| Size | Price | Stock | Qty |
|---|---|---|---|
| 50μg |
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| Other Sizes |
| Targets |
Human Endogenous Metabolite Microbial Metabolite
No direct pharmacological target; endogenous metabolite and substrate for DNA polymerases, nucleoside diphosphate kinases, and enzymes in nucleotide metabolism. Converted to dADP by adenylate kinase, then to dATP by nucleoside diphosphate kinase. dATP is active substrate for DNA polymerases. Also substrate for deoxyadenosine deaminase (converted to dIMP) and involved in purine nucleotide metabolism. |
|---|---|
| ln Vitro |
In Caco-2 cells, 2′-Deoxyadenosine 5′-monophosphate (dAMP) is absorbed in a time-dependent fashion. A decrease in pH causes an increase in the absorption of 2′-Deoxyadenosine 5′-monophosphate, indicating that the protons may be involved in the transport activity of this compound. The absorption of 2′-Deoxyadenosine 5′-monophosphate by Caco-2 cells is dependent on both pH and Na+ [1].
Endogenous metabolite, purine deoxyribonucleotide, building block for DNA. Substrate for DNA polymerases during replication and repair, can influence cellular signaling through its metabolites. Used to study adenosine-based interactions during DNA synthesis and DNA damage. Critical intermediate in de novo and salvage pathways of purine nucleotide synthesis; levels tightly regulated for dNTP pools. |
| ln Vivo |
No specific in vivo data; endogenous metabolite involved in DNA synthesis/repair in all living cells. Perturbations in dAMP metabolism (adenylate kinase, deoxyadenosine deaminase, or ribonucleotide reductase deficiency) lead to DNA damage, cell cycle arrest, and immune dysfunction. Measurement of dAMP and metabolites used as biomarkers of DNA damage, nucleotide pool imbalance, and metabolic disorders (e.g., adenosine deaminase deficiency causing SCID).
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| Enzyme Assay |
(1) Nucleotide monophosphate kinase assay: incubate recombinant adenylate kinase (0.1-1 ug) with dAMP (0.5-5 mM), ATP (1-5 mM) in 50 mM Tris-HCl pH7.5, 5 mM MgCl2 at 37degC for 10-30 min. (2) Quantify dADP by HPLC-UV at 260 nm or LC-MS/MS. (3) DNA polymerase activity: incorporate radiolabeled dATP (from dAMP phosphorylation) into DNA using DNA polymerase and template-primer, measure by scintillation counting.
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| Cell Assay |
(1) Seed HeLa or HEK293 cells (5×10⁵/well) in 6-well plates. (2) For nucleotide labeling: add 3H- or 14C-dAMP (0.1-1 uCi/mL) for 1-6 h. (3) Harvest, extract with 80% ice-cold methanol or 0.4M perchloric acid. (4) Separate nucleotides by HPLC (ion-exchange or reverse-phase with ion pairing) or TLC. (5) Quantify radiolabeled dAMP, dADP, dATP by radiometric detection or LC-MS/MS. (6) For DNA damage: treat cells with H2O2, UV, etoposide, then measure dAMP and dATP by LC-MS/MS. (7) Cell viability: treat with dAMP 0.1-10 mM for 48 h, MTT; non-toxic up to 5 mM.
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| Animal Protocol |
(1) For PK: use 6-8 week old male C57BL/6 mice (20-25 g) or SD rats (200-250 g). (2) Administer dAMP by IV (10-50 mg/kg) or IP (25-100 mg/kg) in sterile saline/PBS pH7.0-7.4. (3) Collect blood at 0,0.25,0.5,1,2,4,8,12,24 h, plasma deproteinized with 3 vol ice-cold methanol. (4) Analyze dAMP and metabolites (dA, dADP, dATP) by LC-MS/MS. (5) Tissue distribution: collect liver, kidney, small intestine, spleen at 0.5-4 h, homogenize, extract, analyze. (6) For excretion: collect 24-h urine. (7) For nucleotide pool perturbation: treat mice with methotrexate (20 mg/kg IP) to inhibit dTMP synthesis, then administer dAMP (50-200 mg/kg IP), measure dATP/dGTP pools in bone marrow and intestinal mucosa.
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| ADME/Pharmacokinetics |
Soluble in water (≥50 mg/mL) and 0.1M HCl. For cell culture, dissolve directly or prepare 20-100 mM stock in water, adjust pH to 7.0-7.4 with NaOH, filter sterilize. For in vivo, dissolve in sterile saline or PBS at 10-50 mg/mL. Storage: powder at -20degC for 3 years; solution at -20degC for 6 months, -80degC for 1 year. Stable at neutral pH, hydrolyzes under acidic conditions.
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| Toxicity/Toxicokinetics |
dAMP is an endogenous nucleotide, non-toxic at physiological concentrations (low uM in cells). In vitro: CCK-8 on HEK293 cells with dAMP 1-20 mM, 48 h, IC50 >10 mM. In vivo: acute IP LD50 in mice ~2000-3000 mg/kg. High doses (>500 mg/kg IP) cause mild GI upset and transient diarrhea. No significant hepatotoxicity, nephrotoxicity, or neurotoxicity. For research only.
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| References |
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| Additional Infomation |
2'-Deoxyadenosine 5'-monophosphate is a purine 2'-deoxynucleoside 5'-monophosphate with the nucleobase adenine. It is an important metabolite. It is both a purine 2'-deoxynucleoside 5'-monophosphate and a 2'-deoxyadenosine 5'-phosphate. It is the conjugate acid of 2'-deoxyadenosine 5'-monophosphate (2-). Deoxyadenosine monophosphate is a metabolite found in or produced by Escherichia coli (strains K12 and MG1655). It has been reported to exist in Homo sapiens, Leishmania megacephala, and other organisms with relevant data. dAMP is a metabolite found in or produced by Saccharomyces cerevisiae.
2'-Deoxyadenosine-5'-monophosphate (dAMP) is a naturally occurring purine deoxyribonucleotide found in DNA. Formed by de novo purine biosynthesis (from IMP to AMP, then to dADP/dATP via ribonucleotide reductase) or by salvage pathway (phosphorylation of deoxyadenosine by deoxyadenosine kinase). dAMP is phosphorylated to dADP and dATP, the latter a substrate for DNA polymerases. Regulated by 5'-nucleotidase (dephosphorylation to deoxyadenosine) and adenylate kinase (conversion to dADP). Not a drug; strictly for research in nucleotide metabolism, DNA replication/repair, and analytical method development. |
| Molecular Formula |
C10H14N5O6P
|
|---|---|
| Molecular Weight |
331.22
|
| Exact Mass |
331.068
|
| CAS # |
653-63-4
|
| Related CAS # |
2′-Deoxyadenosine 5′-monophosphate disodium;2922-74-9;2'-Deoxyadenosine-5'-monophosphate-d12 dilithium;2'-Deoxyadenosine-5'-monophosphate-15N5,d12 dilithium;2'-Deoxyadenosine-5'-monophosphate-15N5 dilithium;2'-Deoxyadenosine-5'-monophosphate-13C10 dilithium;2'-Deoxyadenosine-5'-monophosphate-13C10,15N5 dilithium;2483830-51-7
|
| PubChem CID |
12599
|
| Appearance |
White to off-white solid powder
|
| Density |
2.2±0.1 g/cm3
|
| Boiling Point |
753.5±70.0 °C at 760 mmHg
|
| Melting Point |
148 °C
|
| Flash Point |
409.5±35.7 °C
|
| Vapour Pressure |
0.0±2.7 mmHg at 25°C
|
| Index of Refraction |
1.867
|
| LogP |
-1.23
|
| Hydrogen Bond Donor Count |
4
|
| Hydrogen Bond Acceptor Count |
10
|
| Rotatable Bond Count |
4
|
| Heavy Atom Count |
22
|
| Complexity |
452
|
| Defined Atom Stereocenter Count |
3
|
| SMILES |
C1[C@@H]([C@H](O[C@H]1N2C=NC3=C(N=CN=C32)N)COP(=O)(O)O)O
|
| InChi Key |
KHWCHTKSEGGWEX-RRKCRQDMSA-N
|
| InChi Code |
InChI=1S/C10H14N5O6P/c11-9-8-10(13-3-12-9)15(4-14-8)7-1-5(16)6(21-7)2-20-22(17,18)19/h3-7,16H,1-2H2,(H2,11,12,13)(H2,17,18,19)/t5-,6+,7+/m0/s1
|
| Chemical Name |
[(2R,3S,5R)-5-(6-aminopurin-9-yl)-3-hydroxyoxolan-2-yl]methyl dihydrogen phosphate
|
| 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 (In Vitro) |
DMSO :~250 mg/mL (~754.79 mM)
|
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (6.28 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 20.8 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: ≥ 2.08 mg/mL (6.28 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 20.8 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: ≥ 2.08 mg/mL (6.28 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 | 3.0191 mL | 15.0957 mL | 30.1914 mL | |
| 5 mM | 0.6038 mL | 3.0191 mL | 6.0383 mL | |
| 10 mM | 0.3019 mL | 1.5096 mL | 3.0191 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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