Multimilligram enantioresolution of low-solubility xanthonolignoids on polysaccharide chiral stationary phases using a solid-phase injection system.
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.
Sousa
Maria Emília
ME
CEQOFFUP, Laboratório de Química Orgânica, Faculdade Farmácia, Rua Aníbal Cunha 164, 4050-047 Porto, Portugal.
Tiritan
Maria Elizabeth
ME
Belaz
Kátia Roberta Anacleto
KR
Pedro
Madalena
M
Nascimento
Maria São José
MS
Cass
Quezia Bezerra
QB
Pinto
Madalena Maria Magalhães
MM
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
D004852:Epoxy Compounds; D008689:Methacrylates; D010647:Phenyl Ethers; D011134:Polysaccharides; D014966:Xanthenes; C004919:ethylene dimethacrylate; C007870:glycidyl methacrylate