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The ionization constants and some divalent cation dissociation constants of nalidixic and oxolinic acids, both specific inhibitors of bacterial DNA replication, have been determined. The carboxylic pKa' values are 6.1 and 6.9 at 25 degrees for nalidixic and oxolinic acids, respectively. These values indicate that intramolecular hydrogen-bonding stabilizes the un-ionized form of these compounds in aqueous solution. Both compounds bind divalent cations; the divalent cation dissociation constants for oxolinic acid are somewhat smaller that those for nalidixic acid. We suggest that both compounds may act by forming a complex in situ with a divalent cation in a metalloprotein involved in DNA replication. The evidence that both drugs inhibit at the same target site is briefly reviewed.
K Timmers, and
R Sternglanz
January 1984,
Photochemistry and photobiology,
K Timmers, and
R Sternglanz
January 1974,
Urologiia i nefrologiia,
K Timmers, and
R Sternglanz
March 1978,
Antimicrobial agents and chemotherapy,
K Timmers, and
R Sternglanz
May 1977,
Die Pharmazie,
K Timmers, and
R Sternglanz
February 1980,
Experientia,
K Timmers, and
R Sternglanz
January 1974,
Folia microbiologica,
K Timmers, and
R Sternglanz
January 1996,
Journal of AOAC International,
K Timmers, and
R Sternglanz
May 1979,
Casopis lekaru ceskych,
K Timmers, and
R Sternglanz
December 1975,
Orvosi hetilap,
