Progress of Fluorescent Bio-probe Based on Water-Soluble Boron-dipyrromethene
- Corresponding author: Meng Shuxian, msxmail@tju.edu.cn Feng Yaqing, yqfeng@tju.edu.cn
	            Citation:
	            
		            Lu Bowei, Meng Shuxian, Feng Yaqing. Progress of Fluorescent Bio-probe Based on Water-Soluble Boron-dipyrromethene[J]. Chinese Journal of Organic Chemistry,
							;2018, 38(2): 350-362.
						
							doi:
								10.6023/cjoc201706018
						
					
				
					 
				
	        
 
	                
				Jung, D.; Min, K.; Jung, J. Mol. BioSyst. 2013, 9, 862.
												 doi: 10.1039/c2mb25422k
											
										
				Boens, N.; Leen, V.; Dehaen, W. Chem. Soc. Rev. 2012, 41, 1130.
												 doi: 10.1039/C1CS15132K
											
										
				Lavis, L.; Raines, R. ACS Chem. Biol. 2008, 3, 142.
												 doi: 10.1021/cb700248m
											
										
				Vos, D. W.; Pardoen, J. A.; Van, K. J. Recl. Trav. Chim. Pays-Bas 1977, 96, 306.
										
				Qin, W. W.; Barush, M. Chem. Phys. Chem. 2005, 6, 2343.
												 doi: 10.1002/(ISSN)1439-7641
											
										
				Wories, H.; Koek, J.; Lodder, G. Recl. Trav. Chim. Pays-Bas 1985, 104, 288.
										 
				Nierth, A.; Kobitski, A.; Nienhaus, G.; Jaschke A. J. Am. Chem. Soc. 2010, 132, 2646.
												 doi: 10.1021/ja9084397
											
										
				Yao, H.; Zhu, X.; Guo, X. Anal. Chem. 2016, 88, 9014.
												 doi: 10.1021/acs.analchem.6b01532
											
										
				Li, P.; Fang, L.; Zhou, H.; Zhang, W.; Wang, X.; Li, N.; Zhong, H.; Tang, B. Chem. -Eur. J. 2011, 17, 10520..
												 doi: 10.1002/chem.201101327
											
										
				Zhang, J.; Bao, X.; Zhou, J. Biosens. Bioelectron. 2016, 85, 164.
												 doi: 10.1016/j.bios.2016.05.005
											
										
				Zhu, H.; Fan, J.; Mu, H. Sci. Rep. 2016, 6, 35627.
												 doi: 10.1038/srep35627
											
										
				Kamiya, M.; Johnsson, K. Anal. Chem. 2010, 82, 6472.
												 doi: 10.1021/ac100741t
											
										
				Matsui, K.; Umezawa, Y.; Shindo, T.; Fujii, D.; Citterio, K.; Suzuki, K. Chem. Commun. 2011, 47, 10407.
												 doi: 10.1039/c1cc14045k
											
										
				Khoerunnisa; Mazrad, Z.; In, I.; Park, S. Biosens. Bioelectron. 2017, 90, 394.
												 doi: 10.1016/j.bios.2016.12.013
											
										
				Atilgan, S.; Ekmekci, Z.; Dogan, A. L.; Guc, D.; Akkaya, E. U. Chem. Commun. 2006, 4398.
										 
				He, H.; Lo, P.; Yeung, S.; Fong, W.; Dennis, K. J. Med. Chem. 2011, 54, 3097.
												 doi: 10.1021/jm101637g
											
										
				Turan, I.; Cakmak, F.; Yildirim, D. Chem. -Eur. J. 2014, 20, 16088.
												 doi: 10.1002/chem.v20.49
											
										
				Niu, L.; Guan, Y.; Chen, Y. J. Am. Chem. Soc. 2012, 134, 18928.
												 doi: 10.1021/ja309079f
											
										
				Atilgan, S.; Ozdemir, T.; Akkaya, E. U. Org. Lett. 2008, 10, 4065.
												 doi: 10.1021/ol801554t
											
										
				Ojida, A.; Sakamoto, T.; Inoue, M. J. Am. Chem. Soc. 2009, 131, 6543.
												 doi: 10.1021/ja9008369
											
										
				Moriarty, R.; Martin, A.; Adamson, K. J. Microsc. 2014, 25, 204.
										 
				Chen, J.; Zhang, H.; Guo, X. Anal. Bioanal. Chem. 2013, 405, 7447.
												 doi: 10.1007/s00216-013-7177-6
											
										
				Vegesna, G.; Sripathi, S.; Zhang, J.; Zhu, S.; He, W.; Luo, F.; Jahng, W.; Frost, M.; Liu, H. J. ACS Appl. Mater. Interfaces 2013, 5, 4107.
												 doi: 10.1021/am303247s
											
										
				Xiong, H.; Kos, P.; Yan, Y.; Zhou, K.; Miller, J.; Elkassih, S.; Siegwart, D. Bioconjugate Chem. 2016, 27, 1737.
												 doi: 10.1021/acs.bioconjchem.6b00242
											
										
				Zhu, S.; Zhang, J.; Janjanam, J. Anal. Chim. Acta 2013, 758, 138.
												 doi: 10.1016/j.aca.2012.10.026
											
										
				Sui, B.; Tang, S.; Woodward, A. Eur. J. Org. Chem. 2016, 2851.
										
				Isik, M.; Ozdemir, T.; Turan, I. Org. Lett. 2013, 15, 216.
												 doi: 10.1021/ol303306s
											
										
				Meltola, N.; Wahlroos, R.; Soini, A. J. Fluoresc. 2004, 14, 635.
												 doi: 10.1023/B:JOFL.0000039350.94256.53
											
										
				Kamkaew, A.; Fu, N.; Cai, W. ACS Med. Chem. Lett. 2017, 8, 179.
												 doi: 10.1021/acsmedchemlett.6b00368
											
										
				Liu, S.; Li, D.; Zhang, Z. Chem. Commun. 2014, 50, 7371.
												 doi: 10.1039/c4cc01411a
											
										
				Myochin, T.; Hanaoka, K.; Komatsu, T.; Terai, T.; Nagano, T. J. Am. Chem. Soc. 2012, 134, 13730.
												 doi: 10.1021/ja303931b
											
										
				Worsfold, O.; Voelcker, N.; Nishiya, T. Langmuir 2006, 22, 7078.
												 doi: 10.1021/la060121y
											
										
				Namkung, W.; Padmawar, P.; Mills, A.; Verkman, S. J. Am. Chem. Soc. 2008, 130, 7794.
												 doi: 10.1021/ja8014499
											
										
				Murtagh, J.; Frimannsson, D. O.; O'Shea, D. F. Org. Lett. 2009, 11, 5386.
												 doi: 10.1021/ol902140v
											
										
				Cheng, T.; Xu, Y.; Zhang, S. J. Am. Chem. Soc. 2008, 130, 16160.
												 doi: 10.1021/ja806928n
											
										
				Jiao, L.; Li, J.; Zhang, S. New J. Chem. 2009, 33, 1888.
												 doi: 10.1039/b906441a
											
										
				Dodani, S.; He, Q.; Chang, C. J. Am. Chem. Soc. 2009, 131, 18020.
												 doi: 10.1021/ja906500m
											
										
				Lee, H.; Bae, D.; Park, J. Angew. Chem., Int. Ed. 2009, 48, 1239.
												 doi: 10.1002/anie.200804714
											
										
				Son, H.; Lee, H.; Lim, J. Chem. -Eur. J. 2010, 16, 11549.
												 doi: 10.1002/chem.v16:38
											
										
				Lee, H.; Son, H.; Lim, J. Analyst 2010, 135, 2022.
												 doi: 10.1039/c0an00129e
											
										
				Yamada, Y.; Tomiyama, Y.; Morita, A. ChemBioChem 2008, 9, 853.
												 doi: 10.1002/(ISSN)1439-7633
											
										
				Liu, Y.; Pei, Q.; Chen, L.; Li, Z.; Xie, Z. J. Mater. Chem. B 2016, 4, 2332.
										 
				Vernekar, S.; Hallaq, H.; Clarkson, G. J. Med. Chem. 2010, 53, 2324.
												 doi: 10.1021/jm901827x
											
										
				Lan, Y.; Xiao, K.; Wu, Y.; Chen, Q. Spectrochim. Acta, Part A 2017, 177, 28.
												 doi: 10.1016/j.saa.2017.01.030
											
										
				Wang, C.; Song, X.; Chen, L.; Xiao, Y. Biosens. Bioelectron. 2017, 91, 313.
												 doi: 10.1016/j.bios.2016.11.018
											
										
				Saha, S.; Agarwalla, H.; Gupta, H. Dalton Trans. 2013, 42, 15097.
												 doi: 10.1039/c3dt51744f
											
										
				Wang, K.; Xiao, Y.; Wang, Y.; Feng, Y.; Chen, C.; Zhang, J.; Zhang, Q.; Meng, S.; Wang, Z.; Yang, H. Sci. Rep. 2016, 6, 23061.
												 doi: 10.1038/srep23061
											
										
				Pashow, K.; Rocca, J.; Xie, Z.; Tran, S.; Lin, W. J. Am. Chem. Soc. 2009, 131, 14261.
												 doi: 10.1021/ja906198y
											
										
				Fan, G.; Lin, Y.; Yang, L. Chem. Commun. 2015, 51, 12447.
												 doi: 10.1039/C5CC04757A
											
										
				Huang, L.; Li, Z.; Zhao, Y. J. Am. Chem. Soc. 2016, 138, 14586.
												 doi: 10.1021/jacs.6b05390
											
										
				He, H.; Zhang, J.; Xie, Y. Mol. Pharmaceutics 2016, 13, 4013.
												 doi: 10.1021/acs.molpharmaceut.6b00705
											
										
				Sharker, S.; Kang, E.; Shin, C. J. Appl. Polym. Sci. 2016, 43791.
										 
				Lv, H.; Zhang, X.; Wang, S. Analyst 2017, 142, 603.
												 doi: 10.1039/C6AN02705A
											
										
				Shen, B. X.; Qian, Y. Chin. J. Org. Chem. 2016, 36, 774(in Chinese).
										 
				Loudet, A.; Burgess, K. Chem. Rev. 2007, 107, 4891.
												 doi: 10.1021/cr078381n
											
										
				Cheng, T.; Wang, T.; Zhu, W. Org. Lett. 2011, 13, 3656.
												 doi: 10.1021/ol201305d
											
										
				Cakmak, Y.; Kolemen, S.; Duman, S. Angew. Chem., Int. Ed. 2011, 50, 11937.
												 doi: 10.1002/anie.v50.50
											
										
				Alamudi, S.; Satapathy, R.; Kim, J. Nat. Commun. 2016, 7, 11964.
												 doi: 10.1038/ncomms11964
											
										
 
						
						
						
	                Qiang HU , Zhiqi CHEN , Zhong CHEN , Xu WANG , Weina WU . Pyridinium-chalcone-based ClO- fluorescent probe: Preparation and biological imaging applications. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1789-1795. doi: 10.11862/CJIC.20250086
Jinlong YAN , Weina WU , Yuan WANG . A simple Schiff base probe for the fluorescent turn-on detection of hypochlorite and its biological imaging application. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1653-1660. doi: 10.11862/CJIC.20240154
Lina Feng , Guoyu Jiang , Xiaoxia Jian , Jianguo Wang . Application of Organic Radical Materials in Biomedicine. University Chemistry, 2025, 40(4): 253-260. doi: 10.12461/PKU.DXHX202405171
Jian Li , Yu Zhang , Rongrong Yan , Kaiyuan Sun , Xiaoqing Liu , Zishang Liang , Yinan Jiao , Hui Bu , Xin Chen , Jinjin Zhao , Jianlin Shi . Highly Efficient, Targeted, and Traceable Perovskite Nanocrystals for Photoelectrocatalytic Oncotherapy. Acta Physico-Chimica Sinica, 2025, 41(5): 100042-0. doi: 10.1016/j.actphy.2024.100042
Xiaoyu YANG , Yejun ZHANG , Yu ZOU , Hongchao YANG , Jiang JIANG , Qiangbin WANG . Research progress of inorganic X-ray nanoscintillators. Chinese Journal of Inorganic Chemistry, 2025, 41(10): 1929-1952. doi: 10.11862/CJIC.20250122
Feng Lu , Tao Wang , Qi Wang . Preparation and Characterization of Water-Soluble Silver Nanoclusters: A New Design and Teaching Practice in Materials Chemistry Experiment. University Chemistry, 2025, 40(4): 375-381. doi: 10.12461/PKU.DXHX202406005
Jinghan ZHANG , Guanying CHEN . Progress in the application of rare-earth-doped upconversion nanoprobes in biological detection. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2335-2355. doi: 10.11862/CJIC.20240249
Yanxi LIU , Mengjia XU , Haonan CHEN , Quan LIU , Yuming ZHANG . A fluorescent-colorimetric probe for peroxynitrite-anion-imaging in living cells. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1112-1122. doi: 10.11862/CJIC.20240423
Lixing ZHANG , Yaowen WANG , Xu HAN , Junhong ZHOU , Jinghui WANG , Liping LI , Guangshe LI . Research progress in the synthesis of fluorine-containing perovskites and their derivatives. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1689-1701. doi: 10.11862/CJIC.20250007
Xinyi Hong , Tailing Xue , Zhou Xu , Enrong Xie , Mingkai Wu , Qingqing Wang , Lina Wu . Non-Site-Specific Fluorescent Labeling of Proteins as a Chemical Biology Experiment. University Chemistry, 2024, 39(4): 351-360. doi: 10.3866/PKU.DXHX202310010
Xin MA , Ya SUN , Na SUN , Qian KANG , Jiajia ZHANG , Ruitao ZHU , Xiaoli GAO . A Tb2 complex based on polydentate Schiff base: Crystal structure, fluorescence properties, and biological activity. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1347-1356. doi: 10.11862/CJIC.20230357
Benhua Wang , Chaoyi Yao , Yiming Li , Qing Liu , Minhuan Lan , Guipeng Yu , Yiming Luo , Xiangzhi Song . 一种基于香豆素氟离子荧光探针的合成、表征及性能测试——“科研反哺教学”在有机化学综合实验教学中的探索与实践. University Chemistry, 2025, 40(6): 201-209. doi: 10.12461/PKU.DXHX202408070
Siyi ZHONG , Xiaowen LIN , Jiaxin LIU , Ruyi WANG , Tao LIANG , Zhengfeng DENG , Ao ZHONG , Cuiping HAN . Targeting imaging and detection of ovarian cancer cells based on fluorescent magnetic carbon dots. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1483-1490. doi: 10.11862/CJIC.20240093
Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373
Pengli GUAN , Renhu BAI , Xiuling SUN , Bin LIU . Trianiline-derived aggregation-induced emission luminogen probe for lipase detection and cell imaging. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1817-1826. doi: 10.11862/CJIC.20250058
. . Chinese Journal of Inorganic Chemistry, 2024, 40(12): 0-0.
Yingpeng ZHANG , Xingxing LI , Yunshang YANG , Zhidong TENG . A pyrazole-based turn-off fluorescent probe for visual detection of hydrazine. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1301-1308. doi: 10.11862/CJIC.20250064
Yuting DU , Jing YUAN , Peiyao DENG . Synthesis and application of a fluorescent probe for the detection of reduced glutathione. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1331-1337. doi: 10.11862/CJIC.20240461
Haitang WANG , Yanni LING , Xiaqing MA , Yuxin CHEN , Rui ZHANG , Keyi WANG , Ying ZHANG , Wenmin WANG . Construction, crystal structures, and biological activities of two LnⅢ3 complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1474-1482. doi: 10.11862/CJIC.20240188
Xiaowei TANG , Shiquan XIAO , Jingwen SUN , Yu ZHU , Xiaoting CHEN , Haiyan ZHANG . A zinc complex for the detection of anthrax biomarker. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1850-1860. doi: 10.11862/CJIC.20240173