Siderophore conjugates

Annals of the New York Academy of Sciences

Volumn 1277, Issue 1, 2013, Pages 115-126

  Page, Malcolm G P ^a  

^a BASILEA PHARMACEUTICA INTERNATIONAL LTD   (Switzerland)

Author keywords

BAL30072; Iron transport; Sideromycin; Siderophore antibiotics

Indexed keywords

ANTIBIOTIC AGENT; BAL 30072; BETA LACTAM ANTIBIOTIC; GLYCOPEPTIDE; MACROLIDE; NUCLEOSIDE; QUINOLONE DERIVATIVE; SIDEROPHORE; UNCLASSIFIED DRUG;

ACINETOBACTER; ANTIBACTERIAL ACTIVITY; ARTICLE; CONJUGATE; ESCHERICHIA COLI; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE BACTERIUM; NONHUMAN; PSEUDOMONAS AERUGINOSA; STENOTROPHOMONAS MALTOPHILIA; YERSINIA PESTIS;

EID: 84872850695     PISSN: 00778923     EISSN: 17496632     Source Type: Book Series    
DOI: 10.1111/nyas.12024     Document Type: Article

References (80)

1. Raymond, K.N., G. Müller & B.F. Matzanke 1984. Complexation of iron by siderophores. A review of their solution and structural chemistry and biological function. Top. Curr. Chem 123: 49-102.
2. Mullié, F.S., A. Dassonville-Klimpt, N. Audic, et al. 2011. Bacterial iron uptake: a promising solution against multidrug resistant bacteria. In Science Against Microbial Pathogens: Communicating Current Research and Technological Advances Formatex, Microbiology Book Series Number 3, Vol. 2. A. Méndez-Vilas, Ed.: 695-704. Formatex Research Center. Badajoz, Spain
3. Möllmann, U., L. Heinisch, A. Bauernfeind, et al. 2009. Siderophores as drug delivery agents: application of the "Trojan Horse" strategy. Biometals 22: 615-624.
4. van der Helm, D. & R.N. Chakraborty 2001. Structures of Siderophore Receptors In Microbial Transport Systems G. Winkelmann, Ed.: 261-288. Wiley-VCH Verleg GmbH. Weinheim, Germany
5. Tennyson, A. 1850. In Memoriam A. H. H., Canto 56.
6. Vassiliadis, G., D. Destoumieux-Garzón, C. Lombard, et al. 2010. Isolation and characterization of two members of the siderophore-microcin family, microcins M and H47. Antimicrob. Agents Chemother. 54: 288-297.
7. Morin, N., I. Lannelue, N. Connil, et al. 2011. Mecganism and bactericidal activity of Microcin L in Escherichia coli and Salmonella enterica. Antimicrob. Agents Chemother 55: 899-1007.
8. Braun, V., A. Pramanik, T. Gwinner, et al. 2009. Sideromycins: tools and antibiotics. Biometals 22: 3-13.
9. Gause, G.F. 1955. Recent studies on albomycin, a new antibiotic. BMJ 12: 1177-1179.
10. Hartmann, A., H.-P. Fiedler & V. Braun 1979. Uptake and conversion of the antibiotic albomycin by Escherichia coli K-12. Eur. J. Biochem 99: 517-524.
11. Bickel, H., P. Mertens, V. Prelog, et al. 1965. Constitution of ferrimycin A1. Antimicrob. Agents Chemother 5: 951-957.
12. Vertesy, L., W. Aretz, H.W. Fehlhaber & H. Kogler 1995. Salmycin A.-D., antibiotika aus Streptomyces violaceus, DSM 8286, mit siderophor-aminoglycosid-struktur. Helv. Chim. Acta 78: 46-60.
13. Miyakawa, S., T. Noto & H. Okazaki 1982. Mechanisms of resistance in Escherichia coli to the sideromycin antibiotic no. 216: isolation and characterization of the resistant mutants. Microbiol. Immunol 26: 885-895.
14. Ghosh, M. & M.J. Miller 1995. Design, synthesis and biological evaluation of isocyanurate-based antifungal and macrolide antibiotic conjugates: iron transport-mediated drug delivery. Biorganic Med. Chem. 3: 1519-1525.
15. Lu, Y. & M.J. Miller. 1999. Syntheses and studies of multiwarhead siderophore-5-fluorouridine conjugates. Biorganic Med. Chem. 7: 3025-3038.
16. Ghosh, M. & M.J. Miller 1996. Synthesis and in vitro antibacterial activity of spermidine-based mixed catechol- and hydroxamate-containing siderophore-vancomycin conjugates. Biorganic Med. Chem. 4: 43-48.
17. Md-Saleh, S.R., E.C. Chilvers, K.G. Kerr, et al. 2009. Synthesis of citrate-ciprofloxacin conjugates. Biorganic Med. Chem. Lett. 19: 1496-1498.
18. Ji, C. & M.J. Miller 2012. Chemical syntheses and in vitro antibacterial activity of two desferrioxamine B-ciprofloxacin conjugates with potential esterase and phosphatase triggered drug release linkers. Bioorganic Med. Chem. 20: 3828-3836.
19. Noël, S., V. Gasser, B. Pesset, et al. 2011. Synthesis and biological properties of conjugates between fluoroquinolones and a N3″-functionalized pyochelin. Org. Biomol. Chem. 9: 8288-8300.
20. Rivault, F., C. Liebert, A. Burger, et al. 2007. Synthesis of pyochelin-norfloxacin conjugates. Bioorg. Med. Chem. Lett. 17: 640-644.
21. Berbier, G., V. Girijavallabhan, A. Murray, et al. 2005. Desketoneoeanactin-siderophore conjugates for Candida: evidence of iron transport-dependent species selectivity. Antimicrob. Agents Chemother. 49: 241-248.
22. Dini, C. & J. Aszodi 2000. Synthesis of a dihydroxythiophene analogue of catechosporines. Bioorganic Med. Chem. Lett. 10: 349-352.
23. Wittmann, S., I. Scherlitz-Hofmann, U. Möllmann, et al. 2000. 8-Acyloxy-1, 3-benzoxazine-2, 4-diones as siderophore components for antibiotics. Arzneimittelforschung 50: 752-757.
24. Kline, T., M. Fromhold, T. E. McKennon, et al. 2000. Antimicrobial effects of novel siderophores linked to beta-lactam antibiotics. Bioorg. Med. Chem 8: 73-93.
25. Heinisch, L., S. Wittmann, T. Stoiber, et al. 2002. Highly antibacterial active aminoacyl penicillin conjugates with bis-catecholate siderophores based on secondary diamino acids and related compounds. J. Med. Chem. 45: 3032-3040.
26. Heinisch, L., S. Wittmann, T. Stoiber, et al. 2003. New tris- and tetrakis-catecholate siderophores based on polyazaalkanoic acids and their β-lactam conjugates. Arzneim.-Forschung Drug Res 53: 188-195.
27. Ohi, N., B. Aoki, T. Shinozaki, et al. 1987. Semisynthetic beta-lactam antibiotics. IV. Synthesis and antibacterial activity of new ureidocephalosporin and ureidocephamycin derivatives containing a catechol moiety or its acetate. Chem. Pharm. Bull. (Tokyo) 35: 1903-1909.
28. Mochizuki, H., H. Yamada, Y. Oikawa, et al. 1988. Bactericidal activity of M14659 enhanced in low-iron environments. Antimicrob. Agents Chemother. 32: 1648-1654.
29. Silley, P., J.W. Griffiths, D. Monsey & A.M. Harris 1990. Mode of action of GR69153, a novel catechol-substituted cephalosporin, and its interaction with the tonB-dependent iron transport system. Antimicrob. Agents Chemother 34: 1806-1808.
30. Hashizume, T., M. Sanada, S. Nakagawa & N. Tanaka 1990. Comparison of transport pathways of catechol-substituted cephalosporins, BO-1236 and BO-1341, through the outer membrane of Escherichia coli. J. Antibiot. (Tokyo) 43: 1617-1620.
31. Arisawa, M., Y. Sekine, S. Shimizu, et al. 1991. In vitro and in vivo evaluation of Ro 09-1428, a new parenteral cephalosporin with high antipseudomonal activity. Antimicrob. Agents Chemother. 35: 653-659.
32. McKee, J.A. & M.J. Miller 1991. Synthesis, siderophore and antimicrobial evaluation of a spermidine-based tricatecholatesiderophore and carbacephalosporin conjugate. Biorganic Med. Chem. Lett. 1: 513-518.
33. Brochu, A., N. Brochu, T.I. Nicas, et al. 1992. Modes of action and inhibitory activities of new siderophore-beta-lactam conjugates that use specific iron uptake pathways for entry into bacteria. Antimicrob. Agents Chemother 36: 2166-2175.
34. Minnick, A.A., J.A. McKee, E.K. Dolence & M.J. Miller 1992. Iron transport-mediated antibacterial activity of and development of resistance to hydroxamate and catechol siderophore-carbacephalosporin conjugates. Antimicrob Agents Chemother. 36: 840-850.
35. Jones, R.N. & M.E. Erwin 1992. In vitro evaluation of Ro 09-1227, a novel catechol-substituted cephalosporin. Antimicrob. Agents Chemother 36: 233-238.
36. Arnould, J.C., A. Bertrandie, T.G. Bird, et al. 1992. Synthesis and structure-activity relationships of cephalosporins with C-3' catechol-containing residues. J. Med. Chem. 35: 2631-2642.
37. Imae, K., S. Imura, T. Hasegawa, et al. 1993. Cephalosporins having a heterocyclic catechol in the C3 side chain. I. Enhancement of efficacy against gram-negative bacteria. J. Antibiot. (Tokyo) 46: 840-849.
38. Okita, T., K. Imae, T. Hasegawa, et al. 1993. Synthesis and antibacterial activity of cephalosporins having a catechol in the C3 side chain. J. Antibiot. (Tokyo) 46: 833-839.
39. Jones, R.N. & M.L. Sanchez 1994. Antimicrobial activity of a new antipseudomonal dual-action drug, Ro 25-0534. Diagn. Microbiol. Infect. Dis. 18: 61-68.
40. Song, H.K., J.I. Oh, M.Y. Kim, et al. 1996. In-vitro and in-vivo antibacterial activity of LB10517, a novel catechol-substituted cephalosporin with a broad antibacterial spectrum. J. Antimicrob. Chemother 37: 711-726.
41. Kim, Y.Z., J.C. Lim, J.H. Yeo, et al. 1996. Synthesis and antibacterial activities of novel C(7)-catechol-substituted cephalosporins (I). J. Antibiot. (Tokyo) 49: 496-498.
42. Kim, Y.Z., J.C. Lim, J.H. Yeo, et al. 1996. Synthesis and antibacterial activities of novel C(7)-catechol-substituted cephalosporins (II). J. Antibiot. (Tokyo) 49: 499-501.
43. Erwin, M.E., D. Varnam & R.N. Jones 1997. In vitro antimicrobial activity of RU-59863, a C-7 catechol substituted cephalosporin. Diagn. Microbiol. Infect. Dis. 28: 93-100.
44. Choi, K.I., J.H. Cha, A.N. Pae, et al. 1997. Studies on new catechol containing cephalosporins. III. Synthesis and structure-activity relationships of cephalosporins having a pyridone moiety at the C-7 position. J. Antibiot. (Tokyo) 50: 279-282.
45. Möllmann, U., A. Ghosh, E.K. Dolence, et al. 1998. Selective growth promotion and growth inhibition of gram-negative and gram-positive bacteria by synthetic siderophore-beta-lactam conjugates. Biometals 11: 1-12.
46. Curtis, N.A., R.L. Eisenstadt, S.J. East, et al. 1988. Iron-regulated outer membrane proteins of Escherichia coli K-12 and mechanism of action of catechol-substituted cephalosporins. Antimicrob. Agents Chemother 32: 1879-1886.
47. Nikaido, H. & E.Y. Rosenberg 1990. Cir and Fiu proteins in the outer membrane of Escherichia coli catalyze transport of monomeric catechols: study with beta-lactam antibiotics containing catechol and analogous groups. J. Bacteriol. 172: 1361-1367.
48. Critchley, I.A., M.J. Basker, R.A. Edmondson & S.J. Knott 1991. Uptake of a catecholic cephalosporin by the iron transport system of Escherichia coli. J. Antimicrob. Chemother 28: 377-388.
49. Gensberg, K., E.J. Doyle, D.J. Perry & A.W. Smith 1994. Uptake of BRL 41897A, a C(7) alpha-formamido substituted cephalosporin, via the ferri-pyochelin transport system of Pseudomonas aeruginosa. J. Antimicrob. Chemother. 34: 697-705.
50. Hoegy, F., M.N. Gwynn & I.J. Schalk 2010. Susceptibility of Pseudomonas aeruginosa to catechol-substituted cephalosporin is unrelated to the pyochelin-Fe transporter FptA. Amino Acids 38: 1627-1629.
51. Bäumler, A., R. Koebnik, I. Stojiljkovic, et al. 1993. Survey on newly characterized iron uptake systems of Yersinia enterocolitica. ZentralblBakteriol. 278: 416-424.
52. Mochida, K., Y. Ono, M. Yamasaki, et al. 1987. Aminothiazolylglycyl derivatives of carbacephem antibiotics. II. Synthesis and antibacterial activity of novel aminothiazolylcephem compounds with hydroxypyridone moiety. J. Antibiot. (Tokyo) 40: 182-189.
53. Maejima, T., M. Inoue & S. Mitsuhashi 1991. In vitro antibacterial activity of KP-736, a new cephem antibiotic. Antimicrob. Agents Chemother 35: 104-110.
54. Tatsumi, Y., T. Maejima & S. Mitsuhashi 1995. Mechanism ottonB-dependent transport of KP-736, a 1, 5-dihydroxy-4-pyridinone-substituted cephalosporin, into Escherichia coli K-12 cells. Antimicrob. Agents Chemother 39: 613-619.
55. Dolence, E.K., A.A. Minnick & M.J. Miller 1990. N5-acetyl-N5-hydroxy-L-ornithine-derived siderophore-carbacephalosporin beta-lactam conjugates: iron transport mediated drug delivery. J. Med. Chem. 33: 461-464.
56. Dolence, E.K., A.A. Minnick, C.E. Lin, et al. 1991. Synthesis and siderophore and antibacterial activity of N5-acetyl-N5-hydroxy-L-ornithine-derived siderophore-beta-lactam conjugates: iron-transport-mediated drug delivery. J. Med. Chem. 34: 968-978.
57. Miller, M.J., J.A. McKee, A.A. Minnick & E.K. Dolence 1991. The design, synthesis and study of siderophore-antibiotic conjugates. Siderophore mediated drug transport. Biol. Met. 4: 62-69.
58. Kinzel, O. & H. Budzikiewicz 1999. Synthesis and biological evaluation of a pyoverdin-beta-lactam conjugate: a new type of arginine-specific cross-linking in aqueous solution. J. Pept. Res. 53: 618-625.
59. Ghosh, A., M. Ghosh, C. Niu, et al. 1996. Iron transport-mediated drug delivery using mixed-ligand siderophore-β-lactam conjugates. Chem. Biol. 3: 1011-1019.
60. Sykes, R.B., W.H. Koster & D.P. Bonner 1988. The new monobactams: chemistry and biology. J. Clin. Pharmacol 28: 113-119
61. Barbachyn, M.R. & T.C. Tuominen 1990. Synthesis and structure-activity relationships of monocarbams leading to U-78608. J. Antibiotics (Tokyo) 43: 1199-1202.
62. Han, S., R.P. Zaniewski, E.S. Marr, et al. 2010. Structural basis for effectiveness of siderophore-conjugated monocarbams against clinically relevant strains of Pseudomonas aeruginosa. Proc. Natl. Acad. Sci. USA 21: 22002-22007.
63. Zurenko, G.E., S.E. Truesdell, B.H. Yagi, et al. 1990. In vitro antibacterial activity and interactions with beta-lactamases and penicillin-binding proteins of the new monocarbam antibiotic U-78608. Antimicrob. Agents Chemother. 34: 884-888.
64. Han, S., N. Caspers, R.P. Zaniewski, et al. 2011. Distinctive attributes of β-lactam target proteins in Acinetobacter baumannii relevant to development of new antibiotics. J. Am. Chem. Soc. 133: 20536-20545.
65. McPherson, C.J., L.M. Aschenbrenner, B.M. Lacey, et al. 2012. Clinically relevant Gram-negative resistance mechanisms have no effect on the efficacy of MC-1, a novel siderophore-conjugated monocarbam. Antimicrob. Agents Chemother. 56: 6334-6342.
66. McKee, J.A., S.K. Sharma & M.J. Miller 1991. Iron transport mediated drug delivery systems: synthesis and antibacterial activity of spemidine- and lysine-based siderophore-β-lactam conjugates. Bioconjugate Chem 2: 281-291.
67. Fung-Tomc, J., K. Bush, B. Minassian, et al. 1997. Antibacterial activity of BMS-180680, a new catechol-containing monobactam. Antimicrob. Agents Chemother. 41: 1010-1016.
68. Livermore, D.M., S. Mushtaq & M. Warner 2010. Activity of BAL30376 (monobactam BAL19764 + BAL29880 + clavulanate) versus Gram-negative bacteria with characterized resistance mechanisms. J. Antimicrob. Chemother. 65: 2382-2395.
69. Page, M.G.P., C. Dantier, E. Desarbre, et al. 2011. In vitro and in vivo propertiesof BAL30376, a β-lactam and dual β-lactamase inhibitor combination with enhanced activity against Gram-negative bacilli that express multiple β-lactamases. Antimicrob. Agents Chemother 55: 1510-1519.
70. Page, M.G.P., C. Dantier & E. Desarbre 2010. In vitro properties of BAL30072, a novel siderophore sulfactam with activity against multiresistant Gram-negative bacteria. Antimicrob. Agents Chemother 54: 2291-2302.
71. Mushtaq, S., M. Warner & D. Livermore 2010. Activity of the siderophore monobactam BAL30072 against multiresistant non-fermenters. J. Antimicrob. Chemother. 65: 266-270.
72. Mima, T., B.H. Kvitko, D.A. Rholl, et al. 2011. In vitro activity of BAL30072 against Burkholderia pseudomallei. Int. J. Antimicrob Agents 38: 157-159.
73. Russo, T.A., M.G.P. Page, J.M. Beanan, et al. 2011. In vivo and in vitro activity of the siderophore monosulfactam BAL30072 against Acinetobacter baumannii. J. Antimicrob. Chemother 66: 867-873.
74. Higgins, P.G., D. Stefanik, M.G.P. Page, et al. 2012. In vitro activity of the siderophore monosulfactam BAL30072 against meropenem-non-suceptible Acinetobacter baumannii. J. Antimicrob. Chemother 67: 1167-1169.
75. st Intersci. Conf. Antimicrob. Agents Chemother., Abstr. American Society for Microbiology, Washington, DC
76. th Intersci. Conf. Antimicrob. Agents Chemother., Abstr. American Society for Microbiology, Washington, DC
77. thIntersci. Conf. Antimicrob. Agents Chemother., Abstr. American Society for Microbiology, Washington, DC
78. Milne, T.S., S.L. Micell, H. Diaper, et al. 2007. A 55 kDA hypothetical membrane protein is an iron-regulated virulence factor of Franciscella tularensis subsp. novicida U112. J. Med. Microbiol. 56: 1268-1276.
79. Fetherston, J.D., O. Kirillina, A.G. Bobrov, et al. 2010. The yersiniabactin transport system is critical for the pathogenesis of bubonic and pneumonic plague. Infect. Immun 78: 2045-2052.
80. Takase, H., H. Nitani, K. Hoshino & T. Otani 2000. Impact of siderophore production on Pseudomonas aeruginosa infections in immunosuppressed mice. Infect. Immun. 68: 1834-1839.