CN113880760A - 一种溶酶体靶向的双光子硫化氢荧光探针的制备方法 - Google Patents
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Abstract
Description
技术领域
本发明涉及一种溶酶体靶向的双光子硫化氢荧光探针的制备方法,属于化学与生物分析检测成像技术领域。
背景技术
因为荧光探针具有操作简便、灵敏度高、膜透性好和快速原位检测等优点。因此荧光探针在生物医学成像分析具有很好的应用前景。而双光子荧光探针因其优越的光学性能而倍受科研工作者的青睐。但是传统的荧光探针激发和发射大部分处于紫外可见光区,因此在成像时会受到组织吸收,自发荧光等的影响而使其穿透深度和分辨率受限。因此发展双光子荧光探针具有重要的作用。因为双光子荧光探针是用两个光子的近红外光激发,因此其穿透深度比传统的荧光探针在成像方面更具有优势。因此本发明专利将开发一种双光子激发的H2S荧光探针。
发明内容
本项目针对上述技术现状和存在的问题,提供一种溶酶体定位的双光子激发的H2S荧光探针NP-H2S。该荧光探针具有合成简单,反应条件温和,成本较低,且具有大的双光子吸收截面、高灵敏度和高选择性,能实现用荧光法快速便捷的检测癌细胞和组织中的好好H2S。
本发明使用荧光法检测癌细胞和组织中的H2S,以具有双光子激发的染料作为信号基团,2,4-二硝基苯醚作为硫化氢的响应基。
本发明解决问题采取的技术方案为,一种荧光法检测H2S的溶酶体定位的双光子激发近红外发射的荧光探针,其分子结构式为式I所示,该荧光探针的合成路线如下所示:
(1)将4-溴1,8-萘酐,间羟基苯氨加入反应器中,加入适量的乙酸做溶媒,在100-110度的油浴锅中反应,用薄层色谱法跟踪反应,直到4-溴1,8-萘酐完全消失则终止反应,把反应体系冷却到室温后倒入冰水中,待大量白色固体析出后,减压抽滤并用冷水洗涤3次,得到的白色固体干燥后直接用于下一步;
(2)将上一步所得的粗产物1和适当的吗啡啉,加热到80-110度反应3小时,把反应体系冷却到室温后倒入冰水中,待大量的黄色固体析出后,抽滤并用冷水洗涤3次,得到的黄色固体用恒温干燥箱干燥,干燥后直接用于下一步合成。
(3)将上一步所得的产物2,2,4-二硝基氟苯,二氯甲烷和催化量的三乙胺加入反应瓶中,25-55度反应3小时,旋干溶剂后,用柱层析提纯(洗脱剂为二氯甲烷:甲醇=20:1)得到目标探针NP-H2S。在本说明书的实施例中更详细的说明了探针的合成和检测方法。
本发明的荧光探针使用方法如下,将探针分子溶解在pH=7.4的PBS缓冲溶剂中,在室温下进行测试。当加入NaHS时,2,4-二硝基苯醚基团可以在H2S的诱导下裂解,使荧光得意恢复,探针与H2S的响应机理如图所示。
本发明的荧光探针的具体特征如下,探针自身不具有荧光发射信号,当其与H2S作用后,探针分子在525nm处有显著的绿色荧光信号发射峰,荧光强度增强了60倍;因其具有吗啡啉基团,因此,此特征将赋予其具有溶酶体定位的能力,而且经过测定,其具有很好的双光子吸收截面,因此具有双光子激发。
本发明所述的探针分子具有合成简单,合成成本低,对H2S具有高灵敏度,高选择性,且能实现用荧光法快速便捷的实现癌细胞和组织中的H2S的检测与成像。
附图说明
附图1为溶酶体定位的双光子硫化氢荧光探针的合成路线。
附图2为溶酶体定位的双光子硫化氢荧光探针与H2S的响应机理图示。
附图3为探针分子(1μM)对H2S的响应的荧光谱图,硫化氢(0-60μM)。
附图4:(a)选择性实验,1微摩尔探针分子加入40微摩尔硫化氢或者90微摩尔其它分析物。数字1到16分别是空白(探针分子),GSH,Cys,Vitamin C,K+,Ca2+,Na+,Mg2+,Zn2+,Fe3+,Gly,Cu2+,Mg2+,Blank,H2S,Pb2+,and Glu;(b)pH(3-8)对探针分子在加入H2S前后的影响。
附图5为:(A-D)溶酶体共定位成像研究。(E-F)激光共聚焦荧光显微镜对HeLa细胞中硫化氢的成像研究激发波长成像:激发波长=488和635纳米,发射波长范围=(640-680)和(500-560)纳米.所有的成像用40×的油镜,比例尺:20微米。
具体实施方式
下面结合具体实施例进一步说明本发明。下述实施例仅用于示例性说明,不能理解为对本发明的限制。除非特别说明,下述实施例中使用的原材料和设备为本领域常规使用的原材料和设备。
实施例1
本实施例提供一种溶酶体定位的双光子硫化氢荧光探针的制备方法。
本实施例溶酶体定位的双光子硫化氢荧光探针合成路线如图1所示;溶酶体定位的双光子硫化氢荧光探针与H2S的响应机理如图2所示。
本实施例具体包括以下步骤:
S1.产物1的合成:
0.277g(1.00mmol)4-溴-1,8萘酐,0.109g间羟基苯氨(1.00mmol)和20mL乙酸加入到一个100毫升的圆底烧瓶中,装上循环冷凝光,在100-110度的油浴锅中反应,用薄层色谱法跟踪反应,直到4-溴1,8-萘酐完全消失则终止反应,把反应体系冷却到室温后倒入冰水中,待大量白色固体析出后,减压抽滤并用冷水洗涤3次,得到的白色固体干燥后直接用于下一步。
S2.化合物2的合成:
将上一步所得的粗产物1(1mmol)和10mL吗啡啉,加热到80-110度反应3小时,把反应体系冷却到室温后倒入冰水中,待大量的黄色固体析出后,抽滤并用冷水洗涤3次,得到的黄色固体用恒温干燥箱干燥,干燥后直接用于下一步合成
S3.探针分子的合成:
化合物2(0.374g,1mmol)和化合物2,4-二硝基氟苯(0.186g,1mmol)溶解在50mL二氯甲烷中,同时加入3mL三乙胺,在氮气保护下,45度反应3小时,最后溶剂用旋转蒸发仪旋干,剩余物用二氯甲烷:甲醇=50:1洗脱得到目标产物.1H NMR(400MHz,d6-DMSO):8.89(s,1H),8.75(d,1H),8.48(d,1H),8.41(d,1H),8.36(d,1H),7.94(m,1H),7.49(m,1H),7.47(d,1H),7.33(d,1H),7.17(d,1H),7.09(s,1H),6.61(d,1H),3.19(t,4H),3.72(t,4H);13C NMR(100MHz,d6-DMSO)δ(ppm):53.7,66.3,160.9,116.7,138.1,121.0,158.6,126.6,137.9,129.2,134.7,132.4,121.2,128.6,114.5,157.2,107.9,155.8,117.0,130.7,141.9,121.0,139.5;LC-MS:m/z[C28H20N4O8]+calcd 540.49,found 540.5.
针对探针分子的检测,如图3~5所示。
其中:
附图3为探针分子(1μM)对H2S的响应的荧光谱图,硫化氢(0-60μM)。
附图4:(a)选择性实验,1微摩尔探针分子加入40微摩尔硫化氢或者90微摩尔其它分析物。数字1到16分别是空白(探针分子),GSH,Cys,Vitamin C,K+,Ca2+,Na+,Mg2+,Zn2+,Fe3+,Gly,Cu2+,Mg2+,Blank,H2S,Pb2+,and Glu;(b)pH(3-8)对探针分子在加入H2S前后的影响。
附图5为:(A-D)溶酶体共定位成像研究。(E-F)激光共聚焦荧光显微镜对HeLa细胞中硫化氢的成像研究激发波长成像:激发波长=488和635纳米,发射波长范围=(640-680)和(500-560)纳米.所有的成像用40×的油镜,比例尺:20微米。
Claims (3)
2.一种权利要求1所述的一种溶酶体靶向的双光子硫化氢荧光探针的制备方法,其特征在于,包括以下步骤:
S1.将4-溴1,8-萘酐,间羟基苯氨加入反应器中,加入适量的乙酸做溶媒,在100-110度的油浴锅中反应,用薄层色谱法跟踪反应,直到4-溴1,8-萘酐完全消失则终止反应,把反应体系冷却到室温后倒入冰水中,待大量白色固体析出后,减压抽滤并用冷水洗涤3次,得到的白色固体干燥后直接用于下一步;
S2.将上一步所得的粗产物1和适当的吗啡啉,加热到80-110度反应3小时,把反应体系冷却到室温后倒入冰水中,待大量的黄色固体析出后,抽滤并用冷水洗涤3次,得到的黄色固体用恒温干燥箱干燥,干燥后直接用于下一步合成;
S3.将上一步所得的产物2,2,4-二硝基氟苯,二氯甲烷和催化量的三乙胺加入反应瓶中,25-55度反应3小时,旋干溶剂后,用柱层析提纯(洗脱剂为二氯甲烷:甲醇=20:1)得到目标探针NP-H2S。
3.一种权利要求1所述的一种溶酶体靶向的双光子硫化氢荧光探针的应用,其特征在于,用于癌细胞和组织中硫化氢的荧光检测和成像分析。
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CN114773315B (zh) * | 2022-04-28 | 2023-09-19 | 韦尔通科技股份有限公司 | 一种碘鎓盐化合物及其制备方法和应用以及阳离子uv固化胶黏剂 |
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