CN109574910B - 一种咔唑衍生物mcab及其制备方法和应用 - Google Patents

一种咔唑衍生物mcab及其制备方法和应用 Download PDF

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CN109574910B
CN109574910B CN201811552686.XA CN201811552686A CN109574910B CN 109574910 B CN109574910 B CN 109574910B CN 201811552686 A CN201811552686 A CN 201811552686A CN 109574910 B CN109574910 B CN 109574910B
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王晓东
樊丽
葛金印
董川
双少敏
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Abstract

本发明公开了一种咔唑衍生物MCAB及其制备方法和应用。所述咔唑衍生物的中文名称为4‑(3‑(9‑(2‑(2‑甲氧基乙氧基)乙基‑9H‑咔唑‑3‑基)‑3‑丙烯酰基)苯甲醛，英文名称为，4‑(3‑(9‑(2‑(2‑methoxyethoxy)ethyl)‑9H‑carbazol‑3‑yl)‑3‑acryloyl)benzaldehyde，缩写为MCAB。其制备方法是：将1‑(9‑(2‑(2‑甲氧基乙氧基)乙基)‑9H‑咔唑‑3‑基)乙酮和对苯二甲醛溶于乙醇中，加入哌啶，加热回流制得粗品；将粗品除去溶剂，经硅胶柱分离得到纯品。将MCAB作为探针以α,β‑不饱和乙酰基咔唑衍生物为荧光团母体以及半胱氨酸(Cys)反应位点，利用巯基诱导α,β‑不饱和酮发生亲核加成反应，导致荧光增强，实现对Cys特异性检测，并且选择性好，与Cys的反应比与其他生物硫醇更有活性。利用激光共聚焦荧光成像技术能够高灵敏靶向检测溶酶体内Cys的变化，在生物分子检测领域具有广阔的应用前景。

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一种咔唑衍生物MCAB及其制备方法和应用
技术领域
本发明涉及硫醇分析技术领域，具体为一种咔唑衍生物MCAB及其制备方法，以及该衍生物MCAB在细胞内溶酶体半胱氨酸检测中的应用。
背景技术
半胱氨酸(Cys)作为人体必需的氨基酸和重要的生物硫醇，在调节人的生理机能方面具有重要的作用，如生物催化、蛋白质转录后的修饰和解毒过程等。体内Cys不足会导致儿童发育缓慢、肌无力、肝损伤以及肠粘膜萎缩等症状；同时，Cys浓度过高与心血管疾病和动脉粥硬化的疾病密切相关。因此，针对生物样品中半胱氨酸的高灵敏、实时检测的研究已成为相关领域的研究热点。溶酶体是细胞中一类非常重要的消化器官，其内含有磷酸酶、蛋白酶等50余种水解酶，可以将生物大分子或凋亡的细胞器水解成氨基酸，重新为细胞的生长提供能量。研究表明，组织蛋白酶作为溶酶体中一类典型的含有半胱氨酸的水解酶，对于维持溶酶体正常功能以及细胞内稳态发挥着关键作用。因此，发展高敏感、高选择性且溶酶体靶向的半胱氨酸检测方法对于理解溶酶体相关生理和病理过程具有重要的意义。
目前文献报道了许多基于半胱氨酸检测的荧光探针，然而由于生物硫醇在结构和生物活性上的相似性，能将半胱氨酸与高半胱氨酸(Hcy)和谷胱甘肽(GSH)进行区分检测的荧光探针十分有限，而且这类探针大多数不具有溶酶体靶向性。此外，现有溶酶体靶向基团集中于传统的吗啉环和二甲氨基结构，这类弱碱性基团容易聚集在弱酸性溶酶体中引起溶酶体的“碱化效应”，长时间作用会导致细胞中毒。因此，需要开发新型溶酶体靶向基团用于溶酶体内Cys的检测。本发明引入能够有效避免溶酶体的“碱化效应”的methylcarbitol为新型溶酶体靶向基团，利用具有优良荧光性质的α,β-不饱和乙酰基咔唑衍生物为荧光团母体结构以及Cys反应位点，设计合成了探针MCAB(4-(3-(9-(2-(2-methoxyethoxy)ethyl)-9H-carbazol-3-yl)-3-acryloyl)benzaldehyde)，实现了对细胞溶酶体半胱氨酸的特异性检测。
发明内容
本发明的目的之一是提供一种咔唑衍生物MCAB及其制备方法；目的之二是提供该衍生物的用途，即用于水环境中Cys的检测和制备动物细胞中溶酶体内Cys检测试剂。
本发明提供一种咔唑衍生物MCAB，其结构式为：
Figure BDA0001911039250000021
其合成路线为：
Figure BDA0001911039250000022
本发明提供的一种咔唑衍生物MCAB的制备方法，包括如下步骤：
(1)在三口烧瓶中，将1-(9-(2-(2-甲氧基乙氧基)乙基)-9H-咔唑-3-基)乙酮和对苯二甲醛按摩尔比1：1.5溶于乙醇中，加入催化量的哌啶，加热回流12h；体系冷却至室温，减压旋蒸除去溶剂制得粗品；
(2)粗品经硅胶柱提纯得到深绿色固体为目标化合物MCAB。
步骤(2)中所述的硅胶柱色谱的洗脱剂的体积配比为氯仿：乙醇＝20：1。
本发明提供的咔唑衍生物MCAB，可用于水环境Cys的检测和动物细胞中溶酶体内Cys的检测；所述的检测包括荧光检测和细胞成像检测。
与现有技术相比，本发明具有以下有益效果：(1)所述咔唑衍生物(MCAB)合成步骤简单，成本低廉，易于大规模生产，具有潜在的商品化应用价值；(2)所述衍生物以α,β-不饱和乙酰基咔唑化合物为荧光团母体结构，以及Cys反应位点；(3)利用巯基诱导α,β-不饱和酮发生亲核加成反应，导致荧光增强，实现对Cys特异性检测，并且其它氨基酸不干扰对Cys的检测。(4)该衍生物具有良好的细胞膜渗透能力，实现了对细胞溶酶体Cys的特异性成像与检测，在溶酶体Cys生理学和病理学研究中具有潜在的应用前景。(5)所述的检测手段简单，只需包括荧光分光光度计和激光共聚焦显微镜。
附图说明
图1.本发明MCAB的核磁表征，1H-NMR和13C NMR谱。
图2.本发明MCAB的质谱表征，LC-MS谱。
图3.本发明MCAB与Cys(100μM)反应随时间变化的紫外-可见吸收光谱图。
图4.本发明MCAB与Cys(100μM)反应随时间变化的荧光光谱图。
图5.本发明MCAB在紫外灯下识别Cys前后颜色变化，颜色由无色变为蓝色。
图6.本发明MCAB(25μM)与各种生物硫醇，常见氨基酸和其它各种常见离子(500μM)存在下，对Cys的选择性。
图7.本发明MCAB与市售绿色溶酶体探针(LysoTracker Green DND-26)在pH值7.4的条件下共同孵育30min的共定位荧光成像图。
图8.本发明MCAB在细胞中Cys经硫醇封阻剂N-乙基马来酰亚胺(NEM)处理前后的荧光成像图。
具体实施方式
实施例1
1，4-(3-(9-(2-(2-甲氧基乙氧基)乙基-9H-咔唑-3-基)-3-丙烯酰基)苯甲醛(MCAB)的制备及表征：
Figure BDA0001911039250000031
在三口烧瓶中，将1-(9-(2-(2-甲氧基乙氧基)乙基)-9H-咔唑-3-基)乙酮(70mg，0.22mmol)和对苯二甲醛(45mg，0.33mmol)溶于乙醇中，加入3-5滴哌啶，加热回流12h至反应完全；体系冷却至室温，减压旋蒸除去溶剂制得粗品；粗品经硅胶柱提纯(洗脱剂按体积比氯仿：甲醇＝20：1)得到深绿色固体为目标化合物MCAB(探针)。
1H NMR(600MHz，CDCl3，图1中上图)δ(ppm):3.30(3H),3.43(2H),3.56(2H),3.96(2H),4.60(2H),7.40-7.43(1H),7.59-7.62(2H),7.85-8.00(9H),8.24-8.28(1H),8.93(1H).
13C NMR(150MHz,CDCl3，图1中下图)δ(ppm)：191.53,188.71,144.45,142.27,140.87,137.23,128.91,124.84,123.23,122.24,109.84,71.99,70.96,69.38,59.10,29.71.
HR-MS m/z(图2)：[M+H]+calclated for C27H25NO4 +,428.1856；measured,428.1855.
实施例2
用DMSO/PBS缓冲液(pH 7.4)体系(v/v＝1/1)将探针MCAB稀释到25μM，记录MCAB与Cys(500μM)反应随时间变化的紫外吸收光谱。如图3所示，加入Cys后，300nm和388nm的紫外吸光度变化至255nm和338nm。
实施例3
用DMSO/PBS缓冲液(pH 7.4)体系(v/v＝1/1)将探针MCAB稀释到25μM，记录MCAB与Cys(500μM)反应随时间变化的荧光光谱，固定激发波长为370nm，激发和发射狭缝宽带均为2.0nm。加入Cys后，440nm出现新的发射峰且随着时间延长依次增强。该反应在12min时荧光强度到最大值(图4)。在紫外灯照射下，溶液的颜色由无色变为蓝色(图5)。
实施例4
考察实施例1中的探针(25μM)在各种生物硫醇(500μM)，常见氨基酸和其它各种常见离子(500μM)存在下，对Cys的选择性。由图6可知，探针与Cys反应后荧光强度显著增强，而与Hcy和GSH反应的荧光呈现较弱的变化，说明探针探针与Cys的反应比与其他生物硫醇更有活性。同时，其他物质未对Cys的检测形成明显干扰。该结果证明，本发明探针能够应用于细胞内Cys的选择性检测而不受其他物质的干扰。图6中各物质的顺序依次为：(1)blank；(2)Cys；(3)Hcy；(4)GSH；(5)Try；(6)Glu；(7)Asn；(8)His；(9)Arg；(10)Pro；(11)Phe；(12)Leu；,(13)Gln；(14)Ser；(15)Val；(16)Met；(17)Ile；(18)Asp；(19)Thr；(20)Tyr；(21)Ala；(22)Iso；(23)Lys；(24)Gly；(25)S2-；(26)SO3 2-；(27)SO4 2-；(28)HSO3 -；(29)K+；(30)Na+；(31)Ca2+；(32)Mg2+；(33)Al3+；(34)Zn2+；(35)Cu2+；(36)Fe3+；(37)Fe2+；(38)Cl-；(39)Br-；(40)CO3 2-；(41)AcO-；(42)NO3 -；(43)NO2 -。
实施例5
将实施例1中的探针、市售绿色溶酶体探针(LysoTracker Green DND-26)与SMMC7721细胞在pH值7.4条件于37℃、5％CO2的孵育箱中共同孵育30min，在共聚焦显微镜下观察荧光成像。探针固定激发波长为405nm，发射波段收集蓝色通道(410-500nm)；市售绿色溶酶体探针固定激发波长为488nm，发射波段收集绿色通道(510–550nm)。如图7所示，探针MCAB的蓝色荧光(图7a)和LysoTracker Green DND-26的绿色荧光(图7b)能够很好的重叠(图7c)。此外，二者在细胞内的荧光光谱变化趋向一致(图7e)，且共定位率高达0.90(图7f)，说明探针能有效地靶向溶酶体。
实施例6
将实施例1中的探针与SMMC 7721细胞在pH值7.4条件于37℃、5％CO2的孵育箱中孵育10min，固定激发波长为405nm，发射波段收集蓝色通道(410-500nm)。在共聚焦显微镜下探针观察到蓝色荧光(图8a)，这是由于细胞中存在内源性的Cys。其次，将细胞用N-乙基马来酰亚胺(NEM，500μM)预处理(硫醇封阻剂，能够屏蔽细胞内硫醇类物质)40min，然后与探针(10μM)共孵育30min，发现蓝色荧光淬灭(图8b)表明硫醇类物质被NEM完全屏蔽。随后，将NEM预处理过的SMMC 7721细胞分别与Cys，Hcy和GSH(100μM)孵育20min，然后加入探针(10μM)继续孵育10min，可观察到加了Cys的细胞蓝色荧光明显增强(图8c)，而经Hcy和GSH处理的细胞未见荧光明显变化(图8d,e)。该结果证实探针能够实现对活细胞溶酶体内Cys的高灵敏和高选择性检测。

Claims (6)

1.一种咔唑衍生物MCAB，其特征在于，结构式为：
Figure FDA0001911039240000011
2.如权利要求1所述的一种咔唑衍生物MCAB的制备方法，其特征在于，包括如下步骤：
(1)将1-(9-(2-(2-甲氧基乙氧基)乙基)-9H-咔唑-3-基)乙酮和对苯二甲醛溶于少量乙醇中，加入催化量的哌啶，加热回流反应12h；体系冷却至室温，减压旋蒸除去溶剂制得粗品；
(2)粗品经硅胶柱色谱提纯得到深绿色固体为目标化合物MCAB。
3.如权利要求2所述的咔唑衍生物MCAB的制备方法，其特征在于步骤(1)中所述的1-(9-(2-(2-甲氧基乙氧基)乙基)-9H-咔唑-3-基)乙酮和对苯二甲醛的摩尔比为1：1.5。
4.如权利要求2所述的咔唑衍生物对苯二甲醛的制备方法，其特征在于步骤(2)中所述的硅胶柱色谱的洗脱剂的体积配比为氯仿：乙醇＝20：1。
5.如权利要求1所述的咔唑衍生物MCAB在水环境中Cys检测中的应用。
6.如权利要求1所述的咔唑衍生物MCAB在制备动物细胞溶酶体Cys检测试剂中的应用。
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WO2022020244A1 (en) * 2020-07-20 2022-01-27 Annexon, Inc. Inhibitors of complement factors and uses thereof
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CN112724069A (zh) * 2021-01-28 2021-04-30 内蒙古农业大学 一种用于识别检测铁汞的咔唑基乙酮荧光探针化合物

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106833625A (zh) * 2017-03-14 2017-06-13 山西大学 一种双光子溶酶体pH荧光探针及其制备方法和应用
CN106987246A (zh) * 2017-03-31 2017-07-28 安徽大学 一种双光子荧光染料及其制备方法和用途

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106833625A (zh) * 2017-03-14 2017-06-13 山西大学 一种双光子溶酶体pH荧光探针及其制备方法和应用
CN106987246A (zh) * 2017-03-31 2017-07-28 安徽大学 一种双光子荧光染料及其制备方法和用途

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
A novel "turn-on" fluorescent probe with a large stokes shift forhomocysteine and cysteine: Performance in living cells and zebrafish;Haohan Song et al.,;《Sensors and Actuators B》;20171205;第259卷;第234页Scheme 1，第238页表1，第238页表1， *
Synthesis and spectrum characteristic of four new organic fluorescent dyes of pyrazoline compounds;Guan Bai et al.,;《Dyes and Pigments》;20060711;第75卷;第94页Scheme 4和第96页右栏第2段 *

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