[(125)I]-N-[(3-azido-5-iodo)benzyl]dantrolene and [(125)I]-N-[[3-iodo-5-(3-trifluoromethyl-3H-diazirin-3-yl)]benzyl]dantrolene: photoaffinity probes specific for the physiological Ca(2+) release from sarcoplasmic reticulum of skeletal muscle

Bioorg Med Chem Lett. 2002 Nov 18;12(22):3263-5. doi: 10.1016/s0960-894x(02)00701-1.

Abstract

In order to capture and identify key molecules that regulate the release of Ca(2+) from the sarcoplasmic reticulum (SR) of skeletal muscle, we designed specific photoaffinity probes based on the structural modification of dantrolene. Thus, GIF-0082 and GIF-0276 possessing azido- and trifluoromethyldiazirinyl-benzyl groups, respectively, at the hydantoin moiety were found to have a highly selective inhibitory effect on physiological Ca(2+) release (PCR) without affecting Ca(2+)-induced Ca(2+) release (CICR). Successful realization of the sharp discrimination between PCR and CICR has led to the creation of [(125)I]GIF-0082 and [(125)I]GIF-0276, which were synthesized by substituting a stannyl group with (125)I in the corresponding phenylstannane precursors.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Biological Transport / drug effects
  • Calcium / metabolism*
  • Dantrolene / analogs & derivatives*
  • Dantrolene / chemical synthesis
  • Dantrolene / pharmacology
  • Iodine Radioisotopes
  • Mice
  • Muscle Contraction / drug effects
  • Muscle Relaxants, Central / pharmacology*
  • Muscle, Skeletal / physiology
  • Muscle, Skeletal / ultrastructure
  • Photoaffinity Labels / chemical synthesis
  • Photoaffinity Labels / pharmacology*
  • Sarcoplasmic Reticulum / metabolism*

Substances

  • GIF 0082
  • Iodine Radioisotopes
  • Muscle Relaxants, Central
  • N-((3-iodo-5-(3-trifluoromethyl-3H-diazirin-3-yl))benzyl)dantrolene
  • Photoaffinity Labels
  • Dantrolene
  • Calcium