Name: 3-Deazaadenosine
Brand: GlpBio
SKU: GC14713
Availability: InStock
Rating: 5 (2 reviews)

GlpBio Products Cited In Reputable Papers

Nature
610.7931 (2022): 366-372

Nature
618, 1017–1023 (2023)

Cell
183.7 (2020): 1867-1883

Cell Research
31, 1291–1307 (2021)

Cell Research
33, 273–287 (2023)

Cell Research
33, 546–561 (2023)

Molecular Cancer
21.1 (2022): 1-17

Molecular Cancer
21.1 (2022): 1-18

Cancer Cell
39 (2021): 1-16

Cell Host Microbe
30.8 (2022): 1124-1138

Cell Host Microbe
31.5 (2023): 766-780

Cell Host Microbe
31.3 (2023): 418-43

Cell Metabolism
34.2 (2022): 240-255

Ann Rheum Dis
82(4): 533-545 (2023)

Cell Mol Immunol
20, 264–276 (2023)

Adv Funct Mater
33.35 (2023): 2214998

Product Documents

Quality Control & SDS

View current batch:

Purity: >98.00%

Protocol

Kinase experiment [1]:
Preparation Method	Prior to use, the [8-14C] adenosine was checked for purity using isocratic HPLC elution. The assay incubation mixture contained 0.4 IU of enzyme in 50 L. The metabolites were separated by thin-layer chromatography. The radioactivity was quantitated by cutting the plastic backed TLC plates and placing them in scintillation vials, and counting in a Packard 2000 CA scintillation counter
Applications	IC50: 0.15 (HIV-1, A012 isolate), 0.20 µM (HIV-1, A018 isolate). 3-Deazaadenosine (hydrochloride) is an inhibitor of S-adenosylhomocysteine hydrolase, with a Ki of 3.9 ?M.
Cell experiment [2]:
Cell lines	Mouse macrophage RAW 264.7
Preparation Method	RAW 264.7 cells were pretreated with or without 3-Deazaadenosine (100 μMM) for 1 h, and stimulated by the addition of LPS (1 μg/ml). After incubation for 1 h, the cells were washed, and p65 was recovered by immunoprecipitation with anti-p65 and protein A-Sepharose.
Reaction Conditions	0-100 μM 3-Deazaadenosine for 1 hour
Applications	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 ?M) enhances nuclear translocation of NF-κB, but blocks LPS-induced NF-κB transcriptional activity, and such inhibition is augmented by the addition of homocysteine.
Animal experiment [3]:
Animal models	Male, healthy Sprague–Dawley rats (300-350 g)
Preparation Method	Animals and balloon injury: rats were fed for 5 days prior and 14 days after the balloon injury with standard chow containing c3Ado at a concentration of 10 mg/kg 3-Deazaadenosine body weight.
Dosage form	10 mg/kg 3-Deazaadenosine for 5 days prior and 14 days after the balloon injury
Applications	3-deazaadenosine (c3Ado) inhibits atherogenesis in mice. Sprague Dawley rats underwent balloon angioplasty. C3Ado was administered orally, starting 5 days prior to the balloon injury and continued for 2 weeks. Fourteen days after balloon injury the intima/media ratio in the c3Ado-treated group was reduced by 67% and luminal stenosis by 50%. Neointimal cellular density was decreased by 25% and the induction of c-Jun and ki67 was markedly lower.
References: [1]. Gordon RK, Ginalski K, 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. doi: 10.1046/j.1432-1033.2003.03726.x. PMID: 12919315. [2]. Sedding DG, Trobs M, 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. doi: 10.1161/CIRCRESAHA.109.194357. Epub 2009 Apr 16. PMID: 19372464. [3]. Seeger FH, Hess W, et,al.The nucleotide analogue 3-deazaadenosine prevents neointima-formation after balloon injury. Biochem Biophys Res Commun. 2009 Jan 23;378(4):826-31. doi: 10.1016/j.bbrc.2008.11.151. Epub 2008 Dec 12. PMID: 19070587.

3-Deazaadenosine (hydrochloride) is an inhibitor of S-adenosylhomocysteine hydrolase, with a Ki of 3.9 µM^[1].

3-Deazaadenosine dose-dependently prevented the proliferation and migration of human coronary VSMCs in vitro. This was accompanied by an increased expression of the cyclin-dependent kinase inhibitors p21(WAF1/Cip1), p27(Kip1), a decreased expression of G(1)/S phase cyclins, and a lack of retinoblastoma protein hyperphosphorylation. [3]. In the mouse macrophage cell line, RAW264. S-Adenosylhomocysteine accumulated in cells incubated with 3-deazaaristeromycin while S-3-deazaadenosylhomocysteine was the major product in cells incubated with 3-Deazaadenosine and homocysteine thiolactone[4].200 microM 3-Deazaadenosine (c3Ado) prevented this TNF-induced increase in HEC adhesiveness. This effect resulted from interactions of 3-Deazaadenosine with HEC and not with polymorphonuclear neutrophils[5]. 3-Deazaadenosine (DZA), an adenosine analogue, prevented high methionine-induced ICAM-1 and VCAM-1 expression and collagen type-1 synthesis.in vitro 3-Deazaadenosine and CBS gene therapy successfully treated the HHcy-induced inflammatory reaction in the methionine metabolism pathway[6].

3-Deazaadenosine (c3Ado) inhibits atherogenesis in mice. Sprague Dawley rats underwent balloon angioplasty. 3-Deazaadenosine was administered orally, starting 5 days prior to the balloon injury and continued for 2 weeks. Fourteen days after balloon injury the intima/media ratio in the c3Ado-treated group was reduced by 67% and luminal stenosis by 50%. Neointimal cellular density was decreased by 25% and the induction of c-Jun and ki67 was markedly lower. Short-term administration of C3Ado inhibits neointima-formation in rats for at least 3 months after injury[7].

References:
[1]: Gordon RK, Ginalski K, 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. doi: 10.1046/j.1432-1033.2003.03726.x. PMID: 12919315.
[2]: Jeong SY, Ahn SG, 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. doi: 10.1074/jbc.274.27.18981. PMID: 10383397.
[3]: Sedding DG, TrÖbs M, 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. doi: 10.1161/CIRCRESAHA.109.194357. Epub 2009 Apr 16. PMID: 19372464.
[4]: Backlund PS Jr, Carotti D, et,al. Effects of the S-adenosylhomocysteine hydrolase inhibitors 3-deazaadenosine and 3-deazaaristeromycin on RNA methylation and synthesis. Eur J Biochem. 1986 Oct 15;160(2):245-51. doi: 10.1111/j.1432-1033.1986.tb09963.x. PMID: 3769925.
[5]: Jurgensen CH, Huber BE, et,al. 3-deazaadenosine inhibits leukocyte adhesion and ICAM-1 biosynthesis in tumor necrosis factor-stimulated human endothelial cells. J Immunol. 1990 Jan 15;144(2):653-61. PMID: 1967270.
[6]: Sen U, Tyagi N, et,al. Cystathionine-beta-synthase gene transfer and 3-deazaadenosine ameliorate inflammatory response in endothelial cells. Am J Physiol Cell Physiol. 2007 Dec;293(6):C1779-87. doi: 10.1152/ajpcell.00207.2007. Epub 2007 Sep 13. PMID: 17855772.
[7]: Seeger FH, Hess W, et,al. The nucleotide analogue 3-deazaadenosine prevents neointima-formation after balloon injury. Biochem Biophys Res Commun. 2009 Jan 23;378(4):826-31. doi: 10.1016/j.bbrc.2008.11.151. Epub 2008 Dec 12. PMID: 19070587.

Cas No.	6736-58-9	SDF
Synonyms	c3Ado, deazaAdo, 3-DZA
Chemical Name	(2R,3R,4S,5R)-2-(4-amino-1H-imidazo[4,5-c]pyridin-1-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
Canonical SMILES	NC1=C2C(N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)=CC=N1
Formula	C₁₁H₁₄N₄O₄	M.Wt	266.25
Solubility	≥ 26.6mg/mL in DMSO	Storage	Store at -20°C
General tips	Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month. To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition	Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table

Prepare stock solution
		1 mg	5 mg	10 mg
	1 mM	3.7559 mL	18.7793 mL	37.5587 mL
	5 mM	0.7512 mL	3.7559 mL	7.5117 mL
	10 mM	0.3756 mL	1.8779 mL	3.7559 mL

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Method for preparing DMSO master liquid: mg drug pre-dissolved in μL DMSO ( Master liquid concentration mg/mL, Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug. )

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3-Deazaadenosine (Synonyms: c3Ado, deazaAdo, 3-DZA)

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