Synthesis of paromomycin derivatives modified at C(5″) to selectively target bacterial rRNA

Carbohydrate Research

Volumn 342, Issue 3-4, 2007, Pages 499-519

  Kudyba, Iwona ^a   Fernandez, Déborah Perez ^a   Böttger, Erik C ^b   Vasella, Andrea ^a  

^a ETH ZURICH   (Switzerland)

^b UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

Aminoglycoside antibiotics; Carboxamide; Mycobacterium smegmatis; Oxidation; Oxime; Paromomycin; Selectivity

Indexed keywords

AMINOGLYCOSIDE ANTIBIOTICS; CARBOXAMIDE; MYCOBACTERIUM SMEGMATIS; OXIME; PAROMOMYCIN; SELECTIVITY;

ALDEHYDES; BACTERIA; CARBOXYLIC ACIDS; DERIVATIVES; OXIDATION; RNA; SYNTHESIS (CHEMICAL);

ANTIBIOTICS;

BENZYLIDENE DERIVATIVE; C 6' DEOXYPAROMOMYCIN; HYDROXIDE; PAROMOMYCIN; RIBOSOME RNA; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ARTICLE; DRUG DESIGN; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL;

MYCOBACTERIUM SMEGMATIS; OXIDATION-REDUCTION; PAROMOMYCIN; RIBOSOMES; RNA, BACTERIAL; RNA, RIBOSOMAL; STRUCTURE-ACTIVITY RELATIONSHIP;

BACTERIA (MICROORGANISMS); MYCOBACTERIUM SMEGMATIS;

EID: 33846540225     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2006.09.014     Document Type: Article

References (54)

1. Mingeot-Leclercq M.P., Glupczynski Y., and Tulkens P.M. Antimicrob. Agents Chemother. 43 (1999) 727-737
2. Kotra L.P., Haddad J., and Mobashery S. Antimicrob. Agents Chemother. 44 (2000) 3249-3256
3. Magnet S., and Blanchard J.S. Chem. Rev. 105 (2005) 477-497
4. Jana S., and Deb J.K. Appl. Microbiol. Biotechnol. 70 (2006) 140-150
5. Vicens Q., and Westhof E. Chembiochem 4 (2003) 1018-1023
6. Ogle J.M., Carter A.P., and Ramakrishnan V. Trends Biochem. Sci. 28 (2003) 259-266
7. Recht M.I., Douthwaite S., and Puglisi J.D. EMBO J. 18 (1999) 3133-3138
8. Böttger E.C., Springer B., Prammananan T., Kidan Y., and Sander P. EMBO Rep. 2 (2001) 318-323
9. Waguespack J.R., and Ricci A.J. J. Physiol.-London 567 (2005) 359-360
10. Mingeot-Leclercq M.P., and Tulkens P.M. Antimicrob. Agents Chemother. 43 (1999) 1003-1012
11. Hobbie S.N., Pfister P., Brüll C., Westhof E., and Böttger E.C. Antimicrob. Agents Chemother. 49 (2005) 5112-5118
12. Hobbie S.N., Pfister P., Brüll C., Sander P., Francois B., Westhof E., and Böttger E.C. Antimicrob. Agents Chemother. 50 (2006) 1489-1496
13. Recht M.I., Douthwaite S., Dahlquist K.D., and Puglisi J.D. J. Mol. Biol. 286 (1999) 33-43
14. Pfister P., Hobbie S., Vicens Q., Böttger E.C., and Westhof E. Chembiochem 4 (2003) 1078-1088
15. Pfister P., Hobbie S., Brüll C., Corti N., Vasella A., Westhof E., and Böttger E.C. J. Mol. Biol. 346 (2005) 467-475
16. Ryu D.H., and Rando R.R. Bioorg. Med. Chem. 9 (2001) 2601-2608
17. Destasio E.A., and Dahlberg A.E. J. Mol. Biol. 212 (1990) 127-133
18. Vourloumis D., Takahashi M., Winters G.C., Simonsen K.B., Ayida B.K., Barluenga S., Qamar S., Shandrick S., Zhao Q., and Hermann T. Bioorg. Med. Chem. Lett. 12 (2002) 3367-3372
19. Knowles D.J.C., Foloppe N., Matassova N.B., and Murchie A.I.H. Curr. Opin. Pharmacol. 2 (2002) 501-506
20. Haddad J., Kotra L.P., Llano-Sotelo B., Kim C., Azucena E.F., Liu M.Z., Vakulenko S.B., Chow C.S., and Mobashery S. J. Am. Chem. Soc. 124 (2002) 3229-3237
21. Foloppe N., Chen I.J., Davis B., Hold A., Morley D., and Howes R. Bioorg. Med. Chem. 12 (2004) 935-947
22. Barker J.J. Drug Discovery Today 11 (2006) 391-404
23. Sutcliffe J.A. Curr. Opin. Microbiol. 8 (2005) 534-542
24. Franceschi F., and Duffy E.M. Biochem. Pharmacol. 71 (2006) 1016-1025
25. Shandrick S., Zhao Q., Han Q., Ayida B.K., Takahashi M., Winters G.C., Simonsen K.B., Vourloumis D., and Hermann T. Angew. Chem., Int. Ed. 43 (2004) 3177-3182
26. Carter A.P., Clemons W.M., Brodersen D.E., Morgan-Warren R.J., Wimberly B.T., and Ramakrishnan V. Nature 407 (2000) 340-348
27. Vicens Q., and Westhof E. Structure 9 (2001) 647-658
28. Fourmy D., Recht M.I., Blanchard S.C., and Puglisi J.D. Science 274 (1996) 1367-1371
29. Fourmy D., Recht M.I., and Puglisi J.D. J. Mol. Biol. 277 (1998) 347-362
30. Recht M.I., Fourmy D., Blanchard S.C., Dahlquist K.D., and Puglisi J.D. J. Mol. Biol. 262 (1996) 421-436
31. Wang Y., Hamasaki K., and Rando R.R. Biochemistry 36 (1997) 768-779
32. Lynch S.R., and Puglisi J.D. J. Mol. Biol. 306 (2001) 1023-1035
33. Saenger W. Principles of Nucleic Acid Structure (1988), Springer-Verlag, Berlin
34. Meyer E.A., Castellano R.K., and Diederich F. Angew. Chem., Int. Ed. 42 (2003) 1210-1250
35. Pathak R., Böttger E.C., and Vasella A. Helv. Chim. Acta 88 (2005) 2967-2985
36. Fridman M., Belakhov V., Lee L.V., Liang F.S., Wong C.H., and Baasov T. Angew. Chem., Int. Ed. 44 (2005) 447-452
37. Hainrichson M., Pokrovskaya V., Shallom-Shezifi D., Fridman M., Belakhov V., Shachar D., Yaron S., and Baasov T. Bioorg. Med. Chem. 13 (2005) 5797-5807
38. Hanessian S., Masse R., and Capmeau M.L. J. Antibiot. 30 (1977) 893-896
39. Asensio J.L., Hidalgo A., Bastida A., Torrado M., Corzana F., Chiara J.L., Garcia-Junceda E., Canada J., and Jimenez-Barbero J. J. Am. Chem. Soc. 127 (2005) 8278-8279
40. Bastida A., Hidalgo A., Chiara J.L., Torrado M., Corzana F., Perez-Canadillas J.M., Groves P., Garcia-Junceda E., Gonzalez C., Jimenez-Barbero J., and Asensio J.L. J. Am. Chem. Soc. 128 (2006) 100-116
41. Blount K.F., Zhao F., Hermann T., and Tor Y. J. Am. Chem. Soc. 127 (2005) 9818-9829
42. Zhao F., Zhao Q., Blount K.F., Han Q., Tor Y., and Hermann T. Angew. Chem., Int. Ed. 44 (2005) 5329-5334
43. De Luca L., Giacomelli G., and Porcheddu A. Org. Lett. 3 (2001) 3041-3043
44. DeMico A., Margarita R., Parlanti L., Vescovi A., and Piancatelli G. J. Org. Chem. 62 (1997) 6974-6977
45. Pigro M.C., Angiuoni G., and Piancatelli G. Tetrahedron 58 (2002) 5459-5466
46. Sander P., Prammananan T., and Böttger E.C. Mol. Microbiol. 22 (1996) 841-848
47. Bayley H., Standring D.N., and Knowles J.R. Tetrahedron Lett. (1978) 3633-3634
48. Borch R.F., Bernstei Md., and Durst H.D. J. Am. Chem. Soc. 93 (1971) 2897
49. Prammananan T., Sander P., Springer B., and Böttger E.C. Antimicrob. Agents Chemother. 43 (1999) 447-453
50. Haskell T.H., French J.C., and Bartz Q.R. J. Am. Chem. Soc. 81 (1959) 3480-3481
51. Haskell T.H., French J.C., and Bartz Q.R. J. Am. Chem. Soc. 81 (1959) 3481
52. Haskell T.H., French J.C., and Bartz Q.R. J. Am. Chem. Soc. 81 (1959) 3481-3482
53. Haskell T.H., French J.C., and Bartz Q.R. J. Am. Chem. Soc. 81 (1959) 3482-3483
54. Bryskier A. Antimicrobial Agents (2005), ASM Press, Washington, DC pp 453-474