Brain-penetrant tetrahydronaphthalene thromboxane A2-prostanoid (TP) receptor antagonists as prototype therapeutics for Alzheimers disease

ACS Chemical Neuroscience

Volumn 3, Issue 11, 2012, Pages 928-940

  Soper, James H ^a   Sugiyama, Shimpei ^b   Herbst Robinson, Katie ^a   James, Michael J ^a   Wang, Xiaozhao ^b   Trojanowski, John Q ^a   Smith, Amos B ^b   Lee, Virginia M Y ^a   Ballatore, Carlo ^a,b   Brunden, Kurt R ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

^b UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

Alzheimers disease; amyloid precursor protein; antagonist; blood brain barrier; plaques; thromboxane receptor

Indexed keywords

AMYLOID PRECURSOR PROTEIN; BM 567; BM 587; CARBOXYLIC ACID; DALTROBAN; ISOPROSTANE DERIVATIVE; MESSENGER RNA; RAMATROBAN; THROMBOXANE A2 RECEPTOR BLOCKING AGENT; UNCLASSIFIED DRUG; VAPIPROST;

ALZHEIMER DISEASE; ANIMAL CELL; ARTICLE; BLOOD BRAIN BARRIER; CONTROLLED STUDY; LIPID OXIDATION; MOUSE; NONHUMAN; OXIDATIVE STRESS; PRIORITY JOURNAL; PROTEIN SECRETION; RECEPTOR BINDING; SENILE PLAQUE;

ALZHEIMER DISEASE; AMYLOID BETA-PEPTIDES; ANIMALS; BLOOD-BRAIN BARRIER; ENZYME-LINKED IMMUNOSORBENT ASSAY; FEMALE; MICE; POLYMERASE CHAIN REACTION; RECEPTORS, THROMBOXANE A2, PROSTAGLANDIN H2; TETRAHYDRONAPHTHALENES;

MUS;

EID: 84869753420     PISSN: None     EISSN: 19487193     Source Type: Journal    
DOI: 10.1021/cn3000795     Document Type: Article

References (47)

1. Mebane-Sims, I. (2009) 2009 Alzheimers disease facts and figures Alzheimer's Dementia 5, 234-270
2. Reitz, C., Brayne, C., and Mayeux, R. (2011) Epidemiology of Alzheimer disease Nat. Rev. Neurol. 7, 137-152
3. Akiyama, H., Barger, S., Barnum, S., Bradt, B., Bauer, J., Cole, G. M., Cooper, N. R., Eikelenboom, P., Emmerling, M., Fiebich, B. L., Finch, C. E., Frautschy, S., Griffin, W. S. T., Hampel, H., Hull, M., Landreth, G., Lue, L. F., Mrak, R., Mackenzie, I. R., Mcgeer, P. L., OBanion, M. K., Pachter, J., Pasinetti, G., Plata-Salaman, C., Rogers, J., Rydel, R., Shen, Y., Streit, W., Strohmeyer, R., Tooyoma, I., Van Muiswinkel, F. L., Veerhuis, R., Walker, D., Webster, S., Wegrzyniak, B., Wenk, G., and Wyss-Coray, T. (2000) Inflammation and Alzheimers disease Neurobiol. Aging 21, 383-421
4. De Strooper, B. (2010) Proteases and Proteolysis in Alzheimer Disease: A Multifactorial View on the Disease Process Physiol. Rev. 90, 465-494
5. Kosik, K. S., Joachim, C. L., and Selkoe, D. J. (1986) Microtubule-Associated Protein Tau (Tau) Is A Major Antigenic Component of Paired Helical Filaments in Alzheimer-Disease Proc. Natl. Acad. Sci. U.S.A. 83, 4044-4048
6. Lee, V. M. Y., Balin, B. J., Otvos, L., and Trojanowski, J. Q. (1991) A68-A Major Subunit of Paired Helical Filaments and Derivatized Forms of Normal-Tau Science 251, 675-678
7. Citron, M., Oltersdorf, T., Haass, C., Mcconlogue, L., Hung, A. Y., Seubert, P., Vigopelfrey, C., Lieberburg, I., and Selkoe, D. J. (1992) Mutation of the Beta-Amyloid Precursor Protein in Familial Alzheimers-Disease Increases Beta-Protein Production Nature 360, 672-674
8. Haass, C., Lemere, C. A., Capell, A., Citron, M., Seubert, P., Schenk, D., Lannfelt, L., and Selkoe, D. J. (1995) The Swedish Mutation Causes Early-Onset Alzheimers-Disease by Beta-Secretase Cleavage Within the Secretory Pathway Nat. Med. 1, 1291-1296
9. Mullan, M., Tsuji, S., Miki, T., Katsuya, T., Naruse, S., Kaneko, K., Shimizu, T., Kojima, T., Nakano, I., Ogihara, T., Miyatake, T., Ovenstone, I., Crawford, F., Goate, A., Hardy, J., Roques, P., Roberts, G., Luthert, P., Lantos, P., Clark, C., Gaskell, P., Crain, B., and Roses, A. (1993) Clinical Comparison of Alzheimers-Disease in Pedigrees with the Codon-717 Val-]Ile Mutation in the Amyloid Precursor Protein Gene Neurobiol. Aging 14, 407-419
10. Tanzi, R. E. and Bertram, L. (2005) Twenty years of the Alzheimers disease amyloid hypothesis: A genetic perspective Cell 120, 545-555
11. Luo, Y., Bolon, B., Kahn, S., Bennett, B. D., Babu-Khan, S., Denis, P., Fan, W., Kha, H., Zhang, J. H., Gong, Y. H., Martin, L., Louis, J. C., Yan, Q., Richards, W. G., Citron, M., and Vassar, R. (2001) Mice deficient in BACE1, the Alzheimers beta-secretase, have normal phenotype and abolished beta-amyloid generation Nat. Neurosci. 4, 231-232
12. Lundkvist, J. and Naslund, J. (2007) gamma-Secretase: a complex target for Alzheimers disease Curr. Opin. Pharmacol. 7, 112-118
13. Sayre, L. M., Perry, G., and Smith, M. A. (2008) Oxidative stress and neurotoxicity Chem. Res. Toxicol. 21, 172-188
14. Butterfield, D. A., Perluigi, M., and Sultana, R. (2006) Oxidative stress in Alzheimers disease brain: New insights from redox proteomics Eur. J. Pharmacol. 545, 39-50
15. Pratico, D., Clark, C. M., Lee, V. M. Y., Trojanowski, J. Q., Rokach, J., and FitzGerald, G. A. (2000) Increased 8,12-iso-iPF(2 alpha)-VI in Alzheimers disease: Correlation of a noninvasive index of lipid peroxidation with disease severity Ann. Neurol. 48, 809-812
16. Pratico, D., Lee, V. M. Y., Trojanowski, J. Q., Rokach, J., and FitzGerald, G. A. (1998) Increased F-2-isoprostanes in Alzheimers disease: evidence for enhanced lipid peroxidation in vivo FASEB J. 12, 1777-1783
17. Montine, T. J., Markesbery, W. R., Morrow, J. D., and Roberts, L. J. (1998) Cerebrospinal fluid F-2-isoprostane levels are increased in Alzheimers disease Ann. Neurol. 44, 410-413
18. Pratico, D., Uryu, K., Leight, S., Trojanowswki, J. Q., and Lee, V. M. Y. (2001) Increased lipid peroxidation precedes amyloid plaque formation in an animal model of Alzheimer amyloidosis J. Neurosci. 21, 4183-4187
19. Breyer, R. M., Bagdassarian, C. K., Myers, S. A., and Breyer, M. D. (2001) Prostanoid receptors: Subtypes and signaling Annu. Rev. Pharmacol. Toxicol. 41, 661-690
20. Huang, J. S., Ramamurthy, S. K., Lin, X., and Le Breton, G. C. (2004) Cell signalling through thromboxane A(2) receptors Cell. Signalling 16, 521-533
21. Elmhurst, J. L., Betti, P. A., and Rangachari, P. K. (1997) Intestinal effects of isoprostanes: Evidence for the involvement of prostanoid EP and TP receptors J. Pharmacol. Exp. Ther. 282, 1198-1205
22. Shineman, D., Zhang, B., Leight, S., Pratico, D., and Lee, V. (2008) Thromboxane receptor activation mediates isoprostane-induced increases in amyloid pathology in Tg2576 mice J. Neurosci. 28, 4785-4794
23. Cimetière, B, Dubuffet, T, Muller, O, Descombes, J. J., Simonet, S, Laubie, M, Verbeuren, T. J., and Lavielle, G. (2008) Synthesis and biological evaluation of new tetrahydronaphthalene derivatives as thromboxane receptor antagonists Bioorg. Med. Chem. Lett. 8, 1375-1380
24. Narumiya, S. and FitzGerald, G. A. (2001) Genetic and pharmacological analysis of prostanoid receptor function J. Clin. Invest. 108, 25-30
25. Chaer, R. A., Graham, J. A., and Mureebe, L. (2006) Platelet function and pharmacologic inhibition Vasc. Endovasc. Surg. 40, 261-267
26. Austin, R. P., Davis, A. M., and Manners, C. N. (1995) Partitioning of Ionizing Molecules Between Aqueous Buffers and Phospholipid-Vesicles J. Pharm. Sci. 84, 1180-1183
27. Pajouhesh, H. and Lenz, G. R. (2008) Medicinal chemical properties of successful central nervous system drugs NeuroRx 2, 541-553
28. Morinelli, T. A., Oatis, J. E., Okwu, A. K., Mais, D. E., Mayeux, P. R., Masuda, A., Knapp, D. R., and Halushka, P. V. (1989) Characterization of An I-125-Labeled Thromboxane-A2/Prostaglandin-H2 Receptor Agonist J. Pharmacol. Exp. Ther. 251, 557-562
29. Lefer, D. J., Mentley, R. K., and Lefer, A. M. (1987) Protective Effects of A New Specific Thromboxane Antagonist in Arachidonate-Induced Sudden-Death Arch. Int. Pharmacodyn. Ther. 287, 89-95
30. Knezevic, I., Borg, C., and Lebreton, G. C. (1993) Identification of Gq As One of the G-Proteins Which Copurify with Human Platelet Thromboxane-A2 Prostaglandin-H2 Receptors Blood 82, A156
31. Dorn, G. W., Burch, R. M., Kochel, P. J., Mais, D. E., and Halushka, P. V. (1987) Decrease in Agonist Affinity for Human-Platelet Thromboxane-A2 Prostaglandin-H2 Receptors Induced by A Platelet-Derived Supernatant Biochem. Pharmacol. 36, 1913-1917
32. Trachte, G. J. (1986) Thromboxane Agonist (U46619) Potentiates Norepinephrine Efflux from Adrenergic-Nerves J. Pharmacol. Exp. Ther. 237, 473-477
33. Colquhoun, D. (2007) Why the Schild method is better than Schild realised Trends Pharmacol. Sci. 28, 608-614
34. Giraldo, J., Serra, J., Roche, D., and Rovira, X. (2007) Assessing receptor affinity for inverse agonists: Schild and Cheng-Prusoff methods revisited Curr. Drug Targets 8, 197-202
35. Funk, C. D., Furci, L., Moran, N., and FitzGerald, G. A. (1993) Point Mutation in the 7Th Hydrophobic Domain of the Human Thromboxane-A(2) Receptor Allows Discrimination Between Agonist and Antagonist Binding-Sites Mol. Pharmacol. 44, 934-939
36. Barbu, E., Molnar, E., Tsibouklis, J., and Gorecki, D. C. (2009) The potential for nanoparticle-based drug delivery to the brain: overcoming the blood-brain barrier Expert. Opin. Drug Delivery 6, 553-565
37. Chandra, A., Viswanathan, R., and Johnston, J. N. (2007) Synthesis of the ABC- and D-ring systems of the indole alkaloid ambiguine G Org. Lett. 9, 5027-5029
38. Iida, S. and Togo, H. (2007) Direct oxidative conversion of alcohols and amines to nitriles with molecular iodine and DIH in aq NH3 Tetrahedron 63, 8274-8281
39. Demko, Z. P. and Sharpless, K. B. (2001) Preparation of 5-substituted 1H-tetrazoles from nitriles in water J. Org. Chem. 66, 7945-7950
40. Dondoni, A., Fantin, G., Fogagnolo, M., Medici, A., and Pedrini, P. (1988) Thiazolylmethylenetriphenylphosporane and its benzo derivative: stable and practical wittig reagents for the synthesis of vinylthiazoles and vinylbenzo: two-carbon homologation of aldehydes Tetrahedron 44, 2021-2031
41. Cimetière, B., Dubuffet, T, Muller, O, Descombes, J. J., Simonet, S, Laubie, M, Verbeuren, T. J., and Lavielle, G. (1998) Synthesis and biological evaluation of new tetrahydronaphthalene derivatives as thromboxane receptor antagonists Bioorg. Med. Chem. Lett. 8, 1375-1380
42. Watts, I. S., Wharton, K. A., White, B. P., and Lumley, P. (1991) Thromboxane (Tx) A2 Receptor Blockade and Txa2 Synthase Inhibition Alone and in Combination-Comparison of Anti-Aggregatory Efficacy in Human Platelets Br. J. Pharmacol. 102, 497-505
43. Thomas, D. W., Mannon, R. B., Mannon, P. J., Latour, A., Oliver, J. A., Hoffman, M., Smithies, O., Koller, B. H., and Coffman, T. M. (1998) Coagulation defects and altered hemodynamic responses in mice lacking receptors for thromboxane A(2) J. Clin. Invest. 102, 1994-2001
44. Hirata, T., Kakizuka, A., Ushikubi, F., Fuse, I., Okuma, M., and Narumiya, S. (1994) Arg(60) to Leu Mutation of the Human Thromboxane A(2) Receptor in A Dominantly Inherited Bleeding Disorder J. Clin. Invest. 94, 1662-1667
45. Mumford, A. D., Dawood, B. B., Daly, M. E., Murden, S. L., Williams, M. D., Protty, M. B., Spalton, J. C., Wheatley, M., Mundell, S. J., and Watson, S. P. (2010) A novel thromboxane A(2) receptor D304N variant that abrogates ligand binding in a patient with a bleeding diathesis Blood 115, 363-369
46. Gravina, S. A., Ho, L. B., Eckman, C. B., Long, K. E., Otvos, L., Younkin, L. H., Suzuki, N., and Younkin, S. G. (1995) Amyloid-Beta Protein (A-Beta) in Alzheimers-Disease Brain-Biochemical and Immunocytochemical Analysis with Antibodies Specific for Forms Ending at A-Beta-40 Or A-Beta-42(43) J. Biol. Chem. 270, 7013-7016
47. Brunden, K. R., Yao, Y., Potuzak, J. S., Ferrar, N. I., Ballatore, C., James, M. J., Hogan, A. L., Trojanowski, J. Q., Smith, A. B., 3, and Lee, V. M. Y. (2011) The characterization of microtubule-stabilizing drugs as possible therapeutic agents for Alzheimers disease and related tauopathies Pharmacol. Res. 63, 341-351