One-pot synthesis of a new antifungal polymerisable monomer and its characterisation by coordination-ion spray mass spectrometry

Rapid Commun Mass Spectrom. 2011 Aug 15;25(15):2141-8. doi: 10.1002/rcm.5089.

Abstract

We have investigated the synthesis of a new antifungal agent with a polymerisable moiety for the prevention of denture stomatisis. Nystatin (antifungal polyene) is modified in one step by reaction with isocyanatoethylmethacrylate to afford a new polymerisable antifungal agent in good yield (90%). In order to prove the monografting of the acrylate derivative and to localise the new group in the skeleton of the molecule, a rapid and efficient analytical method involving electrospray ionisation mass spectrometry (ESI-MS) was developed for the study. In view of the structures of such antifungal agents, their complexation with metal cations was investigated by Coordination-Ion Spray Mass Spectrometry (CIS-MS). This mass spectrometry study covers two aspects: improving the MS signal to overcome the low ionisation efficiency in ESI-MS and exploring the complexation behaviour of the induced structure to optimise the antifungal properties.

MeSH terms

  • Antifungal Agents / chemical synthesis*
  • Antifungal Agents / chemistry*
  • Chromatography, High Pressure Liquid
  • Copper / chemistry
  • Isocyanates / chemistry*
  • Methacrylates / chemistry*
  • Nitrates / chemistry
  • Nystatin / chemical synthesis*
  • Nystatin / chemistry*
  • Polymerization
  • Spectrometry, Mass, Electrospray Ionization / methods*
  • Zinc Compounds / chemistry

Substances

  • Antifungal Agents
  • Isocyanates
  • Methacrylates
  • Nitrates
  • Zinc Compounds
  • isocyanatomethacrylate
  • Nystatin
  • Copper
  • copper(II) nitrate
  • zinc nitrate