Phenolic bis-styrylbenzenes as β-amyloid binding ligands and free radical scavengers

Journal of Medicinal Chemistry

Volumn 53, Issue 22, 2010, Pages 7992-7999

  Flaherty, Daniel P ^a   Kiyota, Tomomi ^a   Dong, Yuxiang ^a   Ikezu, Tsuneya ^a   Vennerstrom, Jonathan L ^a  

^a NEBRASKA MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 (3 HYDROXYSTYRYL) 4 (3,4 DIHYDROXYSTYRYL)BENZENE; 1 (4 HYDROXYSTYRYL) 4 (3 HYDROXYSTYRYL)BENZENE; 1 (4 HYDROXYSTYRYL) 4 (3,4 DIHYDROXYSTYRYL)BENZENE; 1 (4 HYDROXYSTYRYL) 4 (3,5 DIHYDROXYSTYRYL)BENZENE; 1 [3 (METHOXYMETHOXY)STYRYL] 4 [3,4 DI(METHOXYMETHOXY)STYRYL]BENZENE; 1 [4 (METHOXYMETHOXY)STYRYL] 4 [3 (METHOXYMETHOXY)STYTYL]BENZENE; 1 [4 (METHOXYMETHOXY)STYRYL] 4 [3,4 DI(METHOXYMETHOXY)STYRYL]BENZENE; 1 [4 (METHOXYMETHOXY)STYRYL] 4 [3,5 DI(METHOXYMETHOXY)STYRYL]BENZENE; 1 STYRYL 4 (4 HYDROXYSTYRYL)BENZENE; 1 STYRYL 4 [4 (METHOXYMETHOXY)STYRYL]BENZENE; 1,2 BIS(4 HYDROXYSTYRYL)BENZENE; 1,3 BIS(4 HYDROXYSTYRYL)BENZENE; 1,4 BIS(2 HYDROXYSTYRYL)BENZENE; 1,4 BIS(3 HYDROXYSTYRYL)BENZENE; 1,4 BIS(3,5 DIHYDROXYSTYRYL)BENZENE; 1,4 BIS(4 HYDROXYSTYRYL)BENZENE; ALKENE; ALKYNE; AMYLOID BETA PROTEIN; AMYLOID BETA PROTEIN[1-40]; FREE RADICAL; MONOSTYRYLBENZENE DERIVATIVE; PHENOLIC BIS STYRYLBENZENE DERIVATIVE; QUERCETIN; STILBENE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ANTIOXIDANT ACTIVITY; ARTICLE; BINDING AFFINITY; BLOOD BRAIN BARRIER; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN TISSUE; MOUSE; NONHUMAN; SINGLE DRUG DOSE; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

ALZHEIMER DISEASE; AMYLOID BETA-PEPTIDES; ANIMALS; BLOOD-BRAIN BARRIER; BRAIN; DRUG DESIGN; FREE RADICAL SCAVENGERS; HUMANS; LIGANDS; MICE; MICE, TRANSGENIC; PHENOLS; PLAQUE, AMYLOID; PROTEIN BINDING; STEREOISOMERISM; STILBENES;

EID: 78649519367     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm1006929     Document Type: Article

References (45)

1. Goedert, M; Spillantini, G. A Century of Alzheimer's Disease Science 2006, 314, 777-781
2. Hebert, L. E.; Scherr, P. A.; Bienias, J. L.; Bennett, D. A.; Evans, D. A. Alzheimer's Disease in the United States in the U.S. Population: Prevalence Estimates Using the 2000 Census Arch. Neurol. 2003, 60, 1119-1122
3. Alzheimer, A. Ueber eine Eigenartige Erkankung der Hirnrinde Allg. Z. Psychiatr. 1907, 64, 146-148
4. Selkoe, D. J. Alzheimer's Disease: Genotypes, Phenotypes and Treatments Science 1997, 275, 630-631
5. Berg, L.; McKeel, D. W., Jr.; Miller, J. P.; Baty, J.; Morris, J. C. Neuropathological Indexes of Alzheimer's Disease in Demented and Nondemented Persons Aged 80 Years or Older Arch. Neurol. 1993, 50, 349-358
6. Schmitt, F. A.; Davis, D. G.; Wekstein, D. R.; Smith, C. D.; Ashford, J. W.; Markesbery, W. R. "Preclinical" AD Revisited: Neuropathology of Cognitively Normal Older Adults Neurology 2000, 55, 370-376
7. Hardy, J.; Selkoe, D. J. The Amyloid Hypothesis of Alzheimer's Disease: Progress and Problems on the Road to Therapeutics Science 2002, 297, 353-356
8. Strittmatter, W. J.; Saunders, A. M.; Schmechel, D.; Pericak-Vance, M.; Enghild, J.; Salvesen, G. S.; Roses, A. D. Apolipoprotein E: High-Avidity Binding to Amyloid and Increased Frequency of Type 4 Allele in Late-Onset Familial Alzheimer Disease Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 1977-1981
9. Puchtler, H.; Sweat, F.; Levine, M. On the Binding of Congo Red by Amyloid J. Histochem. Cytochem. 1962, 10, 355-364
10. Styren, S. D.; Hamilton, R. L.; Styren, G. C.; Klunk, W. E. X-34, a Fluorescent Derivative of Congo Red: A Novel Histochemical Stain for Alzheimer's Disease Pathology J. Histochem. Cytochem. 2000, 48, 1223-1232
11. 13C-Labeled Styrylbenzene Derivatives for Detecting Brain Amyloid Plaques Eur. J. Med. Chem. 2004, 39, 573-578
12. 1H MRI Detection of Amyloid Plaques in Vivo Nat. Neurosci. 2005, 8, 527-533
13. Crystal, A. S.; Giasson, B. I.; Crowe, A.; Kung, M. P.; Zhuang, Z. P.; Trojanowski, J. Q.; Lee, V. M. Y. A Comparison of Amyloid Fibrollogenesis Using the Novel Fluorescent Compound K114 J. Neurochem. 2003, 86, 1359-1368
14. Flaherty, D. P.; Walsh, S. M.; Kiyota, T.; Dong, Y.; Ikezu, T.; Vennerstrom, J. L. Polyfluorinated Bis-styrylbenzene β-Amyloid Plaque Binding Ligands J. Med. Chem. 2007, 50, 4986-4992. Compound 4 was prepared previously in our lab using a Horner-Wadsworth-Emmons coupling with 1,4-bis(diethyl phosphonylmethyl)benzene and p -anisaldehyde to form (E, E)-1,4-bis(4-methoxy)styrylbenzene which was deprotected with 1.0 M boron tribromide in DCM to yield 4
15. 18F Stilbenes and Styrylpyridines for PET Imaging of Aβ Plaques in Alzheimer's Disease: A Miniperspective J. Med. Chem. 2010, 53, 933-941
16. Huynh, T. H. V.; Mantel, M. L. H.; Mikkelson, K.; Lindhardt, A. T.; Nielson, N. C.; Otzen, D.; Skrydstrup, T. A Versatile Approach to β-Amyloid Fibril-Binding Compounds Exploiting the Shirakawa/Hayashi Protocol for trans -Alkene Synthesis Org. Lett. 2009, 11, 999-1002
17. Villano, D.; Fernandez-Pachon, M. S.; Troncoso, A. M.; Garcia-Parrilla, M. C. Comparison of Antioxidant Activity of Wine Phenolic Compounds and Metabolites in Vitro Anal. Chim. Acta 2005, 538, 391-398
18. Feng, Y.; Wang, X.-P.; Yang, S.-G.; Wang, Y.-J.; Zhang, X.; Du, X.-T.; Sun, X.-X.; Zhao, M.; Huang, L.; Liu, R.-T. Resveratrol Inhibits β-Amyloid Oligomeric Cytotoxicity but Does Not Prevent Oligomer Formation Neurotoxicology 2009, 30, 986-995
19. Sayre, L. M.; Perry, G.; Smith, M. A. Oxidative Stress and Neurotoxicity Chem. Res. Toxicol. 2008, 21, 172-188
20. Bruza, K. J. Bis((aryl)vinyl)benzenes. U.S. Patent 4,529,556, 1985.
21. Solntsev, K. M.; McGrier, P. L.; Fahrni, C. J.; Tolbert, L. M.; Bunz, U. H. F. Anomalous Photophysics of Bis(hydroxystyryl)benzenes: A Twist on the Para/Meta Dichotomy Org. Lett. 2008, 10, 2429-2432
22. Gerold, J.; Holzenkamp, U.; Meier, H. Bis-, Tris- and Tetrakis(squaraines) Linked by Stilbenoid Scaffolds Eur. J. Org. Chem. 2001, 2757-2763
23. Flaherty, D. P.; Dong, Y.; Vennerstrom, J. L. A One-Pot Synthesis of Unsymmetrical Bis-styrylbenzenes Tetrahedron Lett. 2009, 50, 6228-6230
24. Mantel, M. L. H.; Søbjerg, L. S.; Huynh, T. H. V.; Ebran, J.-P.; Lindhardt (né Hansen), A. T.; Nielsen, N. C.; Skrydstrup, T. An Expedient Synthesis of the Fibril Binding Compounds FSB via Sequential Pd-Catalyzed Couplings Reactions J. Org. Chem. 2008, 73, 3570-3573
25. Cui, X.; Zhou, Y.; Wang, N.; Liu, L.; Guo, Q.-X. N -Phenylurea as an Inexpensive and Efficient Ligand for Pd-Catalyzed Heck and Room-Temperature Suzuki Reactions Tetrahedron Lett. 2007, 48, 163-167
26. Tew, G. N.; Pralle, M. U.; Stupp, S. I. Supramolecular Materials from Triblock Rodcoil Molecules Containing Phenylene Vinylene J. Am. Chem. Soc. 1999, 121, 9852-9866
27. Wood, J. H.; Bacon, J. A.; Meibohm, A. W.; Throckmorton, W. H.; Turner, G. P. The Synthesis of Symmetrical Diaryl Ethylenes J. Am. Chem. Soc. 1941, 63, 1334-1335
28. Yam, C. M.; Kakkar, A. K. Molecular Self-Assembly of Dihydroxy-Terminated Molecules via Acid-Base Hydrolytic Chemistry of Silica Surfaces: Step-by-Step Multilayered Thin Film Construction Langmuir 1999, 15, 3807-3815. Compound 17 was prepared by this group via a Heck reaction between 1,4-diethynylbenzene and 4-iodophenol in 50% yield. Our attempts at synthesizing 17 using this method failed, and we isolated only the mono-Heck product and an insoluble impurity
29. Lockhart, A.; Ye, L.; Judd, D. B.; Merritt, A. T.; Lowe, P. N.; Morgenstern, J. L; Hong, G.; Gee, A. D.; Brown, J. Evidence for the Presence of Three Binding Sites for the Thioflavin T Class of Alzheimer's Disease PET Imaging Agents on Amyloid Peptide Fibrils J. Biol. Chem. 2005, 280, 7677-7684
30. Hsiao, K.; Chapman, P.; Nilsen, S.; Eckman, C.; Harigaya, Y.; Younkin, S.; Yang, F.; Cole, G. Correlative Memory Deficits, Aβ Elevation, and Amyloid Plaques in Transgenic Mice Science 1996, 274, 99-102
31. Duff, K.; Eckman, C.; Zehr, C.; Yu, X.; Prada, C. M.; Perez-tur, J.; Hutton, M.; Buee, L.; Harigaya, Y.; Yager, D.; Morgan, D.; Gordon, M. N.; Holcomb, L.; Refolo, L.; Zenk, B.; Hardy, J.; Younkin, S. Increased Amyloid-42(43) in Brains of Mice Expressing Mutant Presenilin 1 Nature 1996, 383, 710-713
32. Byeon, S. R.; Lee, J. H.; Sohn, J.-H.; Kim, D. C.; Shin, K. J.; Yoo, K. H.; Mook-Jung, I.; Lee, W. K.; Kim, D. J. Bis-styrylpyridine and Bis-styrylbenzene Derivatives as Inhibitors for Aβ Fibril Formation Bioorg. Chem. Lett. 2007, 17, 1466-1470
33. Li, Q.; Min, J.; Ahn, Y.-H.; Namm, J.; Kim, E.-M.; Lui, R.; Kim, H.-Y.; Ji, Y.; Wu, H.; Wisniewski, T.; Chang, Y.-T. Styryl-Based Compounds as Potential in Vivo Imaging Agents for β-Amyloid Plaques ChemBioChem 2007, 8, 1679-1687
34. Yang, L. X.; Huang, K. X.; Li, H. B.; Gong, J. X.; Wang, F.; Feng, Y. B.; Tao, Q. F.; Wu, Y. H.; Li, X. K.; Wu, X. M.; Zeng, S.; Spencer, S.; Zhao, Y.; Qu, J. Design, Synthesis, and Examination of Neuron Protective Properties of Alkenylated and Amidated Dehydro-Silybin Derivatives J. Med. Chem. 2009, 52, 7732-7752
35. Tewari, R.; Kumari, N.; Kendurkar, P. Studies on Ylides: Stereospecific Synthesis of trans, trans -Distyrylbenzenes and trans, trans -Divinylbenzenes Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1977, 15, 753-755
36. Blois, M. S. Antioxidant Determinations by the Use of a Stable Free Radical Nature 1958, 181, 1199-1200
37. Maksimovic, Z. In Vitro Antioxidant Activity of Ragweed (Ambrosia artemisiifolia L., Asteraceae) Herb Ind. Crops Prod. 2008, 28, 356-360
38. Winter, A.; Friebe, C.; Hager, M. D.; Schubert, U. S. Synthesis of Rigid π-Conjugated Mono-, Bis-, Tris-, and Tetrakis(terpyridine)s: Influence of the Degree and Pattern of Substitution on the Photophysical Properties Eur. J. Org. Chem. 2009, 6, 801-809
39. Barbasiewicz, M.; Makosza, M. Intermolecular Reactions of Chlorohydrine Anions: Acetalization of Carbonyl Compounds Under Basic Conditions Org. Lett. 2006, 8, 3745-3748
40. Hintermann, L.; Masuo, R.; Suzuki, K. Solvent-Controlled Leaving-Group Selectivity in Aromatic Nucleophilic Substitution Org. Lett. 2008, 10, 4859-4862
41. 1 Biosynthesis J. Chem. Soc., Perkin Trans 1 1988, 4, 839-861
42. Frazier, K. A.; Renga, J. M. Preparation of Ethenylidenes. U.S. Patent 4,713,458, 1987.
43. Thakkar, K.; Geahlen, R. L.; Cushman, M. Synthesis and Protein-Tyrosine Kinase Inhibitory Activity of Polyhydroxylated Stilbene Analogues of Piceatannol J. Med. Chem. 1993, 36, 2950-2955
44. Bull, S. R.; Palmer, L. C.; Fry, N. J.; Greenfield, M. A.; Messmore, B. W.; Meade, T. J.; Stupp, S. I. A Templating Approach for Monodisperse Self-Assembled Organic Nanostructures J. Am. Chem. Soc. 2008, 130, 2742-2743
45. Fauonneau, B.; Waffo-Teguo, P.; Huguet, F.; Barrier, L.; Decendit, A.; Merillon, J.-M. Comparative Study of Radical Scavengers and Antioxidant Properties of Phenolic Compounds from Vitis vinifera Cell Cultures Using in Vitro Tests Life Sci. 1997, 61, 2103-2110