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

被引:12
|
作者
Han, SY [1 ]
Choi, SH [1 ]
Kim, MH [1 ]
Lee, WG [1 ]
Kim, SH [1 ]
Min, YK [1 ]
Kim, BT [1 ]
机构
[1] Korea Res Inst Chem Technol, Bioorgan Sci Div, Taejon 305606, South Korea
关键词
biotin-tagged photoaffinity probe; vascular endothelial; growth factor receptors; ligand-receptor interactions; inhibitor; trifunctional probe;
D O I
10.1016/j.tetlet.2006.02.119
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Novel biotin-tagged photoaffinity probes based on a trifunctional tertiary amine scaffold were synthesized and evaluated as vascular endothelial growth factor receptor-2 (VEGFR-2) inhibitors. Probes 3a-c inhibit VEGF induced proliferation in HUVE cells, with IC50 values of 29.7, 33.3, and 37.7 mu M, respectively. Moreover, we identified the interaction of 3b with VEGFR-2 in photoaffinity labeling experiment using HUVE cells. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2915 / 2919
页数:5
相关论文
共 50 条
  • [41] SYNTHESIS AND BINDING OF NEW POLYFLUORINATED ARYL AZIDES TO ALPHA-CHYMOTRYPSIN - NEW REAGENTS FOR PHOTOAFFINITY-LABELING
    SOUNDARARAJAN, N
    LIU, SH
    SOUNDARARAJAN, S
    PLATZ, MS
    BIOCONJUGATE CHEMISTRY, 1993, 4 (04) : 256 - 261
  • [42] CHEMISTRY OF NATURALLY-OCCURRING POLYAMINES .9. SYNTHESIS OF SPERMIDINE AND SPERMINE PHOTOAFFINITY-LABELING REAGENTS
    NAGARAJAN, S
    GANEM, B
    JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (26): : 5735 - 5737
  • [43] Regulation of PIP2 synthesis by receptor and non-receptor tyrosine kinases
    Weernink, PAO
    Schuy, M
    Schmidt, M
    Jakobs, KH
    NAUNYN-SCHMIEDEBERGS ARCHIVES OF PHARMACOLOGY, 2004, 369 : R57 - R57
  • [44] AEE788, a novel multitargeted inhibitor of ErbB and VEGF receptor family tyrosine kinases:: Preliminary phase 1 results.
    Martinelli, E
    Takimoto, CH
    van Oosterom, AT
    Tabernero, J
    Rowinsky, E
    Schöffski, P
    Huang, J
    Casado, E
    Mita, A
    Dumez, H
    JOURNAL OF CLINICAL ONCOLOGY, 2005, 23 (16) : 201S - 201S
  • [45] Pediatric brain tumors express multiple receptor tyrosine kinases including novel cell adhesion kinases
    Weiner, HL
    Rothman, M
    Miller, DC
    Ziff, EB
    PEDIATRIC NEUROSURGERY, 1996, 25 (02) : 64 - 71
  • [46] Design, synthesis, modeling, biological evaluation and photoaffinity labeling studies of novel series of photoreactive benzamide probes for histone deacetylase 2
    Vaidya, Aditya Sudheer
    Karumudi, Bhargava
    Mendonca, Emma
    Madriaga, Antonett
    Abdelkarim, Hazem
    van Breemen, Richard B.
    Petukhov, Pavel A.
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2012, 22 (15) : 5025 - 5030
  • [47] PHOTOAFFINITY-LABELING OF THE BETA-CELL SULFONYLUREA RECEPTOR USING A NOVEL GLYBURIDE ANALOG
    AGUILARBRYAN, L
    NELSON, DA
    PRIDGEN, MB
    BOYD, AE
    CLINICAL RESEARCH, 1989, 37 (02): : A568 - A568
  • [48] Synthesis of a novel azidocastasterone derivative as a potential photoaffinity label for the brassinosteroid receptor
    Back, TG
    Minksztym, K
    SYNLETT, 1999, (02) : 201 - 203
  • [49] Computational Design of Druglike Allosteric Inhibitors of AXL and MET Receptor Tyrosine Kinases
    Dalafave, D. S.
    Sureshkumar, K.
    BIOPHYSICAL JOURNAL, 2019, 116 (03) : 560A - 560A
  • [50] Vegfrecine, an Inhibitor of VEGF Receptor Tyrosine Kinases Isolated from the Culture Broth of Streptomyces sp.
    Nosaka, Chisato
    Adachi, Hayamitsu
    Sawa, Ryuichi
    Nakae, Koichi
    Atsumi, Sonoko
    Kinoshita, Naoko
    Kubota, Yumiko
    Igarashi, Masayuki
    Sei, Yoshihisa
    Yamaguchi, Kentaro
    Shibuya, Masabumi
    Nishimura, Yoshio
    Akamatsu, Yuzuru
    JOURNAL OF NATURAL PRODUCTS, 2013, 76 (04): : 715 - 719