CN114736223A - 一种新型近红外荧光检测试剂的制备及其体外诊断应用 - Google Patents
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Abstract
Description
技术领域
本发明属于分析化学技术领域,涉及一种新型特异性识别过氧化氢的近红外荧光分子探针的制备方法,特别还涉及到该荧光分子探针在环境和生物体内中过氧化氢检测方面的应用。
背景技术
过氧化氢(Hydrogen peroxide,H2O2)是活性氧物种(ROS)中的重要成员,在体内通过氧气的代谢及酶的催化而产生,在生理、衰老和疾病发展中起着至关重要的作用。如适量的H2O2不仅可活化免疫细胞、还可促进细胞的生长和增殖。然而过量的H2O2则与神经退行性疾病,DNA损伤、突变,遗传不稳定和癌症有关。如细胞中H2O2的过度积累会产生氧化应激从而引起广泛的细胞损伤。因此,开发一种简单高效的检测方法,以用于生命系统中H2O2的实时检测,对进一步了解和防治与其相关的疾病,有着重要的意义和价值。
目前,生物体内H2O2的检测方法主要包括电化学方法、元素分析以及质谱等方法,这些传统方法有着前处理复杂、样品损伤大、且无法实时监测等缺陷。相比而言,荧光探针检测法则具有成本低廉、灵敏度高、特异性强、响应速度快、能够进行实时可视化检测等优点,已逐渐成为研究的热点和重点。如CN 106632436 B报道了一个可实现过氧化氢高选择性、高灵敏度检测的荧光探针,CN 108752373 A也报道了一个合成简单,使用方便的过氧化氢荧光探针,但其最大发射波长都在紫外区(400 nm-600nm),导致组织穿透能力弱、组织伤害性强,且容易受到生物体内背景荧光的干扰,从而导致探针的灵敏度和准确度受到影响。
发明内容
针对现有技术的不足,本发明提供一种新型近红外荧光检测试剂,可用于水溶液和生物体系中H2O2的检测,从而实现H2O2的体外诊断。
本发明的第二个目的是在于提供一种操作简单、原料易得的制备所述荧光分子探针的方法。
为了实现以上技术目的,本发明提供了一种荧光探针,该荧光探针的结构如式I所示:
式I。
本发明所述的H2O2荧光探针化合物的制备方法,包括如下步骤:
1)将化合物1和化合物2溶于乙醇中,向反应体系中加入哌啶,加热回流至反应结束。反应完成后,将反应体系冷却至室温,减压浓缩后可获得红色固体,即为化合物3。
2)将化合物3和对溴甲基苯硼酸频哪醇酯溶于DMF中,加入K2CO3,加热回流至反应完全。取下反应,倒入水中,分别用水、饱和NaHCO3溶液及饱和食盐水萃取,合并有机层,用无水硫酸镁干燥后浓缩,经柱层析纯化后,可得目标分子探针。
该探针的合成路线为
本发明所述的过氧化氢荧光探针化合物的应用,可用于测试细胞、组织和水等多个体系中的H2O2含量。
本发明通过实验验证,所述荧光探针在pH=7.4水溶液中,由于苯硼酸酯基的淬灭作用,荧光探针在703nm处几乎没有荧光发射峰,而加入H2O2之后,苯硼酸酯基键断裂,探针在近红外区(703nm)出现了近红外荧光发射峰,且随着H2O2浓度的增加,其荧光强度逐渐增强。
为相对现有技术,本发明的技术方案带来的有益技术效果:
本发明所涉及的一种新型近红外荧光检测试剂,具有以下优势:
(1)本发明的荧光探针具有合成简单的优点,该探针仅经2步即可合成,均使用常用试剂,后处理简单,成本低廉,适合大范围推广;
(2)本发明的荧光检测体系具有灵敏度高和选择性好的优点,其他活性氧物种及常见的离子和小分子不会对H2O2的检测造成影响,适合在复杂生物体系等领域中应用;
(3)本发明荧光检测体系中所使用的荧光探针为近红外探针,具有较强的组织穿透力,较小的组织伤害性,且不易受到生物体内背景荧光的干扰,成像效果好。
附图说明
【图1】本发明实施中荧光探针的荧光强度随H2O2浓度变化的荧光发射光谱图;
【图2】本发明实施中荧光探针的荧光强度与H2O2浓度的线性关系图;
【图3】本发明实施中荧光探针对H2O2的选择性图;
【图4】本发明实施中荧光探针在HeLa细胞内荧光共聚焦成像图。
具体实施方式
以下实施方式旨在进一步阐释说明本发明而不是对本发明的限定。
实施例1
将化合物1(372.51 mg,2mmol)和化合物2(654.07 mg,2.2mmol)溶于30mL乙醇中,向反应体系中加入1滴哌啶,加热回流,TLC监测至反应结束。反应完成后,将反应体系冷却至室温,减压浓缩后可获得红色固体492.54 mg,产率为52.9 %。1H NMR(400MHz, DMSO-d 6,ppm):δ=8.49-8.44 (m, 2H), 7.88-7.85 (m, 2H), 7.08 (d, J=7.6 Hz, 1H), 6.68 (d,J=16.0 Hz, 1H), 6.23 (s, 1H), 5.35 (s, 1H), 3.14 (t, J=7.48, 1H), 1.88 (s,4H), 1.56 (m, 2H), 1.31 (m, 2H), 0.99 (s, 6H), 0.90 (q, J=6.8 Hz, 3H)。
目标荧光分子探针的合成
将化合物3(465.54 mg,1mmol)和对溴甲基苯硼酸频哪醇酯(297.0 mg,1mmol)溶于5mLDMF中,加入K2CO3(150 mg,1.12mmol),加热回流至反应完全。取下反应,倒入水中,分别用水、饱和NaHCO3溶液及饱和食盐水萃取,合并有机层,用无水硫酸镁干燥后浓缩,经柱层析纯化后,得目标分子探针496.22 mg,产率 72.8 %。1H NMR(400MHz, DMSO-d 6, ppm):δ=8.45-8.50 (m, 2H), 7.94 (s, 1H), 7.82 (t, J=8.2 Hz, 1H), 7.68 (d, J=7.6 Hz,2H), 7.36 (d, J=7.6 Hz, 2H), 7.10 (d, J=7.6 Hz, 1H), 6.64 (d, J=16.0 Hz, 1H),6.25 (s, 1H), 5.16 (s, 2H), 3.24 (t, J=7.48, 1H), 1.87 (s, 4H), 1.58 (m, 2H),1.33 (m, 2H), 1.24 (s, 12H), 0.96 (s, 6H), 0.92 (q, J=6.8 Hz, 3H)。ESI-MS: m/zcalcd for [C42H43BN3O5]+, 680.33740; found, 680.4。
实施例2 荧光探针和H2O2溶液配制
探针溶液的制备:将上述分离得到的纯度在99 %以上的产物,准确称量并用PBS缓冲溶液调节至pH=7.4,且荧光探针的浓度为10μM。
H2O2溶液的配制:量取一定量的体积分数为30 %的H2O2溶液,用蒸馏水定容到50mL的容量瓶中,配成1×10-2 M的检测溶液,用PBS缓冲溶液稀释,配成浓度为1μM、2μM、3μM、5μM、10μM、15μM、25μM、35μM待用。
实施例3 荧光探针的荧光强度与H2O2的浓度的变化
取荧光探针溶液,分9组,分别加入H2O2待测溶液,使得每组探针溶液为10μM,而H2O2待测溶液浓度分别为0μM、1μM、2μM、3μM、5μM、10μM、15μM、25μM、35μM。在室温下孵育20min充分响应后,在10 mm的比色皿中测试不同体系的荧光光谱。荧光发射光谱变化图见附图1。结果表明,加入H2O2之前,由于苯硼酸酯基的淬灭作用,荧光探针在703nm处几乎没有荧光发射峰;加入H2O2之后,在近红外区(703nm)出现了近红外荧光发射峰,且随着H2O2浓度的增加,其荧光强度逐渐增强。图3为探针对不同H2O2浓度的线性响应图。从图中可知,当H2O2的浓度为0-5μM时,荧光强度与其浓度呈现线性关系,线性方程为y=17.55655x+3.62542,线性相关系数R2 = 0.99493,检测限是0.03μM。这说明该探针具有很高的灵敏度。
实施例4 荧光探针对H2O2测定的选择性
取荧光探针溶液,分10组,分别加入空白溶液、·OH、THBP、ClO-、ONOO-、NO2 -、Fe3+、Mg2+、Cys和H2O2待测溶液,使得检测体系中探针为10μM,H2O2待测溶液为25μM,而其他待测物溶液浓度50μM,在室温下孵育20 min充分响应后,在10 mm的比色皿中测试不同体系的荧光光谱,结果见图3。从图3中可以看出,只有H2O2能引起荧光光谱的明显增强,其他检测物对探针的荧光光谱没有明显的影响,荧光探针对H2O2有较好的选择性。
实施例5 荧光探针在活细胞中的应用
首先在HeLa培养基中加入探针溶液,置于培养箱中孵育30分钟,然后用 PBS缓冲液洗涤三次,除去未进入细胞的探针分子,移至荧光显微镜下成像,然后更换培养基,再用H2O2缓冲溶液(50μM)培养30分钟,用PBS缓冲溶液洗三次,置于荧光显微镜下观察其荧光变化,结果如图4所示。结果表明进入细胞体内的探针分子和H2O2发生了反应,呈现红色荧光,因此该荧光探针对细胞中的H2O2有良好的成像作用,可用于检测生物体内的H2O2。
上述虽然结合附图对本发明的具体实施方式进行了描述,但并非对发明范围的限制,本领域的相关技术人员能从发明公开的内容不需要付出创造性劳动即可做出的各种修改或变形仍在本发明的保护范围之内。
Claims (5)
3.取下反应,倒入水中,分别用水、饱和NaHCO3溶液及饱和食盐水萃取,合并有机层,用无水硫酸镁干燥后浓缩,经柱层析纯化后,可得目标分子探针。
4.根据权利要求1和2所述的近红外荧光检测试剂,其特征在于,其能不受 OH、THBP、ClO-、ONOO-、NO2 -、Fe3+、Mg2+、Cys的干扰。
5.权利要求1-3所述荧光检测试剂的用途,其特征在于,用于环境和生物样品等多个体系中过氧化氢的检测,实现体外诊断和分析。
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