Thymidine

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Thymidine
Desoxythymidin.svg
Thymidine 3D ball.png
Names
IUPAC name
Thymidine
Systematic IUPAC name
1-[(2R,4S,5R)-4-Hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4(1H,3H)-dione
Other names
deoxythymidine; doxribtimine; Td; dT; 1-[(2R,4S,5R)-4-Hydroxy-5-(hydroxymethyl)tetrahydrofur-2-yl]-5-methyl-1,3-dihydropyrimidine-2,4-dione
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.065 OOjs UI icon edit-ltr-progressive.svg
MeSH Deoxythymidine
PubChem CID
UNII
  • 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)/t6-,7+,8+/m0/s1
    Key: IQFYYKKMVGJFEH-XLPZGREQSA-N
  • InChI=1/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)/t6-,7+,8+/m0/s1
    Key: IQFYYKKMVGJFEH-XLPZGREQBQ
  • Cc1cn(c(=O)[nH]c1=O)[C@H]2C[C@@H]([C@H](O2)CO)O
Properties
C10H14N2O5
Molar mass 242.231 g·mol−1
Melting point 185 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Thymidine (symbol dT or dThd), also known as deoxythymidine is a pyrimidine deoxynucleoside. Deoxythymidine is the DNA nucleoside T, which pairs with deoxyadenosine (A) in double-stranded DNA. In cell biology it is used to synchronize the cells in G1/early S phase.[ not in body ] The prefix deoxy- is often left out since there are no precursors of thymine nucleotides involved in RNA synthesis.

Before the boom in thymidine use caused by the need for thymidine in the production of the antiretroviral drug azidothymidine (AZT), much of the world's thymidine production came from herring sperm. [1] Thymidine occurs almost exclusively in DNA but it also occurs in the T-loop of tRNA.[ not in body ]

Chemistry

In its composition, deoxythymidine is a nucleoside composed of deoxyribose (a pentose sugar) joined to the pyrimidine base thymine.

Deoxythymidine can be phosphorylated with one, two or three phosphoric acid groups, creating dTMP (deoxythymidine monophosphate), dTDP, or dTTP (for the di- and tri- phosphates, respectively).

It exists in solid form as small white crystals or white crystalline powder. It has a molecular weight of 242.229 Da and a melting point of 185 °C. The stability of deoxythymidine under standard temperature and pressure (STP) is very high.

Function

Deoxythymidine is non-toxic and is part of one of the four nucleosides in DNA. It is a naturally occurring compound that exists in all living organisms and DNA viruses. Instead of thymidine, RNA contains uridine (uracil joined to ribose). Uracil is chemically very similar to thymine, which is also known as 5-methyluracil. Since thymine nucleotides are precursors of DNA (but not RNA), the prefix "deoxy" is often left out; i.e., deoxythymidine is often just called thymidine.

Clinical significance

Thymidine is listed as a chemical teratogen. [2]

Medical use

As a pharmaceutical drug, deoxythymidine is known by the international nonproprietary name doxribtimine. [3] Doxribtimine is a component of the medication doxecitine/doxribtimine used for the treatment of thymidine kinase 2 deficiency. [4]

Derivatives with diagnostic or therapeutic applications

Radiolabeled thymidine (TdR), such as tritiated thymidine (3H-TdR), is commonly used in cell proliferation assays. The thymidine is incorporated into dividing cells and the level of this incorporation, measured using a liquid scintillation counter, is proportional to the amount of cell proliferation. For example, lymphocyte proliferation can be measured this way in lymphoproliferative disorders.

Iododeoxyuridine is a radiosensitizer and increases the amount of DNA damage received from ionizing radiation.

Azidothymidine (AZT) – used in the treatment of HIV infection. AZT inhibits the process of reverse transcription, a critical step in the viral life cycle.

Bromodeoxyuridine (BrdU) is another thymidine analog that is often used for the detection of proliferating cells in living tissues.

5-Ethynyl-2´-deoxyuridine (EdU) is a thymidine analog which is incorporated into the DNA of dividing cells and is used to assay DNA synthesis in cell culture or living tissues. It can be visualized by covalently binding a fluorescent azide using click chemistry, which is less harsh than the conditions used to expose the epitope for BrdU antibodies.

Edoxudine is an antiviral drug.

Telbivudine (β-L-2′-deoxythymidine, LdT) is the unmodified "unnatural" L-enantiomer of thymidine that was used in the treatment of chronic hepatitis B. [5]

Thymidine imbalance

During growth of bacteriophage T4, an excess of thymidine availability increases mutation. [6] [7] A deficiency of thymidine during growth also increases mutation. [6] A thymidylate auxotroph of the diploid yeast Saccharomyces cerevisiae was grown under conditions in which thymidyate levels varied from excess to depletion. [8]

References

  1. ↑ Ishii M, Shirae H, Yokozeki K (1989). "Enzymatic Production of 5-Methyluridine from Purine Nucleosides and Thymine by Erwinia carotovora AJ-2992". Agricultural and Biological Chemistry. 53 (12): 3209–3218. doi:10.1080/00021369.1989.10869860.
  2. ↑ The following list of chemicals known or believed to be teratogens is drawn primarily from Sax NI, Lewis RJ. Dangerous Properties of Industrial Materials (7th ed.).
  3. ↑ World Health Organization (2022). "International nonproprietary names for pharmaceutical substances (INN): recommended INN: list 87". WHO Drug Information. 36 (1). hdl: 10665/352794 .
  4. ↑ "FDA approves 1st drug for thymidine kinase 2 deficiency". U.S. Food and Drug Administration. 3 November 2025. Retrieved 4 November 2025.PD-icon.svg This article incorporates text from this source, which is in the public domain .
  5. ↑ Gosselin G, Pierra C, Benzaria-Prad S, Dukhan D, Cretton-Scott E, Standring D, et al. (2008). "LDT (Telbivudine) as a potent and specific nucleoside analogue (Tyzeka™, Sebivo™) for the treatment of chronic hepatitis B". Collection Symposium Series. pp. 244–248. doi:10.1135/css200810244. ISBN   978-80-86241-29-6.
  6. 1 2 Bernstein C, Bernstein H, Mufti S, Strom B (October 1972). "Stimulation of mutation in phage T 4 by lesions in gene 32 and by thymidine imbalance". Mutation Research. 16 (2): 113–119. doi:10.1016/0027-5107(72)90171-6. PMID   4561494.
  7. ↑ DeVries JK, Wallace SS (1982). "Reversion of bacteriophage T4rII mutants by high levels of pyrimidine deoxyribonucleosides". Molecular & General Genetics. 186 (1): 101–105. doi:10.1007/BF00422919. PMID   7050620.
  8. ↑ Eckardt F, Kunz BA, Haynes RH (September 1983). "Variation of mutation and recombination frequencies over a range of thymidylate concentrations in a diploid thymidylate auxotroph". Current Genetics. 7 (5): 399–402. doi:10.1007/BF00445881. PMID   24173422.
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