈/水(体积比9：1)溶液中分别加入浓度为0mol/L，5×10-7mol/L，1×10-6mol/L，1.5×10-6mol/L，2×10-6mol/L，2.5×10-6mol/L，3×10-6mol/L，3.5×10-6mol/L，4×10-6mol/L，4.5×10-6mol/L，5×10- 6mol/L，7.5×10-6mol/L，1×10-5mol/L，1.25×10-5mol/L，1.5×10-5mol/L的二价钯离子，采用荧光光谱仪对其分别进行荧光光谱分析，记录410和590nm处的荧光强度值，所得的荧光光谱图见图4。通过附图4可以看出，随着钯离子浓度增加，罗丹明-吲哚衍生物荧光探针在410nm荧光强度逐渐减弱，在590nm处的荧光强度逐渐增强，且吸收峰强度比值F590/F410与钯离子浓度在2×10-6-1×10-5mol/L范围内线性相关，检测限为1.1×10-6mol/L。
实施例4
罗丹明-吲哚衍生物荧光探针在细胞内钯离子的检测实验
Hela细胞用5×10-6M的上述实施例1制得的罗丹明-吲哚衍生物荧光探针培育0.5小时后加入Pd2+，继续培育0.5小时后使用Olympus FV500-IX70激光共聚焦显微镜进行荧光成像，获得在Hela细胞的荧光成像图，具体如图5所示，其中a为荧光探针蓝色通道荧光成像图；b为荧光探针红色通道荧光成像图；c为荧光探针明场图；d为荧光探针明场图和荧光图叠加后的图片；e为荧光探针+Pd2+蓝色通道荧光成像图；f为荧光探针+Pd2+红色通道荧光成像图；g为荧光探针+Pd2+明场图；h为荧光探针+Pd2+明场图和荧光图叠加后的图片。Hela细胞中加入上述罗丹明-吲哚衍生物蓝色通道有强荧光，红色通道有弱荧光；而再加入钯离子后，蓝色通道荧光强度明显减弱，红色通道荧光强度明显增强。故本发明实施例1制得的三氮唑酰腙衍生物可用于细胞中钯离子的荧光探针。
以上所述实施例仅是为充分说明本发明而所举的较佳的实施例，其保护范围不限于此。本技术领域的技术人员在本发明基础上所作的等同替代或变换，均在本发明的保护范围之内，本发明的保护范围以权利要求书为准。
Claims (5)
1.一种基于罗丹明-吲哚衍生物的荧光探针，其特征在于，所述罗丹明-吲哚衍生物具有如下结构式：
2.根据权利要求1所述的一种基于罗丹明-吲哚衍生物的荧光探针的制备方法，其特征在于，包括如下步骤：
S1：将吲哚-3-甲酸，1-乙基-(3-二甲基氨基丙基)碳二亚胺盐酸盐和4-二甲氨基吡啶首先用二氯甲烷溶解，再加入罗丹明B乙二胺,得到混合物；
S2：将S1所得混合物在常压下回流，反应时间10-15h，得到溶液；
S3：将S2所得溶液浓缩，硅胶柱层析得到基于所述罗丹明-吲哚衍生物的荧光探针。
3.根据权利要求2所述的基于罗丹明-吲哚衍生物的荧光探针的制备方法，其特征在于，S1中，所述吲哚-3-甲酸,1-乙基-(3-二甲基氨基丙基)碳二亚胺盐酸盐,4-二甲氨基吡啶和所述罗丹明B乙二胺摩尔比为1：1：1：1。
4.根据权利要求2所述的基于罗丹明-吲哚衍生物的荧光探针的制备方法，其特征在于，所述吲哚-3-甲酸(1-10mmol)，1-乙基-(3-二甲基氨基丙基)碳二亚胺盐酸盐(1-10mmol)和4-二甲氨基吡啶(1-10mmol)溶于二氯甲烷(20-200ml)中，再加入罗丹明B乙二胺(1-10mmol)，常压回流12h，真空浓缩，硅胶柱层析法纯化[CH2Cl2/CH3OH＝100:1(v/v)]得到黄色固体即为目标产物：罗丹明-吲哚衍生物的荧光探针。
5.权利要求1所述的罗丹明-吲哚衍生物作为荧光探针方便检测细胞中钯离子的应用。
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