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Merck

S8442

SU 5416

≥98% (HPLC), powder, neuronal nitric oxide synthase inhibitor

Synonym(s):

1,3-Dihydro-3-[(3,5-dimethyl-1H-pyrrol-2-yl)methylene]-2H-indol-2-one

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About This Item

Empirical Formula (Hill Notation):
C15H14N2O
CAS Number:
204005-46-9
Molecular Weight:
238.28
UNSPSC Code:
51111800
PubChem Substance ID:
24278606
NACRES:
NA.77
MDL number:
MFCD01940922
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
100

Key Documents

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Product Name

SU 5416, ≥98% (HPLC)

SMILES string

Cc1cc(C)c(C=C2C(=O)Nc3ccccc23)[nH]1

InChI key

WUWDLXZGHZSWQZ-XYOKQWHBSA-N

InChI

1S/C15H14N2O/c1-9-7-10(2)16-14(9)8-12-11-5-3-4-6-13(11)17-15(12)18/h3-8,16H,1-2H3,(H,17,18)/b12-8+

assay

≥98% (HPLC)

form

powder

color

yellow to yellow-orange

mp

221-222 °C

solubility

DMSO: 20 mg/mL, clear (warmed), H2O: insoluble

storage temp.

−20°C

Quality Level

100

Gene Information

human ... EGFR(1956), FLT1(2321), IGFBP1(3484), IL2(3558), KDR(3791), PDGFRB(5159)
mouse ... Flt1(14254), Kdr(16542)

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General description

SU 5416 is a vascular endothelial growth factor (VEGF) receptor protein tyrosine kinase 1/2 inhibitor. SU 5416 is known to prevent tumor growth and tumor angiogenesis. SU 5416 inhibits the activity of neuronal nitric oxide synthase and protects the neuronal cells from nitric oxide-mediated neurotoxicity. It also acts as an agonist of aryl hydrocarbon receptor and may be an effective clinical agent for treating autoimmune diseases and transplant rejection.

Application

SU 5416 has been used to treat HUVEC cells before the tube formation assay to assess its impact on the network generated from tube formation. to induce pulmonary hypertension (PH) in mice to serve as an experimental model

Biochem/physiol Actions

SU 516 inhibits the activity of neuronal nitric oxide synthase and protects the neuronal cells from nitric oxide-mediated neurotoxicity.1 It also acts an agonist of aryl hydrocarbon receptor and is an effective clinical agent for treating autoimmune diseases and transplant rejection.2
SU 5416 is a vascular endothelial growth factor (VEGF) receptor protein tyrosine kinase 1/2 inhibitor.

Features and Benefits

This compound is a featured product for Kinase Phosphatase Biology research. Click here to discover more featured Kinase Phosphatase Biology products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Storage Class

11 - Combustible Solids

ppe

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Certificates of Analysis (COA)

Lot/Batch Number
0000477425
0000477425
0000292879
0000292879
0000401563

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Joshua D Mezrich et al.
PloS one, 7(9), e44547-e44547 (2012-09-13)
The experimental compound SU5416 went as far as Phase III clinical trials as an anticancer agent, putatively because of its activity as a VEGFR-2 inhibitor, but showed poor results. Here, we show that SU5416 is also an aryl hydrocarbon receptor
Loredana Ciuclan et al.
American journal of respiratory and critical care medicine, 184(10), 1171-1182 (2011-08-27)
The complex pathologies associated with severe pulmonary arterial hypertension (PAH) in humans have been a challenge to reproduce in mice due to the subtle phenotype displayed to PAH stimuli. Here we aim to develop a novel murine model of PAH
Charlene Watterston et al.
PLoS genetics, 17(8), e1009769-e1009769 (2021-08-24)
Vessel growth integrates diverse extrinsic signals with intrinsic signaling cascades to coordinate cell migration and sprouting morphogenesis. The pro-angiogenic effects of Vascular Endothelial Growth Factor (VEGF) are carefully controlled during sprouting to generate an efficiently patterned vascular network. We identify
Florian Ulrich et al.
Developmental biology, 357(1), 134-151 (2011-07-13)
The brain is made of billions of highly metabolically active neurons whose activities provide the seat for cognitive, affective, sensory and motor functions. The cerebral vasculature meets the brain's unusually high demand for oxygen and glucose by providing it with
Hidenori Moriyama et al.
Nature communications, 13(1), 3013-3013 (2022-06-01)
Pulmonary hypertension is a fatal rare disease that causes right heart failure by elevated pulmonary arterial resistance. There is an unmet medical need for the development of therapeutics focusing on the pulmonary vascular remodeling. Bioactive lipids produced by perivascular inflammatory
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