title: Synthesis and biological evaluation of hydroxyl-substituted Schiff-bases containing ferrocenyl moieties.
abstract: Three new hydroxyl-substituted Schiff-bases containing ferrocenyl moieties were synthesized, and their antioxidant and anticancer activities were evaluated. Among the synthesized hydroxyl-substituted Schiff-bases, compound 1 containing both ferrocenyl and o-dihydroxyl groups exhibits the highest antioxidant and anticancer activities. Flow cytometric analysis showed that compound 1 is capable of disturbing the cancer cell cycle and inducing more cells to be arrested in G2 phase. The excellent biological activities of compound 1 are attributed to the presence of both ferrocenyl and o-dihydroxyl groups. The ferrocenyl moiety has dual functions in compound 1, i.e., increasing the lipophilicity and lowering the redox potentials of o-dihydroxyl groups. In addition, compound 1 could reversibly bind with HSA mainly via a mechanism involving the formation of complexes, in which hydrophobic interaction is the main acting force. Thus, compound 1 containing both ferrocenyl and o-dihydroxyl groups is a potential antioxidant with anticancer activity.
authors.affiliation: College of Chemistry and Chemical Engineering, Central South University, Changsha, Hunan 410083, P. R. China. juanli@csu.edu.cn liuyounian@csu.edu.cn.
authors.forename: Wansong
authors.initials: W
authors.lastname: Chen
authors.forename: Weizhu
authors.initials: W
authors.lastname: Ou
authors.forename: Liqiang
authors.initials: L
authors.lastname: Wang
authors.forename: Yuanqiang
authors.initials: Y
authors.lastname: Hao
authors.forename: Jiashun
authors.initials: J
authors.lastname: Cheng
authors.forename: Juan
authors.initials: J
authors.lastname: Li
authors.forename: You-Nian
authors.initials: YN
authors.lastname: Liu
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D060326:Chemistry Techniques, Synthetic; D004563:Electrochemistry; D005296:Ferrous Compounds / Q000737:chemistry*; D016166:Free Radical Scavengers / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D006367:HeLa Cells; D006461:Hemolysis / Q000187:drug effects; D006801:Humans; D057927:Hydrophobic and Hydrophilic Interactions; D006878:Hydroxides / Q000737:chemistry*; D000075163:Metallocenes; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D012545:Schiff Bases / Q000737:chemistry; D012709:Serum Albumin / Q000378:metabolism
chemical_list: D000970:Antineoplastic Agents; D005296:Ferrous Compounds; D016166:Free Radical Scavengers; D006878:Hydroxides; D000075163:Metallocenes; D009942:Organometallic Compounds; D012545:Schiff Bases; D012709:Serum Albumin; C031356:hydroxide ion; C004998:ferrocene