Tetrahydrouridine Chemical Properties

Melting point:

>195°C (dec.)

Boiling point:

668.6±55.0 °C(Predicted)

Density 

1.622±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,2-8°C

solubility 

Methanol (Slightly), Water (Slightly)

form 

Solid

pka

12.50±0.40(Predicted)

color 

White to Off-White

Water Solubility 

water: 200mg/mL

Stability:

Light Sensitive

Tetrahydrouridine Usage And Synthesis

Description

Tetrahydrouridine is a competitive, reversible inhibitor of cytidine deaminase (Ki values = 54 and 240 nM for human and E. coli enzymes, respectively).Its use, alone or in combination with the DNA methyltransferase inhibitor 5-fluoro-2'-deoxycytidine, is being evaluated in animal models and clinical trials for diseases, including cancer and mitochondrial DNA depletion syndrome.

Laboratory Procedures

Tetrahydrouridine is supplied as a crystalline solid. A stock solution may be made by dissolving the tetrahydrouridine in the solvent of choice. Tetrahydrouridine is soluble in organic solvents such as DMSO and dimethyl formamide, which should be purged with an inert gas. The solubility of tetrahydrouridine in these solvents is approximately 10 and 16 mg/ml, respectively.
Further dilutions of the stock solution into aqueous buffers or isotonic saline should be made prior to performing biological experiments. Ensure that the residual amount of organic solvent is insignificant, since organic solvents may have physiological effects at low concentrations. Organic solvent-free aqueous solutions of tetrahydrouridine can be prepared by directly dissolving the crystalline solid in aqueous buffers. The solubility of tetrahydrouridine in PBS, pH 7.2, is approximately 5 mg/ml. We do not recommend storing the aqueous solution for more than one day.

Description

Tetrahydrouridine is a competitive, reversible inhibitor of cytidine deaminase (K_i values = 54 and 240 nM for human and E. coli enzymes, respectively). Its use, alone or in combination with the DNA methyltransferase inhibitor 5-fluoro-2’-deoxycytidine, is being evaluated in animal models and clinical trials for diseases, including cancer and mitochondrial DNA depletion syndrome.

Uses

3,4,5,6-Tetrahydrouridine, is a derivative of Uridine (U829910). Tetrahydrouridine (THU), is a potent inhibitor of cytidine. It inhibits cell proliferation through cell cycle regulation regardless of cytidine deaminase expression levels deaminase (CDA), and thus can be used as a potential and promising treatment for tumors with highly expressed CDA.

in vivo

References

[1] B A CHABNER. Purification and properties of cytidine deaminase from normal and leukemic granulocytes.[J]. Journal of Clinical Investigation, 1974, 53 3: 922-931. DOI: 10.1172/jci107633
[2] R M COHEN  R W. Cytidine deaminase from Escherichia coli. Purification, properties and inhibition by the potential transition state analog 3,4,5,6-tetrahydrouridine.[J]. The Journal of Biological Chemistry, 1971, 246 24: 7561-7565.
[3] OSCAR ALCAZAR. Epigenetic regulation by decitabine of melanoma differentiation in vitro and in vivo?[J]. International Journal of Cancer, 2011, 131 1: 18-29. DOI: 10.1002/ijc.26320

Tetrahydrouridine(18771-50-1)Related Product Information

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