title: Free radical scavenging and antiproliferative properties of Biginelli adducts.
abstract: A series of Biginelli adducts bearing different substituents at C-4 position were synthesized by using p-sulfonic acid calix[4]arene as a catalyst. The in vitro potential to scavenge reactive nitrogen/oxygen species (RNS and ROS) and the ability to inhibit cancer cells growth were then investigated. Four adducts were found to be potent scavengers of 2,2-diphenyl-1-picrylhydrazyl (RNS) and/or superoxide anion (ROS) radicals. The antiproliferative activity against cancer cells was disclosed for the first time for 16 monastrol analogs. The capacity of all compounds to inhibit cancer cells growth was dependent on the histological origin of cells, except for BA24, which was highly active against all cell lines. BA20 and BA33 were as potent as the reference drug doxorubicin against adriamycin-resistant ovarian and prostate cancer cells, respectively. These results highlight some monastrol analogs as lead compounds for the design of new free radical scavengers and anticancer agents.
authors.affiliation: Grupo de Estudos em Química Orgânica e Biológica, Departamento de Química, ICEx, Universidade Federal de Minas Gerais, Belo Horizonte, MG, Brazil.
authors.forename: Daniel L
authors.initials: DL
authors.lastname: da Silva
authors.forename: Fabiano S
authors.initials: FS
authors.lastname: Reis
authors.forename: Dandara R
authors.initials: DR
authors.lastname: Muniz
authors.forename: Ana Lúcia T G
authors.initials: AL
authors.lastname: Ruiz
authors.forename: João E
authors.initials: JE
authors.lastname: de Carvalho
authors.forename: Adão A
authors.initials: AA
authors.lastname: Sabino
authors.forename: Luzia V
authors.initials: LV
authors.lastname: Modolo
authors.forename: Angelo
authors.initials: A
authors.lastname: de Fátima
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001713:Biphenyl Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D016166:Free Radical Scavengers / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D015394:Molecular Structure; D010851:Picrates / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D000970:Antineoplastic Agents; D001713:Biphenyl Compounds; D016166:Free Radical Scavengers; D010851:Picrates; C004931:1,1-diphenyl-2-picrylhydrazyl