CN110437219A - 一种检测粘度和二氧化硫双功能的荧光探针 - Google Patents

一种检测粘度和二氧化硫双功能的荧光探针 Download PDF

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CN110437219A
CN110437219A CN201910613686.4A CN201910613686A CN110437219A CN 110437219 A CN110437219 A CN 110437219A CN 201910613686 A CN201910613686 A CN 201910613686A CN 110437219 A CN110437219 A CN 110437219A
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战付旭
汲静静
张占明
郑庚修
王秋芬
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Abstract

本发明公开了一种检测粘度和二氧化硫双功能的荧光探针。该荧光探针随粘度的增加红色荧光逐渐增强，随SO2的增加蓝色荧光增强，显示出不同的荧光响应信号，从而实现区别检测。本发明的荧光探针在生物化学领域具有重要的应用价值。

Description

一种检测粘度和二氧化硫双功能的荧光探针
技术领域
本发明涉及分析化学领域，涉及一种检测粘度和二氧化硫的荧光探针的制备。
背景技术
二氧化硫(SO2)既是一种主要的大气污染物，又是一种有价值的商业试剂，由于矿物燃料的燃烧以及纸浆制造和金属加工等工业产品的燃烧，人类暴露于二氧化硫的范围越来越广。越来越多的医学研究证实，过度接触二氧化硫不仅可能引起呼吸道反应，而且还会引起肺癌、心血管疾病和一些神经系统疾病，如偏头痛和脑癌。内源性HSO3 -可由含硫醇的氨基酸如半胱氨酸和谷胱甘肽代谢生成。另外，二氧化硫(SO2)是一种重要的气体信号传递体，参与调节血管平滑肌张力、调节血胰岛素水平、降低血压以及维持生物硫平衡等生理过程。然而，内源性SO2的异常水平通常与各种疾病有关。
各种物质和信号传输现象以及分子间相互作用通常由粘度决定。在细胞内，粘度对细胞内物质和信号的传递、生物大分子之间的相互作用以及反应代谢物(如ROS和RNS)的扩散都有很大的影响。细胞液粘度的变化与多种疾病和病理有关。尤其是细胞质凝聚和细胞密度的增加是细胞凋亡的显著超微结构特征。
ROS可以通过氧化细胞组分来影响粘度，SO2在调节氧化还原状态对ROS起抗氧化作用，因此研究粘度和SO2之间关系对生命体系具有重大意义。荧光探针具有高灵敏度、高时空分辨率、操作简单、选择性好等优点，引起人们广泛关注。近年来，各种荧光传感器被用来粘度成像，大量的二氧化硫的荧光探针也被开发出来。然而，还没有探针能够同时检测粘度和SO2。因此，我们报告了一种新型双检测荧光探针，用于粘度和二氧化硫多重成像。
发明内容
本发明目的之一是提供一种检测粘度和SO2的荧光探针的合成方法；目的之二是提供一种检测粘度和SO2的荧光探针。
为实现上述目的，本发明采用如下技术方案。
一种检测粘度和SO2的荧光探针，其分子结构如下：
。
具体合成路线如下：
。具体合成方法如下：（1）3-甲基水杨酸与二氯亚砜 加热回流，反应结束，旋干得到油状物。（2）向化合物2加入N-甲基吡咯烷酮，冰浴条件下滴 加邻氨基苯硫酚和N-甲基吡咯烷酮混合溶液，滴加完毕后加热到90°C反应，反应结束，冷却 至室温，将反应液倒入冰水中，析出固体，过滤得化合物4。（3）化合物4、六次甲基四胺溶解 于三氟乙酸中，加热到130°C反应，反应结束，冷却至室温，将反应液倒入冰水中，析出固体， 过滤得粗产品，最后经柱层析分离得到化合物5。（4）2，3，3-三甲基吲哚与碘乙烷在乙腈中 在85°C下反应，反应结束，冷却至室温，过滤，石油醚洗涤得化合物6。（5）化合物5与化合物6 加少量哌嗪催化，在乙醇中80°C条件下反应，反应结束，冷却至室温，旋干除去溶剂，经柱层 析分离得到探针Mito-VBe。
本发明荧光探针在检测粘度和SO2的应用。
所述荧光探针在检测粘度的应用中，激发波长为405 nm，检测波段为450-750 nm；检测SO2的应用中，激发波长为405 nm，检测波段为430-750 nm。
本发明具有以下优点：
本发明涉及的一种检测粘度和SO2的荧光探针合成简单，通过不同通道可同时检测粘度和SO2，在生物化学领域具有重要的应用价值。
附图说明
图1为探针Mito-VBe分子结构图。
图2为探针Mito-VBe的1H NMR谱。
图3为探针Mito-VBe的13C NMR谱。
图4为探针Mito-VBe对不同粘度响应的荧光光谱。
图5为探针Mito-VBe对不同浓度SO2响应的荧光光谱。
图6为探针Mito-VBe选择性和抗干扰性图。
具体实施实例
实施例1 探针Mito-VBe的合成
。
（1）向干燥的50 mL单口圆底烧瓶中加入3-甲基水杨酸（1 g，6.58 mmol），然后加入适量二氯亚砜（量为刚好没过3-甲基-水杨酸），加热回流1 h，停止反应，旋干得到油状物。该反应物不需要纯化直接进行下一步反应。
（2）向上步骤得到的化合物2中加入2 mL N-甲基吡咯烷酮，冰浴条件下滴加邻氨基苯硫酚（0.86 g，6.88 mmol）和2 mL N-甲基吡咯烷酮混合溶液，滴加完毕后加热到90°C反应6 h，停止反应，冷却至室温，将反应液倒入100 mL冰水中，析出固体，过滤得化合物4。该反应物不需要纯化直接进行下一步反应。
（3）将上部所得的化合物4、六次甲基四胺（3.32 g，23.69 mmol）加入到50 mL圆底烧瓶中，再加入15 mL三氟乙酸，130°C反应3 h，停止反应，冷却至室温，将反应液倒入100mL冰水中，析出固体，过滤得粗产品，最后经柱层析分离得到产物5（2.14 g，产率：81.6%）。
（4）2，3，3-三甲基吲哚（0.2 g，1.26 mmol）、碘乙烷（0.24g，1.51 mmol），加入2 mL乙腈，加热到85°C下反应12 h，冷却至室温，过滤，石油醚洗涤得化合物6（0. 35 g，产率：87.5%）。
（5）化合物5（0.2 g，0.74 mmol）与化合物6（0.27 g， mmol）加少量哌嗪催化，在乙醇中80°C条件下反应6 h，冷却至室温，旋干除去溶剂，经柱层析分离得到探针Mito-VBe（0.24 g，产率57.1%）。探针1H NMR谱和13C NMR谱如图2和3：1H NMR (600 MHz, DMSO) δ8.65 (d, J = 1.8 Hz, 1H), 8.49 (d, J = 15.7 Hz, 1H), 8.32 (s, 1H), 8.20 (d, J= 7.9 Hz, 1H), 8.08 (d, J = 8.1 Hz, 1H), 7.83 (d, J = 7.3 Hz, 1H), 7.79 (d, J= 7.9 Hz, 1H), 7.57 (t, J = 7.5 Hz, 2H), 7.52 (t, J = 7.4 Hz, 1H), 7.48 (t, J= 7.5 Hz, 1H), 7.38 (d, J = 15.6 Hz, 1H), 5.75 (s, 1H), 4.63 (q, J = 6.8 Hz,2H), 2.34 (s, 3H), 1.81 (s, 6H), 1.44 (t, J = 7.2 Hz, 3H)；13C NMR (151 MHz,DMSO) δ 174.29, 167.16, 162.32, 153.65, 152.69, 151.40, 150.25, 143.70,143.11, 141.16, 138.78, 134.04, 133.48, 132.78, 130.28, 129.56, 129.46,129.40, 128.98, 128.51, 127.48, 127.27, 126.69, 125.92, 125.58, 124.13,123.43, 123.15, 122.75, 122.64, 122.29, 119.61, 118.56, 118.02, 114.36,113.36, 55.42, 51.84, 41.55, 40.42, 40.29, 40.15, 40.01, 39.87, 39.73, 39.59,26.56, 16.66, 13.91。
实施例2 荧光探针Mito-VBe对粘度和SO2的响应
在DMSO中配制浓度为1 mM探针Mito-VBe储备液。配制探针终浓度为5 μM，与不同粘度的溶液（水与甘油体积比分别0:10、1:9、2:8、3:7、4:6、5:5、6:4、7:3、8:2、9:1、10:0）混合，进行荧光检测（λex=405 nm），如图4所示。由图可知，随着溶剂粘度的增加，相对荧光强度变强。配制不同浓度的亚硫酸氢钠缓冲溶液DMSO/PBS（1/1，v/v，PBS 10 mM，pH=7.4）（依次为0，5，10，15，20，25，30，35，40，45，50，55，60，65，70，75，80，85 eq），其中探针Mito-VBe含量为5 µM，进行荧光检测（λex=405 nm），记录482 nm与600 nm处的荧光强度，如图5所示。分析I482nm/I600nm处的荧光强度与二氧化硫浓度的线性关系，如图所示：随着亚硫酸氢钠浓度的增加，482 nm处的吸收峰逐渐增加，600 nm处的吸收峰逐渐降低，当亚硫酸氢钠浓度达到80eq时，反应体系吸收峰值基本不再发生变化。
实施例3 荧光探针Mito-VBe的选择性
配制浓度为 150 mM的不同离子（F-、Cl-、Br-、I-、NO3 -、NO2 -、ACO-、SCN-、HCO-、CO3 2-、PO4 3-、CN-、HS-、HSO4 -、HSO3 -、ClO-、S2O3 2-）和生物硫醇（Cys、Hcy和GSH）溶液。
将亚硫酸氢钠和不同干扰物质的溶液与探针配制成缓冲溶液DMSO/PBS（1/1，v/v，PBS 10 mM，pH=7.4），干扰物质终浓度为200 μM，探针终浓度为5 μM，摇匀后进行荧光检测（λex= 405 nm），建立荧光强度比I482nm/I600nm与各干扰物质的柱状图，如图6所示。由图可知，荧光探针对各干扰离子和生物硫醇响应值低，对亚硫酸氢钠的I482nm/I600nm比值高，特异性好、抗干扰性能好。其他离子或生物硫醇对探针的荧光比值几乎没有影响，能够选择性的识别SO2。

Claims (1)

1.一种检测粘度和SO2的荧光探针，其结构为：
。
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