Synthesis and characterization of high-affinity 4,4-difluoro-4-bora-3a,4a- diaza-s-indacene-labeled fluorescent ligands for human β-adrenoceptors

Journal of Medicinal Chemistry

Volumn 54, Issue 19, 2011, Pages 6874-6887

  Baker, Jillian G ^a   Adams, Luke A ^a   Salchow, Karolina ^a   Mistry, Shailesh N ^a   Middleton, Richard J ^a,b   Hill, Stephen J ^a   Kellam, Barrie ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

^b CellAura Technologies Ltd   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

4,4 DIFLUORO 4 BORA 3A,4A DIAZA S INDACENE; ALPRENOLOL; BETA ADRENERGIC RECEPTOR; CIMATEROL; DIETHYLENE GLYCOL; FENOTEROL; FLUOROCHROME; LIGAND; PINDOLOL DERIVATIVE; PROPRANOLOL DERIVATIVE; SALBUTAMOL; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; BINDING AFFINITY; BINDING SITE; CONTROLLED STUDY; FLUORESCENCE SPECTROSCOPY; LIGAND BINDING; NONHUMAN; RECEPTOR BINDING; SYNTHESIS;

ADRENERGIC BETA-AGONISTS; ADRENERGIC BETA-ANTAGONISTS; ALPRENOLOL; ANIMALS; BORON COMPOUNDS; CHO CELLS; CRICETINAE; CRICETULUS; DRUG PARTIAL AGONISM; FLUORESCENT DYES; GENES, REPORTER; HUMANS; LIGANDS; MICROSCOPY, CONFOCAL; PINDOLOL; PROPRANOLOL; RADIOLIGAND ASSAY; RECEPTORS, ADRENERGIC, BETA-1; RECEPTORS, ADRENERGIC, BETA-2; RECEPTORS, ADRENERGIC, BETA-3; SINGLE-CELL ANALYSIS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 80053905598     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm2008562     Document Type: Article

References (56)

1. Bilski, A. J.; Halliday, S. E.; Fitzgerald, J. D.; Wale, J. L. The pharmacology of a beta 2-selective adrenoceptor antagonist (ICI 118,551) J. Cardiovasc. Pharmacol. 1983, 5, 430-437 (Pubitemid 13080761)
2. Jacoby, E.; Bouhelal, R.; Gerspacher, M.; Seuwen, K. The 7 TM G-protein coupled receptor target family ChemMedChem 2006, 1, 760-782 (Pubitemid 44384538)
3. Bylund, D. B.; Bond, R. A.; Eikenburg, D. C.; J. Hieble, P. J.; Hills, R.; Minneman, K. P.; Parra, S. Beta-adrenoceptors. http://www.iuphar-db.org/ DATABASE/FamilyMenuForward?familyId=4.
4. Michel, M. C.; Insel, P. A. Adrenergic receptors in clinical medicine. In The Receptors: The Adrenergic Receptors: In the 21st Century; Perez, D. M., Ed.; Humana Press: New York, 2007; pp 129-147.
5. Powe, D. G.; Voss, M. J.; Zänker, K. S.; Habashy, H. O.; Green, A. R.; Ellis, I. O.; Entschladen, F. Beta-blocker drug therapy reduces secondary cancer formation in breast cancer and improves cancer specific survival Oncotarget 2010, 1, 628-638
6. Sloan, E. K.; Priceman, S. J.; Cox, B. F.; Yu, S.; Pimente, M. A.; Tangkanangnukul, V.; Arevalo, J. M. C.; Morizono, K.; Karanikolas, B. D. W.; Wu, L.; Sood, A. K.; Cole, S. W. The sympathetic nervous system induces a metastatic switch in primary breast cancer Cancer Res. 2010, 70, 7042-7052
7. Leopoldo, M.; Lacivita, E.; Berardi, F.; Perrone, R. Developments in fluorescent probes for receptor research Drug Discovery Today 2009, 14, 706-712
8. Rajagopal, S.; Rajagopal, K.; Leftkowitz, R. J. Teaching old receptors new tricks: Biasing seven-transmembrane receptors Nat. Rev. Drug Discov. 2010, 9, 373-386
9. Kenakin, T.; Miller, L. J. Seven transmembrane receptors as shapeshifting proteins: The impact of allosteric modulation and functional selectivity on new drug discovery Pharmacol. Rev. 2010, 62, 265-304
10. Baker, J. G.; Hill, S. J. Multiple GPCR conformations and signalling pathways: Implications for antagonist affinity estimates Trends Pharmacol. Sci. 2007, 28, 374-381 (Pubitemid 47087964)
11. Williams, C.; Hill, S. J. GPCR signalling: Understanding the pathway to successful drug discovery Methods Mol. Biol. 2009, 552, 39-50
12. Hill, S. J. G-protein-coupled receptors: Past, present and future Br. J. Pharmacol. 2006, 147, S27-S37
13. Patel, H. H.; Murray, F.; Insel, P. A. Caveolae as organizers of pharmacologically relevant signal transduction molecules Annu. Rev. Pharmacol. Toxicol. 2008, 48, 359-391 (Pubitemid 351738158)
14. Tobin, A. B.; Butcher, A. J.; Kong, K. C. Location, location, location. Site-specific GPCR phosphorylation offers a mechanism for cell-type specific signalling Trends Pharmacol. Sci. 2008, 29, 413-420
15. May, L. T.; Self, T. J.; Briddon, S. J.; Hill, S. J. The effect of allosteric modulators on the kinetics of agonist-G protein-coupled receptor interactions in single living cells Mol. Pharmacol. 2010, 78, 511-523
16. Cordeaux, Y.; Briddon, S. J.; Alexander, S. P. H.; Kellam, B.; Hill, S. J. Agonist-occupied A3 adenosine receptors exist within heterogeneous complexes in membrane microdomains of individual living cells FASEB J. 2008, 22, 850-860 (Pubitemid 351350620)
17. Baker, J. G.; Hill, S. J.; Summers, R. J. Evolution of β-blockers: From anti-anginal drugs to ligand-directed signalling Trends Pharmacol. Sci. 2011, 32, 227-234
18. Lahav, M.; Melamed, E.; Dafna, Z.; Atlas, D. Localization of beta receptors in the anterior segment of the rat eye by a fluorescent analogue of propranolol Invest. Ophthalmol. Vis. Sci. 1978, 17, 645-651 (Pubitemid 8364260)
19. Melamed, E.; Lahav, M.; Atlas, D. Histochemical evidence for beta-adrenergic receptors in the rat spinal cord Brain Res. 1976, 116, 511-515
20. Melamed, E.; Lahav, M.; Atlas, D. Beta-adrenergic receptors in rat myocardium: Direct detection by a new fluorescent beta-blocker Experientia 1976, 32, 1387-1389
21. Melamed, E.; Lahav, M.; Atlas, D. Direct localisation of beta-adrenoceptor sites in rat cerebellum by a new fluorescent analogue of propranolol Nature 1976, 261, 420-422
22. Melamed, E.; Lahav, M.; Atlas, D. Beta-adrenergic receptors in rat cerebral cortex: Histochemical localization by a fluorescent beta-blocker Brain Res. 1977, 128, 379-384 (Pubitemid 8119311)
23. Atlas, D.; Melamed, E. Direct mapping of beta-adrenergic receptors in the rat central nervous system by a novel fluorescent beta-blocker Brain Res. 1978, 150, 377-385 (Pubitemid 8374929)
24. Henis, Y. I.; Hekman, M.; Elson, E. L.; Helmreich, E. J. Lateral motion of beta receptors in membranes of cultured liver cells Proc. Natl. Acad. Sci. U. S. A. 1982, 79, 2907-2911 (Pubitemid 12032341)
25. Rademaker, B.; Kramer, K.; van Ingen, H.; Kranendonk, M.; Timmerman, H. Non-specific binding of the fluorescent beta-adrenergic receptor probe alprenolol-NBD J. Receptor Res. 1985, 5, 121-131 (Pubitemid 15237499)
26. Rademaker, B.; Kramer, K.; Bast, A.; Timmerman, H. Irreversible binding of the fluorescent beta-adrenoceptor probes alprenolol-NBD and pindolol-NBD to specific and non-specific binding sites Res. Commun. Chem. Pathol. Pharmacol. 1988, 60, 147-159
27. Hess, A. Visualization of beta-adrenergic receptor sites with fluorescent beta-adrenergic blocker probes, or autofluorescent granules? Brain Res. 1979, 160, 533-538 (Pubitemid 9106074)
28. Barnes, P.; Koppel, H.; Lewis, P.; Hutson, C.; Blair, I.; Dollery, C. A fluorescent analogue of propranolol does not label beta-adrenoceptor sites Brain Res. 1980, 181, 209-213 (Pubitemid 10159389)
29. Heithier, H.; Hallmann, D.; Boege, F.; Reiländer, H.; Dees, C.; Jaeggi, K. A.; Arndt-Jovin, D.; Jovin, T. M.; Helmreich, E. J. Synthesis and properties of fluorescent beta-adrenoceptor ligands Biochemistry 1994, 33, 9126-9134 (Pubitemid 24272863)
30. Staehelin, M.; Simons, P.; Jaeggi, K.; Wigger, N. CGP-12177-A hydrophilic beta-adrenergic receptor radioligand reveals high-affinity binding of agonists to intact-cells J. Biol. Chem. 1983, 258, 3496-3502 (Pubitemid 13055763)
31. McGrath, J. C.; Daly, C. J. Use of fluorescent ligands and receptors to visualize adrenergic receptors. In The Receptors: The Adrenergic Receptors: In the 21st Century; Perez, D. M., Ed.; Humana Press: New York, 2007; pp 151-172.
32. Baker, J. G.; Hall, I. P.; Hill, S. J. Pharmacology and direct visualisation of BODIPY-TMR-CGP: A long-acting fluorescent β2-adrenoceptor agonist Br. J. Pharmacol. 2003, 139, 232-242 (Pubitemid 36760355)
33. Hegener, O.; Prenner, L.; Runkel, F.; Baader, S. L.; Kappler, J.; Häberlein, H. Dynamics of beta2-adrenergic receptor-ligand complexes on living cells Biochemistry 2004, 43, 6190-6199 (Pubitemid 38669487)
34. Martikkala, E.; Lehmusto, M.; Lilja, M.; Rozwandowicz-Jansen, A.; Lunden, J.; Tomohiro, T.; Hanninen, P.; Petaja-Repo, U.; Harma, H. Cell-based beta-2-adrenergic receptor-ligand binding assay using synthesized europium-labeled ligands and time-resolved fluorescence Anal. Biochem. 2009, 392, 103-109
35. Briddon, S. J.; Middleton, R. J.; Yates, A. S.; George, M. W.; Kellam, B.; Hill, S. J. Application of fluorescence correlation spectroscopy to the measurement of agonist binding to a G-protein coupled receptor at the single cell level Faraday Discuss 2004, 126, 197-207 (Pubitemid 38372082)
36. Discussion 245-254.
37. Middleton, R. J.; Briddon, S. J.; Cordeaux, Y.; Yates, A. S.; Dale, C. L.; George, M. W.; Baker, J. G.; Hill, S. J.; Kellam, B. New fluorescent adenosine A1-receptor agonists that allow quantification of ligand-receptor interactions in microdomains of single living cells J. Med. Chem. 2007, 50, 782-793 (Pubitemid 46335649)
38. Briddon, S. J.; Middleton, R. J.; Cordeaux, Y.; Flavin, F. M.; Weinstein, J. A.; George, M. W.; Kellam, B.; Hill, S. J. Quantitative analysis of the formation and diffusion of A1-adenosine receptor-antagonist complexes in single living cells Proc. Natl. Acad. Sci. U. S. A. 2004, 101, 4673-4678 (Pubitemid 38437469)
39. Baker, J. G.; Middleton, R.; Adams, L.; May, L. T.; Briddon, S. J.; Kellam, B.; Hill, S. J. Influence of fluorophore and linker composition on the pharmacology of fluorescent adenosine A1 receptor ligands Br. J. Pharmacol. 2010, 159, 772-786
40. Briddon, S. J.; Hill, S. J. Pharmacology under the microscope: The use of fluorescence correlation spectroscopy to determine the properties of ligand-receptor complexes Trends Pharmacol. Sci. 2007, 28, 637-645 (Pubitemid 350166574)
41. Klunder, J. M.; Onami, T.; Sharpless, K. B. Arenesulfonate derivatives of homochiral glycidol: Versatile chiral building blocks for organic synthesis J. Org. Chem. 1989, 54, 1295-1304
42. Baker, J. G.; Hall, I. P.; Hill, S. J. Agonist actions of 'β-blockers' provide evidence for two agonist activation sites on the human β1-adrenoceptor Mol. Pharmacol. 2003, 63, 1312-1321 (Pubitemid 36627226)
43. 2- adrenoceptor provide evidence for agonist-directed signalling Mol. Pharmacol. 2003, 64, 1357-1369 (Pubitemid 37532226)
44. Baker, J. G. Evidence for a secondary state of the human β3-adrenoceptor Mol. Pharmacol. 2005, 68, 1645-1655 (Pubitemid 41654348)
45. Baker, J. G. The selectivity of beta-adrenoceptor agonists at human beta1-, beta2- and beta3-adrenoceptors Br. J. Pharmacol. 2010, 160, 1048-1061
46. Stephenson, R. P. A modification of receptor theory Br. J. Pharmacol. Chemother. 1956, 11, 379-393
47. Granneman, J. G. (2001). The putative beta4-adrenergic receptor is a novel state of the beta1-adrenergic receptor Am. J. Physiol. Endocrinol. Metab. 2001, 280, E199-E202
48. Kaumann, A. J.; Engelhardt, S.; Hein, L.; Molenaar, P.; Lohse, M. Abolition of (-)-CGP 12177-evoked cardiostimulation in double beta1/beta2-adrenoceptor knockout mice. Obligatory role of beta1-adrenoceptors for putative beta4-adrenoceptor pharmacology Naunyn Schmiedebergs Arch. Pharmacol. 2001, 363, 87-93 (Pubitemid 32060091)
49. Kaumann, A. J.; Molenaar, P. (2008). The low-affinity site of the beta1-adrenoceptor and its relevance to cardiovascular pharmacology Pharmacol Ther. 2008, 118, 303-336
50. Arch, J. R. Do low-affinity states of beta-adrenoceptors have roles in physiology and medicine? Br. J. Pharmacol. 2004, 143, 517-518 (Pubitemid 39524267)
51. Baker, J. G. Site of action of beta-ligands at the human beta1-adrenoceptor J. Pharmacol. Exp. Ther. 2005, 313, 1163-1171 (Pubitemid 40727019)
52. Dooley, D. J.; Bittiger, H.; Reymann, N. C. CGP 20712A: A useful tool for quantitating beta 1- and beta 2-adrenoceptors Eur. J. Pharmacol. 1986, 130, 137-139 (Pubitemid 17170862)
53. Baker, J. G. The selectivity of beta-adrenoceptor antagonists at the human β1, β2 and β3 adrenoceptors Br. J. Pharmacol. 2005, 144, 317-322 (Pubitemid 40313677)
54. May, L. T.; Briddon, S. J.; Hill, S. J. Antagonist selective modulation of adenosine A1- and A3- receptor pharmacology by the food dye Brilliant Black BN: Evidence for allosteric interactions Mol. Pharmacol. 2010, 77, 678-686
55. Collet, M.; Lenger, J.; Jenssen, K.; Hannes, P. P.; Sewald, N. Molecular tools for metalloprotease sub-proteome generation J. Biotechnol. 2007, 129, 316-328 (Pubitemid 46529022)
56. Chen, R.; Nguyen, P.; You, Z.; Sinsheimer, J. E. Enantioselective detoxication of optical isomers of glycidyl ethers Chirality 1993, 5, 501-504 (Pubitemid 23328441)