The first ratiometric fluorescent probe for aminopeptidase N

被引:27
作者
Chen, Laizhong [1 ]
Sun, Wei [1 ]
Li, Wenhua [1 ]
Li, Jing [1 ]
Du, Lupei [1 ]
Xu, Wenfang [1 ]
Fang, Hao [1 ]
Li, Minyong [1 ]
机构
[1] Shandong Univ, Sch Pharm, Dept Med Chem, Key Lab Chem Biol Nat Prod MOE, Jinan 250012, Shandong, Peoples R China
关键词
IN-VIVO; CELLS; INHIBITORS; TARGET; APN/CD13; DESIGN;
D O I
10.1039/c2ay25556a
中图分类号
O65 [分析化学];
学科分类号
070302 ; 081704 ;
摘要
The current work describes the design and synthesis of the first ratiometric fluorescent probe, Ala-PABA-7HC, for the detection of aminopeptidase N (APN) at both the enzymatic and the cellular level. Upon addition of APN to the solution of Ala-PABA-7HC in PBS or culture medium, the maximum emission peak experienced a red shift from 390 nm to 450 nm, and the ratio of fluorescence intensity (I-450/I-390) (lambda(ex) = 330 nm) significantly increased from 0.26 to 3.05 (R = 11.7-fold) in 15 min.
引用
收藏
页码:2661 / 2663
页数:3
相关论文
共 19 条
[1]   Aminopeptidase-N/CD13 (EC 3.4.11.2) inhibitors: Chemistry, biological evaluations, and therapeutic prospects [J].
Bauvois, B ;
Dauzonne, D .
MEDICINAL RESEARCH REVIEWS, 2006, 26 (01) :88-130
[2]   Synthesis and biological evaluation of novel flavone-8-acetic acid derivatives as reversible inhibitors of aminopeptidase N/CD13 [J].
Bauvois, B ;
Puiffe, ML ;
Bongui, JB ;
Paillat, S ;
Monneret, C ;
Dauzonne, D .
JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (18) :3900-3913
[3]   Design, synthesis and activity study of aminopeptidase N targeted 3-amino-2-hydroxy-4-phenyl-butanoic acid derivatives [J].
Chen, Laizhong ;
Mou, Jiajia ;
Xu, Yingying ;
Fang, Hao ;
Xu, Wenfang .
DRUG DISCOVERIES AND THERAPEUTICS, 2011, 5 (02) :61-65
[4]   Enhancement of tumor necrosis factor a antitumor immunotherapeutic properties by targeted delivery to aminopeptidase N (CD13) [J].
Curnis, F ;
Sacchi, A ;
Borgna, L ;
Magni, F ;
Gasparri, A ;
Corti, A .
NATURE BIOTECHNOLOGY, 2000, 18 (11) :1185-1190
[5]   Aminopeptidase Fingerprints, an Integrated Approach for Identification of Good Substrates and Optimal Inhibitors [J].
Drag, Marcin ;
Bogyo, Matthew ;
Ellman, Jonathan A. ;
Salvesen, Guy S. .
JOURNAL OF BIOLOGICAL CHEMISTRY, 2010, 285 (05) :3310-3318
[6]   Novel and highly sensitive fluorescent assay for leucine aminopeptidases [J].
Huang, Huazhang ;
Tanaka, Hiromasa ;
Hammock, Bruce D. ;
Morisseau, Christophe .
ANALYTICAL BIOCHEMISTRY, 2009, 391 (01) :11-16
[7]  
Inagaki Y, 2010, BIOSCI TRENDS, V4, P56
[8]  
Laube F, 2007, ANTICANCER RES, V27, P2047
[9]   Dark quenched matrix metalloproteinase fluorogenic probe for imaging osteoarthritis development in vivo [J].
Lee, Seulki ;
Park, Kyeongsoon ;
Lee, Seung-Young ;
Ryu, Ju Hee ;
Park, Jong Woong ;
Ahn, Hyung Jun ;
Kwon, Ick Chan ;
Youn, In-Chan ;
Kim, Kwangmeyung ;
Choi, Kuiwon .
BIOCONJUGATE CHEMISTRY, 2008, 19 (09) :1743-1747
[10]   A comparative study of the self-immolation of para-aminobenzylalcohol and hemithioaminal-based linkers in the context of protease-sensitive fluorogenic probes [J].
Meyer, Yves ;
Richard, Jean-Alexandre ;
Delest, Bruno ;
Noack, Pauline ;
Renard, Pierre-Yves ;
Romieu, Anthony .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (08) :1777-1780