title: Ferrocenylselenoamides: synthesis, characterization and cytotoxic properties.
abstract: A new series of ferrocenyl selenoamides 7-11 (FcSeNH(CH(2))(n)CH(2)(R)OH, n = 1, 2, 3, R = H, Me, Ph) were prepared in good yields by selenative demetalation of Fischer aminocarbene complexes. The crystal structures of 7 [FcSeNH(CH(2))(2)OH] and 19 [PhSeNH(CH(2))(2)OH] reveal their capability to form intermolecular hydrogen bonding in solid state. Results of SRB assays show that these new selenium compounds have a good anticancer potency superior to tamoxifen and cisplatin, with IC(50) values ranging from 4.5 to 13.32 μM against human breast cancer cell lines. A preliminary model to explain the structure-cytotoxic activity relation is proposed where different structural parameters such as the alkyl chain length, the presence of bulky groups in the same chain, the effect of hydroxyl group, and also the role of ferrocene moiety are included as being responsible for the cytotoxic response.
authors.affiliation: Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, Coyoacán, C.P. 04360 México D.F., México.
authors.forename: Alejandro I
authors.initials: AI
authors.lastname: Gutiérrez-Hernández
authors.forename: José G
authors.initials: JG
authors.lastname: López-Cortés
authors.forename: M Carmen
authors.initials: MC
authors.lastname: Ortega-Alfaro
authors.forename: M Teresa
authors.initials: MT
authors.lastname: Ramírez-Apan
authors.forename: José de Jesús
authors.initials: Jde J
authors.lastname: Cázares-Marinero
authors.forename: Rubén A
authors.initials: RA
authors.lastname: Toscano
mesh_terms: D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D045744:Cell Line, Tumor; D056831:Coordination Complexes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D018360:Crystallography, X-Ray; D004354:Drug Screening Assays, Antitumor; D005296:Ferrous Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006801:Humans; D020128:Inhibitory Concentration 50; D000075163:Metallocenes; D016566:Organoselenium Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013329:Structure-Activity Relationship
chemical_list: D000577:Amides; D000970:Antineoplastic Agents; D056831:Coordination Complexes; D005296:Ferrous Compounds; D000075163:Metallocenes; D016566:Organoselenium Compounds; C004998:ferrocene