"Seriously Sweet": Acesulfame K Exhibits Selective Inhibition Using Alternative Binding Modes in Carbonic Anhydrase Isoforms

J Med Chem. 2018 Feb 8;61(3):1176-1181. doi: 10.1021/acs.jmedchem.7b01470. Epub 2018 Jan 5.

Abstract

Human carbonic anhydrase IX (CA IX) is upregulated in neoplastic tissues; as such, it is studied as a drug target for anticancer chemotherapy. Inhibition of CA IX has been shown to be therapeutically favorable in terms of reducing tumor growth. Previously, saccharin, a commonly used artificial sweetener, has been observed to selectively inhibit CA IX over other CA isoforms. In this study, X-ray crystallography showed acesulfame potassium (Ace K) binding directly to the catalytic zinc in CA IX (mimic) and through a bridging water in CA II. This modulation in binding is reflected in the binding constants, with Ace K inhibiting CA IX but not other CA isoforms. Hence, this study establishes the potential of Ace K (an FDA approved food additive) as a lead compound in the design and development of CA IX specific inhibitors.

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

  • Carbonic Anhydrase II / antagonists & inhibitors*
  • Carbonic Anhydrase II / chemistry
  • Carbonic Anhydrase II / metabolism*
  • Carbonic Anhydrase IX / antagonists & inhibitors*
  • Carbonic Anhydrase IX / chemistry
  • Carbonic Anhydrase IX / metabolism*
  • Carbonic Anhydrase Inhibitors / metabolism
  • Carbonic Anhydrase Inhibitors / pharmacology
  • Catalytic Domain
  • Crystallography, X-Ray
  • Models, Molecular
  • Protein Binding
  • Structure-Activity Relationship
  • Thiazines / metabolism*
  • Thiazines / pharmacology*

Substances

  • Carbonic Anhydrase Inhibitors
  • Thiazines
  • Carbonic Anhydrase II
  • Carbonic Anhydrase IX
  • acetosulfame