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| Targets |
2-O-Methylcytosine is an endogenous metabolite and a DNA/RNA synthesis-related compound. As a damaged nucleobase, its primary relevance is to DNA damage and mutagenesis. It can cause DNA mutation, resulting in various diseases such as cancer. Its presence in DNA can interfere with normal base pairing, leading to errors during replication and transcription.
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| ln Vitro |
DNA changes brought on by damaged nucleobases can result in a number of illnesses, including cancer [1].
In vitro, 2-O-methylcytosine is used in the study of DNA adducts, which are segments of DNA bound to a cancer-causing chemical. As a damaged nucleobase, its presence can be used to study the effects of DNA alkylation on replication and transcription. It serves as a model compound for understanding the biological consequences of DNA damage and repair mechanisms. |
| ln Vivo |
In vivo, 2-O-methylcytosine is an endogenous metabolite. Its formation in DNA can result from exposure to alkylating agents, and it is used as a biomarker for DNA damage. Its levels in biological samples can indicate exposure to certain carcinogens or the effectiveness of DNA repair pathways.
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| Enzyme Assay |
Non-cellular assays for 2-O-methylcytosine are primarily analytical. The compound is measured in DNA samples using highly sensitive techniques such as liquid chromatography-tandem mass spectrometry (LC-MS/MS) to quantify its levels as a marker of DNA damage. It can also be used in in vitro assays with DNA polymerases to study the effects of the modified base on replication fidelity and kinetics.
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| Cell Assay |
2-O-Methylcytosine is not typically used as a direct pharmacological agent in cellular assays. Instead, its effects are studied by introducing it into cellular DNA through treatment with alkylating agents or by using it as a standard for detecting DNA damage. Cellular assays may measure the cytotoxicity, mutagenicity, or the activation of DNA repair pathways in response to the formation of this DNA adduct.
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| Animal Protocol |
In vivo animal experiments with 2-O-methylcytosine are typically conducted to study the formation and repair of DNA adducts. Animals may be exposed to alkylating agents that generate this adduct, and its levels in various tissues are measured over time to assess DNA damage and repair kinetics. These models are used to study the carcinogenic potential of various compounds and to evaluate chemopreventive agents.
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| ADME/Pharmacokinetics |
2-O-Methylcytosine has a molecular weight of 125.13 and a molecular formula of C5H7N3O. Its pharmacokinetic properties are related to its role as a metabolite and a DNA adduct. As a metabolite, it is likely formed and cleared through normal metabolic pathways. It is typically stored as a powder at -20°C for up to 3 years or at 4°C for up to 2 years, and in solution at -80°C for 6 months or -20°C for 1 month.
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| Toxicity/Toxicokinetics |
The toxicological relevance of 2-O-methylcytosine stems from its role as a mutagenic DNA lesion. Its formation in DNA can lead to mutations, contributing to the development of cancer. It is not used as a therapeutic agent. Standard laboratory safety precautions should be followed when handling this compound, as it is a potential mutagen.
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| References | |
| Additional Infomation |
2-O-methylcytosine is a pyrimidine with a methoxy group substituted at the C-2 position and an amino group substituted at the C-4 position. It is a metabolite. It is an aminopyrimidine, an aromatic ether, and a methylcytosine. Functionally, it is related to cytosine.
2-O-Methylcytosine is an O-alkylated DNA adduct and a damaged nucleobase. It is an endogenous metabolite and a DNA/RNA synthesis-related compound. Its presence in DNA can cause mutations and is associated with diseases such as cancer. It is used in research to study DNA damage, repair, and mutagenesis. It is also known as 4-amino-2-methoxypyrimidine. |
| Molecular Formula |
C₅H₇N₃O
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|---|---|
| Molecular Weight |
125.13
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| Exact Mass |
125.058
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| CAS # |
3289-47-2
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| PubChem CID |
160679
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| Appearance |
White to off-white solid powder
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| Density |
1.2±0.1 g/cm3
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| Boiling Point |
294.4±32.0 °C at 760 mmHg
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| Melting Point |
167-171 °C
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| Flash Point |
131.9±25.1 °C
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| Vapour Pressure |
0.0±0.6 mmHg at 25°C
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| Index of Refraction |
1.567
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| LogP |
0.3
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
9
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| Complexity |
88.3
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
DHYLZDVDOQLEAQ-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C5H7N3O/c1-9-5-7-3-2-4(6)8-5/h2-3H,1H3,(H2,6,7,8)
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| Chemical Name |
2-methoxypyrimidin-4-amine
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| Synonyms |
2OMethylcytosine; 2 O Methylcytosine
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| HS Tariff Code |
2934.99.9001
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| 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)
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| Solubility (In Vitro) |
DMSO : ~60 mg/mL (~479.50 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 3 mg/mL (23.98 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 30.0 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: ≥ 3 mg/mL (23.98 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 30.0 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. View More
Solubility in Formulation 3: ≥ 3 mg/mL (23.98 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 7.9917 mL | 39.9584 mL | 79.9169 mL | |
| 5 mM | 1.5983 mL | 7.9917 mL | 15.9834 mL | |
| 10 mM | 0.7992 mL | 3.9958 mL | 7.9917 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.
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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