Simulations of CYP51A from Aspergillus fumigatus in a model bilayer provide insights into triazole drug resistance

Med Mycol. 2018 Apr 1;56(3):361-373. doi: 10.1093/mmy/myx056.

Abstract

Azole antifungal drugs target CYP51A in Aspergillus fumigatus by binding with the active site of the protein, blocking ergosterol biosynthesis. Resistance to azole antifungal drugs is now common, with a leucine to histidine amino acid substitution at position 98 the most frequent, predominantly conferring resistance to itraconazole, although cross-resistance has been reported in conjunction with other mutations. In this study, we create a homology model of CYP51A using a recently published crystal structure of the paralog protein CYP51B. The derived structures, wild type, and L98H mutant are positioned within a lipid membrane bilayer and subjected to molecular dynamics simulations in order improve the accuracy of both models. The structural analysis from our simulations suggests a decrease in active site surface from the formation of hydrogen bonds between the histidine substitution and neighboring polar side chains, potentially preventing the binding of azole drugs. This study yields a biologically relevant structure and set of dynamics of the A. fumigatus Lanosterol 14 alpha-demethylase enzyme and provides further insight into azole antifungal drug resistance.

MeSH terms

  • Amino Acid Substitution
  • Antifungal Agents / pharmacology
  • Aspergillus fumigatus / enzymology*
  • Aspergillus fumigatus / genetics*
  • Binding Sites
  • Computer Simulation
  • Cytochrome P-450 Enzyme System / chemistry*
  • Cytochrome P-450 Enzyme System / genetics
  • Cytochrome P-450 Enzyme System / metabolism*
  • Databases, Protein
  • Drug Resistance, Fungal / genetics*
  • Fungal Proteins / chemistry*
  • Fungal Proteins / genetics
  • Fungal Proteins / metabolism*
  • Models, Biological*
  • Models, Molecular
  • Protein Conformation
  • Structure-Activity Relationship
  • Triazoles / pharmacology*

Substances

  • Antifungal Agents
  • Fungal Proteins
  • Triazoles
  • Cytochrome P-450 Enzyme System
  • cytochrome P-450 CYP51A, Aspergillus
  • cytochrome P-450 CYP51B, Aspergillus