Brain-specific delivery of dopamine mediated by N, N-dimethyl amino group for the treatment of Parkinson's disease

Molecular Pharmaceutics

Volumn 11, Issue 9, 2014, Pages 3174-3185

  Li, Yanping ^a   Zhou, Yangyang ^a   Qi, Bowen ^a   Gong, Tao ^a   Sun, Xun ^a   Fu, Yao ^a   Zhang, Zhirong ^a  

^a SICHUAN UNIVERSITY   (China)

Author keywords

brain targeting; dopamine; lipophilic derivatization; N, N dimethyl amino group; Parkinson's disease

Indexed keywords

DOPAMINE; LIGAND; OXIDOPAMINE;

ANIMAL; APOPTOSIS; BRAIN; CORPUS STRIATUM; DRUG EFFECTS; ENDOTHELIUM CELL; HUMAN; MOUSE; NEUROBLASTOMA; PARKINSON DISEASE; RAT; SPRAGUE DAWLEY RAT; TUMOR CELL LINE;

ANIMALS; APOPTOSIS; BRAIN; CELL LINE, TUMOR; CORPUS STRIATUM; DOPAMINE; ENDOTHELIAL CELLS; HUMANS; LIGANDS; MICE; NEUROBLASTOMA; OXIDOPAMINE; PARKINSON DISEASE; RATS; RATS, SPRAGUE-DAWLEY;

EID: 84906920666     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/mp500352p     Document Type: Article

References (35)

1. Serra, P. A.; Esposito, G.; Enrico, P.; Mura, M. A.; Migheli, R.; Delogu, M. R.; Miele, M.; Desole, M. S.; Grella, G.; Miele, E. Manganese increases L-DOPA auto-oxidation in the striatum of the freely moving rat: Potential implications to L-DOPA long-term therapy of Parkinson's disease Br. J. Pharmacol. 2000, 130 (4) 937-945
2. Olanow, C. W.; Schapira, A. H. Therapeutic prospects for Parkinson disease Ann. Neurol. 2013, 74 (3) 337-347
3. Kao, H. D.; Traboulsi, A.; Itoh, S.; Dittert, L.; Hussain, A. Enhancement of the systemic and CNS specific delivery of L-dopa by the nasal administration of its water soluble prodrugs Pharm. Res. 2000, 17 (8) 978-984
4. Olanow, C. W. Levodopa/dopamine replacement strategies in Parkinson's disease - Future directions Mov. Disord. 2008, 23 (Suppl 3) S613-S622
5. Ossig, C.; Reichmann, H. Treatment of Parkinson's disease in the advanced stage J. Neural Transm. 2013, 120 (4) 523-529
6. Zhou, T.; Hider, R. C.; Jenner, P.; Campbell, B.; Hobbs, C. J.; Rose, S.; Jairaj, M.; Tayarani-Binazir, K. A.; Syme, A. Design, synthesis and biological evaluation of peptide derivatives of L-dopa as anti-Parkinsonian agents Bioorg. Med. Chem. Lett. 2013, 23 (19) 5279-5282
7. Warren Olanow, C.; Kieburtz, K.; Rascol, O.; Poewe, W.; Schapira, A. H.; Emre, M.; Nissinen, H.; Leinonen, M.; Stocchi, F. Factors predictive of the development of Levodopa-induced dyskinesia and wearing-off in Parkinson's disease Mov. Disord. 2013, 28 (8) 1064-1071
8. Carelli, V.; Liberatore, F.; Scipione, L.; Impicciatore, M.; Barocelli, E.; Cardellini, M.; Giorgioni, G. New systems for the specific delivery and sustained release of dopamine to the brain J. Controlled Release 1996, 42 (3) 209-216
9. Denora, N.; Trapani, A.; Laquintana, V.; Lopedota, A.; Trapani, G. Recent advances in medicinal chemistry and pharmaceutical technology-strategies for drug delivery to the brain Curr. Top. Med. Chem. 2009, 9 (2) 182-196
10. Bonina, F.; Puglia, C.; Rimoli, M. G.; Melisi, D.; Boatto, G.; Nieddu, M.; Calignano, A.; Rana, G. L.; Caprariis, P. d. Glycosyl derivatives of dopamine and L-dopa as anti-Parkinson prodrugs: synthesis, pharmacological activity and in vitro stability studies J. Drug Target. 2003, 11 (1) 25-36
11. Fernández, C.; Nieto, O.; Rivas, E.; Montenegro, G.; Fontenla, J. A.; Fernández-Mayoralas, A. Synthesis and biological studies of glycosyl dopamine derivatives as potential antiparkinsonian agents Carbohydr. Res. 2000, 327 (4) 353-365
12. Dalpiaz, A.; Filosa, R.; de Caprariis, P.; Conte, G.; Bortolotti, F.; Biondi, C.; Scatturin, A.; Prasad, P. D.; Pavan, B. Molecular mechanism involved in the transport of a prodrug dopamine glycosyl conjugate Int. J. Pharm. 2007, 336 (1) 133-139
13. Peura, L.; Malmioja, K.; Huttunen, K.; Leppänen, J.; Hämäläinen, M.; Forsberg, M. M.; Rautio, J.; Laine, K. Design, synthesis and brain uptake of LAT1-targeted amino acid prodrugs of dopamine Pharm. Res. 2013, 30 (10) 2523-2537
14. Denora, N.; Laquintana, V.; Lopedota, A.; Serra, M.; Dazzi, L.; Biggio, G.; Pal, D.; Mitra, A. K.; Latrofa, A.; Trapani, G.; Liso, G. Novel L-Dopa and dopamine prodrugs containing a 2-phenyl-imidazopyridine moiety Pharm. Res. 2007, 24 (7) 1309-1324
15. Zhang, X.; Liu, X.; Gong, T.; Sun, X.; Zhang, Z.-r. In vitro and in vivo investigation of dexibuprofen derivatives for CNS delivery Acta Pharmacol. Sin. 2012, 33 (2) 279-288
16. Zhang, Q.; Liang, Z.; Chen, L.; Sun, X.; Gong, T.; Zhang, Z. Novel brain targeting prodrugs of naproxen based on dimethylamino group with various linkages Arzneim.-Forsch. 2012, 62 (06) 261-266
17. Chemuturi, N. V.; Donovan, M. D. Role of organic cation transporters in dopamine uptake across olfactory and nasal respiratory tissues Mol. Pharmaceutics 2007, 4 (6) 936-942
18. Hu, K.; Shi, Y.; Jiang, W.; Han, J.; Huang, S.; Jiang, X. Lactoferrin conjugated PEG-PLGA nanoparticles for brain delivery: Preparation, characterization and efficacy in Parkinson's disease Int. J. Pharm. 2011, 415 (1-2) 273-283
19. Wen, Z.; Yan, Z.; Hu, K.; Pang, Z.; Cheng, X.; Guo, L.; Zhang, Q.; Jiang, X.; Fang, L.; Lai, R. Odorranalectin-conjugated nanoparticles: Preparation, brain delivery and pharmacodynamic study on Parkinson's disease following intranasal administration J. Controlled Release 2011, 151 (2) 131-138
20. Bodor, N.; Farag, H. H. Improved delivery through biological membranes. 13. Brain-specific delivery of dopamine with a dihydropyridine ⇌ pyridinium salt type redox delivery system J. Med. Chem. 1983, 26 (4) 528-534
21. Xie, L.; Hu, L.-F.; Teo, X. Q.; Tiong, C. X.; Tazzari, V.; Sparatore, A.; Del Soldato, P.; Dawe, G. S.; Bian, J.-S. Therapeutic effect of hydrogen sulfide-releasing L-Dopa derivative ACS84 on 6-OHDA-induced Parkinson's disease rat model PloS One 2013, 8 (4) e60200
22. Deguchi, Y.; Miyakawa, Y.; Sakurada, S.; Naito, Y.; Morimoto, K.; Ohtsuki, S.; Hosoya, K.-i.; Terasaki, T. Blood-brain barrier transport of a novel μ1-specific opioid peptide, H-Tyr-d-Arg-Phe-β-Ala-OH (TAPA) J. Neurochem. 2003, 84 (5) 1154-1161
23. Yamazaki, M.; Terasaki, T.; Yoshioka, K.; Nagata, O.; Kato, H.; Ito, Y.; Tsuji, A. Carrier-mediated transport of H1-antagonist at the blood-brain barrier: A common transport system of H1-antagonists and lipophilic basic drugs Pharm. Res. 1994, 11 (11) 1516-1518
24. Yamazaki, M.; Terasaki, T.; Yoshioka, K.; Nagata, O.; Kato, H.; Ito, Y.; Tsuji, A. Carrier-mediated transport of H1-antagonist at the blood-brain barrier: Mepyramine uptake into bovine brain capillary endothelial cells in primary monolayer cultures Pharm. Res. 1994, 11 (7) 975-978
25. Okura, T.; Ito, R.; Ishiguro, N.; Tamai, I.; Deguchi, Y. Blood-brain barrier transport of pramipexole, a dopamine D2 agonist Life Sci. 2007, 80 (17) 1564-1571
26. Okura, T.; Hattori, A.; Takano, Y.; Sato, T.; Hammarlund-Udenaes, M.; Terasaki, T.; Deguchi, Y. Involvement of the Pyrilamine Transporter, a Putative Organic Cation Transporter, in Blood-Brain Barrier Transport of Oxycodone Drug Metab. Dispos. 2008, 36 (10) 2005-2013
27. Pardridge, W. M.; Sakiyama, R.; Fierer, G. Transport of propranolol and lidocaine through the rat blood-brain barrier. Primary role of globulin-bound drug J. Clin. Invest. 1983, 71 (4) 900
28. Kung, H. F.; Blau, M. Regional intracellular pH shift: a proposed new mechanism for radiopharmaceutical uptake in brain and other tissues J. Nucl. Med. 1980, 21 (2) 147-152
29. Kung, H. F.; Tramposch, K. M.; Blau, M. A new brain perfusion imaging agent:[I-123] HIPDM: N,N,N′-trimethyl-N′-[2-hydroxy-3-methyl-5- iodobenzyl]-1,3-propanediamine J. Nucl. Med. 1983, 24 (1) 66-72
30. Borgman, R. J.; McPhillips, J. J.; Stitzel, R. E.; Goodman, I. J. Synthesis and pharmacology of centrally acting dopamine derivatives and analogs in relation to Parkinson's disease J. Med. Chem. 1973, 16 (6) 630-633
31. Shin, K. S.; Choi, H. S.; Zhao, T. T.; Suh, K. H.; Kwon, I. H.; Choi, S. O.; Lee, M. K. Neurotoxic effects of berberine on long-term L-DOPA administration in 6-hydroxydopamine-lesioned rat model of Parkinson's disease Arch. Pharm. Res. 2013, 36 (6) 759-67
32. Le, W.; Jankovic, J.; Xie, W.; Appel, S. Antioxidant property of pramipexole independent of dopamine receptor activation in neuroprotection J. Neural Transm. 2000, 107 (10) 1165-1173
33. Gómez-Santos, C.; Ferrer, I.; Santidrián, A. F.; Barrachina, M.; Gil, J.; Ambrosio, S. Dopamine induces autophagic cell death and α-synuclein increase in human neuroblastoma SH-SY5Y cells J. Neurosci. Res. 2003, 73 (3) 341-350
34. Asanuma, M.; Miyazaki, I.; Ogawa, N. Dopamine-or L-DOPA-induced neurotoxicity: The role of dopamine quinone formation and tyrosinase in a model of Parkinson's disease Neurotox. Res. 2003, 5 (3) 165-176
35. Lai, C.-T.; Yu, P. H. Dopamine-and L-β-3,4-dihydroxyphenylalanine hydrochloride (L-DOPA)-induced cytotoxicity towards catecholaminergic neuroblastoma SH-SY5Y cells: Effects of oxidative stress and antioxidative factors Biochem. Pharmacol. 1997, 53 (3) 363-372