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SML3531

Sigma-Aldrich

UPF-648

≥98% (HPLC)

Synonym(s):

(1S,2S)-2-(3,4-Dichlorobenzoyl)cyclopropanecarboxylic acid, (1S,2S)-2-[(3,4-Dichlorophenyl)carbonyl]cyclopropane-1-carboxylic acid, DBCC, UPF 648, UPF648

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About This Item

Empirical Formula (Hill Notation):
C11H8Cl2O3
CAS Number:
213400-34-1
Molecular Weight:
259.09
MDL number:
MFCD32705001
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

SMILES string

O=C(O)[C@@H]1[C@H](C1)C(C2=CC=C(C(Cl)=C2)Cl)=O

InChI

1S/C11H8Cl2O3/c12-8-2-1-5(3-9(8)13)10(14)6-4-7(6)11(15)16/h1-3,6-7H,4H2,(H,15,16)/t6-,7-/m0/s1

InChI key

ZBRKMOHDGFGXLN-BQBZGAKWSA-N

Biochem/physiol Actions

UPF-648 is a potent, active site-targeting kynurenine 3-monooxygenase (KMO; kynurenine 3-hydroxylase) inhibitor (IC50 = 20 nM) that prevents productive binding of the substrate L-kynurenine by perturbing the local active-site structure. UPF-648 protects against neurodegeneration in a murine (30 mg/kg, i.p.) and a Drosophila (100 μM in maize media) model of Huntington′s disease by shifting kynurenine pathway metabolism towards enhanced neuroprotective kynurenic acid (KYNA) formation and away from the free radicals generator 3-hydroxykynurenine (3-HK) and the excitotoxic quinolinic acid (QUIN).

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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Endogenous kynurenate controls the vulnerability of striatal neurons to quinolinate: Implications for Huntington's disease
Sapko MT, Guidetti P, Yu P, Tagle DA, Pellicciari R, Schwarcz R
Experimental Neurology, 197, 31-40 (2006)
Tzu-Ting Huang et al.
EBioMedicine, 54, 102717-102717 (2020-04-09)
Triple-negative breast cancer (TNBC) is aggressive and has a poor prognosis. Kynurenine 3-monooxygenase (KMO), a crucial kynurenine metabolic enzyme, is involved in inflammation, immune response and tumorigenesis. We aimed to study the role of KMO in TNBC. KMO alteration and
Ewelina Rojewska et al.
Frontiers in pharmacology, 9, 724-724 (2018-07-28)
Neuropathic pain caused by a primary injury or dysfunction in the peripheral or central nervous system is a tremendous therapeutic challenge. Here, we have collected the first evidence from a single study on the potential contributions to neuropathic pain development

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