CN104974169A - 一种荧光素类h2s荧光探针及其制备、应用 - Google Patents
一种荧光素类h2s荧光探针及其制备、应用 Download PDFInfo
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Abstract
本发明公开了一种荧光素类H2S荧光探针及其制备和应用,所述探针的制备方法为:在烧瓶中按摩尔比1:2.2加入荧光素、1-溴-2,4-二硝基苯,以无水二甲基甲酰胺为溶剂,在室温条件下搅拌反应12h,TLC跟踪至反应结束;减压蒸馏除去溶剂后得到粗产品,用硅胶柱色谱提纯,得到3',6'-双(2,4-二硝基苯氧基)-3H-螺[异苯并呋喃-1,9'-呫吨]-3-酮。本发明具有以下优点:原料便宜易得,目标产物合成步骤简单、收率高;探针激发和发射光谱在可见区,化学稳定性好。荧光探针在乙腈和HEPES的混合溶液中,对H2S具有特异的选择性并且不受其他因素的干扰。荧光探针具有较低的检测限和较短的反应时间,可以对细胞内的H2S进行实时检测,有望在医学、生物及相关领域获得广泛应用。
Description
技术领域
本发明属于分析化学领域,涉及一种荧光素类H2S荧光探针及其制备和应用,该探针是以荧光素为发色团设计的荧光素类衍生物荧光探针,通过与H2S反应生成荧光素,实现荧光“开-关”过程,以此来检测细胞内的H2S。
背景技术
众所周知,H2S是一种具有臭鸡蛋气味的有毒气体。然而,近几年的研究表明,H2S是继NO、CO之后又一重要的气体信号分子。它在调节心血管、神经、免疫、内分泌及肠胃系统方面有着重要的作用。1H2S是哺乳动物系统产生的一种内源性气体,主要由两种磷酸吡哆醛类酶,胱硫醚β-合成酶(CBS)、胱硫醚γ-裂解酶(CSE)催化L-半胱氨酸反应生成。2作为信号分子,H2S可以调节神经传递、2松弛平滑肌、3调节胰岛素的释放、4调节炎症以及抑制细胞凋亡等。5内源性的H2S水平被认为与许多疾病相关,如阿尔茨海默病、6唐氏综合症、7糖尿病8和肝硬化。9在动物疾病模型中,H2S抑制剂、H2S供体显示了H2S的治疗开发潜力。10因此,将生物体系内H2S的浓度、分布可视化显得尤为重要且有益于阐明H2S的生物学作用。
相比于已经报道的检测方法,如比色法8、电化学分析法9及气相色谱分析法10等,小分子荧光探针具有高灵敏度、实时成像、高时空分辨率等优 势。目前,已经报道的H2S荧光探针多是利用H2S的还原性或亲核性等反应特性来设计的。11-16由于特异性反应的识别机制,即使在存在干扰的情况下,大多数H2S荧光探针仍具有很高的选择性。然而,考虑到在生物组织中的应用,H2S荧光探针在设计中仍然需要考虑到其他一些因素,如生物相容性、高吸收系数、荧光量子产率、可见光激发、高稳定性和高信噪比等。
荧光素及其衍生物是生物学家和化学家广泛使用的一类有机荧光染料。由于它们良好的生物相容性、高吸光度、高荧光量子产率、良好的光稳定性等,荧光素及其衍生物经常被用于设计荧光探针、细胞标签及免疫探针等。例如,已报道的靶向FR-α的叶酸偶联异硫氰酸荧光素是第一个利用肿瘤特异性荧光成像技术对疑似卵巢癌病人肿瘤组织进行实时外科手术可视化的范例。17螺内酯型荧光素衍生物是一类无色无荧光物质,当相应的内酯开环后,就产生了强烈的绿色荧光。18近年来,由于螺环开环机理具有高信噪比的优势,人们采用这一机理成功的设计开发了大量的并用于检测金属离子、阴离子、小分子等的荧光探针。19、20但遗憾的是,只有极少数基于开环机理的荧光素衍生物被设计成H2S荧光探针并用于活细胞成像。21-24因此,我们设计合成了一种新的基于荧光素内酯开环的荧光探针,并将其应用在活细胞内H2S的检测成像。荧光素两个羟基用1-溴-2,4-二硝基苯保护起来,通过与H2S反应脱去保护、荧光素开环,实现了荧光从无到有的过程。
发明内容
本发明的目的是提供一种能够识别细胞内H2S的荧光素类荧光探针。
本发明的技术方案是,一种荧光素类检测H2S的荧光探针,结构式如下:
本发明所述荧光素类检测H2S的荧光探针的制备方法,包括以下步骤:
3',6'-双(2,4-二硝基苯氧基)-3H-螺[异苯并呋喃-1,9'-呫吨]-3-酮的合成:在无水二甲基甲酰胺中按摩尔比1:2.2~1:4.4加入荧光素、1-溴-2,4-二硝基苯,室温条件下搅拌反应过夜,TLC跟踪至反应结束;减压蒸馏除去溶剂后得到粗产品,用硅胶柱色谱提纯,得到3',6'-双(2,4-二硝基苯氧基)-3H-螺[异苯并呋喃-1,9'-呫吨]-3-酮。其合成路线如图1所示。
本发明还提供了所述荧光素类检测H2S的荧光探针的应用:该探针可用于检测细胞内的H2S。
本发明具有以下优点:原料便宜易得,目标产物合成步骤简单、收率高;探针激发和发射光谱在可见区,化学稳定性好。荧光探针在乙腈和HEPES的混合溶液中,对H2S具有特异的选择性并且不受其他因素的干扰。荧光探针具有较低的检测限和较短的反应时间,可以对细胞内的H2S进行实时检测,有望在医学、生物及相关领域获得广泛应用。
附图说明
图1本发明荧光探针的合成路线图;
图2本发明荧光探针1的1H NMR谱图;
图3本发明荧光探针1的13C NMR谱图;
图4本发明荧光探针1的HRMS谱图;
图5本发明荧光探针1与H2S反应的HPLC-MS谱图;
图6本发明荧光探针1的H2S滴定荧光发射光谱谱图;
图7本发明荧光探针1的H2S滴定紫外吸收光谱谱图;
图8本发明荧光探针1在加入H2S后随时间变化的荧光发射光谱谱图;
图9本发明荧光探针1在加入H2S后随时间变化的紫外吸收光谱谱图;
图10本发明荧光探针1针对不同阴离子的选择性柱状图;
图11本发明荧光探针1在细胞中识别H2S的荧光成像图。
具体实施方式
下面结合附图和具体实施例对本发明进行详细说明,但不限于此。
实施例1
一种荧光素类检测H2S的荧光探针的合成,基本步骤如下。
3',6'-双(2,4-二硝基苯氧基)-3H-螺[异苯并呋喃-1,9'-呫吨]-3-酮的合成:
在圆底烧瓶中按摩尔比1:2.2加入荧光素、1-溴-2,4-二硝基苯,以无水二甲基甲酰胺为溶剂,在室温条件下搅拌反应12h,TLC跟踪至反应结束。减压蒸馏除去溶剂后得到粗产品,用硅胶柱色谱提纯,得到3',6'-双(2,4-二硝基苯氧基)-3H-螺[异苯并呋喃-1,9'-呫吨]-3-酮的合成。
1H NMR(400MHz,CDCl3):δ8.86(d,J=2.8Hz,2H),8.40(dd,J=2.8Hz,2H),8.08(d,J=7.6Hz,1H),7.79-7.69(m,2H),7.26-7.20(m,3H),6.96(s, 1H),6.94(s,1H),6.87-6.84(m,2H).(如图2)
13C NMR(101MHz,CDCl3)δ168.66,155.77,154.54,152.24,142.53,140.30,135.65,130.53,130.46,128.97,126.18,125.61,123.83,122.17,120.06,116.92,116.06,108.46,81.03.(如图3)
HRMS(ESI)calcd for C32H17N4O13[MH+]665.0792,found665.0794.(如图4)
HPLC-MS跟踪荧光探针1与H2S的反应过程,结果显示:1与H2S的反应先脱去一侧羟基保护基。随着反应时间延长,脱去另一侧保护基。荧光探针1继续与H2S反应实现荧光开启响应,但醌式与酮式相互转换,同时存在。(如图5)
实施例2:荧光探针1的H2S滴定实验的溶液配制
5ml PE管中,加入20μl浓度为2mM的荧光探针1溶液,4ml CH3CN与HEPES的混合溶液。这样得到的待测溶液中含有10×10-6mol·L-1的荧光探针1。
实施例3:荧光探针1的H2S滴定荧光光谱性质的测定
图6为荧光探针1的H2S滴定荧光发射光谱。荧光探针的浓度为10×10-6mol·L-1,激发波长分别为450nm。从图6可以看出,荧光探针1随着H2S浓度的增加,荧光强度逐渐增强至30eq时基本达到平衡。所用的荧光测定仪器为Cary Eclipse Fluorescence Spectrophotometer荧光分光光度计。
实施例4
荧光探针1的H2S滴定紫外吸收光谱性质的测定
图7为荧光探针1的H2S滴定紫外吸收光谱。荧光探针的浓度为10×10-6mol·L-1。从图7可以看出,荧光探针1随着H2S浓度的增加,紫外吸收强度逐渐增强至30eq时基本达到平衡。所用的紫外测定仪器为Cary60UV-Vis紫外分光光度计。
实施例5
荧光探针1在加入H2S后随时间变化的荧光发射光谱性质的测定
图8为荧光探针1的H2S滴定荧光发射光谱。荧光探针的浓度为10×10-6mol·L-1。从图8可以看出,荧光探针1在加入H2S后,随着时间的延长,荧光强度逐渐增强至40min时基本达到平衡。所用的荧光测定仪器为Cary Eclipse Fluorescence Spectrophotometer荧光分光光度计。
实施例6:
荧光探针1在加入H2S后随时间变化的紫外吸收光谱性质的测定
图9为荧光探针1的H2S滴定紫外吸收光谱。荧光探针的浓度为10×10-6mol·L-1。从图9可以看出,荧光探针1在加入H2S后,随着时间的延长,紫外吸收强度逐渐增强至40min时基本达到平衡。所用的紫外测定仪器为Cary60UV-Vis紫外分光光度计。
实施例7:
荧光探针1对不同阴离子的选择性的荧光光谱性质的测定
图10为荧光探针1对不同阴离子的选择性的荧光光谱柱状图。荧光探针的浓度为10×10-6mol·L-1。从图10可以看出,荧光探针1对不同阴离子的选择性以H2S最佳,其它阴离子几乎没有干扰。所用的荧光测定仪器为Cary Eclipse Fluorescence Spectrophotometer荧光分光光度计。
实施例8:细胞培养及共聚焦成像步骤
图11为Hela细胞的共聚焦荧光成像图(*60)。在37℃、5%CO2条件下,将Hela细胞接种到含有10%FBS的DMEM培养基中进行体外培养。将细胞铺到24孔板里,继续在37℃、5%CO2条件下培养48h。将荧光探针1加入到培养基中继续培养30min。细胞用PBS冲洗3次。然后用100μM的H2S培养细胞30min。a为探针1细胞暗场图、b为探针1在加入H2S后的荧光成像暗场图,c为探针1细胞白场图,d为探针1在加入H2S后的细胞荧光成像白场图。荧光成像仪器为Olympus FV1000(*60)。
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上述实施例只为说明本发明的技术构思及特点,其目的在于让熟悉此项技术的人士能够了解本发明的内容并据以实施,并不能以此限制本发明的保护范围。凡根据本发明精神实质所作的等效变化或修饰,都应涵盖在本发明的保护范围之内。
Claims (4)
1.一种荧光素类检测H2S的荧光探针,其特征在于,结构式如下:
。
2.一种按照权利要求1所述荧光素类检测H2S的荧光探针的制备方法,其特征在于,包括以下步骤:
3',6'-双(2,4-二硝基苯氧基)-3H-螺[异苯并呋喃-1,9'-呫吨]-3-酮的合成:在无水二甲基甲酰胺中按摩尔比1:2.2~1:4.4加入荧光素、1-溴-2,4-二硝基苯,室温条件下搅拌反应过夜,TLC跟踪至反应结束;减压蒸馏除去溶剂后得到粗产品,用硅胶柱色谱提纯,得到3',6'-双(2,4-二硝基苯氧基)-3H-螺[异苯并呋喃-1,9'-呫吨]-3-酮。
3.一种按照权利要求1所述荧光素类检测H2S的荧光探针在检测H2S中的应用。
4.按照权利要求3所述荧光素类检测H2S的荧光探针在检测H2S中的应用,其特征在于:H2S的检测体系为CH3CN、HEPES混合溶剂中和细胞中。
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