Enhancement of transdermal apomorphine delivery with a diester prodrug strategy

European Journal of Pharmaceutics and Biopharmaceutics

Volumn 78, Issue 3, 2011, Pages 422-431

  Liu, Kuo Sheng ^a   Sung, K C ^a   Al Suwayeh, Saleh A ^b   Ku, Ming Chuan ^c   Chu, Chin Chen ^d   Wang, Jhi Joung ^d   Fang, Jia You ^b,c,e  

^a CHIA NAN UNIVERSITY OF PHARMACY AND SCIENCE   (Taiwan)

^b KING SAUD UNIVERSITY   (Saudi Arabia)

^c CHANG GUNG UNIVERSITY   (Taiwan)

^d CHI MEI MEDICAL CENTER   (Taiwan)

^e CHANG GUNG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Taiwan)

Author keywords

Apomorphine; Diesters; Lipid emulsions; Prodrugs; Skin; Transdermal delivery

Indexed keywords

APOMORPHINE; ESTERASE; GLYCEROL; HYDROCHLORIC ACID; LIPID EMULSION; POLYETHYLENE; PRODRUG;

ANIMAL EXPERIMENT; AQUEOUS SOLUTION; ARTICLE; CONTROLLED STUDY; DRUG DELIVERY SYSTEM; EPIDERMIS; FEMALE; HOMOGENATE; HYDROLYSIS; IN VITRO STUDY; LIPOPHILICITY; MOUSE; NONHUMAN; PARTITION COEFFICIENT; PLASMA; STRATUM CORNEUM; TRANSDERMAL DRUG ADMINISTRATION;

ADMINISTRATION, CUTANEOUS; ANIMALS; ANTIPARKINSON AGENTS; APOMORPHINE; CATTLE; DRUG DELIVERY SYSTEMS; ESTERS; HAIR; HOOF AND CLAW; HUMANS; KERATINS, HAIR-SPECIFIC; PERMEABILITY; PRODRUGS; SKIN; SKIN ABSORPTION; WATER;

EID: 79960570568     PISSN: 09396411     EISSN: 18733441     Source Type: Journal    
DOI: 10.1016/j.ejpb.2011.01.024     Document Type: Article

References (42)

1. M. Stacy, and D. Silver Apomorphine for the acute treatment of "off" episodes in Parkinson's disease Parkinsonism Relat. Disord. 14 2008 85 92
2. J.A. Subramony Apomorphine in dopaminergic therapy Mol. Pharm. 3 2006 380 385 (Pubitemid 44351920)
3. M. Danhof, R. Van der Geest, T. Van Laar, and H.E. Boddé An integrated pharmacokinetic-pharmacodynamic approach to optimization of R-apomorphine delivery in Parkinson's disease Adv. Drug Deliv. Rev. 33 1998 203 263
4. G.L. Li, J.J. de Vries, T.J. van Steeg, H. van den Bussche, H.J. Maas, H.J.E.M. Reeuwijk, M. Danhof, J.A. Bouwstra, and T. van Laar Transdermal iontophoretic delivery of apomorphine in patients improved by surfactant formulation pretreatment J. Control. Release 101 2005 199 208 (Pubitemid 39600983)
5. R. Van der Geest, M. Danhof, and H.E. Boddé Validation and testing of a new iontophoretic continuous flow through transport cell J. Control. Release 51 1998 85 91 (Pubitemid 28064647)
6. F.P. Bonina, C. Puglia, T. Barbuzzi, P. de Caprariis, F. Palagiano, M.G. Rimoli, and A. Saija In vitro and in vivo evaluation of polyoxyethylene esters as dermal prodrugs of ketoprofen naproxen and diclofenac Eur. J. Pharm. Sci. 14 2001 123 134
7. J. Rautio, H. Kumpulainen, T. Heimbach, R. Oliyai, D. Oh, T. Järvinen, and J. Savolainen Prodrugs: design and clinical applications Nat. Drug Discov. 7 2008 255 270 (Pubitemid 351324639)
8. X. He, D. Wang, X. Zhang, A. Li, X. Gu, F. Ding, and J. Zhou Prolonged modulation of FGF-2 expression astrocytic cultures induced by O,O′-diacetyl-apomorphine Biochem. Biophys. Res. Commun. 369 2008 824 929
9. J.Y. Fang, and Y.L. Leu Prodrug strategy for enhancing drug delivery via skin Curr. Drug Discov. Technol. 3 2006 211 224
10. L. Montenegro, C. Carbone, C. Maniscalco, D. Lambusta, G. Nicolosi, C.A. Ventura, and G. Puglisi In vitro evaluation of quercetin-3-O-acyl esters as topical prodrugs Int. J. Pharm. 336 2007 257 262 (Pubitemid 46670651)
11. T.L. Hwang, Y.K. Lin, C.H. Chi, T.H. Huang, and J.Y. Fang Development and evaluation of perfluorocarbon nanobubbles for apomorphine delivery J. Pharm. Sci. 98 2009 3735 3747
12. R.J. Borgman, R.J. Baldessarini, and K.G. Walton Diester derivatives as apomorphine prodrugs J. Med. Chem. 19 1976 717 719
13. J.J. Wang, K.C. Sung, C.H. Yeh, and J.Y. Fang The delivery and antinociceptive effects of morphine and its ester prodrugs from lipid emulsions Int. J. Pharm. 353 2008 95 104
14. W.R. Lee, S.C. Shen, K.H. Wang, C.H. Hu, and J.Y. Fang Lasers and microdermabrasion enhance and control topical delivery of vitamin C. J. Invest. Dermatol. 121 2003 1118 1125
15. H.J. Doh, W.J. Cho, C.S. Yong, H.G. Choi, J.S. Kim, C.H. Lee, and D.D. Kim Synthesis and evaluation of ketorolac ester prodrugs for transdermal delivery J. Pharm. Sci. 92 2003 1008 1017 (Pubitemid 36523446)
16. B.B. Lundberg, V. Risovic, M. Ramaswamy, and K.M. Wasan A lipophilic paclitaxel derivative incorporated in a lipid emulsion for parenteral administration J. Control. Release 86 2003 93 100 (Pubitemid 35461976)
17. S. Majumdar, and K.B. Sloan Topical delivery of N-alkyl-N- alkyloxycarbonylaminomethyl (NANAOCAM) prodrugs of theophylline (ThH) Int. J. Pharm. 332 2007 64 71 (Pubitemid 46227765)
18. P. Suppasansatorn, G. Wang, B.R. Conway, W. Wang, and Y. Wang Skin delivery potency and antitumor activities of temozolomide ester prodrugs Cancer Lett. 244 2006 42 52 (Pubitemid 44485859)
19. H.K. Vaddi, M.O. Hamad, J. Chen, S.L. Banks, P.A. Crooks, and A.L. Stinchcomb Human skin permeation of branched-chain 3-O-alkyl ester and carbonate prodrugs of naltrexone Pharm. Res. 22 2005 758 765 (Pubitemid 40768588)
20. J.J. Wang, K.C. Sung, J.F. Huang, C.H. Yeh, and J.Y. Fang Ester prodrugs of morphine improve transdermal drug delivery: a mechanistic study J. Pharm. Pharmacol. 59 2007 917 925 (Pubitemid 47051071)
21. K.H. Bhandari, M. Newa, S.I. Yoon, J.S. Kim, K.Y. Jang, J.A. Kim, B.K. Yoo, J.S. Woo, J.H. Lee, D.D. Kim, H.G. Choi, and C.S. Yong Evaluation of physicochemical properties, skin permeation and accumulation profiles of ketorolac fatty ester prodrugs Biol. Pharm. Bull. 30 2007 2211 2216 (Pubitemid 350097064)
22. W.R. Lee, T.L. Pan, P.W. Wang, R.Z. Zhuo, C.M. Huang, and J.Y. Fang Erbium:YAG laser enhances transdermal peptide delivery and skin vaccination J. Control. Release 128 2008 200 208
23. K.B. Sloan, and S. Wasdo Designing for topical delivery: prodrugs can make the difference Med. Res. Rev. 23 2003 763 793 (Pubitemid 37306013)
24. L. Montenegro, C. Carbone, D. Paolino, R. Drago, A.H. Stancampiano, and G. Puglisi In vitro skin permeation of sunscreen agents from O/W emulsions Int. J. Cosmet. Sci. 30 2008 57 65
25. J. Rautio, T. Nevalainen, H. Taipale, J. Vepsälänen, J. Gynther, K. Laine, and T. Järvinen Piperazinylalkyl prodrugs of naproxen improve in vitro skin permeation Eur. J. Pharm. Sci. 11 2000 157 163 (Pubitemid 30479857)
26. B.Y. Kim, H.J. Doh, T.N. Le, W.J. Cho, C.S. Yong, H.G. Choi, J.S. Kim, C.H. Lee, and D.D. Kim Ketorolac amide prodrugs for transdermal delivery: stability and in vitro rat skin permeation studies Int. J. Pharm. 293 2005 193 202 (Pubitemid 40381092)
27. M. Gerber, J.C. Breytenbach, J. Hadgraft, and J. du Plessis Synthesis and transdermal properties of acetylsalicylic acid and selected esters Int. J. Pharm. 310 2006 31 36 (Pubitemid 43287964)
28. R.P. Waranis, and K.B. Sloan Effects of vehicles and prodrug properties and their interactions on the delivery of 6-mercaptopurine through skin: bisacyloxymethyl-6-mercaptopurine prodrugs J. Pharm. Sci. 76 1987 587 595 (Pubitemid 18026652)
29. J.F. Huang, K.C. Sung, O.Y.P. Hu, J.J. Wang, Y.H. Lin, and J.Y. Fang The effects of electrically-assisted methods on transdermal delivery of nalbuphine benzoate and sebacoyl dinalbuphine ester from solutions and hydrogels Int. J. Pharm. 297 2005 162 171 (Pubitemid 40720276)
30. M. Schäfer-Korting, W. Mehnert, and H.C. Korting Lipid nanoparticles for improved topical application of drugs for skin diseases Adv. Drug Deliv. Rev. 59 2007 427 443 (Pubitemid 47259224)
31. J. Juntunen, S. Majumdar, and K.B. Sloan The effect of water solubility of solutes on their flux through human skin in vitro: a prodrug database integrated into the extended Flynn database Int. J. Pharm. 351 2008 92 103 (Pubitemid 351186850)
32. D.C. Hammell, E.I. Stolarczyk, M. Klausner, M.O. Hamad, P.A. Crooks, and A.L. Stinchcomb Bioconversion of naltrexone and its 3-O-alkyl-ester prodrugs in a human skin equivalent J. Pharm. Sci. 94 2005 828 836 (Pubitemid 40577315)
33. B. Pavan, A. Dalpiaz, N. Ciliberti, C. Biondi, S. Manfredini, and S. Vertuani Progress in drug delivery to the central nervous system by the prodrug approach Molecules 13 2008 1035 1065
34. B. Abarca, R. Ballesteros, P. Bielsa, J. Moragues, P. D'Ocon, E. García-Zaragozá, and M.A. Noguera Opposite vascular activity of (R)-apomorphine and its oxidised derivatives. Endothelium-dependent vasoconstriction induced by the auto-oxidation metabolite Eur. J. Med. Chem. 38 2003 501 511 (Pubitemid 36588916)
35. G.L. Li, M. Danhof, and J.A. Bouwstra Iontophoretic delivery of apomorphine in vitro: physicochemic considerations Pharm. Res. 18 2001 1509 1513 (Pubitemid 33022404)
36. A.P. Morris, K.R. Brain, and C.M. Heard Skin permeation and ex vivo skin metabolism of O-acyl haloperidol ester prodrugs Int. J. Pharm. 367 2009 44 50
37. A.L. Stinchcomb, P.W. Swaan, O. Ekabo, K.K. Harris, J. Browe, D.C. Hammell, T.A. Cooperman, and M. Pearsall Straight-chain naltrexone ester prodrugs: diffusion and concurrent esterase biotransformation in human skin J. Pharm. Sci. 91 2002 2571 2578 (Pubitemid 35379414)
38. J.Y. Fang, Y.L. Leu, C.C. Chang, C.H. Lin, and Y.H. Tsai Lipid nano/submicron emulsions as vehicles for topical flurbiprofen delivery Drug Deliv. 11 2004 97 105
39. N.G. Eskandar, S. Simovic, and C.A. Prestidge Nanoparticle coated submicron emulsions: sustained in-vitro release and improved dermal delivery of all-trans-retinol Pharm. Res. 26 2009 1764 1775
40. J. Štecová, W. Mehnert, T. Blaschke, B. Kleuser, R. Sivaramakrishnan, C.C. Zouboulis, H. Seltmann, H.C. Korting, K.D. Kramer, and M. Schäfer-Korting Cyproterone acetate loading to lipid nanoparticles for topical acne treatment: particle characterization and skin uptake Pharm. Res. 24 2007 991 1000 (Pubitemid 46675401)
41. M.L. Forrest, J.A. Yáñez, C.M. Remsberg, Y. Ohgami, G.S. Kwon, and N.M. Davies Paclitaxel prodrugs with sustained release and high solubility in poly(ethylene glycol)-b-poly(-caprolactone) micelle nanocarriers: pharmacokinetic disposition, tolerability, and cytotoxicity Pharm. Res. 25 2008 194 206
42. R. Van der Geest, T. Van Laar, J.M. Gubbens-Stibbe, H.E. Boddé, and M. Danhof Iontophoretic delivery of R-apomorphine II: an in vivo study in patients with Parkinson's disease Pharm. Res. 14 1997 1803 1809