Novel brain targeting prodrugs of naproxen based on dimethylamino group with various linkages

Arzneimittel-Forschung/Drug Research

Volumn 62, Issue 6, 2012, Pages 261-266

  Zhang, Q ^a   Liang, Z ^a   Chen, L Y ^a   Sun, X ^a   Gong, T ^a   Zhang, Z R ^a  

^a SICHUAN UNIVERSITY   (China)

Author keywords

Alzheimer's disease (AD); brain targeting; dimethylamino group; drug design; naproxen; prodrugs

Indexed keywords

AMIDE; NAPROXEN; PRODRUG;

ALZHEIMER DISEASE; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; AREA UNDER THE CURVE; ARTICLE; BLOOD BRAIN BARRIER; BRAIN HOMOGENATE; DRUG DISTRIBUTION; DRUG RELEASE; DRUG TARGETING; FEMALE; IN VITRO STUDY; IN VIVO STUDY; MAXIMUM PLASMA CONCENTRATION; NONHUMAN; RAT; SYNTHESIS;

ANIMALS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; AREA UNDER CURVE; BLOOD-BRAIN BARRIER; BRAIN; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DRUG DELIVERY SYSTEMS; FEMALE; HALF-LIFE; INDICATORS AND REAGENTS; INJECTIONS, INTRAVENOUS; MASS SPECTROMETRY; NAPROXEN; PRODRUGS; RATS; RATS, WISTAR; TISSUE DISTRIBUTION;

EID: 84862839207     PISSN: 00044172     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-0032-1306273     Document Type: Article

References (25)

1. Patel P M, Drummond J C, Sano T et al. Effect of ibuprofen on regional eicosanoid production and neuronal injury after forebrain ischemia in rats. Brain Res: 1993; 614 316 324
2. Silakova J M, Hewett J A, Hewett S J. Naproxen reduces excitotoxic neurodegeneration in vivo with an extended therapeutic window. J Pharmacol Exp Ther: 2004; 309 1060 1066 (Pubitemid 38669692)
3. Szekely C A, Thorne J E, Zandi P P et al. Nonsteroidal anti-inflammatory drugs for the prevention of Alzheimer's disease: a systematic review. Neuroepidemiology: 2004; 23 159 169 (Pubitemid 38980441)
4. Gasparini L, Ongini E, Wenk G. Non-steroidal anti-inflammatory drugs (NSAIDs) in Alzheimer's disease: old and new mechanisms of action. J Neurochem: 2004; 91 521 536 (Pubitemid 39431148)
5. Hirohata M, Ono K, Naiki H et al. Non-steroidal anti-inflammatory drugs have anti-amyloidogenic effects for Alzheimer's beta-amyloid fibrils in vitro. Neuropharmacology: 2005; 49 1088 1099 (Pubitemid 41503307)
6. Rainsford K D, Schweitzer A, Brune K. Autoradiographic and biochemical observations on the distribution of non-steroid anti-inflammatory drugs. Arch Int Pharmacodyn Ther: 1981; 250 180 194 (Pubitemid 11121091)
7. Brune K, Neubert A. Pharmacokinetic and pharmacodynamic aspects of the ideal COX-2 inhibitor: a pharmacologist's perspective. Clin Exp Rheumatol: 2001; 19 25 S51 S57 (Pubitemid 32998441)
8. Eriksen J L, Sagi S A, Smith T E et al. NSAIDs and enantiomers of flurbiprofen target gamma-secretase and lower Abeta 42 in vivo. J Clin Invest: 2003; 112 440 449 (Pubitemid 38063773)
9. Marchal-Heussler L, Maincent P, Hoffman M et al. Antiglaucomatous activity of betaxolol chlorhydrate sorbed onto different isobutylcyanoacrylate nanoparticle preparations. Int J Pharm: 1990; 58 115 122 (Pubitemid 20042451)
10. Chen Q, Gong T, Liu J et al. Synthesis, in vitro and in vivo characterization of glycosyl derivatives of ibuprofen as novel prodrugs for brain drug delivery. J Drug Target: 2009; 17 318 328
11. Saavedra J E, Billiar T R, Williams D L et al. Targeting nitric oxide (NO) delivery in vivo. Design of a liver-selective NO donor prodrug that blocks tumor necrosis factor-α-induced apoptosis and toxicity in the liver. J Med Chem: 1997; 40 1974 1954
12. Valckenborgh E V, Mincher D, Salvo A D et al. Targeting an MMP-9-activated prodrug to multiple myeloma-diseased bone marrow: a proof of principle in the 5T33MM mouse model. Leukemia: 2005; 19 1628 1633 (Pubitemid 43090408)
13. Zhang X, Liu X, Gong T et al. In vitro and in vivo study of dexibuprofen derivatives for CNS delivery. Acta Pharmacol Sin: 2012; 33 279 288
14. Buchwald P, Bodor N. Quantitative structure-metabolism relationships: steric and nonsteric effects in the enzymatic hydrolysis of noncongener carboxylic esters. J Med Chem: 1999; 42 5160 5168 (Pubitemid 30020267)
15. Larsen C, Johansen M. Macromolecular prodrugs I. Kinetics and mechanism of hydrolysis of O-benzoyl dextran conjugates in aqueous buffer and in human plasma. Int J Pharm: 1985; 27 205 218 (Pubitemid 16218672)
16. Ettmayer P, Amidon G L, Clement B et al. Lessons learned from marketed and investigational prodrugs. J Med Chem: 2004; 47 2393 2404 (Pubitemid 38580074)
17. Chang C S, Tsai S W. A facile enzymatic process for the preparation of (S)-Naproxen ester prodrug in organic solvents. Enzyme Microb Tech: 1997; 20 635 639
18. Halmos T, Santarromana M, Antonakis K et al. Synthesis of glucose-chlorambucil derivatives and their recognition by the human GLUT1 glucose transporter. Eur J Pharmacol: 1996; 318 477 484 (Pubitemid 27046294)
19. Jagan Mohan R, Parepally JM R, Mandula H et al. Brain uptake of nonsteroidal anti-inflammatory drugs: ibuprofen, flurbiprofen, and indomethacin. Pharm Res: 2006; 23 873 881 (Pubitemid 43781395)
20. Kalgutkar A S, Crews B C, Rowlinson S W et al. Biochemically based design of cyclooxygenase-2 (COX-2) inhibitors: Facile conversion of nonsteroidal antiinflammatory drugs to potent and highly selective COX-2 inhibitors. PNAS: 2000; 97 925 930 (Pubitemid 30070411)
21. Duos M, Nourrisson M R, Brelet J et al. PetitN-Pyridinyl-indole-3-(alkyl) carboxamides and derivatives as potential systemic and topical inammation inhibitors. Eur J Med Chem: 2001; 36 545 553 (Pubitemid 32781718)
22. Labanauskas L, Udrenaite E, Gaidelis P et al. Synthesis of 5-(2-,3- and 4-methoxyphenyl)-4H-1,2,4-triazole-3-thiol derivatives exhibiting anti-inammatory activity. Farmaco: 2004; 59 255 259 (Pubitemid 38471918)
23. Barsoum F, Georgey H, Abdel-Gawad N. Anti-inflammatory activity and PGE2 inhibitory properties of novel phenylcarbamoylmethyl ester-containing compounds. Molecules: 2009; 14 667 681
24. Halen P K, Murumkar P R, Giridhar R et al. Synthesis, hydrolysis studies and phamacodynamic profiles of amide prodrugs of dexibuprofen with amino acids. Mini-rev Med Chem: 2009; 9 124 139
25. Amir M, Kumar H, Javed S A. Synthesis and pharmacological evaluation of condensed heterocyclic 6-substituted-1, 2, 4-triazolo [3, 4-b]-1, 3, 4-thiadiazole derivatives of naproxen. Bioorg Med Chem Lett: 2007; 17 4504 4508 (Pubitemid 47058954)