3′-O- and 5′-O-Propargyl Derivatives of 5-Fluoro-2′-Deoxyuridine: Synthesis, Cytotoxic Evaluation and Conformational Analysis

被引：7
作者：
Baraniak, Dagmara [1 ]
Baranowski, Daniel [1 ]
Ruszkowski, Piotr [2 ]
Boryski, Jerzy [1 ]
机构：
[1] Polish Acad Sci, Inst Bioorgan Chem, Noskowskiego St 12-14, PL-61704 Poznan, Poland
[2] Poznan Univ Med Sci, Fac Pharm, Dept Pharmacol, Rokietnicka St 5a, Poznan, Poland
来源：
NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS | 2016年 / 35卷 / 04期
关键词：
Propargylated 5-fluoro-2 '-deoxyuridine derivatives; propargy moiety; click chemistry reagents; cytotoxic activity; human cancer cell lines: HeLa; KB and MCF-7; CLICK CHEMISTRY APPROACH; MODIFIED NUCLEOSIDES; COUPLING-CONSTANTS; TERMINAL ALKYNES; GRAPHICAL-METHOD; 5-FLUOROURACIL; CAPECITABINE; SPECTROSCOPY; AZIDES; AGENT;
D O I：
10.1080/15257770.2015.1122199
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
A series of new 3 '-O- and 5 '-O-propargyl derivatives of 5-fluoro-2 '-deoxyuridine (1-4) was synthesized by means of propargyl reaction of properly blocked nucleosides (2,4), followed by the deprotection reaction with ammonium fluoride. The synthesized propargylated 5-fluoro-2 '-deoxyuridine analogues (1-4) were evaluated for their cytotoxic activity in three human cancer cell lines: cervical (HeLa), oral (KB) and breast (MCF-7), using the sulforhodamine B (SRB) assay. The highest activity and the best SI coefficient in all of the investigated cancer cells were displayed by 3 '-O-propargyl-5-fluoro-2 '-deoxyuridine (1), and its activity was higher than that of the parent nucleoside. The other new compounds exhibited moderate activity in all of the used cell lines.
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页码：178 / 194
页数：17
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