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Thymidine
 
 
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Thymidine (more precisely called deoxythymidine; can also be labelled deoxyribosylthymine, and thymine deoxyriboside) is a chemical compound
Chemical compound

A chemical compound is a Chemical substance consisting of two or more different chemical element Chemical bond together in a fixed mass ratio that can be split into simpler substances....
, more precisely a pyrimidine
Pyrimidine

Pyrimidine is a heterocyclic aromatic organic compound similar to benzene and pyridine, containing two nitrogen atoms at positions 1 and 3 of the six-member ring....
 deoxynucleoside. Deoxythymidine is the DNA
DNA

Deoxyribonucleic acid is a nucleic acid that contains the genetics instructions used in the development and functioning of all known living organisms and some viruses....
 nucleoside T, which pairs with deoxyadenosine
Deoxyadenosine

Deoxyadenosine is deoxyribonucleoside and is considered a Derivative of the nucleoside adenosine, differing from the latter by the replacement of a hydroxyl group by hydrogen at the Nucleic acid nomenclature position of its ribose sugar moiety....
 (A) in double-stranded DNA. In cell biology it is used to synchronize the cells in S phase.

Before the boom in thymidine use caused by the need for thymidine for the production of the antiretroviral drug
Antiretroviral drug

Antiretroviral drugs are medications for the treatment of infection by retroviruses, primarily HIV. When several such drugs, typically three or four, are taken in combination, the approach is known as highly active antiretroviral therapy, or HAART....
 azidothymidine (AZT), much of the world's thymidine production came from herring
Herring

Herring are small, oily fish of the genus Clupea found in the shallow, temperate waters of the North Pacific Ocean and the North Atlantic Ocean, including the Baltic Sea....
 sperm.
ts composition, deoxythymidine is a nucleoside
Nucleoside

Nucleosides are glycosylamines consisting of a nucleobase bound to a ribose or deoxyribose sugar. Examples of these include cytidine, uridine, adenosine, guanosine, thymidine and inosine....
 composed of deoxyribose
Deoxyribose

Deoxyribose, also known as D-Deoxyribose and 2-deoxyribose, is an aldopentose — a monosaccharide containing five carbon atoms, and including an aldehyde functional group in its linear structure....
 (a pentose sugar
Sugar

Sugar is a class of edible crystalline substances, mainly sucrose, lactose, and fructose. Human taste buds interpret its flavor as sweet. Sugar as a basic food carbohydrate primarily comes from sugar cane and from sugar beet, but also appears in fruit, honey, sorghum, sugar maple , and in many other sources....
) joined to the pyrimidine
Pyrimidine

Pyrimidine is a heterocyclic aromatic organic compound similar to benzene and pyridine, containing two nitrogen atoms at positions 1 and 3 of the six-member ring....
 base thymine
Thymine

Thymine is one of the four bases in the nucleic acid of DNA that make up the letters GCAT. The others are adenine, guanine, and cytosine. Thymine always pairs with adenine....
.

Deoxythymidine can be phosphorylated with one, two or three phosphoric acid groups, creating respectively dTMP, dTDP or dTTP ((deoxy)thymidine mono- di- or triphosphate).

It exists in solid
Solid

A solid object is in the states of matter characterized by resistance to deformation and changes of volume. In other words, it has high values both of Young's modulus and of shear modulus; this contrasts e.g....
 form as small white crystals or white crystalline powder
Powder (substance)

A powder is a dry, bulk solid composed of a large number of very fine particles that may flow freely when shaken or tilted. Powders are a special sub-class of granular materials, although the terms powder and granular are sometimes used to distinguish separate classes of material....
, has a molecular weight of 242.229 u, and has a melting point
Melting point

The melting point of a solid is the temperature range at which it changes states of matter from solid to liquid. At the melting point the solid and liquid phase exist in equilibrium....
 of 185 °C.






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Thymidine (more precisely called deoxythymidine; can also be labelled deoxyribosylthymine, and thymine deoxyriboside) is a chemical compound
Chemical compound

A chemical compound is a Chemical substance consisting of two or more different chemical element Chemical bond together in a fixed mass ratio that can be split into simpler substances....
, more precisely a pyrimidine
Pyrimidine

Pyrimidine is a heterocyclic aromatic organic compound similar to benzene and pyridine, containing two nitrogen atoms at positions 1 and 3 of the six-member ring....
 deoxynucleoside. Deoxythymidine is the DNA
DNA

Deoxyribonucleic acid is a nucleic acid that contains the genetics instructions used in the development and functioning of all known living organisms and some viruses....
 nucleoside T, which pairs with deoxyadenosine
Deoxyadenosine

Deoxyadenosine is deoxyribonucleoside and is considered a Derivative of the nucleoside adenosine, differing from the latter by the replacement of a hydroxyl group by hydrogen at the Nucleic acid nomenclature position of its ribose sugar moiety....
 (A) in double-stranded DNA. In cell biology it is used to synchronize the cells in S phase.

Before the boom in thymidine use caused by the need for thymidine for the production of the antiretroviral drug
Antiretroviral drug

Antiretroviral drugs are medications for the treatment of infection by retroviruses, primarily HIV. When several such drugs, typically three or four, are taken in combination, the approach is known as highly active antiretroviral therapy, or HAART....
 azidothymidine (AZT), much of the world's thymidine production came from herring
Herring

Herring are small, oily fish of the genus Clupea found in the shallow, temperate waters of the North Pacific Ocean and the North Atlantic Ocean, including the Baltic Sea....
 sperm.

Structure and properties

In its composition, deoxythymidine is a nucleoside
Nucleoside

Nucleosides are glycosylamines consisting of a nucleobase bound to a ribose or deoxyribose sugar. Examples of these include cytidine, uridine, adenosine, guanosine, thymidine and inosine....
 composed of deoxyribose
Deoxyribose

Deoxyribose, also known as D-Deoxyribose and 2-deoxyribose, is an aldopentose — a monosaccharide containing five carbon atoms, and including an aldehyde functional group in its linear structure....
 (a pentose sugar
Sugar

Sugar is a class of edible crystalline substances, mainly sucrose, lactose, and fructose. Human taste buds interpret its flavor as sweet. Sugar as a basic food carbohydrate primarily comes from sugar cane and from sugar beet, but also appears in fruit, honey, sorghum, sugar maple , and in many other sources....
) joined to the pyrimidine
Pyrimidine

Pyrimidine is a heterocyclic aromatic organic compound similar to benzene and pyridine, containing two nitrogen atoms at positions 1 and 3 of the six-member ring....
 base thymine
Thymine

Thymine is one of the four bases in the nucleic acid of DNA that make up the letters GCAT. The others are adenine, guanine, and cytosine. Thymine always pairs with adenine....
.

Deoxythymidine can be phosphorylated with one, two or three phosphoric acid groups, creating respectively dTMP, dTDP or dTTP ((deoxy)thymidine mono- di- or triphosphate).

It exists in solid
Solid

A solid object is in the states of matter characterized by resistance to deformation and changes of volume. In other words, it has high values both of Young's modulus and of shear modulus; this contrasts e.g....
 form as small white crystals or white crystalline powder
Powder (substance)

A powder is a dry, bulk solid composed of a large number of very fine particles that may flow freely when shaken or tilted. Powders are a special sub-class of granular materials, although the terms powder and granular are sometimes used to distinguish separate classes of material....
, has a molecular weight of 242.229 u, and has a melting point
Melting point

The melting point of a solid is the temperature range at which it changes states of matter from solid to liquid. At the melting point the solid and liquid phase exist in equilibrium....
 of 185 °C. The stability of deoxythymidine under standard temperature and pressure (STP) is very high.

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

Modified analogs of thymidine


Iododeoxyuridine
Iododeoxyuridine

5-Iododeoxyuridine is a nucleoside and a thymidine analogue abbreviated IUdR. IUdR is a radiosensitizer and increases the amount of DNA damage received from ionizing radiation....
 is a radiosensitizer and increases the amount of DNA damage received from ionizing radiation.

Azidothymidine (AZT) - used in the treatment of HIV
HIV

Human immunodeficiency virus is a lentivirus that can lead to AIDS , a condition in humans in which the immune system begins to fail, leading to life-threatening opportunistic infections....
 infection. AZT inhibits the process of reverse transcription
Reverse transcriptase inhibitor

Reverse transcriptase inhibitors are a class of antiretroviral drug used to treat HIV infection, tumors, and cancer. RTIs inhibit activity of reverse transcriptase, a viral DNA polymerase enzyme that retroviruses need to reproduce....
, a critical step in the viral life cycle
HIV

Human immunodeficiency virus is a lentivirus that can lead to AIDS , a condition in humans in which the immune system begins to fail, leading to life-threatening opportunistic infections....
.

Tritiated
Tritium

Tritium is a radioactive isotope of hydrogen. The atomic nucleus of tritium contains one proton and two neutrons, whereas the nucleus of Hydrogen atom contains one proton and no neutrons....
 thymidine 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.

Bromodeoxyuridine
Bromodeoxyuridine

Bromodeoxyuridine is a synthetic nucleoside that is an Analog of thymidine. BrdU is commonly used in the detection of proliferating cells in living tissues....
 (BrdU) is another thymidine analog that is often used for the detection of proliferating cells in living tissues.

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