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).
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.
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.
| Chemical | |
|---|---|
| CAS Num | 180300-43-0 |
| Chemical Formula | C11H13N3O5 |
| Molecular Weight | 267.23802 |
| IUPAC Chemical Name | 1-(3-C-Ethynyl-beta-D-ribo-pentofuranosyl)cytosine |
| Exact Mass | 267.08552 |
| Elemental Analysis | C, 49.44; H, 4.90; N, 15.72; O, 29.93 |
| Synonym | ECydTAS106TAS 1063CEthynylcytidineAIDS241582AIDS241582; SB596168 3Ethynylcytidine. |
| Solubility | Soluble in DMSO, not in water |
| SMILES Code | O=C1N([C@H]2[C@@H]([C@]([C@@H](CO)O2)(C#C)O)O)C=CC(N)=N1 |
| Biological | |
| Targets and Effects | RNA polymerase inhibitor |
| Pathways | Apoptosis |
| Physical | |
| Appearance | Solid powder |
| Purity | >98% (or refer to the Certificate of Analysis) |
| Shipping Condition | Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs. |
| Storage Condition | Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years). |
| Shelf Life | >5 years if stored properly |
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