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• W1967787350 abstract "We investigated water-soluble complexes of various ligands with the antiviral drugs, 9-[(2-hydroxyethoxy)methyl]guanine (acyclovir) and 9-[(1,3-dihydroxy-2-propoxy)methyl]guanine (DHPG). For comparison, we also examined the “parent” compounds, guanine and guanosine, as substrates for complex formation. Using the phase-solubility technique, we measured formation constant (K1) values at 23°C in pH 7 buffer. For a single substrate, formation constants with different ligands varied in the order: caffeine>pyridoxine ∼∼ cytidine>nicotinamide>sucrose. With caffeine as the ligand, formation constants with different substrates varied in the order: guanine>guanosine ∼∼ acyclovir>DHPG. The largest formation constant observed was 58 M−1 (for guanine-caffeine), and the smallest formation constant was 0.29 M−1 (for DHPG-sucrose). Examining the literature for formation constant data on compounds related to DHPG, and comparing literature data with our own, reveals a significant correlation between formation constants and ligand hydrophobicity. For 41 substrate-ligand pairs, least squares linear regression analysis of log K1 values versus various parameters reflecting donor-acceptor abilities (e.g., substrate and ligand HOMO and LUMO values, or substrate oxidation potentials) failed to significantly correlate. We conclude that ligand hydrophobicity is a general determinant of water soluble complex formation, but not necessarily the exclusive or dominant controlling factor for all complexes. Charge-transfer interactions are not important determinants of complex formation for the substrate-ligand combinations that we have considered." @default.
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• W1967787350 date "1986-07-01" @default.
• W1967787350 modified "2023-09-25" @default.
• W1967787350 title "Water Soluble Complexes of the Antiviral Drugs, 9-[(1,3-Dihydroxy-2-propoxy)Methyl]guanine and Acyclovir: The Role of Hydrophobicity in Complex Formation" @default.
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• W1967787350 doi "https://doi.org/10.1002/jps.2600750706" @default.
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