CN110894194A - 一种检测过氧化氢的新型荧光探针的合成 - Google Patents
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Abstract
一种检测过氧化氢的新型荧光探针，其化学结构式如下。经实验证明，该探针对过氧化氢具有较好的选择性。本发明公开了探针的合成方法。
Description
技术领域
本发明属于生物化学技术领域，具体涉及一种可检测过氧化氢新型荧光探针的制备方法。
背景技术
过氧化氢是生物体内必不可少的活性氧成分，在生理和病理过程中发挥着重要的生物功能。近些年来，随着对过氧化氢研究的深入，科学工作者们发现其可以作为第二信使调节基本的生命活动，如创伤的修复、干细胞增生等。而异常水平的过氧化氢的存在，对生物体会造成严重的毒害作用，如氧化应激伤害，从而导致病变器官的衰竭；另外还有恶性肿瘤、心血管机能紊乱等。因此，能够准确的检测机体内过氧化氢含量对于临床疾病的预防、诊断和检测具有重要的意义。
小分子荧光作为近年来研究的热点，已逐渐发展成为检测生物化学物质的一种重要技术手段。其凭借高选择性、高灵敏度、操作简便等特点，可在生物体内外准确检测待测物的含量，并通过荧光光谱仪或荧光共聚焦显微镜等实现肉眼的可视化监测。
本发明设计、合成了一种可检测过氧化氢的小分子荧光探针，并公布其制备方法。
发明内容
本发明涉及一种可检测过氧化氢新型荧光探针的制备方法。
本发明的技术方案如下：
一种新型的荧光探针，中文名：6-吗啉-2，3-二氢-1-氧杂蒽-4-甲基肟。具体化学结构如下：
该新型荧光探针的合成方法，其特征由如下步骤组成：
步骤1称取适量化合物A倒入容积一定的反应器，并溶解在一定体积一定温度的特定溶剂中，加入适量三溴化磷并在特定的反应温度下反应，直至原料完全消耗，处理获得化合物B。
步骤2称取适量化合物B、C，倒入含有一定溶剂的容器中，置于某温度下，加入特定量的碳酸铯，反应直至原料消耗完全，处理获得化合物D。
步骤3称取适量化合物D倒入容积一定的反应器，并溶解在一定体积的溶剂中，加入适量吗啉，碳酸铯，醋酸钯和BINAP，在特定的温度下反应直至原料消耗完全，处理获得化合物F。
步骤4称取适量化合物F，盐酸羟胺加入某容器中，溶解在少许溶剂中，反应直至原料消耗完全，处理获得化合物G，即探针。
本发明涉及合成的一种可检测过氧化氢的新型荧光探针，具有较好的选择性。
具体实施方式
通过以下实例具体解释本发明，但本发明的保护范围并不受任何实施实例的限制。
实施实例一：荧光探针的制备方法
步骤1 在0℃条件下，向DMF(12mL，155mM)和CHCl3中加入PBr3(9mL，94.7mM)，反应1h。称量化合物A(4mL，94.7mmol)溶解在10mL CHCl3后，缓慢加入上述溶液中，在25℃条件下反应18h。TLC检测反应，直至原料完全消耗。将红色的溶液倒入冰水中，加入固体碳酸氢钠调至中性，二氯甲烷溶剂萃取三次，旋转蒸发仪浓缩反应液，获得粗产品，最终获得化合物B。
步骤2 称取化合物B 389mg，化合物C733mg倒入50mL圆底烧瓶中，并溶解于5mLDMF中。加入碳酸铯1.91g，置于室温，反应48h，TLC检测反应，直至原料消耗完全。将反应液倒入盐水中，乙酸乙酯萃取三次，旋转蒸发仪浓缩反应液，获得粗产物。通过200-300目硅胶柱层析纯化，最终获得化合物D。
步骤3 称取化合物D 200mg，吗啉82.3mg，碳酸铯291mg，醋酸钯1.88mg和BINAP12.8mg，溶入5mL甲苯中，130℃条件下加热回流24h，TLC检测反应，直至原料完全消耗。将反应液倒入盐水中，乙酸乙酯萃取三次，旋转蒸发仪浓缩反应液，获得粗产品，最终获得化合物F。
步骤4 称取化合物F 100mg，盐酸羟胺35.1mg，醋酸钠54.5mg溶于4mL甲醇60℃加热回流12h，TLC检测反应，直至原料完全消耗。通过200-300目硅胶柱纯化，最终获得化合物G，即荧光探针。1H NMR(400MHz，DMSO-d6)δ10.78(s，1H)，8.31(s，1H)，6.99(d，J＝8.4Hz，1H)，6.66-6.53(m，2H)，6.39(s，1H)，3.75-3.67(m，4H)，3.19-3.11(m，4H)，2.42(dt，J＝21.0，5.8Hz，4H)，1.69-1.59(m，2H).
Claims (2)
1.一种检测过氧化氢的新型荧光探针，中文名：6-吗啉-2，3-二氢-1-氧杂蒽-4-甲基肟，其特征为化学结构如下：
2.权利要求1中所述一种检测过氧化氢的新型荧光探针的制备方法，其特征是由如下步骤组成：
步骤1 在0℃条件下，向DMF(12mL，155mM)和CHCl3中加入PBr3(9mL，94.7mM)，反应1h。称量化合物A(4mL，94.7mmol)溶解在10mL CHCl3后，缓慢加入上述溶液中，在25℃条件下反应18h。TLC检测反应，直至原料完全消耗。将红色的溶液倒入冰水中，加入固体碳酸氢钠调至中性，二氯甲烷溶剂萃取三次，旋转蒸发仪浓缩反应液，获得粗产品，最终获得化合物B。
步骤2 称取化合物B 389mg，化合物C733mg倒入50mL圆底烧瓶中，并溶解于5mL DMF中。加入碳酸铯1.91g，置于室温，反应48h，TLC检测反应，直至原料消耗完全。将反应液倒入盐水中，乙酸乙酯萃取三次，旋转蒸发仪浓缩反应液，获得粗产物。通过200-300目硅胶柱层析纯化，最终获得化合物D。
步骤3 称取化合物D 200mg，吗啉82.3mg，碳酸铯291mg，醋酸钯1.88mg和BINAP12.8mg，溶入5mL甲苯中，130℃条件下加热回流24h，TLC检测反应，直至原料完全消耗。将反应液倒入盐水中，乙酸乙酯萃取三次，旋转蒸发仪浓缩反应液，获得粗产品，最终获得化合物F。
步骤4 称取化合物F 100mg，盐酸羟胺35.1mg，醋酸钠54.5mg溶于4mL甲醇60℃加热回流12h，TLC检测反应，直至原料完全消耗。通过200-300目硅胶柱纯化，最终获得化合物G，即荧光探针。
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| CN106967102A (zh) * | 2017-03-20 | 2017-07-21 | 济南大学 | 一种基于罗丹明衍生物的过氧化氢增强型荧光探针 |
| CN108299485A (zh) * | 2018-02-09 | 2018-07-20 | 湖北大学 | 一种用于检测活细胞内过氧化氢的荧光探针及其制备方法和应用 |
| CN108285789A (zh) * | 2018-04-20 | 2018-07-17 | 济南大学 | 一种过氧化氢荧光探针及其制备方法和应用 |
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