Synthesis and biological evaluation of nucleobase-modified analogs of the anticancer compounds 3'-C-ethynyluridine (EUrd) and 3'-C-ethynylcytidine (ECyd)

Patrick J Hrdlicka; Jan S Jepsen; Claus Nielsen; Jesper Wengel; Jan Stenvang

doi:10.1016/j.bmc.2004.11.054

Synthesis and biological evaluation of nucleobase-modified analogs of the anticancer compounds 3'-C-ethynyluridine (EUrd) and 3'-C-ethynylcytidine (ECyd)

Patrick J Hrdlicka, Jan S Jepsen, Claus Nielsen, Jesper Wengel, Jan Stenvang

26 Citations (Scopus)

Abstract

A series of nucleobase-modified analogs of the anticancer compounds 3'-C-ethynyluridine (EUrd) and 3'-C-ethynylcytidine (ECyd) were designed to overcome the strict substrate specificity of the activating uridine-cytidine kinase. EUrd, ECyd and target nucleosides were obtained using a short convergent synthetic route utilizing diacetone-alpha-D-glucose as starting material. 5-Iodo-substituted EUrd was the most potent inhibitor among the novel nucleobase-modified analogs in in vitro assays against human adenocarcinoma breast and prostate cancer cells with IC50 values down to 35 nM.

Original language	English
Journal	Bioorganic & Medicinal Chemistry
Volume	13
Issue number	4
Pages (from-to)	1249-60
Number of pages	12
ISSN	0968-0896
DOIs	https://doi.org/10.1016/j.bmc.2004.11.054
Publication status	Published - 15 Feb 2005

Keywords

Antineoplastic Agents
Cell Line, Tumor
Cytidine
Drug Screening Assays, Antitumor
Humans
Magnetic Resonance Spectroscopy
Uridine

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/j.bmc.2004.11.054

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Synthesis and biological evaluation of nucleobase-modified analogs of the anticancer compounds 3'-C-ethynyluridine (EUrd) and 3'-C-ethynylcytidine (ECyd). / Hrdlicka, Patrick J; Jepsen, Jan S; Nielsen, Claus et al.

In: Bioorganic & Medicinal Chemistry, Vol. 13, No. 4, 15.02.2005, p. 1249-60.

Research output: Contribution to journal › Journal article › Research › peer-review

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abstract = "A series of nucleobase-modified analogs of the anticancer compounds 3'-C-ethynyluridine (EUrd) and 3'-C-ethynylcytidine (ECyd) were designed to overcome the strict substrate specificity of the activating uridine-cytidine kinase. EUrd, ECyd and target nucleosides were obtained using a short convergent synthetic route utilizing diacetone-alpha-D-glucose as starting material. 5-Iodo-substituted EUrd was the most potent inhibitor among the novel nucleobase-modified analogs in in vitro assays against human adenocarcinoma breast and prostate cancer cells with IC50 values down to 35 nM.",

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AU - Jepsen, Jan S

AU - Nielsen, Claus

AU - Wengel, Jesper

AU - Stenvang, Jan

PY - 2005/2/15

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KW - Antineoplastic Agents

KW - Cell Line, Tumor

KW - Cytidine

KW - Drug Screening Assays, Antitumor

KW - Humans

KW - Magnetic Resonance Spectroscopy

KW - Uridine

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DO - 10.1016/j.bmc.2004.11.054

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SN - 0968-0896

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EP - 1260

JO - Bioorganic & Medicinal Chemistry

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ER -

Synthesis and biological evaluation of nucleobase-modified analogs of the anticancer compounds 3'-C-ethynyluridine (EUrd) and 3'-C-ethynylcytidine (ECyd)

Abstract

Keywords

UN SDGs

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