Novel flurbiprofen derivatives with improved brain delivery: synthesis, in vitro and in vivo evaluations

References

• Ai J, Biazar E, Jafarpour M, et al. (2011). Nanotoxicology and nanoparticle safety in biomedical designs. Int J Nanomed 6:1117–1127
   PubMedGoogle Scholar
• Alam MI, Beg S, Samad A, et al. (2010). Strategy for effective brain drug delivery. Eur J Pharm Sci 40:385–403
   PubMed Web of Science ®Google Scholar
• Anderson BD. (1996). Prodrugs for improved CNS delivery. Adv Drug Deliv Rev 19:171–202
   Web of Science ®Google Scholar
• Brown RC, Morris AP, O’Neil RG. (2007). Tight junction protein expression and barrier properties of immortalized mouse brain microvessel endothelial cells. Brain Res 1130:17–30
   PubMed Web of Science ®Google Scholar
• Chen Q, Gong T, Liu J, et al. (2009). Synthesis, in vitro and in vivo characterization of glycosyl derivatives of ibuprofen as novel prodrugs for brain drug delivery. J Drug Target 17:318–28
   PubMed Web of Science ®Google Scholar
• Eriksen JL, Sagi SA, Smith TE, et al. (2003). NSAIDs and enantiomers of flurbiprofen target γ-secretase and lower Aβ42 in vivo. J Clin Invest 112:440–9
   PubMed Web of Science ®Google Scholar
• Etminan M, Gill S, Samii A. (2003). Effect of non-steroidal anti-inflammatory drugs on risk of Alzheimer’s disease: systematic review and meta-analysis of observational studies. BMJ 327:128
   PubMed Web of Science ®Google Scholar
• Gasparini L, Ongini E, Wenk G. (2004). Non-steroidal anti-inflammatory drugs (NSAIDs) in Alzheimer’s disease: old and new mechanisms of action. J Neurochem 91:521–36
   PubMed Web of Science ®Google Scholar
• Green RC, Schneider LS, Amato DA, et al. (2009). Effect of tarenflurbil on cognitive decline and activities of daily living in patients with mild Alzheimer disease. JAMA 302:2557–64
   PubMed Web of Science ®Google Scholar
• Halen PK, Chagti KK, Giridhar R, Yadav MR. (2007). Combining anticholinergic and anti-inflammatory activities into a single moiety: a novel approach to reduce gastrointestinal toxicity of ibuprofen and ketoprofen. Chem Biol Drug Des 70:450–5
   PubMed Web of Science ®Google Scholar
• Halmos T, Santarromana M, Antonakis K, Scherman D. (1996). Synthesis of glucose-chlorambucil derivatives and their recognition by the human GLUT1 glucose transporter. Eur J Pharm 318:477–84
   PubMed Web of Science ®Google Scholar
• Imbimbo BP. (2009a). An update on the efficacy of non-steroidal anti-inflammatory drugs in Alzheimer’s disease. Exp Opin Investig Drugs 18:1147–68
   PubMed Web of Science ®Google Scholar
• Imbimbo BP. (2009b). Why did tarenflurbil fail in Alzheimer’s disease? J Alzheimer’s Dis 17:757–60
   PubMed Web of Science ®Google Scholar
• Kasinathan N, Jagani HV, Alex AT, et al. (2014). Strategies for drug delivery to the central nervous system by systemic route. Drug Deliv [Epub ahead of print] 1–15
   Google Scholar
• Kukar T, Prescott S, Eriksen JL, et al. (2007). Chronic administration of R-flurbiprofen attenuates learning impairments in transgenic amyloid precursor protein mice. BMC Neurosci 8:54
   PubMed Web of Science ®Google Scholar
• Launer L, Breteler M, Hofman A, Stricker BC. (2002). Pharmacologic agents associated with a preventive effect on Alzheimer’s disease: a review of the epidemiologic evidence. Epidemiol Rev 24:248–68
   PubMed Web of Science ®Google Scholar
• Mittal D, Ali A, Md S, et al. (2014). Insights into direct nose to brain delivery: current status and future perspective. Drug Deliv 21:75–86
   PubMed Web of Science ®Google Scholar
• Parepally JMR, Mandula H, Smith QR. (2006). Brain uptake of nonsteroidal anti-inflammatory drugs: ibuprofen, flurbiprofen, and indomethacin. Pharm Res 23:873–81
   PubMed Web of Science ®Google Scholar
• Peretto I, Radaelli S, Parini C, et al. (2005). Synthesis and biological activity of flurbiprofen analogues as selective inhibitors of β-amyloid1-42 secretion. J Med Chem 48:5705–20
   PubMed Web of Science ®Google Scholar
• Pignatello R, Pant V, Salmaso S, et al. (2007). Flurbiprofen derivatives in Alzheimer’s disease: synthesis, pharmacokinetic and biological assessment of lipoamino acid prodrugs. Bioconjug Chem 19:349–57
   PubMed Web of Science ®Google Scholar
• Rautio J, Kumpulainen H, Heimbach T, et al. (2008). Prodrugs: design and clinical applications. Nat Rev Drug Discov 7:255–70
   PubMed Web of Science ®Google Scholar
• Song N, Li Y, Sun X, Qu F. (2004). Synthesis of (+/−) ibuprofen sugar derivatives. Acta Pharmacol Sinica 39:105–109
   Google Scholar
• Tammara VK, Narurkar MM, Crider AM, Khan MA. (1993). Synthesis and evaluation of morpholinoalkyl ester prodrugs of indomethacin and naproxen. Pharm Res 10:1191–9
   PubMed Web of Science ®Google Scholar
• Wilcock GK, Black SE, Hendrix SB, et al. (2008). Efficacy and safety of tarenflurbil in mild to moderate Alzheimer’s disease: a randomised phase II trial. Lancet Neurol 7:483–93
   PubMed Web of Science ®Google Scholar
• Zhang X, Liu X, Gong T, et al. (2012). In vitro and in vivo investigation of dexibuprofen derivatives for CNS delivery. Acta Pharmacol Sinica 33:279–88
   PubMed Web of Science ®Google Scholar