title: Hybrid compounds with two redox centres: modular synthesis of chalcogen-containing lapachones and studies on their antitumor activity.
abstract: Chalcogen-containing β-lapachone derivatives were synthesized using a straightforward methodology and evaluated against several cancer cell lines (leukaemia, human colon carcinoma, prostate, human metastatic prostate, ovarian, central nervous system and breast), showing, in some cases, IC50 values below 1 μM. The cytotoxic potential of the lapachones evaluated was also assayed using non-tumor cells: human peripheral blood mononuclear cells, two murine fibroblast lines (L929 and V79 cells) and MDCK (canine kidney epithelial cells). These compounds could provide promising new lead derivatives for anticancer drug development. This manuscript reports important findings since few authors have described C-3 substituted β-lapachone with potent antitumor activity. The methodology employed allowed the preparation of the compounds from lapachol within a few minutes in a green approach.
authors.affiliation: Departamento de Química, UFSC, 88040-900, Florianópolis, SC, Brazil; Instituto de Química, Departamento de Química Orgânica, UFBA, 40170-290, Salvador, BA, Brazil.
authors.forename: André A
authors.initials: AA
authors.lastname: Vieira
authors.affiliation: Departamento de Química, UFSC, 88040-900, Florianópolis, SC, Brazil.
authors.forename: Igor R
authors.initials: IR
authors.lastname: Brandão
authors.affiliation: Instituto de Ciências Exatas, Departamento de Química, UFMG, 31270-901, Belo Horizonte, MG, Brazil.
authors.forename: Wagner O
authors.initials: WO
authors.lastname: Valença
authors.affiliation: Departamento de Física e Informática, Instituto de Física, USP, 13560-160, São Carlos, SP, Brazil.
authors.forename: Carlos A
authors.initials: CA
authors.lastname: de Simone
authors.affiliation: Departamento de Fisiologia e Farmacologia, UFC, 60430-270, Fortaleza, CE, Brazil.
authors.forename: Bruno C
authors.initials: BC
authors.lastname: Cavalcanti
authors.affiliation: Departamento de Fisiologia e Farmacologia, UFC, 60430-270, Fortaleza, CE, Brazil; Fiocruz - Ceará, 60180-900, Fortaleza, CE, Brazil.
authors.forename: Claudia
authors.initials: C
authors.lastname: Pessoa
authors.affiliation: Departamento de Fisiologia e Farmacologia, UFC, 60430-270, Fortaleza, CE, Brazil.
authors.forename: Teiliane R
authors.initials: TR
authors.lastname: Carneiro
authors.affiliation: Departamento de Química, UFSC, 88040-900, Florianópolis, SC, Brazil. Electronic address: braga.antonio@ufsc.br.
authors.forename: Antonio L
authors.initials: AL
authors.lastname: Braga
authors.affiliation: Instituto de Ciências Exatas, Departamento de Química, UFMG, 31270-901, Belo Horizonte, MG, Brazil. Electronic address: eufranio@ufmg.br.
authors.forename: Eufrânio N
authors.initials: EN
authors.lastname: da Silva
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002460:Cell Line; D049109:Cell Proliferation / Q000187:drug effects; D018011:Chalcogens / Q000737:chemistry*; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D051379:Mice; D008958:Models, Molecular; D015394:Molecular Structure; D009285:Naphthoquinones / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D010084:Oxidation-Reduction; D013329:Structure-Activity Relationship
chemical_list: D000970:Antineoplastic Agents; D018011:Chalcogens; D009285:Naphthoquinones; C014638:beta-lapachone
keywords: Anticancer; Antitumor; Quinone; Selenide; Selenium; Sulfur; β-lapachone