CN115572276B - 一种内质网靶向的极性比率型荧光探针及其制备方法和用途 - Google Patents

一种内质网靶向的极性比率型荧光探针及其制备方法和用途 Download PDF

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CN115572276B
CN115572276B CN202211106072.5A CN202211106072A CN115572276B CN 115572276 B CN115572276 B CN 115572276B CN 202211106072 A CN202211106072 A CN 202211106072A CN 115572276 B CN115572276 B CN 115572276B
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孟祥明
卫丽云
李晓宇
陈诺
胡玲桢
赵辰妍
冯燕
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Anhui University
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Abstract

本发明公开了一种内质网靶向的极性比率型荧光探针及其制备方法和用途，其中内质网靶向的比率极性荧光探针的结构如下：本发明内质网靶向的比率极性响应荧光探针，在体外实验中表现出对极性的良好响应。细胞毒性测试表明该荧光探针具较低的生物毒性，双光子共聚焦荧光显微成像实验表明该荧光探针对HeLa细胞光稳定性好，可以有效定位细胞中的内质网(定位系数为0.89)，适用于细胞内的双光子荧光成像和检测。

Description

一种内质网靶向的极性比率型荧光探针及其制备方法和用途
技术领域
本发明涉及一种内质网靶向的极性比率型荧光探针及其制备方法和用途，以实现比率响应成像检测细胞内质网内的极性变化，具有高选择性、高灵敏度、低生物毒性的优点。
背景技术
内质网(ER)是蛋白质和脂质合成的必要组成部分。当其正常功能受到葡萄糖毒性、钙失衡、蛋白质合成异常等因素干扰时，内质网会相应地产生自我保护机制，发生应激反应。过度的内质网应激(内质网应激)可导致细胞死亡，如凋亡、铁死亡和细胞凋亡。内质网极性的反常变化与一些疾病的产生关系密切。因此，活细胞和组织中内质网极性的检测和实时监测对于研究内质网相关的生理和病理过程至关重要。
铁死亡是一种新的调节细胞死亡的方式，是铁依赖性脂质过氧化物积累的结果，与传统的凋亡和坏死不同。研究表明，抑制上游调节器系统XC-GSH通过药物或小分子化合物(氨基酸逆向转运蛋白)或下游效应子GPX4(谷胱甘肽过氧化物酶4)被认为是典型的铁死亡的内外途径。目前，已有大量证据证明，铁下垂与急性肾损伤、例肝损伤、例创伤性脑损伤、7例等疾病有关。一些研究表明，铁死亡抑制剂肿瘤的发展，如急性淋巴细胞白血病、宫颈癌、和胶质瘤。因此，监测铁死亡的进一步研究可以为癌症治疗和药物开发提供新思路。
与其他生物分析方法相比，荧光探针结合荧光显微成像技术由于其无创、高灵敏度、优异的特异性和响应时间短等优势已成为一种在亚细胞水平上对分析物进行可视化监测的有效方法。近年来，荧光成像的方法已经被广泛应用于检测活细胞内质网内的极性变化，报道了许多可在内质网内检测极性的荧光探针，但基于激发态内分子质子转移效应比率极性相应的荧光探针还是非常少的，因此开发一种内质网靶向的极性比率型荧光探针是非常迫切和重要的。
发明内容
本发明旨在提供一种内质网靶向的极性比率型荧光探针及其制备方法和用途，所要解决的技术问题是通过分子设计得到一种可以特异性靶向内质网，且具有可以比率极性响应的有机小分子结构，以实现通过荧光成像实时监测活细胞内质网内的极性变化，具有选择性高、灵敏度高、光稳定性好等优点，细胞毒性测试表明本发明荧光探针的细胞相容性良好。
本发明内质网靶向的极性比率型荧光探针，简记为HCT-ER，以黄酮醇为母体，其结构式如下所示：
本发明内质网靶向的极性比率型荧光探针的制备方法，包括如下步骤：
步骤1：将2-羟基苯乙酮(1.53g)和4-丁氧基苯甲醛(2.12g)溶解在乙醇(5mL)中，随后逐滴加入4mLNaOH(3.51g)溶液，在常温下搅拌反应24h，得到化合物1。
步骤2：向化合物1中逐滴加入1mLNaOH(0.89g)溶液和H2O2溶液(5mL，9.79mol/L)，加热至50℃，搅拌反应8小时；反应结束后冷却至室温，加入1M氢氧化钠溶液调节pH至中性，然后将混合物在水中用CH2Cl2(30mL)萃取3次，有机层用无水Na2SO4干燥并浓缩，得到粗产物；粗品经柱层析(石油醚:乙酸乙酯＝50:1，作为洗脱液)纯化得目标产物HCT-ER，2.68g，产率78％。
本发明内质网靶向的极性比率型荧光探针的合成过程如下：
本发明内质网靶向的极性比率型荧光探针的用途，是用于制备检测活细胞内质网内极性变化的检测试剂。
进一步的，所述检测试剂能够对Erastin和RSL3诱导细胞铁死亡过程中内质网内极性的变化产生响应。
检测方法如下：
将本发明HCT-ER溶于DMSO(5mL)中制得2mM的母液，取15μL HCT-ER母液加入到3mL不同配比的1,4-Dioxane/H2O体系混合溶剂(极性参数设置为Δf)中，得到最终浓度为10μM的测试液。HCT-ER的单光子激发波长为370nm，检测375-600nm范围内的荧光光谱变化，可以明显观察到从水含量10％(Δf≈0.25)到70％(Δf≈0.31)，在430nm处荧光强度降低了11.6％，在530nm处荧光强度增强了17.3％，溶液极性和荧光强度呈现良好的线性关系(R2＝0.9821)。
本发明还探究了HCT-ER在HaLa细胞中的光学稳定性，因为在细胞铁死亡的过程中，细胞内环境发生明显变化，这会影响探针的光稳定性。此外，利用HCT-ER测试了Erastin和RSL3诱导细胞铁死亡过程中内质网内极性的变化趋势。同时，还使用了铁死亡抑制剂Fer-1测试抑制细胞铁死亡时内质网内极性的变化趋势。
本发明内质网靶向的比率极性响应荧光探针，在溶液和细胞中都对极性具有良好响应能力。细胞毒性测试表明HCT-ER的细胞相容性良好，双光子共聚焦荧光显微成像实验表明HCT-ER可以有效定位内质网(定位系数为0.89)，适用于内质网荧光成像和原位检测，可以原位检测Erastin和RSL3诱导细胞铁死亡过程中内质网内极性的变化趋势。
附图说明
图1是HCT-ER在不同溶剂体系中的(a)紫外吸收光谱图；(b)荧光发射光谱图及荧光强度(I430nm/I530nm)。
图2是HCT-ER在不同体积比的1,4-二氧六环/水混合体系中的(a)紫外吸收光谱图；(b)荧光发射光谱图及(c)荧光强度(I430nm/I530nm)和Δf之间的线性关系图。
图3是在不同浓度(0μM、10μM、20μM和30μM)的HCT-ER作用下的HeLa细胞存活率图。
图4是HCT-ER(10μM)和0.5μM商用内质网探针(ER Tracker)同时共染HeLa细胞的内质网共聚焦荧光成像图，探究HCT-ER的内质网靶向能力。
图5是HCT-ER(10μM)的共聚焦荧光成像图，探究HCT-ER的光学稳定性。
图6是HCT-ER(10μM)在10μM Erastin共同孵育的HeLa细胞铁死亡共聚焦荧光成像图。
图7是HCT-ER(10μM)在10μM Erastin及Fer-1(铁死亡抑制剂)共同孵育的HeLa细胞铁死亡共聚焦荧光成像图。
图8是HCT-ER(10μM)在10μM RSL3共同孵育的HeLa细胞铁死亡共聚焦荧光成像图。
图9是HCT-ER(10μM)在10μM RSL3及Fer-1(铁死亡抑制剂)共同孵育的HeLa细胞铁死亡共聚焦荧光成像图。
具体实施方式
下面通过实施例对本发明做进一步说明。
实施例1：HCT-ER的合成
在化合物1中逐滴加入溶解在H2O(1mL)中的NaOH(0.89g)和H2O2(5mL)，加热至50℃，搅拌反应8小时，反应结束后冷却至室温，加入氢氧化钠水溶液调节pH至中性。然后将混合物倒入水中，用CH2Cl2(30mL)萃取3次，有机层用无水Na2SO4干燥并浓缩，得到粗产物。粗品经柱层析(石油醚:乙酸乙酯＝50:1，作为洗脱液)纯化得目标产物HCT-ER，2.68g，产率78％。1H NMR(400MHz,DMSO-d6)δ9.40(s,1H),8.22–8.03(m,3H),7.82–7.66(m,2H),7.47–7.35(m,1H),7.07(d,J＝8.8Hz,2H),4.02(t,J＝6.5Hz,2H),1.74–1.63(m,2H),1.51–1.36(m,2H),0.91(t,J＝7.4Hz,3H)。13C NMR(101MHz,DMSO-d6)δ:173.17,160.46,154.98,146.16,138.68,134.02,129.94,125.27,125.01,123.95,121.90,118.85,115.02,67.91,31.20,19.25,14.23。ESI-MS m/z:calcd.for C19H18O4,HCT-ER,310.1214,found,310.1000。
实施例2：HCT-ER的光谱测试
将本发明HCT-ER溶于DMSO(5mL)中制得2mM的母液，取15μL HCT-ER母液加入到3mL不同配比的1,4-Dioxane/H2O体系混合溶剂(极性参数设置为Δf)中，获得探针HCT-ER在不同极性溶剂中的紫外光谱图(图2a)。其在430nm处荧光强度随着水含量从10％(Δf≈0.25)到70％(Δf≈0.31)降低了11.6％，在530nm处荧光强度增强了17.3％，溶液极性和荧光强度呈现良好的线性关系(R2＝0.9821)(图2b,c)。
实施例3：细胞毒性测试
在探针HCT-ER进行细胞成像的应用之前，需要对探针的毒性进行测试，采用MTT法进行实验。分别加入0μM、10μM、20μM和30μM的探针HCT-ER培养HeLa细胞24h，发现细胞存活率始终保持在90％以上(图3)。因而探针HCT-ER对于HeLa细胞的毒性较低，可以进行生物应用。
实施例4：细胞定位测试
为了研究HCT-ER的内质网定位性能，这里使用内质网的商业染料(ER Tracker，0.5μM)与HCT-ER在HeLa细胞中进行共定位研究。结果表明HCT-ER的蓝色通道(λex＝365nm，λem＝435nm)以及绿色通道(λex＝365nm，λem＝535nm)和ER Tracker(λex＝580nm,λem＝615nm)的荧光图像重叠良好，并且HCT-ER与ER Tracker的Pearson共定位系数计算为0.89(图4)。这些结果表明，HCT-ER可以很好地定位于活细胞的内质网中。
实施例5：HCT-ER的时间稳定性
对探针HCT-ER在细胞中的长时间成像进行测试，如图5，随着光照射时间的延长，无论是探针HCT-ER的蓝色通道还是绿色通道的荧光均保持稳定。说明探针HCT-ER很稳定，是适合用于在细胞中的长时间成像的。
实施例6：HCT-ER对Erastin诱导的铁死亡成像
使用探针HCT-ER和Erastin共同培养细胞30分钟，之后进行共聚焦荧光成像。获得了如图6所示的一系列图片，可以观察到随着药物处理时间的延长，探针HCT-ER的蓝色通道的荧光强度逐渐降低，绿色通道荧光强度逐渐增强，说明了铁死亡过程中内质网极性的变大。证明探针HCT-ER可以通过极性比率响应被用于铁死亡。
实施例7：HCT-ER对Fer-1抑制铁死亡的成像
为了进一步说明实施例6中，极性的变化是由Erastin诱导的铁死亡引起的，在探针HCT-ER培养细胞30分钟后，采用了加入Fer-1作为铁死亡抑制剂，与Erastin共同培养细胞的实验方案。结果如图7所示，无论是探针HCT-ER的蓝色通道还是绿色通道，荧光强度都维持着稳定的水平，说明在铁死亡被抑制时，内质网的极性没有发生明显的波动。上述实验结果证明，探针HCT-ER可以作为一种有效的工具，通过比率极性响应从不同角度来评估和监测内质网铁死亡，并且这种不依赖于单一参数的监控方式可以避免来自复杂生理环境的实验误差，获得更准确的结果。因此探针HCT-ER具有应用于评价和筛选内质网铁死亡诱导/抑制剂的前景。
实施例8：HCT-ER对RSL3诱导的铁死亡成像
使用探针HCT-ER和RSL3共同培养细胞30分钟，之后进行共聚焦荧光成像。获得了如图8所示的一系列图片，可以观察到随着药物处理时间的延长，探针HCT-ER的蓝色通道的荧光强度逐渐降低，绿色通道荧光强度逐渐增强，说明了铁死亡过程中内质网极性的变大。证明探针HCT-ER可以通过极性比率响应被用于铁死亡。
实施例9：HCT-ER对Fer-1抑制铁死亡的成像
为了进一步说明实施例8中极性的变化是由RSL3诱导的铁死亡引起的，在探针HCT-ER培养细胞30分钟后，采用了加入Fer-1作为铁死亡抑制剂，与RSL3共同培养细胞的实验方案。结果如图9所示，无论是探针HCT-ER的蓝色通道还是绿色通道，荧光强度都维持着稳定的水平，说明在铁死亡被抑制时，内质网的极性没有发生明显的波动。上述实验结果证明，探针HCT-ER可以作为一种有效的工具，通过比率极性响应从不同角度来评估和监测内质网铁死亡，并且这种不依赖于单一参数的监控方式可以避免来自复杂生理环境的实验误差，获得更准确的结果。因此探针HCT-ER具有应用于评价和筛选内质网铁死亡诱导/抑制剂的前景。

Claims (2)

1.一种内质网靶向的极性比率型荧光探针在制备用于检测活细胞内质网内极性变化的检测试剂中的用途，其特征在于：
所述内质网靶向的极性比率型荧光探针的结构式如下所示：
2.根据权利要求1所述的用途，其特征在于：
所述检测试剂对Erastin和RSL3诱导细胞铁死亡过程中内质网内极性的变化产生响应。
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JP2013139538A (ja) * 2012-01-06 2013-07-18 Toyo Ink Sc Holdings Co Ltd 波長変換性樹脂組成物および太陽電池封止材
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