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Deoxycytidine triphosphate (dCTP) 2056-98-6

Deoxycytidine triphosphate (dCTP) 2056-98-6

CAS No.: 2056-98-6

Deoxycytidine triphosphate (dCTP) is a nucleoside triphosphate that may be utilized in DNA synthesis. Deoxycytidine trip
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This product is for research use only, not for human use. We do not sell to patients.

Deoxycytidine triphosphate (dCTP) is a nucleoside triphosphate that may be utilized in DNA synthesis. Deoxycytidine triphosphate may be utilized in real-time PCR, cDNA synthesis and DNA sequencing research.

Physicochemical Properties


Molecular Formula C9H16N3O13P3
Molecular Weight 467.15704
Exact Mass 466.989
CAS # 2056-98-6
Related CAS # Deoxycytidine triphosphate trisodium salt;109909-44-6
PubChem CID 65091
Appearance White to off-white solid powder
Density 2.38 g/cm3
Boiling Point 811.5ºC at 760 mmHg
Flash Point 444.6ºC
Vapour Pressure 1.73E-30mmHg at 25°C
Index of Refraction 1.775
LogP -5.6
Hydrogen Bond Donor Count 6
Hydrogen Bond Acceptor Count 13
Rotatable Bond Count 8
Heavy Atom Count 28
Complexity 823
Defined Atom Stereocenter Count 3
SMILES

C1[C@@H]([C@H](O[C@H]1N2C=CC(=NC2=O)N)COP(=O)(O)OP(=O)(O)OP(=O)(O)O)O

InChi Key RGWHQCVHVJXOKC-SHYZEUOFSA-N
InChi Code

InChI=1S/C9H16N3O13P3/c10-7-1-2-12(9(14)11-7)8-3-5(13)6(23-8)4-22-27(18,19)25-28(20,21)24-26(15,16)17/h1-2,5-6,8,13H,3-4H2,(H,18,19)(H,20,21)(H2,10,11,14)(H2,15,16,17)/t5-,6+,8+/m0/s1
Chemical Name

[[(2R,3S,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen 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

Shipping Condition Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity


Targets - Deoxycytidine triphosphate (dCTP) acts as a competitive substrate targeting DNA polymerase, interfering with the incorporation of cytarabine triphosphate (Ara-CTP) into DNA [1]
ln Vitro The study examined the sensitivity of 13 cell lines that were produced from mouse lymphoma, myeloma, mastocytoma, and 1-β-D-arabinofuranosylcytosine (ara-C) to growth inhibition. The results showed that the cell lines varied by a factor of 100 between the most and least susceptible. It was shown that sensitivity and cellular deoxycytidine triphosphate (2′-Deoxycytidine-5′-triphosphate, dCTP) concentration were inversely connected. This suggests that if cells decrease their dCTP content while exposed to ara-C, their sensitivity may also decline. Boost. 1]. Phosphoethanolamine cytidylyltransferase uses deoxycytidine triphosphate trisodium salt as a substrate [2].
- In cultured L1210 mouse leukemia cells, treatment with thymidine (TdR) increased intracellular dCTP levels, which concentration-dependently reduced the cytotoxicity of cytarabine (Ara-C). At a TdR concentration of 10 μM, intracellular dCTP levels were significantly elevated, and the killing effect of Ara-C on L1210 cells was attenuated by approximately 50%. Removal of TdR restored dCTP levels to normal, and the sensitivity to Ara-C was recovered accordingly [1]
- In human cells (including normal peripheral blood lymphocytes and leukemia cells), dCTP is a key substrate for DNA synthesis, with its intracellular concentration maintained in dynamic equilibrium. dCTP levels were higher in certain leukemia cells than in normal lymphocytes. Exposure to chemotherapeutic drugs (e.g., antimetabolites) led to a significant decrease in dCTP levels, impairing DNA replication efficiency [3]
Cell Assay - Assay for L1210 cell sensitivity to Ara-C: L1210 mouse leukemia cells were seeded in culture plates and divided into control group, Ara-C alone group, and TdR (1-100 μM) pretreatment + Ara-C group. After 24-hour TdR pretreatment, different concentrations of Ara-C were added for further 48-hour culture. Cell survival was evaluated by cell counting or viability assay (e.g., trypan blue exclusion method) to analyze the effect of elevated dCTP levels on Ara-C cytotoxicity [1]
- Assay for deoxyribonucleoside triphosphates in human cells: Normal peripheral blood lymphocytes or leukemia cells were collected and lysed with ice-cold extraction buffer. The supernatant was obtained by centrifugation. Deoxyribonucleoside triphosphates in the extract, including dCTP, dATP, dGTP, and dTTP, were separated by high-performance liquid chromatography (HPLC). The intracellular concentration of each deoxyribonucleoside triphosphate was quantified based on retention time and peak area, comparing concentration differences between different cell types or after drug treatment [3]
References

[1]. Effect of thymidine on the sensitivity of cultured mouse tumor cells to 1-beta-D-arabinofuranosylcytosine. Cancer Res. 1979 Feb;39(2 Pt 1):538-41.

[2]. CTP:phosphoethanolamine cytidylyltransferase. Biochim Biophys Acta. 1997 Sep 4;1348(1-2):91-9.

[3]. Deoxyribonucleoside triphosphates in human cells: changes in disease and following exposure to drugs. Eur J Clin Invest. 1975 Apr;5(2):191-202.

Additional Infomation DCTP is a 2'-deoxycytidine phosphate having cytosine as the nucleobase. It has a role as a human metabolite, an Escherichia coli metabolite and a mouse metabolite. It is a 2'-deoxycytidine phosphate and a pyrimidine 2'-deoxyribonucleoside 5'-triphosphate. It is a conjugate acid of a dCTP(3-).
dCTP is a metabolite found in or produced by Escherichia coli (strain K12, MG1655).
Deoxycytidine 5'-triphosphate is a metabolite found in or produced by Escherichia coli (strain K12, MG1655).
2'-Deoxycytidine-5'-triphosphate has been reported in Homo sapiens, Bos taurus, and Apis cerana with data available.
dCTP is a metabolite found in or produced by Saccharomyces cerevisiae.
- Deoxycytidine triphosphate (dCTP) is an essential deoxyribonucleoside triphosphate substrate for DNA replication and repair, providing cytidine residues for DNA chain elongation [3]
- In cytarabine (Ara-C) chemotherapy, dCTP competes with Ara-CTP (the active metabolite of Ara-C) for binding to DNA polymerase. Intracellular dCTP levels directly affect the efficiency of Ara-CTP incorporation into DNA, thereby regulating the antitumor activity of Ara-C [1]
- The concentration of dCTP in human cells is jointly regulated by deoxyribonucleoside triphosphate synthases, kinases, and phosphatases. Abnormal levels (elevation or reduction) of dCTP may affect cell proliferation, DNA damage repair, and sensitivity to chemotherapeutic drugs [3]

Solubility Data


Solubility (In Vitro) H2O : ~50 mg/mL (~107.03 mM)
Solubility (In Vivo) Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

Injection Formulations
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300 :Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO 400 μLPEG300 50 μL Tween 80 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO 900 μL (20% SBE-β-CD in saline)]
*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.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300:Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL Saline)

Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).
Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders

Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.1406 mL 10.7030 mL 21.4059 mL
5 mM 0.4281 mL 2.1406 mL 4.2812 mL
10 mM 0.2141 mL 1.0703 mL 2.1406 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.