TY - JOUR
T1 - Synthesis of ribavirin 1,2,3- and 1,2,4-triazolyl analogs with changes at the amide and cytotoxicity in breast cancer cell lines
AU - Way, Hannah
AU - Roh, Joshua
AU - Venteicher, Brooklynn
AU - Chandra, Surabhi
AU - Thomas, Allen A.
N1 - Funding Information:
H.W. thanks the UNK Summer Student Research Program (SSRP) for financial support. This work was also supported by the UNK Research Services Council (RSC) and the Nebraska EPSCoR Undergraduate Research Experiences (URE) at Small Colleges and Universities Program. Funding for S.C. and the tissue culture lab used for cell survival experiments was provided by the Nebraska IDeA Networks of Biomedical Research Excellence (INBRE) program.
Publisher Copyright:
© 2022 Taylor & Francis Group, LLC.
PY - 2023
Y1 - 2023
N2 - We report the synthesis and cytotoxicity in MCF-7 and MDA-MB-231 breast cancer cells of novel 1,2,3- and 1,2,4-triazolyl analogs of ribavirin. We modified ribavirin’s carboxamide moiety to test the effects of lipophilic groups. 1-β-D-Ribofuranosyl-1H-1,2,3-triazoles were prepared using Click Chemistry, whereas an unprecedented application of a prior 1,2,4-triazole ring synthesis was used for 1-β-D-ribofuranosyl-1H-1,2,4-triazole analogs. Though cytotoxicity was mediocre and there was no correlation with lipophilicity, we discovered that a structurally similar concentrative nucleoside transporter 2 (CNT2) inhibitor was modestly cytotoxic (MCF-7 IC50 of 42 µM). These syntheses could be used to efficiently investigate variation in the nucleobase.
AB - We report the synthesis and cytotoxicity in MCF-7 and MDA-MB-231 breast cancer cells of novel 1,2,3- and 1,2,4-triazolyl analogs of ribavirin. We modified ribavirin’s carboxamide moiety to test the effects of lipophilic groups. 1-β-D-Ribofuranosyl-1H-1,2,3-triazoles were prepared using Click Chemistry, whereas an unprecedented application of a prior 1,2,4-triazole ring synthesis was used for 1-β-D-ribofuranosyl-1H-1,2,4-triazole analogs. Though cytotoxicity was mediocre and there was no correlation with lipophilicity, we discovered that a structurally similar concentrative nucleoside transporter 2 (CNT2) inhibitor was modestly cytotoxic (MCF-7 IC50 of 42 µM). These syntheses could be used to efficiently investigate variation in the nucleobase.
KW - Nucleoside analogs
KW - click chemistry
KW - initiation factor
KW - triazole
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U2 - 10.1080/15257770.2022.2107218
DO - 10.1080/15257770.2022.2107218
M3 - Article
C2 - 35929908
AN - SCOPUS:85135437991
SN - 1525-7770
VL - 42
SP - 38
EP - 64
JO - Nucleosides, Nucleotides and Nucleic Acids
JF - Nucleosides, Nucleotides and Nucleic Acids
IS - 1
ER -