Skip to Content
Merck
All Photos(1)

Key Documents

More Documents

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

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

Quality Level

100

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 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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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

Related Content

Discover Bioactive Small Molecules for Apoptosis

Apoptosis, or programmed cell death (PCD), is a selective process for the removal of unnecessary, infected or transformed cells in various biological systems. As it plays a role in the homeostasis of multicellular organisms, apoptosis is tightly regulated through two principal pathways by a number of regulatory and effector molecules.

Discover Bioactive Small Molecules for Cell Cycle Research

n proliferating cells, the cell cycle consists of four phases. Gap 1 (G1) is the interval between mitosis and DNA replication that is characterized by cell growth. Replication of DNA occurs during the synthesis (S) phase, which is followed by a second gap phase (G2) during which growth and preparation for cell division occurs. Together, these three stages comprise the interphase phase of the cell cycle. Interphase is followed by the mitotic (M) phase.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service