BPPSA

BPPSA
Names
IUPAC name
N-(2-Bromophenyl)-1-pyrrolidinesulfonamide
Identifiers
3D model (JSmol)
Abbreviations BPPSA
ChemSpider
  • InChI=1S/C10H13BrN2O2S/c11-9-5-1-2-6-10(9)12-16(14,15)13-7-3-4-8-13/h1-2,5-6,12H,3-4,7-8H2
    Key: SKZKXVWQIHWABR-UHFFFAOYSA-N
  • C1CCN(C1)S(=O)(=O)NC2=CC=CC=C2Br
Properties
C10H13BrN2O2S
Molar mass 305.19 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

BPPSA (N‐(2‐bromophenyl)pyrrolidine‐1‐sulfonamide) is a small molecular chaperone that helps partially stabilize the P187S variant of NQO1, recovering part of its lost catalytic activity.

Isothermal titration calorimetry shows that it binds the P187S variant at 20.0 uM, as compared to 7.95 uM for wildtype NQO1.

It is contrasted to dicoumarol, which binds the enzyme and acts as a competitive inhibitor.

An X-ray crystal structure of wild-type human NQO1 in complex with BPPSA is in the Protein Data Bank under the code PDB: 6FY4​.

References

  1. ↑ Strandback, Emilia; Lienhart, Wolf-Dieter; Hromic-Jahjefendic, Altijana; Bourgeois, Benjamin; Högler, Anja; Waltenstorfer, Daniel; Winkler, Andreas; Zangger, Klaus; Madl, Tobias; Gruber, Karl; Macheroux, Peter (2020). "A small molecule chaperone rescues the stability and activity of a cancer-associated variant of NAD(P)H:quinone oxidoreductase 1 in vitro". FEBS Letters. 594 (3): 424–438. doi:10.1002/1873-3468.13636. PMC 7027498. PMID 31605637.