Ethynylcytidine
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MedKoo CAT#: 201330

CAS#: 180300-43-0

Description: 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).

Chemical Structure

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Ethynylcytidine
CAS# 180300-43-0
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 201330
Name: Ethynylcytidine
CAS#: 180300-43-0
Chemical Formula: C11H13N3O5
Exact Mass: 267.09
Molecular Weight: 267.238
Elemental Analysis: C, 49.44; H, 4.90; N, 15.72; O, 29.93

Price and Availability

Size Price Availability Quantity
1mg USD 215 2 Weeks
5mg USD 415 2 Weeks
10mg USD 660 2 Weeks
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Synonym: ECydTAS106TAS 1063CEthynylcytidineAIDS241582AIDS241582; SB596168 3Ethynylcytidine.

IUPAC/Chemical Name: 1-(3-C-Ethynyl-beta-D-ribo-pentofuranosyl)cytosine

InChi Key: JFIWEPHGRUDAJN-DYUFWOLASA-N

InChi Code: InChI=1S/C11H13N3O5/c1-2-11(18)6(5-15)19-9(8(11)16)14-4-3-7(12)13-10(14)17/h1,3-4,6,8-9,15-16,18H,5H2,(H2,12,13,17)/t6-,8+,9-,11-/m1/s1

SMILES Code: O=C1N([C@H]2[C@@H]([C@]([C@@H](CO)O2)(C#C)O)O)C=CC(N)=N1

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).

Solubility: Soluble in DMSO, not in water

Shelf Life: >5 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

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Product Data:
Product Data
Instruction:
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Biological target: Ethynylcytidine (ECyD), a nucleoside analog and a potent inhibitor of RNA synthesis, inhibits RNA polymerases I, II and II.
In vitro activity: After short term incubation (48 h), FdU-Ecyd treatment of OC cells conferred a rapid dose-dependent decline of cell viability in platinum-sensitive A2780 and platinum-resistant A2780cis cells, suggesting that the effect of 5-FdU-ECyd is independent from platinum-resistance status (Figure 1A). Response to 5-FdU-ECyd was ~95-fold higher in A2780 cells (IC50 5-FdU-ECyd 0.04 μM vs. IC50 cisplatin 3.81 μM) and ~620-fold higher in A2780cis cells (IC50 5-FdU-ECyd 0.02 μM vs. IC50 cisplatin 12.4 μM), compared to equimolar cisplatin concentrations. Reference: Oncotarget. 2017 Sep 29; 8(44): 76935–76948. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5652753/
In vivo activity: Then, to address whether this hypothesis is active in tumor cells not only in vitro but also in vivo, this study assessed the effect of CDDP and ECyd on the expression levels of vRNAs in nude mice xenograft tumors. Consistent with in vitro data, the co-administration of ECyd statistically decreased the expression levels of vRNAs in nude mice xenograft tumors (Figure 4C), while no induction was observed using CDDP alone. Reference: BMC Cancer. 2014; 14: 562. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4131025/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 127.5 477.10
DMF 5.0 18.71
PBS (pH 7.2) 10.0 37.42

Preparing Stock Solutions

The following data is based on the product molecular weight 267.24 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Schott S, Wimberger P, Klink B, Grützmann K, Puppe J, Wauer US, Klotz DM, Schröck E, Kuhlmann JD. The conjugated antimetabolite 5-FdU-ECyd and its cellular and molecular effects on platinum-sensitive vs. -resistant ovarian cancer cells in vitro. Oncotarget. 2017 Aug 14;8(44):76935-76948. doi: 10.18632/oncotarget.20260. PMID: 29100359; PMCID: PMC5652753. 2. Fukushima H, Abe T, Sakamoto K, Tsujimoto H, Mizuarai S, Oie S. 3'-ethynylcytidine, an RNA polymerase inhibitor, combined with cisplatin exhibits a potent synergistic growth-inhibitory effect via Vaults dysfunction. BMC Cancer. 2014 Aug 4;14:562. doi: 10.1186/1471-2407-14-562. PMID: 25087851; PMCID: PMC4131025.
In vitro protocol: 1. Schott S, Wimberger P, Klink B, Grützmann K, Puppe J, Wauer US, Klotz DM, Schröck E, Kuhlmann JD. The conjugated antimetabolite 5-FdU-ECyd and its cellular and molecular effects on platinum-sensitive vs. -resistant ovarian cancer cells in vitro. Oncotarget. 2017 Aug 14;8(44):76935-76948. doi: 10.18632/oncotarget.20260. PMID: 29100359; PMCID: PMC5652753. 2. Fukushima H, Abe T, Sakamoto K, Tsujimoto H, Mizuarai S, Oie S. 3'-ethynylcytidine, an RNA polymerase inhibitor, combined with cisplatin exhibits a potent synergistic growth-inhibitory effect via Vaults dysfunction. BMC Cancer. 2014 Aug 4;14:562. doi: 10.1186/1471-2407-14-562. PMID: 25087851; PMCID: PMC4131025.
In vivo protocol: 1. Fukushima H, Abe T, Sakamoto K, Tsujimoto H, Mizuarai S, Oie S. 3'-ethynylcytidine, an RNA polymerase inhibitor, combined with cisplatin exhibits a potent synergistic growth-inhibitory effect via Vaults dysfunction. BMC Cancer. 2014 Aug 4;14:562. doi: 10.1186/1471-2407-14-562. PMID: 25087851; PMCID: PMC4131025.

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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.