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Activity against human immunodeficiency virus (HIV) in the naphthalenesulphonic acid series is most pronounced in the disulphonic acid series. In this class of compounds, N-acyl derivatives of 4-amino-5-hydroxy-2,7-naphthalenedisulphonic acid demonstrate significant anti-HIV activity at non-toxic doses. The most potent compounds in this group of agents are bis naphthalenedisulphonic acids. A bis derivative containing a decamethylene spacer demonstrated activity against HIV-1, HIV-2 giant cell formation and reverse transcriptase (RT). This compound also demonstrated an in vitro therapeutic index (ratio of 50% cytotoxic concentration to 50% inhibitory antiviral concentration) of 10.6. Molecular modelling analyses of this agent, suramin, and several suramin analogues were undertaken to explain the potent anti-HIV-1 RT activity. These studies were carried out using the molecular decomposition/recomposition strategy, conformational searching, energy minimization and molecular dynamics (MD) simulation. The bis naphthalenedisulphonic acid derivative compound 1, having a flexible decamethylene spacer, was shown to be able to mimic the helical twist of the B-DNA backbone as a low energy conformer state.

antiviral chemistry and chemotherapy

Naphthalenesulphonic Acid Derivatives as Potential anti-HIV-1 Agents. Chemistry, Biology and Molecular Modelling of Their Inhibition of Reverse Transcriptase