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New insight into nucleo α-amino acids - Synthesis and SAR studies on cytotoxic activity of ß-pyrimidine alanines.
Ignatowska, Jolanta; Mironiuk-Puchalska, Ewa; Grzeskowiak, Piotr; Winska, Patrycja; Wielechowska, Monika; Bretner, Maria; Karatsai, Olena; Redowicz, Maria Jolanta; Koszytkowska-Stawinska, Mariola.
Afiliação
  • Ignatowska J; Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664 Warsaw, Poland.
  • Mironiuk-Puchalska E; Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664 Warsaw, Poland.
  • Grzeskowiak P; Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664 Warsaw, Poland.
  • Winska P; Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664 Warsaw, Poland.
  • Wielechowska M; Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664 Warsaw, Poland.
  • Bretner M; Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664 Warsaw, Poland.
  • Karatsai O; Laboratory of Molecular Basis of Cell Motility, Nencki Institute of Experimental Biology, 3 Pasteur St., 02-093 Warsaw, Poland.
  • Redowicz MJ; Laboratory of Molecular Basis of Cell Motility, Nencki Institute of Experimental Biology, 3 Pasteur St., 02-093 Warsaw, Poland.
  • Koszytkowska-Stawinska M; Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664 Warsaw, Poland. Electronic address: mkoszyt@ch.pw.edu.pl.
Bioorg Chem ; 100: 103864, 2020 07.
Article em En | MEDLINE | ID: mdl-32446118
Three series of the ß-pyrimidine alanines, including willardiine - a naturally occurring amino acid, were prepared from the l-serine-derived sulfamidates. Compounds 3b, 4a and 4b demonstrated antiproliferative activity toward the studied cancer cell lines, albeit the effect of these compounds on human brain astrocytoma MOG-G-CCM cells was more significant than on human neuroblastoma SK-N-AS cells. The cytosine analog of willardiine, compound 4b, reduced viability of MOG-G-CCM cells with EC50 = 36 ± 2 µM, more effectively than AMPA antagonist GYKI 52466. Willardiine showed possible capability of affecting invasiveness of glioblastoma U251 MG cells with no effect on their viability and morphology. Compound 3d, the ethyl ester of willardiine, featured activity toward binding domain hHS1S2I of the GluR2 receptor. Docking analysis revealed that the location mode of compound 3d at the S1S2 domain of hGluR2 (PDB ID: 3R7X) might differ from that of willardiine.
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Pirimidinas / Beta-Alanina / Antineoplásicos Limite: Humans Idioma: En Revista: Bioorg Chem Ano de publicação: 2020 Tipo de documento: Article País de afiliação: Polônia

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Pirimidinas / Beta-Alanina / Antineoplásicos Limite: Humans Idioma: En Revista: Bioorg Chem Ano de publicação: 2020 Tipo de documento: Article País de afiliação: Polônia