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SML1105

Sigma-Aldrich

UCF-101

≥98% (HPLC)

Synonym(s):

Dihydro-5-[[5-(2-nitrophenyl)-2-furanyl]methylene]-1,3-diphenyl-2-thioxo-4,6(1H,5H)-pyrimidinedione

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About This Item

Empirical Formula (Hill Notation):
C27H17N3O5S
CAS Number:
313649-08-0
Molecular Weight:
495.51
MDL number:
MFCD01000361
UNSPSC Code:
12352200
PubChem Substance ID:
329825480
NACRES:
NA.77

assay

≥98% (HPLC)

form

powder

color

light orange to dark orange

solubility

DMSO: 5 mg/mL, clear (warmed)

storage temp.

−20°C

SMILES string

S=C(N(C1=CC=CC=C1)C2=O)N(C3=CC=CC=C3)C(C2=CC4=CC=C(C5=CC=CC=C5[N+]([O-])=O)O4)=O

InChI

1S/C27H17N3O5S/c31-25-22(17-20-15-16-24(35-20)21-13-7-8-14-23(21)30(33)34)26(32)29(19-11-5-2-6-12-19)27(36)28(25)18-9-3-1-4-10-18/h1-17H

InChI key

NVNSXBXKNMWKEJ-UHFFFAOYSA-N

Application

UCF-101 has been used to study its cytoprotective activity in a mouse model of spinal cord injury.

Biochem/physiol Actions

UCF-101 is a selective inhibitor of the pro-apoptotic mitochondrial serine protease Omi/HtrA2, involved in the cellular response to thermal and oxidative stress. Like SMAC/Diablo, Omi/HtrA2 is an inhibitor of IAPs (inhibitor of apoptosis proteins), inhibiting the apoptosis inhibitors, thus resulting in pro-apoptotic activity. In septic rat studies, UCF-101 was found to inhibit apoptosis and have neuroprotective effects on cerebral oxidative injury and cognitive impairment. In aging rats with induced myocardial ischemia/reperfusion (MI/R) injury, UCF-101 treatment decreased XIAP degradation and caspase-3 activity and exerted cardioprotective effects.

Features and Benefits

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

Storage Class

11 - Combustible Solids

wgk_germany

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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Acute administration of ucf-101 ameliorates the locomotor impairments induced by a traumatic spinal cord injury
D.Reigada
Neuroscience, 300(6), 404-417 (2015)
Pengfei Wang et al.
Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology, 49(6), 2163-2173 (2018-10-05)
the pathogenesis of sepsis-associated encephalopathy (SAE) is multifactorial, involving neurotransmitter alterations, inflammatory cytokines, oxidative damage, mitochondrial dysfunction, apoptosis, and other factors. Mitochondria are major producers of reactive oxygen species, resulting in cellular injury. Omi/HtrA2 is a proapoptotic mitochondrial serine protease

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