CN111978250B - 一种荧光探针及其在检测次氯酸根的应用 - Google Patents
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Abstract
一种荧光探针及其在次氯酸根检测中的应用涉及一类在次氯酸根存在下荧光发生增强的荧光探针。本发明提供了一种可用于选择性检测细胞内或生物体次氯酸根的荧光探针。本发明在小分子1,8‑萘二甲酸亚胺作为荧光母体,母体上引入对氨基苯酚,以实现选择性地检测次氯酸根。
Description
技术领域
本发明提供了一种可用于选择性检测次氯酸根的荧光探针。在萘酰亚胺荧光母体上引入小分子对氨基苯酚结构作为与次氯酸根反应的活性中心,利用反应物与产物的荧光差别实现选择性地检测活细胞中外源性和内源性次氯酸。
背景技术
需氧细胞在正常生理代谢中产生活性氧,一般来源于线粒体等细胞器。活性氧包括次氯酸(HClO)、单线态氧(1O2)、超氧明离子(O2-)、羟基自由基(OH)及双氧水(H2O2)等,是广泛存在于生物细胞内的一种非常重要的物质,在细跑分化、细胞迁移、信号传导和细胞免疫中都起着不可或缺的作用,同时也与许多疾病的发病过程有关。次氯酸在水溶液中能够被部分电离生成次氯酸根和氯离子,在生物体细胞内,用脂多糖(LPS)和佛波豆蔻醚乙酸盐(phorbol myristate acetate,PMA)刺激细胞加速产生活性氧(ROS)和活性氮(RON),次氯酸根通常是在髓过氧化氢酶(MPO)的催化作用下由过氧化氢和氯离子反应产生的,正常生理状态下,次氯酸根浓度维持在一定的稳态,有利于对生物体组织修复,防御疾病,但是在代谢紊乱,细胞内次氯酸的浓度发生异常,甚至发生病理性变化,如关节炎、动脉粥样硬化、心血管疾病甚至癌症等。因此,开发能够及时有效的检测生物体内及环境中次氯酸根浓度的改变的探针具有重要意义。
荧光探针是有效检测生命体内次氯酸根的手段之一,相比吸光度法具有检测灵敏的优势。一个具有应用前景的荧光探针应具有作用前后荧光变化明显、对目标分子响应快、选择性好、合成简单等优点。
发明内容
本发明就是针对上述问题,提供了一种可用于选择性检测细胞内次氯酸根的荧光探针,此探针可以在生理条件下选择性地与次氯酸根作用,作用后荧光显著增强。
本发明采用如下技术方案:采用萘酰亚胺作为荧光母体,引入对氨基苯酚,利用反应物与产物的荧光差别实现选择性地检测次氯酸根,尤其是可以应用于检测活细胞中的次氯酸根。
所述荧光探针的结构式如下。
上述结构式Ⅰ表示的化合物应用于检测次氯酸根,其特征在于反应生成具有结构式II的化合物,从而导致荧光改变。
结构式Ⅰ可对次氯酸根定性、定量的检测。将浓度呈梯度变化的次氯酸根水溶液分别加入含结构式Ⅰ的水溶液中,在反应动力学线性反应时间内即可根据荧光强度读出待测溶液中次氯酸根的含量。
结构I表示的化合物可用于外源性(于外界加入细胞内)次氯酸根的细胞成像。
结构I表示的化合物可用于内源性(即外加刺激物刺激细胞髓过氧化酶产生过氧化氢、氯离子等,随即反应产生次氯酸根)次氯酸根的细胞成像。
本发明的有益效果:该化合物在次氯酸根存在下荧光发生显著改变,可用于高选择性、高灵敏性地检测次氯酸根。尤其是,该化合物可用于细胞内的次氯酸根检测,这对于深入研究次氯酸根在生物体内生理和病理过程的动力学机理具有重要意义。
附图说明
图1本发明提供的荧光探针NB4OH检测次氯酸根的原理示意图;
图2实施例1中合成的探针NB4OH的1H NMR(a),13C NMR(b)谱图,HPLC-MS谱图(c);
图3实施例2中荧光探针NB4OH水溶液的紫外可见吸收光谱(a)、荧光激发光谱(b)、发射光谱(c);
图4实施例3中荧光探针NB4OH对次氯酸根的选择性示意图;
图5实施例4中荧光探针NB4OH对不同浓度的次氯酸根响应的示意图及反应速率与次氯酸根浓度的线性关系;
图6实施例5中荧光探针NB4OH在体外次氯酸根被抑制作用下示意图;
图7实施例6中荧光探针NB4OH在Hela细胞中外源性次氯酸根成像示意图;
图8实施例7中荧光探针NB4OH在RAW264.7细胞中内源性次氯酸根成像示意图;
图9实施例8中荧光探针NB4OH在RAW264.7细胞中内源性次氯酸根抑制成像示意图;
具体实施方式
实施例用于进一步说明本发明,但本发明不限于实施例。
实施例1(探针的合成):如图2,实施例所采用的探针化合物的结构用代号NB4OH表示。
NB4OH的合成:
250mL三口烧瓶真空/氮气置换三次,加入50ml的乙醇溶解4-溴-1,8-萘酐和1.78ml的正丁胺,78℃搅拌12h,真空下40℃加热蒸干。将所得固体经硅胶柱层析纯化(用石油醚和乙酸乙酯做洗脱剂(石油醚和乙酸乙酯体积比=10:1))得化合物Butylamine-4-Bromo-1,8-naphthalic anhydride(浅绿色固体)。取该化合物1g,4-氨基苯酚394mg,t-BuONa 723mg,Pd2(dba)3 275mg,溶于10.0ml甲苯,90℃搅拌7小时。反应结束后,真空下加热蒸干。将所得固体经硅胶柱层析纯化(用石油醚和乙酸乙酯做洗脱剂(石油醚和乙酸乙酯体积比=1:2)),利用制备型色谱再次纯化,最终的到目标化合物NB4OH(红色固体)。
1H NMR(400MHz,DMSO-d6)δ9.53(s,1H),9.25(s,1H),8.82(dd,J=8.5,1.1Hz,1H),8.47(dd,J=7.4,1.1Hz,1H),8.19(d,J=8.5Hz,1H),7.74(dd,J=8.5,7.3Hz,1H),7.24–7.14(m,2H),6.93–6.83(m,3H),4.01(dd,J=8.2,6.5Hz,2H),1.59(tt,J=7.9,6.4Hz,2H),1.34(h,J=7.4Hz,2H),0.92(t,J=7.3Hz,3H).
13C NMR(101MHz,DMSO)δ164.16,163.27,155.68,150.23,134.21,131.36,131.18,130.01,129.22,126.86,125.17,122.40,121.07,116.61,109.79,106.54,39.44,30.27,20.29,14.21.
HRMS:m/z C22H21N2O3 +Calcd 361.1552,found[M]+(361.1536)
实施例2:如图3,荧光探针NB4OH的紫外可见吸收光谱(a)、荧光激发光谱(b)、发射光谱(c):
将NB4OH溶于硼酸硼砂缓冲液(100mM)中,配置成20uM的溶液。取3mL溶液加入1cmⅹ1cmⅹ4cm(长ⅹ宽ⅹ高)的比色皿中,测量该工作液的紫外可见吸收光谱(a)、荧光激发光谱(b)、发射光谱(c);结果显示探针NB4OH的吸收波长为460nm,探针NB4OH的最大激发波长为468nm,探针NB4OH最大发射波长为540nm。
实施例3:(NB4OH对次氯酸根的选择性):
配置亚硝酸钠、七水合硫酸亚铁、三聚氰胺、氯化锌、碳酸氢钠、磷酸二氢钠、无水碳酸钠、六氰合铁酸钾、重铬酸钾、硫化钠、无水乙酸钠、无水氯化锂、氯化锰、氯化铅、六水合硝酸锌、乙酸锌、六水合氯化镁、氯化钡、氯化镉、氧化亚铜、碱式碳酸铜、硫酸亚铁铵、碘化钾、L-半胱氨酸、5-羟色胺、牛磺酸、聚乙二醇、环糊精、十二烷基苯磺酸钠、L-甲硫氨酸、L-组氨酸、谷胱甘肽(氧化型)、谷胱甘肽(氧化型)、双氧水、NO·(SNP溶于去离子水配置成工作液100uM)、ROO·(偶氮二异丁脒盐酸盐溶于去离子水配置成工作液)、ONOO-(亚硝酸钠和双氧水以1:1(c/c)配置成工作液)、·OH(Fe2+和双氧水以1:1(c/c)配置成工作液)和次氯酸钠溶液(100mM)。配置NB4OH(50uM)的DMSO溶液。每个反应在200ul体系,体系中包含80ul NB4OH(50uM),10ul相应的以上配置的离子溶液和110ul去离子水。使用全波长扫描式多功能读数仪及96孔酶标板进行测量,探针终浓度为20uM。测量该工作液的荧光发射光谱,λex=460nm,光栅宽度为5nm,λem=540nm。
NB4OH对次氯酸钠的选择性实验结果如图4所示,横坐标为以上配置的离子,纵坐标F/F0(F表示相应以上配置的离子在波长为540nm处的荧光强度,F0表示只有探针本身的溶液即对照在波长为540nm处的荧光强度)。图4表明NB4OH对次氯酸根具有较好的选择性,该体系荧光显著增强,其余离子无明显响应。
实施例4(NB4OH对次氯酸根的定量检测):
将100mM的次氯酸钠溶液稀释至25mM。每个反应的体系:80ul NB4OH(50uM),0、1、2、3、4、5、6、7、8ul次氯酸钠(25mM)和120-112ul去离子水(最终体系体积200ul)。使用全波长扫描式多功能读数仪及96孔酶标板进行测量。测量该工作液的荧光发射光谱,λex=460nm,光栅宽度为5nm,λem=540nm。结果显示:如图5,随次氯酸根浓度的增长,NB4OH与次氯酸响应产生的代谢物的生成速率成比例增长。
实施例5(NB4OH的抑制实验):
配置还原型谷胱甘肽(10mM)的水溶液。使用全波长扫描式多功能读数仪及96孔酶标板进行测量。测量该工作液的荧光发射光谱,λex=460nm,光栅宽度为5nm,λem=540nm。对照组体系80ul NB4OH(50uM)在120ul去离子水中,测得的荧光值F0,其余每个反应体系(总体积200ul):80ul NB4OH(50uM)、100ul去离子水以及10ul的次氯酸根(50mM)和10ul还原型谷胱甘肽(10mM)混合液,80ul NB4OH(50uM)和10ul的次氯酸根(50mM)37摄氏度反应30min之后再加入10ul还原型谷胱甘肽(10mM)。结果显示:如图6,在混合液中,次氯酸根与还原性物质反应,因此探针没有响应;探针和次氯酸根响应后在与还原性物质反应,荧光值无明显变化,说明不是氧化还原型探针。再次证明NB4OH是次氯酸根的探针底物。
实施例6(探针NB4OH用于Hela细胞中外源性次氯酸根的检测):
Hela细胞按照American type Tissue Culture Collection规定进行培养。接种于35mm×12mm(直径×高度)的培养皿中培养24h使之贴壁。使用前将培养液弃去,用100mM硼酸硼砂缓冲液洗三次。对照实验,Hela cells同样按照American type Tissue CultureCollection规定进行培养,加10uM 1ml NB4OH(DMSO2%)30min原位观察。实验组:加100uM1ml次氯酸钠溶液孵育10min后加入10uM 1ml NB4OH(DMSO2%)的硼酸硼砂缓冲溶液,30min后原位观察。使用共聚焦显微镜Olympus FV1000(Ex.405nm)镜头进行观察以及图像采集。结果显示:如图7,HELA细胞荧光图像(b)亮度明显高于对照组(a)。该实验证明探针NB4OH可以用于细胞中外源性次氯酸根的检测。
实施例7(探针NB4OH用于RAW264.7细胞中内源性次氯酸根的检测):
小鼠巨噬细胞RAW264.7(在受到刺激后会产生髓过氧化物酶,MPO)按照Americantype Tissue Culture Collection规定进行培养。对照组细胞:用含有10.0μM NB4OH的硼酸硼砂缓冲液孵育RAW264.7细胞30分钟后,将细胞用缓冲液洗涤3次,置于共聚焦荧光显微镜下拍照;另一组细胞:加入LPS(终浓度0.5μg/mL)孵育4h后,加入PMA(终浓度1μg/mL)刺激细胞30分钟,再用含有10.0μM NB4OH的硼酸硼砂缓冲液孵育RAW264.7细胞30分钟,将细胞用缓冲液洗涤3次后,置于共聚焦荧光显微镜下拍照。如图8,结果显示:受刺激的细胞(b),荧光图像亮度明显高于对照组(a)。该实验证明探针NB4OH可以用于细胞中内源性次氯酸根的实时检测。
实施例8(探针NB4OH用于RAW264.7细胞中内源性次氯酸根抑制的检测):
小鼠巨噬细胞RAW264.7(在受到刺激后会产生髓过氧化物酶,MPO)按照Americantype TissueCulture Collection规定进行培养。对照组细胞:加入双氧水(终浓度100uM)孵育30min后,用含有10.0μM NB4OH的硼酸硼砂缓冲液孵育RAW264.7细胞5、30分钟,分别置于共聚焦荧光显微镜下拍照;另两组组细胞:加入4-氨基苯甲酰肼(终浓度10uM)(图9(b))、水杨基氧肟酸(终浓度50uM)(图9(c))孵育30min后,加入双氧水(工作液100uM)孵育30min后,用含有10.0μM NB4OH的细胞培养液孵育RAW264.7细胞5、30分钟,分别置于共聚焦荧光显微镜下拍照;如图9,结果显示:受抑制的细胞(b)(c),荧光图像亮度明显低于对照组(a)。该实验证明内源性次氯酸根被抑制时,没有荧光变化,从而说明探针NB4OH可以用于细胞中内源性次氯酸根的检测。
Claims (7)
2.根据权利要求1所述的应用,其特征在于,所述荧光探针用于水溶液中或细胞的次氯酸根检测,其作用模型符合动力学。
4.根据权利要求3所述的应用,其特征在于,结构I表示的化合物与次氯酸根作用后,540nm处检测得的荧光强度正比于次氯酸根的浓度。
5.根据权利要求4所述的应用,其特征在于,结构I表示的化合物用于外源性次氯酸根的细胞成像。
6.根据权利要求3所述的应用,其特征在于,结构I表示的化合物用于内源性次氯酸根的细胞成像。
7.根据权利要求6所述的应用,其特征在于,利用所述荧光探针实现细胞内次氯酸根的荧光成像。
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