New flurbiprofen derivatives: Synthesis, membrane affinity and evaluation of in vitro effect on β-amyloid levels

Molecules

Volumn 18, Issue 9, 2013, Pages 10747-10767

  Sozio, Piera ^a   Marinelli, Lisa ^a   Cacciatore, Ivana ^a   Fontana, Antonella ^a   Türkez, Hasan ^b   Giorgioni, Gianfabio ^c   Ambrosini, Dario ^d   Barbato, Francesco ^e   Grumetto, Lucia ^e   Pacella, Stephanie ^a   Cataldi, Amelia ^a   Di Stefano, Antonio ^a  

^a UNIVERSITY OF CHIETI   (Italy)

^b ERZURUM TECHNICAL UNIVERSITY   (Turkey)

^c UNIVERSITY OF CAMERINO   (Italy)

^d NORTHEASTERN UNIVERSITY   (United States)

^e UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

secretase; Alzheimer's disease; Beta amyloid peptide; Flurbiprofen

Indexed keywords

AMYLOID BETA PROTEIN; AMYLOID BETA PROTEIN (1 42); AMYLOID BETA-PROTEIN (1-42); DRUG DERIVATIVE; FLURBIPROFEN; NONSTEROID ANTIINFLAMMATORY AGENT; PEPTIDE FRAGMENT; ARTIFICIAL MEMBRANE;

ALZHEIMER DISEASE; ANIMAL; ARTICLE; ARTIFICIAL MEMBRANE; ASTROCYTE; BIOLOGICAL MODEL; BLOOD BRAIN BARRIER; CELL CULTURE; CELL LINE; CHEMICAL PHENOMENA; DRUG EFFECT; DRUG SCREENING; HUMAN; METABOLISM; PERMEABILITY; PH; RAT; STEREOISOMERISM; SYNTHESIS; ANALOGS AND DERIVATIVES; DRUG EFFECTS;

ALZHEIMER DISEASE; AMYLOID BETA-PEPTIDES; ANIMALS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; ASTROCYTES; BLOOD-BRAIN BARRIER; CELL LINE; CELLS, CULTURED; DRUG EVALUATION, PRECLINICAL; FLURBIPROFEN; HUMANS; HYDROGEN-ION CONCENTRATION; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; MEMBRANES, ARTIFICIAL; MODELS, BIOLOGICAL; PEPTIDE FRAGMENTS; PERMEABILITY; RATS; STEREOISOMERISM;

EID: 84885144759     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules180910747     Document Type: Article

References (37)

1. Brookmeyer, R.; Johnson, E.; Ziegler-Graham, K.; Arrighi, H.M. Forecasting the global burden of Alzheimer′s disease. Alzheimers Dement. 2007, 3, 186-191. (Pubitemid 46825511)
2. D′Onofrio, G.; Panza, F.; Frisardi, V.; Solfrizzi, V.; Imbimbo, B.P.; Paroni, G.; Cascavilla, L.; Seripa, D.; Pilotto, A. Advances in the identification of γ-secretase inhibitors for the treatment of Alzheimer′s disease. Expert Opin. Drug Discov. 2012, 7, 19-37.
3. Mangialasche, F.; Solomon, A.; Winblad, B.; Mecocci, P.; Kivipelto, M. Alzheimer′s disease: Clinical trials and drug devel-opment. Lancet Neurol. 2010, 9, 702-716.
4. Wu, W.; Zhang, L. γ-secretase inhibitors for the treatment of Alzheimer′s disease. Drug Dev. Res. 2009, 70, 94-100.
5. Li, T.; Huang, Y.; Jin, S.; Ye, L.; Rong, N.; Yang, X.; Ding, Y.; Cheng, Z.; Zhang, J.; Wan, Z.; et al. γ-Secretase modulators do not induce Aβ-rebound and accumulation of β-C-terminal fragment. J. Neurochem. 2012, 121, 277-286.
6. Wolfe, M.S. γ-Secretase inhibitors and modulators for Alz-heimer′s disease. J. Neurochem. 2012, 120, 89-98.
7. Marjaux, E.; de Strooper, B. γ-Secretase inhibitors: still in the running as Alzheimer′s therapeutics. Drug Discov. Today 2004, 1, 1-6. (Pubitemid 40208001)
8. Peretto, I.; Radaelli, S.; Parini, C.; Zandi, M.; Raveglia, L.F.; Dondio, G.; Fontanella, L.; Misiano, P.; Bigogno, C.; Rizzi, A.; et al. Synthesis and biological activity of flurbiprofen analogues as selective inhibitors of β-amyloid1-42 secretion. J. Med. Chem. 2005, 48, 5705-5720. (Pubitemid 41298345)
9. Eriksen, J.L.; Sagi, S.A.; Smith, T.E.; Weggen, S.; Das, P.; McLendon, D.C.; Ozols, V.V.; Jessing, K.W.; Zavitz, K.H.; Koo, E.H.; et al. NSAIDs and enantiomers of flurbiprofen target γ-secretase and lower Aβ42 in vivo. J. Clin. Invest. 2003, 112, 440-449. (Pubitemid 38063773)
10. Kreft, A.F.; Martone, R.; Porte, A. Recent advances in the identification of γ-secretase inhibitors to clinically test the Aβ oligomer hypothesis of Alzheimer′s disease. J. Med. Chem. 2009, 52, 6169-6188.
11. Morihara, T.; Chu, T.; Ubeda, O.; Beech, W.; Cole, G.M. Selective inhibition of Aβ42 production by NSAID R-enantiomers. J. Neurochem. 2002, 83, 1009-1012. (Pubitemid 35316052)
12. El-Gendy, A.M.; Adejare, A. Membrane permeability related physicochemical properties of an ovel γ-secretase inhibitor. Int. J. Pharm. 2004, 280, 47-55. (Pubitemid 38950903)
13. Cardellini, M.; Cingolani, G.M.; Claudi, F.; Di Stefano, A.; Giorgioni G.F.; Cantalamessa, F.; Cagnotto, A.; Skorupska, M. Synthesis and evaluation of 2-(5-methoxythiophen-3-yl)ethylamines as potential dopamine agonists. Eur. J. Med. Chem. 1994, 29, 423-429. (Pubitemid 24236559)
14. Cacciatore, I.; Caccuri, A.M.; di Stefano, A.; Luisi, G.; Nalli, M.; Pinnen, F.; Ricci, G.; Sozio P. Synthesis and activity of novel glutathione analogues containing an urethane backbone linkare. Farmaco 2003, 58, 787-793. (Pubitemid 37122649)
15. Windsor, M.A.; Hermanson, D.J.; Kingsley, P.J.; Xu, S.; Crews, B.C.; Ho, W.; Keenan, C.M.; Banerjee, S.; Sharkey, K.A.; Marnett, L.J. Substrate-selective inhibition of cyclooxygen-ase-2: Development and evaluation of achiral profen probes. ACS Med. Chem. Lett. 2012, 3, 759-763.
16. Leroux, F.; Hutschenreuter, T.U.; Charrière, C.; Scopelliti, R.; Hartmann, R.W. N-(4-Biphenylmethyl)imidazoles as potential therapeutics for the treatment of prostate cancer: Metabolic robustness due to fluorine substitution? Helv. Chim. Acta 2003, 86, 2671-2686. (Pubitemid 37011982)
17. Klein, S.M.; Zhang, C.; Jiang, Y.L. Simple synthesis of fresh alkyl iodides using alcohols and hydriodic acid. Tetrahedron Lett. 2008, 49, 2638-2641.
18. Sozio, P.; D'Aurizio, E.; Iannitelli, A.; Cataldi, A.; Zara, S.; Cantalamessa, F.; Nasuti, C.; di Stefano, A. Ibuprofen and lipoic acid diamides as potential codrugs with neuroprotective activity. Arch. Pharm. Chem. Life Sci. 2010, 343, 133-142.
19. Hoffman-Emery, F.; Jakob-Roetne, R.; Flohr, A.; Bliss, F.; Reents, R. Improved synthesis of (S)-7-amino-5H,7H-dibenzo[b,d]azepin-6-one, a building block for γ-secretase inhibi-tors. Tetrahedron Lett. 2009, 50, 6380-6382.
20. Fauq, A.H.; Simpson, K.; Maharvi, G.M.; Golde, T.; Das, P. A multigram chemical synthe-sis of the c-secretase inhibitor LY411575 and its diastereoisomers. Bioorg. Med. Chem. Lett. 2007, 17, 6392-6395. (Pubitemid 47552801)
21. Byun E.; Hong B.; de Castro, K.A.; Lim, M.; Rhee, H. One-pot reductive mono-n-alkylation of aniline and nitroarene derivatives using aldehydes. J. Org. Chem. 2007, 72, 9815-9817. (Pubitemid 350231844)
22. Kametani, T.; Nemoto, H.; Takano, S. Chichibabin reaction III. Chichibabin reaction of 7-methylquinoline and migration of the methyl group in Friedel-Craft reaction of N-(m-tolyl)- and N-(p-tolyl)-β-chloropropionamide (Studies on the syntheses of heterocyclic compounds. CCXV) Pharm. Bull. 1968, 16, 367-370.
23. Peters, J.U.; Galley, G.; Jacobsen, H.; Czech, C.; David-Pierson, P.; Kitas, E.A.; Ozmenb, L Novel orally active, dibenzazepinone-based gamma-secretase inhibitors. Bioorg. Med. Chem. Lett. 2007, 17, 5918-5923. (Pubitemid 47446205)
24. Horter, D.; Dressman, J.B. Influence of physicochemical properties on dissolution of drugs in the gastrointestinal tract. Adv. Drug. Deliv. Rev. 2001, 46, 75-87.
25. Leo, A.J.; Hansch, C.; Elkins, D. Partition coefficients and their use. Chem. Rev. 1971, 71, 525-616.
26. Barbato, F.; la Rotonda, M.I.; Quaglia, F. Chromatographic indices determined on an immobilized artificial membrane (IAM) column as descriptors of lipophilic and polar interactions of 4-phenyldihydropyridine calcium-channel blockers with biomembranes. Eur. J. Med. Chem. 1996, 31, 311-318.
27. Barbato, F. The use of immobilized artificial membrane (IAM) chromatography for determination of lipophilicity. Curr. Comput. Aid. Drug 2006, 2, 341-352. (Pubitemid 46029593)
28. Kansy, M.; Senner, F.; Gubernator, K. Physicochemical high throughput screening: Parallel artificial membrane permeability assay in the description of passive absorption processes. J. Med. Chem. 1998, 41, 1007-1010. (Pubitemid 28207375)
29. Fischer, H.; Kansy, M.; Avdeef, A.; Senner, F. Permeation of permanently positive charged molecules through artificial mem-branes-influence of physico-chemical properties. Eur. J. Pharm. Sci. 2007, 31, 32-42. (Pubitemid 46601866)
30. Sozio, P.; Cerasa, L.S.; Laserra, S.; Cacciatore, I.; Cornacchia, C.; Di Filippo, E.S.; Fulle, S.; Fontana, A.; di Crescenzo, A.; Grilli, M.; et al. Memantine-sulfur containing antioxidant conjugates as potential prodrugs to improve the treatment of Alzheimer′s disease. Eur. J. Pharm. Sci. 2013, 49, 187-198.
31. Fabio, K.M.; Guillon, C.D.; Lu, S.F.; Heindel, N.D.; Brownstein M.J.; Lacey, C.J.; Garippa, C.; Simon, N.G. Pharmacokinetics and metabolism of SRX246: A potent and selective vasopressin 1a antagonist. J. Pharm. Sci. 2013, 102, 2033-2043.
32. Elvang, A.B.; Volbracht, C.; Pedersen, L.O.; Jensen, K.G.; Karlsson, J.J.; Larsen, S.A.; Mørk, A.; Stensbøl, T.B.; Bastlund, J.F. Differential effects of gamma-secretase and BACE1 inhibition on brain Abeta levels in vitro and in vivo. J. Neurochem. 2009, 110, 1377-1387.
33. Sozio, P.; Rapino, M.; Di Valerio, V.; Laserra, S.; Pacella, S.; Di Stefano, A.; Cataldi, A. pPKCα mediated effect on "in vitro" Aβ production in response to γ secretase inhibitor LY411575 in rat CTXTNA2 astrocytes. J. Biol. Reg. Homeos. Ag. 2012, 26, 245-251.
34. Sunesen, V.H.; Pedersen, B.L.; Kristensen, H.G.; Müllertz, A. Effect of liquid volume and food intake on the absolute bioavailability of danazol, a poorly soluble drug. Eur. J. Pharm. Sci. 2005, 24, 305-313.
35. Braumann, T.; Weber, G.; Gromme, L.H. Quantitative structure-activity relationships for herbicides. Reversed phase liquid chromatographic retention parameters, log kw versus liquid liquid partition coefficients as a model of the hydrophobicity of phenylureas, s-triazines and phenoxycarbonic acid derivatives. J. Chromatogr. 1983, 261, 329-343. (Pubitemid 13054545)
36. Di Stefano, A.; Sozio, P.; Iannitelli, A.; Cerasa, L. S.; Fontana, A.; Di Biase, G.; D′Amico, G.; di Giulio, M.; Carpentiero, C.; Grumetto, L.; Barbato, F. Characterization of alkanoyl-10-Ominocyclines in micellar dispersions as potential agents for treatment of human neurodegenerative disorders. Eur. J. Pharm. Sci. 2008, 34, 118-128.
37. Cacciatore, I.; Baldassarre, L.; Fornasari, E.; Cornacchia, C.; Di Stefano, A.; Sozio, P.; Cerasa, L. S.; Fontana, A.; Fulle, S.; di Filippo, E.S.; et al. (R)-a-lipoyl-glycyl-l-prolyl-l-glutamyl dimethyl ester codrug as a multifunctional agent with potential neuroprotective activities. Chem. Med. Chem. 2012, 7, 2021-2029.