Transport of 5,5-diphenylbarbituric acid and its precursors and their effect on P-gp, MRP2 and CYP3A4 in Caco-2 and LS180 cells

Eur J Pharm Sci. 2011 Jan 18;42(1-2):19-29. doi: 10.1016/j.ejps.2010.10.001. Epub 2010 Oct 16.

Abstract

Aim: To examine the transport of 5,5-diphenylbarbituric acid sodium (T2007) and its mono- (MMMDPB) and di- (T2000) methoxymethylated precursors and their inducibility potential in Caco-2 and LS180 cells.

Methods: Transport studies of T2000, MMMDPB and T2007 in Caco-2 cells were performed in Transwells. P-gp and CYP3A4 activities were assayed by [(3)H]digoxin and rhodamine 123 cellular retention and testosterone 6β-hydroxylation, respectively. Expressions of PXR, VDR and CAR mRNA and CYP3A4, MDR1/P-gp and MRP2 mRNA and protein were determined by qPCR and Western blotting, respectively. PXR siRNA was used to assess the involvement of PXR.

Results: The P(app(A→B))s and P(app(B→A))s of T2000, MMMDPB and T2007 were similar (30-35×10(-6)cm/s) in Caco-2 cells. Treatment for 3 days with T2000 (15μM), MMMDPB (70μM) and T2007 (300μM) generally furnished a greater induction in LS180 cells over the Caco-2 cells due to the higher, natural abundance of PXR. Changes in expression were confined mostly to MDR1 and CYP3A4: in LS180 cells, treatment for 3 days increased MDR1 and CYP3A4 but not MRP2 mRNA, and elevated P-gp and CYP3A4 protein expression that led to decreased cellular accumulation of [(3)H]digoxin and rhodamine 123, and enhanced testosterone 6β-hydroxylase activity towards T2007, respectively. The silencing of PXR by PXR siRNA in LS180 cells significantly attenuated the induction of MDR1 and CYP3A4.

Conclusions: T2000, MMMDPB, and T2007 exhibited high permeabilities but are not P-gp substrates. T2007 and its analogs upregulated CYP3A4 and MDR1 modestly via the PXR.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • ATP Binding Cassette Transporter, Subfamily B, Member 1 / metabolism*
  • Biological Transport
  • Biotransformation
  • Blotting, Western
  • Caco-2 Cells
  • Cell Culture Techniques
  • Cell Membrane Permeability
  • Chromatography, High Pressure Liquid
  • Constitutive Androstane Receptor
  • Cytochrome P-450 CYP3A / metabolism*
  • Humans
  • Intestinal Absorption
  • Intestinal Mucosa / metabolism
  • Molecular Structure
  • Multidrug Resistance-Associated Protein 2
  • Multidrug Resistance-Associated Proteins / metabolism*
  • Phenobarbital / analogs & derivatives*
  • Phenobarbital / chemistry
  • Phenobarbital / metabolism
  • Phenobarbital / pharmacokinetics
  • Pregnane X Receptor
  • Prodrugs / chemistry
  • Prodrugs / metabolism
  • Prodrugs / pharmacokinetics*
  • RNA, Small Interfering / genetics
  • Receptors, Calcitriol / genetics
  • Receptors, Cytoplasmic and Nuclear / genetics*
  • Receptors, Steroid / genetics
  • Reverse Transcriptase Polymerase Chain Reaction
  • Transfection

Substances

  • ABCC2 protein, human
  • ATP Binding Cassette Transporter, Subfamily B, Member 1
  • Constitutive Androstane Receptor
  • Multidrug Resistance-Associated Protein 2
  • Multidrug Resistance-Associated Proteins
  • Pregnane X Receptor
  • Prodrugs
  • RNA, Small Interfering
  • Receptors, Calcitriol
  • Receptors, Cytoplasmic and Nuclear
  • Receptors, Steroid
  • 5,5-diphenylbarbituric acid
  • Cytochrome P-450 CYP3A
  • CYP3A4 protein, human
  • Phenobarbital