title: Phenolic acid derivatives with potential anticancer properties--a structure-activity relationship study. Part 1: methyl, propyl and octyl esters of caffeic and gallic acids.
abstract: The antiproliferative and cytotoxic properties of polyphenolic acid derivatives, structurally related with the natural models caffeic and gallic acids, have been tested in human cervix adenocarcinoma cells (HeLa). Simultaneous structural information was obtained for these compounds through theoretical ab initio methods. This study was conducted for the following esters: methyl caffeate (MC, 1), propyl caffeate (PC, 2), octyl caffeate (OC, 3), methyl gallate (MG, 4), propyl gallate (PG, 5) and octyl gallate (OG, 6). A significant growth-inhibition effect was assessed for some of these compounds, clearly dependent on their structural characteristics. Marked structure-activity relationships (SARs)--namely the number of hydroxyl ring substituents--were found to rule the biological effect of such systems.
authors.affiliation: Research Unit Molecular Physical-Chemistry, Coimbra University, Portugal.
authors.forename: S M
authors.initials: SM
authors.lastname: Fiuza
authors.forename: C
authors.initials: C
authors.lastname: Gomes
authors.forename: L J
authors.initials: LJ
authors.lastname: Teixeira
authors.forename: M T
authors.initials: MT
authors.lastname: Girão da Cruz
authors.forename: M N D S
authors.initials: MN
authors.lastname: Cordeiro
authors.forename: N
authors.initials: N
authors.lastname: Milhazes
authors.forename: F
authors.initials: F
authors.lastname: Borges
authors.forename: M P M
authors.initials: MP
authors.lastname: Marques
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D002109:Caffeic Acids / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D002460:Cell Line; D002470:Cell Survival / Q000187:drug effects; D004354:Drug Screening Assays, Antitumor; D004952:Esters / Q000737:chemistry; D005707:Gallic Acid / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D006801:Humans; D062385:Hydroxybenzoates / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D020128:Inhibitory Concentration 50; D008745:Methylation; D015394:Molecular Structure; D013329:Structure-Activity Relationship
chemical_list: D000970:Antineoplastic Agents; D002109:Caffeic Acids; D004952:Esters; D062385:Hydroxybenzoates; D005707:Gallic Acid; C017616:phenolic acid