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N2915

Sigma-Aldrich

PYR-41

≥98% (HPLC), powder

Synonym(s):

4[4-(5-Nitro-furan-2-ylmethylene)-3,5-dioxo-pyrazolidin-1-yl]-benzoic acid ethyl ester

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About This Item

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

Storage Class Code

11 - Combustible Solids

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)
Shingo Matsuo et al.
American journal of physiology. Gastrointestinal and liver physiology, 315(2), G283-G292 (2018-05-18)
Intestinal ischemia-reperfusion (I/R) occurs in various clinical settings, such as transplantation, acute mesenteric arterial occlusion, trauma, and shock. I/R injury causes severe systemic inflammation, leading to multiple organ dysfunction associated with high mortality. The ubiquitin proteasome pathway has been indicated
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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