CN110066290B - 一种有机硅席夫碱荧光探针及其应用 - Google Patents
一种有机硅席夫碱荧光探针及其应用 Download PDFInfo
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Abstract
Description
技术领域
本发明属于分析化学技术领域,具体涉及一种有机硅席夫碱荧光探针及其应用。
背景技术
六价铬(Cr6+)是一种剧毒物质,对生态环境和生物体危害极大。特别是电镀铬、金属表面处理、颜料制造和皮革鞣制等行业在世界范围内制造和丢弃了大量含有Cr6+的剧毒废物。另一方面,六价铬是一种国际公认的致癌物质,Cr6+具有很强的氧化性和致癌性,当Cr6+进入有机体后,有机体对六价铬的去除和代谢非常缓慢,它很容易在生物体中积累可导致呼吸道癌症。目前常规分析Cr6+需要较高技术人才和先进的设备,如原子吸收光谱法、电感耦合等离子体质谱法,表面增强拉曼散射光谱,尽管这些技术可以对Cr6+表现出高选择性和灵敏度,但他们的应用或多或少受到高成本和样品预处理繁琐的限制。更重要的是,这些方法只是用来检测六价铬在体外,不能用来检测生物体内的六价铬。
多年来,人们认为脂滴(LD)是简单的储存多余脂质储存库。然而,最新的研究表明,脂滴是一个重要的亚细胞器,在细胞中起着不可或缺的作用,例如,细胞膜形成,脂蛋白形成和细胞内信号转导。脂滴主要由中性脂质组成,包括三酰基甘油和胆固醇酯,表面被单层磷脂覆盖,膜蛋白嵌入在上面。脂滴不仅存在于脂肪细胞中,而且普遍存在于从细菌细胞到哺乳动物细胞的大多数细胞中。脂肪酸的储存和消耗受到严格调节,如果脂滴在这种调节中的失衡就会导致代谢紊乱如肥胖和糖尿病。因此,脂滴的实时动态监测也是目前重要的研究方向。
荧光分析克服了其他分析方法的缺点。荧光分析具有灵敏度高、特异性强、实现简单、反应时间快等优点。有关Cr6+在活细胞中的生物成像应用的报道还很缺乏。因此,设计和合成一种能够在体内外检测六价铬的荧光探针是非常必要的。
发明内容
针对现有技术中的问题,本发明提供一种有机硅席夫碱结构的荧光探针,响应速度快、抗干扰能力强。
本发明的另一目的是提供一种上述荧光探针在检测溶液中或生物细胞内Cr6+或脂滴的应用。
为实现上述目的,本发明采用如下技术方案。
一种有机硅席夫碱荧光探针,简称为Psi,其化学结构式如式(I)所示:
式(I)。
上述荧光探针的制备方法,包括以下步骤:
将氨丙基二硅氧烷和4-二苯胺基苯甲醛在二氯甲烷中反应,加入适量A4分子筛除水,在室温条件下反应,反应结束,抽滤除杂,滤液旋蒸除去多余溶剂,得到荧光探针。
所述氨丙基二硅氧烷和4-二苯胺基苯甲醛的摩尔比为1:2。
一种上述荧光探针在检测溶液或细胞中Cr6+的应用。
一种上述荧光探针在定位细胞中脂滴中的应用。
本发明的机理如下:
本发明的探针以三苯胺衍生物为母体通过Si-O-Si桥连接设计合成了三苯胺型席夫碱荧光探针。Psi主链同时具有Si-O-Si及席夫碱结构,在365 nm紫外光激发下可以发射强烈的蓝色荧光,Psi在450 nm处有较强的荧光发射,属于蓝光区。Psi在365 nm紫外光的激发下发出的荧光来源于两个方面,一方面来源于N→Si配键的存在使得硅原子中原本简并的5个3d轨道裂分,电子在裂分的轨道中吸收能量跃迁至高能级,再返回低能级的过程中释放能量发出荧光;另一方面由于席夫碱基团也是一个良好的发光基团,因此,一部分荧光来自于席夫碱基团。
本发明具有以下优点:
本发明的探针一方面具有三苯胺结构良好的光稳定性,高发射量子产率和大的摩尔消光系数的特性;另一方面结合了有机小分子硅氧烷优良特点,如:耐辐射性,耐腐蚀性和优异的生物相容性。分子中C = N键上的N原子可以通过与Cr6+配位阻断能量传递,使能量淬灭从而达到检测Cr6+的目的。探针中的有机小分子硅基团可增强透过细胞膜的能力,从而具有良好的生物相容性。抗干扰能力强。受环境变化影响程度小。本发明所述的荧光探针Psi可经“一锅法”合成获得,合成工艺简单易行,原料廉价易得,制备成本低,易于推广。
附图说明
图1是荧光探针Psi的1H NMR图谱;
图2是荧光探针Psi的13C NMR图谱;
图3是荧光探针Psi在不同浓度Cr6+条件下的荧光光谱图;
图4是荧光探针Psi离子选择性的荧光光谱图;
图5是荧光探针Psi在细胞中对Cr6+的响应图;
图6是荧光探针Psi在细胞中对脂滴的定位图。
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 荧光探针的合成
将氨丙基二硅氧烷(1.24 g 5 mmol)、4-二苯胺基苯甲醛(2.73 g 10 mmol)二氯甲烷(40.0 ml)按投料比1.0:2.0加入到100 mL单口烧瓶中,加入适量A4分子筛除去反应中产生的水,在室温条件下用磁力搅拌器搅拌24小时,反应结束,用抽滤纸过滤除去多余杂质,旋蒸除去多余溶剂,得到化合物P1,产率在86%。制得荧光探针Psi。上述荧光探针Psi的1HNMR图谱见图1,13C NMR图谱见图2。
实施例2 荧光探针对Cr6+的响应
将荧光探针Psi用乙醇作溶剂配成10 mmol/L的母液,取2μL的母液溶于2 mL H2O(25μM PBS buff,pH = 7.4,10% 乙醇)溶液当中,用去离子水配置10 mmol Cr6+,取不同浓度梯度的Cr6+(0-25 μm)加入混合均匀的离子液当中,用荧光分光光度计测试有机硅席夫碱Psi荧光性能(λex =365 nm,狭缝宽度:激发5 mm,发射5 mm),结果见图3。随着Cr6+浓度增加荧光强度降低。
实施例3 荧光探针对不同离子的选择性
用乙醇作溶剂配成10 mmol的母液,取2 μL的母液溶于2 mL H2O(25 μM PBS溶液,pH = 7.4,10%的乙醇)的混合液当中,取15当量的各种金属离子加入到混合液当中充分反应后,用荧光分光光度计测试其荧光性能。(λex =365 nm,狭缝宽度:激发5 mm,发射5 mm)结果见图4,1-16分别为空白、Cr6+、Fe3+、Mg2+、Al3+、Sn2+、Zn2+、Cu2+、Ni2+、Ba2+、Ca2+、Cr3+、Mn2+、Cd2+、Ag+、Co2+。由图4可知,荧光探针与其他各物质混合后荧光强度基本不受影响,而加入Cr6+后荧光强度明显降低。
实施例4 荧光探针在检测细胞中Cr6+的应用
HeLa细胞在35mm培养皿中以3×105细胞/皿的密度培养,HeLa细胞在37℃ 5% CO2的培养箱中培养24 h,然后除去废液,用磷酸盐缓冲溶液(PBS)洗涤2遍,加入1mL细胞培养液,用最终浓度10 μM的探针Psi培养30 min然后在双光子荧光显微镜下成像。用λex=405nm通道激发,在细胞中发出强烈的绿色荧光,形状呈现圆点状,然后分别滴加Cr6+(25,50 μM)可见绿色荧光强度逐渐降低最后接近淬灭,结果如图5所示,这表明本发明的探针可以在细胞中对Cr6+响应。
实施例5 荧光探针在细胞中对脂滴的定位
将本发明的探针与商业脂滴染料尼罗红对细胞进行复染,步骤如下:将培养好的细胞加入Psi(10 μM)共同孵育20 min,然后加入商业染料尼罗红0.5 μM再孵育10 min,分别用λex= 405 nm,λex= 561 nm激发,在红通道与绿通道中的成像图片如图6所示:绿通道中细胞中发出强烈的绿色荧光,探针荧光和红色尼罗红的荧光能够很好地重合,说明本发明的探针可以在脂滴中很好的定位。
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