title: Synthesis, characterization and biological studies of diosgenyl analogues.
abstract: A series of optical amino acid diosgenyl esters and diosgenyl salicylate conjugates were designed and synthesized to develop new anticancer and anti-inflammatory agents. The analogue 9c that contains an 6-aminohexanoic acid residue at C-3 of diosgenin exhibits higher potency against all three tumor cell lines with IC(50) values ranging from 4.7 μM in C26 cells to 14.6 μM in Hep G2 cells. In addition, seven of newly synthesized compounds significantly inhibit xylene-induced ear edema and exhibit comparable or better anti-inflammatory activities than those of diosgenin and aspirin. Furthermore, preliminary structure-activity relationship studies demonstrate that diosgenyl salicylate conjugates have stronger anti-inflammatory activities than amino acid diosgenyl esters.
authors.affiliation: Institute for Nanobiomedical Technology and Membrane Biology, and Laboratory of Ethnopharmacology, Regenerative Medicine Research Center, West China Hospital/West China Medical School, Sichuan University, Chengdu 610041, China.
authors.forename: Baozhan
authors.initials: B
authors.lastname: Huang
authors.forename: Dan
authors.initials: D
authors.lastname: Du
authors.forename: Rui
authors.initials: R
authors.lastname: Zhang
authors.forename: Xiaohua
authors.initials: X
authors.lastname: Wu
authors.forename: Zhihua
authors.initials: Z
authors.lastname: Xing
authors.forename: Yang
authors.initials: Y
authors.lastname: He
authors.forename: Wen
authors.initials: W
authors.lastname: Huang
mesh_terms: D000818:Animals; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D004144:Diosgenin / Q000031:analogs & derivatives / Q000737:chemistry / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D004487:Edema / Q000139:chemically induced / Q000188:drug therapy*; D056945:Hep G2 Cells; D006801:Humans; D015394:Molecular Structure; D051381:Rats; D013329:Structure-Activity Relationship; D014992:Xylenes
chemical_list: D000893:Anti-Inflammatory Agents; D000970:Antineoplastic Agents; D014992:Xylenes; D004144:Diosgenin