CN105001662A - 一类硼酸基五甲川菁荧光染料的制备方法及应用 - Google Patents
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Abstract
本发明涉及一种硼酸基团修饰的五甲川菁染料的制备方法及应用。染料具有通式Ⅰ结构,其中R1和R2各自独立选自CH2(C6H4)B(OH)2或(CH2)3SO3H,并且不能同时为(CH2)3SO3H;R3和R4各自独立选自H或SO3H。该类染料合成路线较简便,易分离,可应用于糖类等多羟基化合物的检测。
Description
技术领域:
本发明涉及一种荧光染料的合成方法,尤其是涉及一种硼酸基团修饰的菁染料的制备及纯化方法。
背景技术:
荧光染料是指染料在吸收了可见光或者是紫外光后,能够把吸收的光转化成波长较长的可见荧光发射出来,呈现闪亮的鲜艳颜色。随着科技的进步,荧光染料作为功能性色素已广泛应用于多个领域,如印染、化学分析、生物化学、生物学、太阳能转化、染料激光器、液晶显示以及信息存储等科学技术领域。因此开发利用具有实际应用价值的各种功能性色素分子已成为当前倍受关注的研究课题。
结合使用荧光染料和分子探针的荧光光谱检测方法,由于其灵敏度高、选择性好,在分析化学,特别是生物分析中有较广泛的应用。其中,菁染料作为荧光探针与现有的其他荧光标记试剂如罗丹明、荧光素等相比具有荧光量子产率高;最大吸收波长可调谐范围大,易于合成得到近红外荧光染料;与生物基质结合后强烈的荧光增强作用;较好的稳定性等优点。
硼酸可与二羟基化合物进行可逆、高亲和性的结合,因此越来越多地被用作糖分子识别单元,进而用于设计合成外源凝集素(糖蛋白)和糖类传感器。糖广泛存在于自然界中,作为涉及生命活动本质的三类生物大分子之一,既是细胞和生物体生命活动的主要能源物质,又与多种生物分子如蛋白质存在特异性识别作用,对众多生理过程如凝血、免疫应答、受精、细胞生长、胚胎形成及细胞间信息传递等至关重要。糖的研究在生命科学和工业生产领域中意义重大,例如通过对细胞膜表面糖链的研究,可以探索癌症、细菌和病毒感染等疾病的机理;对人体血糖含量的测定可以了解人的健康状况。而在食品工业中,通过测定食品及原料的含糖量,能对食品加工过程进行监测。在这些过程中,对糖基的种类和含量的检测不可或缺,因此建立高灵敏度、高选择性的糖分子识别体系尤为重要。
发明内容:
本发明的目的是将硼酸基团引入菁染料,设计合成出可以用于检测多羟基化合物的生物探针分子。该目的可以通过以下技术方案来实现:
一种制备硼酸修饰的菁染料的方法,包括以下步骤:
1.中间体的制备:
2,3,3-三甲基吲哚啉-5-磺酸钾和1至3倍摩尔当量的溴甲基苯硼酸,以弱酸的钠盐为催化剂,在强极性溶剂中,控制反应温度为50-90℃,反应时间为4-24h得到中间体。
2.荧光染料的制备:
将得到的中间体与0.5-1倍摩尔当量的缩合剂在醋酸与醋酸酐的混合溶剂中反应0.5-2h得到染料A;将得到的中间体与1-2倍摩尔当量的缩合剂在醋酸与醋酸酐的混合溶剂中与等摩尔的5-磺酸基-1-(3-磺丙基)-2,2,3-三甲基吲哚啉季铵内盐反应0.5-2h得到染料B。
3.粗品提纯:
染料粗品用乙酸乙酯洗涤,过凝胶柱或制备液相精制得到产品。
步骤1中所述的催化剂选用醋酸钠;
步骤1中所述的溴甲基苯硼酸可以是2-溴甲基苯硼酸、3-溴甲基苯硼酸或4-溴甲基苯硼酸;
步骤2中所述的缩合剂选用β-苯胺基丙烯醛缩苯胺;
步骤2中所述的染料A的结构式为:
步骤2中所述的染料B的结构式为:
附图说明
本发明附图4幅,其中:
图1为硼酸基五甲川菁荧光染料的通式
图2为单硼酸取代染料的紫外-可见光谱;
图3为单硼酸取代染料的荧光光谱;
图4为单硼酸取代染料与不同浓度的山梨醇结合前后的荧光光谱;
具体实施方式
下面结合附图和实施例对本发明进行详细说明。
实施例1
中间体的制备:
在50mL圆底烧瓶中加入0.5g 2,3,3-三甲基吲哚啉-5-磺酸钾和1至3倍摩尔当量的溴甲基苯硼酸,以无水乙腈为溶剂,边搅拌边加入催化量的醋酸纳,氮气保护下升温至90℃,反应2h后停止加热,冷却至室温,过滤,先后用1mol/L的盐酸溶液和无水乙腈洗涤滤饼3次,真空干燥滤饼得到中间体。
实施例2
染料A的制备:
在50mL圆底烧瓶中加入0.5g中间体以及0.5倍摩尔当量的缩合剂β-苯胺基丙烯醛缩苯胺,以9mL醋酸:醋酸酐(1:2)的混合溶液为溶剂,氮气保护下升温至110℃,搅拌,溶液由深黄色变为黑色,1h后加入9mL三乙胺,溶液立即变为蓝色,15min后停止加热,冷却,静置,加入15mL乙酸乙酯,析出固体,抽滤,乙醚洗涤3次,滤饼真空干燥得到蓝色固体即为染料A。
实施例3
染料B的制备:
在50mL圆底烧瓶中加入3g 2,3,3-三甲基吲哚啉-5-磺酸钾和1.6g丙磺酸内酯,以邻二氯苯为导热剂,氮气保护下升温至120℃,搅拌,10h后停止加热,放冷,抽滤,滤饼真空干燥后取1.5g与1-2倍摩尔当量的缩合剂β-苯胺基丙烯醛缩苯胺置于50mL圆底烧瓶中,以9mL醋酸:醋酸酐(1:2)的混合溶液为溶剂,氮气保护下升温至120℃,搅拌,3h后停止反应,旋蒸,乙酸乙酯洗涤后将得到的固体真空干燥后取0.6g与等摩尔量的实施例1得到的中间体置于50mL圆底烧瓶中,依次加入3mL醋酐,3mL三乙胺,氮气保护下升温至110℃,0.5h后停止反应,冷却,静置,加乙酸乙酯洗涤,抽滤后得到染料B。
实施例4
光谱性能的评价与糖的识别性能评价:
本发明得到的产物的紫外-可见光谱见附图2,荧光光谱见附图3,对不同浓度的多羟基化合物山梨醇的荧光光谱的变化情况见附图4。
Claims (4)
1.一类硼酸基五甲川菁荧光染料,其特征在于功能基团为硼酸基团。其通式为:
其中:
R1和R2各自独立选自CH2(C6H4)B(OH)2或(CH2)3SO3H,并且不能同时为(CH2)3SO3H;
R3和R4各自独立选自H或SO3H。
2.权利要求1所述的硼酸基五甲川菁荧光染料,其中R1和R2为甲基苯硼酸时,硼酸基团可以是临位、间位或者对位。
3.权利要求1所述的硼酸基五甲川菁荧光染料,包括以下步骤:
(1)2,3,3-三甲基吲哚啉-5-磺酸钾与卤代甲基苯硼酸制得硼酸修饰的中间体,其中卤素可以是氯、溴、碘,投料比1:1-1:3,反应溶剂选自甲醇、乙醇、乙腈或丙酮,反应温度为50-90℃,反应时间为4-24h;
(2)将得到的中间体与缩合剂反应得到双硼酸取代的对称荧光染料,其中,缩合剂是β-苯胺基丙烯醛缩苯胺,投料比为1:0.5-1:1,反应溶剂是醋酸、醋酸酐或者二者的混合溶剂,反应时间0.2-2h,反应温度50-130℃;
(3)将(1)得到的中间体与等摩尔的接有缩合剂的1-(3-磺丙基)-2,2,3-三甲基吲哚啉季铵内盐反应得到单硼酸取代荧光染料,其中缩合剂是β-苯胺基丙烯醛缩苯胺,反应溶剂是醋酸、醋酸酐或者二者的混合溶剂,反应时间0.2-2h。
4.权利要求1和2中任一项的化合物在多羟基化合物检测中的应用。
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CN109678862A (zh) * | 2018-08-08 | 2019-04-26 | 青岛科技大学 | 一种多取代二苯乙烯基吲哚衍生物的制备方法 |
WO2020192271A1 (zh) * | 2019-03-26 | 2020-10-01 | 南京中硼联康医疗科技有限公司 | 一种荧光化合物、其制备方法及其用途 |
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CN109678862A (zh) * | 2018-08-08 | 2019-04-26 | 青岛科技大学 | 一种多取代二苯乙烯基吲哚衍生物的制备方法 |
CN109678862B (zh) * | 2018-08-08 | 2021-04-27 | 青岛科技大学 | 一种多取代二苯乙烯基吲哚衍生物的制备方法 |
WO2020192271A1 (zh) * | 2019-03-26 | 2020-10-01 | 南京中硼联康医疗科技有限公司 | 一种荧光化合物、其制备方法及其用途 |
JP2022510713A (ja) * | 2019-03-26 | 2022-01-27 | 南京中硼▲聯▼康医▲療▼科技有限公司 | 蛍光化合物、その製造方法及びその用途 |
JP7297066B2 (ja) | 2019-03-26 | 2023-06-23 | 南京中硼▲聯▼康医▲療▼科技有限公司 | 蛍光化合物、その製造方法及びその用途 |
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