含羟基氧杂蒽荧光染料的合成及其荧光成像应用
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摘要
近年来,氧杂蒽类荧光染料具有很多优点而被广泛应用。由于近红外荧光染料用于荧光成像,具有光损伤小、组织穿透性大和背景荧光干扰小的优点,设计合成了具有羟基的1-(2-羟基-4-二乙氨-苯基)-氧杂蒽类荧光染料(NIR1)和1-(6-羟基-萘基-2)-氧杂蒽类荧光染料(NIR2)。通过核磁共振谱和质谱确认了荧光染料的结构。利用紫外-可见吸收光谱和荧光光谱对其光谱性能进行研究,结果表明,NIR-1和NIR-2最大吸收波长分别为642 nm和607 nm,最大发射波长分别为748 nm和752 nm。最后,对含羟基氧杂蒽荧光染料用于细胞和活体的荧光标记成像进行研究,结果表明NIR-1具有良好的细胞和活体荧光标记成像效果。
In recent years,xanthene-based organic fluorescent dyes have been widely used because of their many advantages.Due to the low optical damage to biological samples,strong tissue penetration,and low background fluorescence interference of near-infrared( NIR) light,NIR dyes have been used for fluorescence imaging.1-( 2-hydroxy-4-diethylammonia-phenyl)-oxanthracene fluorescent dyes( NIR1) and 1-( 6-hydroxy-naphthyl-2)-oxanthracene fluorescent dyes( NIR2) were synthesized with hydroxyl group.Meanwhile,their structures were confirmed by1 HNMR and HR-MS. The photophysical properties of xanthene NIR-1 and NIR-2 were investigated by UV-Vis spectroscopy and fluorescence spectroscopy.The maximum absorption wavelength of NIR-1 is642 nm,and the maximum emission wavelength is 748 nm.The maximum absorption wavelength of NIR-2 is 607 nm,and the maximum emission wavelength is 752 nm.At last,the fluorescence labeling effect of xanthene derivatives for imaging was tested.The results indicated that the NIR-1 can be used for fluorescence imaging in living cells and in vivo.
In recent years,xanthene-based organic fluorescent dyes have been widely used because of their many advantages.Due to the low optical damage to biological samples,strong tissue penetration,and low background fluorescence interference of near-infrared( NIR) light,NIR dyes have been used for fluorescence imaging.1-( 2-hydroxy-4-diethylammonia-phenyl)-oxanthracene fluorescent dyes( NIR1) and 1-( 6-hydroxy-naphthyl-2)-oxanthracene fluorescent dyes( NIR2) were synthesized with hydroxyl group.Meanwhile,their structures were confirmed by1 HNMR and HR-MS. The photophysical properties of xanthene NIR-1 and NIR-2 were investigated by UV-Vis spectroscopy and fluorescence spectroscopy.The maximum absorption wavelength of NIR-1 is642 nm,and the maximum emission wavelength is 748 nm.The maximum absorption wavelength of NIR-2 is 607 nm,and the maximum emission wavelength is 752 nm.At last,the fluorescence labeling effect of xanthene derivatives for imaging was tested.The results indicated that the NIR-1 can be used for fluorescence imaging in living cells and in vivo.
引文
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[3]杨冰,李瑛,徐创霞,等.有机荧光材料研究进展[J].化学研究与应用,2003,15(1):11-16.
[4]孙丹,袁雪梅,徐海军,等.BODIPY类近红外荧光染料的研究进展[J].无机化学学报,2015,31(8):1 467-1 479.
[5]郭炜,张洪星,刘景.近红外罗丹明荧光染料[J].山西大学学报(自然科学版),2017,40(3):590-595.
[6]XU Xiao-he,PHADUNGSAK P,JI Hai-feng.A fluorescent sensor with a large Stoke's shift[J]. Imag. Sci. Photochem.,2011,29(5):364-371.
[7]RURACK K,SPIELES M.Fluorescence quantum yields of a series of red and near-infrared dyes emitting at 600~1 000 nm[J].Anal.Chem.,2011,83(4):1 232-1 242.
[8]YUAN Lin,LIN Wei-ying,ZHAO Sheng,et al.A unique approachto development of near-infrared fluorescent sensors for in vivo imaging[J]. J. Am. Chem. Soc.,2012,134(32):13 510-13 523.
[9]黄阳阳,王梦嘉,厍梦尧,等.基于氧杂蒽结构可控官能化的荧光探针研究新进展[J].有机化学,2014,34(1):1-25.
[10]袁跃华,殷强锋,冯峰,等.新罗丹明类荧光探针的合成及对铜(Ⅱ)的检测[J].分析实验室,2018,37(4):373-377.
[11]田怡,陈稼轩,王红艳,等.罗丹明型Cu2+比色探针的合及识别[J].化学试剂,2017,39(12):1 338-1 340.
[12]国飞,张修石.近红外荧光成像的新进展[J].实用肿瘤学杂志,2008,22(2):198-200.
[13]刘政,孙丽宁,施利毅,等.近红外稀土荧光在功能材料领域的研究进展[J].化学进展,2011,23(1):53-164.
[14]王晓驰,常刚,曹瑞军,等.近红外荧光染料的结构、性质及生物荧光成像应用[J].化学进展,2015,27(7):794-805.
[15]NIU Guang-le,LIU Wei-min,ZHOU Bing-jiang,et al.Deep-red and near-infrared xanthene dyes for rapid live cell imaging[J]. J. Org. Chem.,2016,81(17):7 393-7 399.
[16]管小余.罗丹明及其衍生物的合成和光谱性质的研究应用[D].湖南:湖南大学,2014.