Novel N-3 substituted TSAO-T derivatives: Synthesis and anti-HIV-evaluation

Nucleosides, Nucleotides and Nucleic Acids

Volumn 27, Issue 4, 2008, Pages 351-367

  Bonache, María Cruz ^a   Quesada, Ernesto ^a   Sheen, Chih Wei ^b   Balzarini, Jan ^c   Sluis Cremer, Nicolas ^b   Pérez Pérez, María Jesús ^a   Camarasa, María José ^a   San Félix, Ana ^a  

^a INSTITUTO DE QUÍMICA MÉDICA   (Spain)

^b UNIVERSITY OF PITTSBURGH SCHOOL OF MEDICINE   (United States)

^c REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

Author keywords

AIDS; HIV 1 reverse transcriptase; TSAO T

Indexed keywords

2',5' BIS O (TERT BUTYLDIMETHYLSILYL) 3' SPIRO 5'' (4'' AMINO 1'',2'' OXATHIOLE 2'',2'' DIOXIDE)PYRIMIDINE; [1 [2',5' BIS O (TERT BUTYLDIMETHYLSILYL) BETA DEXTRO RIBOFURANOSYL] 3 N [2 ETHOXYCARBONYLVINYL]THYMINE] 3' SPIRO 5'' (4'' AMINO 1'',2'' OXATHIOLE 2'',2'' DIOXIDE); [1 [2',5' BIS O (TERT BUTYLDIMETHYLSILYL) BETA DEXTRO RIBOFURANOSYL] 3 N [2,3 EPOXYPROPYL]THYMINE] 3' SPIRO 5'' (4'' AMINO 1'';,2'' OXATHIOLE 2',2'' DIOXIDE); [1 [2',5' BIS O (TERT BUTYLDIMETHYLSILYL) BETA DEXTRO RIBOFURANOSYL] 3 N [3 HYDROXY 1 PROPENYL]THYMINE] 3' SPIRO 5'' (4'' AMINO 1'',2'' OXATHIOLE 2'',2'' DIOXIDE); [1 [2',5' BIS O (TERT BUTYLDIMETHYLSILYL) BETA DEXTRO RIBOFURANOSYL] 3 N [3 N (4 AZIDOSALICYLYL)AMINOPROPYL]THYMINE] 3' SPIRO 5'' (4'' AMINO 1'',2'' OXATHIOLE 2'',2'' DIOXIDE); [1 [2',5' BIS O (TERT BUTYLDIMETHYLSILYL) BETA DEXTRO RIBOFURANOSYL] 3 N [3 N [(4 (BENZOYL)CARBONYLPHENYL]AMINOPROPYL]THYMINE] 3' SPIRO 5'' (4'' AMINO 1'',2'' OXATHIOLE 2'',2'' DIOXIDE); [1 [2',5' BIS O (TERT BUTYLDIMETHYLSILYL) BETA DEXTRO RIBOFURANOSYL] 3 N [[N,N BIS(2 CHLOROETHYL)CARBAMOYL]METHYL]THYMINE] 3' SPIRO 5'' (4'' AMINO 1'',2'' OXATHIOLE 2'',2'' DIOXIDE); [2 [2',5' BIS O (TERT BUTYLDIMETHYLSILYL) BETA DEXTRO RIBOFURANOSYL] 3 N [2 ETHOXYCARBONYLVINYL]THYMINE] 3' SPIRO 5'' (4'' AMINO 1'',2'' OXATHIOLE 2'',2'' DIOXIDE); ALCOHOL; ALKYLATING AGENT; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; PYRIMIDINE DERIVATIVE; RNA DIRECTED DNA POLYMERASE; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; CIS ISOMER; CONTROLLED STUDY; COVALENT BOND; DRUG CONFORMATION; DRUG SCREENING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; NONHUMAN; PHOTOAFFINITY LABELING; STRUCTURE ACTIVITY RELATION; TRANS ISOMER;

AZIDES; BENZOPHENONES; CELL LINE; DRUG DESIGN; HIV; HIV REVERSE TRANSCRIPTASE; HIV-1; HIV-2; PROTEIN BINDING; REVERSE TRANSCRIPTASE INHIBITORS; SPIRO COMPOUNDS; SUBSTRATE SPECIFICITY; THYMIDINE; ULTRAVIOLET RAYS; VIRUS REPLICATION;

HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 42049097738     PISSN: 15257770     EISSN: 15322335     Source Type: Journal    
DOI: 10.1080/15257770801943990     Document Type: Article

References (36)

1. De Clercq, E. Trends in the development of new antiviral agents for the chemotherapy of infections caused by herpes viruses and retroviruses. Rev. Med. Virol. 1995, 5, 149-164.
2. De Clercq, E. Antiviral therapy for human inmunodeficiency virus infections. Clin. Microbiol. Rev. 1995, 8, 200-239.
3. Jacobo-Molina, A.; Arnold, E. HIV reverse transcriptase structure-function relationships. Biochemistry 1991, 30, 6351-6356.
4. Basu, A.; Basu, S.; Modak, M.J. Structure-activity analyses of HIV-1 reverse transcriptase. Biochem. Biophys. Res. Commun. 1992, 183, 1131-1138.
5. Katz, R.A.; Skalka, A.M. The retroviral enzymes. Annu. Rev. Biochem. 1994, 63, 133-173.
6. Vaishnav, Y.N.; Wong-Staal, F. The biochemistry of AIDS. Annu. Rev. Biochem. 1991, 60, 577-630.
7. Müller, B.; Restle, T.; Wiss, S.; Gautel, M.; Sczakie, G.; Goody, R.S. Co-expresion of the subunits of the heterodimer of HIV-1 reverse transcriptase in Escherichia coli. J. Biol. Chem. 1989, 264, 13975-13978.
8. Restle, T.; Müller, B.; Goody, R.S. Dimerization of human immunodeficiency virus type 1 reverse transcriptase. A target for chemotherapeutic intervention. J. Biol. Chem. 1990, 265, 8986-8988.
9. Restle, T.; Müller, B.; Goody, R.S. RNase H activity of HIV reverse transcriptases is confined exclusively to the dimeric forms. FEBS Lett. 1992, 300, 97-100.
10. Balzarini, J.; Pérez-Pérez, M.J.; San-Félix, A.; Schols, D.; Perno, C.F.; Vandamme, A.M.; Camarasa, M.J.; DeClercq, 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 inmunodeficiency virus type 1 that are targeted at the viral reverse transcriptase. Proc. Natl. Acad. Sci. USA 1992, 89, 4392-4396.
11. 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.
12. 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. Current Topics in Medicinal Chemistry 2004, 945-963.
13. Pérez-Pérez, M.J.; San-Félix, A.; Balzarini, J.; De Clercq, E.; Camarasa, M.J. TSAO analogues. Stereospecific synthesis and anti-HIV-1 activity of 1-[2′-5′-bis-O-(tert- butyldimethylsilyl)-β-D-ribofuranosyl]-3′-spiro- 5″-(4″-amino-1″,2″-oxathiole-2″,2″-dioxide) pyrimidine and pyrimidine modified nucleosides. J. Med. Chem. 1992, 35, 2988-2995.
14. Balzarini, J.; Karlsson, A.; Vandamme, A.M.; Pérez-Pérez, M.J.; Zhang, H.; Vrang, L.; Öberg, B.; Bäckbro, K.; Unge, T.; San-Félix, A.; Velázquez, S.; Camarasa, M.J.; DeClercq, E. Human immunodeficiency virus type 1 (HIV-1) strains selected for resistance against the HIV-1-specific [2′,5′-bis-O-(tert- butyldimethylsilyl)-3′-spiro-5″-(4″-amino-1″, 2″-oxathiole-2″,2″-dioxide)]-β-D-pentofuranosyl (TSAO) nucleoside analogues retain sensitivity to HIV-1-specific non-nucleoside inhibitors. Proc. Natl. Acad. Sci. USA 1993, 90, 6952-6956.
15. Balzarini, J.; Velázquez, S.; San-Félix, A.; Karlsson, A.; Pérez-Pérez, M.J.; Camarasa, M.J.; DeClercq, E. Human immunodeficiency virus type 1-specific [2′,5′-bis-O-(tert- butyldimethylsilyl)-β-D-ribofuranosyl]-3′-spiro- 5″-(4″-amino-1″,2″-oxathiole-2″,2″-dioxide) purine analogues show a resistance spectrum that is different from that of the human immunodeficiency virus type-1-specific non-nucleoside analogues. Mol. Pharmacol. 1993, 43, 109-114.
16. Boyer, P.L.; Ding, J.; Arnold, E.; Hughes, S.H. Subunit specificity of mutations that confer resistance to nonnucleoside inhibitors in human immunodeficiency virus type 1 reverse transcriptase. Antimicrob. Agents Chemother. 1994, 38, 1909-1914.
17. Jonckheere, H.; Taymans, J.M.; Balzarini, J.; Velázquez, S.; Camarasa, M.J.; Desmyter, J.; De Clercq, E.; Anné, J. Resistance of HIV-1 reverse transcriptase against [2′,5′-bis-O-(tert- butyldimethylsilyl)-β-D-ribo-furanosyl]-3′-spiro- 5″-(4″-amino-1″,2″-oxathiole-2″,2″-dioxide)] (TSAO) derivatives is determined by the mutation Glu138→Lys on the p51 subunit. J. Biol. Chem. 1994, 269, 25255-25258.
18. Nanni, R.G.; Ding, J.; Jacobo-Molina, A.; Hughes, S.H.; Arnold, E. Review of HIV-1 reverse transcriptase three-dimensional structure: implications for drug design. Perspect. Drug Discov. 1993, 1, 129-150.
19. Smerdon, S.J.; Jäger, J.; Wang, J.; Kohlstaedt, L.A.; Chirino, A.J.; Friedman, J.M.; Rice, P.A.; Steitz, T.A. Structure of the binding site for non-nucleoside inhibitors of the reverse transcriptase of human immunodeficiency virus type 1. Proc. Natl. Acad. USA 1994, 91, 3911-3915.
20. Balzarini, J.; Karlsson, A.; Pérez-Pérez, M.J.; Vrang, L.; Walbers, J.; Zhang, H.; Öberg, B.; Vandamme, A.M.; Camarasa, M.J.; De Clercq, E. HIV-1 specific reverse transcriptase inhibitors show differential activity against HIV-1 mutant strains containing different amino acid substitutions in the reverse transcriptase. Virology 1993, 192, 246-253.
21. 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.
22. Sluis-Cremer, N.; Dmitrienko, G.I.; Balzarini, J.; Camarasa, M.J.; Parniak, M.A. Human immunodeficiency virus type 1 reverse transcriptase dimer destabilization by 1-Spiro-[4″-amino-2,2″-dioxo-1″,2″- oxathiole-5″,3′-[2′,5′-bis-O-(tert- butyldimethylsilyl)-β-D-ribofuranosyl]]]-3-ethylthymine. Biochemistry 2000, 39, 1427-1433.
23. Bonache, M.C.; Chamorro, C.; Velázquez, S.; De Clercq, E.; Balzarini, J.; Rodriguez-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. Faja, M.; Ariza, X.; Gálvez, C.; Villarasa, J. Reaction of uridines and thymidines with methyl propionate. A new protecting group. Tetrahedron Lett. 1995, 36, 3216-264.
25. Huisgen, R.; Herbig, K.; Siegl, A.; Huber, H. Die addukte primäer und sekundäer amine an carbonester der acetylenreihe und ihre konfiguration. Chem. Ber. 1966, 99, 2526-2545.
26. Winterfeldt, E.; Preuss, H. Der sterische verlauf von additionen an die dreifachbindung. Chem. Ber. 1966, 99, 450-458.
27. Ninomiya, I.; Naito, T. in Equipment and techniques in photochemical synthesis. Photochemical synthesis. Academic Press: London, 1989, pp. 209-223.
28. Kopecky, J. in Photochemistry of alkenes. Organic Photochemistry: A visual approach. VCH Publishers, Inc.: New York, 1992, pp. 58-63.
29. Turro, N.J. in Organic photochemistry-an overview. Modern Molecular Photochemistry. The Benjamin/Cummings Publishing Co., Inc: Menlo Park, California, 1978, pp. 1-15.
30. Bergstrom, D.E.; Inoue, H.; Reddy, P.A. Pyrido[2,3-d]pyrimidine nucleosides. synthesis via cyclization of C-5 substituted cytidines. J. Org. Chem. 1982, 42, 2174-2178.
31. Dorman, G.; Prestwich, G.D. Benzophenone photophores in biochemistry. Biochemistry 1994, 33, 5661-5673.
32. Flemming, S.A. Chemical reagents in photoaffinity labelling. Tetrahedron 1995, 51, 12479-12520.
33. Kotzyba-Hilbert, F.; Kapfer, I.; Goeldner, M. Recent trends in photoaffinity labelling. Angew. Chem. Int. Ed. Engl. 1995, 34, 1296-1312.
34. Husain, S.N.; Gentile, B.; Sauers, R.R.; Eichholz, A. Synthesis of photoaffinity labeling derivatives of D-glucose and D-galactose. Carbohydr. Res. 1983, 118, 57-63.
35. Le Grice, S.F.J.; Gruninger-Leitch, F. Rapid purification of homodimer and heterodimer HIV-1 reverse transcriptase by metal chelate affinity chromatography. Eur J Biochem. 1990, 187, 307-314.
36. Le Grice, S.F.J.; Cameron, C.E.; Benkovic, S.J. Purification and characterization of human immunodeficiency virus type 1 reverse transcriptase. Methods Enzymol. 1995, 262, 130-144.