CNS delivery of L-dopa by a new hybrid glutathione-methionine peptidomimetic prodrug

Amino Acids

Volumn 42, Issue 1, 2012, Pages 261-269

  Pinnen, Francesco ^a   Cacciatore, Ivana ^a   Cornacchia, Catia ^a   Mollica, Adriano ^a   Sozio, Piera ^a   Cerasa, Laura S ^a   Iannitelli, Antonio ^a   Fontana, Antonella ^a   Nasuti, Cinzia ^b   Di Stefano, Antonio ^a  

^a UNIVERSITY OF CHIETI   (Italy)

^b UNIVERSITY OF CAMERINO   (Italy)

Author keywords

Glutathione; L Dopa; Methionine; Parkinson's disease

Indexed keywords

1,1 DIPHENYL 2 PICRYLHYDRAZYL; CYSTINE; DIMETHYL SULFOXIDE; GLUTATHIONE; LEVODOPA; METHIONINE; PEPTIDOMIMETIC AGENT; PRODRUG; PEPTIDE;

ANIMAL EXPERIMENT; ANIMAL TISSUE; AQUEOUS SOLUTION; BRAIN TISSUE; CATALYSIS; CENTRAL NERVOUS SYSTEM; CONFERENCE PAPER; CONTROLLED STUDY; CORPUS STRIATUM; DRUG BIOAVAILABILITY; DRUG BLOOD LEVEL; DRUG DELIVERY SYSTEM; DRUG HALF LIFE; DRUG STABILITY; ENZYME STABILITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; MALE; NONHUMAN; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; PROTEIN CLEAVAGE; RAT; STOMACH JUICE; ANIMAL; ARTICLE; CHEMISTRY; HUMAN; KINETICS; METABOLISM; SOLUBILITY; WISTAR RAT;

RATTUS;

ANIMALS; CENTRAL NERVOUS SYSTEM; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; GLUTATHIONE; HUMANS; HYDROLYSIS; KINETICS; LEVODOPA; MALE; METHIONINE; PEPTIDES; PRODRUGS; RATS; RATS, WISTAR; SOLUBILITY;

EID: 84860243286     PISSN: 09394451     EISSN: 14382199     Source Type: Journal    
DOI: 10.1007/s00726-010-0804-z     Document Type: Article

References (35)

1. Angelini G, Cusan C, De Maria P, Fontana A, Maggini M, Pierini M, Prato M, Schergna S, Villani C (2005) The associative properties of some amphiphilic fullerene derivatives. Eur J Org Chem 9:1884-1891 (Pubitemid 40669537)
2. Bai JPF (1995) pGlu-L-Dopa-Pro: a tripeptide prodrug targeting the intestinal peptide transporter for absorption and tissue enzymes for conversion. Pharm Res 12:1101-1104
3. Bajda M, Boryczka S, Wietrzyk J, Malawska B (2007) Investigation of lipophilicity of anticancer-active thioquinoline derivatives. Biomed Chromatogr 21:123-131
4. Bobrowski K, Hug GL, Pogocki D, Marciniak B, Schöneich C (2007) Sulfur radical cation-peptide bond complex in the one-electron oxidation of S-methylglutathione. J Am Chem Soc 129:9236-9245 (Pubitemid 47171872)
5. Bodor N, Sloan KB, Higuchi T, Sasaha K (1977) Improved delivery through biological membranes. 4. Prodrugs of L-DOPA. J Med Chem 20:1435-1445 (Pubitemid 8209552)
6. Bonina F, Lanza M, Montenegro L, Puglisi G, Tomaino A, Trombetta D, Castelli F, Saija A (1996) Flavonoids as potential protective agents against photo-oxidative skin damage. Int J Pharm 145:87-94 (Pubitemid 27062989)
7. Burini G, Coli R (2004) Determination of formaldehyde in spirits by high-performance liquid chromatography with diode-array detection after derivatization. Anal Chim Acta 511:155-158 (Pubitemid 38569920)
8. Cingolani GM, Di Stefano A, Mosciatti B, Napolitani F, Giorgioni G, Ricciutelli M, Claudi F (2000) Synthesis of L-(+)-3-(3-hydroxy- 4-pivaloyloxybenzyl)-2, 5-diketomorpholine as potential prodrug of L-dopa. Bioorg Med Chem Lett 10:1385-1388 (Pubitemid 30391975)
9. Cooper DR, Marrel C, Van De Waterbeemd H, Quinn N, Testa B, Jenner P, Marsden CD (1984) L-Dopa methyl ester-a candidate for chronic systemic delivery of L-dopa in Parkinson's disease. Clin Neuropharmacol 7:89-98 (Pubitemid 14138570)
10. Cooper DR, Marrel C, Van De Waterbeemd H, Testa B, Jenner P, Marsden CD (1987) L-Dopa esters as potential prodrugs: effect on brain concentration of dopamine metabolites in reserpinized mice. J Pharm Pharmacol 39:809-818 (Pubitemid 18012990)
11. Di Stefano A, Sozio P, Cocco A, Iannitelli A, Santucci E, Costa M, Pecci L, Nasuti C, Cantalamessa F, Pinnen F (2006) L-Dopa- and dopamine-(R)-a-Lipoic acid conjugates as multifunctional codrugs with antioxidant properties. J Med Chem 49:1486-1493 (Pubitemid 43271901)
12. Di Stefano A, Sozio P, Iannitelli A, Cerasa LS, Fontana A, Di Biase G, D'Amico G, Di Giulio M, Carentiero C, Grumetto L, Barbato F (2008) Characterization of alkanoyl-10-O-minocyclines in micellar dispersions as potential agents for treatment of human neurodegenerative disorders. Eur J Pharm Sci 34:118-128
13. Everts M, Schraa AJ, de Leij LFMH, Meijer DKF, Molema G (2001) Brain-specific drug targeting strategies. In: Molema G, Meijer DKF (eds) Drug targeting-organ specific strategies. Wiley-VCH, Weinheim, pp 23-52
14. Garzon-Aburbeh A, Poupaert JH, Claesen M, Dumont PA (1986) Lymphotropic prodrug of L-dopa: synthesis, pharmacological properties, and pharmacokinetic behavior of 1, 3-dihexadecanoyl- 2-[(S)-2-amino-3-(3, 4-dihydroxyphenyl)prop anoyl] propane- 1, 2, 3-triol. J Med Chem 29:687-691 (Pubitemid 16034677)
15. Giorgioni G, Claudi F, Ruggieri S, Ricciutelli M, Palmieri GF, Di Stefano A, Sozio P, Cerasa LS, Chiavaroli A, Ferrante C, Orlando G, Glennon RA (2010) Design, synthesis and preliminary pharmacological evaluation of new imidazolinones as L-DOPA prodrugs. Bioorg Med Chem 18:1834-1843
16. Ihara M, Tsuchiya Y, Sawasaki Y, Hisaka A, Takehana H, Tomimoto K, Yano MA (1989) New potential prodrug to improve the duration of L-dopa: L-3-(3-hydroxy-4-pivaloyloxyphenyl)-alanine. J Pharm Sci 78:525-529 (Pubitemid 20099187)
17. Koller WC, Hutton JT, Tolosa E, Capilldeo R (1999) Immediaterelease and controlled-release carbidopa/levodopa in PD: a 5-year randomized multicenter study. Neurology 53:1012-1019 (Pubitemid 29442117)
18. LeWitt PA (2008) Levodopa for the treatment of Parkinson's disease. N Engl J Med 359:2468-2476
19. Madhukar M, Sawraj S, Dev Sharma P (2010) Design, synthesis and evaluation of mutual prodrug of 4-biphenylacetic acid and quercetin tetramethyl ether (BPAeQTME) as gastrosparing NSAID. Eur J Med Chem 45:2591-2596
20. Malakoutikhah M, Teixidó M, Giralt E (2008) Toward an optimal blood-brain barrier shuttle by synthesis and evaluation of peptide libraries. J Med Chem 51:4881-4889
21. Marrel C, Boss G, Van De Waterbeemd H, Testa B, Cooper D, Jenner P, Marsden CD (1985) L-Dopa esters as potential prodrugs. Eur J Med Chem-Chim Ther 20:459-465
22. Melagraki G, Afantitis A, Igglessi-Markopoulou O, Detsi A, Koufaki M, Kontogiorgis C, Hadjipavlou-Litina DJ (2009) Synthesis and evaluation of the antioxidant and anti-inflammatory activity of novel coumarin-3-aminoamides and their alpha-lipoic acid adducts. Eur J Med Chem 44:3020-3026
23. More SS, Vince R (2008) Design, synthesis and biological evaluation of glutathione peptidomimetics as components of anti-Parkinson prodrugs. J Med Chem 51:4581-4588
24. Nash T (1953) The colorimetric estimation of formaldehyde by means of the Hantzsch reaction. Biochem J 55:416-421
25. Panteleon V, Kostakis IK, Marakos P, Pouli N, Andreadou I (2008) Synthesis and free radical scavenging activity of some new spiropyranocoumarins. Bioorg Med Chem Lett 18:5781-5784
26. Pardridge WM (2009) Alzheimer's disease drug development and the problem of the blood-brain barrier. Alzheimers Dement 5:427-432
27. Pinnen F, Cacciatore I, Cornacchia C, Sozio P, Iannitelli A, Costa M, Pecci L, Nasuti C, Cantalamessa F, Di Stefano A (2007) Synthesis and study of L-dopa-Glutathione codrugs as new anti- Parkinson agents with free radical scavenging properties. J Med Chem 50:2506-2515 (Pubitemid 46799262)
28. Pinnen F, Cacciatore I, Cornacchia C, Sozio P, Cerasa LS, Iannitelli A, Nasuti C, Cantalamessa F, Sekar D, Gabbianelli R, Falcioni ML, Di Stefano A (2009) Codrugs linking L-dopa and sulphurcontaining antioxidants: new pharmacological tools against Parkinson's disease. J Med Chem 52:559-564
29. Smith TS, Parker WD, Bennet JP (1994) L-Dopa increases nigral production of hydroxyl radicals in vivo: potential L-dopa toxicity? Neuroreport 5:1009-1011
30. Sozio P, Iannitelli A, Cerasa LS, Cacciatore I, Cornacchia C, Giorgioni G, Ricciutelli M, Nasuti C, Cantalamessa F, Stefano Di (2008) A new L-dopa codrugs as potential antiparkinson agents. Arch Pharm 341:412-417
31. Sozio P, D'Aurizio E, Iannitelli A, Cataldi A, Zara S, Cantalamessa F, Nasuti C, Di Stefano A (2010) Ibuprofen and lipoic acid diamides as potential codrugs with neuroprotective activity. Arch Pharm 343:133-142
32. Stöber P, Schelhaas M, Nägele E, Hagenbuch P, Rétey J, Waldmann H (1997) Synthesis of characteristic lipopeptides of the human N-Ras protein and their evaluation as possible inhibitors of protein farnesyl transferase. Bioorg Med Chem 5:75-83 (Pubitemid 27065351)
33. Vailaya A, Horváth C (1998) Exothermodynamic relationships in liquid chromatography. J Phys Chem B 102:701-718 (Pubitemid 128606339)
34. Wang H, Lee J, Tsai M, Lu H, Hsu W (1995) Synthesis and pharmacological activities of a novel tripeptide mimetic dopamine prodrug. Bioorg Med Chem Lett 5:2195-2198
35. Yalkowsky SH, Morozowich W (1980) A physical chemical basis for the design of orally active prodrugs. In: Ariens EJ (ed) Drug design, vol 9. Academic Press, New York, pp 121-135