Synthesis of a biotin derivative of iberiotoxin: binding interactions with streptavidin and the BK Ca2+-activated K+ channel expressed in a human cell line

Bioconjug Chem. 2006 May-Jun;17(3):689-99. doi: 10.1021/bc060002u.

Abstract

Iberiotoxin (IbTx) is a scorpion venom peptide that inhibits BK Ca2+-activated K+ channels with high affinity and specificity. Automated solid-phase synthesis was used to prepare a biotin-labeled derivative (IbTx-LC-biotin) of IbTx by substitution of Asp19 of the native 37-residue peptide with N--(D-biotin-6-amidocaproate)-L-lysine. Both IbTx-LC-biotin and its complex with streptavidin (StrAv) block single BK channels from rat skeletal muscle with nanomolar affinity, indicating that the biotin-labeled residue, either alone or in complex with StrAv, does not obstruct the toxin binding interaction with the BK channel. IbTx-LC-biotin exhibits high affinity (KD = 26 nM) and a slow dissociation rate (koff = 5.4 x 10(-4) s(-1)) in a macroscopic blocking assay of whole-cell current of the cloned human BK channel. Titration of IbTx-LC-biotin with StrAv monitored by high performance size exclusion chromatography is consistent with a stoichiometry of two binding sites for IbTx-LC-biotin per StrAv tetramer, indicating that steric interference hinders simultaneous binding of two toxin molecules on each of the two biotin-binding faces of StrAv. In combination with fluorescent conjugates of StrAv or anti-biotin antibody, IbTx-LC-biotin was used to image the surface distribution of BK channels on a transfected cell line. Fluorescence microscopy revealed a patch-like surface distribution of BK channel protein. The results support the feasibility of using IbTx-LC-biotin and similar biotin-tagged K+ channel toxins for diverse applications in cellular neurobiology. .

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acid Sequence
  • Biotin / chemistry*
  • Cell Line
  • Electrophysiology
  • Humans
  • Large-Conductance Calcium-Activated Potassium Channels / chemistry*
  • Large-Conductance Calcium-Activated Potassium Channels / genetics
  • Large-Conductance Calcium-Activated Potassium Channels / metabolism*
  • Mass Spectrometry
  • Models, Molecular
  • Molecular Sequence Data
  • Patch-Clamp Techniques
  • Peptides / chemistry*
  • Peptides / pharmacology*
  • Potassium Channel Blockers / chemistry*
  • Potassium Channel Blockers / pharmacology
  • Protein Structure, Quaternary
  • Protein Structure, Tertiary
  • Streptavidin / chemistry*

Substances

  • Large-Conductance Calcium-Activated Potassium Channels
  • Peptides
  • Potassium Channel Blockers
  • Biotin
  • iberiotoxin
  • Streptavidin