Art. -Nr.: HY-W013332

3-Deazaadenosine

32 Cited Publications

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Based on 32 publication(s) in Google Scholar

3-Deazaadenosine is an inhibitor of S-adenosylhomocysteine hydrolase, with a K_i of 3.9 μM; 3-Deazaadenosine has anti-inflammatory, anti-proliferative and anti-HIV activity.

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Reinheit: 98.53%
CAS. Nr.: 6736-58-9
Formel: C₁₁H₁₄N₄O₄
Molecular Weight:266.26

Speicherung:

Powder -20°C, 3 years ; In solvent -80°C, 6 months , -20°C, 1 month

3-Deazaadenosine Chemical Structure

CAS. Nr.: 6736-58-9

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Biologische Aktivität
- Beschreibung
- IC₅₀ & Target
- Cellular Effect
- In Vitro
Chemical Information
Publications (32)
Lösungsmittel & Löslichkeit
- In Vitro
- In Vivo
Protokoll
Reinheit & Dokumentation
Verweise
Help & FAQs
Classifications
Bioz

Biologische Aktivität

Beschreibung

3-Deazaadenosine is an inhibitor of S-adenosylhomocysteine hydrolase, with a K_i of 3.9 μM; 3-Deazaadenosine has anti-inflammatory, anti-proliferative and anti-HIV activity.

IC₅₀ & Target

HIV-1

Alle HIV Isoform-spezifische Produkte anzeigen :

Cellular Effect

Cell Line	Type	Value	Description	References
A549	IC₅₀	57.37 μM Compound: 3-DZA	Cytotoxicity against human A549 cells assessed as cell growth inhibition Cytotoxicity against human A549 cells assessed as cell growth inhibition	[PMID: 35809817]
HEp-2	IC₅₀	2 μM Compound: 2	Compound was evaluated for cytotoxicity against H.Ep.-2 cells, and concentration required to inhibit the growth of treated cells to 50% of untreated control. Compound was evaluated for cytotoxicity against H.Ep.-2 cells, and concentration required to inhibit the growth of treated cells to 50% of untreated control.	[PMID: 6708054]
L02	IC₅₀	94.43 μM Compound: 3-DZA	Cytotoxicity against human L02 cells assessed as cell growth inhibition Cytotoxicity against human L02 cells assessed as cell growth inhibition	[PMID: 35809817]
MCF7	IC₅₀	<100 nM Compound: 6, DZA	Cytotoxicity against human MCF7 cells Cytotoxicity against human MCF7 cells	[PMID: 26314922]
MCF7	IC₅₀	40.32 μM Compound: 3-DZA	Cytotoxicity against human MCF7 cells assessed as cell growth inhibition Cytotoxicity against human MCF7 cells assessed as cell growth inhibition	[PMID: 35809817]
MDA-MB-231	IC₅₀	<100 nM Compound: 6, DZA	Cytotoxicity against human MDA-MB-231 cells Cytotoxicity against human MDA-MB-231 cells	[PMID: 26314922]
MGC-803	IC₅₀	41.06 μM Compound: 3-DZA	Cytotoxicity against human MGC-803 cells assessed as cell growth inhibition Cytotoxicity against human MGC-803 cells assessed as cell growth inhibition	[PMID: 35809817]
SK-BR-3	IC₅₀	<100 nM Compound: 6, DZA	Cytotoxicity against human SKBR3 cells Cytotoxicity against human SKBR3 cells	[PMID: 26314922]

In Vitro

3-Deazaadenosine is an inhibitor of S-adenosylhomocysteine hydrolase, with a K_i of 3.9 μM. 3-Deazaadenosine shows anti-HIV effect, and inhibits p24 antigen in peripheral blood mononuclear (PBMCs) cells infected with HIV-1 isolates (A012 and A018) with IC₅₀s of 0.15 and 0.20 μM, respectively^[1]. 3-Deazaadenosine (1-100 μM) inhibits LPS-induced expression of TNF-α mRNA, increases DNA binding activity of NF-κB, and causes proteolytic degradation of IκBα, but Not IκBβ in RAW 264.7 cells. 3-Deazaadenosine (100 μM) enhances nuclear translocation of NF-κB, but blocks LPS-induced NF-κB transcriptional activity, and such inhibition is augmented by the addition of homocysteine^[2]. 3-Deazaadenosine (50, 100 μM) dose-dependently inhibits the phosphorylation of Raf and ERK, protein-dependent kinase 1, protein kinase B (Akt), and forkhead transcription factor FoxO1a. 3-Deazaadenosine (50 μM) suppresses vascular smooth muscle cell (VSMC) proliferation via interfering with Ras signaling^[3].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Chemical Information

CAS. Nr. 6736-58-9
Appearance Solid
Molecular Weight 266.26
Formel C₁₁H₁₄N₄O₄
Color White to off-white
SMILES

O[C@H]1[C@@H](O[C@H](CO)[C@H]1O)N2C3=C(C(N)=NC=C3)N=C2
Versand

Room temperature in continental US; may vary elsewhere.

Speicherung

Powder	-20°C	3 years
In solvent	-80°C	6 months
	-20°C	1 month

Publications (32)

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Journal Impact Factor

Cancer Res

M6A Demethylase ALKBH5 Regulates PD-L1 Expression and Tumor Immunoenvironment in Intrahepatic Cholangiocarcinoma. [Abstract]

2021 Sep 15;81(18):4778-4793. PMID: 34301762
J Clin Invest

Coenzyme A protects against ferroptosis via CoAlation of mitochondrial thioredoxin reductase. [Abstract]

2025 Jul 22;135(19):e190215. PMID: 40694424
Adv Sci (Weinh)

ZNF33B Promotes Japanese Encephalitis Virus Infection by Regulating the Stability of M6A-Modified Trim25 to Control the Autophagy Process. [Abstract]

2026 Jun 18:e76122. PMID: 42314059
Mol Biomed

Targeting the RNA-binding motif protein 15 suppresses prostate cancer progression and hormone therapy resistance by promoting androgen receptor degradation. [Abstract]

2026 Apr 8;7(1):47. PMID: 41949706
Cell Death Dis

TRIM17 promotes the progression of osteosarcoma by regulating PDK1 m6A modification-mediated AKT/mTOR pathway activation through ubiquitination of FTO. [Abstract]

2025 Oct 27;16(1):767. PMID: 41145484

3-Deazaadenosine purchased from MedChemExpress. Usage Cited in: Cell Death Dis. 2025 Oct 27;16(1):767. [Abstract]

3-Deazaadenosine (DAA: 1 μM 48 h). PDK1 mRNA levels were detected by qRT-PCR.
Cell Mol Biol Lett

WTAP/IGF2BP3-mediated GBE1 expression accelerates the proliferation and enhances stemness in pancreatic cancer cells via upregulating c-Myc. [Abstract]

2024 Jul 3;29(1):97. PMID: 38961325

3-Deazaadenosine purchased from MedChemExpress. Usage Cited in: Cell Mol Biol Lett. 2024 Jul 3;29(1):97. [Abstract]

The mRNA expression level of GBE1 in BXPC3 cells after 3-Deazaadenosine (DAA) treatment.

3-Deazaadenosine purchased from MedChemExpress. Usage Cited in: Cell Mol Biol Lett. 2024 Jul 3;29(1):97. [Abstract]

Protein expression level of GBE1 in BXPC3 cells after 3-Deazaadenosine (DAA) treatment.
Int J Biol Sci

Inhibition of IGF2BP1 attenuates renal injury and inflammation by alleviating m6A modifications and E2F1/MIF pathway. [Abstract]

2023 Jan 1;19(2):593-609. PMID: 36632449

3-Deazaadenosine purchased from MedChemExpress. Usage Cited in: Int J Biol Sci. 2023 Jan 1;19(2):593-609. [Abstract]

The protein levels of E2F1 and MIF were measured using WB in HK2 cells with IGF2BP1 knocked down, treated with or without 3-Deazaadenosine (DAA) for 12 h.
Arch Toxicol

Genetic variants in N6-methyladenosine are associated with bladder cancer risk in the Chinese population. [Abstract]

2021 Jan;95(1):299-309. PMID: 32964246

3-Deazaadenosine purchased from MedChemExpress. Usage Cited in: Arch Toxicol. 2021 Jan;95(1):299-309. [Abstract]

After treating with 3-Deazaadenosine (DAA, 50 mM), the global methylation inhibitor, EJ and J82 cell lines show decreased m6A modifcation level and reduced SOD2 expression level.
Oncogene

N6-methyladenosine demethyltransferase FTO mediated m6A modification of estrogen receptor alpha in non-small cell lung cancer tumorigenesis. [Abstract]

2024 Apr;43(17):1288-1302. PMID: 38443681

3-Deazaadenosine purchased from MedChemExpress. Usage Cited in: Oncogene. 2024 Apr;43(17):1288-1302. [Abstract]

The expression level of ESR1 protein in xenograft tumor tissues of the DMSO, 3-Deazaadenosine (DAA: 50 mg/kg) or AZD9496 treatment groups was detected by ELISA.
Cell Rep

RNA m6A Modification Functions in Larval Development and Caste Differentiation in Honeybee (Apis mellifera). [Abstract]

2021 Jan 5;34(1):108580. PMID: 33406439
Environ Pollut

linc01515 regulates PM2.5-induced oxidative stress via targeting NRF2 in airway epithelial cells. [Abstract]

2023 Aug 15;331(Pt 2):121798. PMID: 37169236
Atherosclerosis

The m6A demethylase FTO suppresses perivascular adipose tissue browning and exacerbates vascular injury via m6A-mediated destabilization of Irx3 mRNA and the IRX3/UCP1 axis. [Abstract]

2026 May 14:417:120788. PMID: 42155396
Cancer Cell Int

LncRNA AGAP2 antisense RNA 1 stabilized by insulin-like growth factor 2 mRNA binding protein 3 promotes macrophage M2 polarization in clear cell renal cell carcinoma through regulation of the microRNA-9-5p/THBS2/PI3K-Akt pathway. [Abstract]

2023 Dec 18;23(1):330. PMID: 38110984
Virulence

HIV-1 Vpr activates microglia by upregulating m6A modification through ubiquitin-proteasome pathway-mediated degradation of the demethylase ALKBH5. [Abstract]

2026 Dec;17(1):2645908. PMID: 41824629
Cancer Gene Ther

WTAP stabilized by USP7 contributes to enzalutamide resistance in prostate cancer via mediating AKT m6A-modification. [Abstract]

2026 Mar;33(3):277-288. PMID: 41981278
Eur J Pharmacol

Targeting the ALKBH5-NLRP3 positive feedback loop alleviates cardiomyocyte pyroptosis after myocardial infarction. [Abstract]

2025 Feb 15:989:177247. PMID: 39746531
Biomolecules

Apelin-13-Mediated Upregulation of METTL3 Ameliorates Alzheimer's Disease via Inhibiting Neuroinflammation Through m6A-Dependent Regulation of lncRNA BDNF-AS. [Abstract]

2025 Aug 18;15(8):1188. PMID: 40867632
Inflammation

HNRNPC-Mediated m6A Epitranscriptomics Drives CD80-Dependent Tubular Dysfunction in Sepsis-Induced AKI. [Abstract]

2025 Nov 7. PMID: 41199093
BMC Biol

GnRH-driven FTO-mediated RNA m6A modification promotes gonadotropin synthesis and secretion. [Abstract]

2024 May 3;22(1):104. PMID: 38702712
Am J Physiol Cell Physiol

ALKHB5-demethylated lncRNA SNHG15 promotes myeloma tumorigenicity by increasing chromatin accessibility and recruiting H3K36me3 modifier SETD2. [Abstract]

2024 Mar 1;326(3):C684-C697. PMID: 38145297
Cell Signal

METTL14-mediated depression of NEIL1 aggravates oxidative damage and mitochondrial dysfunction of lens epithelial cells through regulating KEAP1/NRF2 pathways. [Abstract]

2025 Mar:127:111623. PMID: 39855533
Water Biol Secur

2025 Apr 18.
J Neurosci

USP1/UAF1-stabilized METTL3 promotes reactive astrogliosis and improves functional recovery after spinal cord injury through m6A modification of YAP1 mRNA. [Abstract]

2023 Mar 1;43(9):1456-1474. PMID: 36653190
Genomics

SHMT2 promotes the tumorigenesis of renal cell carcinoma by regulating the m6A modification of PPAT. [Abstract]

2022 Jul;114(4):110424. PMID: 35798250
Cell Biol Int

FLOT1 Is a Novel Serum Biomarker of Ovarian Cancer Targeted by N6-methyladenosine Modification Inhibition. [Abstract]

2025 Jun;49(6):674-691. PMID: 40066501
Exp Cell Res

Irradiation of 125I seeds blocks glycolysis in pancreatic cancer by inhibiting KLF5 m6A methylation through the suppression of RBM15. [Abstract]

2025 May 1;448(1):114538. PMID: 40147709
Exp Cell Res

N6-methyladenosine modification of linc-OIP5 confers paclitaxel resistance in breast cancer through a DDX5-dependent mechanism. [Abstract]

2024 Oct 1;442(2):114226. PMID: 39209141
J Cancer

METTL14 Facilitates the Metastasis of Pancreatic Carcinoma by Stabilizing LINC00941 in an m6A-IGF2BP2-Dependent Manner. [Abstract]

2023 Apr 17;14(7):1117-1131. PMID: 37215454
Oncol Lett

METTL5 reprograms glycolytic metabolism and promotes non-small cell lung cancer progression by modifying PGAM1. [Abstract]

2026 Apr 20;31(6):254. PMID: 42057886
Transpl Immunol

Bushen Huoxue decotion-containing serum prevents chondrocyte pyroptosis in a m6A-dependent manner in facet joint osteoarthritis. [Abstract]

2024 Oct:86:102083. PMID: 38996984
bioRxiv

2024 May 18.
Research Square Print

2022 May.

Lösungsmittel & Löslichkeit

In Vitro:

DMSO : 130 mg/mL (488.24 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

H₂O : 100 mg/mL (375.57 mM; Need ultrasonic)

View the Complete Stock Solution Preparation Table

Preparing Stock Solutions

View the Complete Stock Solution Preparation Table

Concentration Solvent Mass

1 mg

5 mg

10 mg

Concentration

Solvent

Mass

1 mM

3.7557 mL

18.7786 mL

37.5573 mL

5 mM

0.7511 mL

3.7557 mL

7.5115 mL

10 mM

0.3756 mL

1.8779 mL

3.7557 mL

Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.

Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

* Note: If you choose water as the stock solution, please dilute it to the working solution, then filter and sterilize it with a 0.22 μm filter before use.

Molaritätsrechner

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Mass Mass

Konzentration Konzentration

Volumen Volumen

Molecular Weight Molecular Weight

Verdünnungsrechner

Konzentration _{(Stammlösung)} × Volumen _{(Stammlösung)} = Konzentration _{(Ziellösung)} × Volumen _{(Ziellösung)}

Konzentration _{(Stammlösung)} Konzentration _{(Stammlösung)}

Volumen _{(Stammlösung)} Volumen _{(Stammlösung)}

Konzentration _{(Ziellösung)} Konzentration _{(Ziellösung)}

Volumen _{(Ziellösung)} Volumen _{(Ziellösung)}

In Vivo:

Select the appropriate dissolution method based on your experimental animal and administration route.

Stock Solution Working Solution

For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for In Vivo experiments, it is recommended to prepare freshly and use it on the same day.
The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.

Protocol 1

Add each solvent one by one: 10% DMSO 40% PEG300 5% Tween-80 45% Saline

Solubility: ≥ 2.17 mg/mL (8.15 mM); Clear solution

This protocol yields a clear solution of ≥ 2.17 mg/mL (saturation unknown).

Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (21.7 mg/mL) to 400 μL PEG300, and mix evenly; then add 50 μL Tween-80 and mix evenly; then add 450 μL Saline to adjust the volume to 1 mL.

Protocol 2

Add each solvent one by one: 10% DMSO 90% (20% SBE-β-CD in Saline)

Solubility: ≥ 2.17 mg/mL (8.15 mM); Clear solution

This protocol yields a clear solution of ≥ 2.17 mg/mL (saturation unknown).

Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (21.7 mg/mL) to 900 μL 20% SBE-β-CD in Saline, and mix evenly.

Protocol 3

Add each solvent one by one: 10% DMSO 90% Corn Oil

Solubility: ≥ 2.17 mg/mL (8.15 mM); Clear solution

This protocol yields a clear solution of ≥ 2.17 mg/mL (saturation unknown). If the continuous dosing period exceeds half a month, please choose this protocol carefully.

Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (21.7 mg/mL) to 900 μL Corn oil, and mix evenly.

In Vivo Dissolution Calculator

Please enter the basic information of animal experiments:

Dosage Dosage
mg/kg
Animal Weight (Per Animal) Animal Weight (Per Animal)
g
Dosing Volume (Per Animal) Dosing Volume (Per Animal)
μL
Number of Animals Number of Animals

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.

Working solution concentration: 0.22 mg/mL

This product has good water solubility, please refer to the measured solubility data in water/PBS/Saline for details.

The concentration of the stock solution you require exceeds the measured solubility. The following solution is for reference only.If necessary, please contact

MedChemExpress (MCE) .

Protokoll

Cell Assay^[1]

The HIV-1 strains A012 and A018 are used in the assay. Inhibition of p24 antigen is measured. Briefly, PHA-stimulated peripheral blood mononuclear (PBMCs) are incubated with either HIV-1 strain for 1 h at 37°C at 200-fold the 50% tissue culture infectious dose (TCID₅₀) of the virus stock per 2 × 10⁵ PBMC cells. The TCID₅₀ is defined as the amount of virus stock at which 50% of the inoculated wells are positive. Cells are then grown in microtiter plates with different drug concentrations at 2 × 10⁵ cells per well. On day 4, cells are resuspended and split 1:3 with fresh media and 3-Deazaadenosine. Supernatant p24 antigen is determined on day 7 by ELISA^[1].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Reinheit & Dokumentation

Select Batch:

Reinheit: 99.98%

Assay: 99.98%

ee.: 99.98%

Data Sheet (278 KB)
SDS (420 KB)
- English - EN (420 KB)
- Français - FR (420 KB)
- Deutsch - DE (420 KB)
- Norwegian - NO (420 KB)
- Español - ES (420 KB)
- Swedish - SV (420 KB)
- Italian - IT (420 KB)
- Korean - KR (420 KB)
- Portuguese - PT (420 KB)
COA (2659 KB)
Elemental Analysis Report (2659 KB)
HNMR (2659 KB)
CNMR (2659 KB)
RP-HPLC (2659 KB)
NP-HPLC (2659 KB)
MS (2659 KB)
LCMS (2659 KB)
IR (2659 KB)
GC (2659 KB)
OR (2659 KB)
SDS-PAGE (2659 KB)
SEC-HPLC (2659 KB)
Other Report (2659 KB)
Handling Instructions (2659 KB)

Verweise

[1]. Gordon RK, et al. Anti-HIV-1 activity of 3-deaza-adenosine analogs. Inhibition of S-adenosylhomocysteine hydrolase and nucleotide congeners. Eur J Biochem. 2003 Sep;270(17):3507-17. [Content Brief]

[2]. Jeong SY, et al. 3-deazaadenosine, a S-adenosylhomocysteine hydrolase inhibitor, has dual effects on NF-kappaB regulation. Inhibition of NF-kappaB transcriptional activity and promotion of IkappaBalpha degradation. J Biol Chem. 1999 Jul 2;274(27):18981-8. [Content Brief]

[3]. Sedding DG, et al. 3-Deazaadenosine prevents smooth muscle cell proliferation and neointima formation by interfering with Ras signaling. Circ Res. 2009 May 22;104(10):1192-200. [Content Brief]

Help & FAQs

How should lyophilized recombinant proteins be reconstituted and stored?

1. Before opening the cap, centrifuge the vial at 13000 rpm for 20-30 seconds. This step will ensure that any lyophilized powder that may have adhered to the cap or walls is collected at the bottom of the vial, minimizing the risk of product loss.

Complete Stock Solution Preparation Table

Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

Optional Solvent	Concentration Solvent Mass	1 mg	5 mg	10 mg	25 mg
H₂O / DMSO	1 mM	3.7557 mL	18.7786 mL	37.5573 mL	93.8932 mL
	5 mM	0.7511 mL	3.7557 mL	7.5115 mL	18.7786 mL
	10 mM	0.3756 mL	1.8779 mL	3.7557 mL	9.3893 mL
	15 mM	0.2504 mL	1.2519 mL	2.5038 mL	6.2595 mL
	20 mM	0.1878 mL	0.9389 mL	1.8779 mL	4.6947 mL
	25 mM	0.1502 mL	0.7511 mL	1.5023 mL	3.7557 mL
	30 mM	0.1252 mL	0.6260 mL	1.2519 mL	3.1298 mL
	40 mM	0.0939 mL	0.4695 mL	0.9389 mL	2.3473 mL
	50 mM	0.0751 mL	0.3756 mL	0.7511 mL	1.8779 mL
	60 mM	0.0626 mL	0.3130 mL	0.6260 mL	1.5649 mL
	80 mM	0.0469 mL	0.2347 mL	0.4695 mL	1.1737 mL
	100 mM	0.0376 mL	0.1878 mL	0.3756 mL	0.9389 mL

* Note: If you choose water as the stock solution, please dilute it to the working solution, then filter and sterilize it with a 0.22 μm filter before use.

Keywords

3-Deazaadenosine

32 Cited Publications

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3-Deazaadenosine

Cycloleucine

STM2457