A1906-10mg | Decitabine (NSC127716, 5AZA-CdR) [2353-33-5] Clinisciences

Background

Decitabine is a kind of deoxycytidine analog and an inducer of cellular differentiation. It is able to incorporate into DNA and form irreversible covalent bonds with DNA-methyltransferases at cytosine sites targeted for DNA methylation by increasing γ-globin expression through a posttranscriptional mechanism independent of DNA methylation. Decitabine has been shown substantial efficacy in reactivating epigenetically silenced tumor suppressor genes in vitro. In colon cancer cell lines, decitabine can increase the histone H3-lysine 9 acetylation: methylation ratio at the unmethylated hMLH1 and MGMT promoters in HCT116 and RKO cells, respectively. In T24 bladder cancer cells, decitabine can increase histone H3-lysine 9 acetylation and histone H3-lysine 4 methylation at the unmethylated p14 promoter.

Reference

Carlo Stresemann, Frank Lyko. Modes of action of the DNA methyltransferase inhibitors azacytidine and decitabine. International Journal of Cancer. 2008; 123 (1): 8-13.

Jean-Pierre J. Issa, Guillermo Garcia-Manero, Francis J. Giles, Rajan Mannari, Deborah Thomas, Stefan Faderl, Emel Bayar, John Lyons, Craig S. Rosenfeld, Jorge Cortes, and Hagop M. Kantarjian. Phase 1 study of low-dose prolonged exposure schedules of the hypomethylating agent 5-aza-2’-deoxycytidine (decitabine) in hematopoietic malignancies. Blood. 2004; 103 (5): 1635-40.

Hagop Kantarjian, Yasuhiro Oki, Guillermo Garcia-Manero, Xuelin Huang, Susan O’Brien, Jorge Cortes, Stefan Faderl, Carlos Bueso-Ramos, Farhad Ravandi, Zeev Estrov, Alessandra Ferrajoli, William Wierda, Jianqin Shan, Jan Davis,

Francis Giles, Hussain I. Saba, and Jean-Pierre J. Issa. Results of a randomized study of 3 schedules of low-dose decitabine in higher-risk myelodysplastic syndrome and chronic myelomonocytic leukemia. Blood. 2007; 109 (1): 52-57.

Stuart A. Scotta, Wei-Feng Donga, Calley Hirscha, David Sheridana, Stephen E. Sanchea, C. Ronald Geyera, John F. DeCoteau. 5-Aza-2-deoxycytidine (decitabine) can relieve p21WAF1 repression in human acute myeloid leukemia by a mechanism involving release of histone deacetylase 1 (HDAC1) without requiring p21WAF1 promoter demethylation. Leukemia Research. 2006; 30 (1): 69-76.

Product Citation

1. Dandan Li, Lingyun Xia, et al. "Serine protease PRSS56, a novel cancer-testis antigen activated by DNA hypomethylation, promotes colorectal and gastric cancer progression via PI3K/AKT axis." Cell Biosci. 2023 Jul 3;13(1):124. PMID: 37400936

Chemical Properties

Physical Appearance	A solid
Storage	Store at -20°C
M.Wt	228.08
Cas No.	2353-33-5
Formula	C₈H₁₂N₄O₄
Synonyms	5-Aza-2'-deoxycytidine; Decitabine
Solubility	insoluble in EtOH; ≥11.4 mg/mL in DMSO; ≥23.3 mg/mL in H2O with gentle warming
Chemical Name	4-amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3,5-triazin-2-one
SDF	Download SDF
Canonical SMILES	C1C(C(OC1N2C=NC(=NC2=O)N)CO)O
Shipping Condition	Small Molecules with Blue Ice, Modified Nucleotides with Dry Ice.
General tips	We do not recommend long-term storage for the solution, please use it up soon.

Protocol

Cell experiment [1]:
Cell lines	Human and murine melanoma cells (A375 and B16).
Preparation method	The solubility of this compound in DMSO is >10 mM. General tips for obtaining a higher concentration: Please warm the tube at 37°C for 10 minutes and/or shake it in the ultrasonic bath for a while. Stock solution can be stored below -20°C for several months.
Reaction Conditions	Decitabine 0.5 μM added on Days 1 and 4 and images are obtained on Day 8.
Applications	Decitabine decreases melanoma cell line proliferation and induces morphologic changes of differentiation.
Animal experiment [2]:
Animal models	Mice bearing U2OS xenografts.
Dosage form	2.5 mg/kg intraperitoneally on Days 29, 31 and 33. On Day 37, mice are sacrificed.
Preparation method	Dissolved in saline (0.9% w/v NaCl).
Applications	Decitabine significantly reduces tumor xenograft size and lowers mitotic activity, increases the amount of apoptotic cells and bone matrix production. Decitabine also increases the expression of GADD45A, HSPA9B, PAWR, PDCD5, NFKBIA, and TNFAIP3 to ≥2-fold, which are pro-apoptotic genes [2].
Other notes	Please test the solubility of all compounds indoor, and the actual solubility may slightly differ with the theoretical value. This is caused by an experimental system error and it is normal.
References: [1] Alcazar O, Achberger S, Aldrich W, et al. Epigenetic regulation by decitabine of melanoma differentiation in vitro and in vivo. Int J Cancer, 2012, 131 (1): 18-29. [2] Al-Romaih K, Somers GR, Bayani J, et al. Modulation by decitabine of gene expression and growth of osteosarcoma U2OS cells in vitro and in xenografts: identification of apoptotic genes as targets for demethylation. Cancer Cell Int, 2007, 7: 14.

Quality Control

Purity = 99.77%

Chemical structure

Decitabine (NSC127716, 5AZA-CdR) [2353-33-5]

Référence A1906-10mg

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