Evaluating the potential of vacuolar ATPase inhibitors as anticancer agents and multigram synthesis of the potent salicylihalamide analog saliphenylhalamide

Bioorg Med Chem Lett. 2008 Nov 15;18(22):5879-83. doi: 10.1016/j.bmcl.2008.07.003. Epub 2008 Jul 5.

Abstract

The natural product salicylihalamide is a potent inhibitor of the Vacuolar ATPase (V-ATPase), a potential target for antitumor chemotherapy. We generated salicylihalamide-resistant tumor cell lines typified by an overexpansion of lysosomal organelles. We also found that many tumor cell lines upregulate tissue-specific plasmalemmal V-ATPases, and hypothesize that tumors that derive their energy from glycolysis rely on these isoforms to maintain a neutral cytosolic pH. To further validate the potential of V-ATPase inhibitors as leads for cancer chemotherapy, we developed a multigram synthesis of the potent salicylihalamide analog saliphenylhalamide.

Publication types

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

MeSH terms

  • Amides / chemical synthesis*
  • Amides / chemistry
  • Amides / pharmacology*
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Biological Products / chemical synthesis*
  • Biological Products / chemistry
  • Biological Products / pharmacology*
  • Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
  • Bridged Bicyclo Compounds, Heterocyclic / chemistry
  • Bridged Bicyclo Compounds, Heterocyclic / pharmacology*
  • Drug Screening Assays, Antitumor
  • Humans
  • Molecular Structure
  • Salicylates / chemical synthesis*
  • Salicylates / chemistry
  • Salicylates / pharmacology*
  • Vacuolar Proton-Translocating ATPases / antagonists & inhibitors*

Substances

  • Amides
  • Antineoplastic Agents
  • Biological Products
  • Bridged Bicyclo Compounds, Heterocyclic
  • Salicylates
  • salicylihalamide A
  • saliphenylhalamide
  • Vacuolar Proton-Translocating ATPases