title: The Fe(III) and Ga(III) coordination chemistry of 3-(1-hydroxymethylidene) and 3-(1-hydroxydecylidene)-5-(2-hydroxyethyl)pyrrolidine-2,4-dione: novel tetramic acid degradation products of homoserine lactone bacterial quorum sensing molecules.
abstract: Bacteria use small diffusible molecules to exchange information in a process called quorum sensing (QS). An important class of quorum sensing molecules used by Gram-negative bacteria is the family of N-acylhomoserine lactones (HSL). It was recently discovered that a degradation product of the QS molecule 3-oxo-C(12)-homoserine lactone, the tetramic acid 3-(1-hydroxydecylidene)-5-(2-hydroxyethyl)pyrrolidine-2,4-dione, is a potent antibacterial agent, thus implying roles for QS outside of simply communication. Because these tetramic acids also appear to bind iron with appreciable affinity it was suggested that metal binding might contribute to their biological activity. Here, using a variety of spectroscopic tools, we describe the coordination chemistry of both the methylidene and decylidene tetramic acid derivatives with Fe(III) and Ga(III) and discuss the potential biological significance of such metal binding.
authors.affiliation: Department of Chemistry and Biochemistry, San Diego State University, San Diego, CA 92182-1030, USA.
authors.forename: Ariel A
authors.initials: AA
authors.lastname: Romano
authors.forename: Tobias
authors.initials: T
authors.lastname: Hahn
authors.forename: Nicole
authors.initials: N
authors.lastname: Davis
authors.forename: Colin A
authors.initials: CA
authors.lastname: Lowery
authors.forename: Anjali K
authors.initials: AK
authors.lastname: Struss
authors.forename: Kim D
authors.initials: KD
authors.lastname: Janda
authors.forename: Lars H
authors.initials: LH
authors.lastname: Böttger
authors.forename: Berthold F
authors.initials: BF
authors.lastname: Matzanke
authors.forename: Carl J
authors.initials: CJ
authors.lastname: Carrano
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000737:chemistry* / Q000494:pharmacology; D056831:Coordination Complexes / Q000737:chemistry* / Q000494:pharmacology; D004563:Electrochemistry; D005708:Gallium / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D007501:Iron / Q000737:chemistry*; D008826:Microbial Sensitivity Tests; D011550:Pseudomonas aeruginosa / Q000187:drug effects / Q000254:growth & development; D053038:Quorum Sensing; D013211:Staphylococcus aureus / Q000187:drug effects / Q000254:growth & development; D013388:Succinimides / Q000737:chemistry* / Q000494:pharmacology
chemical_list: C572239:3-(1-hydroxydecylidene)-5-(2-hydroxyethyl)pyrrolidine-2,4-dione; D000900:Anti-Bacterial Agents; D056831:Coordination Complexes; D013388:Succinimides; C088386:homoserine lactone; D005708:Gallium; D007501:Iron; D015107:4-Butyrolactone