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N2915

Sigma-Aldrich

PYR-41

≥98% (HPLC), powder

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Synonym(s):
4[4-(5-Nitro-furan-2-ylmethylene)-3,5-dioxo-pyrazolidin-1-yl]-benzoic acid ethyl ester
Empirical Formula (Hill Notation):
C17H13N3O7
CAS Number:
418805-02-4
Molecular Weight:
371.30
UNSPSC Code:
12352200
PubChem Substance ID:
329818421
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

red to brown

solubility

DMSO: 5 mg/mL, clear (warmed)

storage temp.

−20°C

SMILES string

CCOC(=O)c1ccc(cc1)N2NC(=O)\C(=C/c3ccc(o3)[N+]([O-])=O)C2=O

InChI

1S/C17H13N3O7/c1-2-26-17(23)10-3-5-11(6-4-10)19-16(22)13(15(21)18-19)9-12-7-8-14(27-12)20(24)25/h3-9H,2H2,1H3,(H,18,21)/b13-9+

InChI key

ARGIPZKQJGFSGQ-UKTHLTGXSA-N

Application

PYR-41 has been used as E1 inhibitor:
  • to determine the cellular degradation pathways on adeno-associated viruses (AAV) transduction
  • to assess its selectivity and potency by matrix assisted laser desorption/ionization-time of flight (MALDI-TOF) E2/E3 assay
  • to treat fully differentiated C2C12 myotubes in high glucose medium for determining its effect on protein ubiquitination and cell viability
  • in the pretreatment of human brain microvascular endothelial cells (hBMECs) for the inhibition studies before infection with bacteria

Biochem/physiol Actions

PYR-41 inhibits E1 ubiquitin ligases like mouse double minute 2 homolog (MDM2), Itchy (ITCH) and HOIL-1L interacting protein (HOIP). It has anticancer potential.
PYR-41 is a cell permeable inhibitor of Ubiquitin activating enzyme (E1) with little or no activity against E3, E2, or caspase enzymatic activity.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H317

Hazard Classifications

Acute Tox. 4 Oral - Skin Sens. 1

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Inês B Santarino et al.
Scientific reports, 7(1), 5812-5812 (2017-07-21)
Erythrophagocytosis, the phagocytic removal of damaged red blood cells (RBC), and subsequent phagolysosome biogenesis are important processes in iron/heme metabolism and homeostasis. Phagolysosome biogenesis implies the interaction of nascent phagosomes with endocytic compartments and also autophagy effectors. Here, we report
Chun-Tao Lei et al.
Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology, 42(1), 281-294 (2017-05-24)
Protein Kinase C-α (PKC-α) and epidermal growth factor receptor (EGFR) are both involved in diabetic kidney disease; however, the connection between these two proteins during high glucose-induced podocyte injury remains uncertain. Diabetes was induced in SD rats by streptozotocin (STZ).
Implication of altered ubiquitin-proteasome system and ER stress in the muscle atrophy of diabetic rats
Reddy SS, et al.
Archives of Biochemistry and Biophysics, 639(9), 16-25 (2018)
Heterogeneity in pneumolysin expression governs the fate of Streptococcus pneumoniae during blood-brain barrier trafficking
Surve MV, et al.
PLoS Pathogens, 14(7), e1007168-e1007168 (2018)
Sandhya Manohar et al.
Antioxidants & redox signaling, 31(15), 1133-1149 (2019-09-05)
Aims: Ubiquitin is a highly conserved protein modifier that heavily accumulates during the oxidative stress response. Here, we investigated
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