Chemical syntheses and in vitro antibacterial activity of two desferrioxamine B-ciprofloxacin conjugates with potential esterase and phosphatase triggered drug release linkers

Bioorganic and Medicinal Chemistry

Volumn 20, Issue 12, 2012, Pages 3828-3836

  Ji, Cheng ^a   Miller, Marvin J ^a  

^a UNIVERSITY OF NOTRE DAME   (United States)

Author keywords

Antibiotics; Drug delivery; Drug release; Iron transport; Siderophore conjugates

Indexed keywords

3 [2 [4 (BENZYLOXY)4 OXOBUTANOYLOXY] 4,6 DIMETHYLPHENYL] 3 METHYLBUTANOIC ACID; 3 [6 [[BIS(BENZYLOXY)PHOSPHORYL]OXY] 3 [(TERT BUTYLDIMETHYLSILYL)OXY] 2,4 DIMETHYLPHENYL] 3 METHYLBUTANOIC ACID; 4 [(TERT BUTYLDIMETHYLSILYL)OXY] 2 (4 HYDROXY 2 METHYLBUTAN 2 YL) 3,5 DIMETHYLPHENOL; 6 [(TERT BUTYLDIMETHYLSILYL)OXY] 4,4,5,7 TETRAMETHYLCHROMAN 2 ONE; BENZYL 2 (4 HYDROXY 2 METHYLBUTAN 2 YL) 3,5 DIMETHYLPHENYL SUCCINATE; BENZYL 2 [4 (TERT BUTYLDIMETHYLSILYLOXY) 2 METHYLBUTAN 2 YL] 3,5 DIMETHYLPHENYL SUCCINATE; BENZYL 3,5 DIMETHYL 2 (2 METHYL 4 OXOBUTAN 2 YL) PHENYL SUCCINATE; CIPROFLOXACIN; CIPROFLOXACIN CONJUGATE; DEFEROXAMINE; DEFEROXAMINE B CIPROFLOXACIN CONJUGATE; DIBENZYL [4 [(TERT BUTYLDIMETHYLSILYL)OXY] 2 (4 HYDROXY 2 METHYLBUTAN 2 YL) 3,5 DIMETHYLPHENYL] PHOSPHATE; DIBENZYL [4 [(TERT BUTYLDIMETHYLSILYL)OXY] 3,5 DIMETHYL 2 (2 METHYL 4 OXOBUTAN 2 YL) PHENYL] PHOSPHATE; ESTERASE; MEMBRANE PROTEIN; PHOSPHATASE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; CONFERENCE PAPER; DRUG RELEASE; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; MOLECULAR RECOGNITION; PROTEIN HYDROLYSIS;

ANTI-BACTERIAL AGENTS; CIPROFLOXACIN; DEFEROXAMINE; DRUG DELIVERY SYSTEMS; ESTERASES; GRAM-NEGATIVE BACTERIA; GRAM-POSITIVE BACTERIA; HYDROLYSIS; MICROBIAL SENSITIVITY TESTS; PHOSPHORIC MONOESTER HYDROLASES;

EID: 84861580404     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2012.04.034     Document Type: Conference Paper

References (38)

1. B. Spellberg, R. Guidos, D. Gilbert, J. Bradley, H.W. Boucher, W.M. Scheld, J.G. Bartlett, and J. Edwards Clin. Infect. Dis. 46 2008 155
2. H.W. Boucher, G.H. Talbot, J.S. Bradley, J.E. Edwards, D. Gilbert, L.B. Rice, M. Scheld, B. Spellberg, and J. Bartlett Clin. Infect. Dis. 48 2009 1
3. C. Walsh Antibiotics: Actions, Origins, Resistance 2003 American Society for Microbiology (ASM) Press Washington, DC
4. J.M. Pages, C.E. James, and M. Winterhalter Nat. Rev. Microbiol. 6 2008 893
5. J.M. Roosenberg, Y.M. Lin, Y. Lu, and M.J. Miller Curr. Med. Chem. 7 2000 159
6. V. Braun, A. Pramanik, T. Gwinner, M. Koberle, and E. Bohn Biometals 22 2009 3
7. V. Braun, K. Gunthner, K. Hantke, and L. Zimmermann J. Bacteriol. 156 1983 308
8. A. Hartmann, H.P. Fiedler, and V. Braun Eur. J. Biochem. 99 1979 517
9. U. Möllmann, L. Dong, L. Vertesy, and M.J. Miller The 2nd international Biometals symposium 2004 Garmisch-Partenkirchen
10. L. Vertesy, W. Aretz, H.W. Fehlhaber, and H. Kogler Helv. Chim. Acta 78 1995 46
11. F. Rivault, C. Liebert, A. Burger, F. Hoegy, M.A. Abdallah, I.J. Schalk, and G.L.A. Mislin Bioorg. Med. Chem. Lett. 17 2007 640
12. C. Hennard, Q.C. Truong, J.F. Desnottes, J.M. Paris, N.J. Moreau, and M.A. Abdallah J. Med. Chem. 44 2001 2139
13. S. Noel, V. Gasser, B. Pesset, F. Hoegy, D. Rognan, I.J. Schalk, and G.L.A. Mislin Org. Biomol. Chem. 9 2011 8288
14. S. Milstien, and L.A. Cohen J. Am. Chem. Soc. 94 1972 9158
15. R.T. Borchard, and L.A. Cohen J. Am. Chem. Soc. 94 1972 9166
16. S. Milstien, and L.A. Cohen Proc. Natl. Acad. Sci. U.S.A. 67 1970 1143
17. M.M. King, and L.A. Cohen J. Am. Chem. Soc. 105 1983 2752
18. M. Caswell, and G.L. Schmir J. Am. Chem. Soc. 102 1980 4815
19. T.J. Houghton, K.S.E. Tanaka, T. Kang, E. Dietrich, Y. Lafontaine, D. Delorme, S.S. Ferreira, F. Viens, F.F. Arhin, I. Sarmiento, D. Lehoux, I. Fadhil, K. Laquerre, J. Liu, V. Ostiguy, H. Poirier, G. Moeck, T.R. Parr, and A.R. Far J. Med. Chem. 51 2008 6955
20. R.B. Greenwald, Y.H. Choe, C.D. Conover, K. Shum, D.C. Wu, and M. Royzen J. Med. Chem. 43 2000 475
21. B.H. Wang, S. Gangwar, G.M. Pauletti, T.J. Siahaan, and R.T. Borchardt J. Org. Chem. 62 1997 1363
22. G.M. Pauletti, S. Gangwar, B.H. Wang, and R.T. Borchardt Pharm. Res. 14 1997 11
23. M.G. Nicolaou, C.S. Yuan, and R.T. Borchardt J. Org. Chem. 61 1996 8636
24. B.H. Wang, H.J. Zhang, and W. Wang Bioorg. Med. Chem. Lett. 6 1996 945
25. B.H. Wang, W. Wang, H.J. Zhang, D.X. Shan, and T.D. Smith Bioorg. Med. Chem. Lett. 6 1996 2823
26. K.L. Amsberry, A.E. Gerstenberger, and R.T. Borchardt Pharm. Res. 8 1991 455
27. K.L. Amsberry, and R.T. Borchardt Pharm. Res. 8 1991 323
28. U.T. Bornscheuer FEMS Microbiol. Rev. 26 2002 73
29. I.R. Beacham Int. J. Biochem. 10 1979 877
30. L.A. Mitscher Chem. Rev. 105 2005 559
31. G. Muller, and K.N. Raymond J. Bacteriol. 160 1984 304
32. L.A. Carpino, S.A. Triolo, and R.A. Berglund J. Org. Chem. 54 1989 3303
33. T.D. Nelson, J.D. Rosen, M. Bhupathy, J. McNamara, M.J. Sowa, C. Rush, and L.S. Crocker Org. Synth. 80 2003 219
34. T.A. Wencewicz, U. Möllmann, T.E. Long, and M.J. Miller Biometals 22 2009 633
35. S. Wilhelm, J. Tommassen, and K.E. Jaeger J. Bacteriol. 181 1999 6977
36. Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically, 8th ed.; Clinical and Laboratory Standards Institute (CLSI): Villanova, PA, USA, 2009, approved standard document M07-A7.
37. T.A. Wencewicz Dissertation 2011 University of Notre Dame Notre Dame, IN
38. J.M. Roosenberg II Dissertation 2000 University of Notre Dame Notre Dame, IN