Transporter-mediated effects of diclofenamic acid and its ascorbyl pro-drug in the in vivo neurotropic activity of ascorbyl nipecotic acid conjugate

J Pharm Sci. 2004 Jan;93(1):78-85. doi: 10.1002/jps.10532.

Abstract

Continuing our studies on SVCT2 ascorbic acid (AA) transporter-mediated drug delivery of neurotropic agents, we have now investigated the in vitro intracellular uptake of Diclofenac (Diclo) and its conjugate (AA-Diclo), both characterized by high affinity for the SVCT2 transporter. We have also investigated the in vivo uptake mechanism of AA-conjugate of Nipecotic acid (AA-Nipec) and the implication of the transporter-mediated effects of Diclo and AA-Diclo. Diclo resulted as a noncompetitive inhibitor of AA transport, but also showed a sodium-dependent and ascorbate-independent uptake, thus implying the possible involvement of specific transporters in the delivery to the brain of Diclo. This result opens a perspective in the discovery of new strategies in the targeting of this drug to the brain. Inhibitory effects of Diclo and AA-Diclo on the SVCT2 transporter were used to study anticonvulsant effects of AA-Nipec, confirming our hypothesis of an SVCT2-mediated transport in its neurotropic activity. AA-Diclo stability has been also investigated: it is hydrolyzed following a first-order kinetics in buffer, plasma (t(1/2) at about 10 h) and whole blood (t(1/2) at about 3 h), suggesting AA-Diclo as a potential candidate to enhance the short half-life of Diclo in vivo.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Animals
  • Ascorbic Acid / pharmacokinetics*
  • Ascorbic Acid / therapeutic use
  • Brain / metabolism
  • Cell Line
  • Diclofenac / pharmacokinetics*
  • Diclofenac / therapeutic use
  • Humans
  • Male
  • Mice
  • Nipecotic Acids / pharmacokinetics*
  • Nipecotic Acids / therapeutic use
  • Organic Anion Transporters, Sodium-Dependent / metabolism*
  • Prodrugs / pharmacokinetics*
  • Prodrugs / therapeutic use
  • Seizures / chemically induced
  • Seizures / prevention & control
  • Sodium-Coupled Vitamin C Transporters
  • Symporters / metabolism*

Substances

  • Nipecotic Acids
  • Organic Anion Transporters, Sodium-Dependent
  • Prodrugs
  • SLC23A2 protein, human
  • Slc23a2 protein, mouse
  • Sodium-Coupled Vitamin C Transporters
  • Symporters
  • Diclofenac
  • nipecotic acid
  • Ascorbic Acid