Synthesis, in vitro and in vivo characterization of glycosyl derivatives of ibuprofen as novel prodrugs for brain drug delivery

Journal of Drug Targeting

Volumn 17, Issue 4, 2009, Pages 318-328

  Chen, Qian ^a   Gong, Tao ^a   Liu, Jie ^a   Wang, Xiuli ^a   Fu, Hualin ^a   Zhang, Zhirong ^a  

^a SICHUAN UNIVERSITY   (China)

Author keywords

Alzheimers disease; BBB; Glycosyl derivatives; Prodrug

Indexed keywords

2 [2 (4 ISOBUTYLPHENYL)PROPANOYL)ALPHA,BETA DEXTRO GLUCOPYRANSIDE; 3 [2 (4 ISOBUTYLPHENYL)PROPANOYL]ALPHA,BETA DEXTRO GLUCOPYRANSIDE; 4 [2 (4 ISOBUTYLPHENYL)PROPANOYL]ALPHA,BETA DEXTRO GLUCOPYRANSIDE; 6 [2 (4 ISOBUTYLPHENYL)PROPANOYL]ALPHA,BETA DEXTRO GLUCOPYRANSIDE; ESTER; ESTERASE; GLUCOSE; IBUPROFEN; PRODRUG; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; AREA UNDER THE CURVE; ARTICLE; BLOOD BRAIN BARRIER; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; DRUG BIOAVAILABILITY; DRUG BLOOD LEVEL; DRUG CONJUGATION; DRUG DELIVERY SYSTEM; DRUG DISTRIBUTION; DRUG PENETRATION; DRUG STABILITY; DRUG STRUCTURE; DRUG SYNTHESIS; HETERONUCLEAR MULTIPLE QUANTUM COHERENCE; IN VITRO STUDY; IN VIVO STUDY; NONHUMAN; PH MEASUREMENT; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; RAT;

ALZHEIMER DISEASE; ANIMALS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; AREA UNDER CURVE; BLOOD-BRAIN BARRIER; BRAIN; DRUG DELIVERY SYSTEMS; DRUG STABILITY; GLUCOSE; HYDROGEN-ION CONCENTRATION; IBUPROFEN; PERMEABILITY; PRODRUGS; RATS; RATS, SPRAGUE-DAWLEY;

EID: 70749139129     PISSN: 1061186X     EISSN: 10292330     Source Type: Journal    
DOI: 10.1080/10611860902795399     Document Type: Article

References (22)

1. Alexis S, Pavel I, Felipe Z, Juan CV, Jorge F. 2004. Predicting the three-dimensional structure of the human facilitative glucose transporter GLUT1 by a novel evolutionary homology strategy: insights on the molecular mechanism of substrate migration, and binding sites for glucose and inhibitory molecules. Biophys J, 87, 2990-2999.
2. Anne M, Jarkko R, Marko L, Tomi J, Jouko S. 2005. Inefficient central nervous system delivery limits the use of ibuprofen in neurodegenerative diseases. J Pharm Sci, 24, 101-105.
3. Battaglia G, La Russa M, Bruno V, Arenare L, Ippolito R, Copani A, Bonina F, Nicoletti F. 2000. Systemically administered d-glucose conjugates of 7-chlorokynurenic acid are centrally available and exert anticonvulsant activity in rodents. Brain Res, 860, 149-156.
4. Caridad F, Ofelia N, Emilia R, Gisela M, José AF, Alfonso FM. 2000. Synthesis and biological studies of glycosyl dopamine derivatives as potential antiparkinsonian agents. Carbohydr Res, 327, 353-365.
5. Choeiri C, Staines W, Messier C. 2002. Immunohistochemical localization and quantification of glucose transporters in the mouse brain. Neuroscience, 111, 19-34.
6. Francesco B, Carmelo P, Maria GR, Lucia A, Enrico A, Giampiero B, Maria N, Rosaria M, Michele A, Paolo de C. 2002. Synthesis and in vitro chemical and enzymatic stability of glycosyl 3-azido-3- deoxythymidine derivatives as potential anti-HIV agents. Eur J Pharm Sci, 16, 167-174.
7. Francesco B, Carmelo P, Maria GR, Daniela M, Giampiero B, Maria N, Antonio C, Giovanna LR, Paolo De C. 2003. Glycosyl derivatives of dopamine and l-dopa as anti-Parkinson prodrugs: Synthesis, pharmacological activity and in vitro stability studies. J Drug Target, 11, 25-36.
8. Francesco PB, Loredana A, Rosa I, Gianpiero B, Giuseppe B, Valeria B, Paolo de C. 2000. Synthesis, pharmacokinetics and anticonvulsant activity of 7-chlorokynurenic acid prodrugs. Int J Pharm, 202, 79-88.
9. Francisco N, Alejandro G, Karin R. 1999. Expression of the hexose transporters GLUT1 and GLUT2 during the early development of the human brain. Brain Res, 824, 97-104.
10. Hanashima S, Mizushina Y, Yamazaki T, Ohta K, Takahashi S, Sahara H, Sakaguchi K, Sugawara F. 2001. Synthesis of sulfoquinovosylacyglycerols, inhibitors of eukaryotic DNA polymerase and. Biol Med Chem, 9, 367-376. (Pubitemid 32244035)
11. Ioanna CS, Eleni AR, Angeliki PK, Michael CC, Kariofyllis T, Panos NK. 2007. Design and study of some novel ibuprofen derivatives with potential nootropic and neuroprotective properties. Bioorg Med Chem, 15, 951-961.
12. Matoga M, Péhourcq F, Lagrange F, Fawaz F, Bannwarth B. 2002. Influence of a polymeric formulation of ketoprofen on its diffusion into cerebrospinal fluid in rats. J Pharmaceut Biomed, 27, 881-888.
13. Mehdi A, Geoffrey DH, Christophe M, William DR, Jing Y. 1999. Synthesis of symmetrical 4,4Œ- and 6,6Œ-bis(d-glucose)-based probes as tools for the study of d-glucose transport proteins. Tetrahed Lett, 40, 5861-5864.
14. Mie H, Kenjiro O, Hironobu N, Masahito Y. 2005. Non-steroidal anti-inflammatory drugs have anti-amyloidogenic effects for Alzheimer's b-amyloid fibrils in vitro. Neuropharmacology, 49, 1088-1099.
15. Per JG, Hans H, Stefan W. 1982. A novel reductive ring-opening of carbohydrate benzylidene acetals. Carbohydr Res, 108, 97-101.
16. Polt B, Porreca F, Szabo LZ. 1994. Glycopeptide enkephalin analogues produce analgesia in mice: Evidence for penetration of the blood-brain barrier. Proc Natl Acad Sci USA, 91, 7114-7118.
17. Qian Y, Ming L, Qin JY, Jin SY. 2007. Silver (I) oxide-mediated regioselective 2-monoacylation in 3-O-benzyl-a-L-rhamnopyranosides and application in synthesis of a protected tetrasaccharide fragment of potent cytotoxic saponins gleditsiosides C and D. Carbohydr Res, 342, 1175-1181.
18. Rainer KU, Martin AP, Konrad B, Manfred W. 2000. Synthesis of antioxidative and anti-inflammatory drugs. Glucoconjugates Carbohydr Res, 325, 75-80.
19. Sascha W, Mark R, Jason E. 2007. NSAIDs: Small molecules for prevention of Alzheimer's disease or precursors for future drug development? Trends Pharmacol Sci, 28, 536-543.
20. Thérèse H, Monique S, Kostas A, Daniel S. 1996. Synthesis of glucosechlorambucil derivatives and their recognition by the human GLUT1 glucose transporter. Eur J Pharmacol, 318, 477-484.
21. Thérèse H, Monique S, Kostas A, Daniel S. 1997. Synthesis of O-methylsulfonyl derivatives of d-glucose as potential alkylating agents for targeted drug delivery to the brain. Evaluation of their interaction with the human erythrocyte GLUT1 hexose transporter. Carbohydr Res, 299, 15-21.
22. Zhi RZ, Wei ZL, Nagai T. 2001. Studies on hydrolysis kinetics and photolysis kinetics of N1-retinoyl-5-fluorouracil. STP Pharma Sci, 11, 243-246.