Pitstop® 1, clathrin inhibitor

Key facts

CAS number

1332879-51-2

Form

Solid

form

Molecular weight

404.4 Da

Molecular formula

C₁₉H₁₃N₂NaO₅S

PubChem

71483522

Nature

Synthetic

Solubility

Soluble in water to 25 mM

Soluble in DMSO to 100 mM

Biochemical name

Pitstop 1

Biological description

Selective clathrin inhibitor. Competitively inhibits clathrin terminal domain (TD) to selectively inhibit clathrin mediated endocytosis (IC50 = ~18 μM for inhibition of amphiphysin association of clathrin TD). Interferes with receptor mediated endocytosis, entry of HIV and synaptic vesicle recycling. Exhibits limited cell membrane penetration, however it is active in cells after microinjection.

Canonical smiles

C1=CC2=CC(=CC3=C2C(=C1)C(=O)N(C3=O)CC4=CC=C(C=C4)N)S(=O)(=O)[O-].[Na+]

InChi

InChI=1S/C19H14N2O5S.Na/c20-13-6-4-11(5-7-13)10-21-18(22)15-3-1-2-12-8-14(27(24,25)26)9-16(17(12)15)19(21)23;/h1-9H,10,20H2,(H,24,25,26);/q;+1/p-1

InChiKey

MKPPGLKJTZAXNE-UHFFFAOYSA-M

IUPAC Name

sodium;2-[(4-aminophenyl)methyl]-1,3-dioxobenzo[de]isoquinoline-5-sulfonate