New synthetic catecholate-type siderophores with triamine backbone.
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.
Heinisch
Lothar
L
Hans Knöll-Institut for Natural Products Research, Jena, Germany. Heinisch@pmail.hki-jena.de
Gebhardt
Peter
P
Heidersbach
Renate
R
Reissbrodt
Rolf
R
Möllmann
Ute
U
D000588:Amines / Q000737:chemistry*; D002396:Catechols / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D002455:Cell Division / Q000187:drug effects; D015394:Molecular Structure; D020613:Morganella morganii / Q000187:drug effects / Q000254:growth & development; D011550:Pseudomonas aeruginosa / Q000187:drug effects / Q000254:growth & development; D017262:Siderophores / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology
D000588:Amines; D002396:Catechols; D017262:Siderophores; C034221:catechol