title: Evaluation of toxicity on epithelial and tumor cells of biaryl dipeptide tyrosines.
abstract: We report a method to obtain biaryl dipeptide tyrosine via Suzuki-Miyaura and alkynyl dipeptide tyrosine by Sonogashira cross-coupling reactions. Analysis of the biological action of biaryl dipeptide tyrosine 4d compound showed its ability to impair the metabolism and proliferation of SK-Mel-28 human melanoma lineage cells, independently of mitochondrial membrane depolarization, apoptosis and necrosis. Moreover, 4d compound did not cause toxicity to human umbilical vein endothelial cells (HUVEC), suggesting its toxic specificity to cancer cells.
authors.affiliation: Departamento de Farmácia, Faculdade de Ciências Farmacêuticas, Universidade de São Paulo, São Paulo, SP, Brazil.
authors.forename: Stanley N S
authors.initials: SN
authors.lastname: Vasconcelos
authors.affiliation: Departamento de Análises Clínicas e Toxicológicas, Faculdade de Ciências Farmacêuticas, Universidade de São Paulo, São Paulo, SP, Brazil.
authors.forename: Carine C
authors.initials: CC
authors.lastname: Drewes
authors.affiliation: Departamento de Análises Clínicas e Toxicológicas, Faculdade de Ciências Farmacêuticas, Universidade de São Paulo, São Paulo, SP, Brazil.
authors.forename: Leonard
authors.initials: L
authors.lastname: de Vinci Kanda Kupa
authors.affiliation: Departamento de Análises Clínicas e Toxicológicas, Faculdade de Ciências Farmacêuticas, Universidade de São Paulo, São Paulo, SP, Brazil.
authors.forename: Sandra H P
authors.initials: SH
authors.lastname: Farsky
authors.affiliation: Departamento de Farmácia, Faculdade de Ciências Farmacêuticas, Universidade de São Paulo, São Paulo, SP, Brazil. Electronic address: hstefani@usp.br.
authors.forename: Hélio A
authors.initials: HA
authors.lastname: Stefani
mesh_terms: D016923:Cell Death / Q000187:drug effects; D049109:Cell Proliferation / Q000187:drug effects; D002478:Cells, Cultured; D004151:Dipeptides / Q000138:chemical synthesis / Q000737:chemistry / Q000633:toxicity*; D004305:Dose-Response Relationship, Drug; D061307:Human Umbilical Vein Endothelial Cells / Q000166:cytology* / Q000378:metabolism; D006801:Humans; D015394:Molecular Structure; D009369:Neoplasms / Q000378:metabolism / Q000473:pathology*; D013329:Structure-Activity Relationship; D014443:Tyrosine / Q000138:chemical synthesis / Q000737:chemistry / Q000633:toxicity*
chemical_list: D004151:Dipeptides; D014443:Tyrosine
keywords: Alkyne; Dipeptide; Melanoma; Tumor; Tyrosine