title: Analysis of guazatine mixture by LC and LC-MS and antimycotic activity determination of principal components.
abstract: Guazatine is a non-systemic contact fungicide, a mixture of reaction products from polyamines, comprising mainly octa-methylenediamine, iminodi(octamethylene)diamine, octamethylenebis(imino-octamethylene) diamine and carbamonitrile. In this work, the analysis of guazatine mixture by LC and LC-MS has been treated for the first time. In the guazatine mixture diamine derivatives account for 40% of the constituents of guazatine, triamines for 46%, tetramines for 11% and other amine derivatives for 3%. The most abundant individual components are the fully guanidated triamine (GGG, 30.6%) and the fully guanidated diamine (GG, 29.5%) followed by the monoguanidated diamine (GN, 9.8%) and a diguanidated triamine (GGN, 8.1%). The identification and separation of main components of commercial guazatine was performed through a new LC-MS method. The separation was performed on an Alltima C(18) column using linear gradient elution (formic acid in water and acetonitrile) with UV-detection at 200 nm and the identification was performed by ESI(+)-mass spectrometry analysis. The main components (GN, GG, GNG, GGN, GGG and GGGG) were then purified and separated from the mixture. Antimycotic activity of guazatine derivatives was determined on different species and strains belonging to genus Candida. The results obtained suggest that GNG and GGGG components can further be developed in new antifungal compounds with high potential for the treatment of Candida infections.
authors.affiliation: Dipartimento Farmaco Chimico Tecnologico, Università degli Studi di Siena, via A. Moro 2, Siena I-53100, Italy. dreassi@unisi.it
authors.forename: Elena
authors.initials: E
authors.lastname: Dreassi
authors.forename: Alessandra Tania
authors.initials: AT
authors.lastname: Zizzari
authors.forename: Silvia
authors.initials: S
authors.lastname: D'Arezzo
authors.forename: Paolo
authors.initials: P
authors.lastname: Visca
authors.forename: Maurizio
authors.initials: M
authors.lastname: Botta
mesh_terms: D000935:Antifungal Agents / Q000494:pharmacology*; D002175:Candida / Q000187:drug effects* / Q000235:genetics; D002853:Chromatography, Liquid / Q000295:instrumentation / Q000379:methods*; D045424:Complex Mixtures / Q000032:analysis / Q000737:chemistry; D006146:Guanidines / Q000032:analysis* / Q000737:chemistry; D013058:Mass Spectrometry / Q000379:methods*; D008826:Microbial Sensitivity Tests; D011073:Polyamines / Q000032:analysis / Q000737:chemistry / Q000302:isolation & purification; D013056:Spectrophotometry, Ultraviolet
chemical_list: D000935:Antifungal Agents; D045424:Complex Mixtures; D006146:Guanidines; D011073:Polyamines; C012343:guazatine