title: Synthesis, cytotoxic and antioxidant evaluations of amino derivatives from perezone.
abstract: A series of eight amino derivatives (3a-h) from perezone 1 were prepared by nucleophilic addition of bioactive amines v.gr. melatonin, acetyl tryptamine, tryptophan and other amino acids esters (valine, leucine and methionine). Their structures were elucidated by spectroscopy data. The cytotoxic evaluation against four human tumor cell lines PC-3, K-562, HCT-15 and SKLU-1 was performed as well as the TBARS assay for antioxidant activity. The results suggest that 1 and its isomer 4 were highly active against all cell lines, 4 was twice as potent than 1 against PC-3 and HCT-15. The derivative 3a (IC(50)=7.5 ± 0.3 μM) was more active than 1 against HCT-15 whereas 3h was selective against K-562 with IC(50)=4.5 ± 0.4 μM. The TBARS assay has shown that 3c with IC(50)=5.564 ± 0.24 μM is a potent antioxidant with superior effect comparing to α-tocopherol and moreover was more active than the precursor molecule 1.
authors.affiliation: Departamento de Sistemas Biológicos, UAM-Xochimilco, Calzada del Hueso 1100, Col. Villa Quietud, Coyoacán, DF, 04960, Mexico. mclozada@correo.xoc.uam.mx
authors.forename: M
authors.initials: M
authors.lastname: Concepción Lozada
authors.forename: Olivia
authors.initials: O
authors.lastname: Soria-Arteche
authors.forename: Ma Teresa
authors.initials: MT
authors.lastname: Ramírez Apan
authors.forename: Antonio
authors.initials: A
authors.lastname: Nieto-Camacho
authors.forename: Raúl G
authors.initials: RG
authors.lastname: Enríquez
authors.forename: Teresa
authors.initials: T
authors.lastname: Izquierdo
authors.forename: Arturo
authors.initials: A
authors.lastname: Jiménez-Corona
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000975:Antioxidants / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001921:Brain / Q000187:drug effects / Q000378:metabolism; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D002470:Cell Survival / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D015227:Lipid Peroxidation / Q000187:drug effects; D008297:Male; D051381:Rats; D017208:Rats, Wistar; D012717:Sesquiterpenes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D000970:Antineoplastic Agents; D000975:Antioxidants; D012717:Sesquiterpenes; C053752:perezone