Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)

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Chemical Compound Review:

CHEMBL258513 2-amino-9-(4-hydroxybutyl)- 3H-purin-6-one

Synonyms: SureCN571645, AG-K-92596, CHEBI:530598, AC1L4PDG, AC1Q6IAR, ...

Larsson, A. et al., Ericson, A.C. et al., Larsson, A. et al., Larsson, A. et al.

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Disease relevance of AIDS097163

The inhibition of herpes simplex virus type 1 plaque formation by acyclovir, bromovinyldeoxyuridine, 9-(3,4-dihydroxybutyl)guanine, and 9-(4-hydroxybutyl)guanine at different thymidine concentrations was analyzed in Lineweaver-Burk plots [1].
A selective inhibition of HSV-1 DNA synthesis by 9-(4-hydroxybutyl)guanine was observed in infected Vero cells [2].
9-(4-Hydroxybutyl)guanine had a low cellular toxicity [2].

High impact information on AIDS097163

The extremely short half-life in plasma and the high clearance of 9-(4-hydroxybutyl)guanine as compared with those of (R)-9-(3,4-dihydroxybutyl)guanine probably made 9-(4-hydroxybutyl)guanine inefficacious when given intraperitoneally or orally to mice infected with herpesvirus [3].
Four acyclic guanosine analogs, the (R) and (S) enantiomers of 9-(3,4-dihydroxybutyl)guanine, 9-(4-hydroxybutyl)guanine, and acyclovir were compared in enzyme kinetic experiments, using purified herpes simplex virus type 2 thymidine kinase [4].
In cell cultures, different strains of herpes simplex virus type 1 (HSV-1) and type 2(HSV-2) were inhibited by 50% at 2-14 microM of 9-(4-hydroxybutyl)guanine, while a HSV-1 mutant lacking thymidine kinase (HSV-1 TK-) was resistant [2].

References

Kinetic analysis in cell culture of the reversal of antiherpes activity of nucleoside analogs by thymidine. Larsson, A., Brännström, G., Oberg, B. Antimicrob. Agents Chemother. (1983) [Pubmed]
Antiherpetic activity and mechanism of action of 9-(4-hydroxybutyl)guanine. Larsson, A., Alenius, S., Johansson, N.G., Oberg, B. Antiviral Res. (1983) [Pubmed]
Antiherpes effects and pharmacokinetic properties of 9-(4-hydroxybutyl) guanine and the (R) and (S) enantiomers of 9-(3,4-dihydroxybutyl)guanine. Ericson, A.C., Larsson, A., Aoki, F.Y., Yisak, W.A., Johansson, N.G., Oberg, B., Datema, R. Antimicrob. Agents Chemother. (1985) [Pubmed]
Phosphorylation of four acyclic guanosine analogs by herpes simplex virus type 2 thymidine kinase. Larsson, A., Tao, P.Z. Antimicrob. Agents Chemother. (1984) [Pubmed]

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