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S8442

Sigma-Aldrich

SU 5416

≥98% (HPLC)

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Synonym(s):
1,3-Dihydro-3-[(3,5-dimethyl-1H-pyrrol-2-yl)methylene]-2H-indol-2-one
Empirical Formula (Hill Notation):
C15H14N2O
CAS Number:
204005-46-9
Molecular Weight:
238.28
MDL number:
MFCD01940922
PubChem Substance ID:
24278606
NACRES:
NA.77

Quality Level

100

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

SMILES string

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

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+

InChI key

WUWDLXZGHZSWQZ-XYOKQWHBSA-N

Gene Information

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

Application

SU 516 was used to study the mechanism of development of cerebral vasculature in zebrafish hindbrain.3 It was used to study the pulmonary vascular remodeling in response to hypoxia in mouse model of pulmonary arterial hypertension.4

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 Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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
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
Yong Liu et al.
Journal of orthopaedic translation, 23, 29-37 (2020-06-02)
Accelerating the process of bone regeneration is of great interest for surgeons and basic scientists alike. Recently, umbilical cord mesenchymal stem cells (UCMSCs) are considered clinically applicable for tissue regeneration due to their noninvasive harvesting and better viability. Nonetheless, the
Xiaowei Nie et al.
Journal of hypertension, 35(12), 2419-2435 (2017-07-14)
Similar to cancer, pulmonary arterial hypertension (PAH) is characterized by vascular remodeling, which leads to obliteration of the small pulmonary arteriole, with marked proliferation of pulmonary artery smooth muscle cells (PASMC) and/or endothelial cells dysfunction. Aberrant expression of tumor suppressor
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
View All Related Papers

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