CN108383774B - 一种基于端基炔酮的半胱氨酸荧光探针及其制备和应用 - Google Patents
一种基于端基炔酮的半胱氨酸荧光探针及其制备和应用 Download PDFInfo
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Abstract
Description
技术领域
本发明属于半胱氨酸荧光探针制备领域,具体涉及一种基于端基炔酮的半胱氨酸荧光探针及其制备和应用。
背景技术
生物硫醇(半胱氨酸、同型半胱氨酸和谷胱甘肽)在生理学和病理学过程中扮演着重要的角色。半胱氨酸和同型半胱氨酸在人体内的正常水平分别为30-200μm和9-15 μm,而细胞内谷胱甘肽的浓度高达1-10 mM。这使得开发能够选择性识别Cys和Hcy且不受GSH干扰的荧光探针成为难点。
目前报道的基于芳香亲核取代、迈克尔加成-分子内环化级联等反应类型的探针,在与Cys、Hcy和GSH反应后可得到不同的荧光信号,实现了这三种硫醇之间的区分,但由于GSH可与探针反应,从而导致探针的消耗。因此,开发易合成、选择性好,且能避免细胞内大量GSH干扰和消耗,实现Cys特异性检测的荧光探针尤为重要。
发明内容
本发明提出了一种基于端基炔酮的半胱氨酸荧光探针及其制备和应用,分别以咔唑衍生物和香豆素衍生物为荧光团,端基炔酮为反应位点,构建两个荧光探针(Ⅰ)和(Ⅱ)。探针与谷胱甘肽发生迈克尔加成后的产物能继续与半胱氨酸发生亲核取代反应,从而避免细胞内大量存在的谷胱甘肽对探针识别半胱氨酸的干扰。
实现本发明的技术方案是:一种基于端基炔酮的半胱氨酸荧光探针,结构式如(Ⅰ)或(Ⅱ)所示:
所述的基于端基炔酮的半胱氨酸荧光探针的制备方法,步骤如下:
将N-乙基咔唑-3-甲醛或7-(二乙氨基)香豆素-3-甲醛在0 ℃,N2保护下溶解于四氢呋喃中,滴加乙炔基溴化镁反应2-3 h,加入饱和氯化铵溶液进行淬灭反应,用乙酸乙酯和水萃取反应体系,并减压蒸除有机溶剂,得到的粗品用二氯甲烷溶解后,滴加至MnO2的二氯甲烷悬浮液中,0 ℃搅拌2-6 h,分离纯化分别得到结构式为(Ⅰ)或(Ⅱ)的荧光探针。
所述N-乙基咔唑-3-甲醛或7-(二乙氨基)香豆素-3-甲醛与乙炔基溴化镁的物质的量比为1:(1-2)。
所述的荧光探针在检测活细胞中半胱氨酸的应用。
所述活细胞为Hela细胞。
本发明用于检测半胱氨酸的荧光探针,包括检测水环境和生物样品中的半胱氨酸。
上述应用具体包括一下:
分别测试探针储存液加入半胱氨酸前后的紫外可见光谱和荧光光谱的变化,荧光的激发波长为340 nm(探针Ⅰ);观察荧光探针孵育的细胞及其加入半胱氨酸前后荧光成像图的变化。
荧光光谱的变化为:以340 nm光激发时,在465 nm处的荧光迅速增强,约2 min达到最高值后,逐渐红移并伴随490 nm处的荧光增强。
(探针Ⅰ)荧光成像图的变化为:用探针母液孵育细胞,并用共聚焦显微镜,以激发波长为405 nm光源激发,成像细胞中内源性的半胱氨酸;用N-乙基马来酰亚胺屏蔽细胞内源性的半胱氨酸后,进行共聚焦成像;用外源性的半胱氨酸孵育细胞,再用探针母液孵育,并用共聚焦显微镜成像。
本发明的有益效果是:(1)咔唑作为双光子染料,具有光稳定性好、量子产率高等优点,香豆素类衍生物具有大的斯托克斯位移、光学性质易调控等,通过有机化学的方法可对咔唑和香豆素衍生物进行修饰;(2)即使在毫摩尔级的谷胱甘肽的存在下,探针(Ⅰ)和(Ⅱ)与半胱氨酸也能很好的反应,本发明能避免体内大量存在的谷胱甘肽对检测的干扰;(3)本发明中的探针合成简单,产率高,能快速检测水溶液和细胞中的半胱氨酸,选择性好、灵敏度高、探针(Ⅰ)最低检测限为14 nM。这为避免细胞内大量谷胱甘肽干扰的前提下来研究半胱氨酸的生理作用提供了一种有效方法。
附图说明
为了更清楚地说明本发明实施例或现有技术中的技术方案,下面将对实施例或现有技术描述中所需要使用的附图作简单地介绍,显而易见地,下面描述中的附图仅仅是本发明的一些实施例,对于本领域普通技术人员来讲,在不付出创造性劳动的前提下,还可以根据这些附图获得其他的附图。
图1是实施例1探针(Ⅰ)的1H NMR图谱。
图2是实施例1探针(Ⅰ)的13C NMR图谱。
图3是在PBS缓冲(10 mM,pH = 7.4,含有10 %的DMSO)体系中,10 µM探针(Ⅰ)与200µM半胱氨酸反应时,荧光光谱随时间的变化图。
图4是在PBS缓冲(10 mM,pH = 7.4,含有10 %的DMSO)体系中,10 µM探针(Ⅰ)与不同浓度半胱氨酸(0-60 µM)反应的荧光光谱图。
图5是在PBS缓冲(10 mM,pH = 7.4,含有10 %的DMSO)体系中,10 µM探针(Ⅰ)与浓度范围在0-20 µM的半胱氨酸反应时,在464 nm处的荧光强度与Cys浓度的线性关系图。
图6是在PBS缓冲(10 mM,pH = 7.4,含有10 %的DMSO)体系中,10 µM探针(Ⅰ)及其加入不同的氨基酸(200 µM)反应5 min时于464 nm处的荧光发射光谱图。
图7是探针(Ⅰ)识别半胱氨酸的细胞实验研究图。图中的a组和d组,是加入探针孵育20 min后,分别为暗场和明场的细胞成像图。b组e组是先将细胞2 mM的N-乙基马来酰亚胺孵育20 min,再加入10 µM探针孵育20 min后,进行细胞暗场和明场成像。c组和f组是先用外源性半胱氨酸孵育20 min后,再孵育探针20 min后的细胞成像图。选用405 nm激发波长,收集430-550 nm的波长,标尺为50微米。
具体实施方式
下面将结合本发明实施例,对本发明的技术方案进行清楚、完整地描述,显然,所描述的实施例仅仅是本发明一部分实施例,而不是全部的实施例。基于本发明中的实施例,本领域普通技术人员在没有付出创造性劳动前提下所获得的所有其他实施例,都属于本发明保护的范围。
实施例1
探针(Ⅰ)的合成
向25 mL反应瓶中加入N-乙基咔唑-3-甲醛(446.5 mg,2 mmol),在0 ℃,N2保护下,加入5 mL的超干溶剂四氢呋喃(THF),并滴加入乙炔基溴化镁(6 mL,3 mmol,0.5 M溶于THF),2 h反应完全。加入10 mL的饱和氯化铵溶液淬灭反应,用乙酸乙酯萃取(3×10 mL),并干燥,减压蒸除有机溶剂,得到的粗品用4 mL二氯甲烷溶解,分批(2×2 mL)逐滴滴加至MnO2的悬浮液中(2 g的MnO2溶于6 mL的DCM中),于0 ℃搅拌约4 h至反应结束。用柱层析色谱滤去MnO2后,用无水硫酸钠干燥有机相,减压蒸除有机溶剂,用柱色谱PE:EA(10:1,v/v)分离得到化合物(Ⅰ)为440 mg,产率89%。
1H NMR(400 MHz, CDCl3)δ 8.94 (d, J = 1.6 Hz, 1H), 8.30 (dd, J = 8.7Hz, 1.7 Hz, 1H), 8.17 (d, J =7.8 Hz, 1H), 7.56-7.52 (m, 1H), 7.47-7.42 (m,2H), 7.35-7.31 (m, 1H), 4.40 (q, J = 7.3 Hz, 2H), 3.45 (s, 1H), 1.47 (t, J =7.2 Hz, 3H)。
13C NMR (100 MHz, CDCl3) δ 176.86, 143.65, 140.76, 128.12, 127.62,126.78, 123.97, 123.22, 122.96, 120.90, 120.43, 109.20, 108.29, 80.99, 79.82,37.98, 13.85。
实施例2
探针(Ⅱ)的合成:
向25 mL反应瓶中加入7-(二乙氨基)香豆素-3-甲醛(501.7 mg, 2 mmol),在0℃,N2保护下,加入10 mL的超干溶剂四氢呋喃(THF),并滴加入乙炔基溴化镁(4 mL,2mmol,0.5 M溶于THF),2.5 h反应完全。加入10 mL的饱和氯化铵溶液淬灭反应,用乙酸乙酯萃取(3×10 mL),并干燥,减压蒸除有机溶剂,得到的粗品用4 mL二氯甲烷溶解,分批(2×2mL)逐滴滴加至MnO2的悬浮液中(4 g的MnO2溶于6 mL的DCM中),于0 ℃搅拌约2 h至反应结束。用柱层析色谱滤去MnO2后,用无水硫酸钠干燥有机相,减压蒸除有机溶剂,用柱色谱PE:EA(10:1,v/v)分离得到化合物(Ⅱ)为131 mg,产率 24%。
1H NMR (400 MHz, DMSO-d 6 ) δ 8.67 (s, 1H), 7.71 (d, J = 9.1 Hz, 1H),6.82 (dd, J = 9.1 Hz, 2.2 Hz, 1H), 6.57 (d, J =1.9 Hz, 1H), 4.86 (s, 1H),3.52 (q, J = 7.0 Hz, 4H), 1.16 (t, J = 7.0Hz, 6H)。
13C NMR (100 MHz, DMSO-d 6 ) δ 172.28, 158.93, 157.62, 154.33, 150.91,133.43, 114.10, 110.96, 107.99, 96.38, 84.39, 81.86, 45.07, 12.83。
实施例3
探针(Ⅰ)的合成:
向25 mL反应瓶中加入N-乙基咔唑-3-甲醛(335.0 mg,1.5 mmol),在0 ℃,N2保护下,加入5 mL的超干溶剂四氢呋喃(THF),并滴加入乙炔基溴化镁(6 mL,3 mmol,0.5 M溶于THF),反应3 h后,加入10 mL的饱和氯化铵溶液淬灭反应,用乙酸乙酯萃取(3×10 mL),并干燥,减压蒸除有机溶剂,得到的粗品用4 mL二氯甲烷溶解,分批(2×2 mL)逐滴滴加至MnO2的悬浮液中(2 g的MnO2溶于6 mL的DCM中),于0 ℃搅拌约6 h至反应结束。用柱层析色谱滤去MnO2后,用无水硫酸钠干燥有机相,减压蒸除有机溶剂,用柱色谱PE:EA(10:1,v/v)分离得到化合物(Ⅰ)为281 mg,产率76 %。
1. 探针与半胱氨酸反应的荧光强度随时间的变化。
配制pH =7.4的PBS (10 mM)缓冲溶液;称取探针即化合物(Ⅰ),用DMSO溶解,准确配制2 mM的探针(Ⅰ)储存液;配制20 mM的半胱氨酸。向比色皿中加入1.8 mL的PBS缓冲溶液后,加入0.2 mL的DMSO,混合均匀后,加入10 µL浓度为2 mM的探针(Ⅰ)储存液,再加入20当量半胱氨酸,进行荧光光谱测试。如图3所示,该探针10 min内的发射波长为465 nm,随后逐渐红移至490 nm。
2. 探针与半胱氨酸反应的荧光强度随半胱氨酸浓度的变化。
向2 mL的PBS缓冲(10 mM,pH=7.4,含有10%的DMSO)体系中,加入10 µL浓度为2 mM的探针(Ⅰ)储存液,再加入不同浓度半胱氨酸(0-60 µM),反应5 min,以340 nm光激发,进行荧光光谱测定。随着半胱氨酸浓度的增加,荧光强度逐渐增加。如图4-5所示,对荧光强度与半胱氨酸的浓度进行线性拟合,发现半胱氨酸的浓度范围为0-20 µM时,荧光强度与浓度呈现很好的线性关系,检测限为14 nM,具有很高的灵敏度,远低于生物体内半胱氨酸的含量(30-200 µM),可以应用于生命样本中半胱氨酸的检测。
3. 不同氨基酸对探针的影响
配制20 mM的不同种类的氨基酸储备液。向2 mL的PBS缓冲(10 mM,pH = 7.4,含有10 %的DMSO)体系中,加入10 µL浓度为2 mM的探针(Ⅰ)储存液,再分别加入20当量的分析物:半胱氨酸、同型半胱氨酸、谷胱甘肽、赖氨酸,精氨酸,酪氨酸,色氨酸,苏氨酸,丝氨酸,亮氨酸,异亮氨酸,组氨酸,脯氨酸,甲硫氨酸,谷氨酰胺,谷氨酸,天冬酰胺,天冬氨酸,苯丙氨酸,缬氨酸,丙氨酸,甘氨酸),反应5 min后,进行荧光光谱测定。如图6所示,实验结果表明它种类的氨基酸不与探针发生反应,不干扰探针对半胱氨酸的特异性识别。
4. 探针对半胱氨酸的生物成像研究
在37 ℃,95 %空气,5 %二氧化碳培养箱中,将Hela细胞接种到含有10 %胎牛血清的激光共聚焦专用培养皿中贴壁培养。如图7所示,将实验分为三组,图中的a组和d组是在孵育好的细胞中加入10 µM探针(Ⅰ)孵育20 min后,分别为暗场和明场的细胞成像图。a组能观察Hela细胞有青色的荧光。e组和b组是先将细胞2 mM的N-乙基马来酰亚胺孵育20 min,再加入10 µM探针孵育20 min后,分别为暗场和明场细胞成像,观察不到细胞中的荧光,即该探针只对硫醇有荧光响应。c组和f组是先用200 µM的外源性半胱氨酸孵育20 min再孵育10 µM探针20 min后,分别为暗场和明场的细胞成像图。数据表明,探针(Ⅰ)细胞渗透性优异,且能同时检测细胞中内源性和外源性的半胱氨酸。
以上所述仅为本发明的较佳实施例而已,并不用以限制本发明,凡在本发明的精神和原则之内,所作的任何修改、等同替换、改进等,均应包含在本发明的保护范围之内。
Claims (7)
2.权利要求1所述的基于端基炔酮的半胱氨酸荧光探针的制备方法,其特征在于步骤如下:
将N-乙基咔唑-3-甲醛或7-(二乙氨基)香豆素-3-甲醛在0 ℃,N2保护下溶解于四氢呋喃中,滴加乙炔基溴化镁反应2-3 h,加入饱和氯化铵溶液进行淬灭反应,用乙酸乙酯和水萃取反应体系,并减压蒸除有机溶剂,得到的粗品用二氯甲烷溶解后,滴加至MnO2的二氯甲烷悬浮液中,0 ℃搅拌2-6 h,分离纯化分别得到结构式为(Ⅰ)或(Ⅱ)的荧光探针。
5.根据权利要求2所述的基于端基炔酮的半胱氨酸荧光探针的制备方法,其特征在于:所述N-乙基咔唑-3-甲醛或7-(二乙氨基)香豆素-3-甲醛与乙炔基溴化镁的物质的量比为1:(1-2)。
6.根据权利要求1所述的荧光探针在制备检测活细胞中半胱氨酸试剂中的应用。
7.根据权利要求6所述的应用,其特征在于所述活细胞为Hela细胞。
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Non-Patent Citations (4)
Title |
---|
A Highly Selective FRET-Based fluorescent Probe for Detection of Cysteine and Homocysteine;Hoi-Yan Shiu et al.;《Chem. Eur. J.》;20101231;第16卷;第3308-3313页 * |
Constructing a fluorescent probe for specific detection of cysteine over homocysteine and glutathione based on a novel cysteine-binding group but-3-yn-2-one;Yawei Liu et al.;《Analyst》;20140523;第139卷;第4081-4087页 * |
Highly selective red- and green-emitting two-photon fluorescent probes for cysteine detection and their bio-imaging in living cells;Zhiguang Yang et al.;《Chem. Commun.》;20120214;第48卷;第3442-3444页 * |
Rational Design of Push–Pull Fluorene Dyes:Synthesis and Structure–Photophysics Relationship;Janah Shaya et al.;《Chem. Eur. J.》;20160615;第22卷;第10627-10637页 * |
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