Design, synthesis and biological evaluation of brain targeting l-ascorbic acid prodrugs of ibuprofen with "lock-in" function

European Journal of Medicinal Chemistry

Volumn 82, Issue , 2014, Pages 314-323

  Zhao, Yi ^a   Qu, Boyi ^a   Wu, Xueying ^b   Li, Xiaocen ^a   Liu, Qingqing ^a   Jin, Xiuxiu ^a   Guo, Li ^a   Hai, Li ^a   Wu, Yong ^a  

^a SICHUAN UNIVERSITY   (China)

^b SHENYANG PHARMACEUTICAL UNIVERSITY   (China)

Author keywords

Brain targeting; Ibuprofen; l Ascorbic acid; Prodrugs; Synthesis; Thiamine disulfide

Indexed keywords

ASCORBIC ACID; GLUCOSE TRANSPORTER 1; IBUPROFEN; PRODRUG; THIAMINE; SLC23A2 PROTEIN, MOUSE; SODIUM ASCORBIC ACID COTRANSPORTER;

ARTICLE; BLOOD BRAIN BARRIER; BRAIN; DRUG DESIGN; DRUG SCREENING; DRUG SYNTHESIS; DRUG TARGETING; ANIMAL; ANTAGONISTS AND INHIBITORS; CHEMICAL STRUCTURE; DOSE RESPONSE; DRUG DELIVERY SYSTEM; DRUG EFFECTS; INBRED MOUSE STRAIN; METABOLISM; MOUSE; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TISSUE DISTRIBUTION;

ANIMALS; ASCORBIC ACID; BRAIN; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DELIVERY SYSTEMS; DRUG DESIGN; GLUCOSE TRANSPORTER TYPE 1; IBUPROFEN; MICE; MICE, INBRED STRAINS; MOLECULAR STRUCTURE; PRODRUGS; SODIUM-COUPLED VITAMIN C TRANSPORTERS; STRUCTURE-ACTIVITY RELATIONSHIP; TISSUE DISTRIBUTION;

EID: 84902309930     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2014.05.072     Document Type: Article

References (27)

1. J. Bernacki, A. Dobrowolska, and K. Nierwi nska A. Physiology and pharmacological role of the blood-brain barrier Pharmacol. Rep. 60 2008 600 622
2. M. Anne, R. Jarkko, L. Marko, J. Tomi, and S. Jouko Inefficient central nervous system delivery limits the use of ibuprofen in neurode-generative diseases J. Pharm. Sci. 24 2005 101 105
3. H. Mie, O. Kenjiro, N. Hironobu, and Y. Masahito Non-steroidal anti-inflammatory drugs have anti-amyloidogenic effects for Alzheimer's b-amyloidbrils in vitro Neuropharmacology 49 2005 1088 1099
4. P.L. McGeer, and E.G. McGeer NSAIDs and Alzheimer disease: epidemiological, animal model and clinical studies Neurobiol. Aging 28 2007 639 647 (Pubitemid 46349357)
5. S. Weggen, M. Rogers, and J. Eriksen NSAIDs: small molecules for prevention of Alzheimer's disease or precursors for future drug development Trends Pharmacol. Sci. 28 2007 536 543 (Pubitemid 47488508)
6. K.U. Rainer, A.P. Martin, B. Konrad, and W. Manfred Synthesis of antioxidative and anti-inammatory drugs Glucoconjugates Carbohydr. Res. 325 2000 75 80
7. C.S. Ioanna, A.R. Eleni, P.K. Angeliki, C.C. Michael, T. Kariofyllis, and N.K. Panos Design and study of some novel ibuprofen derivatives with potential nootropic and neuroprotective properties Bioorg. Med. Chem. 15 2007 951 961
8. M. Matoga, F. Péhourcq, F. Lagrange, F. Fawaz, and B. Bannwarth Influence of a polymeric formulation of ketoprofen on its diffusion into cerebrospinal fluid in rats J. Pharm. Biomed. 27 2002 881 888 (Pubitemid 34142563)
9. B.A. in't Veld, A. Ruitenberg, and A. Hofman et al. Nonsteroidal antiinflammatory drugs and the risk of Alzheimer's disease N. Engl. J. Med. 345 2001 1515 1521 (Pubitemid 33144916)
10. R.C. Rose, and A.M. Bode Biology of the free radical scavengers: an evaluation of ascorbate FASEB J. 7 1993 1135 1142 (Pubitemid 23271032)
11. R.C. Rose, and A.M. Bode Ocular ascorbate transport and metabolism Comp. Biochem. Physiol. 100 1991 273 285
12. M.E. Rice Ascorbate regulation and its neuroprotective role in the brain Trends Neurosci. 23 2000 209 216 (Pubitemid 30236180)
13. S.C. Rumsey et al. Glucose transporter isoforms GLUT1 and GLUT3 transport dehydroascorbic acid J. Biol. Chem. 272 1997 18982 18989 (Pubitemid 27318253)
14. D.B. Agus et al. Vitamin C crosses the blood-brain barrier in the oxidized from through the glucose transporters J. Clin. Invest. 100 1997 2842 2848 (Pubitemid 28007554)
15. +-dependent L-ascorbic acid transporters Nature 399 1999 70 75
16. S. Manfredini, B. Pavan, and S. Vertuani et al. Design, synthesis and activity of ascorbic acid prodrugs of nipecotic, kynurenic and diclophenamic acids, liable to increase neurotropic activity J. Med. Chem. 45 2002 559 562 (Pubitemid 34145702)
17. Y. Laras, M. Sheha, and N. Pietrancosta et al. Thiazolamide-ascorbic acid conjugate: a γ-secretase inhibitor with enhanced blood-brain barrier permeation Aust. J. Chem. 60 2007 128 132
18. C.P. Corpe, J.H. Lee, and O. Kwon et al. 6-Bromo-6-deoxy-L-ascorbic acid J. Biol. Chem. 280 2005 5211 5220
19. H. Kato, T. Kino, and F. Yamamoto et al. Ascorbate analogs for use in medical imaging: synthesis and radical scavenging activity of 5-O-(4'-iodobenzyl)-L-ascorbic acid Chem. Pharm. Bull. 55 2007 1700 1703 (Pubitemid 350232540)
20. X.Y. Wu, X.C. Li, J. Mi, J. You, and L. Hai Design, synthesis and preliminary biological evaluation of brain targeting L-ascorbic acid prodrugs of ibuprofen Chin. Chem. Lett. 24 2013 117 119
21. F.Q. Zhao, and A.F. Keating Functional properties and genomics of glucose transporters Curr. Genomics 8 2007 113 128 (Pubitemid 46690959)
22. C.C. Portugal, V.S. Miya, K.C. Calaza, R.A.M. Santos, and R.P. Carvalho Glutamate receptors modulate sodium-dependent and calcium-independent vitamin C bidirectional transport in cultured avian retinal cells J. Neurochem. 108 2009 507 520
23. T. Ishikura, T. Senou, H. Ishihara, T. Kato, and T. Ito Drug delivery to the brain. DOPA prodrugs based on a ring-closure reaction to quaternary thiazolium compounds Int. J. Pharm. 116 1995 51 63
24. W. Fan, Y. Wu, X.K. Li, and N. Yao et al. Design, synthesis and biological evaluation of brain-specific glucosyl thiamine disulfide prodrugs of naproxen Eur. J. Med. Chem. 46 2011 3651 3661
25. H.I. Choi, H.J. Kim, J.I. Park, E.H. Shin, D.W. Kim, and S.S. Kim Design and efficient synthesis of novel ascorbyl conjugated peptide with high collagen biosynthesis stimulating effects Bioorg. Med. Chem. Lett. 19 2009 2079 2082
26. H. Kato, T. Kino, F. Yamamoto, T. Kaneshiro, T. Mukai, and M. Maeda Ascorbate analogs for use in medical imaging: synthesis and radical scavenging activity of 5-O-(4'-iodobenzyl)-L-ascorbic acid Chem. Pharm. Bull. 55 2007 1700 1703 (Pubitemid 350232540)
27. H.D. Han, A. Lee, C.K. Song, T. Hwang, H. Seong, C.O. Lee, and B.C. Shin In vivo distribution and antitumor activity of heparin-stabilized doxorubicin-loaded liposomes Int. J. Pharm. 313 2006 181 188