A Novel BODIPY Quaternary Ammonium Salt-Based Fluorescent Probe: Synthesis, Physical Properties, and Live-Cell Imaging

被引:16
|
作者
Deng, Peng [1 ]
Xiao, Fuyan [2 ]
Wang, Zhou [3 ]
Jin, Guofan [2 ]
机构
[1] Nantong Univ, Affiliated Danyang Hosp, Peoples Hosp Danyang, Zhenjiang, Jiangsu, Peoples R China
[2] Jiangsu Univ, Sch Pharm, Zhenjiang, Jiangsu, Peoples R China
[3] Panzhihua Univ, Coll Vanadium & Titanium, Panzhihua, Peoples R China
来源
FRONTIERS IN CHEMISTRY | 2021年 / 9卷
关键词
BODIPY; quaternary ammonium salt; HeLa cells; in vitro imaging; in vivo imaging; EMISSION;
D O I
10.3389/fchem.2021.650006
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The development of biological fluorescent probes is of great significance to the field of cancer bio-imaging. However, most current probes within the bulky hydrophobic group have limited application in aqueous medium and restricted imaging under physiological conditions. Herein, we proposed two efficient molecules to study their physical properties and imaging work, and the absorption and fluorescence intensity were collected with varying ions attending in aqueous medium. We enhance the water solubility through the quaternization reaction and form a balance between hydrophilic and hydrophobicity with dipyrrome-theneboron difluoride (BODIPY) fluorophore. We introduced pyridine and dimethylaminopyridine (DMAP) by quaternization and connected the BODIPY fluorophore by ethylenediamine. The final synthesized probes have achieved ideal affinity with HeLa cells (human cervical carcinoma cell line) in live-cell imaging which could be observed by Confocal Microscope. The probes also have a good affinity with subcutaneous tumor cells in mice in in vivo imaging, which may make them candidates as oncology imaging probes.
引用
收藏
页数:9
相关论文
共 50 条
  • [1] Quaternary ammonium salt-based chromogenic and fluorescent chemosensors for fluoride ions
    Luxami, Vijay
    Sharma, Nidhi
    Kumar, Subodh
    TETRAHEDRON LETTERS, 2008, 49 (27) : 4265 - 4268
  • [2] NitroxylFluor: A Thiol-Based Fluorescent Probe for Live-Cell Imaging of Nitroxyl
    Pino, Nicholas W.
    Davis, Jerome, III
    Yu, Zhengxin
    Chan, Jefferson
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (51) : 18476 - 18479
  • [3] A Turn-On Fluorescent Probe for Live-Cell Imaging of Biothiols
    Hong, Jong-Ah
    Kim, Min-Ji
    Eo, Jinny
    Lee, Jiyoun
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2018, 39 (04) : 425 - 426
  • [4] Synthesis and properties of quaternary ammonium salt fluorescent brighteners
    Cao, Chengbo
    Han, Hongbin
    Wang, Deyi
    Zhang, Changqiao
    Zhu, Yanli
    Huagong Xuebao/Journal of Chemical Industry and Engineering (China), 2006, 57 (12): : 3010 - 3015
  • [5] Rapid detection of aspartic acid and glutamic acid in water by BODIPY-Based fluorescent probe: Live-cell imaging and DFT studies
    Guria, Subhajit
    Ghosh, Avijit
    Manna, Kalipada
    Pal, Abhishek
    Adhikary, Arghya
    Adhikari, Susanta
    DYES AND PIGMENTS, 2019, 168 : 111 - 122
  • [6] Advances in Synthetic Fluorescent Probe Labeling for Live-Cell Imaging in Plants
    Yagi, Noriyoshi
    Yoshinari, Akira
    Iwatate, Ryu J.
    Isoda, Reika
    Frommer, Wolf B.
    Nakamura, Masayoshi
    PLANT AND CELL PHYSIOLOGY, 2021, 62 (08) : 1259 - 1268
  • [7] Synthesis of fluorescent MOFs: live-cell imaging and sensing of a herbicide
    Mohanty, Aurobinda
    Singh, Udai P.
    Butcher, R. J.
    Das, Neeladrisingha
    Roy, Partha
    CRYSTENGCOMM, 2020, 22 (26): : 4468 - 4477
  • [8] Synthesis and application of fluorescent Ras proteins for live-cell imaging
    Reents, R
    Wagner, M
    Schlummer, S
    Kuhlmann, J
    Waldmann, H
    CHEMBIOCHEM, 2005, 6 (01) : 86 - 94
  • [9] A hydrazone-based turn-on fluorescent probe for peroxynitrite detection and live-cell imaging
    Kim, Sudeok
    Ko, Chang Woo
    Lim, Taeho
    Yoo, Soyeon
    Ha, Hye Jin
    Kang, Seo-Young
    Kang, Seungyoon
    Cho, Steve K.
    Han, Min Su
    DYES AND PIGMENTS, 2019, 171
  • [10] 1,8-Naphthalimide-Substituted BODIPY Dyads: Synthesis, Structure, Properties, and Live-Cell Imaging
    Poddar, Madhurima
    Sharma, Vinay
    Mobin, Shaikh M.
    Misra, Rajneesh
    CHEMISTRY-AN ASIAN JOURNAL, 2018, 13 (19) : 2881 - 2890