title: Correlations between chromatographic parameters and bioactivity predictors of potential herbicides.
abstract: Different liquid chromatography techniques, including reversed-phase liquid chromatography on Purosphere RP-18e, IAM.PC.DD2 and Cosmosil Cholester columns and micellar liqud chromatography with a Purosphere RP-8e column and using buffered sodium dodecyl sulfate-acetonitrile as the mobile phase, were applied to study the lipophilic properties of 15 newly synthesized phenoxyacetic and carbamic acid derivatives, which are potential herbicides. Chromatographic lipophilicity descriptors were used to extrapolate log k parameters (log kw and log km) and log k values. Partitioning lipophilicity descriptors, i.e., log P coefficients in an n-octanol-water system, were computed from the molecular structures of the tested compounds. Bioactivity descriptors, including partition coefficients in a water-plant cuticle system and water-human serum albumin and coefficients for human skin partition and permeation were calculated in silico by ACD/ADME software using the linear solvation energy relationship of Abraham. Principal component analysis was applied to describe similarities between various chromatographic and partitioning lipophilicities. Highly significant, predictive linear relationships were found between chromatographic parameters and bioactivity descriptors.
authors.affiliation: Maria Curie-Skłodowska University, Department of Physical Chemistry, Faculty of Chemistry, Maria Curie-Skłodowska Sq. 3, 20-031 Lublin, Poland malgorzata.janicka@poczta.umcs.lublin.pl.
authors.forename: Małgorzata
authors.initials: M
authors.lastname: Janicka
mesh_terms: D000085:Acetates / Q000032:analysis / Q000737:chemistry / Q000493:pharmacokinetics; D002219:Carbamates / Q000032:analysis / Q000737:chemistry / Q000493:pharmacokinetics; D002853:Chromatography, Liquid / Q000295:instrumentation / Q000379:methods*; D003198:Computer Simulation; D006540:Herbicides / Q000032:analysis* / Q000737:chemistry / Q000493:pharmacokinetics*; D006801:Humans; D057927:Hydrophobic and Hydrophilic Interactions; D016014:Linear Models; D008954:Models, Biological; D008958:Models, Molecular; D010944:Plants; D025341:Principal Component Analysis; D012709:Serum Albumin; D012869:Skin Absorption
chemical_list: D000085:Acetates; D002219:Carbamates; D006540:Herbicides; D012709:Serum Albumin; C070766:carbamic acid; C415326:phenoxyacetic acid