WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H122473
CAS#: 3690-10-6
Description: Zebularine is a nucleoside analog of cytidine.
Hodoodo Cat#: H122473
Name: Zebularine
CAS#: 3690-10-6
Chemical Formula: C9H12N2O5
Exact Mass: 228.07
Molecular Weight: 228.200
Elemental Analysis: C, 47.37; H, 5.30; N, 12.28; O, 35.05
Synonym: 4-Deoxyuridine; Pyrimidin-2-one ribonucleoside; Pyrimidin-2-one beta-ribofuranoside
IUPAC/Chemical Name: 1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one
InChi Key: RPQZTTQVRYEKCR-WCTZXXKLSA-N
InChi Code: InChI=1S/C9H12N2O5/c12-4-5-6(13)7(14)8(16-5)11-3-1-2-10-9(11)15/h1-3,5-8,12-14H,4H2/t5-,6-,7-,8-/m1/s1
SMILES Code: OC[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C=CC=NC2=O)O1
Appearance: To be determined
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: To be determined
Shelf Life: >2 years if stored properly
Drug Formulation: To be determined
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
More Info:
| Biological target: | |
| In vitro activity: | |
| In vivo activity: |
The following data is based on the product molecular weight 228.20 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
| Formulation protocol: | |
| In vitro protocol: | |
| In vivo protocol: |
1: Lai J, Fu Y, Tian S, Huang S, Luo X, Lin L, Zhang X, Wang H, Lin Z, Zhao H,
Lin S, Zhao J, Xu S, Li D, Cai S, Dong L, Qian J, Liang J, Li Q, Zhang Y, Fan J,
Balderas R, Chen Q. Zebularine elevates STING expression and enhances cGAMP
cancer immunotherapy in mice. Mol Ther. 2021 May 5;29(5):1758-1771. doi:
10.1016/j.ymthe.2021.02.005. Epub 2021 Feb 9. PMID: 33571681; PMCID: PMC8116609.
2: Zeng X, He G, Yang X, Xu G, Tang Y, Li H, Yu B, Wang Z, Xu W, Song K.
Zebularine protects against blood-brain-barrier (BBB) disruption through
increasing the expression of zona occludens-1 (ZO-1) and vascular endothelial
(VE)-cadherin. Bioengineered. 2022 Feb;13(2):4441-4454. doi:
10.1080/21655979.2021.2024323. PMID: 35112992; PMCID: PMC8974047.
3: Prochazkova K, Finke A, Tomaštíková ED, Filo J, Bente H, Dvořák P, Ovečka M,
Šamaj J, Pecinka A. Zebularine induces enzymatic DNA-protein crosslinks in 45S
rDNA heterochromatin of Arabidopsis nuclei. Nucleic Acids Res. 2022 Jan
11;50(1):244-258. doi: 10.1093/nar/gkab1218. PMID: 34904670; PMCID: PMC8754632.
4: Sass P, Sosnowski P, Kamińska J, Deptuła M, Skoniecka A, Zieliński J,
Rodziewicz-Motowidło S, Pikuła M, Sachadyn P. Examination of epigenetic
inhibitor zebularine in treatment of skin wounds in healthy and diabetic mice. J
Tissue Eng Regen Med. 2022 Dec;16(12):1238-1248. doi: 10.1002/term.3365. Epub
2022 Nov 9. PMID: 36350668.
5: Yoo CB, Cheng JC, Jones PA. Zebularine: a new drug for epigenetic therapy.
Biochem Soc Trans. 2004 Dec;32(Pt 6):910-2. doi: 10.1042/BST0320910. PMID:
15506921.
6: Kong J, Garcia V, Zehraoui E, Stammitti L, Hilbert G, Renaud C, Maury S,
Delaunay A, Cluzet S, Lecourieux F, Lecourieux D, Teyssier E, Gallusci P.
Zebularine, a DNA Methylation Inhibitor, Activates Anthocyanin Accumulation in
Grapevine Cells. Genes (Basel). 2022 Jul 15;13(7):1256. doi:
10.3390/genes13071256. PMID: 35886036; PMCID: PMC9316115.
7: Krzeminski P, García-Sanz R, Gutiérrez NC. Zebularine-induced myeloma cell
death is accompanied by decreased c-Myc expression. Cell Oncol (Dordr). 2020
Aug;43(4):743-750. doi: 10.1007/s13402-020-00516-6. Epub 2020 May 11. PMID:
32394351.
8: Marquez VE, Kelley JA, Agbaria R, Ben-Kasus T, Cheng JC, Yoo CB, Jones PA.
Zebularine: a unique molecule for an epigenetically based strategy in cancer
chemotherapy. Ann N Y Acad Sci. 2005 Nov;1058:246-54. doi:
10.1196/annals.1359.037. PMID: 16394141.
9: Yap ZH, Kong WY, Azeez AR, Fang CM, Ngai SC. Anti-Cancer Effects of
Epigenetics Drugs Scriptaid and Zebularine in Human Breast Adenocarcinoma Cells.
Anticancer Agents Med Chem. 2022;22(8):1582-1591. doi:
10.2174/1871520621666210608103251. PMID: 34102995.
10: Marquez VE, Barchi JJ Jr, Kelley JA, Rao KV, Agbaria R, Ben-Kasus T, Cheng
JC, Yoo CB, Jones PA. Zebularine: a unique molecule for an epigenetically based
strategy in cancer chemotherapy. The magic of its chemistry and biology.
Nucleosides Nucleotides Nucleic Acids. 2005;24(5-7):305-18. doi:
10.1081/ncn-200059765. PMID: 16247946.
11: Chen J, Li QY, Luo YH, Xiao EH. Continuous zebularine treatment enhances
hepatic differentiation of mesenchymal stem cells under liver-specific factors
induction in vitro. Life Sci. 2018 Dec 15;215:57-63. doi:
10.1016/j.lfs.2018.10.049. Epub 2018 Oct 25. PMID: 30473025.
12: Tang M, Lozano Hernandez L, Reginald-Opara JN, Svirskis D, Leung E, Wang H,
Wu Z. Zebularine suppressed gemcitabine-induced senescence and improved the
cellular and plasma pharmacokinetics of gemcitabine, augmented by liposomal co-
delivery. Int J Pharm. 2021 Jun 1;602:120659. doi:
10.1016/j.ijpharm.2021.120659. Epub 2021 Apr 30. PMID: 33933647.
13: Ye K, Wang S, Wang J, Han H, Ma B, Yang Y. Zebularine enhances apoptosis of
human osteosarcoma cells by suppressing methylation of ARHI. Cancer Sci. 2016
Dec;107(12):1851-1857. doi: 10.1111/cas.13088. Epub 2016 Dec 19. PMID: 27685841;
PMCID: PMC5198947.
14: Xiong X, Lan D, Li J, Zhong J, Zi X, Ma L, Wang Y. Zebularine and scriptaid
significantly improve epigenetic reprogramming of yak fibroblasts and cloning
efficiency. Cell Reprogram. 2013 Aug;15(4):293-300. doi: 10.1089/cell.2012.0092.
Epub 2013 Jun 22. PMID: 23790013.
15: Orta ML, Pastor N, Burgos-Morón E, Domínguez I, Calderón-Montaño JM, Huertas
Castaño C, López-Lázaro M, Helleday T, Mateos S. Zebularine induces replication-
dependent double-strand breaks which are preferentially repaired by homologous
recombination. DNA Repair (Amst). 2017 Sep;57:116-124. doi:
10.1016/j.dnarep.2017.07.002. Epub 2017 Jul 12. PMID: 28732309.
16: Luo YH, Chen J, Xiao EH, Li QY, Luo YM. Zebularine Promotes Hepatic
Differentiation of Rabbit Bone Marrow Mesenchymal Stem Cells by Interfering with
p38 MAPK Signaling. Stem Cells Int. 2018 Oct 10;2018:9612512. doi:
10.1155/2018/9612512. PMID: 30405726; PMCID: PMC6199887.
17: Koh ES, Kim S, Son M, Park JY, Pyo J, Kim WY, Kim M, Chung S, Park CW, Kim
HS, Shin SJ. The Protective Effect of Zebularine, an Inhibitor of DNA
Methyltransferase, on Renal Tubulointerstitial Inflammation and Fibrosis. Int J
Mol Sci. 2022 Nov 14;23(22):14045. doi: 10.3390/ijms232214045. PMID: 36430531;
PMCID: PMC9697081.
18: Dock H, Theodorsson A, Theodorsson E. DNA Methylation Inhibitor Zebularine
Confers Stroke Protection in Ischemic Rats. Transl Stroke Res. 2015
Aug;6(4):296-300. doi: 10.1007/s12975-015-0397-7. Epub 2015 Apr 1. PMID:
25824538.
19: Wang Q, Liang N, Yang T, Li Y, Li J, Huang Q, Wu C, Sun L, Zhou X, Cheng X,
Zhao L, Wang G, Chen Z, He X, Liu C. DNMT1-mediated methylation of BEX1
regulates stemness and tumorigenicity in liver cancer. J Hepatol. 2021
Nov;75(5):1142-1153. doi: 10.1016/j.jhep.2021.06.025. Epub 2021 Jul 1. PMID:
34217777.
20: Bryan JN, Kumar SR, Jia F, Balkin ER, Lewis MR. Zebularine significantly
sensitises MEC1 cells to external irradiation and radiopharmaceutical therapy
when administered sequentially in vitro. Cell Biol Int. 2014 Feb;38(2):187-97.
doi: 10.1002/cbin.10215. Epub 2013 Dec 9. PMID: 24323360; PMCID: PMC3947096.
