Synthesis, in Vitro Evaluation, and Antileishmanial Activity of Water-Soluble Prodrugs of Buparvaquone

Journal of Medicinal Chemistry

Volumn 47, Issue 1, 2004, Pages 188-195

  Mäntylä, Antti ^a   Garnier, Tracy ^b   Rautio, Jarkko ^a   Nevalainen, Tapio ^a   Vepsälainen, Jouko ^a   Koskinen, Ari ^c   Croft, Simon L ^b   Järvinen, Tomi ^a  

^a UNIVERSITY OF EASTERN FINLAND   (Finland)

^b LONDON SCHOOL OF HYGIENE AND TROPICAL MEDICINE   (United Kingdom)

^c AALTO UNIVERSITY   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

[3 (4 TERT BUTYLCYCLOHEXYLMETHYL) 1,4 DIOXO 1,4 DIHYDRONAPHTHALEN 2 YL]PHOSPHATE; [3 (4 TERT BUTYLCYCLOHEXYLMETHYL) 1,4 DIOXO 1,4 DIHYDRONAPHTHALEN 2 YLOXYMETHYL]PHOSPHATE; ALKALINE PHOSPHATASE; ANTILEISHMANIAL AGENT; BUPARVAQUONE; NAPHTHOQUINONE; PRODRUG; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIPROTOZOAL ACTIVITY; AQUEOUS SOLUTION; ARTICLE; CONTROLLED STUDY; DRUG BIOAVAILABILITY; DRUG DELIVERY SYSTEM; DRUG DISTRIBUTION; DRUG PENETRATION; DRUG SYNTHESIS; EVALUATION; HUMAN; HUMAN TISSUE; LEISHMANIA; LEISHMANIA DONOVANI; LEISHMANIA MEXICANA; LEISHMANIA PANAMENSIS; LIPID SOLUBILITY; MOUSE; NONHUMAN; PH MEASUREMENT; SKIN LEISHMANIASIS; SKIN PERMEABILITY; VISCERAL LEISHMANIASIS;

ADMINISTRATION, ORAL; ADMINISTRATION, TOPICAL; ALKALINE PHOSPHATASE; ANIMALS; ANTIPROTOZOAL AGENTS; CRICETINAE; FEMALE; HUMANS; HYDROLYSIS; LEISHMANIA; LEISHMANIASIS, CUTANEOUS; LEISHMANIASIS, VISCERAL; MACROPHAGES, PERITONEAL; MICE; NAPHTHOQUINONES; PERMEABILITY; PHOSPHORIC ACID ESTERS; PRODRUGS; SKIN; SOLUBILITY; WATER;

EID: 0347361636     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm030868a     Document Type: Article

References (38)

1. World Health Organization, Division of Control of Tropical Diseases, http://www.who.int/emc/diseases/leish/index.html.
2. Desjeux, P. Leishmaniasis. Public Health Aspects and Control. Clin Dermatol. 1996, 14, 417-423.
3. Berman, J. D. Human Leishmaniasis: Clinical, Diagnostic, and Chemotherapeutic Developments in the Last 10 Years. Clin. Infect. Dis. 1997, 24, 684-703.
4. Croft, S. L.; Yardley, V. Chemotherapy of Leishmaniasis. Curr. Pharm. Des. 2002, 8, 319-341.
5. Hudson, A. T.; Randall, A. W.; Fry, M.; Ginger, C. D.; Hill, B.; Latter, V. S.; McHardy, N.; Williams, R. B. Novel Anti-Malarial Hydroxynaphthaquinones with Potent Broad Spectrum Antiprotozoal Activity. Parasitology 1985, 90, 45-55.
6. Hudson, A. T.; Pether, M. J.; Randall, A. W. In Vitro Activity of 2-cycloalkyl-3-hydroxy-1,4-naphthoquinones against Theileria, Eimeria and Plasmodia Species. Eur. J. Med. Chem. 1986, 21, 271-275.
7. Croft, S. L.; Evans, A. T.; Neal, R. A. The Activity of Plumbagin and Other Electron Carriers Against Leishmania donovani and Leishmania mexicana amazonensis. Ann. Trop. Med. Parasitol. 1985, 79, 651-653.
8. Croft, S. L.; Hogg, J.; Gutteridge, W. E.; Hudson, A. T.; Randall, A. W. The Activity of Hydroxynaphthoquinones against Leishmania donovani. J. Antimicrob. Chem. 1992, 30, 827-832.
9. Bundgaard, H. Design of Prodrugs; Bundgaard, H., Ed.; Elservier: Amsterdam, 1985; pp 1-92.
10. Stella, V. J.; Charman, W. N. A.; Naringrekar, V. H. Prodrugs. Do They Have Advantages in Clinical Practice. Drugs 1985, 29, 455-473
11. Fleisher, D.; Bong, R.; Stewart, B. H. Improved Oral Drug Delivery: Solubility Limitations Overcome by the Use of Prodrugs. Adv. Drug Delivery Rev. 1996, 19, 115-130.
12. Leppänen, J.; Huuskonen, J.; Savolainen, J.; Nevalainen, T.; Taipale, H.; Vepsäläinen, J.; Gynther, J.; Järvinen, T. Synthesis of a Water-Soluble Prodrug of Entacapone. Bioorg. Med. Chem. Lett. 2000, 10, 1967-1969.
13. Golik, J.; Wong, H. S. L.; Chen, S. H. C.; Doyle, T. W.; Wright, J. J. K.; Knipe, J.; Rose, W. C.; Casazza, A. M.; Vyas, D. M. Synthesis and Antitumor Evaluation of Paclitaxel Phosphonaoxymethyl Ethers: A Novel Class of Water Soluble Paclitaxel Pro-drugs. Bioorg. Med. Chem. Lett. 1996, 6, 1837-1842.
14. Varia, S. A.; Schuller, S.; Sloan, K. B.; Stella, V. J. Phenytoin prodrugs III: Water-soluble Prodrugs for Oral and/or Parenteral Use. J. Pharm. Sci. 1984, 73, 1068-1073.
15. Sloan, K. B. Functional Group Considerations in the Development of Prodrugs Approaches to Solving Topical Delivery Problems. In Prodrugs, Topical and Ocular Drug Delivery; Sloan, K. B., Ed., Marcel Dekker Inc.: New York, 1992; pp 1-116.
16. Krise, J. P.; Zygmunt, J.; Georg, G. I.; Stella, V. J. Novel Prodrug Approach for Tertiary Amines: Synthesis and Preliminary Evaluation of N-Phosphonooxymethyl Prodrugs. J. Med. Chem. 1999, 42, 3094-3100.
17. Rautio, J.; Nevalainen, T.; Taipale, H.; Vepsäläinen, J.; Gynther, J.; Pedersen, T.; Järvinen, T. Synthesis and In vitro Evaluation of Aminoacyloxyalkyl Esters of 2-(6-methoxy-2-naphthyl)propionic Acid as Novel Naproxen Prodrugs for Dermal Drug Delivery. Pharm Res. 1999, 16, 1172-1178.
18. Rautio, J.; Nevalainen, T.; Taipale, H.; Vepsäläinen, J.; Gynther, J.; Laine, K.; Järvinen, T. Synthesis and In vitro Evaluation of Novel Morpholinyl- and Methylpiperazinylacylalkyl Prodrugs of 2-(6-methoxy-2-naphthyl)propionic Acid (Naproxen) for Topical Drug Delivery. J. Med. Chem. 2000, 43, 1489-1494.
19. Hadgraft, J. Skin, the Final Frontier. Int. J. Pharm. 2001, 224, 1-18.
20. Slotin, L. A. Current Methods of Phosphorylation of Biological Molecules. Synthesis 1976, 737-752.
21. Alewood, P. F.; Johns, R. B.; Valerio, R. M. A Simple Preparation of O-phospho-L-tyrosine. Synthesis 1983, 1, 30-31.
22. Hopper, D. W.; Catalano, J. G.; Macdonald, T. L. Facile Synthesis of Lysophospholipids Containing Unsaturated Fatty Acid Chains. Tetrahedron Lett. 1996, 37, 7871-7874.
23. Mäntylä, A.; Vepsälainen, J.; Järvinen, T.; Nevalainen, T. A Novel Synthetic Route for the Preparation of Alkyl and Benzyl Chloromethyl Phosphates. Tetrahedron Lett. 2002, 43, 3793-3794.
24. Medina, J. C.; Salomon, M.; Kyler, K. S. A Mild Method for the Conversion of Alcohols to Methylthiomethyl Ethers. Tetrahedron Lett. 1988, 29, 3773-3776.
25. Vyas, D. M.; Wong, H. S. L.; Crosswell, A. R.; Casazza, A. M.; Knipe, J. ; Mamber, S. W.; Doyle, T. Synthesis and Antitumor Evaluation of Water Soluble Taxol Phosphates. Bioorg. Med. Chem. Lett. 1993, 3, 1357-1360.
26. Friis, G. J.; Bundgaard, H. Design and Application of Prodrugs. In A Textbook of Drug Design and Development, 2nd ed.; Krogsgaard-Larsen, P., Liljefors, T., Madsen, U., Eds.; Harwood Academic Publishers GmbH: Amsterdam, 1996; pp 351-385.
27. Abul-Fadl, M. A. M.; Kin, E. J. Properties of the Acid Phosphatases of Erythrocytes and of the Human Prostate Gland. Biochem. J. 1949, 45, 51-60.
28. Moss, D. W. Alkaline Phosphatase Isoenzymes. Clin. Chem. 1982, 28, 2007-2016.
29. TenHoor, C. N.; Stewart, B. H. Reconversion of Fosphenytoin in the Presence of Intestinal Alkaline Phosphatase. Pharm. Res. 1995, 12, 1806-1809.
30. Mikus, J.; Steverdin, D. A Simple Colometric Method to Screen Drug Cytotoxicity against Leishmania Using the Dye Alamar Blue. Parasitol. Int. 2000, 48, 265-269.
31. a Determination of Water-insoluble Drugs in Organic Solvent-water Mixtures. J. Pharm. Biomed. Anal. 1999, 20, 631-641.
32. a Determination of Water-insoluble Compounds: Validation Study in Methanol/water Mixtures. Int. J. Pharm. 1997, 151, 235-248.
33. Avdeef, A. Assessment of Distribution-pH Profiles. In Lipophilicity in Drug Action and Toxicology; Pliska, V., Testa, B., van de Waterbeemd, H., Eds.; VCH: Weinheim, 1996; 109-139.
34. Lambert, W. J. Modelling Oil-Water Partitioning and Membrane Permeation Using Reversed-Phase Chromatography. J. Chromatogr. A 1993, 656, 469-484.
35. Niemi, R.; Vepsäläinen, J.; Taipale, H.; Järvinen, T. Bisphosphonate Prodrugs: Synthesis and in Vitro Evaluation of Novel Acyloxyalkyl Esters of Clodronate Acid. J. Med. Chem. 1999, 42, 5053-5058.
36. Neumann, M. G.; Schmitt, C. C.; Previtali, C. M.; Bertolotti, S. G. Photoreduction of Resazurin in the Presence of Aliphatic Amines. Dyes Pigments 1996, 32, 93-99.
37. Maser, P.; Grether-Buhler, Y.; Kaminsky, R.; Brun, R. An Anti-Contamination Cocktail for the In vitro Isolation and Cultivation of Parasitic Protozoa. Parasit. Res. 2002, 88, 172-174.
38. Neal, R. A.; Croft, S. L. An In-Vitro System for Determining the Activity of Compounds against the Intracellular Amastigote Form of Leishmania Donovani. J. Antimicrob. Chemother. 1984, 14, 463-475.