Thymidine CAS No. 50-89-5

Product Description

Thymidine, also known as deoxythymidine, is a pyrimidine deoxynucleoside that consists of the nucleobase thymine linked to the sugar deoxyribose via a β-N₁-glycosidic bond. It is a crucial component of DNA, pairing specifically with adenine through hydrogen bonds. Thymidine is phosphorylated to form thymidine monophosphate (TMP), thymidine diphosphate (TDP), and thymidine triphosphate (TTP), the latter of which is incorporated into DNA during replication. In biological research, thymidine is used to study DNA replication, with analogs like bromodeoxyuridine (BrdU) employed to track cell proliferation. It also has significant applications in medicine, particularly in the development of antiviral and anticancer drugs. For instance, AZT (zidovudine) is a thymidine analog used in HIV treatment. Unlike uridine, which is found in RNA, thymidine contains deoxyribose instead of ribose and thymine instead of uracil. Thymidine plays a vital role in DNA synthesis, repair, and cell cycle synchronization. Elevated levels of thymidine kinase 1 (TK1) are associated with fast-dividing cells, including cancer cells, making it a potential biomarker for various cancers. However, high doses of thymidine or its analogs can lead to side effects such as gastrointestinal issues, hepatotoxicity, and bone marrow suppression.

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Product Use & Characteristics

• Molecular Formula: C₁₀H₁₄N₂O₅

• Molecular Weight: 242.23 g/mol

• IUPAC Name: 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione

• Chemical Structure:

  • Base: Thymine (a pyrimidine derivative)

  • Sugar: 2'-Deoxyribose

• Function:

  • Serves as a building block for DNA synthesis.

  • Forms phosphorylated forms such as Thymidine Monophosphate (TMP), Thymidine Diphosphate (TDP), and Thymidine Triphosphate (TTP), which is incorporated into DNA during replication.

  • Involved in DNA repair mechanisms.

  • Used in cell cycle synchronization, particularly in the G1/early S phase of the cell cycle.

Uses

• Cell Biology and Research:

  • Studying DNA replication using thymidine analogs like bromodeoxyuridine (BrdU) and 5-ethynyl-2'-deoxyuridine (EdU) to track cell proliferation.

  • Radiolabeled thymidine (e.g., tritiated thymidine, 3H-TdR) is used to measure cell proliferation and DNA synthesis.

• Medical Applications:

  • Antiviral drugs: Thymidine analogs like azidothymidine (AZT) are used in HIV treatment.

  • Anticancer drugs: Thymidine analogs like fluorothymidine (FLT) and 5-fluorouracil (5-FU) are used as chemotherapeutic agents to inhibit DNA synthesis in cancer cells.

  • Biomarker: Elevated levels of thymidine kinase 1 (TK1) are associated with fast-dividing cells, including cancer cells, making it a potential diagnostic and prognostic biomarker for various cancers.

  • Metabolic modulation: Thymidine is explored in combination with other chemotherapy drugs to protect normal cells from toxicity or enhance anti-tumor effects.

• Genetic Disorders:

  • Mutations in enzymes involved in thymidine metabolism, such as thymidine kinase 2 (TK2), can lead to mitochondrial DNA depletion syndromes.

Synthesis Methods

• Phosphorylation:

  • Thymidine is phosphorylated to form thymidine monophosphate (TMP), thymidine diphosphate (TDP), and thymidine triphosphate (TTP).

  • Thymidine triphosphate (dTTP) is incorporated into DNA during replication.

• Synthesis of Analogues:

  • Thymidine analogs like AZT (zidovudine) are synthesized for use in antiviral treatments.

  • Other analogs like BrdU, EdU, and FLT are synthesized for research and medical applications.

Biological Role

• DNA Building Block:

  • Thymidine is one of the four essential nucleosides that make up DNA, pairing specifically with adenine through two hydrogen bonds.

  • Forms deoxythymidine triphosphate (dTTP), a direct building block used during DNA synthesis and replication.

• DNA Repair:

  • Involved in DNA repair mechanisms.

• Cell Cycle Synchronization:

  • Commonly used in cell biology research to synchronize cells in the G1/early S phase of the cell cycle, which is when DNA synthesis begins.

Potential Side Effects

• High Doses or Altered Metabolism:

  • Gastrointestinal issues (nausea, vomiting, diarrhea, abdominal pain)

  • Hepatotoxicity (liver damage)

  • Electrolyte imbalance

  • Central nervous system toxicity

  • Bone marrow aplasia (suppression of blood cell production)

• Genetic Disorders:

  • Thymidine phosphorylase (TP) deficiency can lead to mitochondrial neurogastrointestinal encephalomyopathy (MNGIE syndrome), characterized by severe gastrointestinal dysfunction, muscle weakness, and neurological deterioration.

• Thymidine Analog Drugs:

  • Side effects of thymidine analog drugs like trifluridine and tipiracil include low white blood cell counts, anemia, bleeding problems, fatigue, and hair loss.

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Qingdao Sigma Chemical Co., Ltd., established in January 2017 and headquartered in Qingdao, China, is a reliable chemical supplier. Specializing in pharmaceuticals, biochemical intermediates, and research chemicals, the company offers a diverse product portfolio, including peptides (e.g., Tirzepatide, Semaglutide), nootropics, veterinary products, and APIs, often marketed with ≥99% purity and COA certification. We provides R&D, custom synthesis, and contract manufacturing services at various scales, while claiming a global export presence across 100+ countries. With international warehouses in the USA, Europe, Australia, and Canada, Qingdao Sigma Chemical also facilitates drop-shipping and reshipments, positioning itself as a key supplier for laboratory and research applications.