Citation:
Hui Chen, Hui Wang, Xiao-Jun Qin, Chen Chen, Lu Feng, Lai-Zhong Chen, Lu-Pei Du, Min-Yong Li. A bestatin-based fl uorescent probe for aminopeptidase N cell imaging[J]. Chinese Chemical Letters,
;2015, 26(5): 513-516.
doi:
10.1016/j.cclet.2015.01.023
-
Aminopeptidase N (APN) is an important drug target and biomarker for various tumors. The current work characterizes a novel APN-targeted fluorescent probe (Bes-Green, 2) that manifests comparable inhibitory activity with Bestatin. This probe has capacity of tightly binding to the APN for imaging endogenous APN in living human ovarian clear cell carcinoma cells (ES-2) and has potential application in biological study of cellular APN.
-
Keywords:
- Aminopeptidase N,
- Bestatin,
- Cell imaging,
- Fluorescent probe
-
-
-
[1]
[1] L.Z. Chen, W. Sun, J. Li, et al., The first ratiometric fluorescent probes for aminopeptidaseN cell imaging, Org. Biomol. Chem. 11 (2013) 378-382.
-
[2]
[2] J. Dixon, L. Kaklamanis, H. Turley, et al., Expression of aminopeptidase-n (CD 13) innormal tissues and malignant neoplasms of epithelial and lymphoid origin, J. Clin.Pathol. 47 (1994) 43-47.
-
[3]
[3] A.T. Look, R.A. Ashmun, L.H. Shapiro, S.C. Peiper, Human myeloid plasma membraneglycoprotein CD13 (gp150) is identical to aminopeptidase N, J. Clin. Invest.83 (1989) 1299-1307.
-
[4]
[4] X.P. Zhang, W.F. Xu, Aminopeptidase N (APN/CD13) as a target for anti-canceragent design, Curr. Med. Chem. 15 (2008) 2850-2865.
-
[5]
[5] I. Saiki, J. Yoneda, I. Azuma, et al., Role of aminopeptidase N (CD13) in tumor-cellinvasion and extracellular matrix degradation, Int. J. Cancer 54 (1993) 137-143.
-
[6]
[6] H. Tsukamoto, K. Shibata, H. Kajiyama, et al., Aminopeptidase N (APN)/CD13inhibitor, Ubenimex, enhances radiation sensitivity in human cervical cancer,BMC Cancer 8 (2008) 74.
-
[7]
[7] R. Pasqualini, E. Koivunen, R. Kain, et al., Aminopeptidase N is a receptor fortumor-homing peptides and a target for inhibiting angiogenesis, Cancer Res. 60(2000) 722-727.
-
[8]
[8] F. Curnis, A. Sacchi, L. Borgna, et al., Enhancement of tumor necrosis factor alphaantitumor immunotherapeutic properties by targeted delivery to aminopeptidaseN (CD13), Nat. Biotechnol. 18 (2000) 1185-1190.
-
[9]
[9] A.H. Negussie, J.L. Miller, G. Reddy, et al., Synthesis and in vitro evaluation of cyclicNGR peptide targeted thermally sensitive liposome, J. Control. Release 143 (2010)265-273.
-
[10]
[10] L.A. Plesniak, B. Salzameda, H. Hinderberger, et al., Structure and activity ofCPNGRC: a modified CD13/APN peptidic homing motif, Chem. Biol. Drug Des.75 (2010) 551-562.
-
[11]
[11] G. Pathuri, A.F. Hedrick, B.C. Disch, et al., Synthesis and evaluation of novel Tc-99m labeled probestin conjugates for imaging APN/CD13 expression in vivo,Bioconjug. Chem. 23 (2012) 115-124.
-
[12]
[12] S. Lee, J. Xie, X. Chen, Peptides and peptide hormones for molecular imaging anddisease diagnosis, Chem. Rev. 110 (2010) 3087-3111.
-
[13]
[13] H. Kobayashi, M. Ogawa, R. Alford, P.L. Choyke, Y. Urano, New strategies forfluorescent probe design in medical diagnostic imaging, Chem. Rev. 110 (2010)2620-2640.
-
[14]
[14] E. Soini, I. Hemmilä, Fluoroimmunoassay: present status and key problems, Clin.Chem. 25 (1979) 353-361.
-
[15]
[15] T.T. Dai, L. Liu, D.L. Tao, et al., Influence of Gd doping on the absolute quantumefficiency and lifetime of EuxGd1-x(TTA)3phens, Chin. Chem. Lett. 25 (2014)892-896.
-
[16]
[16] L.Z. Chen, J.J. Mou, Y.Y. Xu, H. Fang, W.F. Xu, Design, synthesis and activity study ofaminopeptidase N targeted 3-amino-2-hydroxy-4-phenyl-butanoic acid derivatives,Drug Discov. Ther. 5 (2011) 61-65.
-
[17]
[17] Y. Ma, Q.Y. Tang, J. Zhu, L.H. Wang, C. Yao, Fluorescent and thermal properties ofsiloxane-polyurethanes based on 1, 8-naphthalimide, Chin. Chem. Lett. 25 (2014)680-686.
-
[18]
[18] M.B. Harbut, G. Velmourougane, G. Reiss, R. Chandramohanadas, D.C. Greenbaum,Development of bestatin-based activity-based probes for metallo-aminopeptidases,Bioorg. Med. Chem. Lett. 18 (2008) 5932-5936.
-
[19]
[19] A. von Wallbrunn, J. Waldeck, C. Hö ltke, et al., In vivo optical imaging of CD13/APN-expression in tumor xenografts, J. Biomed. Opt. 13 (2008) 011007.
-
[20]
[20] Z. Zhang, H. Harada, K. Tanabe, et al., Aminopeptidase N/CD13 targeting fluorescentprobes: synthesis and application to tumor cell imaging, Peptides 26 (2005)2182-2187.
-
[21]
[21] W. Zhang, Z. Ma, L. Du, M. Li, Design strategy for photoinduced electron transferbasedsmall-molecule fluorescent probes of biomacromolecules, Analyst 139(2014) 2641-2649.
-
[22]
[22] L. Chen, W. Sun, W. Li, et al., The first ratiometric fluorescent probe for aminopeptidaseN, Anal. Methods 4 (2012) 2661-2663.
-
[23]
[23] A. Hahnenkamp, M. Schafers, C. Bremer, C. Holtke, Design and synthesis of smallmoleculefluorescent photoprobes targeted to aminopeptdase N (APN/CD13) foroptical imaging of angiogenesis, Bioconjug. Chem. 24 (2013) 1027-1038.
-
[24]
[24] L.Z. Chen, L.P. Du, M.Y. Li, The first inhibitor-based fluorescent imaging probe foraminopeptidase N, Drug Discov. Ther. 7 (2013) 124-125.
-
[25]
[25] H. Umezawa, T. Aoyagi, H. Suda, M. Hamada, T. Takeuchi, Bestatin, an inhibitor ofaminopeptidase B, produced by actinomycetes, J. Antibiot. 29 (1976) 97-99.
-
[26]
[26] W. Xu, Q. Li, Progress in the development of aminopeptidase N (APN/CD13)inhibitors, Curr. Med. Chem. Anticancer Agents 5 (2005) 281-301.
-
[1]
-
-
-
[1]
Chuan-Zhi Ni , Ruo-Ming Li , Fang-Qi Zhang , Qu-Ao-Wei Li , Yuan-Yuan Zhu , Jie Zeng , Shuang-Xi Gu . A chiral fluorescent probe for molecular recognition of basic amino acids in solutions and cells. Chinese Chemical Letters, 2024, 35(10): 109862-. doi: 10.1016/j.cclet.2024.109862
-
[2]
Huamei Zhang , Jingjing Liu , Mingyue Li , Shida Ma , Xucong Zhou , Aixia Meng , Weina Han , Jin Zhou . Imaging polarity changes in pneumonia and lung cancer using a lipid droplet-targeted near-infrared fluorescent probe. Chinese Chemical Letters, 2024, 35(12): 110020-. doi: 10.1016/j.cclet.2024.110020
-
[3]
Han-Min Wang , Yan-Chen Li , Lu-Lu Sun , Ming-Ye Tang , Jia Liu , Jiahao Cai , Lei Dong , Jia Li , Yi Zang , Hai-Hao Han , Xiao-Peng He . Protein-encapsulated long-wavelength fluorescent probe hybrid for imaging lipid droplets in living cells and mice with non-alcoholic fatty liver. Chinese Chemical Letters, 2024, 35(11): 109603-. doi: 10.1016/j.cclet.2024.109603
-
[4]
Boran Cheng , Lei Cao , Chen Li , Fang-Yi Huo , Qian-Fang Meng , Ganglin Tong , Xuan Wu , Lin-Lin Bu , Lang Rao , Shubin Wang . Fluorine-doped carbon quantum dots with deep-red emission for hypochlorite determination and cancer cell imaging. Chinese Chemical Letters, 2024, 35(6): 108969-. doi: 10.1016/j.cclet.2023.108969
-
[5]
Zhixue Liu , Haiqi Chen , Lijuan Guo , Xinyao Sun , Zhi-Yuan Zhang , Junyi Chen , Ming Dong , Chunju Li . Luminescent terphen[3]arene sulfate-activated FRET assemblies for cell imaging. Chinese Chemical Letters, 2024, 35(9): 109666-. doi: 10.1016/j.cclet.2024.109666
-
[6]
Qian Ren , Xue Dai , Ran Cen , Yang Luo , Mingyang Li , Ziyun Zhang , Qinghong Bai , Zhu Tao , Xin Xiao . A cucurbit[8]uril-based supramolecular phosphorescent assembly: Cell imaging and sensing of amino acids in aqueous solution. Chinese Chemical Letters, 2024, 35(12): 110022-. doi: 10.1016/j.cclet.2024.110022
-
[7]
Yudi Cheng , Xiao Wang , Jiao Chen , Zihan Zhang , Jiadong Ou , Mengyao She , Fulin Chen , Jianli Li . A near-infrared fluorescent probe for visualizing transformation pathway of Cys/Hcy and H2S and its applications in living system. Chinese Chemical Letters, 2024, 35(5): 109156-. doi: 10.1016/j.cclet.2023.109156
-
[8]
Tao Liu , Xuwei Han , Xueyi Sun , Weijie Zhang , Ke Gao , Runan Min , Yuting Tian , Caixia Yin . An activated fluorescent probe to monitor NO fluctuation in Parkinson’s disease. Chinese Chemical Letters, 2025, 36(3): 110170-. doi: 10.1016/j.cclet.2024.110170
-
[9]
Fan Zheng , Runsha Xiao , Shuai Huang , Zhikang Chen , Chen Lai , Anyao Bi , Heying Yao , Xueping Feng , Zihua Chen , Wenbin Zeng . Accurate visualization colorectal cancer by monitoring viscosity variations with a novel mitochondria-targeted fluorescent probe. Chinese Chemical Letters, 2025, 36(2): 109876-. doi: 10.1016/j.cclet.2024.109876
-
[10]
Zhixiao Xiong , Shanni Qiu , Yuyu Wang , Houna Duan , Yi Xiao , Yufang Xu , Weiping Zhu , Xuhong Qian . Photocalibrated NO release from the zinc ion fluorescent probe based on naphthalimide and its application in living cells. Chinese Chemical Letters, 2025, 36(4): 110002-. doi: 10.1016/j.cclet.2024.110002
-
[11]
Chuanfeng Fan , Jian Gao , Yingkai Gao , Xintong Yang , Gaoning Li , Xiaochun Wang , Fei Li , Jin Zhou , Haifeng Yu , Yi Huang , Jin Chen , Yingying Shan , Li Chen . A non-peptide-based chymotrypsin-targeted long-wavelength emission fluorescent probe with large Stokes shift and its application in bioimaging. Chinese Chemical Letters, 2024, 35(10): 109838-. doi: 10.1016/j.cclet.2024.109838
-
[12]
Lei Shen , Hongmei Liu , Ming Jin , Jinchao Zhang , Caixia Yin , Shuxiang Wang , Yutao Yang . “Three-in-one” strategy of trifluoromethyl regulated blood-brain barrier permeable fluorescent probe for peroxynitrite and antiepileptic evaluation of edaravone. Chinese Chemical Letters, 2024, 35(10): 109572-. doi: 10.1016/j.cclet.2024.109572
-
[13]
Jia-Mei Qin , Xue Li , Wei Lang , Fu-Hao Zhang , Qian-Yong Cao . An AIEgen nano-assembly for simultaneous detection of ATP and H2S. Chinese Chemical Letters, 2024, 35(6): 108925-. doi: 10.1016/j.cclet.2023.108925
-
[14]
Brandon Bishop , Shaofeng Huang , Hongxuan Chen , Haijia Yu , Hai Long , Jingshi Shen , Wei Zhang . Artificial transmembrane channel constructed from shape-persistent covalent organic molecular cages capable of ion and small molecule transport. Chinese Chemical Letters, 2024, 35(11): 109966-. doi: 10.1016/j.cclet.2024.109966
-
[15]
Xu Qu , Pengzhao Wu , Kaixuan Duan , Guangwei Wang , Liang-Liang Gao , Yuan Guo , Jianjian Zhang , Donglei Shi . Self-calibrating probes constructed on a unique dual-emissive fluorescence platform for the precise tracking of cellular senescence. Chinese Chemical Letters, 2024, 35(12): 109681-. doi: 10.1016/j.cclet.2024.109681
-
[16]
Jiajia Lv , Jie Gao , Hongyu Li , Zeli Yuan , Nan Dong . Rational design of hydroxytricyanopyrrole-based probes with high affinity and rapid visualization for amyloid-β aggregates in vitro and in vivo. Chinese Chemical Letters, 2024, 35(5): 108940-. doi: 10.1016/j.cclet.2023.108940
-
[17]
Chao Liu , Chao Jia , Shi-Xian Gan , Qiao-Yan Qi , Guo-Fang Jiang , Xin Zhao . A luminescent one-dimensional covalent organic framework for organic arsenic sensing in water. Chinese Chemical Letters, 2024, 35(11): 109750-. doi: 10.1016/j.cclet.2024.109750
-
[18]
Yunkang Tong , Haiqiao Huang , Haolan Li , Mingle Li , Wen Sun , Jianjun Du , Jiangli Fan , Lei Wang , Bin Liu , Xiaoqiang Chen , Xiaojun Peng . Cooperative bond scission by HRP/H2O2 for targeted prodrug activation. Chinese Chemical Letters, 2024, 35(12): 109663-. doi: 10.1016/j.cclet.2024.109663
-
[19]
Quan Zhang , Shunjie Xing , Jingqian Han , Li Feng , Jianchun Li , Zhaosheng Qian , Jin Zhou . Organic pollutant sensing for human health based on carbon dots. Chinese Chemical Letters, 2025, 36(1): 110117-. doi: 10.1016/j.cclet.2024.110117
-
[20]
Hui Zhang , Rong Feng , Wanyi Yu , Hongbei Wei , Tianhong Wu , Peng Zhang , Wenhai Bian , Xin Li , Di Gao , Guojun Weng , Zhe Yang , Tony D. James , Xiaolong Sun . Evaluating the global thiols redox state in living cells using a reducing sulfur species responsive fluorescence switching platform. Chinese Chemical Letters, 2025, 36(4): 110528-. doi: 10.1016/j.cclet.2024.110528
-
[1]
Metrics
- PDF Downloads(0)
- Abstract views(621)
- HTML views(18)