CN106928202B - 一种低毒性荧光聚集标记分子及其合成方法 - Google Patents
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Abstract
本发明公开一种低毒性荧光聚集标记分子及其合成方法。该低毒性荧光聚集标记分子结构式如式(I)。2‑叠氮‑4，6‑二取代‑1，3，5‑三嗪(II)、四苯乙炔(III)、无水硫酸铜、L‑抗败血酸钠加入到叔丁醇与去离子水的混合液中溶解搅拌，加热至60～90℃后反应3～20小时；反应结束把叔丁醇旋干，二氯甲烷萃取，洗涤干燥，过滤旋干，用柱层析分离得到产品荧光标记物I。本发明提供一种低毒性的荧光标记分子，而且是在荧光聚集状态下发光。
Description
技术领域
本发明涉及一种低毒性荧光聚集标记分子及其合成方法。
背景技术
在传统的发光材料中，发光物质在溶液中能发出很强的荧光，而在聚集态或固态却没有荧光发出，主要是由于分子之间π-π作用的影响，导致了非辐射能的耗散。最近，具有聚集诱导发光(AIE)的分子引起了人们的热捧。在这其中，四苯基乙烯(TPE)是一种结构简单且具有明显的聚集诱导发光的分子。科学家们利用TPE分子去构建不同的固态发光物质和其他功能性的材料，尤其在有机发光二极管(OLED)和生物检测方面等。在生物检测中，传统的发光物质在聚集状态的荧光往往是猝灭的，这就是聚集导致的荧光猝灭现象(ACQ)，这种荧光猝灭现象很大程度上限制了生物样品的标记深度，这就让研究者不得不用稀溶液作为生物检测的应用，这就使检测的灵敏度降低。
发明内容
本发明的一个目的是针对现有技术的不足，利用四苯基乙烯(TPE)具有聚集诱导发光的特性，提供了一种低毒性荧光聚集标记分子，为2,4-二取代-6-[5-(4-三苯乙烯-苯基)-[1,2,3]三唑-1-取代]-[1,3,5]三嗪(I)，其结构式如下：
其中:R1和R2分别为氯、溴、巯基或氨基中的一种。
本发明的另一个目的是提供上述低毒性荧光聚集标记分子的合成方法，其所采用的技术方案：
2-叠氮-4，6-二取代-1，3，5-三嗪(II)、四苯乙炔(III)、无水硫酸铜、L-抗败血酸钠加入到叔丁醇与去离子水的混合液中溶解搅拌，加热至60～90℃后反应3～20小时；反应结束把叔丁醇旋干，二氯甲烷萃取，洗涤干燥，过滤旋干，用柱层析分离得到产品荧光标记物I；
2-叠氮-4，6-二取代-1，3，5-三嗪、四苯乙炔、无水硫酸铜、L-抗败血酸钠的摩尔比为1～2:1:0.1～0.3:1～1.5。
本发明的有益效果是：
1、本发明提供一种低毒性的荧光标记分子，而且是在荧光聚集状态下发光。
2、本发明提供的一种低毒性新型荧光聚集标记分子，分子中带有：氯、溴、巯基或氨基取代基，可方便进一步衍生化反应。
附图说明
图1是光标记物I的Hela细胞毒性试验；
图2是光标记物I的GSE-1细胞毒性试验；
图3是3h后荧光标记物I的细胞摄取图像。
具体实施方式
下面结合具体实施例对本发明做进一步的分析。
实施例1
1.2mmol 2-叠氮-4，6-二氯-1，3，5-三嗪、1.0mmol四苯乙炔、0.1mmol无水硫酸铜、1.0mmol L-抗败血酸钠加入到20mL叔丁醇与2mL去离子水的混合液中溶解搅拌，加热至90℃后反应8小时；反应结束把叔丁醇旋干，二氯甲烷萃取，洗涤干燥，过滤旋干，用柱层析分离得到产品荧光标记物I。
产物荧光标记物的表征如下：
Mp:146～147℃
MS(ESI):m/z(％)547.5672[M+H]+
IRvmax/cm-1:3440，3070,3022，2960，2918，2849，2194，1733，1621，1513，1456，1410，1306，1260，1076，1051，1018.
1H NMR(500MHz,CDCl3)δ7.99(d,J＝3.7Hz,1H),7.42(d,J＝8.1Hz,2H),7.22～7.00(m,17H).
13C NMR(126MHz,CDCl3)δ173.18(s),163.48(s),132.47(s),131.65(s),131.54～131.14(m),129.39(s),127.91(d,J＝5.3Hz),127.71(s),127.28(s),127.05～126.73(m).
实施例2
1.1mmol 2-叠氮-4，6-二溴-1，3，5-三嗪、1.0mmol四苯乙炔、0.1mmol无水硫酸铜、1.0mmol L-抗败血酸钠加入到20mL叔丁醇与2mL去离子水的混合液中溶解搅拌，加热至80℃后反应15小时；反应结束把叔丁醇旋干，二氯甲烷萃取，洗涤干燥，过滤旋干，用柱层析分离得到产品荧光标记物I。
实施例3
1.2mmol 2-叠氮-4，6-二巯基-1，3，5-三嗪、1.0mmol四苯乙炔、0.3mmol无水硫酸铜、1.5mmol L-抗败血酸钠加入到20mL叔丁醇与2mL去离子水的混合液中溶解搅拌，加热至90℃后反应3小时；反应结束把叔丁醇旋干，二氯甲烷萃取，洗涤干燥，过滤旋干，用柱层析分离得到产品荧光标记物I。
实施例4
1.2mmol 2-叠氮-4，6-二氨基-1，3，5-三嗪、1.0mmol四苯乙炔、0.2mmol无水硫酸铜、1.0mmol L-抗败血酸钠加入到20mL叔丁醇与2mL去离子水的混合液中溶解搅拌，加热至80℃后反应10小时；反应结束把叔丁醇旋干，二氯甲烷萃取，洗涤干燥，过滤旋干，用柱层析分离得到产品荧光标记物I。
实施例5
1.2mmol 2-叠氮-4-氨基-6-巯基-1，3，5-三嗪、1.0mmol四苯乙炔、0.1mmol无水硫酸铜、1.0mmol L-抗败血酸钠加入到20mL叔丁醇与2mL去离子水的混合液中溶解搅拌，加热至60℃后反应20小时；反应结束把叔丁醇旋干，二氯甲烷萃取，洗涤干燥，过滤旋干，用柱层析分离得到产品荧光标记物I：
应用实施例1：MTT法测定产物I的细胞毒性
1、细胞接种：
1-1Hela细胞用含10％小牛血清的DMEM培养液配成单个细胞悬液；
1-2GSE-1细胞用含10％胎牛血清的DMEM培养液配成单个细胞悬液；
1-3将细胞接种到96孔板上，每孔8000细胞，每孔体积200μL。
2、细胞培养：将培养板放入CO2培养箱，在37℃，5％CO2及饱和湿度条件下，培养16～18h。
3、吸去培养液，用PBS清洗细胞，加入无血清培养液，在细胞孔中分别加入产物IDMSO溶液，使每孔中产物的浓度分别为20μg·mL-1,40μg·mL-1,60μg·mL-1,80μg·mL-1,120μg·mL-1,160μg·mL-1,200μg·mL-1,240μg·mL-1,每孔液体的总体积为200μL(每个样品每种浓度都为三复孔)
4、产物I与细胞共孵育24h。吸去培养基，每孔加入90μL无血清培养液和
10μL 5mg·mL-1MTT溶液，37℃孵育3h。
5、翻板法弃去液体，每孔加入100μL DMSO，在微量振荡器上震荡10min。在酶标仪上测570nm波长处OD值，计细胞活力。
图1、2中可见产物在GSE-1和Hela细胞中在120μg·mL-1浓度时，细胞毒性低于50％。
应用实施例2：荧光标记物I的细胞摄取实验
(1)细胞接种
将普通洁净盖玻片放入70％乙醇中浸泡5min，于超净台内吹干。将盖玻片置于24孔板内，种入细胞培养过夜，使细胞密度为70％～80％。将圆形载玻片放入24孔板中每个孔中。
神经交质瘤细胞，用含10％小牛血清的DMEM培养液配成细胞悬液，将细胞接种到24孔板上，每孔2×104细胞，每孔体积500μL。于CO2培养箱中培养24h,待细胞密度为70％～80％时进行摄取实验。
(2)荧光标记物I溶液用DMSO配制成20μg·mL-1的溶液。
(3)细胞摄取实验
孵育24h后，将24孔板中的培养液吸去，加入400μL无血清的DMEM培养液，将配好的两种溶液分别加入24孔板中，于37℃、5％CO2培养箱中培养2.5h后，取出再重复上面做法再吸去两个孔板中的培养液，加入400μL无血清的DMEM培养液，将配好的溶液加入24孔板中，于37℃，5％CO2培养箱中培养3h。
吸去培养液，用PBS洗涤3次，每次200μL，吸去PBS，每孔加入200μL0.5μg·mL- 1Hoechst溶液，孵育6min后，吸去Hoechst溶液，用PBS洗涤3次。
(4)倒置荧光显微镜观察
图3为3h后荧光标记物I的细胞摄取图像；(a)为白光条件下细胞摄取图像，(b)为蓝光条件下细胞摄取图像，(c)为(a)(b)两图合并的效果图。
Claims (4)
1.一种低毒性荧光聚集标记分子，其特征在于为化合物(I)，其结构式如下：
其中:R1和R2各自独立为氯、溴、巯基或氨基中的一种。
2.如权利要求1所述的一种低毒性荧光聚集标记分子的制备方法，其特征在于该方法的反应式如下：
其中:R1和R2各自独立为氯、溴、巯基或氨基中的一种。
3.如权利要求2所述的一种低毒性荧光聚集标记分子的制备方法，其特征在于该方法具体是化合物(II)、化合物(III)、无水硫酸铜、L-抗败血酸钠加入到叔丁醇与去离子水的混合液中溶解搅拌，加热至60～90℃后反应3～20小时；反应结束把叔丁醇旋干，二氯甲烷萃取，洗涤干燥，过滤旋干，用柱层析分离得到化合物(I)。
4.如权利要求3所述的一种低毒性荧光聚集标记分子的制备方法，其特征在于化合物(II)、化合物(III)、无水硫酸铜、L-抗败血酸钠的摩尔比为1～2:1:0.1～0.3:1～1.5。
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| WO2013029340A1 (en) * | 2011-09-01 | 2013-03-07 | The Hong Kong University Of Science And Technology | Biocompatible nanoparticles with aggregation induced emission characteristics as fluorescent bioprobes and methods of using the same for in vitro and in vivo imaging |
| CN103804318A (zh) * | 2014-02-14 | 2014-05-21 | 中山大学 | 含三苯乙烯或四苯乙烯结构的具有聚集诱导发光性能的苯并噻唑衍生物及其制备方法和应用 |
| CN104592238A (zh) * | 2015-01-24 | 2015-05-06 | 吉林大学 | 芘并咪唑衍生物及其制备方法,及电致发光器件 |
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| CN103804318A (zh) * | 2014-02-14 | 2014-05-21 | 中山大学 | 含三苯乙烯或四苯乙烯结构的具有聚集诱导发光性能的苯并噻唑衍生物及其制备方法和应用 |
| CN104592238A (zh) * | 2015-01-24 | 2015-05-06 | 吉林大学 | 芘并咪唑衍生物及其制备方法,及电致发光器件 |
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