title: Synthesis, characterization, anti-inflammatory and anti-proliferative activity against MCF-7 cells of O-alkyl and O-acyl flavonoid derivatives.
abstract: A series of O-alkyl and O-acyl flavonoid derivatives was synthesized in high efficiency. Alkylation and acylation of 5-hydroxyflavonoids showed that the low reactivity hydroxyl group, 5-OH, well reacted with strong reagents whereas with weaker reagents, the different products were obtained dependently on structural characteristic of ring C of respective flavonoid. In order to evaluate anti-inflammatory activity, all compounds were tested for in vitro inhibition of bovine serum albumin denaturation and in vivo inhibition of carrageenan-induced mouse paw edema. Among them, the compounds 3, 3b, 4b and 4c demonstrated more effective anti-inflammatory activity than standard drugs (diclofenac sodium and ketoprofen) in both tests. Meanwhile, the flavonoids 2, 2c, 3a and 4b displayed anti-proliferative activity against MCF-7 cell lines. Triacetyl derivative of hesperetin 4b inducing degradation of DNA in MCF-7 cells was observed.
authors.affiliation: Institute of Chemical Technology, Vietnam Academy of Science and Technology. 1 Mac Dinh Chi Street, District 1, Ho Chi Minh City, Viet Nam. Electronic address: htkdung@ict.vast.vn.
authors.forename: T Kim-Dung
authors.initials: TK
authors.lastname: Hoang
authors.affiliation: Institute of Chemical Technology, Vietnam Academy of Science and Technology. 1 Mac Dinh Chi Street, District 1, Ho Chi Minh City, Viet Nam.
authors.forename: T Kim-Chi
authors.initials: TK
authors.lastname: Huynh
authors.affiliation: Institute of Chemical Technology, Vietnam Academy of Science and Technology. 1 Mac Dinh Chi Street, District 1, Ho Chi Minh City, Viet Nam. Electronic address: danh5463bd@yahoo.com.
authors.forename: Thanh-Danh
authors.initials: TD
authors.lastname: Nguyen
mesh_terms: D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000008:administration & dosage / Q000737:chemistry / Q000494:pharmacology*; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D002351:Carrageenan; D002417:Cattle; D049109:Cell Proliferation / Q000187:drug effects; D002470:Cell Survival / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D004487:Edema / Q000139:chemically induced / Q000188:drug therapy; D005260:Female; D005419:Flavonoids / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D061986:MCF-7 Cells; D008297:Male; D051379:Mice; D015394:Molecular Structure; D012710:Serum Albumin, Bovine / Q000187:drug effects; D013329:Structure-Activity Relationship
chemical_list: D000894:Anti-Inflammatory Agents, Non-Steroidal; D000970:Antineoplastic Agents; D005419:Flavonoids; D012710:Serum Albumin, Bovine; D002351:Carrageenan
keywords: Anti-inflammatory; Anti-proliferative; Flavonoid; MCF-7; Synthesis