Fluorescently-labeled ferrichrome analogs as probes for receptor-mediated, microbial iron uptake

Journal of the American Chemical Society

Volumn 118, Issue 49, 1996, Pages 12368-12375

  Weizman, Haim ^a   Ardon, Orly ^b   Mester, Brenda ^a   Libman, Jacqueline ^a   Dwir, Oren ^a   Hadar, Yitzhak ^b   Chen, Yona ^b   Shanzer, Abraham ^a  

^a WEIZMANN INSTITUTE OF SCIENCE   (Israel)

^b HEBREW UNIVERSITY OF JERUSALEM   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

FERRICHROME; SIDEROPHORE;

ARTICLE; DRUG SYNTHESIS; FLUORESCENCE; IRON TRANSPORT; NUCLEAR MAGNETIC RESONANCE; PROTEIN BINDING; PSEUDOMONAS PUTIDA;

EID: 0030457104     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9610646     Document Type: Article

References (43)

1. Winkelmann, G.; van der Helm, D.; Neilands, J. B. Iron Transport in Microbes, Plants and Animals; VCH Verlagsgesellschaft mbH, D-6940: Weinheim, Germany, 1987.
2. Neilands, J. B. Struct. Bonding 1984, 58, 1-24.
3. Matzanke, B. F.; Müller-Matzanke, G.; Raymond, K. N. Iron Carriers andiron Proteins; VCH Publishers: NY, 1989; Vol. 5, pp 1-121.
4. Hider, R. C. Struct. Bonding 1984, 58, 25-87.
5. Guerinot, M. L. Anna. Rev. Microbiol. 1994, 48, 743-772.
6. Bagg, A.; Neilands, J. B. Microbiology Rev. 1987, 51, 509-518.
7. Emery, T.; Emery, L.; Olsen, R. K. Biochem. Biophys. Res. Commun. 1984, 779, 1191-1197.
8. Winkelmann, G. FEBS Lett. 1979, 97, 43-46.
9. Winkelmann, G.; Braun, V. FEES Microbiol. Lett. 1981, 11, 237-241.
10. Neilands, J. B.; Erickson, T. J.; Rastetter, W. H. J. Biol. Chem. 1981, 250, 3831-3832.
11. Braun, V. In The Enzymes of Biological Membranes', Martonosi, A. N., Ed.; Plenum Press: NY, 1985; Vol. 3, pp 617-652.
12. Rutz, J. M.; Liu, J.; Lyons, J. A.; Goranson, J.; Armstrong, S. K.; Mclntosh, M. A.; Feiz, J. B.; Klebba, P. E. Science 1992, 258, 471-475.
13. Killmann, H.; Benz, R.; Braun, V. EMBO J. 1993, 12, 3000730016.
14. van der Helm, D.; Jalal, M. A. F.; Hossain, M. B. In Iron Transport in Microbes, Plants and Animals; Winkelmann, G., van der Helm, D., Neilands, J. B., Eds.; VCH Verlagsgesellschaft mbH, D-69451: Weinheim, Germany, 1987; pp 135-166.
15. Jalal, M. A. F.; van der Helm, D. In Handbook of Microbial Iron Chelates; Winkelmann, G., Ed.; CRC Press: Boca Raton, Ann Arbor, Boston, London, 1991; pp 235-269.
16. Shanzer, A.; Libman, J. In Handbook of Microbial Iron Chelates; Winkelmann, G., Ed.; CRC: Boca Raton, Ann Arbor, Boston, London, 1991; pp 309-338.
17. Shanzer, A.; Libman, J; Yakirevitch, P.; Hadar, Y.; Chen, Y.; Jurkevitch, E. Chirality 1993, 5, 359-365.
18. Breslow, R. Cliem. Soc. Rev. 1972, /, 553-580.
19. Tor, Y.; Libman, J.; Shanzer, A.; Felder, C. E.; Lifson, S. J. Am. Cliem. Soc. 1992, 114, 6661-6671.
20. Dayan, L; Libman, J.; Agi, Y.; Shanzer, A. Inorg. Chem. 1993,32, 1467-1475.
21. Yakirevitch, P.; Rochel, N.; Albrecht-Gary, A.-M.; Libman, J.; Shanzer, A. Inorg. Chem. 1993, 32, 1779-1787.
22. Shanzer, A.; Libman, J; Lazar, R.; Tor, Y.; Emergy, T, Biochem. Biophys. Res. Commun. 1988, 757, 389-394.
23. Jurkevitch, E.; Hadar, Y.; Chen, Y.; Libman, J.; Shanzer, A. J. Bacterial. 1992, 174, 78-83.
24. Bemer, L; Yakirevitch, P.; Libman, J.; Shanzer, A.; Winkelmann, G. Biol. Metals 1991, 4, 186-191.
25. Jurkevitch, E.; Hadar, Y.; Chen, Y.; Yakirevitch, P.; Libman, J.; Shanzer, A. Microbiology-UK 1994, 140, 1697-1703.
26. Tsien, R. Y. Ann. Rev. Neurosci. 1989, 72, 227-253.
27. Bodenant, B.; Pages, F. Tetrahedron Lett. 1995, 36, 1451-1454.
28. Barrero, M.; Cámara, C; Pérez-Conde, M. C; José, C. S.; Fernández, L. Analyst 1995, 720, 431-435.
29. Barrero, J. M.; Morenobondi, M. C.; Pérez-Conde, M. C.; Camara, C. Talanta 1993, 40, 1619-1623.
30. Czarnik, A. W. Ace. Chem. Res. 1994, 27, 302-308.
31. Bissell, R. A.; Silva, A. P. d.; Gunaratne, H. Q. N.; Lynch, P. L. M.; Maguire, G. E. M.; Sandanayake, K. R. A. S. Chem. Soc. Rev. 1992, 21, 187-195.
32. Fabbrizzi, L.; Licchelli, M.; Pallavicini, P.; Perotti, A.; Sacchi, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 1975-1977.
33. Fabbrizzi, L.; Poggi, A. Chem. Soc. Rev. 1995, 24, 197-202.
34. Lytton, S. D.; Cabantchik, Z. I.; Libman, J.; Shanzer, A. Mol. Pharmacol 1991, 40, 584-590.
35. Lytton, S. D.; Mester, B.; Libman, J.; Shanzer, A.; Cabantchik, Z. I. Anal. Biochem. 1992, 205, 326-333.
36. Bar-ness, E.; Hadar, Y.; Chen, Y.; Shanzer, A.; Libman, J. Plant Physiol. 1992, 99. 1329-1335.
37. Loyevsky, M.; Lytton, S. D.; Mester, B.; Libman, J.; Shanzer, A.; Cabantchik, Z. I. J. Clin. Investigations 1993, 91, 218-224.
38. 2.
39. Although the binding constants of hydroxamate siderophores to iron(III) are higher than those of EDTA (log K ∼30 and 25, respectively), the apparent binding constant of the synthetic ferrichrome analogs 5 is comparable to that of EDTA under our experimental conditions, with pFe values of 15. EDTA may thus effectively compete with the ferrichrome analogs for iron(III).
40. Nakamura, T.; Kira, A.; Imamura, M. J. Phys. Chem. 1983, 87, 3122-3125.
41. Donckt, E. V.; vanVooren, C. J. Chem. Soc. Faraday Trans. 1 1978, 74, 827-836.
42. Because of the small size of bacteria, fluorescence microscopy of bacterial cultures (even at lOOOx magnifications) does not enable distinguishing between fluorescence inside and outside the organisms and is thus of little diagnostic value with regards to the fluorescent siderophore analogs described here. In contrast to bacteria, fungi lend themselves to fluorescence microscopy studies. The latter possibilities are under current investigation.
43. Ardon, O.; Nudelman, R.; Weizman, H.; Hadar, V.; Libman, J.; Shanzer, A. Preliminary results, 1996.