Dipeptide derivatives of AZT: Synthesis, chemical stability, activation in human plasma, hPEPT1 affinity, and antiviral activity

ChemMedChem

Volumn 3, Issue 6, 2008, Pages 970-978

  Santos, Cledir ^b   Morais, José ^a   Gouveia, Luís ^a   De Clercq, Erik ^c   Pannecouque, Christophe ^c   Nielsen, Carsten Uhd ^d   Steffansen, Bente ^d   Moreira, Rui ^a   Gomes, Paula ^b  

^a RESEARCH INSTITUTE FOR MEDICINES IMED ULISBOA   (Portugal)

^b UNIVERSITY OF PORTO   (Portugal)

^c REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

^d UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

Antiviral agents; AZT; Dipeptides; Drug delivery; HIV; Prodrugs

Indexed keywords

ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; COTRANSPORTER; DIPEPTIDE; PRODRUG; SLC15A1 PROTEIN, HUMAN; ZIDOVUDINE;

ARTICLE; CELL LINE; CELL STRAIN CACO 2; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; DRUG DESIGN; DRUG EFFECT; DRUG SCREENING; DRUG STABILITY; HUMAN; HUMAN IMMUNODEFICIENCY VIRUS 1; HUMAN IMMUNODEFICIENCY VIRUS 2; METABOLISM; MICROBIOLOGICAL EXAMINATION; STEREOISOMERISM; SYNTHESIS; TIME; TOXICITY TESTING;

ANTI-HIV AGENTS; CACO-2 CELLS; CELL LINE; DIPEPTIDES; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; DRUG EVALUATION, PRECLINICAL; DRUG STABILITY; HIV-1; HIV-2; HUMANS; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; PRODRUGS; STEREOISOMERISM; SYMPORTERS; TIME FACTORS; TOXICITY TESTS; ZIDOVUDINE;

EID: 48149103948     PISSN: 18607179     EISSN: 18607187     Source Type: Journal    
DOI: 10.1002/cmdc.200800012     Document Type: Article

References (45)

1. UNAIDS, AIDS Epidemic Update, December 2007: http://www.unaids. org/en/KnowledgeCentre/HIVData/EpiUpdate/EpiUpdArchive/2007/.
2. "Malaria and HIV interactions and their implications for public health policy": WHO, Report of a Technical Consultation, Geneva, Switzerland, 2005.
3. M. A. Fischl, D. D. Richman, M. H. Grieco, M. S. Gottlieb, P. A. Volberding, O. L. Laskin, J. M. Leedom, J. E. Groopman, D. Mildvan, R. T. Schooley, G. G. Jackson, D. T. Durack, D. King, N. Engl. J. Med. 1987, 317, 185-191.
4. E. De Clercq, J. Med. Chem. 1995, 38, 2491-2517.
5. K. von der Helm, Biol. Chem. 1996, 377, 765-774.
6. P. Mohan, Drug Des. Rev. 1993, 29, 1-17.
7. B. A. Styrt, T. D. Piazza-Hepp, G. K. Chikami, Antiviral Res. 1996, 31, 121-135.
8. R. W. Klecker, Jr., J. M. Collins, R. Yarchoan, R. Thomas, J. F. Jenkins, S. Broder, C. E. Meyers, Clin. Pharmacol. Ther. 1987, 41, 407-412.
9. S. Ellison, T. Terasaki, W. M. Pardridge, Clin. Res. 1988, 36, 117 A.
10. N. Bodor, H. H. Farag, M. E. Brewster, Science 1981, 214, 1370-1372.
11. N. Bodor, Drugs Future 1981, 6, 165.
12. T. Kawaguchi, K. Ishikawa, T. Seki, K. J. Juni, Pharm. Sci. 1990, 79, 531-533.
13. S. K. Aggarwal, S. R. Gogu, S. R. S. Rangan, K. C. Agrawal, J. Med. Chem. 1990, 33, 1505-1510.
14. C. Piantadosi, C. J. Marasco, S. L. Morris-Natschke, K. L. Meyer, F. Gumus, J. R. Surles, K. S. Ishaq, L. S. Kucera, N. Iyer, A. Wallen, S. Piantadosi, E. J. Modest, J. Med. Chem. 1991, 34, 1408-1414.
15. K. Y. Hostetler, PCT Int. Appl., WO 90/00555, January 25, 1990 [Chem. Abst. 113:78902s].
16. K. Y. Hostetler, L. M. Stuhmiller, H. B. Lenting, H. van den Bosch, D. D. Richman, J. Biol. Chem. 1990, 265, 6112-6117.
17. J. M. Steim, C. C. Neto, P. S. Sarin, D. K. Sun, R. K. Sehgal, J. G. Turcotte, Biochem. Biophys. Res. Commun. 1990, 171, 451-457.
18. P. F. Torrence, J. Kinjo, K. Lesiak, J. Balzarini, E. De Clercq, FEBS Lett. 1988, 234, 135-140.
19. C. K. Chu, V. S. Bhadti, K. J. Doshi, E. T. Etse, J. M. Gallo, F. D. Boudinot, R. F. Schinazi, J. Med. Chem. 1990, 33, 2188-2192.
20. E. Palomino, D. Kessel, J. P. Horwitz, J. Med. Chem. 1989, 32, 622-625.
21. C. McGuigan, K. G. Devine, T. J. O'Connor, A. Galpin, D. J. Jeffries, D. Kinchington, Antiviral Chem. Chemother. 1990, 1, 107-114.
22. C. McGuigan, S. R. Nicholls, T. J. O'Connor, D. Kinchington, Antiviral Chem. Chemother. 1990, 1, 25-33.
23. T. Yajima, K. Juni, M. Saneyoshi, T. Hasegawa, T. Kawaguchi, Biol. Pharm. Bull. 1998, 21, 272-277.
24. R. H. Lupia, N. Ferencz, J. L. Lertora, S. K. Aggarwal, W. J. George, K. C. Agrawal, Antimicrob. Agents Chemother. 1993, 37, 818-824.
25. B. M. Tadayoni, P. M. Friden, L. R. Walus, G. F. Musso, Bioconjugate Chem. 1993, 4, 139-145.
26. H.-K. Han, R. L. A. de Vrueh, J. K. Rhie, K.-M. Y. Covitz, P. L. Smith, C.-P. Lee, D.-M. Oh, W. Sadee, G. Amidon, Pharm. Res. 1998, 15, 1154-1159.
27. Y. E. Nashed, A. K. Mitra, Spectrochim. Acta Part A Mol. Biomol. Spectrosc. 2003, 59, 2033-2039.
28. B. S. Anand, J. M. Hill, S. Dey, K. Maruyama, P. S. Bhattacharjee, M. E. Myles, Y. E. Nashed, A. K. Mitra, Invest. Ophthalmol. Visual Sci. 2003, 44, 2529-2534.
29. S. Majumdar, Y. E. Nashed, K. Patel, R. Jain, M. Itahashi, D. M. Neumann, J. M. Hill, A. K. Mitra, J. Ocul. Pharmacol. Ther. 2005, 21, 463-474.
30. R. Jain, S. Agarwal, S. Majumdar, X. Zhu, D. Pal, A. K. Mitra, Int. J. Pharm. 2005, 303, 8-19.
31. R. Jain, S. Duvvuri, V. Kansara, N. S. Mandava, A. K. Mitra, Int. J. Pharm. 2007, 336, 233-240.
32. P. Lloyd-Williams, F. Albericio, E. Giralt, Chemical Approaches to the Synthesis of Peptides and Proteins; CRC, Boca Raton, 1997.
33. C. Santos, M. L. Mateus, A. P. dos Santos, R. Moreira, E. de Oliveira, P. Gomes, Bioorg. Med. Chem. Lett. 2005, 15, 1595-1598.
34. J. E. Purdie, N. L. Benoiton, J. Chem. Soc. Perkin Trans. 2 1973, 1845-1852.
35. E. Jensen, H. Bundgaard, Int. J. Pharm. 1991, 71, 117-125.
36. S. W. Larsen, M. Ankersen, C. Larsen, Eur. J. Pharm. Sci. 2004, 22, 399-400.
37. G. A. R. Y. Suaifan, M. F. Mahon, T. Arafat, M. D. Threadgill, Tetrahedron 2006, 62, 11245-11266.
38. S. Majumdar, S. Duvvuri, A. K. Mitra, Clin. Res. Reg. Affairs 2004, 21, 67-79.
39. C. Yang, H. Gao, A. K. Mitra, J. Pharm. Sci. 2001, 90, 617-623.
40. L. M. Beauchamp, G. F. Orr, P. de Miranda, T. Burnette, T. A. Krenitsky, Antiviral Chem. Chemother. 1992, 3, 157-164.
41. X. Song, B. S. Vig, P. L. Lorenzi, J. C. Drach, L. B. Townsend, G. L. Amidon, J. Med. Chem. 2005, 48, 1274-1277.
42. H. Abe, M. Satoh, S. Miyauchi, S. Shuto, A. Matsuda, N. Kamo, Bioconjugate Chem. 1999, 10, 24-31.
43. A. H. Eriksson, P. L. Elm, M. Begtrup, R. Nielsen, B. Steffansen, B. Brodin, Mol. Pharm. 2005, 2, 242-249.
44. C. U. Nielsen, R. Andersen, B. Brodin, S. Frokjaer, M. Taub, B. Steffansen, J. Controlled Release 2001, 76, 129-138.
45. R. Pauwels, J. Balzarini, M. Baba, R. Snoeck, D. Schols, P. Herdewijn, J. Desmyter, E. De Clercq, J. Virol. Methods 1988, 20, 309-321.