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Ethynylcytidine

Ethynylcytidine is a synthetic cytidine nucleoside containing a covalently bound ethynyl group with potential antineoplastic and radiosensitizing activities. 3'-C-ethynylcytidine is metabolized in tumor cells to ethynylcytidine triphosphate (ECTP), which inhibits RNA synthesis by competitive inhibition of RNA polymerases I, II and III; subsequently, RNase L is activated, resulting in apoptosis. RNase L is a potent antiviral and antiproliferative endoribonuclease that cleaves singled stranded RNA, causes 28s rRNA fragmentation, and activates Janus Kinase (JAK), a mitochondrial-dependent apoptosis signaling molecule. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus)

Current developer:   GlaxoSmithKline

 1: Schott S, Wallwiener M, Kootz B, Seeger H, Fehm T, Neubauer H. ATP chemosensitivity testing of new antitumor duplex drugs linking 3;-C-ethynylycytidine (ECyd) and 2 -deoxy-5-fluorouridine (5-FdU) in comparison to standard cytostatica and combinations thereof. Invest New Drugs. 2009 Dec 9. [Epub ahead of print] PubMed PMID: 19997962.

2: Bijnsdorp IV, Schwendener RA, Schott H, Fichtner I, Smid K, Laan AC, Schott S, Losekoot N, Honeywell RJ, Peters GJ. Cellular pharmacology of multi- and duplex drugsconsisting of ethynylcytidine and 5-fluoro-2'-deoxyuridine. Invest New Drugs. 2009 Dec 3. [Epub ahead of print] PubMed PMID: 19957099.

3: Wataya Y, Naito T, Sato A, Hiramoto A, Kitade Y, Sasaki T, Matsuda A, Fukushima M, Kim HS. Molecular mechanisms of apoptosis induced by 3'-ethynylcytidine. Nucleic Acids Symp Ser (Oxf). 2009;(53):291-2. PubMed PMID: 19749375.

4: Schott H, Schott S, Schwendener RA. Synthesis and in vitro activities of new anticancer duplex drugs linking 2'-deoxy-5-fluorouridine (5-FdU) with 3'-C-ethynylcytidine (ECyd) via a phosphodiester bonding. Bioorg Med Chem. 2009 Oct 1;17(19):6824-31. Epub 2009 Aug 21. PubMed PMID: 19744858.

5: Takada A, Kamiya H, Shuto S, Matsuda A, Harashima H. PK-PD modeling of 1-(3-C-ethynyl-beta-D-ribo-pentofuranosyl)cytosine and the enhanced antitumor effect of its phospholipid derivatives in long-circulating liposomes. Int J Pharm. 2009 Jul 30;377(1-2):52-9. Epub 2009 May 6. PubMed PMID: 19426792.

6: Bijnsdorp IV, Schwendener RA, Schott H, Schott S, Fichtner I, Honeywell RJ, Losekoot N, Laan AC, Peters GJ. In vitro activity and mechanism of action of a duplex and multidrug of ethynylcytidine and 5-fluorodeoxyuridine. Nucleic Acids Symp Ser (Oxf). 2008;(52):651. PubMed PMID: 18776548.

7: Galmarini CM, Popowycz F, Joseph B. Cytotoxic nucleoside analogues: different strategies to improve their clinical efficacy. Curr Med Chem. 2008;15(11):1072-82. Review. PubMed PMID: 18473803.

8: Bayés M, Rabasseda X. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2008 Jan-Feb;30(1):67-99. PubMed PMID: 18389098.

9: Naito T, Yokogawa T, Kim HS, Matsuda A, Sasaki T, Fukushima M, Kitade Y, Wataya Y. A novel apoptotic pathway of 3'-Ethynylcytidine(ECyd) involving the inhibition of RNA synthesis--the possibility of RNase L activated pathway as a target of ECyd. Nucleic Acids Symp Ser (Oxf). 2007;(51):435-6. PubMed PMID: 18029773.

10: Kazuno H, Shimamoto Y, Tsujimoto H, Fukushima M, Matsuda A, Sasaki T. Mechanism of action of a new antitumor ribonucleoside, 1-(3-C-ethynyl-beta-D-ribo-pentofuranosyl)cytosine (ECyd, TAS-106), differs from that of 5-fluorouracil. Oncol Rep. 2007 Jun;17(6):1453-60. PubMed PMID: 17487404.

11: Naito T, Yokogawa T, Kim HS, Matsuda A, Sasaki T, Fukushima M, Kitade Y, Wataya Y. An apoptotic pathway of 3'-Ethynylcytidine(ECyd) involving the inhibition of RNA synthesis mediated by RNase L. Nucleic Acids Symp Ser (Oxf). 2006;(50):103-4. PubMed PMID: 17150838.

12: Hrdlicka PJ, Jepsen JS, Wengel J. Synthesis and biological evaluation of conformationally restricted and nucleobase-modified analogs of the anticancer compound 3'-C-ethynylcytidine (ECyd). Nucleosides Nucleotides Nucleic Acids. 2005;24(5-7):397-400. PubMed PMID: 16247958.

13: Hrdlicka PJ, Andersen NK, Jepsen JS, Hansen FG, Haselmann KF, Nielsen C, Wengel J. Synthesis and biological evaluation of branched and conformationally restricted analogs of the anticancer compounds 3'-C-ethynyluridine (EUrd) and 3'-C-ethynylcytidine (ECyd). Bioorg Med Chem. 2005 Apr 1;13(7):2597-621. PubMed PMID: 15755661.

14: Hrdlicka PJ, Jepsen JS, Nielsen C, Wengel J. Synthesis and biological evaluation of nucleobase-modified analogs of the anticancer compounds 3'-C-ethynyluridine (EUrd) and 3'-C-ethynylcytidine (ECyd). Bioorg Med Chem. 2005 Feb 15;13(4):1249-60. PubMed PMID: 15670934.

15: Hasegawa T, Futagami M, Kim HS, Matsuda A, Wataya Y. Analysis of single nucleotide polymorphisms in uridine/cytidine kinase gene encoding metabolic enzyme of 3'-ethynylcytidine. Nucleic Acids Res Suppl. 2002;(2):237-8. PubMed PMID: 12903193.

16: Wataya Y, Futagami M, Naito T, Uchikubo Y, Yokogawa T, Takenaka K, Kim HS, Matsuda A, Fukushima M, Kitade Y. Anticancer molecular mechanism of 3'-ethynylcytidine (ECyd). Nucleic Acids Res Suppl. 2001;(1):233-4. PubMed PMID: 12836350.

17: Matsuoka K, Kitamura R, Matsushima E, Kawaguchi Y. Determination of 3'-C-ethynylcytidine in human plasma and urine by liquid chromatographic-electrospray ionization tandem mass spectrometry. J Pharm Biomed Anal. 2003 Feb 5;31(1):47-55. PubMed PMID: 12560048.

18: Koizumi K, Shimamoto Y, Azuma A, Wataya Y, Matsuda A, Sasaki T, Fukushima M. Cloning and expression of uridine/cytidine kinase cDNA from human fibrosarcoma cells. Int J Mol Med. 2001 Sep;8(3):273-8. PubMed PMID: 11494055.

19: Kitamura R, Matsuoka K, Matsushima E, Kawaguchi Y. Improvement in precision of the liquid chromatographic-electrospray ionization tandem mass spectrometric analysis of 3'-C-ethynylcytidine in rat plasma. J Chromatogr B Biomed Sci Appl. 2001 Apr 15;754(1):113-9. PubMed PMID: 11318405.

20: Tabata S, Tanaka M, Endo Y, Obata T, Matsuda A, Sasaki T. Anti-tumor mechanisms of 3'-ethynyluridine and 3'-ethynylcytidine as RNA synthesis inhibitors: development and characterization of 3'-ethynyluridine-resistant cells. Cancer Lett. 1997 Jun 24;116(2):225-31. PubMed PMID: 9215867.

21: Kanda H, Takatori S, Matsuda A, Sasaki T, Tanaka M, Fukushima M, Wataya Y. Cytotoxic mechanisms of new antitumor nucleoside analogues, 3'-ethynylcytidine (ECyd) and 3'-ethynyluridine (EUrd). Nucleic Acids Symp Ser. 1997;(37):137-8. PubMed PMID: 9586037.