Design and discovery of a novel dipeptidyl-peptidase IV (CD26)-based prodrug approach

Journal of Medicinal Chemistry

Volumn 49, Issue 17, 2006, Pages 5339-5351

  García Aparicio, Carlos ^a   Bonache, María Cruz ^a   De Meester, Ingrid ^c   San Félix, Ana ^a   Balzarini, Jan ^b   Camarasa, María José ^a   Velázquez, Sonsoles ^a  

^a INSTITUTO DE QUÍMICA MÉDICA   (Spain)

^b REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

^c UNIVERSITY OF ANTWERP   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

ALANINE; AMIDE; AMINO ACID; DIPEPTIDE; DIPEPTIDYL PEPTIDASE IV; PRODRUG; PROLINE;

AMINO TERMINAL SEQUENCE; ANTIVIRAL ACTIVITY; ARTICLE; CELL SURFACE; CHEMICAL BOND; CONJUGATE; CYTOSTASIS; DRUG CYTOTOXICITY; DRUG DESIGN; DRUG HALF LIFE; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME SUBSTRATE COMPLEX; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; IC 50; IN VITRO STUDY; LIPOPHILICITY; NONHUMAN; PLASMA; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; VIRUS REPLICATION;

ANIMALS; ANTI-HIV AGENTS; ANTIGENS, CD26; CATALYSIS; CATTLE; DRUG DESIGN; ENZYME ACTIVATION; HIV-1; HUMANS; MICROBIAL SENSITIVITY TESTS; MOLECULAR CONFORMATION; OLIGOPEPTIDES; PRODRUGS; REVERSE TRANSCRIPTASE INHIBITORS; SPIRO COMPOUNDS; STRUCTURE-ACTIVITY RELATIONSHIP; THYMIDINE; TIME FACTORS; VIRUS REPLICATION;

EID: 33747485595     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0606490     Document Type: Article

References (41)

1. Fox, D. A.; Hussey, R. E.; Fitzgerald, K. A.; Acuto, O.; Poole, C.; Palley, L. et al. Tal, a novel 105 kDa human T cell activation antigen defined by a monoclonal antibody. J. Immunol. 1984, 132, 1250-1256.
2. De Meester, I.; Vanhoof, G.; Lambeir, A.-M.; Scharpe, S. CD26, let it cut or cut it down. Immunol. Today 1999, 20, 367-375.
3. Lambeir, A.-M.; Durinx, C.; Scharpe, S.; De Meester, I. Dipeptidyl-peptidase IV from bench to bedside: An update on structural properties, functions and clinical aspects of the enzyme DPPIV. Crit. Rev. Clin. Lab. Sci. 2003, 40, 209-294.
4. Yaron, A.; Naider, F. Proline-dependent structural and biological properties of peptides and proteins. Crit. Rev. Biochem. Mol. 1993, 28, 31-81.
5. 2). Int. J. Biochem. Cell B. 2004, 36, 1848-1859.
6. Wermuth, C. G. Designing prodrugs and bioprecursors. The practice of medicinal chemistry, 2nd ed.; Wermuth, C. G., Ed.; Academic Press: London, 2003; pp 561-582.
7. (a) Silverman, R. B. The organic chemistry of drug design and drug action; Academia Press: San Diego, 2004; pp 497-549.
8. (b) Testa, B. Prodrug research: futile or fertile. Biochem. Pharmacol. 2004, 68, 2097-2106.
9. (a) Colla, L.; De Clercq, E.; Busson, R.; Vanderhaeghe, H. Synthesis and antiviral activity of water-soluble esters of acyclovir [9-[(2-hydroxyethoxy) methyl]guanine]. J. Med. Chem. 1983, 26, 602-604.
10. (b) Beauchamp, L. M.; Orr, G. F.; De Miranda, P.; Burnette, T.; Krenitsky, T. A. Amino acid ester prodrugs of acyclovir. Antiviral Chem. Chemother. 1992, 3, 157-164.
11. (a) Beutner, K. R. Valacyclovir: a review of its antiviral activity, pharmacokinetic properties, and clinical efficacy. Antivir. Res. 1995, 28, 281-290.
12. (b) MacDougall, C.; Guglielmo, B. J. Pharmacokinetics of valacyclovir. J. Antimicrob. Chemother. 2004, 53, 899-901.
13. Cocohoba, J. M.; McNicholl, I. R. Valganciclovir: an advance in cytomegalovirus therapeutics. Ann. Pharmacother. 2002, 6, 1075-1079.
14. a) Ganapathy, M. E.; Huang, W.; Ganapathy, V.; Leibach, F. H. Valacyclovir: a substrate for the intestinal and renal peptide transporters PEPT1 and PEPT2. Biochem. Biophys. Res. Commun. 1998, 240, 470-475.
15. (b) Han, H.; de Vrueh, R. L. A.; Rhie, J. K.; Covitz, K. Y.; Smith, P. L.; Lee, C.; Oh, D.; Sadée, W.; Amidon, G. L. 5′-Amino acid esters of antiviral nucleosides, acyclovir, and AZT are absorbed by the intestinal PEPT1 peptide transporter. Pharmacol. Res. 1998, 15 (8), 1154-1159.
16. Vanhoof, G.; Goossens, F.; De Meester, I.; Hendriks, D.; Scharpé, S. Proline motifs in peptides and their biological processing. FASEB J. 1995, 9, 736-744.
17. (a) Balzarini, J.; Pérez-Pérez, M.-J.; San-Félix, A.; Schols, D.; Perno, C. F.; Vandamme, A.-M.; Camarasa, M.-J.; De Clercq, E. 2′,5′-Bis-O-(tert-butyldimethylsilyl)-3′-spiro-5″- (4″-amino-1″,2″-oxathiole-2″,2″-dioxide) pyrimidine (TSAO) nucleoside analogues: Highly selective inhibitors of human immunodeficiency virus type 1 that are targeted at the viral reverse transcriptase. Proc. Natl. Acad. Sci. USA 1992, 89, 4392-4396.
18. (b) Camarasa, M.-J.; Pérez-Pérez, M.-J.; San-Félix, A.; Balzarini, J.; De Clercq, E. 3′-Spironucleosides (TSAO derivatives), a new class of specific human immunodeficiency virus type 1 inhibitors: Synthesis and antiviral activity of 3′-spiro-5″-[4″-amino-1″, 2″-oxathiole-2″,2″-dioxide]pyrimidine nucleosides. J. Med. Chem. 1992, 35, 2721-2727.
19. (a) Balzarini, J.; Naesens. L.; Bohman, C.; Pérez-Pérez, M.-J.; San-Félix, A.; Camarasa, M.-J.; De Clercq, E. Metabolism and pharmacokinetics of the anti-HIV-1-specific inhibitor [1-[2′,5′-bis- O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]3-N-methyl-thymine] -3′-spiro-5″-(4″-amino-1″,2″-oxathiole-2″, 2″-dioxide). Biochem. Pharmacol. 1993, 46, 69-77.
20. (b) Camarasa, M.-J.; San-Félix, A.; Pérez-Pérez, M.-J.; Velázquez, S.; Alvarez, R.; Chamorro, C.; Jimeno, M. L.; Pérez, C.; Gago, F.; De Clercq, E.; Balzarini, J. HIV-1 specific reverse transcriptase inhibitors: why are TSAO-nucleosides so unique? J. Carbohydr. Chem. 2000, 19, 451-469.
21. Camarasa, M.-J.; San-Félix, A.; Velázquez, S.; Pérez-Pérez, M.-J.; Gago, F.; Balzarini, J. TSAO compounds: The comprehensive story of a unique family of HIV-1 specific inhibitors of Reverse Transcriptase. Curr. Top. Med. Chem. 2004, 4, 945-963.
22. De Castro, S.; Lobatón, E.; Pérez-Pérez, M.-J.; San-Félix, A.; Cordeiro, A.; Andrei, G.; Snoeck, R.; De Clercq, E.; Balzarini, J.; Camarasa, M.-J.; Velázquez, S. Novel [2′,5′- Bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]-3′-spiro-5″- (4″-amino-1″,2″-oxathiole-2″,2″-dioxide) derivatives with anti-HIV-1 and anti-Human-Cytomegalovirus activity. J. Med. Chem. 2005, 48, 1158-1168.
23. Bonache, M. C.; Chamorro, C.; Velázquez, S.; De Clercq, E.; Balzarini, J.; Rodríguez Barrios, F.; Gago, F.; Camarasa, M.-J.; San-Félix, A. Improving the antiviral efficacy and selectivity of HIV-1 Reverse Transcriptase inhibitor TSAO-T by the introduction of functional groups at the N-3 position. J. Med. Chem. 2005, 48, 6653-6660.
24. Rodríguez-Barrios, F.; Pérez, C.; Lobatón, E.; Velázquez, S.; Chamorro, C.; San-Félix, A.; Pérez- Pérez, M.-J.; Camarasa, M.-J.; Pelemans, H.; Balzarini, J.; Gago, F. Identification of a putative binding site for [2′,5′-Bis-O-(tert- butyldimethylsilyl)-β-D-ribofuranosyl]-3′-spiro-5″-(4″- amino-1″,2″-oxathiole-2′,2″-dioxide)thymine (TSAO) derivatives at the p51-p66 interface of HIV-1 reverse transcriptase. J. Med. Chem. 2001, 44, 1853-1865.
25. Hartrodt, B.; Neubert, K.; Fischer, G.; Schulz, H.; Barth, A. Synthesis and enzymatic degradation of β-casomorphine-5. Pharmazie 1982, 37, 165-169.
26. Nakata, T.; Nakatani, M.; Takahashi, M.; Okai, J.; Kawaoka, Y. et al. Peptide synthesis in aqueous solution. V. Properties and reactivates of (p-hydroxyphenyl)benzylmethylsulfonium salts for direct benzyl esterification of N-acylpeptides. Bull. Chem. Soc. Jpn. 1996, 69, 1099-1106.
27. Luthman, K.; Hacksell, U. Conformational analysis of benzyloxy- carbonylglycyl-1-proline. Acta Chem. Scand. 1993, 47, 461-468.
28. 4. Liebigs. Ann. Chem. 1992, 4, 361-370.
29. Kanaoka, Y.; Takaashi, T.; Nakayama, H.; Tanizawa, K. New fluorogenic substrates for subtilisin. Chem. Pharm. Bull. 1985, 33, 1721-1724.
30. (a) Goli, D. M.; Chessman, B. V.; Hassan, M. E.; Lodaya, R.; Slama, J. T. Synthesis of (2R, 3R, 4S)-2-hydroxymethylpyrrolidine-3,4-diol from (2S)-3,4-dehydroproline derivatives. Carbohydr. Res. 1994, 259, 219-241.
31. (b) Schumacher, K. K.; Jiang, J.; Joullié, M. M. Synthetic studies toward astins A, B and C. Efficient syntheses of cis-3,4-dihydroxyprolines and (-)-(3S, 4R)-dichloroproline esters. Tetrahedron-Asymmetry 1998, 9, 47-53.
32. Patiño-Molina, R.; Martín-Martínez, M.; Herranz, R.; García-López, M. T.; González-Muñiz, R. Studies on the synthesis of β-keto esters derived from dipeptides: search for a low-epimerizing method. Lett. Pept. Sci. 2000, 7, 143-149.
33. Umezawa, H.; Aoyagi, T.; Ogawa, K.; Hamada, M.; Takeuchi, T. Diprotins A and B, inhibitors of dipeptidyl aminopeptidase IV, produced by bacteria. J. Antibiot. 1984, 37, 422-425.
34. Schön, E.; Born, I.; Demuth, H. U.; Faust, J.; Neubert, K.; Steinmetzer, T.; Barth, A.; Ansorage, S. Dipeptidyl peptidase IV in the immune system. Effects of specific inhibitors on activity of dipeptidyl peptidase IV and proliferation of human lymphocytes. Biol. Chem. Hoppe Seyler 1991, 372, 305-311.
35. Augustyns, K.; Bal, G.; Thonus, G.; Belyaev, A.; Zhang, X. M.; Bollaert, W.; Lambeir, A. M.; Durinx, C.; Goosens, F.; Haemers, A. The unique properties of dipeptidyl-peptidase IV (DPP IV/CD26) and the therapeutic potential of DPP IV inhibitors. Curr. Med. Chem. 1999, 6, 311-328.
36. De Meester, I.; Lambeir, A.-M.; Proost, P.; Scharpé, S. Dipeptidyl peptidase IV substrate. An update on in vitro peptide hydrolysis by human DPPIV. In Dipeptidyl Aminopeptidases in Health and Disease; Hildebrandt, M.; Klapp, B. F.; Hoffman, T.; Demuth, H.-U., Eds.; Kluwer Academic/Plenum Publishers: New York, 2003; pp 3-17.
37. Sarges, R.; Witkop, B.; Gramicidin, A. VI. The synthesis of valine-and isoleucine-gramicidine A. J. Am. Chem. Soc. 1965, 87, 2020-2027.
38. Schmidt, U.; Utz, R.; Lieberknecht, A.; Griesser, H.; Potzolli, B.; Bahr, J.; Wagner, K.; Fischer, P. Amino acids and peptides; 60. Synthesis of biologically active cyclopeptides; 10. Synthesis of 16 structural isomers of dolastatin 3; II: Synthesis of the linear educts and the cyclopeptides. Synthesis-Stuttgart 1987, 236-241.
39. Ktritzky, A. R.; Suzuki, K.; Singh, S. K. Highly diastereoselective peptide chain extensions of unprotected amino acids with N-(Z-α-aminoacyl) benzotriazoles. Synthesis-Stuttgart 2004, 2645-2652.
40. De Meester, I.; Vanhoof, G.; Lambeir, A.-M.; Scharpé, S. Use of immobilized adenosine deaminase (EC 3.5.4.4) for the rapid purification of native human CD26/dipeptidyl peptidase IV (EC 3.4.14.5). J. Immunol. Methods 1996, 189, 99-105.
41. Christoffers, J.; Mann, A. New quiral auxiliaries for the construction of quaternary stereocenters by copper-catalyzed Michael reactions. Angew. Chem., Int. Ed. 2000, 39, 2752-2754.