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 Citationer (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.

Originalsprog	Engelsk
Tidsskrift	Bioorganic & Medicinal Chemistry
Vol/bind	13
Udgave nummer	4
Sider (fra-til)	1249-60
Antal sider	12
ISSN	0968-0896
DOI	https://doi.org/10.1016/j.bmc.2004.11.054
Status	Udgivet - 15 feb. 2005

FN’s Verdensmål

Dette resultat bidrager til følgende verdensmål

Adgang til dokumentet

10.1016/j.bmc.2004.11.054

Citationsformater

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.
I: Bioorganic & Medicinal Chemistry, Bind 13, Nr. 4, 15.02.2005, s. 1249-60.

Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › peer review

@article{1c71d69931b94e3eb279aee8f23c9a51,

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

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.",

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

author = "Hrdlicka, {Patrick J} and Jepsen, {Jan S} and Claus Nielsen and Jesper Wengel and Jan Stenvang",

year = "2005",

month = feb,

day = "15",

doi = "10.1016/j.bmc.2004.11.054",

language = "English",

volume = "13",

pages = "1249--60",

journal = "Bioorganic & Medicinal Chemistry",

issn = "0968-0896",

publisher = "Pergamon Press",

number = "4",

}

TY - JOUR

T1 - Synthesis and biological evaluation of nucleobase-modified analogs of the anticancer compounds 3'-C-ethynyluridine (EUrd) and 3'-C-ethynylcytidine (ECyd)

AU - Hrdlicka, Patrick J

AU - Jepsen, Jan S

AU - Nielsen, Claus

AU - Wengel, Jesper

AU - Stenvang, Jan

PY - 2005/2/15

Y1 - 2005/2/15

N2 - 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.

AB - 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.

KW - Antineoplastic Agents

KW - Cell Line, Tumor

KW - Cytidine

KW - Drug Screening Assays, Antitumor

KW - Humans

KW - Magnetic Resonance Spectroscopy

KW - Uridine

U2 - 10.1016/j.bmc.2004.11.054

DO - 10.1016/j.bmc.2004.11.054

M3 - Journal article

C2 - 15670934

SN - 0968-0896

VL - 13

SP - 1249

EP - 1260

JO - Bioorganic & Medicinal Chemistry

JF - Bioorganic & Medicinal Chemistry

IS - 4

ER -

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

Abstract

FN’s Verdensmål

Adgang til dokumentet

Fingeraftryk

Citationsformater