CN111333668B - 一类近红外孔雀绿染料及其合成方法和应用 - Google Patents
一类近红外孔雀绿染料及其合成方法和应用 Download PDFInfo
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Abstract
本发明提供了一类近红外孔雀绿染料及其合成方法和应用,该染料的结构式如(1)所示,该化合物的制备方法是将久洛尼定衍生物与相应的醛在酸催化下经高温回流反应得到;其具有近红外吸收,刺激响应等特点,可应用于刺激响应材料、生物荧光探针和生物荧光成像等领域。
Description
技术领域
本发明属于染料领域,具体涉及一类近红外孔雀绿染料及其合成方法和应用。
背景技术
硅罗丹明特殊的内酯-两性离子平衡赋予其光生探针的特性,有效降低了荧光成像过程中非特异性标记的荧光背景,是目前广受关注的明星染料。然而硅罗丹明复杂的合成步骤依旧限制这类近红外范围的光生探针的发展。
将硅罗丹明10号位桥连基团剔除得到最大吸收约620nm的孔雀绿。由于桥连基团的缺失使得孔雀绿母环刚性结构无法维持,荧光量子产率趋近于0,通过限制9号位中心碳原子连接的芳环自由扭转能使得量子产率发生上千倍的提升。基于这一原理,通过与限制扭转的荧光激活蛋白结合,孔雀绿能发出荧光从而应用于荧光标记成像中。
孔雀绿具有与硅罗丹明类似的结构,同时由于无需引入桥连原子,合成更为简单,价格仅为硅罗丹明的十万分之一,是理想的硅罗丹明替代品。但传统孔雀绿最大吸收波长在620nm附近,与近红外范围的硅罗丹明(约650nm)仍有一定差距。
发明内容
本发明的目的在于提供一类近红外孔雀绿染料及其合成方法和应用;其将在刺激响应材料、生物荧光探针和生物荧光成像等领域中发挥作用。
本发明一类近红外孔雀绿类染料,具有下列结构通式:
其中:R1,R2,R3,R4,R5分别为H、C1-20烷基、C1-20烷基任意取代的苯基、C1-20烷基任意取代的萘基、卤素、羧基、羟基、巯基、氰基、硝基、磺酸基、杂环基、卤代烷基、烷基氨基、酰胺基、烷氧基、取代烷基、取代环烷基、环烷基、芳基、取代芳基;
X-=F-,Cl-,Br-,I-,CH3COO-,CF3COO-,ClO4 -,SO4 2-,PO4 3-。
特别的,当R1为羧基或羧酸阴离子时,可以形成通式(I)相应的内酯螺环形式,具有通式(II)结构的化合物:
本发明一类近红外孔雀绿类染料的合成方法,该荧光团的合成路线如下:
其中:R1,R2,R3,R4,R5分别为H、C1-20烷基、C1-20烷基任意取代的苯基、C1-20 烷基任意取代的萘基、卤素、羧基、羟基、巯基、氰基、硝基、磺酸基、杂环基、卤代烷基、烷基氨基、酰胺基、烷氧基、取代烷基、取代环烷基、环烷基、芳基、取代芳基。具体步骤为:(1)染料分子的合成
久洛尼定与苯甲醛衍生物溶于甲苯中,加入催化剂,120-150℃回流反应 10-24小时后降至室温,在反应液中加入氧化剂,15-30℃反应1-5小时。反应结束后减压蒸出溶剂,得到染料分子粗产品。
其中,苯甲醛衍生物与久洛尼定的摩尔质量比为1:2-5;
苯甲醛衍生物与甲苯的质量比为1:20-50;
催化剂的用量为苯甲醛衍生物的10%;
氧化剂与苯甲醛的摩尔质量比为1:1-2;
(2)染料分子的提纯
将上述步骤(1)得到的粗产品经过柱层析分离提纯得到的目标荧光团分子。不同的阴离子X-是通过离子交换法将产物溶解在氢氧化钠溶液中,析出沉淀后,再加入阴离子酸,在乙醇中回流3-8小时,析出沉淀,过滤得到相应的盐。
本发明首次将久洛尼定结构引入到孔雀绿类染料中,使得荧光团具有近红外波长,水致变色等特点,可应用于刺激响应材料、生物荧光探针和生物荧光成像等领域。
附图说明
图1本发明实施例1制备的染料的核磁谱图氢谱;
图2本发明实施例1制备的染料的核磁谱图碳谱;
图3本发明实施例3制备的染料的核磁谱图氢谱;
图4本发明实施例4制备的染料的核磁谱图氢谱;
图5本发明实施例4制备的染料的核磁谱图碳谱;
图6本发明实施例1制备的染料的紫外-可见吸收光谱;
图7本发明实施例1制备的染料与标记细胞核的绿色荧光蛋白在Hela细胞中共定位。其中,a为405nm激发下的细胞成像,b为640nm激发下的细胞成像, c为a、b图像的叠加。
图8本发明实施例3制备的染料的紫外-可见吸收光谱;
图9本发明实施例4制备的染料的紫外-可见吸收光谱;
具体实施方式
下面的实施例将对本发明予以进一步的说明,但并不因此而限制本发明。
实施例1
孔雀绿染料(R1=R2=R4=R5=H,R3=OCH2CH2CH2COOCH2CH3,X=Cl-) 的制备,基本合成过程如下:
将347mg久洛尼定,236mg对位修饰苯甲醛,190mg对甲苯磺酸一水合物溶于5mL甲苯中,120℃下回流10小时后降至室温,加入246mg四氯苯醌 15℃下反应1小时,旋干溶剂硅胶柱层析纯化得190mg目标化合物。合成染料的核磁氢谱如图1所示;核磁碳谱如图2所示,具体数据如下:
1H NMR(400MHz,MeOD)δ7.22(d,J=8.0Hz,2H),7.10(d,J=8.8Hz,2H), 6.91(s,4H),4.29–4.13(m,4H),3.55(t,J=5.8Hz,8H),2.75(t,J=6.2Hz,8H), 2.57(t,J=7.2Hz,2H),2.23–2.11(m,2H),2.09–1.93(m,8H),1.28(t,J=7.2Hz, 3H).13C NMR(101MHz,MeOD)δ175.14,174.89,164.52,152.53,138.20,137.96, 133.69,129.75,127.90,126.95,124.12,115.62,68.62,61.65,52.00,31.60,28.40, 25.66,21.89,14.55.
实施例2
孔雀绿染料(R1=R2=R4=R5=H,R3=OCH2CH2CH2COOCH2CH3,X= CF3COO-)的制备,基本合成过程如下:
将100mg实施例1制备的化合物溶解在氢氧化钠溶液中,析出沉淀后,在加入2mLCF3COOH,在乙醇中回流3h,析出绿色沉淀,过滤得到90mg目标化合物。合成染料的核磁氢谱;核磁碳谱数据如下:
1H NMR(400MHz,MeOD)δ7.22(d,J=8.0Hz,2H),7.10(d,J=8.8Hz,2H), 6.91(s,4H),4.29–4.13(m,4H),3.55(t,J=5.8Hz,8H),2.75(t,J=6.2Hz,8H), 2.57(t,J=7.2Hz,2H),2.23–2.11(m,2H),2.09–1.93(m,8H),1.28(t,J=7.2Hz, 3H).13C NMR(101MHz,MeOD)δ175.14,174.89,164.52,152.53,138.20,137.96, 133.69,129.75,127.90,126.95,124.12,115.62,68.62,61.65,52.00,31.60,28.40, 25.66,21.89,14.55.
实施例3
孔雀绿染料(R1=COO-,R2=R3=R5=H,R4=COOH)的制备,基本合成过程如下:
将347mg久洛尼定,95mg 2-醛基-4-羧基苯甲酸,11mg溴化铜溶于15mL 甲苯中,150℃下回流24小时后降至室温,加入454mg二氯二氰基苯醌30℃下反应5小时,旋干溶剂硅胶柱层析纯化得48mg目标分子。合成染料的核磁氢谱如图3所示,具体数据如下:
1H NMR(400MHz,CDCl3)δ8.23–8.06(m,2H),7.84(d,J=7.9Hz,1H),6.63 (s,4H),3.12–2.94(m,8H),2.58(t,J=6.5Hz,8H),1.98–1.70(m,8H).
实施例4
孔雀绿染料(R1=COO-,R2=R3=R5=H,R4=COOCH3)的制备,基本合成过程如下:
将347mg久洛尼定,104mg 2-醛基-4-甲酯苯甲酸,11mg溴化铜溶于10mL 甲苯中,130℃下回流18小时后降至室温,加入246mg四氯苯醌25℃下反应2 小时,旋干溶剂硅胶柱层析纯化得70mg目标分子。合成染料的核磁氢谱如图4 所示;核磁碳谱如图5所示,具体数据如下:
1H NMR(400MHz,CDCl3)δ8.06(d,J=8.1Hz,2H),7.84(d,J=8.0Hz,1H), 6.63(s,4H),3.86(s,3H),3.04(t,J=5.6Hz,8H),2.58(t,J=6.5Hz,8H),1.92– 1.71(m,8H).13CNMR(101MHz,CDCl3)δ169.57,166.08,153.74,142.85,134.95, 129.79,129.44,126.84,125.95,125.54,125.41,120.92,93.62,52.60,49.86,27.74, 21.86.
实施例5
实施例1制备的染料在水中的紫外-可见吸收光谱。
用20mM HEPES溶液(pH=7.4)将实施例1合成的染料配制成10μM浓度,测定的紫外-可见吸收光谱如附图6所示。从图中可以看出实施例1合成的孔雀绿染料的最大吸收波长在646nm。
实施例6
实施例1制备的染料用于细胞成像
图7中细胞为Hela,所用染料为实施例1中合成,浓度为2μM。在共聚焦小皿中以2万细胞/培养皿的浓度接种Hela细胞,37℃,5%CO2,10%胎牛血清的1640培养基条件下培养18小时后将pcDNA3.1-NLS-myc-dL5-2XG4S-mCer3 质粒按LipoHigh脂质体高效转染试剂说明进行转染,继续培养36小时后用于荧光成像。将实施例1制备的染料加入培养基中使其终浓度为2μM,孵育30min 后置于共聚焦显微镜下观察。可明显观测到实施例1合成的染料与标记细胞核的绿色荧光蛋白具有良好的共定位效果。
实施例7
实施例3制备的染料在含0.1%三氟乙酸的乙醇中的紫外-可见吸收光谱。
用含0.1%三氟乙酸的乙醇将实施例3合成的染料配制成10μM浓度,测定的紫外-可见吸收光谱如附图8所示。从图中可以看出实施例3合成的孔雀绿染料的最大吸收波长在658nm。
实施例8
实施例4制备的染料在含0.1%三氟乙酸的乙醇中的紫外-可见吸收光谱。
用含0.1%三氟乙酸的乙醇将实施例4合成的染料配制成10μM浓度,测定的紫外-可见吸收光谱如附图9所示。从图中可以看出实施例4合成的孔雀绿染料的最大吸收波长在664nm。
Claims (4)
1.一类近红外孔雀绿染料的合成方法,其特征在于该染料具有如下结构:
该方法的具体步骤如下:
(1)染料的合成
将久洛尼定与苯甲醛衍生物溶于甲苯中,加入催化剂,120-150℃回流反应10-24小时后降至室温,在反应液中加入氧化剂,15-30℃反应1-5小时;反应结束后减压蒸出溶剂,得到染料粗产品;
所述苯甲醛衍生物与久洛尼定的摩尔质量比为1:2-5;
所述苯甲醛衍生物与甲苯的质量比为1:20-50;
所述催化剂与苯甲醛衍生物的摩尔质量比为1:5-10;
所述氧化剂与苯甲醛的摩尔质量比为1:1-2;
(2)染料的提纯
将上述步骤(1)得到的粗产品经过柱层析分离提纯得到的目标染料;不同的阴离子是通过离子交换法将产物溶解在氢氧化钠溶液中,析出沉淀后,再加入阴离子酸,在乙醇中回流3-8小时,析出沉淀,过滤得到相应的染料。
2.根据权利要求1所述的一类近红外孔雀绿染料的合成方法,其特征在于:步骤(1)中所述的催化剂为对甲苯磺酸,溴化铜中的一种。
3.根据权利要求 1所述的一类近红外孔雀绿染料的合成方法,其特征在于:步骤(1)中所述的氧化剂为四氯苯醌、二氯二氰基苯醌中的一种。
4.根据权利要求1所述的一类近红外孔雀绿染料的合成方法,其特征在于:步骤(2)中阴离子酸为:HCl、CF3COOH。
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