3-Pyrrolyl BODIPY的绿色生物合成、光物理性质及应用研究

doi:10.6023/cjoc202304028

有机化学 ›› 2024, Vol. 44 ›› Issue (1): 216-223.DOI: 10.6023/cjoc202304028 上一篇下一篇

研究论文

3-Pyrrolyl BODIPY的绿色生物合成、光物理性质及应用研究

马翠云^a, 罗海澜^a^,^*(), 张福华^a, 郭丹^a, 陈树兴^b, 王飞^a^,^*()

a 漯河医学高等专科学校河南省营养与健康工程研究中心河南漯河 462002
b 中原食品实验室河南漯河 462333

收稿日期:2023-04-20 修回日期:2023-07-11 发布日期:2023-09-15
作者简介:
^†共同第一作者.
基金资助:
2020年中央引导地方科技发展专项; 河南省科技攻关(232102310335); 漯河医学高等专科学校科技(2015-S-LMC013); 漯河医学高等专科学校科技(2020-LYZKYZD007); 漯河医学高等专科学校科技(2021LYZKJXM017); 漯河医学高等专科学校科技(2022KJZD11); 漯河医学高等专科学校科技(2019-LYZTD003)

Green Biosynthesis, Photophysical Properties and Application of 3-Pyrrolyl BODIPY

Cuiyun Ma^a, Hailan Luo^a(), Fuhua Zhang^a, Dan Guo^a, Shuxing Chen^b, Fei Wang^a()

a Henan Engineering Research Center of Nutrition & Health, Luohe Medical College, Luohe, Henan 462002
b Food Laboratory of Zhongyuan, Luohe, Henan 462333

Received:2023-04-20 Revised:2023-07-11 Published:2023-09-15
Contact: *E-mail: xiaohailuo1224@163.com; E-mail: whovering@lhmc.edu.cn
About author:
^†The authors contributed equally to this work.
Supported by:
2020 Central Government and Guiding Local Science and Technology Development, the Science; Technology Project of Henan Province(232102310335); Project of Luohe Medical College(2015-S-LMC013); Project of Luohe Medical College(2020-LYZKYZD007); Project of Luohe Medical College(2021LYZKJXM017); Project of Luohe Medical College(2022KJZD11); Project of Luohe Medical College(2019-LYZTD003)

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摘要/Abstract

3-吡咯基氟硼二吡咯(3-Pyrrolyl BODIPYs)荧光染料的绿色合成与应用是值得进一步研究的重要问题. 到目前为止, 在所有的合成方法中, 都无法避免使用有毒的吡咯类有机化合物作为反应底物. 本研究使用一种微生物源天然色素, 沙雷氏菌y2的次级代谢产物灵菌红素, 来合成目标化合物. 利用灵菌红素天然的吡咯基甲川基结构, 合成了一种新的3-pyrrolyl BODIPY. 光物理性质实验表明其具有荧光成像的性能, 然后使用SW480细胞进行细胞染色探索. 激光共聚焦显微镜荧光成像结果显示其可在三通道中发射出不同强度的荧光, Z-stack结果揭示其红色通道与绿色通道中细胞穿透性可以达到266 μm. 细胞毒性实验也说明3-pyrrolyl BODIPY具有良好的生物相容性, 是一种值得开发的荧光染料.

关键词: 沙雷氏菌y2, 灵菌红素, 绿色生物合成, 3-吡咯基氟硼二吡咯, 荧光成像

The green synthesis and application of fluorescent dyes 3-pyrrolyl BODIPYs (dipyrromethene boron difluorides) are important issues worthy of further research. Up till now, toxic pyrrole organic compounds cannot be avoided as substrates in all synthetic methods. In this study, the target compound was synthesized by using prodigiosin—the secondary metabolites of Serratia marcescens y2, a natural pigment of microbial origin. A new 3-pyrrolyl BODIPY was synthesized from the natural pyrrole dimethyl subunit structure of prodigiosin. After the experiment of photophysical properties showed that it has the performance of fluorescence imaging, SW480 cells was used for fluorescent staining test. The fluorescence imaging results of Confocal laser microscopy indicated 3-pyrrolyl BODIPY can fluoresce in the three channels. The Z-stack results revealed that the cell penetration of 3-pyrrolyl BODIPY could reach 226 μm in blue and red channels. The results of SW480 live cyto- toxicity test also illustrated that 3-pyrrolyl BODIPY has good biocompatibility and is worth developing as a fluorescent dye.

Key words: Serratia Marcescens y2, prodigiosin, green biosynthesis, 3-pyrrolyl BODIPY, fluorescence imaging

引用此文

马翠云, 罗海澜, 张福华, 郭丹, 陈树兴, 王飞. 3-Pyrrolyl BODIPY的绿色生物合成、光物理性质及应用研究[J]. 有机化学, 2024, 44(1): 216-223.

Cuiyun Ma, Hailan Luo, Fuhua Zhang, Dan Guo, Shuxing Chen, Fei Wang. Green Biosynthesis, Photophysical Properties and Application of 3-Pyrrolyl BODIPY[J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 216-223.

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图/表 9

图1. BODIPY核心、pyrroyl BODIPY核心、二吡咯甲川与BF3的反应中间体和目标化合物3-pyrrolyl BODIPYs的结构

Figure 1. Chemical structures of BODIPY core, pyrryl BODIPY core, the intermediate in the reaction between diphyrrolidine and BF3, and target compound 3-pyrryl BODIPYs

图式1. 3-Pyrrolyl BODIPY的绿色合成与应用

Scheme 1. Green synthesis and applications of 3-pyrrolyl BODIPY

图2. 试管I中PG(曲线a)与试管II上层溶液(曲线b)的最大吸收峰(A)和Serratia marcescen y2次级代谢产物的质谱图(B)

Figure 2. Absorption spectra of PG from tube I (curve a) and the upper layer of tube Ⅱ (curve b) (A), and MS analysis of the extracted product from the host cells of Serratia marcescens y2 (B)

图3. 3-Pyrrolyl BODIPYs的NOESY谱的局部放大图

Figure 3. Partial enlarged NOESY spectrum of 3-pyrrolyl BODIPYs

图4. 3-Pyrrolyl BODIPYs的紫外-可见光谱图(A)和3-pyrrolyl BODIPYs的荧光发射光谱(激发波长为550 nm) (B)

Figure 4. Absorption spectra of 3-pyrrolyl BODIPY (A) and fluorescence spectra of 3-pyrrolyl BODIPY (λex=550 nm) (B)

图5. 3-Pyrrolyl BODIPY对SW480细胞存活率的影响

Figure 5. Effects of 3-pyrrolyl BODIPY on the cell viability of SW480 cells

图6. 3-Pyrrolyl BODIPY在SW480细胞中的共聚焦荧光图像

Figure 6. Confocal fluorescence images of 3-pyrrolyl BODIPY in SW480 cells λex=405 nm, λem=410~513 nm (A); λex=555 nm, λem=566~697 nm (B); λex=488 nm, λem=493~556 nm (C); white field (D); merge (E)

图7. 3-Pyrrolyl BODIPY与DAPI在SW480细胞中双染的共聚焦荧光图像

Figure 7. Confocal fluorescence images of 3-pyrrolyl BODIPY and DAPI in SW480 cells λex=405 nm, λem=410~513 nm (A); λex=555 nm, λem=566~697 nm (B); λex=488 nm, λem=493~556 nm (C); white field (D); merge (E)

图8. 蓝色通道下3-pyrrolyl BODIPY在SW480细胞中Z-stacks CLSM(激光扫描共聚焦显微镜)图像

Figure 8. CLSM (Confocal laser scanning microscope) images of Z-stacks of 3-pyrrolyl BODIPYs in SW480 in blue channel

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3-Pyrrolyl BODIPY的绿色生物合成、光物理性质及应用研究

Green Biosynthesis, Photophysical Properties and Application of 3-Pyrrolyl BODIPY

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