Design and synthesis of novel photoaffinity reagents for labeling VEGF receptor tyrosine kinases

Tetrahedron Letters

Volumn 47, Issue 17, 2006, Pages 2915-2919

  Han, Sun Young ^a   Choi, Seo Hyun ^a   Kim, Myung Hee ^a   Lee, Woo Ghil ^a   Kim, Seong Hwan ^a   Min, Yong Ki ^a   Kim, Bum Tae ^a  

^a Korea Research Institute of Chemical Technology   (South Korea)

Author keywords

Biotin tagged photoaffinity probe; Inhibitor; Ligand receptor interactions; Trifunctional probe; Vascular endothelial growth factor receptors

Indexed keywords

BIOTIN; PROTEIN TYROSINE KINASE; TERTIARY AMINE; VASCULOTROPIN RECEPTOR; VASCULOTROPIN RECEPTOR 2;

ARTICLE; ENDOTHELIUM CELL; IC 50; PHOTOAFFINITY LABELING; SYNTHESIS;

EID: 33645216699     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.02.119     Document Type: Article

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31. Photoaffinity labeling experiment-HUVEC cells were homogenized in buffer consisting of 10 mM Tris-HCl (pH 7.5), 150 mM NaCl, 0.05% (v/v) Tween 20, 1 mM PMSF, and one protease inhibitor cocktail tablet (Roche, Germany) at 4°C and centrifuged at 10,000g for 15 min. The BCA protein assay Kit (Pierce, IL) was used to determine the concentration of protein in the supernatant. Proteins (100 μg in 50 μl) were incubated with 3b (100 μM) at 4°C for 2 h, and placed on an ice tray under a UV light source (BIO-LINK with 5 × 8 W tubes, 254 nm, Vilber Lourmat, France) twice for 2 min. Compound 3b was first dissolved in dimethyl sulfoxide (DMSO; Sigma, MO), and then diluted with homogenate buffer, so that the final DMSO concentration was 1% in the samples. Irradiated protein samples (20 μg) were mixed with sample buffer (100 mM Tris-HCl, 2% sodium dodecyl sulfate, 1% 2-mercaptoethanol, 2% glycerol, 0.01% bromophenol blue, pH 7.6), incubated at 50°C for 10 min, and loaded onto 8% polyacrylamide gels. Electrophoresis was performed using the Mini Protean 3 Cell (Bio-Rad). Proteins separated on the gels were transferred onto nitrocellulose membrane (Scheicher & Schnell BioScience, Germany), and the membrane was incubated in blocking buffer (10 mM Tris-HCl, pH 7.5, 150 mM NaCl, 0.1% Tween 20, 3% nonfat dry milk). The membrane was incubated for 2 h at room temperature with 1:1000 diluted primary antibody. Horse radish peroxidase (HRP)-conjugated antibody against VEGFR-2 and antibodies against streptavidin and biotin were purchased from Santa Cruz Biotechnology Inc. (CA) and Calbiochem (Merck Biosciences, Korea), respectively. After washing three times for 15 min with blocking buffer, and developed with SuperSignal West Femto Maximum Sensitivity Substrate (Pierce). The immunoreactivity was detected using LAS-3000 luminescent image analyzer (Fuji Photo Film Co., Ltd, Japan).
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