Nucleoside analogue

The antiviral drug aciclovir (bottom), a nucleoside analogue that functions by mimicking guanosine (top)

Nucleoside analogues are structural analogues of a nucleoside, which normally contain a nucleobase and a sugar. Nucleotide analogues are analogues of a nucleotide, which normally has one to three phosphates linked to a nucleoside. Both types of compounds can deviate from what they mimick in a number of ways, as changes can be made to any of the constituent parts (nucleobase, sugar, phosphate).[1] They are related to nucleic acid analogues.

Nucleoside and nucleotide analogues can be used in therapeutic drugs, including a range of antiviral products used to prevent viral replication in infected cells. The most commonly used is acyclovir.

Nucleotide and nucleoside analogues can also be found naturally. Examples include ddhCTP (3ʹ-deoxy-3′,4ʹdidehydro-CTP) produced by the human antiviral protein viperin[2] and sinefungin (a S-Adenosyl methionine analogue) produced by some Streptomyces.[3]

  1. ^ Seley-Radtke, KL; Yates, MK (June 2018). "The evolution of nucleoside analogue antivirals: A review for chemists and non-chemists. Part 1: Early structural modifications to the nucleoside scaffold". Antiviral Research. 154: 66–86. doi:10.1016/j.antiviral.2018.04.004. PMC 6396324. PMID 29649496.
  2. ^ Gizzi AS, Grove TL, Arnold JJ, Jose J, Jangra RK, Garforth SJ, et al. (June 2018). "A naturally occurring antiviral ribonucleotide encoded by the human genome". Nature. 558 (7711). Springer Science and Business Media LLC: 610–614. Bibcode:2018Natur.558..610G. doi:10.1038/s41586-018-0238-4. PMC 6026066. PMID 29925952.
  3. ^ Vedel, M; Lawrence, F; Robert-Gero, M; Lederer, E (14 November 1978). "The antifungal antibiotic sinefungin as a very active inhibitor of methyltransferases and of the transformation of chick embryo fibroblasts by Rous sarcoma virus". Biochemical and Biophysical Research Communications. 85 (1): 371–6. doi:10.1016/s0006-291x(78)80052-7. PMID 217377.