CN114634464A - 一种用于检测次氯酸的溶酶体靶向近红外荧光探针及其制备方法和应用 - Google Patents
一种用于检测次氯酸的溶酶体靶向近红外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
本发明属于荧光探针技术领域,具体涉及一种用于检测次氯酸的溶酶体靶向近红外荧光探针及其制备方法和应用。
背景技术
活性氧(ROS)是一类具有化学活性的氧分子,包括羟基自由基(·OH)、超氧阴离子(O2-)、次氯酸(HClO)、过氧化氢(H2O2)等(Wang P,Gong Q,Hu J,Li X,Zhang X.ReactiveOxygen Species(ROS)-Responsive Prodrugs,Probes,and Theranostic Prodrugs:Applications in the ROS-Related Diseasess.J Med Chem.2021;64(1):298-325)。其中,次氯酸作为一种抗菌试剂在临床中常用于杀灭细菌及微生物。在生物体内,次氯酸是一种重要的活性氧物种,主要由过氧化氢和氯离子在髓过氧化酶(MPO)催化反应下产生(Klebanoff S J,Kettle A J,Rosen H,Winterbourn C C,Nauseef WM.Myeloperoxidase:a front-line defender against phagocytosed microorganisms.JLeukoc Biol.2013;93(2):185-198)。体内次氯酸的异常表达会产生严重的副作用,甚至引起心血管疾病、癌症等疾病(Gorrini C,Harris I S,Mak T W.Modulation of oxidativestress as an anticancer strategy.Nat Rev Drug Discov.2013;12(12):931-947;YangJ,Zhang X,Yuan P,et al.Oxalate-curcumin-based probe for micro-andmacroimaging of reactive oxygen species in Alzheimer's disease.Proc Natl AcadSci USA.2017;114(47):12384-12389)。因此,设计一种有效检测次氯酸的方法,是具有重要意义的。
测定次氯酸含量的常见方法有高效液相色谱法、气相色谱法、电化学法等,但是大都灵敏度低,有的需要侵入性破坏生物组织。与之相比,荧光成像具有高灵敏度、高选择性、高时空分辨能力、操作简便等明显优势,广泛应用于细胞内活性分子的成像检测。由于次氯酸的亚细胞分布尚不清楚,仍难以阐明次氯酸在细胞内的功能。因此,有必要开发荧光探针来检测次氯酸在亚细胞水平的分布。尽管目前已报道了多种次氯酸荧光探针,已应用于亚细胞器(线粒体或溶酶体)中次氯酸的荧光成像分析(Shen S L,Huang X Q,Jiang H L,LinX H,Cao X Q.A rhodamine B-based probe for the detection of HOCl inlysosomes.Anal Chim Acta.2019;1046:185-191)。但他们仍然存在一个共同的问题,这些细胞器靶向的荧光探针发射波长大多在可见光区域,这将会影响探针在生物系统中的应用。因此,设计一种检测溶酶体次氯酸的近红外荧光探针是很有必要的。
本发明设计并合成了检测溶酶体中的次氯酸的近红外荧光探针,此探针与次氯酸反应后,作用迅速,产生强烈的红色荧光,表现出很高的灵敏度,该荧光探针与次氯酸作用迅速,并具有高选择性。并且可成功用于离体细胞中次氯酸的荧光成像。
发明内容
本发明的目的在于提供一种用于检测次氯酸的溶酶体靶向近红外荧光探针,下简称MB-HClO,该荧光探针具有长波长(在近红外区)、高灵敏度以及高选择性的检测次氯酸,并能够应用于活细胞中次氯酸的荧光成像。
为实现上述技术目的,本发明所采用的技术方案为:
一种用于检测次氯酸的溶酶体靶向近红外荧光探针的制备方法,包括以下步骤:
(1)在250ml圆底烧瓶中,加入亚甲基蓝5g,用50ml二氯甲烷溶解得反应液,将6.63g碳酸钠溶解在50ml水中,逐滴加入到上述反应液中,然后用同样的方法将10.89g连二亚硫酸钠溶解在50ml超纯水中逐滴加入到上述反应液中,加热至40℃,磁力搅拌30分钟,随后反应液冰浴,将2.78g三光气溶于25ml二氯甲烷中逐滴加入到上述反应液中,继续搅拌1小时,全程用氮气保护,柱层析分离提纯,得到化合物MB-COCl;合成的MB-COCl不稳定,直接用于下一步反应;
(2)将0.5g化合物MB-COCl和0.26gN-(3-氨丙基)吗啉溶解于25ml二氯甲烷中,加入到100mL圆底烧瓶中,随后加入0.44g三乙胺,室温下,搅拌2小时,柱层析分离提纯,得浅蓝色固体,即目标产物探针。
反应路线如下:
一种用于检测次氯酸的溶酶体靶向近红外荧光探针的应用,用于检测水溶液中次氯酸的含量或者离体活细胞溶酶体中次氯酸的含量。
本发明探针用于溶液中次氯酸的检测,所述荧光探针本身无荧光,与次氯酸反应生成MB,产生强烈的红色荧光,发射波长在690nm,线性范围为0.01-50μM,检测限为50nM,该探针表现出很高的灵敏度;该荧光探针与次氯酸作用迅速,响应时间在2秒内;该荧光探针对次氯酸表现出很好的选择性,不受Zn2+、Fe3+、Fe2+、Ca2+、Mg2+、K+、Na+、Mn2+、Cl-、CO3 2-、NO2-、HCO3-、I-、CH3COO-、HPO4 2-、SO4 2-、KO2、H2O2、Hcy、Cys、GSH、H2S的影响。
所述的一种用于检测次氯酸的溶酶体靶向近红外荧光探针的应用:向细胞内加入一定量的次氯酸,再加探针孵育,观察到强的红色荧光;向细胞内加入一定量的脂多糖和佛波酯刺激细胞,再加探针孵育,能检测到强的红色荧光信号;加入一定量的抗氧化剂N-乙酰-L-半胱氨酸处理细胞,再加入一定量的脂多糖和佛波酯刺激细胞,再加探针孵育,细胞内荧光信号消失。将该荧光探针应用于细胞溶酶体成像中,向细胞内加入一定量的次氯酸,随后加入探针和碧云天商用溶酶体定位剂(绿色)共同培养,能检测到探针的荧光信号和溶酶体定位剂(绿色)的荧光信号重叠。这些现象表明该近红外荧光探针不仅能检测水溶液中的次氯酸,还可应用于检测细胞溶酶体中次氯酸的含量,这对于深入研究次氯酸在生物体内生理和病理过程具有重要意义。
有益效果
本发明的溶酶体靶向近红外荧光探针在次氯酸存在下荧光发生显著变化,可以用于高灵敏度的检测次氯酸,该荧光探针的线性范围为0.01-50μM,检测限为50nM。同时,该荧光探针对次氯酸响应迅速,响应时间在2秒内。并且该近红外荧光探针对次氯酸表现出很好的选择性,不受Zn2+、Fe3+、Fe2+、Ca2+、Mg2+、K+、Na+、Mn2+、Cl-、CO3 2-、NO2-、HCO3 -、I-、CH3COO-、HPO4 2-、SO4 2-、KO2、H2O2、Hcy、Cys、GSH、H2S的影响。
附图说明
图1为本发明探针的氢谱图;
图2为本发明探针的碳谱图;
图3为本发明探针的高分辨质谱图;
图4为本发明探针与不同浓度的次氯酸作用后的荧光光谱图;
其中,横坐标为波长,纵坐标为荧光强度。荧光探针的浓度为10μM,次氯酸浓度依次为:0、5、10、15、20、25、30、40、45、50μM。荧光激发波长为640nm。插图为探针对次氯酸浓度的线性响应图;
图5为本发明探针与次氯酸的作用机理图;
图6为本发明探针与不同浓度次氯酸作用后的紫外可见吸收光谱图;
其中,横坐标为波长,纵坐标为紫外吸收强度。荧光探针的浓度为10μM,次氯酸浓度依次为:0、5、10、15、20、25、30、40、45、50μM;
图7为本发明探针加入次氯酸前后的时间响应荧光光谱;
图8为本发明探针对不同干扰分析物的选择性柱状荧光图;F0和F表示探针溶液加入次氯酸前后的荧光强度;
图9为本发明探针的细胞毒性试验;横坐标为荧光探针的浓度,纵坐标为细胞的存活率;
图10为本发明探针在RAW264.7细胞中与外源性次氯酸的荧光成像图;
图11为本发明探针在RAW264.7细胞中与内源性次氯酸的荧光成像图;
图12为本发明探针在RAW264.7细胞中与溶酶体次氯酸的荧光成像图;
其中,(a-c)为探针和溶酶体绿色定位剂共染色RAW 264.7细胞荧光成像图;(a)激发波长为405nm,发射波长扫描范围为550-950nm;(b)激发波长为405nm,发射波长扫描范围为550-950nm;(c)明场图(d)图(a)、(b)和(c)叠加图;(e)荧光分布散点图;(f)线性区域红色和绿色荧光强度位置与强度关系图。
具体实施方式
下面结合具体实施例对本发明的技术方案做进一步说明,但不限于此。
实施例1
MB-COCl的合成:
在250ml圆底烧瓶中,加入亚甲基蓝(5g,15.63mmol),用50ml二氯甲烷溶解得反应液,将碳酸钠(6.63,62.5mmol)溶解在50ml水中,逐滴加入到上述反应液中,然后用同样的方法将连二亚硫酸钠(10.89g,62.5mmol)溶解在50ml超纯水中逐滴加入到上述反应液中,加热至40℃,磁力搅拌30分钟,随后将反应液冰浴,将(2.78g,9.38mmol)三光气溶于25ml二氯甲烷中逐滴加入到上述反应液中,继续搅拌1小时,全程用氮气保护,柱层析分离提纯,得到化合物MB-COCl,合成的MB-COCl不稳定,直接用于下一步反应。
MB-HClO探针的合成:
将化合物MB-COCl(0.5g,1.44mmol)和N-(3-氨丙基)吗啉(0.26g,1.87mmol)溶解于25ml二氯甲烷中,加入到100mL圆底烧瓶中,随后将三乙胺(0.44g,4.3mmol)加入上述反应液中,室温下,搅拌2小时,柱层析分离提纯,得浅蓝色固体0.37g,产率56%,即为本发明目标探针。1H NMR(400MHz,CDCl3)δ7.29(d,J=8.0Hz,2H),6.62(d,J=4.0Hz,2H),6.56(dd,J=4.0,4.0Hz,2H),5.33(t,J=4.0Hz,1H),3.46(s,3H),3.26-3.22(m,2H),2.860(s,12H),2.27(t,J=4.0Hz,6H),1.58(t,J=4.0Hz,2H)结果如图1.13C NMR(100MHz,CDCl3)δ155.1,147.9,133.1,127.6,126.2,110.3,109.9,65.7,55.9,52.7,39.7,38.6,24.9结果如图2.HR-MS(ESI):[M+H]+calcd for C25H36N4O5S:456.2422结果如图3;结果表明,所得产物结构正确。
实施例2
荧光探针与次氯酸作用的溶液配制
用分析天平精确地称取探针固体9.1mg,并将其溶于2mLDMSO溶液中,得到浓度为10mM的探针备用溶液。在做分析实验时,根据实验需要再将储备液稀释到特定的浓度。
实施例3
荧光探针与次氯酸作用的荧光光谱测定
用浓度为10mM,pH为7.4的PBS缓冲溶液作溶剂,测定了荧光探针与次氯酸作用的荧光光谱,结果如图4。荧光探针的浓度为10μM,次氯酸的浓度依次为0、2、4、8、10、20、30、40、50μM,激发波长为620nm,收集640nm-800nm处的荧光发射峰。从图4可以看出,随着次氯酸的加入,在690nm处发射峰大幅度的增强,并且随着次氯酸浓度的增大,探针的荧光强度不断增强。如图4的插图所示,荧光强度跟次氯酸的浓度呈现线性关系。所用的荧光测定仪器为Hitachi/F-7100荧光分光光度计。图5为荧光探针与次氯酸作用的机理图,从图5中可以看出,荧光探针与次氯酸发生反应后,使得酰胺键离去,生成MB,从而导致荧光发生显著变化。
实施例4
荧光探针与次氯酸作用的紫外可见吸收光谱性质的测定
用浓度为10mM,pH为7.4的PBS缓冲溶液作溶剂,测定了荧光探针与次氯酸作用的紫外光谱图,荧光探针的浓度为10μM,次氯酸的浓度依次为0、2、4、8、10、20、30、40、50μM,从图6中可以看出,670nm处的吸收峰大幅度增强。紫外可见吸收光谱测定用的仪器为天美/UV2600型紫外可见分光光度计。
实施例5
荧光探针与次氯酸作用的响应时间的测定
为了研究荧光探针对次氯酸的响应时间,我们考察了荧光探针(10μM)在次氯酸(10μM)中的荧光光谱的变化情况,其结果如图7。从图中可以看出,该探针对次氯酸的响应时间不到2s,满足在实际样品中进行实时监测时对响应时间的要求。随着时间增加,690nm处荧光强度基本不变。
实施例6
荧光探针对次氯酸测定的选择性
在浓度为10μM的荧光探针溶液中加入HClO、Zn2+、Fe3+、Fe2+、Ca2+、Mg2+、K+、Na+、Mn2+、Cl-、CO3 2-、NO2 -、HCO3 -、I-、CH3COO-、HPO4 2-、SO4 2-、KO2、H2O2、Hcy、Cys、GSH、H2S。由图8可以发现,相对于空白测试液,各种分析物的测试液荧光强度均没有明显变化。然而,加入次氯酸的测试液的荧光强度发生了显著增强。实验结果说明探针对次氯酸具有良好的选择性。
实施例7
荧光探针在RAW264.7细胞中的毒性测试
首先,我们做了离体细胞毒性试验,如图9所示,当加入0-50μM探针,细胞的成活率均在80%以上,因此可以说明,该荧光探针可应用于检测离体活细胞内的次氯酸,并且毒性较小。
实施例8
探针在RAW 264.7细胞中与外源性次氯酸的荧光成像研究
实验前用PBS缓冲溶液清洗掉死细胞,先将稀释于PBS缓冲溶液中10μM的探针与RAW264.7细胞孵育20min然后用PBS缓冲溶液清洗细胞3次,分别加入浓度依次为0、25、50μM的次氯酸孵育20min,最后用共聚焦显微镜进行细胞成像。结果如图10所示。只加探针组观察到极为微弱的红色荧光。随着外加次氯酸浓度的增加,红色通道荧光逐渐增强。实验结果说明探针可以通过共聚焦显微镜检测到RAW 264.7细胞中外源性的次氯酸。
实施例9
探针在RAW264.7细胞中与内源性次氯酸的荧光成像研究
将稀释于PBS缓冲溶液中10μM的探针与RAW264.7细胞孵育20min;将RAW264.7细胞用脂多糖(2.5μg/mL)和佛波酯(2.5μg/mL)孵育4h,再加入10μM探针孵育20min,清洗细胞后进行成像;清除实验先用NAC(1mM)孵育细胞,然后加入脂多糖(2.5μg/mL)和佛波酯(2.5μg/mL)孵育4h,再加入10μM探针孵育20min,清洗细胞后进行成像。结果如图11所示。RAW264.7细胞与10μM探针孵育20min,红色通道几乎没有荧光;而用脂多糖和佛波酯预孵育细胞4h,再加入10μM探针后,可以明显观察到红色通道的荧光显著增强;当用抗氧化剂N-乙酰-L-半胱氨酸处理细胞,再用脂多糖、佛波酯和探针依次孵育细胞时,可以看出红色通道的荧光受到明显抑制,说明探针能够检测到细胞内源性次氯酸的动态变化。
实施例10
探针在RAW264.7细胞中与溶酶体次氯酸的荧光成像研究
在共聚焦培养皿中加入10μM的探针溶液与RAW264.7细胞共同孵育20min,而后加入10μM的次氯酸溶液孵育20min,然后分别在共聚焦培养皿中加入商业溶酶体染料200nM孵育15min,用PBS洗三次后,在共聚焦显微镜下分别在自然光、绿光、红光通道下进行成像。结果如图12所示。将红色通道所得图像a、绿色通道所得图像b和明场图像c叠加得图像d,红色通道和绿色通道具有和好的重合度,其皮尔森相关系数为0.94,图像e为荧光分布的散点图,可以看出,红色荧光区域与绿色荧光区域高度重合。图像f为线性区域的红色和绿色荧光强度做位置与强度相关分析,发现二者的变化趋势完全一致。以上结果表明,MB-HClO是一种溶酶体靶向探针,具有潜在的实际应用价值。
需要说明的是,上述实施例仅仅是实现本发明的优选方式的部分实施例,而非全部实施例。显然,基于本发明的上述实施例,本领域普通技术人员在没有做出创造性劳动的前提下所获得的其他所有实施例,都应当属于本发明保护的范围。
Claims (3)
2.一种权利要求1所述用于检测次氯酸的溶酶体靶向近红外荧光探针的制备方法,其特征在于,包括以下步骤:
(1)在250ml圆底烧瓶中,加入亚甲基蓝5g,用50ml二氯甲烷溶解得反应液,将6.63g碳酸钠溶解在50ml水中,逐滴加入到上述反应液中,然后用同样的方法将10.89g连二亚硫酸钠溶解在50ml超纯水中逐滴加入到上述反应液中,加热至40℃,磁力搅拌30分钟,随后反应液冰浴,将2.78g三光气溶于25ml二氯甲烷中逐滴加入到上述反应液中,继续搅拌1小时,全程用氮气保护,柱层析分离提纯,得到化合物MB-COCl;合成的MB-COCl不稳定,直接用于下一步反应;
(2)将0.5g化合物MB-COCl和0.26gN-(3-氨丙基)吗啉溶解于25ml二氯甲烷中,加入到100mL圆底烧瓶中,随后加入0.44g三乙胺,室温下,搅拌2小时,柱层析分离提纯,得浅蓝色固体,即目标产物探针。
3.一种权利要求1所述用于检测次氯酸的溶酶体靶向近红外荧光探针的应用,其特征在于,用于检测水溶液中次氯酸的含量或者离体活细胞溶酶体中次氯酸的含量。
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