title: Multimilligram enantioresolution of low-solubility xanthonolignoids on polysaccharide chiral stationary phases using a solid-phase injection system.
abstract: Kielcorins are xanthonolignoids with protein kinase C inhibition and antitumor activities. Four racemates were enantioresolved at a multimilligram scale on tris-3,5-dimethylphenylcarbamate amylose phase using polar organic conditions as mobile phase. The low-solubility of these compounds conditioned the injection amount and consequently the productivity. A solid-phase injection system was developed to increase the production rate of the semipreparative process. The effects of the racemates and the related enantiomers on the in vitro growth of human breast cancer cell line MCF-7 were compared. Differences in their growth inhibitory activity were observed.
authors.affiliation: CEQOFFUP, Laboratório de Química Orgânica, Faculdade Farmácia, Rua Aníbal Cunha 164, 4050-047 Porto, Portugal.
authors.forename: Maria Emília
authors.initials: ME
authors.lastname: Sousa
authors.forename: Maria Elizabeth
authors.initials: ME
authors.lastname: Tiritan
authors.forename: Kátia Roberta Anacleto
authors.initials: KR
authors.lastname: Belaz
authors.forename: Madalena
authors.initials: M
authors.lastname: Pedro
authors.forename: Maria São José
authors.initials: MS
authors.lastname: Nascimento
authors.forename: Quezia Bezerra
authors.initials: QB
authors.lastname: Cass
authors.forename: Madalena Maria Magalhães
authors.initials: MM
authors.lastname: Pinto
mesh_terms: D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D019075:Electrophoresis, Capillary / Q000379:methods*; D004852:Epoxy Compounds / Q000737:chemistry; D006801:Humans; D008689:Methacrylates / Q000737:chemistry; D015394:Molecular Structure; D010647:Phenyl Ethers / Q000737:chemistry; D011134:Polysaccharides / Q000737:chemistry*; D015203:Reproducibility of Results; D012995:Solubility; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014966:Xanthenes / Q000737:chemistry* / Q000494:pharmacology
chemical_list: D004852:Epoxy Compounds; D008689:Methacrylates; D010647:Phenyl Ethers; D011134:Polysaccharides; D014966:Xanthenes; C004919:ethylene dimethacrylate; C007870:glycidyl methacrylate