660
Views
23
CrossRef citations to date
0
Altmetric
Reviews

Designing prodrugs for the treatment of Parkinson's disease

, , &
Pages 385-406 | Published online: 12 Apr 2012

Bibliography

  • Grosset DG, Grosset KA, Okun MS, Clinician's Desk Reference of Parkinson's Disease. Manson Publishing, LONDON; 2009
  • Savica R, Rocca WA, Ahlskog JE. When does Parkinson's Disease start? Arch Neurol 2010;67:798-801
  • Wolburg H, Lippoldt A. Tight junctions of the blood-brain barrier: development, composition and regulation. Vascul Pharmacol 2002;38:323-37
  • Abbott NJ. Astrocyte–endothelial interactions and blood–brain barrier permeability. J Anat 2002;200:629-38
  • Begley DJ, Brightman MW. Structural and functional aspects of the blood–brain barrier. Prog Drug Res 2003;61:40-78
  • Rautio J, Laine K, Gynther M, Prodrug Approaches for CNS Delivery. AAPS J 2008;10:92-102
  • Ohtsuki S, Terasaki T. Contribution of carrier-mediated transport systems to the blood–brain barrier as a supporting and protecting interface for the brain; importance for CNS drug discoveryand development. Pharm Res 2007;24:1745-58
  • Pardridge WM, Oldendorf WH, Cancilla P, Blood-brain barrier: interface between internal medicine and the brain. Ann Intern Med 1986;105:82-95
  • Pardridge WM. Blood–brain barrier drug targeting: the future of brain drug development. Mol Interv 2003;3:90-105
  • Abbott NJ, Ronnback L, Hansson E. Astrocyte–endothelial interactions at the blood–brain barrier. Nat Rev 2006;7:41-53
  • Malakoutikhah M, Teixido M, Giralt E. Shuttle-mediated drug delivery to the brain. Angew Chem Int Ed 2011;50:7998-8014
  • Terasaki T, Hosoya K. The blood–brain barrier efflux transporters as a detoxifying system for the brain. Adv Drug Deliv Rev 1999;36:195-209
  • Celia C, Cosco D, Paolino D, Nanoparticulate Devices for Brain Drug Delivery. Med Res Rev 2011;31:716-56
  • Denora N, Trapani A, Laquintana V, Recent advances in medicinal chemistry and pharmaceutical technology–strategies for drug delivery to the brain. Curr Top Med Chem 2009;9:182-96
  • Hsieh PW, Hung CF, Fang JY. Current prodrug design for drug discovery. Curr Pharm Des 2009;15:2236-50
  • Pavan B, Dalpiaz A, Ciliberti N, Progress in drug delivery to the central nervous system by the prodrug approach. Molecules 2008;13:1035-65
  • Pardridge WM. Blood–brain barrier delivery. Drug Discov Today 2007;12:54-61
  • Oldendorf WH, Hyman S, Braun L, Blood–brain barrier: penetration of morphine, codeine, heroin, and methadone after carotid injection. Science 1972;178:984-6
  • Bodor N, Buchwald P. Recent advances in the brain targeting of neuropharmaceuticals by chemical delivery systems. Adv Drug Deliv Rev 1999;36:229-54
  • Bodor N, Buchwald P. Barriers to remember: brain-targeting chemical delivery systems and Alzheimer's disease. Drug Discov Today 2002;7:766-74
  • Anderson BD. Prodrugs for improved CNS delivery. Adv Drug Deliv Rev 1996;19:171-202
  • Ohtsuki S, Terasaki T. Contribution of carrier-mediated transport systems to the blood–brain barrier as a supporting and protecting interface for the brain; importance for CNS drug discovery and development. Pharm Res 2007;24:1745-58
  • Tamai I, Tsuji A. Transporter-mediated permeation of drugs across the blood–brain barrier. J Pharm Sci 2000;89:1371-88
  • Cavalli A, Bolognesi ML, Minarini A, Multi-target-directed ligands to combat neurodegenerative diseases. J Med Chem 2008;51:347-72
  • Blandini F, Greenamyre JT. Protective and symptomatic strategies for therapy of Parkinson's. Drugs Today 1999;35:473-83
  • Bodor N, Farag HH. Improved delivery through biological membranes. 13. Brain specific delivery of dopamine with a dihydropyridine-pyridinium salt type redox delivery system. J Med Chem 1983;26:528-34
  • Kao HD, Traboulsi A, Itoh S, Enhancement of the systemic and CNS Specific delivery of L-Dopa by the nasal administration of its water. Soluble prodrugs. Pharm Res 2000;17:978-84
  • Arica B, Kas HS, Moghdam A, Carbidopa, Carbidopa/levodopa-loaded biodegradable microspheres: in vivo evaluation on experimental Parkinsonism in rats. J Control Release 2005;102:689-97
  • Nutt JG, Woodward WR. Levodopa pharmacokinetics and pharmacodynamics in fluctuating parkinsonian patients. Neurology 1986;36:739-44
  • Hardie R, Lees AJ, Stern GM. On-off fluctuations in Parkinson's disease. Brain 1984;107:487-506
  • Quinn N, Parkes JD, Marsden CD. Control of on/off phenomenon by continuous intravenous infusion of levodopa. Neurology 1984;34:1131-6
  • Nutt JG, Carter JH, Lea ES, Motor fluctuations during continuous levodopa infusions in patients with Parkinson's disease. Mov Disord 1997;12:285-92
  • Di Stefano A, Sozio P, Cerasa LS, L-Dopa Prodrugs: an overview of trends for improving Parkinson's disease treatment. Curr Pharm Des 2011;17:3482-93
  • Hauser RA. Early Pharmacologic treatment in Parkinson's disease. Am J Manag Care 2010;16:S100-7
  • Di Stefano A, Sozio P, Iannitelli A, New drug delivery strategies for improved Parkinson's disease therapy. Expert Opin Drug Deliv 2009;6:389-404
  • Bodor N, Sloan KB, Higuchi T, Improved delivery through biological membranes 4: prodrugs of L-dopa. J Med Chem 1977;20:1435-45
  • Marrel C, Boss G, Van De Waterbeemd H, L-Dopa esters as potential prodrugs. Eur J Med Chem Chim Ther 1985;20:459-65
  • Cooper DR, Marrel C, Van De Waterbeemd H, L-Dopa methyl ester-a. candidate for chronic systemic delivery of L-Dopa in Parkinson's disease.. Clin Neuropharmacol 1984;7:89-98
  • Garzon-Aburbeh A, Poupaert JH, Claesen M, A lymphotropic prodrug of L-dopa: synthesis, pharmacological properties, and pharmacokinetic behaviour of 1,3-dihexadecanoyl-2-[(S)-2-amino-3-(3,4-dihydroxyphenyl)propanoyl] propane-1,2,3-triol. J Med Chem 1986;29:687-91
  • Cooper DR, Marrel C, Van De Waterbeemd H, L-dopa esters as potential prodrugs: effect on brain concentration of dopamine metabolites in reserpinized mice. J Pharm Pharmacol 1987;39:809-18
  • Cooper DR, Marrel C, Van De Waterbeemd H, L-dopa esters as potential prodrugs: behavioural activity in experimental models of Parkinson's disease. J Pharm Pharmacol 1987;39:627-35
  • Ihara M, Tsuchiya Y, Sawasaki Y, New potential prodrug to improve the duration of L-dopa: L-3-(3-hydroxy-4-pivaloyloxyphenyl)alanine. J Pharm Sci 1989;78:525-9
  • Ihara M, Nakajima S, Hisaka A, Hydrolysis and acyl migration of a catechol monoester of L-dopa: L-3-(3-hydroxy-4-pivaloyloxyphenyl)alanine. J Pharm Sci 1990;79:703-8
  • Stocchi F, Ruggieri S, Carta A, Intravenous boluses and continuous infusions of L-DOPA methyl ester in fluctuating patients with Parkinson's disease. Mov Disord 1992;7:249-56
  • Djaldetti R, E, Melamed Levodopa ethylester: a novel rescue therapy for response fluctuations in Parkinson's disease. Ann Neurol 1996;39:400-4
  • Brime B, Ballesteros MP, Frutos P. Preparation and in vitro characterization of gelatin microspheres containing Levodopa for nasal administration. J Microencapsul 2000;17:777-84
  • Xiang JN, Zhou CX, Yao F, Inventors. Xenoport, Inc., assignee. Catechol protected levodopa diester prodrugs, compositions, and methods of use. WO2008079387; 2008
  • Xenoport website. Available from: www:xenoport.com/research_development/xp21279.htm
  • Atlas D. L-Dopa Amide derivatives and uses thereof. WO2004069146; 2004
  • Jiang W, Lv L, Zhou S, Simultaneous determination of l-dopa and its prodrug (S)-4-(2-acetamido-3-ethoxy-3-oxopropyl)-1,2-phenylene diacetate in rat plasma by high-performance liquid chromatography–tandem mass spectrometry and its application in a pharmacokinetic study. J Pharm Biomed Anal 2010;53:751-4
  • Zhou T, Hider RC, Jenner P, Design, synthesis and biological evaluation of L-dopa amide derivatives as potential prodrugs for the treatment of Parkinson's disease. Eur J Med Chem 2010;45:4035-42
  • Denora N, Laquintana V, Lopedota A, Novel L-Dopa and dopamine prodrugs containing a 2-Phenyl imidazopyridine moiety. Pharm Res 2007;24:1309-24
  • Eltayb A, Wademberg MLG, Svensson TH. Enhanced cortical dopamine output and antipsycotic-like effect of raclopride with adjunctive low-dose L-Dopa. Biol Psychiatry 2005;58:337-43
  • Langlois M, Quintard D, Abalain C. Synthesis of symmetrical pseudopeptides as potential inhibitors of the human immunodeficiency virus-1 protease. Eur J Med Chem 1994;29:639-47
  • Christiaans JAM, Timmerman H. Cardiovascular hybrid drugs: combination of more than one pharmacological property in one single molecule. Eur J Pharm Sci 1996;4:1-22
  • Mahfouz NM, Aboul-Fadl T, Diab AK. Metronidazole twin ester prodrugs: synthesis, physicochemical properties, hydrolysis kinetics and antigiardial activity. Eur J Med Chem 1998;33:675-83
  • Giannola LI, Giammona G, Alotta R. Pro-drugs of isoniazid: synthesis and diffusion characteristics of acyl derivatives. Pharmazie 1992;47:423-5
  • Ducho C, Gorbig U, Jessel S, BiscycloSal-d4T-monophosphates: drugs that deliver two molecules of bioactive nucleotides. J Med Chem 2007;50:1335-46
  • Felix AM, Winter DP, Wang SS, Synthesis and antireserpine activity of peptides of L-Dopa. J Med Chem 1974;17:422-6
  • Di Stefano A, Mosciatti B, Cingolani GM, Dimeric L-Dopa derivatives as potential prodrugs. Bioorg Med Chem Lett 2001;11:1085-8
  • Cannazza G, Di Stefano A, Mosciatti B, Detection of levodopa, dopamine and its metabolites in rat striatum dialysates following peripheral administration of L-DOPA prodrugs by mean of HPLC–EC. J Pharm Biomed Anal 2005;36:1079-84
  • Di Stefano A, Carafa M, Sozio P, Evaluation of rat striatal l-dopa and DA concentration after intraperitoneal administration of l-dopa prodrugs in liposomal formulations. J Control Release 2004;99:293-300
  • Di Stefano A, Sozio P, Iannitelli A, Maleic- and fumaric-diamides of (O,O-diacetyl)-L-Dopa-methylester as anti-Parkinson prodrugs in liposomal formulation. J Drug Target 2006;14:652-61
  • Cingolani GM, Di Stefano A, Mosciatti B, Synthesis of L-(+)-3-(3-hydroxy-4-pivaloyloxybenzyl)-2,5-diketomorpholine as potential prodrug of L-dopa. Bioorg Med Chem Lett 2000;10:1385-8
  • Giorgioni G, Claudi F, Ruggieri S, Design, synthesis and preliminary pharmacological evaluation of new imidazolinones as L-DOPA prodrugs. Bioorg Med Chem 2010;18:1834-43
  • Rasmussen GJ, Bundgaard H. Prodrugs of peptides. 15. 4-Imidazolidinone prodrug derivatives of enkephalins to prevent aminopeptidase-catalyzed metabolism in plasma and absorptive mucosae. Int J Pharm 1991;76:113-22
  • Ishikura T, Senou T, Ishihara H, Drug delivery to the brain. DOPA prodrugs based on a ring-closure reaction to quaternary thiazolium compounds. Int J Pharm 1995;116:51-63
  • Chemuturi NV, Donovan MD. Role of organic cation transporters in dopamine uptake across olfactory and nasal respiratory tissues. Mol Pharm 2007;4:936-42
  • Casagrande C, Ferrari G. 3,4-0-diacyl derivatives of dopamine. Il Farmaco 1973;28:143-8
  • Borgman RJ, McPhillips JJ, Stitzel RE. Synthesis and pharmacology of centrally acting dopamine derivatives and analogs in relation to Parkinson's disease. J Med Chem 1973;16:630-3
  • Bodor N, Farag HH, Brewster ME. Site-specific, sustained release of drugs to the brain. Science 1981;214:1370-2
  • Prokai L, Prokai-Tatrai K, Bodor N. Targeting drugs to the brain by redox chemical delivery systems. Med Res Rev 2000;20:367-416
  • Carelli V, Liberatore F, Scipione L, New system for the specific delivery and sustained release of dopamine to the brain. J Control Release 1996;42:209-16
  • Missale C, Nash SR, Robinson S, Dopamine receptors: from structure to function. Physiol Rev 1998;78:189-225
  • Uitti RY, Ahlskog JE. Comparative review of dopamine receptor agonists in Parkinson's disease. CNS Drugs 1996;5:369-88
  • Maratos EC, Jackson MJ, Pearce RK, Antiparkinsonian activity and dyskinesia risk of ropinirole and L-DOPA combination therapy in drug naive MPTP-lesioned common marmosets (Callithrix jacchus). Mov Disord 2001;16:631-41
  • Giardina WJ, Williams M. Adrogolide HCl (ABT-431; DAS-431), a Prodrug of the Dopamine D1 Receptor Agonist, A-86929: preclinical Pharmacology and Clinical Data. CNS Drug Rev 2001;7:305-16
  • Shiosaki K, Jenner P, Asin KE, ABT-431: the diacetyl prodrug of A-86929, a potent and selective dopamine D1 receptor agonist: in vitro characterization and effects in animal models of Parkinson's disease. J Pharmacol Exp Ther 1996;276:150-60
  • Rascol O, Blin O, Thalamas C, ABT-431, a D1 receptor agonist prodrug, has efficacy in Parkinson's disease. Ann Neurol 1999;45:736-41
  • Baldessarini RJ, Walton KG, Borgman RJ. Esters of apomorphine and N,N-dimethyldopamine as agonists of dopamine receptors in the rat brain in vivo. Neuropharmacol 1975;14:725-31
  • Borgman RJ, Baldessarini RJ, Walton KG. Diester derivatives as apomorphine prodrugs. J. Med Chem 1976;19:717-19
  • Baldessarini RJ, Kula NS, Walton KG, Hydrolysis of diester prodrugs of apomorphine. Biochem Pharmacol 1977;26:1749-56
  • Dijkstra D, Venhuis BJ, Wikstrom HV, Method for treating Parkinson's disease by administering of (-)-5-keto-2-N,N-di-propylaminotetrahydrotetralin.. WO0128977A1; 2001
  • Venhuis BJ, Wikstrom HV, Rodenhuis N, A new type of prodrug of catecholamines - an opportunity to improve the treatment of Parkinson's Disease. J Med Chem 2002;45:2349-51
  • Liu KS, Sung KC, Al-Suwayeh SA, Enhancement of transdermal apomorphine delivery with a diester prodrug strategy. Eur J Pharm Biopharm 2011;78:422-31
  • Tsai MJ, Huang YB, Wu PC, Oral apomorphine delivery from solid lipid nanoparticles with different monostearate emulsifiers: pharmacokinetic and behavioural evaluations. J Pharm Sci 2011;100:547-57
  • Venhuis BJ, Dijkstra D, Wustrow DJ, Orally active analogues of the dopaminergic prodrug 6-(N,N-di-n-propylamino)-3,4,5,6,7,8-hexahydro-2H-naphthalen-1-one. synthesis and pharmacological activity. J Med Chem 2003;46:584-90
  • Venhuis BJ, Dijkstra D, Wustrow D, Orally active oxime derivatives of the dopaminergic prodrug 6-(N,N-Di-n-propylamino)-3,4,5,6,7,8-hexahydro-2H-naphthalen-1-one. synthesis and pharmacological activity. J Med Chem 2003;46:4136-40
  • Hes J, Sternson LA. The metabolism of acetophenone oxime in rat liver homogenates. Drug Metab Dispos 1974;2:345-50
  • Axelrod LR, Miller LL. The metabolism of testosterone in the isolated perfused dog liver. J Biol Chem 1956;219:455-61
  • Liu D, Wikstroem HV, Dijkstra D, Extremely potent orally active benzo[g]quinoline analogue of the dopaminergic prodrug: 6-(N,N-Di-n-propyl)amino-3,4,5,6,7,8-hexahydro-2H-naphthalen-1-one. J Med Chem 2006;49:1494-8
  • Liu D, Venhuis BJ, Wikstrom HV, Synthesis of supposed enone prodrugs of apomorphine and N-propyl-norapomorphine. Tetrahedron 2007;63:7264-70
  • Woodruff GN, Elkhawad AO, Crossman AR, Further evidence for the stimulation of rat brain dopamine receptors by a cyclic analogue of dopamine. J Pharm Pharmacol 1974;26:740-1
  • Woodruff GN, Elkhawad AO, Pinder RM. Long lasting stimulation of locomotor activity produced by the intraventricular injection of a cyclic analogue of dopamine into conscious mice. Eur J Pharmacol 1974;25:80-6
  • Westerink BH, Dijkstra D, Feenstra MG, Dopaminergic prodrugs: brain concentrations and neurochemical effects of 5,6- and 6,7-ADTN after administration as dibenzoyl esters. Eur J Pharmacol 1980;61:7-15
  • Thorberg SO, Berg S, Lundstrom J, Carbamate ester derivatives as potential prodrugs of the presynaptic dopamine autoreceptor agonist (-)-3-(3-hydroxyphenyl)-N-propylpiperidine. J Med Chem 1987;30:2008-12
  • den Daas I, Tepper PG, Horn AS. Improvement of the oral bioavailability of the selective dopamine agonist N-0437 in rats: the in vitro and in vivo activity of eight ester prodrugs. Naunyn Schmiedebergs Arch Pharmacol 1990;341:186-91
  • den Daas I, Tepper PG, Rollema H, Transdermal administration of the dopamine agonist N-0437 and seven ester prodrugs: comparison with oral administration in the 6-OHDA turning model. Naunyn Schmiedebergs Arch Pharmacol 1990;342:655-9
  • Pavan B, Dalpiaz A. Prodrugs and endogenous transporters: are they suitable tools for drug targeting into the central nervous system? Curr Pharm Des 2011;17:3560-76
  • Gynther M, Ropponen J, Laine K, Glucose promoiety enables glucose transporter mediated brain uptake of ketoprofen and indomethacin prodrugs in rat. J Med Chem 2009;52:3348-53
  • More SS, Vince R. Design, synthesis and biological evaluation of glutathione peptidomimetics as components of anti-Parkinson prodrugs. J Med Chem 2008;51:4581-8
  • Wang H, Lee J, Tsai M, Synthesis and Pharmacological activities of a novel tripeptide mimetic dopamine prodrug. Bioorg Med Chem Lett 1995;5:2195-8
  • Bai JPF, Hu M, Subramanian P, Utilization of peptide carrier system to improve intestinal absorption: targeting prolidase as a prodrug-converting enzyme. J Pharm Sci 1992;81:113-16
  • Pinnen F, Cacciatore I, Cornacchia C, Codrugs linking L-Dopa and Sulfur-containing antioxidants: new pharmacological tools against Parkinson's disease. J Med Chem 2009;52:559-63
  • Minelli A, Conte C, Prudenzi E, N-Acetyl-L-Methionyl-L-Dopa-Methyl Ester as a dual acting drug that relieves L-Dopa-induced oxidative toxicity. Free Radic Biol Med 2010;49:31-9
  • Pinnen F, Cacciatore I, Cornacchia C, Synthesis and study of L-Dopa-Glutathione codrugs as New anti-Parkinson agents with free radical scavenging properties. J Med Chem 2007;50:2506-15
  • Bobrowski K, Hug GL, Pogocki D, Sulfur radical cation-peptide bond complex in the one-electron oxidation of S-methylglutathione. J Am Chem Soc 2007;129:9236-45
  • Pinnen F, Cacciatore I, Cornacchia C, CNS delivery of L-Dopa by a new Hybrid Glutathione-Methionine peptidomimetic prodrug. Amino Acids 2012;42:261-9
  • Anderson BD. Prodrugs for improved CNS delivery. Adv Drug Deliv Rev 1996;19:171-202
  • Prokai L. Peptide drug delivery into the central nervous system. Prog Drug Res 1998;51:95-131
  • Chavis C, Grodenic F, Imbach JL. Ribosides et derives de la L-methyl dopa et de la L-dopa. Eur J Med Chem Chim Ther 1981;16:219-27
  • Bonina F, Puglia C, Rimoli MG, Glycosyl derivatives of dopamine and L-dopa as anti-Parkinson prodrugs: synthesis, pharmacological activity and in vitro stability studies. J Drug Target 2003;11:25-36
  • Yoon S, Fulton DB, Robyt JF. Synthesis of dopamine and L-DOPA-alpha-glycosides by reaction with cyclomaltohexaose catalyzed by cyclomaltodextrin glucanyltransferase. Carbohydr Res 2009;344:2349-56
  • Savolainen J, Leppanen J, Forsberg M, Synthesis and in vitro/in vivo evaluation of novel oral N-alkyl and N,N-dialkylcarbamate esters of entacapone. Life Sci 2000;67:205-16
  • Leppanen J, Huuskonen J, Nevalainen T, Design and Synthesis of a Novel L-Dopa-Entacapone Codrug. J Med Chem 2002;45:1379-82
  • Rautio J, Leppanen J, Lehtonen M, Design, synthesis and in vitro/in vivo evaluation of orally bioavailable prodrugs of a catechol-O-methyltransferase inhibitor. Bioorg Med Chem Lett 2010;20:2614-16
  • Di Stefano A, Sozio P, Iannitelli A, Synthesis and preliminary evaluation of L-Dopa/Benserazide conjugates as dual acting codrugs. Lett Drug Des Discov 2006;3:747-52
  • Giannola LI, De Caro V, Giandalia G, Synthesis and in vitro studies on a potential dopamine prodrug. Pharmazie 2008;63:704-10
  • Fernandez C, Nieto O, Rivas E, Synthesis and biological studies of glycosyl dopamine derivatives as potential antiparkinsonian agents. Carbohydr Res 2000;327:353-65
  • Fernandez C, Nieto O, Fontenla JA, Org. Synthesis of glycosyl derivatives as dopamine prodrugs: interaction with glucose carrier GLUT-1. Biomol Chem 2003;1:767-71
  • Ruocco LA, Viggiano D, Viggiano A, Galactosilated dopamine enters into the brain, blocks mesocorticolimbic system and modulates activity and scanning time in Naples high excitability rats. Neuroscience 2008;152:234-44
  • Juncos JL, Mouradian MM, Fabbrini G, Levodopa methyl ester treatment of Parkinson's disease. Neurology 1987;37:1242-5

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.