Thymidine

CAS# 50-89-5

Thymidine

Catalog No. BCN5622----Order now to get a substantial discount!

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Chemical structure

Thymidine

3D structure

Chemical Properties of Thymidine

Cas No. 50-89-5 SDF Download SDF
PubChem ID 1134 Appearance Powder
Formula C10H14N2O5 M.Wt 242.2
Type of Compound Alkaloids Storage Desiccate at -20°C
Solubility DMSO : 50 mg/mL (206.42 mM; Need ultrasonic)
H2O : 33.33 mg/mL (137.60 mM; Need ultrasonic)
Chemical Name 1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
SMILES CC1=CN(C(=O)NC1=O)C2CC(C(O2)CO)O
Standard InChIKey IQFYYKKMVGJFEH-UHFFFAOYSA-N
Standard InChI InChI=1S/C10H14N2O5/c1-5-3-12(10(16)11-9(5)15)8-2-6(14)7(4-13)17-8/h3,6-8,13-14H,2,4H2,1H3,(H,11,15,16)
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Thymidine

The Cordyceps sinensis

Biological Activity of Thymidine

DescriptionThymidine is a pyrimidine nucleoside that is composed of the pyrimidine base thymine attached to the sugar deoxyribose. As a constituent of DNA, thymidine pairs with adenine in the DNA double helix. Thymidine could be a tracer in tumor cell examin. Thymidine overload due to Thymidine phosphorylase deficiency, and mitochondrial toxicity caused by antiviral Thymidine analogues.
TargetsDNA/RNA Synthesis
In vitro

In vitro assessment of 2-fluoro-2-deoxy-D-glucose, L-methionine and thymidine as agents to monitor the early response of a human adenocarcinoma cell line to radiotherapy.[Pubmed: 8478710]

J Nucl Med. 1993 May;34(5):773-9.


METHODS AND RESULTS:
The tumor cell uptake of three tracers that can be labeled with isotopes suitable for PET imaging--FDG, L-methionine and Thymidine--were examined in vitro in a human ovarian carcinoma cell line (HTB77IP3) at varying times following 30 Gy 60Co irradiation and were compared to a nonirradiated control group. FDG, methionine and Thymidine uptake per tissue culture well all increased following irradiation when compared to basal values, although to a much lower extent than the increases in uptake seen in a nonirradiated group. This increase in tracer uptake occurred despite a 6.25-fold decline in viable cell numbers. When examined per cell, FDG uptake per cell increased 9.77-fold, methionine 7.82-fold and Thymidine 9.48-fold over basal levels from Day 0 to Day 12 following irradiation. Part of these increases may be due to giant cell formation and/or radiation repair processes that require energy, protein and DNA substrates.
CONCLUSIONS:
While the in vitro system differs from in vivo systems due to the absence of a blood supply in vitro, a lack of infiltrating leukocytes and other factors, our data suggest that early assessment of human adenocarcinoma response to radiotherapy by PET with these tracers may be complicated by this normal increase in tracer uptake postirradiation. Clearly, in this human cancer cell line, early radiation-induced cell death is not associated with an early decline in tumor cell uptake of FDG, methionine or Thymidine.

Protocol of Thymidine

Kinase Assay

Thymidine kinase 2 enzyme kinetics elucidate the mechanism of thymidine-induced mitochondrial DNA depletion.[Pubmed: 25215937]

Biochemistry. 2014 Oct 7;53(39):6142-50.

Mitochondrial Thymidine kinase 2 (TK2) is a nuclear gene-encoded protein, synthesized in the cytosol and subsequently translocated into the mitochondrial matrix, where it catalyzes the phosphorylation of Thymidine (dT) and deoxycytidine (dC). The kinetics of Thymidine phosphorylation exhibits negative cooperativity, but dC phosphorylation follows hyperbolic Michaelis-Menten kinetics. The two substrates compete with each other in that Thymidine is a competitive inhibitor of dC phosphorylation, while dC acts as a noncompetitive inhibitor of Thymidine phosphorylation. In addition, TK2 is feedback inhibited by dTTP and dCTP. Thymidine kinase 2 also phosphorylates a number of pyrimidine nucleoside analogues used in antiviral and anticancer therapy and thus plays an important role in mitochondrial toxicities caused by nucleoside analogues. Deficiency in Thymidine kinase 2 activity due to genetic alterations causes devastating mitochondrial diseases, which are characterized by mitochondrial DNA (mtDNA) depletion or multiple deletions in the affected tissues. Severe Thymidine kinase 2 deficiency is associated with early-onset fatal mitochondrial DNA depletion syndrome, while less severe deficiencies result in late-onset phenotypes.
CONCLUSIONS:
In this review, studies of the enzyme kinetic behavior of Thymidine kinase 2 enzyme variants are used to explain the mechanism of mtDNA depletion caused by Thymidine kinase 2 mutations, Thymidine overload due to Thymidine phosphorylase deficiency, and mitochondrial toxicity caused by antiviral Thymidine analogues.

Thymidine Dilution Calculator

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Thymidine Molarity Calculator

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Preparing Stock Solutions of Thymidine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 4.1288 mL 20.6441 mL 41.2882 mL 82.5764 mL 103.2205 mL
5 mM 0.8258 mL 4.1288 mL 8.2576 mL 16.5153 mL 20.6441 mL
10 mM 0.4129 mL 2.0644 mL 4.1288 mL 8.2576 mL 10.322 mL
50 mM 0.0826 mL 0.4129 mL 0.8258 mL 1.6515 mL 2.0644 mL
100 mM 0.0413 mL 0.2064 mL 0.4129 mL 0.8258 mL 1.0322 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Thymidine

In vitro assessment of 2-fluoro-2-deoxy-D-glucose, L-methionine and thymidine as agents to monitor the early response of a human adenocarcinoma cell line to radiotherapy.[Pubmed:8478710]

J Nucl Med. 1993 May;34(5):773-9.

The tumor cell uptake of three tracers that can be labeled with isotopes suitable for PET imaging--FDG, L-methionine and Thymidine--were examined in vitro in a human ovarian carcinoma cell line (HTB77IP3) at varying times following 30 Gy 60Co irradiation and were compared to a nonirradiated control group. FDG, methionine and Thymidine uptake per tissue culture well all increased following irradiation when compared to basal values, although to a much lower extent than the increases in uptake seen in a nonirradiated group. This increase in tracer uptake occurred despite a 6.25-fold decline in viable cell numbers. When examined per cell, FDG uptake per cell increased 9.77-fold, methionine 7.82-fold and Thymidine 9.48-fold over basal levels from Day 0 to Day 12 following irradiation. Part of these increases may be due to giant cell formation and/or radiation repair processes that require energy, protein and DNA substrates. While the in vitro system differs from in vivo systems due to the absence of a blood supply in vitro, a lack of infiltrating leukocytes and other factors, our data suggest that early assessment of human adenocarcinoma response to radiotherapy by PET with these tracers may be complicated by this normal increase in tracer uptake postirradiation. Clearly, in this human cancer cell line, early radiation-induced cell death is not associated with an early decline in tumor cell uptake of FDG, methionine or Thymidine.

Thymidine kinase 2 enzyme kinetics elucidate the mechanism of thymidine-induced mitochondrial DNA depletion.[Pubmed:25215937]

Biochemistry. 2014 Oct 7;53(39):6142-50.

Mitochondrial Thymidine kinase 2 (TK2) is a nuclear gene-encoded protein, synthesized in the cytosol and subsequently translocated into the mitochondrial matrix, where it catalyzes the phosphorylation of Thymidine (dT) and deoxycytidine (dC). The kinetics of dT phosphorylation exhibits negative cooperativity, but dC phosphorylation follows hyperbolic Michaelis-Menten kinetics. The two substrates compete with each other in that dT is a competitive inhibitor of dC phosphorylation, while dC acts as a noncompetitive inhibitor of dT phosphorylation. In addition, TK2 is feedback inhibited by dTTP and dCTP. TK2 also phosphorylates a number of pyrimidine nucleoside analogues used in antiviral and anticancer therapy and thus plays an important role in mitochondrial toxicities caused by nucleoside analogues. Deficiency in TK2 activity due to genetic alterations causes devastating mitochondrial diseases, which are characterized by mitochondrial DNA (mtDNA) depletion or multiple deletions in the affected tissues. Severe TK2 deficiency is associated with early-onset fatal mitochondrial DNA depletion syndrome, while less severe deficiencies result in late-onset phenotypes. In this review, studies of the enzyme kinetic behavior of TK2 enzyme variants are used to explain the mechanism of mtDNA depletion caused by TK2 mutations, Thymidine overload due to Thymidine phosphorylase deficiency, and mitochondrial toxicity caused by antiviral Thymidine analogues.

Description

Thymidine, a specific precursor of deoxyribonucleic acid, is used as a cell synchronizing agent. Thymidine is a DNA synthesis inhibitor that can arrest cell at G1/S boundary, prior to DNA replication.

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