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Chemical Compound Review:

DHPA (2S)-3-(6-aminopurin-9- yl)propane-1,2-diol

Synonyms: CHEMBL494759, SureCN936286, AG-K-82531, KST-1A6019, AC1Q4VGK, ...

De Clercq, E. et al., de Clercq, E. et al., De Clercq, E. et al., Wingard, J.R. et al., Fojtová, M. et al., et al.

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Disease relevance of S-Dihydroxypropyladenine

(S)-9-(2,3-Dihydroxypropyl)adenine, a novel nucleoside analog, the sugar moiety of which is replaced by an aliphatic chain, inhibits the replication in vitro of several DNA and RNA viruses, including vaccinia, herpes simplex (types 1 and 2), measles, and vesicular stomatitis [1].
We have examined the toxicities of five antiviral agents showing activity against herpesviruses: vidarabine, acyclovir, (E)-5-(2-bromovinyl)-2'-deoxyuridine, trifluorothymidine, and (S)-9-(2,3-dihydroxypropyl)adenine [2].
In its activity against vesicular stomatitis virus, parainfluenza virus, measles and reo virus, C-c3 Ado proved about 100 times more potent than other established broad-spectrum antiviraL agents such as ribavirin (virazole) and (S)-DHPA ((S)-9-(2,3-dihydroxypropyl)adenine) [3].

High impact information on S-Dihydroxypropyladenine

In order to change the AdoHcy/AdoMet ratio (methylation index), (S)-9-(2,3-dihydroxypropyl)adenine was employed, a selective reversible inhibitor of cellular S-adenosyl-L-homocysteine hydrolase [4].
Inhibitory effect of a broad-spectrum antiviral agent, (S)-9-(2,3-dihydroxypropyl)adenine, on spermatogenesis in mice [5].

Analytical, diagnostic and therapeutic context of S-Dihydroxypropyladenine

Of a series of 58 aliphatic nucleoside analogues, (S)-9-(2,3-dihydroxypropyl)adenine [(S)-DHPA] proved to be the most active congener, when assayed for antiviral activity in primary rabbit kidney cell cultures challenged with either vaccinia or vesicular stomatitis virus [6].

References

(S)-9-(2,3-Dihydroxypropyl)adenine: an aliphatic nucleoside analog with broad-spectrum antiviral activity. De Clercq, E., Descamps, J., De Somer, P., Holý, A. Science (1978) [Pubmed]
Effect of several antiviral agents on human lymphocyte functions and marrow progenitor cell proliferation. Wingard, J.R., Hess, A.D., Stuart, R.K., Saral, R., Burns, W.H. Antimicrob. Agents Chemother. (1983) [Pubmed]
Broad-spectrum antiviral activity of the carbocyclic analog of 3-deazaadenosine. de Clercq, E., Montgomery, J.A. Antiviral Res. (1983) [Pubmed]
Evaluation of the impact of S-adenosylhomocysteine metabolic pools on cytosine methylation of the tobacco genome. Fojtová, M., Kovarík, A., Votruba, I., Holý, A. Eur. J. Biochem. (1998) [Pubmed]
Inhibitory effect of a broad-spectrum antiviral agent, (S)-9-(2,3-dihydroxypropyl)adenine, on spermatogenesis in mice. De Clercq, E., Leyten, R., Sobis, H., Matousek, J., Holý, A., De Somer, P. Toxicol. Appl. Pharmacol. (1981) [Pubmed]
Antiviral activity of aliphatic nucleoside analogues: structure-function relationship. De Clercq, E., Holy, A. J. Med. Chem. (1979) [Pubmed]

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