Decitabine (NSC127716, 5AZA-CdR)
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.
- 1. Dandan Li, Lingyun Xia, et al. "A new high-throughput screening methodology for the discovery of cancer-testis antigen using multi-omics data." Comput Methods Programs Biomed. 2024 Jun:250:108193. PMID: 38678957
- 2. Lei Lv, Qinqin Wei, et al. "IGF2BP3 prevent HMGB1 mRNA decay in bladder cancer and development." Cell Mol Biol Lett. 2024 Mar 19;29(1):39. PMID: 38504159
- 3. 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
| 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. |
| Cell experiment [1]: | |
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Cell lines |
Human and murine melanoma cells (A375 and B16). |
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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. |
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Reaction Conditions |
Decitabine 0.5 μM added on Days 1 and 4 and images are obtained on Day 8. |
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Applications |
Decitabine decreases melanoma cell line proliferation and induces morphologic changes of differentiation. |
| Animal experiment [2]: | |
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Animal models |
Mice bearing U2OS xenografts. |
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Dosage form |
2.5 mg/kg intraperitoneally on Days 29, 31 and 33. On Day 37, mice are sacrificed. |
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Preparation method |
Dissolved in saline (0.9% w/v NaCl). |
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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]. |
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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. |
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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. |
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Quality Control & MSDS
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Chemical structure
