4'-Ethynyl-2'-deoxyadenosine

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4'-Ethynyl-2'-deoxyadenosine (4'-E-dA), a nucleoside reverse transcriptase (RT) inhibitor, is an antiretroviral agent which is potent against drug-resistant HIV variants, with an EC₅₀ of 98 nM in MT-4 cells for anti-HIV-1 activity. 4'-Ethynyl-2'-deoxyadenosine 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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4'-Ethynyl-2'-deoxyadenosine Chemical Structure

CAS No. : 306305-07-7

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Biological Activity
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Description

4'-Ethynyl-2'-deoxyadenosine (4'-E-dA), a nucleoside reverse transcriptase (RT) inhibitor, is an antiretroviral agent which is potent against drug-resistant HIV variants, with an EC₅₀ of 98 nM in MT-4 cells for anti-HIV-1 activity^[1]. 4'-Ethynyl-2'-deoxyadenosine is a click chemistry reagent, it contains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups.

IC₅₀ & Target

HIV-1

Cellular Effect

Cell Line	Type	Value	Description	References
HeLa	EC₅₀	0.0068 μM Compound: 72	Tested in vitro against HIV-1 104pre from HeLa-CD4-LT4-beta gal-cells using MAGI assay Tested in vitro against HIV-1 104pre from HeLa-CD4-LT4-beta gal-cells using MAGI assay	[PMID: 11087576]
MT4	EC₅₀	0.0098 μM Compound: 45	Antiviral activity against HIV-1 infected in human MT-4 cells assessed as inhibition of viral-induced cytopathogenicity after 4 days by MTT assay Antiviral activity against HIV-1 infected in human MT-4 cells assessed as inhibition of viral-induced cytopathogenicity after 4 days by MTT assay	[PMID: 23795238]
MT4	EC₅₀	0.012 μM Compound: 72	Tested in vitro against HIV-1 LAI from MT-4 cells using MTT assay Tested in vitro against HIV-1 LAI from MT-4 cells using MTT assay	[PMID: 11087576]
MT4	CC₅₀	11.7 μM Compound: 72	Tested in vitro against MT-4 cells using MTT assay Tested in vitro against MT-4 cells using MTT assay	[PMID: 11087576]
MT4	CC₅₀	16 μM Compound: 45	Cytotoxicity against human MT4 cells after 4 days by MTT assay Cytotoxicity against human MT4 cells after 4 days by MTT assay	[PMID: 23795238]

Molecular Weight

275.26

Formula

C₁₂H₁₃N₅O₃

CAS No.

306305-07-7

SMILES

OC[C@]1(C#C)[C@H](C[C@H](N2C=NC3=C(N=CN=C32)N)O1)O

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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]. Ohrui H, et al. 4'-C-substituted-2'-deoxynucleosides: a family of antiretroviral agents which are potent against drug-resistant HIV variants. Curr Drug Targets Infect Disord. 2001 May;1(1):1-10. [Content Brief]