CN106589163A - 一种具有聚集诱导发光特性的季铵化壳聚糖荧光探针及其制备方法 - Google Patents
一种具有聚集诱导发光特性的季铵化壳聚糖荧光探针及其制备方法 Download PDFInfo
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Abstract
本发明公开了一种具有聚集诱导发光特性的季铵化壳聚糖荧光探针,其制备方法主要步骤包括:将2,3‑环氧丙基三甲基氯化铵(GTA)接到壳聚糖链上得到具有优异水溶性的季铵化壳聚糖(TMC);将四苯基乙烯荧光分子(TPE)标记到TMC上得到具有聚集诱导发光(AIE)特性的TPE‑TMC。本发明制得的荧光探针具有极好的水溶性且具有聚集诱导发光特性,与传统荧光探针相比,具有灵敏度高、光稳定性好、荧光光谱不漂移等优点。此外,由于季铵化壳聚糖固有特性,该探针带有正电荷,具有良好的水溶性和生物相容性,有望用于长周期细胞示踪、病理监测、药物代谢检测等领域。
Description
技术领域
本发明涉及一种具有聚集诱导发光特性的季铵化壳聚糖荧光探针及其制备方法。
背景技术
荧光探针是以荧光物质作为指示剂,并在一定波长光的激发下使指示剂产生荧光,通过检测所产生的荧光实现对被检测物质的定性或者定量分析。当前,荧光探针主要应用于生物、医学诊断和环境监测等领域,随着科学技术的发展,针对不同需求的探针应运而生。总体来说,可以分为三类:传统的荧光探针、无机量子点探针、新型的荧光探针。其中,传统的荧光探针最早被开发应用,但具有光不稳定性、光漂白以及聚集诱导淬灭效应等缺陷;无机量子点探针回避了传统荧光探针的缺陷,但因其含有重金属而具有不可忽视的细胞毒性问题,因此新型荧光探针脱颖而出。其中,具有聚集诱导发光(AIE)特性的探针因其卓越的荧光性能而备受关注。
目前,针对应用于生物医学研究的AIE探针,染料泄露及细胞毒性是不可忽视的两大问题。而天然大分子壳聚糖具有良好的生物相容性、可降解性,将AIE分子固定在大分子链上可有效避免染料泄漏并减低其细胞毒性。考虑到壳聚糖的溶解性,选择具有水溶性的壳聚糖衍生物势在必行。其中,季铵化壳聚糖(TMC)是壳聚糖部分糖环被季铵化后的产物,具有优异的生物相容性、生物活性、无毒性、表面带正电荷、优异的水溶性等性能,在生物医学领域备受青睐。因此,考虑到现在生物医学研究中对细胞长周期示踪以及水溶性荧光探针的迫切需求,制备一种具有优异的水溶性、易被细胞吞噬且具有长周期细胞示踪性能的荧光探针具有重要的科学意义和良好的应用前景。
发明内容
本发明的目的在于针对现有技术的不足,提供一种具有优异的水溶性、带正电荷且具有长周期细胞示踪性能的具有聚集诱导发光特性的季铵化壳聚糖荧光探针及其制备方法。
本发明的具有聚集诱导发光特性的季铵化壳聚糖荧光探针的制备方法,包括如下步骤:
1)将粘均分子量为1万-100万、脱乙酰度60%-95%的壳聚糖溶于体积分数为1%-2%的醋酸溶液中,得到壳聚糖浓度为5mg/mL-50mg/mL的溶液A;
2)将2,3-环氧丙基三甲基氯化铵(GTA)与三蒸水按体积比1:1配制成水溶液,获得溶液B;
3)将溶液A升温至45-80℃,将溶液B缓慢滴加进入溶液A,使GTA与壳聚糖中氨基的摩尔比为1:1-3:1,反应6-24h,获得溶液C;
4)将溶液C装入截留分子量大于1000的透析袋中并置于三蒸水中透析2-3天,冻干,获得水溶性的季铵化壳聚糖TMC;
5)将步骤4)中获得的TMC分散于DMSO中,在50-70℃下溶胀6-12h,再向该溶液中加入TPEITC,TPEITC与壳聚糖中氨基的摩尔比为1%-25%,反应6-24h,获得溶液D;
6)向溶液D中加入无水乙醇,无水乙醇与溶液D的体积比为15:1-25:1,搅拌均匀后,于20-25℃下静置6-12h,去除上清液,离心,所得沉淀物用三蒸水溶解,得到溶液E;
7)将溶液E装入截留分子量大于1000的透析袋中,用三蒸水透析2-5天,冻干,获得具有聚集诱导发光特性的季铵化壳聚糖荧光探针。
本发明通过将2,3-环氧丙基三甲基氯化铵接到壳聚糖链上得到水溶性的TMC;将四苯基乙烯(TPE)荧光分子标记到TMC上得到具有AIE特性且具有优异水溶性的荧光探针TPE-TMC。本发明得到的TPE-TMC分子式如图1所示,TPE-TMC核磁谱图如图2所示,样品表面电位数据如图3所示。
季铵化反应赋予壳聚糖良好的水溶性,且其链上的氯化铵基团使TMC表面带正电荷,易于粘附负电性的细胞膜以及易与带负电的体系自组装成新的纳米载体;标记上的TPE基团赋予其聚集诱导发光特性,与传统荧光探针及无机量子点探针相比,该探针具有灵敏度高,光稳定性好,荧光光谱不漂移,生物相容性好等优点。总之,本方法制备的TPE-TMC荧光探针具有优异的水溶性、易于细胞粘附及聚集诱导发光等优良特性,有望应用于细胞长周期示踪、药物代谢检测、病理监测等领域。
附图说明
图1是季铵化壳聚糖基聚集诱导发光荧光分子结构式。
图2是季铵化壳聚糖基聚集诱导发光荧光探针核磁图。
图3是季铵化壳聚糖基聚集诱导发光荧光探针样品表面电位表。
具体实施方式
以下结合附图和具体实例进一步说明本发明。
实施例1:
1)称取1g壳聚糖(粘均分子量为1万,脱乙酰度60%)加入到50ml的烧瓶中,加入20ml体积分数为1%的醋酸溶液,搅拌溶解,得到壳聚糖浓度为50mg/mL的溶液A;
2)取0.453ml的2,3-环氧丙基三甲基氯化铵,加入同体积三蒸水,配制成溶液B;
3)将溶液A升温至45℃,将溶液B滴入溶液A,使GTA与壳聚糖中氨基的摩尔比为1:1,反应6h,获得溶液C;
4)将溶液C装入截留分子量为3500的透析袋中并置于三蒸水中透析2天,冻干,获得水溶性的季铵化壳聚糖TMC;
5)称取0.1g步骤4)中获得的TMC并将其分散于10ml的DMSO中,在50℃下溶胀10h,再向该溶液中加入1mg的TPEITC,使TPEITC与壳聚糖中氨基的摩尔比为1.6%,反应6h,获得溶液D;
6)向溶液D中加入150ml的无水乙醇,使无水乙醇与溶液D的体积比为15:1,搅拌均匀后,于20℃下静置6h,去除上清液,离心,所得沉淀物用三蒸水溶解,得到溶液E;
7)将溶液E装入截留分子量为3500的透析袋中,用三蒸水透析2天,冻干,获得具有聚集诱导发光特性的季铵化壳聚糖荧光探针。
本例制得的TPE-TMC荧光探针季铵化比例为27%,TPE标记率为0.7%,产物表面电位为36.3mV。
实施例2:
1)称取1g壳聚糖(粘均分子量为19万,脱乙酰度68%)加入到50ml的烧瓶中,加入25ml体积分数为1%的醋酸溶液,搅拌溶解,得到壳聚糖浓度为40mg/mL的溶液A;
2)取0.785ml的2,3-环氧丙基三甲基氯化铵,加入同体积三蒸水,配制成溶液B;
3)将溶液A升温至55℃,将溶液B缓慢滴加进入溶液A,使GTA与壳聚糖中氨基的摩尔比为1.5:1,反应6h,获得溶液C;
4)将溶液C装入截留分子量为8000的透析袋中并置于三蒸水中透析3天,冻干,获得水溶性的季铵化壳聚糖TMC;
5)称取0.1g步骤4)中获得的TMC并将其分散于10ml的DMSO中,在55℃下溶胀8h,再向该溶液中加入3mg的TPEITC,使TPEITC与壳聚糖中氨基的摩尔比为5%,反应10h,获得溶液D;
6)向溶液D中加入170ml的无水乙醇,使无水乙醇与溶液D的体积比为17:1,搅拌均匀后,于20℃下静置8h,去除上清液,离心,所得沉淀物用三蒸水溶解,得到溶液E;
7)将溶液E装入截留分子量为8000的透析袋中,用三蒸水透析3天,冻干,获得具有聚集诱导发光特性的季铵化壳聚糖荧光探针。
本例制得的TPE-TMC荧光探针季铵化比例为34%,TPE标记率为1.7%,产物表面电位为41mV。
实施例3:
1)称取1g壳聚糖(粘均分子量为53万,脱乙酰度74.5%)加入到100ml的烧瓶中,加入50ml体积分数为1.5%的醋酸溶液,搅拌溶解,得到壳聚糖浓度为20mg/mL的溶液A;
2)取1.164ml的2,3-环氧丙基三甲基氯化铵,加入同体积三蒸水,配制成溶液B;
3)将溶液A升温至65℃,将溶液B滴入溶液A,使GTA与壳聚糖中氨基的摩尔比为2:1,反应15h,获得溶液C;
4)将溶液C装入截留分子量为14000的透析袋中并置于三蒸水中透析3天,冻干,获得水溶性的季铵化壳聚糖TMC;
5)称取0.1g步骤4)中获得的TMC并将其分散于10ml的DMSO中,在60℃下溶胀8h,再向该溶液中加入6.6mg的TPEITC,使TPEITC与壳聚糖中氨基的摩尔比为10%,反应15h,获得溶液D;
6)向溶液D中加入200ml的无水乙醇,使无水乙醇与溶液D的体积比为20:1,搅拌均匀后,于20℃下静置10h,去除上清液,离心,所得沉淀物用三蒸水溶解,得到溶液E;
7)将溶液E装入截留分子量为14000的透析袋中,用三蒸水透析3天,冻干,获得具有聚集诱导发光特性的季铵化壳聚糖荧光探针。
本例制得的TPE-TMC荧光探针季铵化比例为37%,TPE标记率为4.2%,产物表面电位为50.9mV。
实施例4:
1)称取1g壳聚糖(粘均分子量为79.6万,脱乙酰度83%)加入到250ml的烧瓶中,加入100ml体积分数为1.5%的醋酸溶液,搅拌溶解,得到壳聚糖浓度为10mg/mL的溶液A;
2)取1.656ml的2,3-环氧丙基三甲基氯化铵,加入同体积三蒸水,配制成溶液B;
3)将溶液A升温至70℃,将溶液B滴入溶液A,使GTA与壳聚糖中氨基的摩尔比为2.5:1,反应20h,获得溶液C;
4)将溶液C装入截留分子量为3500的透析袋中并置于三蒸水中透析3天,冻干,获得水溶性的季铵化壳聚糖TMC;
5)称取0.1g步骤4)中获得的TMC并将其分散于15ml的DMSO中,在65℃下溶胀10h,再向该溶液中加入11mg的TPEITC,使TPEITC与壳聚糖中氨基的摩尔比为15%,反应20h,获得溶液D;
6)向溶液D中加入300ml的无水乙醇,使无水乙醇与溶液D的体积比为20:1,搅拌均匀后,于25℃下静置10h,去除上清液,离心,所得沉淀物用三蒸水溶解,得到溶液E;
7)将溶液E装入截留分子量为14000的透析袋中,用三蒸水透析4天,冻干,获得具有聚集诱导发光特性的季铵化壳聚糖荧光探针。
本例制得的TPE-TMC荧光探针季铵化比例为41%,TPE标记率为7.3%,产物表面电位为53.6mV。
实施例5:
1)称取1g壳聚糖(粘均分子量为100万,脱乙酰度95%)加入到500ml的烧瓶中,加入200ml体积分数为2%的醋酸溶液,搅拌溶解,得到壳聚糖浓度为5mg/mL的溶液A;
2)取2.345ml的2,3-环氧丙基三甲基氯化铵,加入同体积三蒸水,配制成溶液B;
3)将溶液A升温至80℃,将溶液B缓慢滴加进入溶液A,使GTA与壳聚糖中氨基的摩尔比为3:1,反应24h,获得溶液C;
4)将溶液C装入截留分子量为14000的透析袋中并置于三蒸水中透析3天,冻干,获得水溶性的季铵化壳聚糖TMC;
5)称取0.1g步骤4)中获得的TMC并将其分散于20ml的DMSO中,在70℃下溶胀12h,再向该溶液中加入22mg的TPEITC,使TPEITC与壳聚糖中氨基的摩尔比为25%,反应24h,获得溶液D;
6)向溶液D中加入500ml的无水乙醇,使无水乙醇与溶液D的体积比为25:1,搅拌均匀后,于25℃下静置12h,去除上清液,离心,所得沉淀物用三蒸水溶解,得到溶液E;
7)将溶液E装入截留分子量为14000的透析袋中,用三蒸水透析5天,冻干,获得具有聚集诱导发光特性的季铵化壳聚糖荧光探针。
本例制得的TPE-TMC荧光探针季铵化比例为45%,TPE标记率为7.6%,产物表面电位为55.6mV。
采用本发明方法获得的季铵化壳聚糖基聚集诱导发光荧光分子的结构式如图1所示,其荧光探针核磁图如图2,上述实施例获得的各样品的表面电位表如图3。
Claims (1)
1.一种具有聚集诱导发光特性的季铵化壳聚糖荧光探针的制备方法,其特征在于,包括如下步骤:
1)将粘均分子量为1万-100万、脱乙酰度60%-95%的壳聚糖溶于体积分数为1%-2%的醋酸溶液中,得到壳聚糖浓度为5mg/mL-50mg/mL的溶液A;
2)将2,3-环氧丙基三甲基氯化铵(GTA)与三蒸水按体积比1:1配制成水溶液,获得溶液B;
3)将溶液A升温至45-80℃,将溶液B滴入溶液A,使GTA与壳聚糖中氨基的摩尔比为1:1-3:1,反应6-24h,获得溶液C;
4)将溶液C装入截留分子量大于1000的透析袋中并置于三蒸水中透析2-3天,冻干,获得水溶性的季铵化壳聚糖TMC;
5)将步骤4)中获得的TMC分散于DMSO中,在50-70℃下溶胀6-12h,再向该溶液中加入TPEITC,TPEITC与壳聚糖中氨基的摩尔比为1%-25%,反应6-24h,获得溶液D;
6)向溶液D中加入无水乙醇,无水乙醇与溶液D的体积比为15:1-25:1,搅拌均匀后,于20-25℃下静置6-12h,去除上清液,离心,所得沉淀物用三蒸水溶解,得到溶液E;
7)将溶液E装入截留分子量大于1000的透析袋中,用三蒸水透析2-5天,冻干,获得具有聚集诱导发光特性的季铵化壳聚糖荧光探针。
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