8OFA

Crystal structure of human cathepsin L interacting with tosyl phenylalanyl chloromethyl ketone (TPCK)


Experimental Data Snapshot

  • Method: X-RAY DIFFRACTION
  • Resolution: 1.90 Å
  • R-Value Free: 0.217 
  • R-Value Work: 0.175 
  • R-Value Observed: 0.176 

wwPDB Validation   3D Report Full Report


Ligand Structure Quality Assessment 


This is version 1.2 of the entry. See complete history


Literature

Structural Elucidation and Antiviral Activity of Covalent Cathepsin L Inhibitors.

Falke, S.Lieske, J.Herrmann, A.Loboda, J.Karnicar, K.Gunther, S.Reinke, P.Y.A.Ewert, W.Usenik, A.Lindic, N.Sekirnik, A.Dretnik, K.Tsuge, H.Turk, V.Chapman, H.N.Hinrichs, W.Ebert, G.Turk, D.Meents, A.

(2024) J Med Chem 67: 7048-7067

  • DOI: https://doi.org/10.1021/acs.jmedchem.3c02351
  • Primary Citation of Related Structures:  
    7QKD, 7ZS7, 7ZVF, 7ZXA, 8A4U, 8A4V, 8A4W, 8A4X, 8A5B, 8AHV, 8B4F, 8C77, 8OFA, 8OZA, 8PRX, 8QKB

  • PubMed Abstract: 

    Emerging RNA viruses, including SARS-CoV-2, continue to be a major threat. Cell entry of SARS-CoV-2 particles via the endosomal pathway involves cysteine cathepsins. Due to ubiquitous expression, cathepsin L (CatL) is considered a promising drug target in the context of different viral and lysosome-related diseases. We characterized the anti-SARS-CoV-2 activity of a set of carbonyl- and succinyl epoxide-based inhibitors, which were previously identified as inhibitors of cathepsins or related cysteine proteases. Calpain inhibitor XII, MG-101, and CatL inhibitor IV possess antiviral activity in the very low nanomolar EC 50 range in Vero E6 cells and inhibit CatL in the picomolar K i range. We show a relevant off-target effect of CatL inhibition by the coronavirus main protease α-ketoamide inhibitor 13b. Crystal structures of CatL in complex with 14 compounds at resolutions better than 2 Å present a solid basis for structure-guided understanding and optimization of CatL inhibitors toward protease drug development.


  • Organizational Affiliation

    Center for Free-Electron Laser Science CFEL, Deutsches Elektronen-Synchrotron DESY, Notkestraße 85, 22607 Hamburg, Germany.


Macromolecules
Find similar proteins by:  (by identity cutoff)  |  3D Structure
Entity ID: 1
MoleculeChains Sequence LengthOrganismDetailsImage
Cathepsin L
A, B, C, D
220Homo sapiensMutation(s): 1 
Gene Names: CTSLCTSL1
UniProt & NIH Common Fund Data Resources
Find proteins for P07711 (Homo sapiens)
Explore P07711 
Go to UniProtKB:  P07711
PHAROS:  P07711
GTEx:  ENSG00000135047 
Entity Groups  
Sequence Clusters30% Identity50% Identity70% Identity90% Identity95% Identity100% Identity
UniProt GroupP07711
Sequence Annotations
Expand
  • Reference Sequence
Small Molecules
Ligands 8 Unique
IDChains Name / Formula / InChI Key2D Diagram3D Interactions
TQ8 (Subject of Investigation/LOI)
Query on TQ8

Download Ideal Coordinates CCD File 
BA [auth D],
E [auth A],
O [auth B],
U [auth C]
N-[(2S)-4-chloro-3-oxo-1-phenyl-butan-2-yl]-4-methyl-benzenesulfonamide
C17 H18 Cl N O3 S
MQUQNUAYKLCRME-INIZCTEOSA-N
VLF (Subject of Investigation/LOI)
Query on VLF

Download Ideal Coordinates CCD File 
LA [auth D],
N [auth A]
4-methyl-~{N}-[(2~{S})-4-oxidanyl-3-oxidanylidene-1-phenyl-butan-2-yl]benzenesulfonamide
C17 H19 N O4 S
ANXKZQCDTVNETG-INIZCTEOSA-N
PG5
Query on PG5

Download Ideal Coordinates CCD File 
J [auth A]1-METHOXY-2-[2-(2-METHOXY-ETHOXY]-ETHANE
C8 H18 O4
YFNKIDBQEZZDLK-UHFFFAOYSA-N
PGE
Query on PGE

Download Ideal Coordinates CCD File 
FA [auth D],
I [auth A],
IA [auth D]
TRIETHYLENE GLYCOL
C6 H14 O4
ZIBGPFATKBEMQZ-UHFFFAOYSA-N
PEG
Query on PEG

Download Ideal Coordinates CCD File 
CA [auth D]
G [auth A]
M [auth A]
P [auth B]
V [auth C]
CA [auth D],
G [auth A],
M [auth A],
P [auth B],
V [auth C],
W [auth C],
X [auth C]
DI(HYDROXYETHYL)ETHER
C4 H10 O3
MTHSVFCYNBDYFN-UHFFFAOYSA-N
DMS
Query on DMS

Download Ideal Coordinates CCD File 
DA [auth D]
H [auth A]
JA [auth D]
K [auth A]
L [auth A]
DA [auth D],
H [auth A],
JA [auth D],
K [auth A],
L [auth A],
R [auth B],
T [auth B],
Y [auth C],
Z [auth C]
DIMETHYL SULFOXIDE
C2 H6 O S
IAZDPXIOMUYVGZ-UHFFFAOYSA-N
EDO
Query on EDO

Download Ideal Coordinates CCD File 
AA [auth C]
EA [auth D]
F [auth A]
GA [auth D]
HA [auth D]
AA [auth C],
EA [auth D],
F [auth A],
GA [auth D],
HA [auth D],
KA [auth D],
Q [auth B]
1,2-ETHANEDIOL
C2 H6 O2
LYCAIKOWRPUZTN-UHFFFAOYSA-N
ACT
Query on ACT

Download Ideal Coordinates CCD File 
S [auth B]ACETATE ION
C2 H3 O2
QTBSBXVTEAMEQO-UHFFFAOYSA-M
Experimental Data & Validation

Experimental Data

  • Method: X-RAY DIFFRACTION
  • Resolution: 1.90 Å
  • R-Value Free: 0.217 
  • R-Value Work: 0.175 
  • R-Value Observed: 0.176 
  • Space Group: P 1
Unit Cell:
Length ( Å )Angle ( ˚ )
a = 56.96α = 105.065
b = 62.73β = 94.087
c = 67.37γ = 115.543
Software Package:
Software NamePurpose
PHENIXrefinement
XDSdata reduction
XSCALEdata scaling
PHENIXphasing

Structure Validation

View Full Validation Report



Ligand Structure Quality Assessment 


Entry History & Funding Information

Deposition Data


Funding OrganizationLocationGrant Number
Helmholtz AssociationGermanyFISCOV
Helmholtz AssociationGermanySFragX
German Federal Ministry for Education and ResearchGermany031B0405
Slovenian Research AgencySloveniaP1-0048
Slovenian Research AgencySloveniaIO-0048

Revision History  (Full details and data files)

  • Version 1.0: 2023-11-29
    Type: Initial release
  • Version 1.1: 2024-05-15
    Changes: Database references
  • Version 1.2: 2024-05-22
    Changes: Database references