Synthesis and biological assay of new 2'-deoxyuridine dimers containing a 1, 2, 3-triazole linker. Part I. (4th March 2019)

• Record Type: Journal Article
• Authors: Michalska, Lucyna; Wawrzyniak, Dariusz; Szymańska-Michalak, Agnieszka; Barciszewski, Jan; Boryski, Jerzy; Baraniak, Dagmara
• Is Part Of: Nucleosides, nucleotides & nucleic acids. Volume 38:Number 3(2019)
• Page Start: 218
• Page End: 235
• Publication Date: 2019-03-04
• Subjects: 2'-deoxyuridine -- floxuridine -- nucleoside dimers derivatives -- heterodinucleotides -- click chemistry -- 1, 3-dipolar cycloaddition -- 1, 2, 3-triazoles -- cancer theraphy -- cytotoxic activity -- human cancer cell lines; Nucleosides -- Periodicals; Nucleotides -- Periodicals; Nucleic acids -- Periodicals; 572.8
• DOI: 10.1080/15257770.2018.1514122
• Languages: English
• ISSNs: 1525-7770

Abstract

Abstract: We describe a simple method for the synthesis of modified dinucleosides containing pyrimidine nucleoside analogues (2'-deoxyuridine, thymidine and 5-fluoro-2'-deoxyuridine). Six different dimers with a 1, 2, 3-triazole linkage were obtained by azide–alkyne 1, 3-dipolar cycloaddition (click reaction), starting from propargylated 2'-deoxyuridine and 5'-azido-nucleoside derivatives. Their cytotoxic activity was tested in five human cancer cell lines: cervical (HeLa), high grade gliomas (U-118 MG, U-87 MG, T98G), liver (HepG2), and normal human fibroblast cell line (MRC-5) using the sulforhodamine B (SRB) assay. The experiment showed that the obtained dimers with a 1, 2, 3-triazole moiety were very stable compounds, also in the physiological-like media, and had no anticancer activity.