CN105017196B - 一种检测肼的近红外比率荧光探针及其应用 - Google Patents
一种检测肼的近红外比率荧光探针及其应用 Download PDFInfo
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Abstract
本发明公开了一种近红外的肼比率荧光探针,所述探针是含双香豆素的4‑(2’‑甲羧基苯基)‑2‑(7’‑二乙胺基香豆素)‑7‑二乙胺基苯并吡喃高氯酸盐,其化学结构式如式(I)所示。本发明的探针可以选择性地与N2H4作用,由绿色变为黄色,可肉眼分辨,荧光由红色变为蓝绿色,具有非常好的荧光比率响应效应,也可以通过紫外吸收和荧光光度法进行分析。不仅可以比率检测N2H4,实现细胞内的比率成像,而且做成的硅胶板可以迅速裸眼检测气态N2H4的含量。有望在工业生产和生物科学中发挥作用,具有广阔的应用前景。
Description
技术领域
本发明涉及一种近红外荧光探针,尤其涉及一种用于检测肼的近红外荧光探针及其应用;属于有机小分子荧光探针领域。
背景技术
香豆素母环为苯并吡喃酮结构,本身具有较大的摩尔消光系数和量子产率,有多个位点可以修饰,并且能够达到近红外发光,可用于发光材料、化学传感器以及标记生物分子等。近几年利用比率荧光效应检测小分子肼的研究得到不断发展。
肼是一种非常重要的活性碱和强还原剂,在化学领域可以用作催化剂、乳化剂、医药中间体、纺织染料、摄影化学品等。同时肼作为一种高能燃料推进剂在导弹、卫星和火箭推进系统中发挥着重要作用。但是,肼也是美国环保署规定的一种毒性物质,通过呼吸和皮肤接触进入人体,对人体的肝、肾、肺及神经系统造成伤害。因此限定其在饮用水中的含量不可超过10ppb。鉴于肼的以上性质,在生物体中方便快捷检测肼尤为重要。
目前检测肼的常用方法有电化学法和化学发光法,其中荧光光谱分析法有着操作简单、灵敏度高、选择性好、生物相容性好等优势。已申请的专利【CN103923071A】、【CN104109126A】展示了特异性选择肼的荧光探针,但是都存在着波长短、无法检测气态肼、无法实现细胞成像等缺点。鉴于此,开发近红外发光,具有细胞成像能力,而且可以比率检测、裸眼识别的肼的荧光探针成为目前亟待解决的课题。
发明内容
针对现有技术的不足,本发明要解决的问题是提供一种检测肼的近红比率荧光探针及其应用。
本发明所述的近红外比率荧光探针,其特征在于:所述荧光探针是含双香豆素结构的4-(2’-甲羧基苯基)-2-(7’-二乙胺基香豆素)-7-二乙胺基苯并吡喃高氯酸盐,其化学结构式如式(I)所示,
上述的近红外比率荧光探针的制备方法是:由已知方法合成的2-(2-羟基-4-二乙胺基苯甲酰基)苯甲酸和3-乙酰基-7二乙胺基香豆素在浓硫酸中控温反应,反应液冷却、加高氯酸氧化得到目标荧光探针。
上述的近红外比率荧光探针在检测含肼的样品中的应用。
上述应用中:所述含肼的样品优选是生物细胞、血清、含肼的溶液或者气态肼。
本发明所述的近红外比率荧光探针在制备裸眼检测肼的硅胶板中的应用。
本发明所述的探针4-(2’-甲羧基苯基)-2-(7’-二乙胺基香豆素)-7-二乙胺基苯并吡喃高氯酸盐的羧基在水溶液可以先与肼生成酰肼,再形成螺环,由大共轭体系的红光变成香豆素的蓝色荧光,从而达到比率检测的效果。反应产物质谱如图1。
具体的:配制4-(2’-甲羧基苯基)-2-(7’-二乙胺基香豆素)-7-二乙胺基苯并吡喃高氯酸盐的PBS缓冲液(DMSO:PBS=2:3,v:v,pH=7.4)的溶液,分别定量加入微升级的N2H4,CH3CO2 -,Br-,H2PO4 -,HCO3 2-,HPO4 2-,HSO3 -,I-,NO2 -,NO3 -,SO3 2-,SO4 2-,Ca2+,Cu2+,Fe3+,K+,Mg2+,Na2S,Zn2+的水溶液。通过紫外可见分光光度法和荧光分光光度法测试其对常见阴离子、阳离子的选择性和响应能力。结果显示该探针对肼有很好的选择性,加入痕量肼前后对照显示紫外吸收和荧光发射波长分别发生了167和201nm的蓝移,具有非常好的比率响应。见图2,3,4。
在100%胎牛血清中加入5μM的该探针孵育和不同浓度的N2H4共同孵育2h。纯血清在两个通道基本无荧光,探针在蓝色通道显弱光,红色通道发强荧光,随着N2H4浓度的增加,蓝色荧光逐渐加强,红色荧光逐渐减弱。见图5。
在加入5.0μM的该探针的HeLa活细胞中不加入N2H4和加入不同浓度的N2H4对照细胞染色荧光显微成像变化。荧光成像显示该探针渗透进细胞内。对照组细胞蓝色通道有微弱荧光,红色通道亮色荧光。加入不同浓度的N2H4时,对照组细胞蓝色通道显亮荧光,红色通道荧光淬灭。见图6。
将0.1mg/mL的该探针的硅胶板放置于盛有不同胺和不同浓度肼的容量瓶的瓶口,10min后置于紫外灯下拍照。(a)组是不同的胺类化合物(从左向右以此为:空白、氨水、甲胺、硫脲、乙二胺、过氧化氢、尿素、肼),结果显示只有肼能使硅胶板变色;(b)组是不同浓度的肼,紫外灯下显示硅胶板随肼浓度增大,由红色变成蓝色,见图7。
本发明提供的近红外比率荧光探针可以选择性地与N2H4作用,由绿色变为黄色,可肉眼分辨,荧光由红色变为蓝绿色,具有非常好的荧光比率响应效应,也可以通过紫外吸收和荧光光度法进行分析。不仅可以比率检测N2H4,实现细胞内的比率成像,而且做成的硅胶板可以迅速裸眼检测气态N2H4的含量。有望在工业生产和生物科学中发挥作用,具有广阔的应用前景。
附图说明
图1为探针与N2H4加成产物的高分辨质谱。
图2为探针的PBS缓冲液(DMOS:PBS=2:3,v:v,pH=7.4)中加入和不加入N2H4时的紫外吸收图谱。
图3为探针的PBS缓冲液(DMOS:PBS=2:3,v:v,pH=7.4)中加入和不加入N2H4时的荧光发射图谱。
图4为探针的PBS缓冲液(DMOS:PBS=2:3,v:v,pH=7.4)中加入多种阴离子和阳离子的荧光发射图谱。
图5为探针在胎牛血清中的荧光成像。37℃条件下,在含有不同浓度肼(0,10,50,100,500,1000μM)的牛血清溶液中加入5.0μM的探针培养2h的荧光强度。
图6为探针在HeLa细胞内荧光显微成像图。
其中:在37℃条件下,HeLa细胞在加入5.0μM的探针的细胞培养液中培养1小时;PBS缓冲溶液洗涤三次后,再加入不同浓度的N2H4(0,10,50,100,500,1000μM)培养2小时的图像。
图7为探针作为检测气态肼的硅胶板在紫外灯下获得的照片。
其中:用0.1mg/mL的探针溶液浸泡硅胶板,烘干制成条状,然后放置于盛有不同胺和不同浓度肼的容量瓶的瓶口,10min后置于紫外灯下拍照。(a)组是不同的胺类化合物(从左向右以此为:空白、氨水、甲胺、硫脲、乙二胺、过氧化氢、尿素、肼),结果显示只有肼能使硅胶板变色;(b)组是不同浓度的肼。
具体实施方式
实施例1
由已知方法合成的2-(2-羟基-4-二乙胺基苯甲酰基)苯甲酸和3-乙酰基-7二乙胺基香豆素在浓硫酸中控温反应,反应液冷却、加高氯酸氧化得到具有红色荧光的4-(2’-甲羧基苯基)-2-(7’-二乙胺基香豆素)-7-二乙胺基苯并吡喃高氯酸盐。具体是:
将2-(2-羟基-4-二乙胺基苯甲酰基)苯甲酸(3,5.0mmol),3-乙酰基-7二乙胺基香豆素(5.0mmol)加入到5mL浓硫酸中,加热至90℃控温8h,冷至室温,加入10g冰,再加入1mL70%高氯酸搅拌,有黑色固体析出,抽滤,水洗三次,粗产品用乙醇重结晶得到墨绿色固体即为4-(2’-甲羧基苯基)-2-(7’-二乙胺基香豆素)-7-二乙胺基苯并吡喃高氯酸盐(BPCC),熔点>300℃,产率50%。
红外测定(KBr,cm-1):3485,3195,2994,2379,1729,1634。
核磁共振氢谱测定:1H NMR(400MHz,DMSO-d6):δ=13.27(s,-COOH,1H),8.80(s,1H),8.00(d,J=7.5Hz,1H),7.81(t,J=7.2Hz,1H),7.73-7.69(m,2H),7.46(d,J=7.5Hz,1H),7.00(d,J=8.7Hz,2H),6.64-6.71(m,3H),3.51(q,J=6.8Hz,8H),1.19(t,J=6.8Hz,12H)。
核磁共振碳谱测定:13C NMR(100MHz,DMSO-d6):12.40,44.20,44.43,96.04,96.80,108.16,110.39,128.44,130.02,131.30,134.36,152.46,156.62,158.33,168.09。
高分辨质谱:m/z[M]+calcd for C33H33N2O5:537.2389,found 537.2380。
4-(2’-甲羧基苯基)-2-(7’-二乙胺基香豆素)-7-二乙胺基苯并吡喃高氯酸盐可以与N2H4在水溶液中反应首先生成酰肼再形成螺环,由大共轭体系的红光变成香豆素的蓝色荧光,从而达到比率检测的效果。反应产物质谱见图1。其反应过程如下式所示:
实施例2
用微量注射器分别向盛有10mL配好的探针的PBS缓冲液(DMSO:PBS=2:3,v:v,pH=7.4)中,分别定量加入10当量的N2H4,CH3CO2 -,Br-,H2PO4 -,HCO3 2-,HPO4 2-,HSO3 -,I-,NO2 -,NO3 -,SO3 2-,SO4 2-,Ca2+,Cu2+,Fe3+,K+,Mg2+,Na2S,Zn2+的水溶液,作用2小时后进行紫外可见分光光度法和荧光分光光度法测试,显示探针对N2H4有很好的选择性,加入N2H4前后对照显示紫外吸收波长和荧光发射波长分别发生了167和201nm的蓝移,具有非常好的比率响应。见图2,3,4。
实施例3
胎牛血清中荧光测试。
在37℃条件下,100%胎牛血清中加入5μM的探针孵育和不同浓度的N2H4(0,10,50,100,500,1000μM)共同孵育2h。纯血清在两个通道基本无荧光,探针在蓝色通道显弱光,红色通道发强荧光,随着N2H4浓度的增加,蓝色荧光逐渐加强,红色荧光逐渐减弱,见图5。
实施例4
细胞内荧光成像测试:
在37℃条件下,HeLa细胞在加入5.0μM的探针的细胞培养液中培养1小时;PBS缓冲溶液洗涤三次后,再加入不同浓度的N2H4(0,10,50,100,500,1000μM)培养2小时。
荧光成像显示探针渗透进细胞内。对照组细胞蓝色通道有微弱荧光,红色通道亮色荧光。加入不同浓度的N2H4时,对照组细胞蓝色通道显亮荧光,红色通道荧光淬灭,见图6。
实施例5
本发明的探针作为气态肼测试:
用0.1mg/mL的探针溶液浸泡硅胶板,烘干制成条状,然后放置于盛有不同胺和不同浓度肼的容量瓶的瓶口,10min后置于紫外灯下拍照。(a)组是不同的胺类化合物(从左向右以此为:空白、氨水、甲胺、硫脲、乙二胺、过氧化氢、尿素、肼),结果显示只有肼能使硅胶板变色;(b)组是不同浓度的肼。
结果:其他含化合物不能引起探针响应;随肼浓度增大,紫外灯下显示硅胶板由红色变成蓝色。紫见图7。
Claims (3)
1.一种检测肼的近红外比率荧光探针在制备裸眼检测含肼样品试剂中的应用,其中所述荧光探针是含双香豆素的4-(2’-甲羧基苯基)-2-(7’-二乙胺基香豆素)-7-二乙胺基苯并吡喃高氯酸盐,其化学结构式如式(I)所示,
2.如权利要求1所述的应用,其特征在于:所述含肼样品是生物细胞、血清、含肼的溶液或者气态肼。
3.一种检测肼的近红外比率荧光探针在制备裸眼检测肼的硅胶板中的应用,其中所述荧光探针是含双香豆素的4-(2’-甲羧基苯基)-2-(7’-二乙胺基香豆素)-7-二乙胺基苯并吡喃高氯酸盐,其化学结构式如式(I)所示,
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