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Antiviral API
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Pitstop 2
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| Category | Human immunodeficiency Virus (HIV) |
| CAS | 1332879-52-3 |
| Description | Pitstop 2 is a selective clathrin-mediated endocytosis (CME) inhibitor that selectively inhibits the interaction between the clathrin terminal domain and amphiphysin with an IC50 of 12 μM. It inhibits HIV-1 entry and infection in HeLa reporting cell line, and also inhibits clathrin-independent endocytosis of CD44, CD98 and CD147 in HeLa cells. It can seriously interfere with synaptic vesicle circulation. |
Product Information
| Synonyms | Clathrin-IN-1; (Z)-N-(5-(4-bromobenzylidene)-4-oxo-4,5-dihydrothiazol-2-yl)naphthalene-1-sulfonamide; 1-Naphthalenesulfonamide, N-[(5Z)-5-[(4-bromophenyl)methylene]-4,5-dihydro-4-oxo-2-thiazolyl]- |
| IUPAC Name | N-[(5Z)-5-(4-bromobenzylidene)-4-oxo-4,5-dihydro-1,3-thiazol-2-yl]-1-naphthalenesulfonamide |
| Molecular Weight | 473.36 |
| Molecular Formula | C20H13BrN2O3S2 |
| Canonical SMILES | C1=CC=C2C(=C1)C=CC=C2S(=O)(=O)N=C3NC(=O)C(=CC4=CC=C(C=C4)Br)S3 |
| InChI | InChI=1S/C20H13BrN2O3S2/c21-15-10-8-13(9-11-15)12-17-19(24)22-20(27-17)23-28(25,26)18-7-3-5-14-4-1-2-6-16(14)18/h1-12H,(H,22,23,24)/b17-12- |
| InChIKey | CGDLWHGPJPVPDU-ATVHPVEESA-N |
| Boiling Point | 652.3±65.0°C at 760 mmHg |
| Purity | ≥95% |
| Density | 1.6±0.1 g/cm3 |
| Solubility | Soluble in DMSO |
| Appearance | White to Light Brown Powder |
| Storage | Store at -20°C |
| Complexity | 767 |
| Exact Mass | 471.95510 |
| In Vitro | Preincubation of HeLa cells with Clathrin-IN-1 (Pitstops 2) leads to a dose-dependent inhibition of Tf uptake with an IC50 value (12-5 μM). Application of 30 μM Clathrin-IN-1 completely blocked Tf endocytosis. Clathrin-IN-1-induced block of Tf endocytosis in HeLa cells was completely reversed within 1-3 hr of drug washout. In U2OS cells, the IC50 for Tf uptake is 9.7 M. Pitstop 2 also causes a potent inhibition of EGF uptake. Clathrin-IN-1 (Pitstops 2) potently and specifically reduced HIV-1 infectivity by >90% in HeLa cells. Pitstop-induced inhibition of clathrin TD function acutely interferes with receptor-mediated endocytosis, entry of HIV, and synaptic vesicle recycling. Endocytosis inhibition is caused by a dramatic increase in the lifetimes of clathrin coat components, including FCHo, clathrin, and dynamin, suggesting that the clathrin TD regulates coated pit dynamics. |
| Target | HIV |
| XLogP3-AA | 5.5 |
