Effects of azaspiracid-1, a potent cytotoxic agent, on primary neuronal cultures. A structure-activity relationship study

J Med Chem. 2007 Jan 25;50(2):356-63. doi: 10.1021/jm061063g.

Abstract

Azaspiracids (AZAs) are marine phycotoxins with an unknown mechanism of action, implicated in human intoxications. We investigated the effect of azaspiracid-1 (AZA-1) on the cytosolic calcium concentration ([Ca2+]c), intracellular pH (pHi), and neuron viability in neuronal cultures. AZA-1 increased [Ca2+]c and decreased neuronal viability. The effects of several fragments of the AZA-1 molecule (13 different chemical structures) were examined. The ent-ABCD-azaspiracid-1 (2) showed similar potency to AZA-1 (1) in increasing [Ca2+]c but higher cytotoxity than AZA-1. The chemical structures containing only the ABCD or the ABCDE ring domains (3-8) caused a [Ca2+]c increase but did not alter cell viability. The compounds containing only the FGHI ring domain of AZA-1 (9-14) did not modify the [Ca2+]c or the cell viability. Therefore, the effect of AZA-1 on [Ca2+]c depends on the presence of the ABCD or the ABCDE-ring structure, but the complete chemical structure is needed to produce neurotoxic effects.

Publication types

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

MeSH terms

  • Actins / metabolism
  • Animals
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacology
  • Calcium / metabolism
  • Cell Survival / drug effects
  • Cells, Cultured
  • Cerebellum / cytology
  • Cytoskeleton / drug effects
  • Cytosol / metabolism
  • Hydrogen-Ion Concentration
  • Intracellular Fluid / chemistry
  • Marine Toxins / chemistry*
  • Marine Toxins / pharmacology
  • Mice
  • Neurons / cytology
  • Neurons / drug effects*
  • Spiro Compounds / chemistry*
  • Spiro Compounds / pharmacology
  • Structure-Activity Relationship

Substances

  • Actins
  • Antineoplastic Agents
  • Marine Toxins
  • Spiro Compounds
  • azaspiracid
  • Calcium