CN112457286B - 含有氧正离子的化合物在制备检测过氧化亚硝基离子的荧光分子探针中的应用 - Google Patents
含有氧正离子的化合物在制备检测过氧化亚硝基离子的荧光分子探针中的应用 Download PDFInfo
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Abstract
本发明公开了一种含有氧正离子的化合物在制备用于选择性检测过氧化亚硝基离子的比率荧光探针中的应用，其结构式如式I。本发明制备的荧光探针，具有良好的水溶性，高的荧光量子产率，大的斯托克斯位移，对ONOO‑具有极高的选择性，且响应时间短，检测限低，可以实现在水溶液或者细胞内对ONOO‑的高灵敏度、高选择性检测。本发明实现了活细胞水平中ONOO‑的检测，其作为新型探针可以应用于生物ONOO‑检测领域，有着广阔的应用前景。
Description
【技术领域】
本发明属于过氧化亚硝基离子检测的荧光探针领域，特别是一种含有氧正离子的化合物在制备用于选择性检测过氧化亚硝基离子的比率荧光探针中的应用。
【背景技术】
炎症和药物诱导肝损伤近年来被认为是一个严重的健康问题，因此高灵敏、高选择的精准检测炎症和药物诱导肝损伤过程中的生物标志物，将有助于人们更深入的了解这些疾病的发生与发展机制，对其进行及时预防和针对性治疗。过氧化亚硝基阴离子(ONOO-)是已知的药物诱导肝损伤的生物标志物，但是由于ONOO-极不稳定，半衰期很短，因此常用的检测方法难以用于检测过氧化亚硝基阴离子，需要发展快速定量实时的检测方法。而荧光方法由于其检出限低、高灵敏度、方便高效、实时监测等优势被广泛应用于分析检测领域，具有重要的实际应用前景。由于过氧化亚硝基离子具有强氧化性和亲核性，一方面导致许多ONOO-探针选择性欠佳，另一方面会导致在检测过程中探针出现假信号，最终导致检测结果不准确。为解决此类问题，本发明发展了一种利用含有氧正离子的化合物选择性识别过氧化亚硝基的新方法，具有非常重要的应用价值。
【发明内容】
本发明的目的是针对上述技术分析和存在问题，提供了一种含有氧正离子的化合物在制备检测过氧化亚硝基离子的荧光分子探针中的应用。
本发明的技术方案：
一种含有氧正离子的化合物在制备检测过氧化亚硝基离子的荧光分子探针中的用途，其特征在于：所述含有氧正离子的化合物的结构式如下(I)所示：
上述所述用于检测ONOO-的荧光探针的制备方法是：
将4-二乙胺基水杨醛和5-羟基-1-茚酮或6-羟基-1-萘酮在甲烷磺酸做溶剂的条件下缩合分别生成两个含氧正离子的探针化合物I-1和I-2。
述所述用于检测ONOO-的荧光探针可用于检测含ONOO-样品。
上述所述含ONOO-样品优选是生物细胞或含ONOO-的溶液。
本发明所述的荧光探针在水溶液中与ONOO-发生亲核加成及氧化反应，导致大的共轭体系被破坏，释放出蓝色荧光，从而达到检测的效果。
具体的：配制荧光探针分子的PBS溶液(10μM,pH＝7.4)的溶液，分别加入不同分析物(H2O2,HClO,1O2,TBHP,·OH,t-BuOO·，S2-,S2O3 2-,SCN-,Cys,Hcy，GSH，NO,NO2 -,水合肼，SO4 2-,CH3COO-,CO3 2-,Na+,K+,Ca2+,Mg2+,Zn2+,Fe2+,Cu2+)的水溶液。通过荧光分光光度计测试探针对于不同分析物的响应能力，结果如图1，2所示，只有加入ONOO-后，485纳米处的荧光强度才有明显的增强，说明两个探针化合物I-1和I-2对于ONOO-都具有良好的选择性。加入ONOO-后620nm左右处荧光发射波长明显下降，而485纳米左右处荧光发射波长增加，对应的溶液荧光颜色由红色变为蓝色，具有非常好的响应，见图3，4。通过共聚焦显微镜对孵育了荧光探针和ONOO-的活细胞进行荧光成像，观察蓝色荧光信号和红色荧光信号的变化，见图5和图6。通过细胞蓝色荧光的增强以及红色荧光的下降从而达到检测生物环境中的ONOO-的目的。
本发明的优点是：利用荧光方法检测ONOO-，选择性好，检测速度快，并且适合裸眼检测，不受其它ROS等分析物的干扰，实现了在水溶液及生物细胞内特异性检测ONOO-的效果。本发明实现了活细胞水平中ONOO-的检测，其作为新型探针可以应用于ROS检测领域，有着广阔的应用前景。
【附图说明】
图1为探针I-1溶液中分别加入不同的分析物后在485nm处的荧光强度。
图2为探针I-2溶液中分别加入不同的分析物后在485nm处的荧光强度。
图3为探针I-1溶液中加入不同浓度的ONOO-后，产生的荧光光谱变化，ONOO-浓度由0增加到10μM。
图4为探针I-2溶液中加入不同浓度的ONOO-后，产生的荧光光谱变化，ONOO-浓度由0增加到10μM。
图5是探针I-1在HepG-2细胞内荧光共聚焦成像图，其中对照组A：HepG2细胞在加入探针I-1(5μM)的细胞培养液中培养30分钟；对照组B：HepG2细胞在加入探针I-1(5μM)和过氧化亚硝基引发剂Sin-1(1mM)的细胞培养液中共孵育1h；对照组C:HepG2细胞加入过氧化亚硝基引发剂Sin-1(1mM)孵育1h，然后加入过氧化物消除剂UA(100μM)孵育3h，最后加入探针I-1(5μM)培养30分钟。
图6是探针I-2在HepG-2细胞内荧光共聚焦成像图，其中对照组D：HepG2细胞在加入探针I-2(5μM)的细胞培养液中培养30分钟；对照组E：HepG2细胞在加入探针I-2(5μM)和过氧化亚硝基引发剂Sin-1(1mM)的细胞培养液中共孵育1h；对照组F:HepG2细胞加入过氧化亚硝基引发剂Sin-1(1mM)孵育1h，然后加入过氧化物消除剂UA(100μM)孵育3h，最后加入探针I-2(5μM)培养30分钟。
【具体实施方式】
为了进一步说明本发明，给出以下系列具体实施例，但本发明并不受这些具体实施例的限制，了解该领域的技术人员对本发明的些许改动将可以达到类似的结果，这些改动也包含在本发明中。
【实施例1】
用微量注射器分别向配好的探针I-1的PBS(pH＝7.4)缓冲液的溶液中加入1当量的ONOO-和50当量的H2O2,HClO,1O2,TBHP,·OH,t-BuOO·,H2O2,HClO,1O2,TBHP,·OH,t-BuOO·,S2-,S2O3 2-,SCN-,Cys,Hcy,GSH,NO,NO2 -,水合肼,SO4 2-,CH3COO-,CO3 2-,Na+,K+,Ca2+,Mg2+,Zn2+,Fe2+,Cu2+的水溶液，放置10分钟后进行荧光分光光度法测试，显示探针I-1对于ONOO-具有良好的选择性，见图1。加入ONOO-后620nm左右处的荧光发射波长明显降低，而485nm左右处的荧光发射波长明显增强，具有非常好的响应，见图3。
【实施例2】
用微量注射器分别向配好的探针I-2的PBS(pH＝7.4)缓冲液的溶液中加入1当量的ONOO-和50当量的H2O2,HClO,1O2,TBHP,·OH,t-BuOO·,H2O2,HClO,1O2,TBHP,·OH,t-BuOO·,S2-,S2O3 2-,SCN-,Cys,Hcy,GSH,NO,NO2 -,水合肼,SO4 2-,CH3COO-,CO3 2-,Na+,K+,Ca2+,Mg2+,Zn2+,Fe2+,Cu2+的水溶液，放置10分钟后进行荧光分光光度法测试，显示探针I-2对于ONOO-具有良好的选择性，见图2。加入ONOO-后620nm左右处的荧光发射波长明显降低，而485nm左右处的荧光发射波长明显增强，具有非常好的响应，见图4。
【实施例3】
细胞内荧光成像测试：
HepG2细胞分为A、B、C三个对照组，分别用不同方法处理，
对照组A：HepG2细胞在加入探针I-1(5μM)的细胞培养液中培养30分钟；对照组B：HepG2细胞在加入探针I-1(5μM)和过氧化亚硝基引发剂Sin-1(1mM)的细胞培养液中共孵育1h；对照组C:HepG2细胞加入过氧化亚硝基引发剂Sin-1(1mM)孵育1h，然后加入过氧化物消除剂UA(100μM)孵育3h，最后加入探针I-1(5μM)培养30分钟。
荧光共聚焦显微镜显示探针I-1渗透进细胞内，对照组A细胞有红色荧光，无蓝色荧光；对照组B在加入Sin-1后红色荧光消失，出现明显的蓝色荧光；对照组C在加入Sin-1和UA后有红色荧光，无蓝色荧光，见图5。
【实施例4】
细胞内荧光成像测试：
HepG2细胞分为D、E、F三个对照组，分别用不同方法处理，
对照组D：HepG2细胞在加入探针I-2(5μM)的细胞培养液中培养30分钟；对照组E：HepG2细胞在加入探针I-2(5μM)和过氧化亚硝基引发剂Sin-1(1mM)的细胞培养液中共孵育1h；对照组F:HepG2细胞加入过氧化亚硝基引发剂Sin-1(1mM)孵育1h，然后加入过氧化物消除剂UA(100μM)孵育3h，最后加入探针I-2(5μM)培养30分钟。
荧光共聚焦显微镜显示探针I-2渗透进细胞内，对照组D细胞有红色荧光，无蓝色荧光；对照组E在加入Sin-1后红色荧光消失，出现明显的蓝色荧光；对照组F在加入Sin-1和UA后有红色荧光，无蓝色荧光，见图6。
结果表明，荧光探针I-1和探针I-2对于ONOO-有很好的响应能力，同时能够避免其他ROS等分析物的干扰，可以作为比色以及荧光探针选择性地识别ONOO-，有广泛的应用前景。
Claims (2)
1.一种含有氧正离子的化合物在制备检测过氧化亚硝基离子的荧光分子探针中的用途，其特征在于：所述含有氧正离子的化合物的结构式如下(I)所示：
2.如权利要求1所述的用途，其特征在于：可以检测生物细胞或含过氧化亚硝基离子的溶液中的过氧化亚硝基离子。
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