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

doi:10.6023/cjoc202304028

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (1): 216-223.DOI: 10.6023/cjoc202304028 Previous Articles Next Articles

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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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Abstract

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

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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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Fig. & Tab. 9

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

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

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)

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

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

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

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)

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)

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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