Abstract
New analogues of triscatecholate siderophores based on linear or tripodal triamines with or without spacer groups or lipophilic and hydrophilic substituents were synthesized. The catecholate moieties were prepared in OH-forms, as acetylated compounds or masked as 8-methoxycarbonyloxy-2,4-dioxo-1,3-benzoxazine derivatives. Some of the new compounds were active as siderophores tested by growth promotion assays using various Gram-negative bacteria and mycobacteria under iron limitation and by CAS-assay. Structure-activity-correlations have been studied.
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Ambrosi HD, Hartmann V, Pistorius D, Reissbrodt R, Trowitzsch-Kienast W. 1998 Myxochelins B, C, D, E and F: A New Structural Principle for Powerful Siderophores Imitating Nature. Eur J Org Chem 541-551.
Arisawa M, Sekine Y, Shimizu S, Takano H, Angehrn P, Then RL. 1991 In Vitro and In Vivo Evaluation of Ro 09-1428, a New Parenteral Cephalosporin with High Antipseudomonal Activity. Antimicrob Ag Chemother 35, 653-659.
Bergeron RJ, McGovern KA, Channing MA, Burton PS. 1980 Synthesis of N4-Acylated N1, N8-Bis(acyl)spermidines: An Approach to the Synthesis of Siderophores. J Org Chem 45, 1589-1592.
Bergeron RJ, Kline SJ, Stollowich NJ, McGovern KA, Burton PS. 1981 Flexible Synthesis of Polyamine Catecholamides. J Org Chem 46, 4524-4529.
Buckley GM, Pattenden G, Whiting DA. 1994 New Synthetic Probes of the Iron Transport System of Paracoccus denitrificans. Tetrahedron 50, 11781-11792.
Cheraiti N, Brik ME, Gaudemer A, Kunesh G. 1999 Synthesis and electrochemical study of a new chiral tris-catecholamide analogue of enterobactin. Bioorg Med Chem Lett 9, 781-786.
Drechsel H, Jung G. 1998 Peptide Siderophores. J Peptide Sci 4, 147-181.
Griffith GL, Sigel SP, Payne SM, Neilands JB. 1984 Vibriobactin, a Siderophore from Vibrio cholerae. J Biol Chem 259, 383-385.
Miyasaka T, Yoshimitsu N, Fujita E, Sakurai H, Ishizu K. 1987 Synthesis of parabactin Analogues and Formation of Transition Metal Complexes of parabactin and Related Compounds. J Chem Soc Perkon Trans II 1543-1550.
Okujo N, Saito M, Yamamoto S, Yoshida T, Miyoshi S, Shinoda S. 1994 Structure of vulnibactin, a new polyamine-containing siderophore from Vibrio vulnificus. BioMetals 7, 109-116.
Ong SA, Peterson T, Neilands JB. 1979 Agrobactin, a Siderophore from Agrobacterium tumefaciens. J Biol Chem 254, 1860-1865.
Pradines B, Ramiandrasoa F, Basco L.K., Bricard L. Kunesch G, LeBras J. 1996 In Vitro Activities of Novel Catecholate Siderophores against Plasmodium falciparum, Antimicrob Ag Chemother 40, 2094-2098.
Rabsch W. 1998 Characterization of the catecholate indicator Strain S. Typhimurium TA 2700 as an ent fhuC double mutant. FEMS Microbiol Lett 163, 79-84.
Reissbrodt R, Heinisch L, Möllmann U, Rabsch W, Ulbricht H. 1993 Growth promotion of synthetic catecholate derivatives on Gram-negative bacteria. BioMetals 6, 155-162.
Rodgers SJ, Lee C, Ng CY, Raymond KN. 1987 Ferric Ion Sequestering Agents. 15. Synthesis, Solution Chemistry and Electrochemistry of a New Cationic Analogue of Enterobactin. Inorg. Chem. 26, 1622-1625.
Schumann G, Möllmann U, Heinemann I. 1998 Mutants of Mycobacterium species and their use for screening of antibiotic vectors Patent application DE 19817021.9. (17.4.1998).
Schumann G, Möllmann U. 2001 Screening system for Xenosiderophores as Potential Drug Delivery Agents in Mycobacteria. Antimicrob Ag Chemother 45, 1317-1322.
Schwyn B, Neilands JB. 1987 Universal chemical assay for the detection and determination of siderophores. Anal Biochem 160, 47-56.
Shanzer A, Libman J. 1996 From Biomimetic Ion Carriers to Helical Structures. Croatica Chemica Acta 69, 709-729.
Tor Y, Libman J, Shanzer A, Felder CE, Lifson S. 1992 Tripodal Peptides with Chiral Conformations Stabilized by Interstrand Hydrogen Bonds. J Amer Chem Soc 114, 6653-6661.
Weitl FL, Raymond KN. 1981 Lipophilic Enterobactin Analogues. Terminally N-Alkylated Spermine/Spermidine Catecholcarboxamides. J Org Chem 46, 5234-5237.
Weitl FL, Harris WR, Raymond KN. 1979 Sulfonated Catecholamide Analogues of Enterobactin as Iron Sequestering Agents. J Med Chem 22, 1281-1283.
Wittmann S, Heinisch L, Scherlitz-Hofmann I, Möllmann U, Ankel-Fuchs D. 2000 8-Acyloxy-1,3-benzoxazine-2,4-diones as siderophore components of antibiotics. Arzneim-Forsch/Drug Res. 50, 752-757.
Yamamoto S, Okujo N, Fujita Y, Saito M, Yoshida T, Shinoda S. 1993 Structures of Two Polyamine-Containing Catecholate Siderophores from Vibrio fluvialis. J Biochem 113, 538-544.
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Heinisch, L., Gebhardt, P., Heidersbach, R. et al. New synthetic catecholate-type siderophores with triamine backbone. Biometals 15, 133–144 (2002). https://doi.org/10.1023/A:1015293900133
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DOI: https://doi.org/10.1023/A:1015293900133