8BP2

2.8A STRUCTURE OF ZOLIFLODACIN WITH S.AUREUS DNA GYRASE AND DNA


Experimental Data Snapshot

  • Method: X-RAY DIFFRACTION
  • Resolution: 2.80 Å
  • R-Value Free: 0.231 
  • R-Value Work: 0.191 

Starting Model: experimental
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This is version 1.2 of the entry. See complete history


Literature

A 2.8 angstrom Structure of Zoliflodacin in a DNA Cleavage Complex with Staphylococcus aureus DNA Gyrase.

Morgan, H.Lipka-Lloyd, M.Warren, A.J.Hughes, N.Holmes, J.Burton, N.P.Mahenthiralingam, E.Bax, B.D.

(2023) Int J Mol Sci 24

  • DOI: https://doi.org/10.3390/ijms24021634
  • Primary Citation of Related Structures:  
    8BP2

  • PubMed Abstract: 

    Since 2000, some thirteen quinolones and fluoroquinolones have been developed and have come to market. The quinolones, one of the most successful classes of antibacterial drugs, stabilize DNA cleavage complexes with DNA gyrase and topoisomerase IV (topo IV), the two bacterial type IIA topoisomerases. The dual targeting of gyrase and topo IV helps decrease the likelihood of resistance developing. Here, we report on a 2.8 Å X-ray crystal structure, which shows that zoliflodacin, a spiropyrimidinetrione antibiotic, binds in the same DNA cleavage site(s) as quinolones, sterically blocking DNA religation. The structure shows that zoliflodacin interacts with highly conserved residues on GyrB (and does not use the quinolone water-metal ion bridge to GyrA), suggesting it may be more difficult for bacteria to develop target mediated resistance. We show that zoliflodacin has an MIC of 4 µg/mL against Acinetobacter baumannii ( A. baumannii ), an improvement of four-fold over its progenitor QPT-1. The current phase III clinical trial of zoliflodacin for gonorrhea is due to be read out in 2023. Zoliflodacin, together with the unrelated novel bacterial topoisomerase inhibitor gepotidacin, is likely to become the first entirely novel chemical entities approved against Gram-negative bacteria in the 21st century. Zoliflodacin may also become the progenitor of a new safer class of antibacterial drugs against other problematic Gram-negative bacteria.


  • Organizational Affiliation

    Medicines Discovery Institute, Cardiff University, Cardiff CF10 3AT, UK.


Macromolecules

Find similar proteins by:  (by identity cutoff)  |  3D Structure
Entity ID: 1
MoleculeChains Sequence LengthOrganismDetailsImage
DNA gyrase subunit BA [auth BBB],
C [auth DDD]
189Staphylococcus aureusMutation(s): 0 
Gene Names: gyrBSA0005
EC: 5.6.2.2
UniProt
Find proteins for P66937 (Staphylococcus aureus (strain N315))
Explore P66937 
Go to UniProtKB:  P66937
Entity Groups  
Sequence Clusters30% Identity50% Identity70% Identity90% Identity95% Identity100% Identity
UniProt GroupP66937
Sequence Annotations
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  • Reference Sequence
Find similar proteins by:  (by identity cutoff)  |  3D Structure
Entity ID: 2
MoleculeChains Sequence LengthOrganismDetailsImage
DNA gyrase subunit AB [auth AAA],
D [auth CCC]
490Staphylococcus aureusMutation(s): 0 
Gene Names: gyrASA0006
EC: 5.6.2.2
UniProt
Find proteins for Q99XG5 (Staphylococcus aureus (strain N315))
Explore Q99XG5 
Go to UniProtKB:  Q99XG5
Entity Groups  
Sequence Clusters30% Identity50% Identity70% Identity90% Identity95% Identity100% Identity
UniProt GroupQ99XG5
Sequence Annotations
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  • Reference Sequence

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Entity ID: 3
MoleculeChains LengthOrganismImage
DNA (20-MER)E [auth EEE],
F [auth EbE],
G [auth FFF],
H [auth FbF]
20synthetic construct
Sequence Annotations
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  • Reference Sequence
Small Molecules
Ligands 5 Unique
IDChains Name / Formula / InChI Key2D Diagram3D Interactions
R8U (Subject of Investigation/LOI)
Query on R8U

Download Ideal Coordinates CCD File 
T [auth EbE],
V [auth FbF]
Zoliflodacin
C22 H22 F N5 O7
ZSWMIFNWDQEXDT-ZESJGQACSA-N
BTB
Query on BTB

Download Ideal Coordinates CCD File 
R [auth CCC]2-[BIS-(2-HYDROXY-ETHYL)-AMINO]-2-HYDROXYMETHYL-PROPANE-1,3-DIOL
C8 H19 N O5
OWMVSZAMULFTJU-UHFFFAOYSA-N
GOL
Query on GOL

Download Ideal Coordinates CCD File 
I [auth BBB]
K [auth AAA]
M [auth AAA]
N [auth AAA]
O [auth AAA]
I [auth BBB],
K [auth AAA],
M [auth AAA],
N [auth AAA],
O [auth AAA],
S [auth CCC],
U [auth FbF]
GLYCEROL
C3 H8 O3
PEDCQBHIVMGVHV-UHFFFAOYSA-N
MN
Query on MN

Download Ideal Coordinates CCD File 
J [auth BBB],
P [auth DDD],
Q [auth CCC]
MANGANESE (II) ION
Mn
WAEMQWOKJMHJLA-UHFFFAOYSA-N
NA
Query on NA

Download Ideal Coordinates CCD File 
L [auth AAA]SODIUM ION
Na
FKNQFGJONOIPTF-UHFFFAOYSA-N
Binding Affinity Annotations 
IDSourceBinding Affinity
R8U BindingDB:  8BP2 IC50: 4300 (nM) from 1 assay(s)
Experimental Data & Validation

Experimental Data

  • Method: X-RAY DIFFRACTION
  • Resolution: 2.80 Å
  • R-Value Free: 0.231 
  • R-Value Work: 0.191 
  • Space Group: P 61
Unit Cell:
Length ( Å )Angle ( ˚ )
a = 94.542α = 90
b = 94.542β = 90
c = 417.134γ = 120
Software Package:
Software NamePurpose
REFMACrefinement
DIALSdata reduction
DIALSdata scaling
PHENIXphasing

Structure Validation

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Ligand Structure Quality Assessment 


Entry History & Funding Information

Deposition Data


Funding OrganizationLocationGrant Number
UK Research and Innovation (UKRI)United Kingdom--

Revision History  (Full details and data files)

  • Version 1.0: 2023-02-08
    Type: Initial release
  • Version 1.1: 2024-02-07
    Changes: Data collection
  • Version 1.2: 2024-11-06
    Changes: Structure summary