2’-β-C-Ethynylcytidine

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2’-β-C-Ethynylcytidine is a purine nucleoside analog. Purine nucleoside analogs have broad antitumor activity targeting indolent lymphoid malignancies. Anticancer mechanisms in this process rely on inhibition of DNA synthesis, induction of apoptosis, etc. 2’-β-C-Ethynylcytidine is a click chemistry reagent, it contains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups.

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2’-β-C-Ethynylcytidine Chemical Structure

CAS No. : 188413-99-2

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Biological Activity
Purity & Documentation
References
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Description

2’-β-C-Ethynylcytidine is a purine nucleoside analog. Purine nucleoside analogs have broad antitumor activity targeting indolent lymphoid malignancies. Anticancer mechanisms in this process rely on inhibition of DNA synthesis, induction of apoptosis, etc^[1]. 2’-β-C-Ethynylcytidine is a click chemistry reagent, it contains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups.

Cellular Effect

Cell Line	Type	Value	Description	References
A549	CC₅₀	> 100 μM Compound: 13	Cytotoxicity against human A549 cells assessed as intracellular ATP level by Celltiter-Glo luminescent assay Cytotoxicity against human A549 cells assessed as intracellular ATP level by Celltiter-Glo luminescent assay	[PMID: 20457821]
A549	EC₅₀	> 100 μM Compound: 13	Antiviral activity against at 0.3 MOI Dengue virus 2 infected in human A549 cells assessed as level of E protein after 48 hrs by ELISA Antiviral activity against at 0.3 MOI Dengue virus 2 infected in human A549 cells assessed as level of E protein after 48 hrs by ELISA	[PMID: 20457821]
BHK-21	EC₅₀	> 100 μM Compound: NM176	Antiviral activity against YFV infected in BHK-21 cells assessed as inhibition of virus-induced cytopathogenicity after 3 to 4 days by MTT assay Antiviral activity against YFV infected in BHK-21 cells assessed as inhibition of virus-induced cytopathogenicity after 3 to 4 days by MTT assay	[PMID: 26443549]
BHK-21	EC₅₀	> 100 μM Compound: NM176	Antiviral activity against Reo-1 virus infected in BHK-21 cells assessed as inhibition of virus-induced cytopathogenicity after 3 to 4 days by MTT assay Antiviral activity against Reo-1 virus infected in BHK-21 cells assessed as inhibition of virus-induced cytopathogenicity after 3 to 4 days by MTT assay	[PMID: 26443549]
KB	IC₅₀	> 350 μM Compound: 55	Concentration required to inhibit 50% of human epidermoid KB cell growth was measured(in vitro) using MTT assay. Concentration required to inhibit 50% of human epidermoid KB cell growth was measured(in vitro) using MTT assay.	[PMID: 9667977]
L1210	IC₅₀	> 350 μM Compound: 55	Concentration required to inhibit 50% of murine leukemia L1210 cell growth was measured(in vitro) using MTT assay. Concentration required to inhibit 50% of murine leukemia L1210 cell growth was measured(in vitro) using MTT assay.	[PMID: 9667977]
MT4	CC₅₀	> 100 μM Compound: NM176	Cytotoxicity against human MT4 cells assessed as cell viability after 96 hrs by MTT assay Cytotoxicity against human MT4 cells assessed as cell viability after 96 hrs by MTT assay	[PMID: 26443549]
MT4	CC₅₀	≥ 100 μM Compound: NM 176	Cytotoxicity against human MT4 cells after 96 hrs by MTT assay Cytotoxicity against human MT4 cells after 96 hrs by MTT assay	[PMID: 20359898]
Vero	CC₅₀	> 100 μM Compound: 2'-EtynCyt	Cytotoxicity against african green monkey Vero 76 cells after 48 to 96 hrs by crystal violet staining Cytotoxicity against african green monkey Vero 76 cells after 48 to 96 hrs by crystal violet staining	[PMID: 22047799]
Vero	CC₅₀	> 100 μM Compound: 2'-C-ethynyl-cytidine	Cytotoxicity against african green monkey Vero 76 cells after 48 to 96 hrs by MTT assay Cytotoxicity against african green monkey Vero 76 cells after 48 to 96 hrs by MTT assay	[PMID: 22513121]
Vero	EC₅₀	> 100 μM Compound: NM 176	Antiviral activity against HSV1 KOS infected in african green monkey Vero cells after 3 days by plaque reduction assay Antiviral activity against HSV1 KOS infected in african green monkey Vero cells after 3 days by plaque reduction assay	[PMID: 20359898]
Vero	EC₅₀	> 100 μM Compound: NM 176	Antiviral activity against Vaccinia virus Elstree-Lister infected in african green monkey Vero cells after 3 days by plaque reduction assay Antiviral activity against Vaccinia virus Elstree-Lister infected in african green monkey Vero cells after 3 days by plaque reduction assay	[PMID: 20359898]
Vero	EC₅₀	> 100 μM Compound: NM 176	Antiviral activity against RSV A2 infected in african green monkey Vero cells after 5 days by plaque reduction assay Antiviral activity against RSV A2 infected in african green monkey Vero cells after 5 days by plaque reduction assay	[PMID: 20359898]
Vero	EC₅₀	18 μM Compound: NM176	Antiviral activity against Human poliovirus 1 strain Sabin infected African green monkey Vero 76 cells assessed as reduction in plaque number treated after viral infection measured after 2 days by plaque reduction assay Antiviral activity against Human poliovirus 1 strain Sabin infected African green monkey Vero 76 cells assessed as reduction in plaque number treated after viral infection measured after 2 days by plaque reduction assay	10.1007/s00044-012-0342-1
Vero	EC₅₀	23 μM Compound: 2'-EtynCyt	Antiviral activity against Human poliovirus 1 strain Sabin Chat infected in african green monkey Vero 76 cells assessed as virus-induced reduction of plaque formation after 2 days using crystal violet staining Antiviral activity against Human poliovirus 1 strain Sabin Chat infected in african green monkey Vero 76 cells assessed as virus-induced reduction of plaque formation after 2 days using crystal violet staining	[PMID: 22047799]
Vero	EC₅₀	23 μM Compound: NM 176	Antiviral activity against Polio virus type1 Sabin strain Chat infected in african green monkey Vero cells after 2 days by plaque reduction assay Antiviral activity against Polio virus type1 Sabin strain Chat infected in african green monkey Vero cells after 2 days by plaque reduction assay	[PMID: 20359898]
Vero	EC₅₀	23 μM Compound: NM176	Antiviral activity against Human coxsackievirus B2 infected in African green monkey Vero 76 cells assessed as reduction in plaque number treated after viral infection measured after 3 days by plaque reduction assay Antiviral activity against Human coxsackievirus B2 infected in African green monkey Vero 76 cells assessed as reduction in plaque number treated after viral infection measured after 3 days by plaque reduction assay	10.1007/s00044-012-0342-1
Vero	EC₅₀	27 μM Compound: 2'-EtynCyt	Antiviral activity against Human coxsackievirus B5 Ohio-1 infected in african green monkey Vero 76 cells assessed as reduction of virus-induced plaque formation after 3 days using crystal violet staining Antiviral activity against Human coxsackievirus B5 Ohio-1 infected in african green monkey Vero 76 cells assessed as reduction of virus-induced plaque formation after 3 days using crystal violet staining	[PMID: 22047799]
Vero	EC₅₀	27 μM Compound: NM 176	Antiviral activity against Human coxsackievirus B2 Ohio-1 infected in african green monkey Vero cells after 3 days by plaque reduction assay Antiviral activity against Human coxsackievirus B2 Ohio-1 infected in african green monkey Vero cells after 3 days by plaque reduction assay	[PMID: 20359898]
Vero 76	CC₅₀	> 100 μM Compound: 2'-EtynCyt	Cytotoxicity against mock-infected african green monkey Vero 76 cells assessed as reduction in cell viability after 48 to 96 hrs by MTT assay Cytotoxicity against mock-infected african green monkey Vero 76 cells assessed as reduction in cell viability after 48 to 96 hrs by MTT assay	[PMID: 27161176]
Vero 76	CC₅₀	> 100 μM Compound: Eth-Cyt	Cytotoxicity against mock-infected African green monkey Vero 76 cells assessed as reduction in proliferation after 48 to 96 hrs by MTT method Cytotoxicity against mock-infected African green monkey Vero 76 cells assessed as reduction in proliferation after 48 to 96 hrs by MTT method	[PMID: 25014745]
Vero 76	EC₅₀	> 100 μM Compound: Eth-Cyt	Antiviral activity against CVB-5 virus Faulkner ATCC VR-185 infected in african green monkey Vero-76 cells after 3 days by plaque reduction assay Antiviral activity against CVB-5 virus Faulkner ATCC VR-185 infected in african green monkey Vero-76 cells after 3 days by plaque reduction assay	[PMID: 26479028]
Vero 76	CC₅₀	> 100 μM Compound: NM176	Cytotoxicity against african green monkey Vero 76 cells assessed as cell viability after 48 to 96 hrs by crystal violet staining method Cytotoxicity against african green monkey Vero 76 cells assessed as cell viability after 48 to 96 hrs by crystal violet staining method	[PMID: 26443549]
Vero 76	EC₅₀	> 100 μM Compound: NM176	Antiviral activity against human RSV infected in african green monkey Vero76 cells assessed as inhibition of virus-induced cytopathogenicity after 5 days by plaque reduction assay Antiviral activity against human RSV infected in african green monkey Vero76 cells assessed as inhibition of virus-induced cytopathogenicity after 5 days by plaque reduction assay	[PMID: 26443549]
Vero 76	EC₅₀	18 μM Compound: NM 176	Antiviral activity against Human poliovirus 1 strain Sabin infected African green monkey Vero76 cells assessed as reduction of virus-induced plaque reduction after 2 days by MTT assay Antiviral activity against Human poliovirus 1 strain Sabin infected African green monkey Vero76 cells assessed as reduction of virus-induced plaque reduction after 2 days by MTT assay	10.1007/s00044-010-9513-0
Vero 76	EC₅₀	23 μM Compound: 2'-C-ethynyl-cytidine	Antiviral activity against Polio virus type 1 strain sabin ATCC VR-1562 infected in african green monkey Vero-76 cells assessed as reduction in viral plaque after 2 days by crystal violet staining Antiviral activity against Polio virus type 1 strain sabin ATCC VR-1562 infected in african green monkey Vero-76 cells assessed as reduction in viral plaque after 2 days by crystal violet staining	[PMID: 22513121]
Vero 76	EC₅₀	23 μM Compound: NM 176	Antiviral activity against Human coxsackievirus B2 infected African green monkey Vero76 cells assessed as reduction of virus-induced plaque reduction after 3 days by MTT assay Antiviral activity against Human coxsackievirus B2 infected African green monkey Vero76 cells assessed as reduction of virus-induced plaque reduction after 3 days by MTT assay	10.1007/s00044-010-9513-0
Vero 76	EC₅₀	23 μM Compound: 2'-EtynCyt	Antiviral activity against Human poliovirus 1 strain Sabin infected in Vero 76 cells after 2 days by crystal violet staining based plaque reduction assay Antiviral activity against Human poliovirus 1 strain Sabin infected in Vero 76 cells after 2 days by crystal violet staining based plaque reduction assay	[PMID: 27161176]
Vero 76	EC₅₀	23 μM Compound: Eth-Cyt	Antiviral activity against Poliovirus 1 strain Sabin ATCC VR-1562 infected in Vero 76 cells after 2 days by plaque reduction assays Antiviral activity against Poliovirus 1 strain Sabin ATCC VR-1562 infected in Vero 76 cells after 2 days by plaque reduction assays	[PMID: 25014745]
Vero 76	EC₅₀	23 μM Compound: Eth-Cyt	Antiviral activity against RSVA2 ATCC VR-1540 infected in african green monkey Vero-76 cells after 5 days by plaque reduction assay Antiviral activity against RSVA2 ATCC VR-1540 infected in african green monkey Vero-76 cells after 5 days by plaque reduction assay	[PMID: 26479028]
Vero 76	EC₅₀	25 μM Compound: NM176	Antiviral activity against Human poliovirus 1 Sabin infected in african green monkey Vero76 cells assessed as inhibition of virus-induced cytopathogenicity by plaque reduction assay Antiviral activity against Human poliovirus 1 Sabin infected in african green monkey Vero76 cells assessed as inhibition of virus-induced cytopathogenicity by plaque reduction assay	[PMID: 26443549]
Vero 76	EC₅₀	27 μM Compound: 2'-C-ethynyl-cytidine	Antiviral activity against Coxsackie virus type B5 Ohio-1 ATCC VR-29 infected in african green monkey Vero-76 cells assessed as reduction in viral plaque after 3 days by crystal violet staining Antiviral activity against Coxsackie virus type B5 Ohio-1 ATCC VR-29 infected in african green monkey Vero-76 cells assessed as reduction in viral plaque after 3 days by crystal violet staining	[PMID: 22513121]
Vero 76	EC₅₀	27 μM Compound: Eth-Cyt	Antiviral activity against Human poliovirus 1 strain Sabin 1 virus infected in african green monkey Vero-76 cells after 2 days by plaque reduction assay Antiviral activity against Human poliovirus 1 strain Sabin 1 virus infected in african green monkey Vero-76 cells after 2 days by plaque reduction assay	[PMID: 26479028]
Vero 76	EC₅₀	27 μM Compound: 2'-EtynCyt	Antiviral activity against CVB-2 infected in Vero 76 cells after 3 days by crystal violet staining based plaque reduction assay Antiviral activity against CVB-2 infected in Vero 76 cells after 3 days by crystal violet staining based plaque reduction assay	[PMID: 27161176]
Vero 76	EC₅₀	27 μM Compound: Eth-Cyt	Antiviral activity against Coxsackievirus B5 Faulkner (ATCC VR-185) infected in Vero 76 cells after 3 days by plaque reduction assays Antiviral activity against Coxsackievirus B5 Faulkner (ATCC VR-185) infected in Vero 76 cells after 3 days by plaque reduction assays	[PMID: 25014745]
Vero 76	EC₅₀	30 μM Compound: NM176	Antiviral activity against human CVB5 infected in african green monkey Vero76 cells assessed as inhibition of virus-induced cytopathogenicity after 3 days by plaque reduction assay Antiviral activity against human CVB5 infected in african green monkey Vero76 cells assessed as inhibition of virus-induced cytopathogenicity after 3 days by plaque reduction assay	[PMID: 26443549]

Molecular Weight

267.24

Formula

C₁₁H₁₃N₃O₅

CAS No.

188413-99-2

SMILES

O[C@@H]1[C@@H](CO)O[C@@H](N2C(N=C(N)C=C2)=O)[C@]1(C#C)O

Shipping

Room temperature in continental US; may vary elsewhere.

Storage

Please store the product under the recommended conditions in the Certificate of Analysis.

Purity & Documentation

Handling Instructions (2659 KB)

References

[1]. Robak T, Robak P. Purine nucleoside analogs in the treatment of rarer chronic lymphoid leukemias. Curr Pharm Des. 2012;18(23):3373-88. [Content Brief]