CN108997289B - 一种靶向脂滴的次氯酸比率荧光探针及其应用 - Google Patents

一种靶向脂滴的次氯酸比率荧光探针及其应用 Download PDF

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CN108997289B
CN108997289B CN201811115691.4A CN201811115691A CN108997289B CN 108997289 B CN108997289 B CN 108997289B CN 201811115691 A CN201811115691 A CN 201811115691A CN 108997289 B CN108997289 B CN 108997289B
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苗俊英
赵宝祥
武文丽
马汉林
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Abstract

本发明公开了一种基于FRET机理的靶向脂滴的次氯酸比率荧光探针，是以香豆素荧光团作为能量供体、(E)‑2‑(3‑(4‑(二取代氨基)苯乙烯基)‑(5,5‑二甲基)环己‑2‑烯‑1‑亚基)丙二腈作为能量受体，酰基哌嗪为链接基团；其化学结构如式(I)所示。本发明的探针可以选择性地与次氯酸作用，随着次氯酸浓度的增加，其荧光发射强度在470nm处逐渐增强，在672nm处逐渐减弱；二者比值(I486/I609)与次氯酸浓度在一定范围内呈线性关系。实现了细胞内的比率成像，有望在工业生产和临床医学中发挥作用，具有广阔的应用前景。

Description

一种靶向脂滴的次氯酸比率荧光探针及其应用
技术领域
本发明涉及一种比率荧光探针及其应用，尤其涉及一种基于荧光共振能量转移机理的靶向脂滴的次氯酸比率荧光探针及其应用；属于有机小分子荧光探针领域。
背景技术
在生物体内次氯酸是由双氧水和氯离子经髓过氧化酶催化生成的，是最重要的活性氧之一。作为内源性杀菌剂，次氯酸能够抵抗细菌入侵，发挥重要的生理作用；另外，体内次氯酸水平与某些疾病密切相关，如：肾脏疾病、关节炎、肺损伤、动脉硬化以及肿瘤等。因此，开发生物体内次氯酸成像技术、实时检测细胞内次氯酸的时空与浓度分布，研究体内次氯酸的生理、病理作用，具有重要的意义。
次氯酸荧光探针具有高选择性、超灵敏性及快速响应等优点，吸引了科学家的广泛关注[H.Zhu et al,J.Am.Chem.Soc.,2014,136,12820；Q.A.Best et al,J.Am.Chem.Soc.,2013,135,13365]；比率荧光探针因其能够有效消除环境、探针浓度及激发光强度的干扰而备受青睐[L.Yuan et al,Acc.Chem.Res.,2013,46,1462]。在众多类比率荧光探针中，基于FRET机理的比率荧光探针是由能量供体荧光团、能量受体荧光团通过连接单元构成。能量受体接受能量供体转移的能量而发射荧光。供体荧光和受体荧光强度依据被检测物的浓度变化而发生变化，因而两者的荧光强度比率与被检测物的浓度呈现线性关系。为了兼顾两个发射波长之间的距离和能量传递效率，需要研究开发能量供体及能量受体荧光团，构成新的FRET体系。同时，迫切需要开发靶向亚细胞器的且应用性质优良的比率荧光探针。
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基于FRET机理的靶向脂滴的次氯酸比率荧光探针及其应用。
本发明所述基于FRET机理的靶向脂滴的次氯酸比率荧光探针，其特征在于：所述比率荧光探针命名为XHZ，由能量供体香豆素荧光团、能量受体(E)-2-(3-(4-(二取代氨基)苯乙烯基)-(5,5-二甲基)环己-2-烯-1-亚基)丙二腈与链接基团酰基哌嗪构成；其化学结构如式(I)所示：
Figure BDA0001810505280000011
上述基于FRET机理的靶向脂滴的次氯酸比率荧光探针的制备方法，步骤是：用已知方法合成4-(4-(7-(二乙胺基)-2-氧代-2H-苯并吡喃-3-羰基)哌嗪-1-基)苯甲醛以及2-(3,5,5-三甲基环己-2-烯-1-亚基)丙二腈，然后进行缩合反应得到所述次氯酸比率荧光探针。
本发明所述基于FRET机理的靶向脂滴的次氯酸比率荧光探针在检测含次氯酸样品中的应用。
其中：所述含次氯酸样品优选是生物细胞或含次氯酸的溶液。
本发明所述的基于FRET机理的次氯酸比率荧光探针在无次氯酸的条件下，能量供体香豆素荧光团被激发后将能量传递给能量受体，能量受体发射荧光；在次氯酸存在下，能量受体单元中的双键与次氯酸发生反应生成环氧环(见式(Ⅱ)和图1)，从而将阻断能量转移，能量供体被激发时，能量供体发射荧光。根据次氯酸的浓度不同，两个发射波长的荧光强度发生改变；从而达到比率荧光检测次氯酸的效果。
Figure BDA0001810505280000021
具体的：配制上述靶向脂滴的次氯酸比率荧光探针的N,N-二甲基甲酰胺(DMF)与磷酸盐(0.01M)缓冲液(v/v＝4：6，pH＝7.4，)的溶液，分别加入定量的活性氧或活性氮的水溶液，如：t-BuOOH,t-BuOO-,H2O2,HO-,NO,NOOO-,1O2,-O2,HOCl以及其他离子。然后对上述溶液进行荧光测试，结果表明上述次氯酸比率荧光探针对次氯酸有很好的选择性，见图2。
本发明所述的荧光探针随次氯酸浓度的增加，470nm处荧光强度逐渐增强，672nm处荧光强度逐渐减弱；二者比值相对次氯酸浓度在一定范围内呈线性关系。所以该探针能够定量检测低浓度的HOCl，见图3。
在RAW264.7活细胞中加入上述次氯酸比率荧光探针和LipidTOXTM中性脂滴染料的共定位，见图4。(a)探针XHZ(405-640nm)；(b)LipidTOXTM中性脂滴,Ex＝639nm,Em＝640-700nm；(c)透射光；(d)重叠(a)与(b)；(e)共定位系数0.87。
综上，本发明所述的基于FRET机理的靶向脂滴的次氯酸比率荧光探针不仅可以定量检测低浓度次氯酸，而且能够用于细胞内的比率成像，具有广阔的应用前景。
附图说明
图1为本发明所述的基于FRET机理的次氯酸比率荧光探针与次氯酸生成产物的高分辨质谱。
图2为本发明所述的基于FRET机理的次氯酸比率荧光探针(XHZ)对各种活性氧以及离子的选择性。
图3为本发明所述的基于FRET机理的次氯酸比率荧光探针在470nm与672nm处的荧光强度比值与次氯酸浓度间的线性关系图。
图4为本发明所述的基于FRET机理的次氯酸比率荧光探针在RAW264.7细胞内与脂滴染料共定位荧光显微成像图。
其中：(a)探针XHZ(405-640nm)；(b)LipidTOXTM中性脂滴,Ex＝639nm,Em＝640-700nm；(c)透射光；(d)重叠(a)与(b)；(e)共定位系数0.87。
具体实施方式
实施例1本发明所述的基于FRET机理的次氯酸比率荧光探针的制备
4-(4-(7-(二乙胺基)-2-氧代-2H-苯并吡喃-3-羰基)哌嗪-1-基)苯甲醛(100mg,0.23mmol)和2-(3,5,5-三甲基环己-2-烯-1-亚基)丙二腈(53mg,0.28mmol)溶于20mL乙醇，回流状态下搅拌5小时。减压蒸馏除去反应溶剂，粗产品经柱层析纯化得到固体47mg，即为本发明所述的基于FRET机理的次氯酸比率荧光探针(命名为：XHZ)。产率：34％。
结构确认谱图数据，1H NMR(500MHz,DMSO-d6):δ＝8.02(s,1H),7.59(d,J＝10Hz,2H),7.51(d,J＝10Hz,1H),7.27-7.20(m,2H),6.98(d,J＝10Hz,2H),6.79-6.83(m,1H),6.76(d,J＝10Hz,1H),6.61-6.57(m,1H),3.72(s,2H),3.48-3.28(m,10H),2.59-2.53(m,4H),1.14(t,J＝15Hz,6H),1.12(s,6H)；13C NMR(75MHz,DMSO-d6):δ＝170.55,164.61,161.04(2C),158.91,157.37,157.13,151.88,144.42,138.89,130.61,130.00(2C),126.68,126.25,121.52,116.31,115.29(2C),114.73,113.91,109.91,107.64,96.83,74.63,46.22(2C),44.65,32.11,27.93,26.69(2C),25.34(2C),24.69(2C),12.77(2C)；HRMS(m/z):[M+H]+计算值(C37H40N5O3 +)＝602.3126,发现值＝602.3114；[M+Na]+计算值(C37H39N5NaO3 +)＝624.2945,发现值＝624.3069。
上述次氯酸比率荧光探针的制备如下式所示：
Figure BDA0001810505280000031
实施例2
向装有10μM该次氯酸探针的10ml容量瓶中，用微量进样器分别加入100当量的:空白,t-BuO-,HO-,H2O2,O2 -,OONO-,NO,1O2,t-BuOOH，K+,Na2+,Al3+,Cu2+,Ca2+,Fe2+,Pb2+，F-,Cl-,Br-,I-,NO2 -,CO3 2-,CH3CO2 -,HCO3 -,S2O3 2-,SO4 2-,SCN-,HS-,HSO3 2-,H2PO3-,HPO4 2-,Hcy,Cys，GSH，进行荧光测试。
结果表明，该探针只对HOCl有很好的响应和选择性。见图2。
实施例3
向装有2.5μM该次氯酸探针的10ml容量瓶中，用微量进样器分别加入不同当量的HOCl，进行荧光测试。
结果表明，470nm处荧光强度与672nm处荧光强度的比值相对次氯酸浓度在一定范围内呈线性关系。见图3。
实施例4
细胞内共定位荧光成像测试：
将RAW264.7细胞转移到小的玻璃瓶中孵化24h后，用该次氯酸探针(2μM)溶液和中性脂滴染料孵化半小时，然后PBS洗涤三次进行共聚焦细胞成像检测。
所用激发波长为405nm，探针的蓝色通道收集波长为405-550nm，中性脂滴激发波长639nm，红色通道收集波长为640-700nm。成像结果见图4。其中：(a)探针XHZ(405-640nm)；(b)LipidTOXTM中性脂滴,Ex＝639nm,Em＝640-700nm；(c)透射光；(d)重叠(a)与(b)；(e)共定位系数0.87。

Claims (2)

1.一种检测次氯酸的比率荧光探针，其特征在于：所述比率荧光探针由能量供体香豆素荧光团、能量受体(E)-2-(3-(4-(二取代氨基)苯乙烯基)-(5,5-二甲基)环己-2-烯-1-亚基)丙二腈和连接基团酰基哌嗪构成；其化学结构如式(I)所示：
Figure FDA0003442409030000011
2.权利要求1所述检测次氯酸的比率荧光探针在不以疾病的诊断为目的检测含有次氯酸的样品中的应用。
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