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SML3531

Sigma-Aldrich

UPF-648

≥98% (HPLC)

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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
Empirical Formula (Hill Notation):
C11H8Cl2O3
CAS Number:
213400-34-1
Molecular Weight:
259.09
MDL number:
MFCD32705001

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

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SML3706SML3136U111
UPF-648 ≥98% (HPLC)

Sigma-Aldrich

SML3531

UPF-648

BT2 ≥98% (HPLC)

Sigma-Aldrich

SML3706

BT2

CGP-54626 ≥95% (HPLC)

Sigma-Aldrich

SML3136

CGP-54626

(−)-trans-(1S,2S)-U-50488 hydrochloride hydrate solid, ≥98% (HPLC)

Sigma-Aldrich

U111

(−)-trans-(1S,2S)-U-50488 hydrochloride hydrate

form

powder

form

powder

form

powder

form

solid

color

white to beige

color

white to beige

color

white to beige

color

white

solubility

DMSO: 2 mg/mL, clear

solubility

DMSO: 2 mg/mL, clear

solubility

-

solubility

H2O: 13 mg/mL

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

2-8°C

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

-

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Biochemistry and structural studies of kynurenine 3-monooxygenase reveal allosteric inhibition by Ro 61-8048
Faseb Journal, 32, 2036-2045 (2018)
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)
Susanna Campesan et al.
Current biology : CB, 21(11), 961-966 (2011-06-04)
Neuroactive metabolites of the kynurenine pathway (KP) of tryptophan degradation have been implicated in the pathophysiology of neurodegenerative disorders, including Huntington's disease (HD) [1]. A central hallmark of HD is neurodegeneration caused by a polyglutamine expansion in the huntingtin (htt)
Marta Amaral et al.
Nature, 496(7445), 382-385 (2013-04-12)
Inhibition of kynurenine 3-monooxygenase (KMO), an enzyme in the eukaryotic tryptophan catabolic pathway (that is, kynurenine pathway), leads to amelioration of Huntington's-disease-relevant phenotypes in yeast, fruitfly and mouse models, as well as in a mouse model of Alzheimer's disease. KMO
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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