Naphthylisoquinoline alkaloids, a new structural template inhibitor of Nav1.7 sodium channel

Acta Pharmacol Sin. 2023 Sep;44(9):1768-1776. doi: 10.1038/s41401-023-01084-9. Epub 2023 May 4.

Abstract

Voltage-gated sodium channel 1.7 (Nav1.7) remains one of the most promising drug targets for pain relief. In the current study, we conducted a high-throughput screening of natural products in our in-house compound library to discover novel Nav1.7 inhibitors, then characterized their pharmacological properties. We identified 25 naphthylisoquinoline alkaloids (NIQs) from Ancistrocladus tectorius to be a novel type of Nav1.7 channel inhibitors. Their stereostructures including the linkage modes of the naphthalene group at the isoquinoline core were revealed by a comprehensive analysis of HRESIMS, 1D, and 2D NMR spectra as well as ECD spectra and single-crystal X-ray diffraction analysis with Cu Kα radiation. All the NIQs showed inhibitory activities against the Nav1.7 channel stably expressed in HEK293 cells, and the naphthalene ring in the C-7 position displayed a more important role in the inhibitory activity than that in the C-5 site. Among the NIQs tested, compound 2 was the most potent with an IC50 of 0.73 ± 0.03 µM. We demonstrated that compound 2 (3 µM) caused dramatical shift of steady-state slow inactivation toward the hyperpolarizing direction (V1/2 values were changed from -39.54 ± 2.77 mV to -65.53 ± 4.39 mV, which might contribute to the inhibition of compound 2 against the Nav1.7 channel. In acutely isolated dorsal root ganglion (DRG) neurons, compound 2 (10 μM) dramatically suppressed native sodium currents and action potential firing. In the formalin-induced mouse inflammatory pain model, local intraplantar administration of compound 2 (2, 20, 200 nmol) dose-dependently attenuated the nociceptive behaviors. In summary, NIQs represent a new type of Nav1.7 channel inhibitors and may act as structural templates for the following analgesic drug development.

Keywords: Ancistrocladus tectorius; Nav1.7 channel; analgesics; dorsal root ganglion neurons; formalin-induced mouse inflammatory pain model; naphthylisoquinolines.

MeSH terms

  • Alkaloids* / pharmacology
  • Alkaloids* / therapeutic use
  • Animals
  • Ganglia, Spinal
  • HEK293 Cells
  • Humans
  • Mice
  • NAV1.7 Voltage-Gated Sodium Channel*
  • Neurons
  • Pain / drug therapy
  • Sodium Channel Blockers / pharmacology
  • Sodium Channel Blockers / therapeutic use

Substances

  • NAV1.7 Voltage-Gated Sodium Channel
  • Alkaloids
  • Sodium Channel Blockers