Activity-based probe for specific photoaffinity labeling γ-aminobutyric acid B (GABAB) receptors on living cells: Design, synthesis, and biological evaluation

Journal of Medicinal Chemistry

Volumn 51, Issue 11, 2008, Pages 3057-3060

  Li, Xin ^b   Cao, Jian Hua ^a   Li, Ying ^a   Rondard, Philippe ^c   Zhang, Yang ^a   Yi, Ping ^a   Liu, Jian Feng ^a   Nan, Fa Jun ^b  

^a HUAZHONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b Shanghai Jiao Tong University Affiliated Sixth People s Hospital   (China)

^c INSTITUT DE GÉNOMIQUE FONCTIONNELLE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

4 AMINOBUTYRIC ACID B RECEPTOR;

ANIMAL CELL; ARTICLE; CELL STRAIN HEK293; CHO CELL; CONTROLLED STUDY; HUMAN; HUMAN CELL; LIGAND BINDING; NONHUMAN; PHOTOAFFINITY LABELING; PROTEIN BINDING; PROTEIN EXPRESSION; PROTEIN FUNCTION; PROTEIN LOCALIZATION; RECEPTOR BINDING; SYNTHESIS;

ANIMALS; BENZOATES; BORON COMPOUNDS; CELL LINE; CRICETINAE; CRICETULUS; DIAZOMETHANE; DRUG DESIGN; HUMANS; ORGANOPHOSPHORUS COMPOUNDS; PHOTOAFFINITY LABELS; PROTEIN SUBUNITS; RECEPTORS, GABA-B; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 44949244902     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm800140f     Document Type: Article

References (32)

1. Bettler, B.; Kaupmann, K.; Bowery, N. GABAB receptors: drugs meet clones. Curr. Opin. Neurobiol. 1998, 8, 345-350.
2. Bettler, B.; Tiao, J. Y.-H,. Molecular diversity, trafficking and subcellular localization of GABAB receptors. Pharmacol. Ther. 2006, 110, 533-543.
3. Harayama, N.; Shibuya, I.; Tanaka, K.; Kabashima, N.; Ueta, Y.; Yamashita, H. Inhibition of N- and P/Q-type calcium channels by postsynaptic GABAB receptor activation in rat supraoptic neurons. J. Physiol. 1998, 509, 371-383.
4. Luscher, C.; Jan, L. Y.; Stoffel, M.; Malenka, R. C.; Nicoll, R. A. G. protein-coupled inwardly rectifying K+ channels (GIRKs) mediate postsynaptic but not presynaptic transmitter actions in hippocampal neurons. Neuron 1997, 19, 687-695.
5. Schuler, V.; Luscher, C.; Blanchet, C.; Klix, N.; Sansig, G.; Klebs, K.; Schmutz, M.; Heid, J.; Gentry, C.; Urban, L.; Fox, A.; Spooren, W.; Jaton, A. L.; Vigouret, J.; Pozza, M.; Kelly, P. H.; Mosbacher, J.; Froestl, W.; Kaslin, E.; Korn, R.; Bischoff, S.; Kaupmann, K.; Putten, H. V. D.; Bettler, B. Epilepsy, hyperalgesia, impaired memory, and loss of pre- and postsynaptic GABAB responses in mice lacking GABAB(1). Neuron. 2001, 31, 47-58.
6. Leaney, J. L.; Tinker, A. The role of members of the pertussis toxin-sensitive family of G proteins in coupling receptors to the activation of the G protein-gated inwardly rectifying potassium channel. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 5651-5656.
7. Odagaki, Y.; Koyama, T. Identification of Gα subtype(s) involved in γ-aminobutyric acid B receptor-mediated high-affinity guanosine triphosphatase activity in rat cerebral cortical membranes. Neurosci. Lett. 2001, 297, 137-141.
8. Simonds, W. F. G protein regulation of adenylate cyclase. Trends Pharmacol. Sci. 1999, 20, 66-73.
9. Tu, H.; Rondard, P.; Xu, C.; Bertaso, F.; Cao, F.; Zhang, X.; J.; Pin, J.-P.; Liu, J. Dominant role of GABAB 2 and Gβγ for GABAB receptor-mediated-ERK1/2/CREB pathway in cerebellar neurons. Cell. Signalling 2007, 19, 1996-2002.
10. Pin, J.-P.; Kniazeff, J.; Binet, V.; Liu, J.; Maurel, D.; Galvez, T.; Duthey, B.; Havlickova, M.; Blahos, J.; Prézeau, L.; Rondard, P. Activation mechanism of the heterodimeric GABAB receptor. Biochem. Pharmacol. 2004, 68, 1565-1572.
11. Galvez, T.; Duthey, B.; Kniazeff, J.; Blahos, J.; Rovelli, G.; Bettler, B.; Prézeau, L.; Pin, J.-P. Allosteric interactions between GB1 and GB2 subunits are required for optimal GABAB receptor function. EMBO J. 2001, 20, 2152-2159.
12. Pagano, A.; Rovelli, G.; Mosbacher, J.; Lohmann, T.; Duthey, B.; Stauffer, D.; Ristig, D.; Schuler, V.; Meigel, I.; Lampert, C.; Stein, T.; Prézeau, L.; Blahos, J.; Pin, J.-P.; Froestl, W.; Kuhn, R.; Heid, J.; Kaupmann, K.; Bettler, B. C-Terminal interaction is essential for surface trafficking but not for heteromeric assembly of GABAB receptors. J. Neurosci. 2001, 21, 1189-1202.
13. Kniazeff, J.; Galvez, T.; Labesse, G.; Pin, J.-P. No ligand binding in the GB2 subunit of the GABAB receptor is required for activation and allosteric interaction between the subunits. J. Neurosci. 2002, 22, 7352-7361.
14. Liu, J.; Maurel, D.; Etzol, S.; Brabet, I.; Ansanay, H.; Pin, J.-P.; Rondard, P. Molecular determinants involved in the allosteric control of agonist affinity in the GABAB receptor by the GABAB2 subunit. J. Biol. Chem. 2004, 279, 15824-15830.
15. (a) Kozikowski, A. P.; Kotoula, M.; Ma, D.; Boujrad, N.; Tuc̈kmantel, W.; Papadopoulos, V. Synthesis and biology of a 7-nitro-2,1,3-benzoxadiazol-4- yl derivative of 2-phenylindole-3-acetamide: a fluorescent probe for the peripheral-type benzodiazepine receptor. J. Med. Chem. 1997, 40, 2435-2439.
16. (b) Taliani, S.; Simorini, F.; Sergianni, V.; La Motta, C.; Da Settimo, F.; Cosimelli, B.; Abignente, E.; Greco, G.; Novellino, E.; Rossi, L.; Gremigni, V.; Spinetti, F.; Chelli, B.; Martini, C. New fluorescent 2- phenylindolglyoxylamide derivatives as probes targeting the peripheral-type benzodiazepine receptor: design, synthesis, and biological evaluation. J. Med. Chem. 2007, 50, 404-407.
17. (c) Cha, J. H.; Zou, M. F.; Adkins, E. M.; Rasmussen, S. G. F.; Loland, C. J.; Schoenenberger, B.; Gether, U.; Newman, A. H. Rhodamine-labeled 2β-carbomethoxy-3β-(3,4-dichlorophenyl) tropane analogues as high-affinity fluorescent probes for the dopamine transporter. J. Med. Chem. 2005, 48, 7513-7516.
18. Evans, M. J.; Cravatt, B. F. Mechanism-based profiling of enzyme families. Chem. Rev. 2006, 106, 3279-3301.
19. (a) Liu, Y.; Patricelli, M. P.; Cravatt, B. F. Activity-based protein profiling: the serine hydrolases. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 14694-14699.
20. (b) Adam, G. C.; Cravatt, B. F.; Sorensen, E. J. Proteomic profiling of mechanistically distinct enzyme classes using a common chemotype. Nat. Biotechnol. 2002, 20, 805-809.
21. (c) Saghatelian, A.; Jessani, N.; Joseph, A.; Humphrey, M.; Cravatt, B. F. Activity-based probes for the proteomic profiling of metalloproteases. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 10000-10005.
22. Kaupmann, K.; Huggel, K.; Heid, J.; Flor, P. J.; Bischoff, S.; Mickel, S. J.; McMaster, G.; Angst, C.; Bittiger, H. Expression cloning of GABAB receptors uncovers similarity to metabotropic glutamate receptors. Nature 1997, 386, 239-246.
23. Hatanaka, Y.; Sadakane, Y. Photoaffinity labeling in drug discovery and developments: chemical gateway for entering proteomic frontier. Curr. Top. Med. Chem. 2002, 2, 271-288.
24. Karolin, J.; Johansson, L. B. A.; Strandberg, L.; Ny, T. Fluorescence and absorption spectroscopic properties of dipyrrometheneboron difluoride (BODIPY) derivatives in liquids, lipid membranes, and proteins. J. Am. Chem. Soc. 1994, 116, 7801-7806.
25. Belley, M.; Sullivan, R.; Reeves, A.; Evans, J.; O'Neill, G.; Ng, G. Y. K. Synthesis of the nanomolar photoaffinity GABAB receptor ligand CGP 71872 reveals diversity in the tissue distribution of GABAB receptor forms. Bioorg. Med. Chem. 1999, 7, 2697-2704.
26. Li, Z. G.; Mintzer, E.; Bittman, R. First synthesis of free cholesterol-BODIPY conjugates. J. Org. Chem. 2006, 71, 1718-1721.
27. Hatanaka, Y.; Hashimoto, M.; Kurihara, H.; Nakayama, H.; Kanaoka, Y. A novel family of aromatic diazirines for photoaffinity labeling. J. Org. Chem. 1994, 59, 383-387.
28. Kolb, H. C.; Sharpless, K. B. The growing impact of click chemistry on drug discovery. Drug Discovery Today 2003, 8, 1128-1137.
29. Schneckenburger, H. Total internal reflection fluorescence microscopy: technical innovations and novel applications. Curr. Opin. Biotechnol. 2005, 16, 13-18.
30. Gross, L. A.; Baird, G. S.; Hoffman, R. C.; Baldridge, K. K.; Tsien, R. Y. The structure of the chromophore within DsRed, a red fluorescent protein from coral. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 11990-11995.
31. (a) Shreder, K. R.; Wong, M. S.; Nomanbhoy, T.; Leventhal, P. S.; Fuller, S. R. Synthesis of AX7593, a quinazoline-derived photoaffinity probe for EGFR. Org. Lett. 2004, 6, 3715-3718.
32. (b) Zoffmann, S.; Turcatti, G.; Galzi, J. L.; Dahl, M.; Chollet, A. Synthesis and characterization of fluorescent and photoactivatable MIP-1α ligands and interactions with chemokine receptors CCR1 and CCR5. J. Med. Chem. 2001, 44, 215-222.