Syntheses of siderophore-drug conjugates using a convergent thiol-maleimide system

ACS Medicinal Chemistry Letters

Volumn 3, Issue 10, 2012, Pages 799-803

  Juárez Hernández, Rál E ^a   Miller, Patricia A ^a   Miller, Marvin J ^a  

^a UNIVERSITY OF NOTRE DAME   (United States)

Author keywords

Antibiotic; drug conjugate; siderophore

Indexed keywords

AMPICILLIN; CIPROFLOXACIN; DEFEROXAMINE; LORACARBEF; MALEIMIDE; NADIFLOXACIN; SILICA GEL; THIOL;

ACYLATION; ANTIBACTERIAL ACTIVITY; ARTICLE; CONJUGATE; DRUG ISOLATION; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ESCHERICHIA COLI; GEL CHROMATOGRAPHY; GRAM POSITIVE BACTERIUM; MINIMUM INHIBITORY CONCENTRATION; MYCOBACTERIUM SMEGMATIS; MYCOBACTERIUM VACCAE; NONHUMAN; PRECURSOR; PRIORITY JOURNAL;

EID: 84867393274     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml300150y     Document Type: Article

References (31)

1. Miethke, M.; Marahiel, M. A. Siderophore-Based Iron Acquisition and Pathogen Control Microbiol. Mol. Biol. Rev. 2007, 71, 413-451
2. Boukhalfa, H.; Crumbliss, A. L. Chemical aspects of siderophore mediated iron transport Biometals 2002, 15, 325-339
3. Andrews, S. C.; Robinson, A. K.; Rodríguez-Quiñones, F. Bacterial iron homeostasis FEMS Microbiol. Rev. 2003, 27, 215-237
4. Sandy, M.; Butler, A. A Microbial Iron Acquisition: Marine and Terrestrial Siderophores Chem. Rev. 2009, 109, 4580-4595
5. Hider, R. C.; Kong, X. L. Chemistry and biology of siderophores Nat. Prod. Rep. 2010, 27, 637-657
6. Braun, V.; Hantke, K. Recent insights into iron import by bacteria Curr. Opin. Chem. Biol. 2011, 15, 328-334
7. Benz, G.; Schröder, T.; Kurz, J.; Wünsche, C.; Karl, W.; Steffen, G. J.; Pfitzner, J.; Schmidt, D. Konstitution der Deferriform der Albomycine δ1, δ2 und ε Angew. Chem., Int. Ed. 1982, 94, 552-553
8. Braun, V.; Günthner, K.; Hantke, K.; Zimmerman, L. Intracellular Activation of Albomycin in Escherichia coli and Salmonella t yphimurium J. Bacteriol. 1983, 156, 308-315
9. Vértesy, L.; Aretz, W.; Fehlhaber, H.-W.; Kogler, H.; Salmycin, A.-D. Antibiotics from Streptomyces violaceus, DSM 8286, Having a Siderophore-Aminoglycoside Structure Helv. Chim. Acta 1995, 78, 46-60
10. Duquesne, S.; Destoumieux-Garzón, D.; Peduzzi, J.; Rebuffat, S. Microcins, gene-encoded antibacterial peptides from enterobacteria Nat. Prod. Rep. 2007, 24, 708-734
11. Nolan, E. M.; Fischbach, M. A.; Koglin, A.; Walsh, C. T. Biosynthethic Tailoring of Microcin E492m: Post-translational Modification Affords an Antibacterial Siderophore-Peptide Conjugate J. Am. Chem. Soc. 2007, 129, 14336-14347
12. Dong, L.; Roosenberg, J. M., II; Miller, M. J. Total Synthesis of Desferrisalmycin B J. Am. Chem. Soc. 2002, 124, 15001-15005
13. Bernier, G.; Girijavallabhan, V.; Murray, A.; Niyaz, N.; Ding, P.; Miller, M. J.; Malouin, F. Desketoneoenactin-Siderophore Conjugates for Candida: Evidence of Iron Transport-Dependent Species Selectivity Antimicrob. Agents Chemother. 2005, 49, 241-248
14. Yoganathan, S.; Sit, C. S.; Vederas, J. C. Chemical synthesis and biological evaluation of gallidermin-siderophore conjugates Org. Biomol. Chem. 2011, 9, 2133-2141
15. Miller, M. J.; Walz, A. J.; Zhu, H.; Wu, C.; Moraski, G.; Möllmann, U.; Tristani, E. M.; Crumbliss, A. L.; Ferdig, M. T.; Checkley, L.; Edwards, R. L.; Boshoff, H. I. Design, Synthesis, and Study of a Mycobactin-Artemisinin Conjugate That Has Selective and Potent Activity against Tuberculosis and Malaria J. Am. Chem. Soc. 2011, 133, 2076-2079
16. Roosenberg, J. M., II; Lin, Y. M.; Lu, Y.; Miller, M. J. Studies and Syntheses of Siderophores, Microbial Iron Chelators, and Analogs as Potential Drug Delivery Agents Curr. Med. Chem. 2000, 7, 159-197
17. Braun, V.; Pramanik, A.; Gwinner, T.; Koeberle, M.; Bohn, E. Sideromycins: tools and antibiotics Biometals 2009, 22, 3-13
18. Chu, B. C.; Garcia-Herrero, A.; Johanson, T. H.; Krewulak, K. D.; Lau, C. K.; Peacock, R. S.; Slavinskaya, Z.; Vogel, H. J. Siderophore uptake in bacteria and the battle for iron with the host; a birds eye view Biometals 2010, 23, 601-611
19. Ji, C.; Juárez-Hernández, R. E.; Miller, M. J. Exploiting bacterial iron acquisition: siderophore conjugates Future Med. Chem. 2012, 4, 297-313
20. 67Ga-labeled Antibodies for Immunoscintigraphy and Evaluation of Tumor Targeting and Drug-Antibody Conjugates in Mice Cancer Res. 1988, 48, 1189-1194
21. Arano, Y.; Matsushima, H.; Tagawa, M.; Koizumi, M.; Endo, K.; Konishi, J.; Yokoyama, A. A Novel Bifunctional Metabolizable Linker for the Conjugation of Antibodies with Radionuclides Bioconjugate Chem. 1991, 2, 71-76
22. 89Zr-labeled monoclonal antiodies for ImmunoPET Nucl. Med. Biol. 2010, 37, 289-297
23. Collman, J. P.; Groh, S. E. "Mercaptan-Tail" Porphyrins: Synthetic Analogues for the Active Site of Cytochrome P-450 J. Am. Chem. Soc. 1982, 104, 1391-1403
24. Moreno, A. Y.; Mayorov, A. V.; Janda, K. D. Impact of Distinct Chemical Structures for the Development of a Methamphetamine Vaccine J. Am. Chem. Soc. 2011, 133, 6587-6595
25. Kaneko, Y.; Thoendel, M.; Olakanmi, O.; Britigan, B. E.; Singh, P. K. The transition metal gallium disrupts Pseudomonas aeruginosa iron metabolism and has antimicrobial and antibiofilm activity J. Clin. Invest. 2007, 117, 877-888
26. Banin, E.; Lozinski, A.; Brady, K. M.; Berenshtein, E.; Butterfield, P. W.; Moshe, M.; Chevion, M.; Greenberg, E. P.; Banin, E. The potential of desferrioxamine-gallium as an anti- Pseudomonas therapeutic agent Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 16761-16766
27. 19F-NMR Structure Analysis of Membrane Associated Peptides ChemBioChem 2003, 4, 1151-1163
28. Murray, P. R.; Baron, E. J.; Pfaller, M. A.; Tenover, F. C.; Yolken, R. H. Manual of Clinical Microbiology, 7 th ed.; American Society for Microbiology: Washington, DC, 1999.
29. Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically, 8 th ed.; Clinical and Laboratory Standards Institute (CLSI): Villanova, PA, 2009; approved standard document M07-A7.
30. Young, M.; Artsatbanov, V.; Beller, H. R.; Chandra, G.; Chater, K. F.; Dover, L. G.; Goh, E.-B.; Kahan, T.; Kaprelyants, A. S.; Kyrpides, N.; Lapidus, A.; Lowry, S. R.; Lykidis, A.; Mahillon, J.; Markowitz, V.; Mavromatis, K.; Mukamolova, G. V.; Oren, A.; Rokem, J. S.; Smith, M. C. M.; Young, D. I.; Greenblatt, C. L. Genome Sequence of the Fleming Strain of Micrococcus luteus, a Simple Free-Living Actinobacterium J. Bacteriol. 2010, 192, 841-860
31. 3+ Is Influenced by Ligand Complexation as Well as the Bacterial Carbon Source Antimicrob. Agents Chemother. 2011, 55, 5568-5580