CN107814808A - 一种近红外反应型双光子荧光探针及其制备方法和应用 - Google Patents

一种近红外反应型双光子荧光探针及其制备方法和应用 Download PDF

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CN107814808A
CN107814808A CN201710916602.5A CN201710916602A CN107814808A CN 107814808 A CN107814808 A CN 107814808A CN 201710916602 A CN201710916602 A CN 201710916602A CN 107814808 A CN107814808 A CN 107814808A
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钱鹰
姚善昆
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Abstract

本发明提供一种近红外反应型双光子荧光探针，该近红外反应型双光子荧光探针为一种由1,3,3‑三甲基‑2‑亚甲基吲哚啉‑罗丹明酰肼与4‑吗啉基‑1,8‑萘酰亚胺‑苯基异硫氰酸酯反应制得的荧光分子。本发明还提供该近红外反应型双光子荧光探针的制备方法和应用。本发明的近红外反应型双光子荧光探针，发射近红外波段红色荧光，通过汞离子诱导的酰胺基硫脲脱硫‑环化反应及1,3,3‑三甲基‑2‑亚甲基吲哚啉‑罗丹明内酰胺的开环反应等多步串联反应可灵敏调控其在近红外波段的荧光性能，灵敏度高、选择性强、生物相容性好，在近红外双光子荧光成像、双光子荧光传感器、生物荧光分析、荧光标记、环境监测等领域具有广泛应用。

Description

一种近红外反应型双光子荧光探针及其制备方法和应用
技术领域
本发明涉及荧光探针技术领域，具体涉及一种近红外反应型双光子荧光探针及其制备方法和应用。
背景技术
反应型荧光探针通过化学反应直接改变探针分子的结构，引起其光谱信号的明显改变，从而实现光学传感和目标物识别。罗丹明是制备反应型荧光探针的理想材料。2014年，Wang等报道了罗丹明-萘酰亚胺铁离子荧光探针(Cuicui Wang,Di Zhang,XiaoyanHuang,Peigang Ding,Zhenji Wang,Yufen Zhao,Yong Ye.A fluorescenceratiometricchemosensor for Fe3+based on TBET and its application in livingcells.Dyes and Pigments,Talanta,128,2014,69-74)；2015年，Zhang等报道了罗丹明-氨基吗啉萘二甲酰的pH荧光探针(Xiaofan Zhang,Tao Zhang,ShiliShen,Junying Miao andBaoxiang Zhao.A ratiometriclysosomal pH probe based on the naphthalimide-rhodamine system.Journal of Materials Chemistry B,2015,3,3260-3266)；2017年，Shen等报道了罗丹明-萘酰亚胺的次氯酸荧光探针并应用于细胞成像(ShiliShen,JunyaNing,Xiaofan Zhang,Junying Miao,Baoxiang Zhao.Through-bond energytransfer-based ratiometric fluorescent probe for the imaging of HOCl inliving cells.Sensors and Actuators B:Chemical,2017,244,907-913)。
近红外双光子荧光探针其荧光发射波长位于近红外区，在生物组织中穿透力强，灵敏度高、干扰小、安全可靠。但现有技术中反应型罗丹明荧光探针大部分仅发射线性荧光而没有双光子荧光，且线性荧光发射波长大部分小于670nm，极大地限制了其应用范围。发展高效便捷的有机合成方法对罗丹明进行结构修饰，制备发射波长位于红光或近红外区域的反应型双光子荧光探针是近期的研究热点。
发明内容
本发明的第一个目的是提供一种荧光发光性能优异、灵敏度高、生物相容性好的荧光分子，作为近红外波段反应型双光子荧光探针。
本发明的第二个目的是提供上述荧光分子的制备方法。
本发明的第三个目的是提供上述荧光分子作为近红外波段反应型双光子荧光探针在近红外双光子荧光成像、双光子荧光传感器、生物荧光分析、荧光标记或重金属离子检测方面的应用。
技术方案：本发明提供一种荧光分子，为结构式1表示的化合物：
该荧光分子由1,3,3-三甲基-2-亚甲基吲哚啉-罗丹明酰肼与4-吗啉基-1,8-萘酰亚胺-苯基异硫氰酸酯反应制得；1,3,3-三甲基-2-亚甲基吲哚啉-罗丹明酰肼为结构式2表示的化合物，4-吗啉基-1,8-萘酰亚胺-苯基异硫氰酸酯为结构式3表示的化合物：
该荧光分子的制备方法包括：惰性气体保护下，将1,3,3-三甲基-2-亚甲基吲哚啉-罗丹明酰肼与4-吗啉基-1,8-萘酰亚胺-苯基异硫氰酸酯加入到干燥乙腈中，75～80℃下搅拌反应12～24h，提纯，即得所述荧光分子(CRPM)。提纯方法为：将反应结束后得到的产物进行萃取、干燥后用柱色谱提纯。
本发明另一方面提供一种近红外反应型双光子荧光探针，该近红外双光子荧光探针为上述荧光分子。
本发明另一方面提供上述近红外反应型双光子荧光探针在近红外双光子荧光成像、双光子荧光传感器、生物荧光分析或荧光标记方面的应用。
本发明另一方面提供上述近红外反应型双光子荧光探针在检测Hg2+中的应用。
有益效果：本发明的荧光分子为近红外反应型双光子荧光探针，其包含1,3,3-三甲基-2-亚甲基吲哚啉-罗丹明和4-吗啉基-1,8-萘酰亚胺复合荧光团，该荧光分子发射近红外波段红色荧光，通过汞离子诱导的酰胺基硫脲脱硫-环化反应及1,3,3-三甲基-2-亚甲基吲哚啉-罗丹明内酰胺的开环反应等多步串联反应可灵敏调控该荧光分子在近红外波段的荧光性能，其灵敏度高、选择性强、生物相容性好，可作为性能优异的近红外波段双光子荧光染料，在近红外双光子荧光成像、双光子荧光传感器、生物荧光分析、荧光标记、环境监测等领域具有广泛应用。
附图说明
图1是均匀分散有荧光分子CRPM的缓冲溶液(缓冲溶液pH为7.4，溶剂为体积比1∶1的水和乙醇组成的混合溶剂，荧光分子CRPM的浓度为10-4mol/L)中加入不同金属离子(加入的金属离子浓度为10-4mol/L)在800nm飞秒激光激发下的双光子诱导荧光光谱。
具体实施方式
实施例1
(1)荧光分子CRPM的制备方法为：
氮气保护下，将1,3,3-三甲基-2-亚甲基吲哚啉-罗丹明内酰肼(0.50g,0.87mmol)溶于30mL无水乙腈中，加入4-吗啉基-1,8-萘酰亚胺-苯基异硫氰酸酯(0.36g,0.87mmol)，磁力搅拌，回流反应24h，温度控制在80℃。结束反应，经萃取、干燥、柱色谱提纯，得到CRPM，产率45％。
化合物CRPM的合成路线如下：
其中1,3,3-三甲基-2-亚甲基吲哚啉-罗丹明酰肼按文献方法制备(JunyingXie,Chunyan Li,Yongfei Li,JunjieFei,Fen Xu,Juanou Yang,and Juan Liu.Near-InfraredFluorescent Probe with High Quantum Yield and Its Application in theSelective Detection of Glutathione in Living Cells and Tissues.AnalyticalChemistry,2016,88,9746～9752)。4-吗啉基-1,8-萘酰亚胺-苯基异硫氰酸酯按文献方法制备(Jianhua Song,ManxiuHuai,Cuicui Wang,ZhanhuiXu,Yufen Zhao,Yong Ye.A newFRET ratiometric fluorescent chemosensor for Hg2+and its application in livingEC 109 cells.SpectrochimicaActa Part A:Molecular andBiomolecularSpectroscopy,2015,139,549-554)。
(2)对所得化合物进行结构表征：
核磁共振氢谱1H NMR(500MHz,CDCl3):δ:8.60(d,J＝7.0Hz,1H),8.54(d,J＝7.5Hz,1H),8.46(d,J＝8.5Hz,1H),7.98(t,J＝7.5Hz,1H),7.92(s,1H),7.72(t,J1＝8.0Hz,J2＝7.5Hz,1H),7.64(t,J1＝7.5Hz,J2＝7.0Hz,1H).7.56-7.51(m,2H),7.43(d,J＝8.5Hz,2H),7.28(d,J＝8.0Hz,1H),7.24(s,1H),7.15(d,J＝7.0Hz,4H),6.84(t,J1＝7.0Hz,J2＝7.5Hz,1H),6.61(d,J＝8.0Hz,1H),6.50(d,J＝8.5Hz,1H),6.40(s,1H),6.36(d,J＝8.5Hz,1H),4.03(s,4H),3.36(m,4H),3.28(s,4H),3.15(s,2H),1.76-1.62(m,12H),1.19(t,J1＝7.0Hz,J2＝7.0Hz,7H)。
核磁共振碳谱13C NMR(300MHz,CDCl3,ppm):δ:185.51,158.45,152.16,140.52,136.53,135.45,134.11,132.92,131.40,130.22,129.86,128.87,128.47,127.38,126.84,126.09,124.13,123.49,121.95,117.60,111.53,108.30,101.01,94.58,90.91,65.55,56.04,47.01,32.26,31.71,31.35,30.77,27.78,26.56,24.70,15.18。
高分辨质谱HRMS,Calcd for,C60H57N7O5S[M+H]+:988.4220。Found:988.4243。[M+Na]+:1010.4040.Found:1010.4061。
由此确认所获得近红外双光子荧光探针CRPM的结构式为：
实施例2
荧光分子CRPM的制备方法为：
氮气保护下，将1,3,3-三甲基-2-亚甲基吲哚啉-罗丹明内酰肼(0.20g,0.35mmol)溶于20mL无水乙腈中，加入4-吗啉基-1,8-萘酰亚胺-苯基异硫氰酸酯(0.15g,0.35mmol)，磁力搅拌下回流反应12h，温度控制在80℃。结束反应，经萃取、干燥、柱色谱提纯，得到CRPM，产率40％。
实施例3
荧光分子CRPM的制备方法为：
氮气保护下，将1,3,3-三甲基-2-亚甲基吲哚啉-罗丹明内酰肼(0.20g,0.35mmol)溶于20mL无水乙腈中，加入4-吗啉基-1,8-萘酰亚胺-苯基异硫氰酸酯(0.15g,0.35mmol)，磁力搅拌下回流反应24h，温度控制在75℃。结束反应，经萃取、干燥、柱色谱提纯，得到CRPM，产率45％。
实施例4
荧光探针分子CRPM在Hg2+诱导下双光子泵浦红光发射：
图1是溶解有荧光分子CRPM的缓冲溶液(缓冲溶液pH为7.4，溶剂为体积比1:1的水和乙醇组成的混合溶剂，荧光分子CRPM的浓度为10-4mol/L)中加入不同金属离子(加入的金属离子浓度为10-4mol/L)的双光子诱导荧光光谱。
在800nm波长飞秒激光激发下，分别向溶解有荧光探针分子CRPM的缓冲溶液(缓冲溶液pH为7.4，溶剂为体积比1:1的水和乙醇组成的混合溶剂，荧光分子CRPM的浓度为10- 4mol/L)中加入不同种类的金属离子Ag+、Li+、Ca2+、Cd2+、Co2+、Cu2+、Fe2+、Ni2+、Zn2+、Mn2+、Cr3+时，探针分子CRPM处于“off”荧光关闭状态，无荧光发射；当加入相同浓度的Hg2+金属离子时，由于Hg2+诱导下的酰胺基硫脲脱硫-环化反应和1,3,3-三甲基-2-亚甲基吲哚啉-罗丹明内酰胺开环的多步串联反应，使得探针分子处于“on”荧光打开状态，CRPM发射极强的双光子泵浦红色荧光，双光子荧光波长位于746nm的近红外波段。CRPM可作为性能优异的近红外波段反应型双光子荧光探针，其灵敏度高，响应时间小于2秒，只在汞离子诱导下产生极强的双光子红色荧光，选择性强。
荧光分子CRPM包含1,3,3-三甲基-2-亚甲基吲哚啉-罗丹明和4-吗啉基-1,8-萘酰亚胺复合荧光团，通过汞离子诱导的酰胺基硫脲脱硫-环化反应及1,3,3-三甲基-2-亚甲基吲哚啉-罗丹明内酰胺的开环反应等多步串联反应可灵敏调控探针分子的双光子荧光性能。荧光分子CRPM可作为近红外波段反应型双光子荧光探针，在近红外双光子荧光成像、双光子荧光传感器、生物荧光分析、荧光标记等领域具有广阔的应用前景。

Claims (6)

1.一种荧光分子，其特征在于，该荧光分子为结构式1表示的化合物：
2.根据权利要求1所述的荧光分子，其特征在于，该荧光分子由1，3，3-三甲基-2-亚甲基吲哚啉-罗丹明酰肼与4-吗啉基-1，8-萘酰亚胺-苯基异硫氰酸酯反应制得；所述1，3，3-三甲基-2-亚甲基吲哚啉-罗丹明酰肼为结构式2表示的化合物，所述4-吗啉基-1，8-萘酰亚胺-苯基异硫氰酸酯为结构式3表示的化合物：
3.权利要求1或2所述的荧光分子的制备方法，其特征在于，在惰性气体保护下，将1，3，3-三甲基-2-亚甲基吲哚啉-罗丹明酰肼与4-吗啉基-1，8-萘酰亚胺-苯基异硫氰酸酯加入到干燥乙腈中，75～80℃下搅拌反应12～24h，提纯，即得所述荧光分子。
4.一种近红外反应型双光子荧光探针，其特征在于，该近红外反应型双光子荧光探针为权利要求1～2中任意一项所述的荧光分子。
5.权利要求4所述的近红外反应型双光子荧光探针在近红外双光子荧光成像、双光子荧光传感器、生物荧光分析或荧光标记中的应用。
6.权利要求4所述的近红外反应型双光子荧光探针在检测Hg2+中的应用。
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