CN107973787B - 一种香豆素衍生物dmac及其制备方法和应用 - Google Patents

一种香豆素衍生物dmac及其制备方法和应用 Download PDF

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CN107973787B
CN107973787B CN201711222099.XA CN201711222099A CN107973787B CN 107973787 B CN107973787 B CN 107973787B CN 201711222099 A CN201711222099 A CN 201711222099A CN 107973787 B CN107973787 B CN 107973787B
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dmac
coumarin derivative
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diethylamino
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阴彩霞
岳永康
霍方俊
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Shanxi University
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Abstract

本发明提供了一种香豆素衍生物DMAC及其制备方法和应用，所述香豆素衍生物，中文名称为(E)‑7‑(二乙氨基)‑3‑(3‑(4‑(4‑(吗啉代甲基)‑1H‑1,2,3‑三唑‑1‑基)苯基)丙烯酰基)‑2H‑苯并吡喃‑2‑酮，英文名称为(E)‑7‑(diethylamino)‑3‑(3‑(4‑(4‑(morpholinomethyl)‑1H‑1,2,3‑triazol‑1‑yl)phenyl)acryloyl)‑2H‑chr omen‑2‑one，缩写为DMAC。本发明提供了一种对半胱氨酸特异性检测的方法，是基于香豆素衍生物DMAC，在PB/DMSO(v/v,9:1,pH 5.0)溶液中检测半胱氨酸。本发明DMAC可通过荧光成像技术检测细胞溶酶体中的半胱氨酸，在生物分子检测领域具有广阔的应用前景。

Description

一种香豆素衍生物DMAC及其制备方法和应用
技术领域
本发明涉及分析化学技术领域，具体属于一种香豆素衍生物DMAC及其制备方法，以及该衍生物DMAC在细胞溶酶体半胱氨酸检测中的应用。
背景技术
半胱氨酸(Cys)作为生物体内的硫源，它负责着细胞内主要还原性物质之一的谷胱甘肽、神经递质牛磺酸、气体信号分子硫化氢及各种蛋白质的合成，扮演着氧化还原调节、生物催化等一系列重要的角色。研究表明，饮食半胱氨酸含量缺乏将导致肠粘膜萎缩，引起儿童生长缓慢等疾病。同时，血浆中总半胱氨酸和总同型半胱氨酸水平的升高与动脉粥样硬化等心脑血管疾病密切相关。
细胞内溶酶体是细胞的消化器，其中包含蛋白酶、核酸酶、磷酸酶等60余种水解酶调控多种内源性和外源性大分子物质的消化，维持细胞内稳态。近年来，随着细胞代谢过程的研究深入，溶酶体功能得到进一步认识，其在细胞凋亡和细胞死亡中的调控作用日益受到关注。组织蛋白酶是溶酶体中典型的一类含有半胱氨酸的水解酶，其在溶酶体功能的维持中举足轻重。因此，对溶酶体中半胱氨酸的检测对溶酶体相关生理过程和病理过程研究具有重要的意义。
本发明提供了一种香豆素衍生物DMAC及其制备方法，并基于该衍生物DMAC实现了对细胞溶酶体半胱氨酸的特异性检测。
发明内容
本发明的目的在于提供一种香豆素衍生物及其制备方法，以及该衍生物可作为检测试剂用于Cys的荧光检测；在检测Cys时选择性高，灵敏度高；该衍生物可用于细胞溶酶体内Cys的检测。
本发明提供的一种香豆素衍生物，中文名称为(E)-7-(二乙氨基)-3-(3-(4-(4-(吗啉代甲基)-1H-1,2,3-三唑-1-基)苯基)丙烯酰基)-2H-苯并吡喃-2-酮，英文名称为(E)-7-(diethylamino)-3-(3-(4-(4-(morpholinomethyl)-1H-1,2,3-triazol-1-yl)phenyl)acryloyl)-2H-chr omen-2-one，缩写为DMAC。结构式为：
Figure BDA0001486565900000021
香豆素衍生物在PB/DMSO(v/v,9:1,pH 5.0)溶液中对Cys显示了优良的灵敏性和选择性，检测过程简便、灵敏。
DMAC的制备：
1)将3-乙酰基-7-N,N-二乙胺基香豆素、对叠氮基苯甲醛按摩尔比为1：1.2溶于乙醇中，加入催化量的哌啶，回流70h至反应完全；体系减压蒸干溶剂得到粗产品，然后柱色谱分离(洗脱剂按体积比乙酸乙酯：二氯甲烷＝3：125)得到(E)-3-(3-(4-叠氮基苯基)丙烯酰基)-7-(二乙基氨基)-2H-苯并吡喃-2-酮；
2)将步骤1)所得(E)-3-(3-(4-叠氮基苯基)丙烯酰基)-7-(二乙基氨基)-2H-苯并吡喃-2-酮、炔丙基吗啉、三乙胺按摩尔比为1：1：0.5溶于四氢呋喃中，氩气保护下逐渐加入CuI(0.2当量)，室温搅拌6h至反应完全；体系减压蒸干后柱色谱分离(洗脱剂按体积比甲醇：二氯甲烷＝1：20)得到目标化合物DMAC。
本发明香豆素衍生物DMAC的用途：该衍生物可以在pH 5.0体系中对水环境和细胞溶酶体中半胱氨酸特异性检测；所述的检测包含荧光检测和细胞成像检测。
与现有技术相比，本发明具有如下有益效果：
1、所述香豆素衍生物合成简单，成本低廉，易于大规模生产；
2、所述检测方法能够实现Cys的特异性检测，其它氨基酸不干扰对Cys的测定；
3、所述检测方法首次实现了细胞溶酶体内Cys特异性成像，其在溶酶体Cys生理学和病理学研究中具有广阔的应用前景；
4、检测手段简单，只需要借助荧光分光光度仪和激光共聚焦显微镜即可实现。
附图说明：
图1a DMAC氢谱表征。
图1b DMAC碳谱表征。
图1c DMAC质谱表征。
图2实施例2DMAC与Cys作用的随时间荧光发射图。
图3实施例3DMAC与各种分析物作用的荧光发射图。其中1.空白；2.Trp；3.Thr；4.Ser；5.Leu；6.Ile；7.His；8.Gly；9.Gln；10.Asn；11.Ala；12.Pro；13.Asp；14.Met；15.Arg；16.Tyr；17.Lys；18.Glu；19.Val；20.Phe；21.Hcy；22.GSH；23.Cys。
图4实施例4DMAC对细胞内源Cys进行特异性成像图。其中a-e：绿色通道成像；f-j：绿色通道与明场叠加。
图5实施例5DMAC对细胞内源Cys成像图与商业化染溶酶体红的共定位成像图。其中a)绿色通道成像；b)红色通道成像；c)明场；d)三通道叠加；e)关注区域放大；f)关注区域绿色通道和红色通道相关图。
具体实施方式：
下面结合实施例和附图对本发明做进一步说明，但本发明不受下述实施例的限制。
实施例1
DMAC的制备及表征：
将3-乙酰基-7-N,N-二乙胺基香豆素(2mmol,0.52g)、对叠氮基苯甲醛(2.4mmol,0.35g)溶于乙醇中，加入3～5滴哌啶，回流70h至反应完全；体系减压蒸干溶剂得到粗产品，然后柱色谱分离(洗脱剂按体积比乙酸乙酯：二氯甲烷＝3：125)得到(E)-3-(3-(4-叠氮基苯基)丙烯酰基)-7-(二乙基氨基)-2H-苯并吡喃-2-酮。
取(E)-3-(3-(4-叠氮基苯基)丙烯酰基)-7-(二乙基氨基)-2H-苯并吡喃-2-酮(0.5mmol,0.19g)、炔丙基吗啉(0.5mmol,0.07g)、三乙胺(0.25mmol,0.03g)溶于四氢呋喃中，氩气保护下逐渐加入CuI(0.2mmol,0.04g)，室温搅拌6h至反应完全；体系减压蒸干后柱色谱分离(洗脱剂按体积比甲醇：二氯甲烷＝1：20)得到目标化合物DMAC。
1H NMR(600MHz,CDCl3)δ8.57(s,1H),8.21(d,J＝15.7Hz,1H),8.00(s,1H),7.86–7.75(m,5H),7.44(d,J＝8.9Hz,1H),6.64(d,J＝9.5Hz,1H),6.50(s,1H),3.78(s,2H),3.77–3.72(m,4H),3.48(q,J＝7.1Hz,4H),2.60(s,4H),1.26(t,J＝7.1Hz,6H)(图1a)。13CNMR(151MHz,CDCl3)δ186.2,161.0,158.8,153.2,149.0,141.1,137.7,135.9,131.9,130.0,126.3,120.4,116.3,110.0,108.7,96.6,66.8,53.6,53.4,45.2,12.5(图1b)。HR MS[M+H]+:m/z Calcd 514.2449,Found 514.2449(图1c)。
实施例2
配制pH＝5.0的PB缓冲溶液，配制2mMDMAC的DMSO溶液，配制20mM Cys的水溶液；取2mL的PB/DMSO(v/v,9:1,pH 5.0)溶液、20μL DMAC的DMSO溶液加到一个荧光比色皿中，加入120μL Cys的水溶液，随时间在荧光分光光度仪上检测(430nm激发)。0-60min内，498nm的荧光强度逐渐增强，荧光发射图见图2。
实施例3
配制pH＝5.0的PB缓冲溶液，配制2mMDMAC的DMSO溶液，分别配制20mMCys，Hcy，Ala，Asn，Arg，Asp，Gln，Glu，Gly，His，Ile，Leu，Lys，Met，Phe，Pro，Ser，Thr，Trp，Tyr，Val和200mM GSH，的水溶液；在23个荧光比色皿中，各加入2mL的PB/DMSO(v/v,9:1,pH 5.0)溶液、20μL DMAC的DMSO溶液，再分别加入120μL的水，Cys，Hcy，Ala，Asn，Arg，Asp，Gln，Glu，Gly，His，Ile，Leu，Lys，Met，Phe，Pro，Ser，Thr，Trp，Tyr，Val和GSH。1h后在荧光分光光度仪上检测(430nm激发)，(见图3)。Cys使得检测体系在498nm处荧光强度明显升高，其它的分析物没有引起检测体系荧光强度的变化。
经实验证明，其它分析物不干扰体系对Cys的检测。
实施例4
配置4mMDMAC的DMSO溶液，分别配制20mM Cys、Hcy和GSH的水溶液，配制200mMN-乙基马来酰亚胺(NEM)的DMSO溶液；对五个育有A549细胞的培养皿进行编号，1号用含有终浓度为5μMDMAC的PBS孵育10min后用激光共聚焦显微镜成像；2-5号用含有终浓度为1mMNEM的PBS孵育30min，分别加入PBS、Hcy(终浓度为15μM)、GSH(终浓度为1mM)、Cys(终浓度为200μM)孵育30min，洗涤后继续用含有终浓度为5μM DMAC的PBS孵育10min后用激光共聚焦显微镜成像(见图4)。用405nm进行激发，在绿色通道中(470-520nm)可以看到1号和5号细胞中有强的荧光发射，2、3和4号细胞无荧光发射。此实验证明DMAC可以在细胞水平对Cys进行特异性检测。
实施例5
配置4mMDMAC的DMSO溶液，配制0.5μM商业化的溶酶体红色染料-溶酶体红的PBS溶液；取育有A549细胞的培养皿依次孵育终浓度为5μM DMAC的PBS(10min)、终浓度为0.5μM的商业化溶酶体红色染料-溶酶体红的PBS(15min)后用激光共聚焦显微镜成像(见图5)。分别用405nm和461nm作为绿色通道(470-520nm)和红色通道(580-600nm)的激发光，绿色通道和红色通道均有强的荧光发射。利用软件得到绿色通道和红色通道荧光发光位置重叠。此实验证明DMAC可以检测溶酶体中的Cys。

Claims (8)

1.一种香豆素衍生物DMAC，其特征在于，结构式为：
Figure DEST_PATH_IMAGE002A
。
2.如权利要求1所述的一种香豆素衍生物DMAC的制备方法，其特征在于，包括如下步骤：
1）将3-乙酰基-7-N,N-二乙胺基香豆素、对叠氮基苯甲醛溶于乙醇中，加入催化量的哌啶，回流至反应完全；体系减压蒸干溶剂得到粗产品，然后柱色谱分离得到（E）-3-（3-（4-叠氮基苯基）丙烯酰基）-7-（二乙基氨基）-2H-苯并吡喃-2-酮；
2）将步骤1）所得（E）-3-（3-（4-叠氮基苯基）丙烯酰基）-7-（二乙基氨基）-2H-苯并吡喃-2-酮、炔丙基吗啉、三乙胺溶于四氢呋喃中，氩气保护下逐渐加入CuI，室温搅拌至反应完全；体系减压蒸干后柱色谱分离得到目标化合物DMAC。
3.如权利要求2所述的香豆素衍生物DMAC的制备方法，其特征在于，所述步骤1）中3-乙酰基-7-N,N-二乙胺基香豆素和对叠氮基苯甲醛的摩尔比为1：1.2。
4.如权利要求2所述的香豆素衍生物DMAC的制备方法，其特征在于，所述步骤1）中柱色谱的洗脱剂体积配比为乙酸乙酯：二氯甲烷=3：125。
5.如权利要求2所述的香豆素衍生物DMAC的制备方法，其特征在于，所述步骤2）中（E）-3-（3-（4-叠氮基苯基）丙烯酰基）-7-（二乙基氨基）-2H-苯并吡喃-2-酮、炔丙基吗啉、三乙胺和CuI的摩尔比为1：1：0.5：0.2。
6.如权利要求2所述的香豆素衍生物DMAC的制备方法，其特征在于，所述步骤2）中柱色谱的洗脱剂体积配比为甲醇：二氯甲烷=1：20。
7.如权利要求1所述的香豆素衍生物DMAC在非疾病诊断或治疗目的的非有生命的人体/动物体的pH 5.0的水环境中半胱氨酸检测中的应用。
8.如权利要求1所述的香豆素衍生物DMAC在制备动物细胞溶酶体半胱氨酸检测试剂中的应用。
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