CN112079857A - 一种过氧亚硝酸根荧光探针及其制备方法和应用 - Google Patents
一种过氧亚硝酸根荧光探针及其制备方法和应用 Download PDFInfo
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Abstract
Description
技术领域
本发明涉及一种过氧亚硝酸根荧光探针及其制备方法和应用。
背景技术
ONOO-是NO·与O2·-.相互反应的产物,ONOO-能导致DNA损伤,酶抑制,细胞死亡和细菌中毒并且能够引起一系列疾病。通过对ONOO-的检测研究,可以帮助我们更好的解释疾病产生的原因,由此采取有效的预防措施,减少对机体的伤害。
目前测定ONOO-的方法主要有电子自旋共振法、电子顺磁共振法、高效液相色谱法、化学发光法、荧光法以及电化学方法等。然而,由于生物体内ONOO-的半衰期非常短,稳态浓度低,所以真正适用于生物体活体内ONOO-的方法依旧较少,这就迫切需要相关科研工作者开发能够对ONOO-专一识别、快速响应的荧光探针用以动态观测某些器官中ONOO-的产生、代谢、相互转化及动态损伤生物机体的过程。
荧光探针因选择性好,灵敏度高,操作简单,成本较低并且可以实现实时监测等优点,现广泛应用于离子的测定。尽管已有多种检测ONOO-荧光探针被报道,但是目前荧光探针的灵敏度和专一性不够好,因此,开发性能更好的荧光探针来检测ONOO-具有重要的意义。
发明内容
本发明的目的之一在于克服现有技术中存在的问题,提供一种过氧亚硝酸根荧光探针,能用于快速高灵敏选择性的识别ONOO-,从而能够有效检测体内或体外ONOO-。
本发明的目的之二在于提供该探针的制备方法。
本发明的目的之三在于提供该探针在识别和检测ONOO-中的应用。
为达到上述目的,本发明采用如下反应路线:
根据上述反应路线,本发明采用如下技术方案:
一种过氧亚硝酸根荧光探针,其特征在于该荧光探针的结构式为:
一种制备上述的过氧亚硝酸根荧光探针的方法,其特征在于该方法的具体步骤为:
a.将吡啶-4-甲醛和2,4-二甲基吡咯溶于二氯甲烷中,滴入催化量的三氟乙酸作为催化,在惰性气氛保护下,搅拌反应过夜,除去溶剂后加入四氯苯醌,继续反应25~35min;加入三乙胺,搅拌15min~30mon;在冰水浴下,加入三氟化硼乙醚,在冰水浴下反应2h~3h,室温下反应3h~5h,经分离提纯,得到化合物b,其结构式为:所述的吡啶-4-甲醛和2,4-二甲基吡咯、四氯苯醌、三乙胺的摩尔比为:4.5:9.7:4.5:40;
b.将步骤a所得化合物b和碘乙烷按0.9:18的摩尔比溶于乙腈中,回流12h~15h,混合液冷却至室温,除去溶剂,然后经分离提纯,得到过氧亚硝酸根荧光探针。
上述的过氧亚硝酸根荧光探针在识别和检测ONOO-中的应用。
本发明的过氧亚硝酸根荧光探针本身荧光很弱,当ONOO-作用后形成的化合物A在525nm处有很大的荧光强度。而本发明的荧光探针分别与OCl-、ROO·、·OH、·NO、H2O2、·O2 -、t-BuOO·进行作用时均不会产生荧光强度很强的化合物,从而实现对ONOO-的特异性识别。
本发明的过氧亚硝酸根荧光探针的响应过程如下,ONOO-氧化过氧亚硝酸根荧光探针得到中间体1,中间体1失去﹣NO2后形成中间体2,最后中间体2经过质子化后得到化合物A。
具体而言,其作用机理如下:
本发明的探针是过氧亚硝酸根荧光探针,这类探针可以高灵敏高选择性的识别ONOO-并进行准确检测。且本发明的探针本身荧光很弱,当与ONOO-结合后得到强荧光的化合物A,性质稳定,有利于实际样本中对ONOO-(体内/体外)进行检测。
附图说明
图1为本发明过氧亚硝酸根荧光探针的选择性,荧光探针在PBS缓冲溶液(10%)与ONOO-(10当量)的荧光光谱图;
图2为本发明的过氧亚硝酸根荧光探针在PBS(10%)中与不同当量ONOO-作用后的荧光光谱变化;
图3为本发明的过氧亚硝酸根荧光探针与ONOO-作用生成化合物A的吸光度;
图4为本发明的过氧亚硝酸根荧光探针以及检测ONOO-后形成化合物A的质谱图。
图5为本发明的过氧亚硝酸根荧光探针与外源性ONOO-的细胞(Hela细胞)成像图(λex/em=473nm/490-540nm);
图6为本发明的过氧亚硝酸根荧光探针与内源性ONOO-的细胞(RAW264.7细胞)成像图(λex/em=473nm/490-540nm)。
具体实施方式
以下结合附图对本发明的优选案例进行说明,应当理解此处所描述的优选案例仅限于说明和解释本发明,并不用于限定本发明。为了使公众对本发明有充分的了解,在本发明优选实施例中详细说明了具体细节。
实施例1:
过氧亚硝酸根荧光探针的制备过程。
步骤(1):在250mL单口圆底烧瓶中,加入150mL的二氯甲烷,依次加入吡啶-4-甲醛(4.5mmol,0.48g)和2,4-二甲基吡咯(9.7mmol,0.92g),滴入一滴三氟乙酸作为催化,N2保护,快速搅拌过夜,旋蒸除去溶剂后加入四氯苯醌(4.5mmol,1.1g)继续处理30min。
步骤(2):在步骤(1)的产物中加入7.5mL三乙胺,搅拌15min。0℃下加入7.5mL三氟化硼乙醚,室温下搅拌3h。0℃下反应2h,室温下反应3h,用饱和氨酸氢钠溶液洗涤,分离有机相,用无水硫酸镁干燥,得到化合物b,其结构式为:步骤(3):将化合物b(0.09mmol,0.03g)加入100mL单口圆底烧瓶中,溶于干乙腈,加入碘乙烷(0.9mmol,60μL),回流12h。混合液冷却至室温,旋蒸除去溶剂,然后进行柱色谱分离,得到过氧亚硝酸根荧光探针。其表征参数如下:
1H NMR(500MHz,DMSO):δ=8.78(d,2H),7.94(d,2H),6.02(s,1H),5.65(s,1H),4.40(m,2H),2.72(s,3H),2.29(s,3H),1.5(t,3H)1.95(s,3H),1.47(s,3H);ESI-MS:[M+H]+calcd for 354.1,Found 354.3。
实施例2:将实施例1所得过氧亚硝酸根荧光探针(10当量)溶于PBS缓冲溶液(10%)中,不做处理,发现该探针自身的荧光很弱甚至没有荧光,向溶液中加入OCl-、ROO·、·OH、·NO、H2O2、·O2 -、t-BuOO·后均没有引起荧光的变化,但是加入ONOO-后引起了荧光变化,说明该探针对ONOO-表现出高选择性的识别,参见图1。
实施例2:
本发明的过氧亚硝酸根荧光探针随不同当量的ONOO-加入荧光谱图的变化,在本发明中,当ONOO-的当量为10时,形成的化合物A的荧光强度最大,参见图2。
实施例3:
本发明中的过氧亚硝酸根荧光探针自身的荧光强度很小甚至没有荧光,参见图3。当与ONOO-作用时形成化合物A具有很强的荧光,为了证明化合物A的形成,对其进行了质谱表征,参见图4,得出本发明的机理是荧光探针与ONOO-作用形成了新的化合物A的结论。
实施例4:
外源性ONOO-的细胞成像:在孵育好的Hela细胞培养基内加入5μM的过氧亚硝酸根荧光探针染色,30分钟后并用DPBS洗涤并加入ONOO-,参见图5,从左至右,不加入ONOO-、加入2mM的ONOO-、加入4mM的ONOO-)在激光共聚焦扫描显微镜下观察细胞形态。实验时用473nm的激光器,收集波段为490-540nm。结果显示,未加入ONOO-的Hela细胞无荧光产生,加入了ONOO-的Hela细胞有荧光产生,而且荧光强度随ONOO-的增大有所增强。
实施例5:
内源性ONOO-的细胞成像:RAW264.7细胞的荧光特性。将细胞用5μM的过氧亚硝酸根荧光探针染色,30分钟后并用DPBS洗涤,通过共聚焦显微镜成像。实验时用473nm的激光器,收集波段为490-540nm。(a)不做任何处理的细胞(b)加入LPS、IFN-γ、PMA(c)加入LPS、IFN-γ、PMA+aminoguanidine(d)LPS、IFN-γ、PMA+TEMPO。结果显示,只有按照b处理的细胞才有荧光产生,参见图6。
以上内容是结合具体的优选实施方式对本发明所作的进一步详细说明,不能认定本发明的具体实施方式仅限于此,对于本发明所属技术领域的普通技术人员来说,在不脱离本发明构思的前提下,还可以做出若干简单的推演或替换,都应当视为属于本发明由所提交的权利要求书确定专利保护范围。
Claims (3)
2.一种制备权利要求1所述过氧亚硝酸根荧光探针的方法,其特征在于,该方法的具体步骤为:
a.将吡啶-4-甲醛和2,4-二甲基吡咯溶于二氯甲烷中,滴入催化量的三氟乙酸作为催化,在惰性气氛保护下,搅拌反应过夜,除去溶剂后加入四氯苯醌,继续反应25~35min;加入三乙胺,搅拌15min~30mon;在冰水浴下,加入三氟化硼乙醚,在冰水浴下反应2h~3h,室温下反应3h~5h,经分离提纯,得到化合物b,其结构式为:所述的吡啶-4-甲醛和2,4-二甲基吡咯、四氯苯醌、三乙胺的摩尔比为:4.5:9.7:4.5:40;
b.将步骤a所得化合物b和碘乙烷按0.9:18的摩尔比溶于乙腈中,回流12h~15h,混合液冷却至室温,除去溶剂,然后经分离提纯,得到过氧亚硝酸根荧光探针。
3.一种权利要求1所述过氧亚硝酸根荧光探针在识别和检测ONOO-中的应用。
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CN115232098A (zh) * | 2022-07-18 | 2022-10-25 | 嘉兴学院 | 一种用于快速灵敏检测过氧硝酸盐的Rhodol荧光探针及其制备方法和应用 |
CN115232098B (zh) * | 2022-07-18 | 2023-10-03 | 嘉兴学院 | 一种用于快速灵敏检测过氧硝酸盐的Rhodol荧光探针及其制备方法和应用 |
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