Design and Biological Evaluation of Manganese- and Ruthenium-Based Hybrid CO-RMs (HYCOs)

ChemMedChem. 2019 Sep 18;14(18):1684-1691. doi: 10.1002/cmdc.201900426. Epub 2019 Aug 23.

Abstract

Interest in the therapeutic effects of carbon monoxide (CO), a product of heme degradation catalyzed by the enzyme heme oxygenase-1 (HO-1), has led to the development of CO-releasing molecules (CO-RMs) for the controlled delivery of this gas in vivo. We recently proposed conjugating a cobalt-based CO-RM with various activators of nuclear factor erythroid 2-related factor 2 (Nrf2), the transcription factor that regulates HO-1 expression, in order to exploit the beneficial effects of exogenous and endogenous CO. In this study, we describe the preparation of hybrid molecules (termed HYCOs) conjugating a fumaric acid derivative as an Nrf2 activator to a Mn- or a Ru-based CO-RM known to be pharmacologically active. With the exception of an acyl-manganese complex, these hybrids were obtained by associating the two bioactive entities by means of a linker of variable structure. X-ray diffraction analyses and preliminary biological investigations are also presented.

Keywords: biological activity; drug design; manganese; medicinal chemistry; ruthenium.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Carbon Monoxide / chemistry
  • Carbon Monoxide / pharmacology*
  • Cell Line
  • Crystallography, X-Ray
  • Dose-Response Relationship, Drug
  • Drug Design
  • Fumarates / chemistry
  • Fumarates / pharmacology*
  • Manganese / chemistry
  • Manganese / pharmacology*
  • Mice
  • Models, Molecular
  • Molecular Structure
  • NF-E2-Related Factor 2 / metabolism*
  • Organometallic Compounds / chemical synthesis
  • Organometallic Compounds / chemistry
  • Organometallic Compounds / pharmacology*
  • Ruthenium / chemistry
  • Ruthenium / pharmacology*
  • Structure-Activity Relationship

Substances

  • Fumarates
  • NF-E2-Related Factor 2
  • Nfe2l2 protein, mouse
  • Organometallic Compounds
  • Manganese
  • Carbon Monoxide
  • Ruthenium
  • fumaric acid