title: Synthesis and biological activities of novel dexibuprofen tetraacetylriboflavin conjugates.
abstract: A series of novel dexibuprofen derivatives covalently linked via alkylene spacers of variable length to tetraacetylated riboflavin have been developed. The target compounds became accessible by reaction of the chloromethyl ester of dexibuprofen with tetraacetylriboflavin (compound 7) or by synthesis of the appropriate N3-(omega-iodoalkyl)-2',3',4',5'-Tetraacetylriboflavin followed by treatment with dexibuprofen (derivatives 8-11), respectively. Biological screening revealed that the target compounds exhibit antiproliferative effects on MCF-7 breast cancer and HT-29 colon carcinoma cells with IC50 values in the range of 8-15 microM. Enzymatic studies on human platelets indicated significant COX-1 inhibitory activities of the target compounds.
authors.affiliation: Institute of Pharmacy, Leopold-Franzens University of Innsbruck, Innrain 52a, 6020 Innsbruck, Austria.
authors.forename: Christian
authors.initials: C
authors.lastname: Banekovich
authors.forename: Ingo
authors.initials: I
authors.lastname: Ott
authors.forename: Thao
authors.initials: T
authors.lastname: Koch
authors.forename: Barbara
authors.initials: B
authors.lastname: Matuszczak
authors.forename: Ronald
authors.initials: R
authors.lastname: Gust
mesh_terms: D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D001792:Blood Platelets / Q000187:drug effects / Q000201:enzymology; D001943:Breast Neoplasms / Q000188:drug therapy; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D051545:Cyclooxygenase 1 / Q000378:metabolism; D016861:Cyclooxygenase Inhibitors / Q000138:chemical synthesis / Q000494:pharmacology; D005260:Female; D019073:HT29 Cells; D006801:Humans; D007052:Ibuprofen / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000494:pharmacology; D066298:In Vitro Techniques; D016859:Lipoxygenase Inhibitors / Q000138:chemical synthesis / Q000494:pharmacology; D012256:Riboflavin / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000494:pharmacology
chemical_list: D000894:Anti-Inflammatory Agents, Non-Steroidal; D000970:Antineoplastic Agents; D016861:Cyclooxygenase Inhibitors; D016859:Lipoxygenase Inhibitors; D051545:Cyclooxygenase 1; D012256:Riboflavin; D007052:Ibuprofen