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2,4-Diamino-6-hydroxypyrimidine

Cat No.:V30133 Purity: ≥98%
2,4-Diamino-6-hydroxypyrimidine is a specific inhibitor of GTP cyclohydrolase I, the rate-limiting enzyme in de novo protein synthesis.
2,4-Diamino-6-hydroxypyrimidine
2,4-Diamino-6-hydroxypyrimidine Chemical Structure CAS No.: 56-06-4
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
2,4-Diamino-6-hydroxypyrimidine is a specific inhibitor of GTP cyclohydrolase I, the rate-limiting enzyme in de novo protein synthesis. 2,4-Diamino-6-hydroxypyrimidine blocks the synthesis of Tetrahydrobiopterin (BH4) and inhibits NO production.
Biological Activity I Assay Protocols (From Reference)
ln Vitro
In response to food consumption, 2,4-Diamino-6-hydroxypyrimidine (DAHP) shows decreased generation of NO in chicken peritoneal macrophages (PEC) and the avian MC29 virus-transformed macrophage cell line HD11 [1]. In HUVEC cells, treatment with 2,4-Diamino-6-hydroxypyrimidine (DAHP; 5 mM; 24 h) dramatically lowered the amounts of BH4 and VCAM-1. 2,4-Diamino-6-hydroxypyrimidine (DAHP) was initially discovered as a biopterin framework for collagenous animal Crithidia fascicuLate growth stent[2]. It did this, at least in part, by suppressing NF-κB levels in HUVEC nuclei.
ln Vivo
Serotonin levels in the duodenum and blood vessels of mice treated with 2,4-diamino-6-hydroxypyrimidine (DAHP) at a dose of 3 g/kg/day for 4 days were roughly 46% and 40% of control levels, respectively. All organs tested, with the exception of the brain, showed a sharp decline in BH4 levels (T1/2 less than 12 hours) in response to 2,4-Diamino-6-hydroxypyrimidine. The levels of BH4 restored to normal less than 24 hours after the injection of 2,4-diamino-6-hydroxypyrimidine was stopped [3].
References

[1]. 2,4-Diamino-6-hydroxypyrimidine, an inhibitor of GTP cyclohydrolase I, suppresses nitric oxide production by chicken macrophages. Int J Immunopharmacol. 1994 Feb;16(2):101-8.

[2]. 2,4-Diamino-6-hydroxypyrimidine (DAHP) suppresses cytokine-induced VCAM-1 expression on the cell surface of human umbilical vein endothelial cells in a BH(4)-independent manner. Biochim Biophys Acta. Jul-Aug 2008;1780(7-8):960-5.

[3]. Gastrointestinal serotonin: depletion due to tetrahydrobiopterin deficiency induced by 2,4-diamino-6-hydroxypyrimidine administration. J Pharmacol Exp Ther. 1991 Feb;256(2):773-9.

Additional Infomation
2,4-Diamino-6-hydroxypyrimidine is a hydroxypyrimidine.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C4H6N4O
Molecular Weight
126.1166
Exact Mass
126.054
CAS #
56-06-4
Related CAS #
58470-85-2 (sulfate)
PubChem CID
135408763
Appearance
Off-white to light yellow solid powder
Density
1.6±0.1 g/cm3
Boiling Point
524.0±53.0 °C at 760 mmHg
Melting Point
285-286 °C (dec.)(lit.)
Flash Point
270.7±30.9 °C
Vapour Pressure
0.0±1.4 mmHg at 25°C
Index of Refraction
1.770
LogP
-1.29
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
0
Heavy Atom Count
9
Complexity
205
Defined Atom Stereocenter Count
0
InChi Key
SWELIMKTDYHAOY-UHFFFAOYSA-N
InChi Code
InChI=1S/C4H6N4O/c5-2-1-3(9)8-4(6)7-2/h1H,(H5,5,6,7,8,9)
Chemical Name
2,4-diamino-1H-pyrimidin-6-one
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: This product requires protection from light (avoid light exposure) during transportation and storage.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~16.67 mg/mL (~132.18 mM)
H2O : ~10 mg/mL (~79.29 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 1.67 mg/mL (13.24 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 16.7 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 1.67 mg/mL (13.24 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 16.7 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 1.67 mg/mL (13.24 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 16.7 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


Solubility in Formulation 4: 6.5 mg/mL (51.54 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 7.9290 mL 39.6448 mL 79.2896 mL
5 mM 1.5858 mL 7.9290 mL 15.8579 mL
10 mM 0.7929 mL 3.9645 mL 7.9290 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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