CN110272430B - 一种水溶液中耐酸性光控荧光分子开关及其合成方法 - Google Patents

一种水溶液中耐酸性光控荧光分子开关及其合成方法 Download PDF

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CN110272430B
CN110272430B CN201810217744.7A CN201810217744A CN110272430B CN 110272430 B CN110272430 B CN 110272430B CN 201810217744 A CN201810217744 A CN 201810217744A CN 110272430 B CN110272430 B CN 110272430B
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徐兆超
李锦�
祁清凯
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Abstract

本发明提供一种水溶液中耐酸性光控荧光分子开关及其合成方法。该分子开关具体分子结构以3‑氨基或3‑乙酰氨基取代的罗丹明螺酰胺为基本结构单元，其结构式如(1)所示。本发明里开发的3‑氨基或3‑乙酰氨基取代的罗丹明螺酰胺不仅具有耐酸的性能，而且保留了一定的水溶性。因此这类水中耐酸的染料可以应用于生物传感检测及荧光成像领域中且不受生物环境的pH干扰。

Description

一种水溶液中耐酸性光控荧光分子开关及其合成方法
技术领域
本发明属于分子开关领域，具体涉及一种水溶液中耐酸性光控荧光分子开关及其合成方法。
背景技术
罗丹明类荧光染料具有摩尔消光系数高、荧光量子产率高、光稳定性好、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，在有机染料领域占有极其重要的地位，而其在荧光探针领域应用尤为广泛。其中，罗丹明螺酰胺的“开-关”机理常被用作金属阳离子(Mn+)荧光探针，闭合时没有吸收，也没有荧光，选择性识别特定金属阳离子后，探针的螺环被打开而产生吸收和强荧光。
罗丹明螺酰胺能够在溶液中对金属阳离子进行高选择性和灵敏检测，这对生物成像来说具有极其重要的意义。但是，这类分子还存在一个缺点，严重限制了其在荧光染料领域的应用，那就是质子酸(H+)同样能够打开罗丹明酰胺螺环，这就会对实验结果造成很大干扰。细胞内存在许多偏酸性的环境(如溶酶体、酸性蛋白等)，当罗丹明螺酰胺染料用于这些酸性环境中时，其酸开环产生的荧光信号会严重干扰检测结果甚至导致检测结果完全错误，因此在酸性环境中基于这类染料的荧光探针目前仍无法精确检测金属阳离子，并进一步将其应用于生物及化学物质的传感及检测等诸多领域。综上所述，开发耐酸性的罗丹明螺酰胺类荧光开关染料对于生物及化学物质的传感检测及荧光成像显得尤为迫切和重要。
发明内容
本发明提供了一种水溶液中耐酸性光控荧光分子开关及其合成方法，该分子开关以罗丹明3-氨基或3-乙酰氨基的螺酰胺染料为结构单元，研究发现这类开关染料在有机相和水相中都具有耐酸的特性，即表现为在酸性环境中螺酰胺部分遇质子进攻时不发生开环异构反应，能够大大降低酸性环境中的背景荧光干扰，保持无荧光状态。因此这类染料在生物及化学物质的传感及检测等诸多领域具有潜在的巨大的应用前景。
本发明所述的一种水溶液中耐酸性光控荧光分子开关，其结构式如下所示：
Figure BDA0001598991340000021
其中，R1为H或CO CH3、R2为H或CH3。
一种水溶液中耐酸性光控荧光分子开关，其特征在于：其结构式如下之一所示：
Figure BDA0001598991340000022
本发明还给出了所述一种水溶液中耐酸性光控荧光分子开关的合成方法，合成路线如下：
Figure BDA0001598991340000023
具体的合成步骤为：
(1)将3-硝基罗丹明和氨基六聚乙二醇或氨基六聚乙二醇单甲醚按物质的量比1:1-20溶解于无水乙醇，升温至回流，搅拌1-4小时后减压蒸除溶剂，中间体罗丹明3-硝基六聚乙二醇酰胺通过硅胶柱色谱分离提纯；
(2)取上述步骤(1)中产物罗丹明3-硝基六聚乙二醇酰胺全部溶于体积比为1-5:1甲醇和二氯甲烷混合溶剂，在氢气氛围及占反应物质量百分比0.5-10％的钯碳催化下搅拌1-3小时，抽滤并取滤液，减压蒸除溶剂后得到罗丹明3-氨基六聚乙二醇酰胺产物；
(3)取上述步骤(2)中产物罗丹明3-氨基六聚乙二醇酰胺和乙酰氯或碘甲烷按物质的量比1:1-30溶解于无水二氯甲烷，常温搅拌1-3小时后减压蒸除溶剂，最后将罗丹明3-甲氨基或乙酰基取代的六聚乙二醇酰胺产物通过柱色谱分离提纯。
一种水溶液中耐酸性光控荧光分子开关的应用，基于其合成方法及水中耐酸优点并作为荧光开关染料应用在生物荧光成像领域或被作为荧光探针分子用于生物及化学物质的传感及检测等诸多领域。
传统的罗丹明螺酰胺可以与金属阳离子发生作用，致使螺环打开，实现暗态到亮态的转变，达到选择性检测的目的。然而质子的存在会对金属阳离子的检测产生巨大干扰，导致结果不可信；生物环境普遍存在pH小于7的酸性环境，在酸性环境中这类染料发生酸开环过程会导致其数据失真。因此这类染料在酸性环境中无法应用于生物及化学物质的传感及检测领域。
而本发明里开发的3-氨基或3-乙酰氨基取代的罗丹明螺酰胺不仅具有耐酸的性能，而且保留了一定的水溶性(如图6所示)。因此这类水中耐酸的染料可以应用于生物传感检测及荧光成像领域中且不受生物环境的pH干扰。
附图说明
图1：为实施例1中的水溶性产物(P1)的核磁氢谱。
图2：为实施例2中的水溶性产物(P2)的核磁氢谱。
图3：为实施例3中的水溶性产物(P3)的核磁氢谱。
图4：为实施例1中的水溶性产物(P1)在不同pH值的缓冲溶液(浓度为10-5M)中测得的紫外可见吸收及荧光光谱。
图5：为实施例3中的水溶性产物(P3)在不同pH值的缓冲溶液(浓度为10-5M)中测得的紫外可见吸收及荧光光谱。
图6：金属离子诱导的耐酸性3-伯胺或仲胺取代的罗丹明螺酰胺分子的螺环及荧光开关的示意图。
具体实施方式
本发明给出了一类水溶液中耐酸性光控荧光分子开关的合成方法及其作为荧光开关染料应用在生物荧光成像领域或被作为荧光探针分子用于生物及化学物质的传感及检测等诸多领域。
实施例1
当R1＝R2＝H时，其分子(P1)合成路线和产物结构如下：
Figure BDA0001598991340000041
合成步骤及表征：将3-硝基罗丹明(2mmol，0.974g)和氨基六聚乙二醇(2mmol，0.562g)溶于无水乙醇(5mL)，升温至78℃回流，搅拌4小时后减压蒸除溶剂，产物通过柱色谱(硅胶，二氯甲烷/甲醇，10:1v/v)分离提纯得到的浅黄色粘性液体(1.42g，95％)。接着将该液体产物全部溶于甲醇(5mL)，在氢气氛围及钯碳(10％wt)催化下搅拌1小时，抽滤并取滤液，减压蒸除溶剂后得到最终白色粘性液体产物P1(1.35g，99％)。
产物进行了核磁(图1)和质谱的表征：1H NMR(400MHz,CDCl3)δ7.14(t,J＝7.7Hz,1H),6.58–6.50(m,3H),6.38–6.26(m,5H),3.74–3.70(m,2H),3.67–3.56(dd,J＝16.6,8.3Hz,16H),3.51–3.47(m,2H),3.39–3.26(m,12H),3.17–3.09(m,4H),1.16(t,J＝7.0Hz,12H)。13C NMR(101MHz,CDCl3)δ169.84,155.00,152.99,148.64,145.12,133.59,128.88,113.41,112.01,108.03,106.16,97.98,97.65,72.62,72.60,70.45,70.38,70.37,70.28,70.25,70.13,69.93,69.90,68.07,64.55,61.50,44.33,12.61。LC-MS(ESI)：m/z：计算值：720.4098，实验值：721.4183[M+H]+。
经上述检测，鉴定其结构为P1所示。
将P1溶解于不同pH值的缓冲溶液(浓度为10-5M)中，并测试其在不同pH下的紫外可见吸收光谱和荧光光谱(图4)。如图4，两分子在pH为酸性的缓冲溶液中并没有出现罗丹明的特征吸收峰和发射峰，这表明分子在酸性环境中闭环螺酰胺结构没有发生改变，进一步证明了两分子在水中具有耐酸性的特征。
实施例2
当R1＝H，R2＝CH3时，其分子(P2)合成路线和产物结构如下：
Figure BDA0001598991340000051
合成步骤及表征：3-硝基罗丹明(0.24g，0.5mmol)和氨基六聚乙二醇甲醚(0.14g，0.5mmol)溶于无水乙醇(8mL)中，升温至78℃回流，搅拌4小时后减压蒸除溶剂，残余物通过柱色谱(硅胶，乙酸乙酯/甲醇，30:1v/v)分离得到粘性液体(0.34g，90％)。将其全部溶于甲醇(5mL)并加入20mg 10％钯碳在氢气氛围下催化还原。反应混合物抽滤，滤液通过减压蒸除溶剂，产物通过柱色谱(硅胶，乙酸乙酯/甲醇，20:1v/v)分离得到粘性液体P2(0.32g，96％)。
产物进行了核磁(图2)和质谱的表征：1H NMR(400MHz,CDCl3)δ7.11(t,J＝7.7Hz,1H),6.54(t,J＝8.9Hz,3H),6.35(d,J＝2.4Hz,2H),6.32–6.23(m,3H),5.37(s,2H),3.67–3.51(m,16H),3.51–3.46(m,2H),3.41–3.25(m,15H),3.13(t,J＝7.2Hz,2H),1.15(t,J＝7.0Hz,12H)。13C NMR(101MHz,CDCl3)δ169.55,154.76,152.76,148.38,144.91,133.28,128.65,113.20,113.08,111.69,107.79,106.04,97.44,71.66,70.32,70.27,70.24,70.24,70.22,70.11,69.70,67.85,64.26,58.74,44.09,38.56,12.38。LC-MS(ESI)：m/z：计算值：734.4255；实验值：735.4290[M+H]+。
经上述检测，鉴定其结构为P2所示。
将P2溶解于不同pH值的缓冲溶液(浓度为10-5M)中，并测试其在不同pH下的紫外可见吸收光谱和荧光光谱。结果显示：两分子在pH为酸性的缓冲溶液中并没有出现罗丹明的特征吸收峰和发射峰，这表明分子在酸性环境中闭环螺酰胺结构没有发生改变，进一步证明了两分子在水中具有耐酸性的特征。
实施例3
当R1＝COCH3，R2＝CH3时，其分子(P3)合成路线和产物结构如下：
Figure BDA0001598991340000061
合成步骤及表征：将P2(0.22g，0.3mmol)和乙酰氯(35mg，0.45mmol)混合于二氯甲烷(5mL)中，搅拌2小时后减压蒸除溶剂并通过柱色谱(硅胶，乙酸乙酯/甲醇，20:1v/v)分离得到粘性液体P3(0.22g，95％)。
产物进行了核磁(图3)和质谱的表征：1H NMR(400MHz,CDCl3)δ10.47(s,1H),8.39(d,J＝8.2Hz,1H),7.34(t,J＝7.9Hz,1H),6.68(d,J＝7.6Hz,1H),6.41(d,J＝8.8Hz,2H),6.33(d,J＝2.4Hz,2H),6.24(dd,J＝8.9,2.4Hz,2H),3.60–3.48(m,16H),3.47–3.42(m,2H),3.35–3.25(m,15H),3.08(t,J＝7.1Hz,2H),2.25(s,3H),1.13(t,J＝7.0Hz,13H)。13CNMR(101MHz,CDCl3)δ169.06,168.82,153.52,152.97,148.66,136.57,133.85,128.43,117.79,117.38,115.71,107.90,104.58,97.56,71.69,70.34,70.30,70.11,69.82,67.62,64.95,58.78,44.15,38.83,24.73,12.38。LC-MS(ESI)：m/z：计算值：776.4360；实验值：777.4435[M+H]+。
经上述检测，鉴定其结构为P3所示。
将P3溶解于不同pH值的缓冲溶液(浓度为10-5M)中，并测试其在不同pH下的紫外可见吸收光谱和荧光光谱(图5)。如图5所示，两分子在pH为酸性的缓冲溶液中并没有出现罗丹明的特征吸收峰和发射峰，这表明分子在酸性环境中闭环螺酰胺结构没有发生改变，进一步证明了两分子在水中具有耐酸性的特征。

Claims (4)

1.一种水溶液中耐酸性光控荧光分子开关，其特征在于：其结构式如下所示，
Figure FDA0002982730300000011
其中，R1为H或COCH3、R2为H或CH3。
2.根据权利要求1所述的一种水溶液中耐酸性光控荧光分子开关，其特征在于：其结构式如下之一所示：
Figure FDA0002982730300000012
3.根据权利要求1所述水溶液中耐酸性光控荧光分子开关的合成方法，其特征在于：该合成方法的具体步骤如下：
(1)将3-硝基罗丹明和氨基六聚乙二醇或氨基六聚乙二醇单甲醚按物质的量比1:1-20溶解于无水乙醇，升温至回流，搅拌1-4小时后减压蒸除溶剂，中间体罗丹明3-硝基六聚乙二醇酰胺通过硅胶柱色谱分离提纯；
(2)取上述步骤(1)中产物罗丹明3-硝基六聚乙二醇酰胺全部溶于体积比为1-5:1甲醇和二氯甲烷混合溶剂，在氢气氛围及占反应物质量百分比0.5-10％的钯碳催化下搅拌1-3小时，抽滤并取滤液，减压蒸除溶剂后得到罗丹明3-氨基六聚乙二醇酰胺产物；
(3)取上述步骤(2)中产物罗丹明3-氨基六聚乙二醇酰胺和乙酰氯按物质的量比1:1-30溶解于无水二氯甲烷，常温搅拌1-3小时后减压蒸除溶剂，最后将产物乙酰基取代的六聚乙二醇酰胺产物通过柱色谱分离提纯。
4.根据权利要求1所述的水溶液中耐酸性光控荧光分子开关在制备分子探针及荧光传感的制剂中的应用。
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