3690-10-6 Usage
Description
Zebularine (3690-10-6) is an orally active DNA methyltransferase inhibitor, characterized as a cytidine analogue, cytidine deaminase inhibitor, and DNA demethylating agent. It possesses the ability to inhibit tumor cell proliferation, re-activate silenced genes in certain cancer cells, and induce differentiation of mesenchymal stem cells into cardiomyocytes. Zebularine is presented as a white solid and has garnered interest for its potential applications in various fields.
Uses
Used in Pharmaceutical Applications:
Zebularine is used as an anticancer agent for its ability to inhibit tumor cell proliferation and re-activate silenced genes in T24 bladder carcinoma cells. Its role as a cytidine deaminase inhibitor and DNA demethylating agent makes it a promising candidate for cancer treatment.
Used in Stem Cell Differentiation:
Zebularine is used as a differentiation agent for its capacity to induce differentiation of mesenchymal stem cells into cardiomyocytes, which could have significant implications for regenerative medicine and the treatment of heart-related conditions.
Used in Epigenetic Research:
As a DNA methyltransferase inhibitor, Zebularine is used in research to study the role of DNA methylation in various biological processes and diseases, including cancer and other genetic disorders.
Used in Drug Development:
Zebularine's properties as a cytidine analogue and inhibitor of cytidine deaminase make it a valuable compound in the development of new drugs targeting these pathways for therapeutic purposes.
Biological Activity
Orally active DNA methyltransferase inhibitor. Inhibits tumor cell proliferation (IC 50 = 120 μ M) and re-activates silenced genes in T24 bladder carcinoma cells. Also inhibits cytidine deaminase (K i ~ 2 μ M).
Biochem/physiol Actions
Zebularine is a cytidine analogue, cytidine deaminase inhibitor, and DNA demethylating agent.
Check Digit Verification of cas no
The CAS Registry Mumber 3690-10-6 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,6,9 and 0 respectively; the second part has 2 digits, 1 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 3690-10:
(6*3)+(5*6)+(4*9)+(3*0)+(2*1)+(1*0)=86
86 % 10 = 6
So 3690-10-6 is a valid CAS Registry Number.
InChI:InChI=1/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
3690-10-6Relevant articles and documents
MUTUAL PRODRUG COMPRISING SHORT CHAIN FATTY ACIDS AND ZEBULARINE OR 1'-CYANO-CYTARABINE FOR CANCER TREATMENT
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Page/Page column 21; 22, (2015/06/03)
The present invention provides mutual prodrugs comprising anti-cancer nucleosides and short chain fatty acids; methods for production of the mutual prodrugs; methods of treatment comprising administration of the mutual prodrugs; and pharmaceutical composi
Formation of a β-pyrimidine nucleoside by a free pyrimidine base and ribose in a plausible prebiotic reaction
Bean, Heather D.,Sheng, Yinghong,Collins, James P.,Anet, Frank A. L.,Leszczynski, Jerzy,Hud, Nicholas V.
, p. 9556 - 9557 (2008/02/11)
The problem of β-nucleoside formation under prebiotic conditions represents one of the most significant challenges to the RNA world hypothesis and to many of its proposed precursors. The possibility exists that alternative bases may have come before the contemporary bases (i.e., A, G, C, and U), including bases that more readily form nucleosides. In a search for pyrimidine bases that are able to form nucleosides in plausible prebiotic reactions, it was discovered that the drying and heating of 2-pyrimidinone with ribose produces a β-furanosyl ribonucleoside in approximately 12% yield. At least two other chemical isomers of zebularine are also produced in the condensation reaction. This work represents the first successful synthesis of a pyrimidine nucleoside from a free base and a nonactivated sugar in a plausible prebiotic reaction. A comparison of 2-pyrimidinone with the purine bases that have also been demonstrated to form nucleosides in plausible prebiotic reactions provides insights regarding what chemical features of the bases facilitate glycoside formation in drying-heating reactions. Copyright
A New Synthesis of 3-(β-D-Ribofuranosyl)uracil (Isouridine) via the Intermediacy of a O6,5'-Cyclotetrahydropyrimidinone Nucleoside
Rao, Kambhampati V. B.,Marquez, Victor E.,Kelley, James A.,Corcoran, Mary T.
, p. 127 - 130 (2007/10/02)
A specific and efficient synthesis for 3-(β-D-ribofuranosyl)uracil, isouridine (1), has been devised.Starting with the easily accessible 1-(β-D-ribofuranosyl)-1,2-dihydropyrimidin-2-one (3b) the C-6 carbonyl function of isouridine was built via formation
