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Timidina

Timidina
Identificadores
Número CAS 50-89-5
PubChem 1134
UNII VC2W18DGKR
DrugBank DB04485
MeSH Thymidine
ChEMBL CHEMBL52609
Imaxes 3D Jmol Image 1
Propiedades
Fórmula molecular C10H14N2O5
Masa molar 242,23 g mol−1

Se non se indica outra cousa, os datos están tomados en condicións estándar de 25 °C e 100 kPa.

A timidina, que tamén se pode denominar con máis precisión desoxitimidina (porque leva desoxirribosa), é un nucleósido coa fórmula C10H14N2O5 formado pola base nitroxenada pirimidínica timina unida por enlace N-glicosídico ao azucre 2-desoxirribosa.

Cando leva un fosfato unido en posición 5' convértese no nucleótido dTMP, que forma parte do ADN. No ARNt pode aparecer no bucle ou brazo T en forma de ribotimidina (con ribosa).

A timidina úsase en bioloxía celular para sincronizar o ciclo celular das células na fase S.

Tradicionalmente obtíñase a timidina do esperma do arenque, pero despois do seu incremento de produción para fabricar AZT utilizáronse técnicas de enxeñaría xenética[1][2].

Propiedades

En forma sólida aparece como pequenos cristias brancos ou pos cristalinos, ten un peso molecular de 242,229 d, e un punto de fusión de 185 °C. A súa estabilidade é alta en condicións estándar de presión e temperatura.

Non é tóxica e como parte dun dos nucleótidos do ADN aparece de forma natural en todos os organismos vivos e virus de ADN. Aínda que o seu nome debería ser desoxitimidina, úsase case sempre o de timidina, xa que como aparece fundamentalmente formando parte dos nucleótidos do ADN e alí leva sempre a desoxirribosa, non hai necesidade de distinguir. O ARN en vez de nucleótidos coa base nitroxenada timina, leva nucleótidos coa base uracilo (unida a ribosa), pero só se diferencian nun grupo metilo, polo que a base timina pode chamarse tamén 5-metiluracilo.

Análogos e derivados da timidina

A iododesoxiuridina é un radiosensibilizador que incrementa a cantidade de danos que sofre o ADN cando recibe radiación ionizante.

A azidotimidina (AZT) úsase como fármaco para o tratamento contra a infección por VIH. O AZT é un inhibidor da transcrición inversa, que é unha fase crítica na replicación dese virus.

A timidina tritiada úsase en ensaios de proliferación celular. A timidina incorpórase ás células en división e o nivel de incorporación, medido usando un contador de escintilacións líquido, é proporcional á intensidade da proliferación celular [3].

A bromodesoxiuridina (BrdU) é un análogo da timidina que se usa a miúdo para a detección de células en proliferación en tecidos vivos.

Notas

  1. ↑ Hyeon Cheon Lee; et al. Fermentative production of thymidine by a metabolically engeneered Escherichia coli strain. Arquivado dende o orixinal o 18 de setembro de 2019. Consultado o 14 de xullo de 2011. [1] Arquivado 18 de setembro de 2019 en Wayback Machine.
  2. ↑ Makoto Ishii, Hideyuki Shirae, Kenzo Yokozeko. Enzymatic Production of 5-Methyluridine from Purine Nucleosides and Thymine by Erwinia carotovora AJ-2992. Agricultural and Biological Chemistry. 
  3. ↑ Haugland, R. (2005). Assays for Cell Viability, Proliferation, and Function. In: The Handbook: A Guide to Fluorescent Probes and Labeling Technologies, 10th ed. USA: Invitrogen Corp. pp. . 699–776. 

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