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857393P

Avanti

THI

2-acetyl-5-tetrahydroxybutyl imidazole, powder

Sinónimos:

2-acetyl-4-tetrahydroxybutyl imidazole; 2-acetyl-4(5)-tetrahydroxybutyl imidazole; 2-ATHBI

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About This Item

Fórmula empírica (notación de Hill):
C9H14N2O5
Número de CAS:
94944-70-4
Peso molecular:
230.22
MDL number:
MFCD18427707
UNSPSC Code:
12352211
NACRES:
NA.25

assay

>98% (TLC)

form

powder

packaging

pkg of 1 × 1 mg (857393P-1mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand 857393P

lipid type

sphingolipids
bioactive lipids

shipped in

dry ice

storage temp.

−20°C

SMILES string

[nH]1c(ncc1[C@@H](O)[C@H](O)[C@H](O)CO)C(=O)C

InChI

1S/C9H14N2O5/c1-4(13)9-10-2-5(11-9)7(15)8(16)6(14)3-12/h2,6-8,12,14-16H,3H2,1H3,(H,10,11)/t6-,7-,8-/m1/s1

InChI key

CQSIXFHVGKMLGQ-BWZBUEFSSA-N

General description

2-Acetyl-5-tetrahydroxybutyl imidazole (THI) is an inhibitor of sphingosine-1-phosphate lyase (S1P lyase).
Sphingosine-1-phosphate (S1P) lyase catalyzes the irreversible decomposition of S1P to hexadecanaldehyde and phosphoethanolamine. 2-Acetyl-5-tetrahydroxybutyl imidazole (THI) is an inhibitor of S1P lyase. Because S1P lyase is primarily expressed in lymphatic tissue, treatment of mice with THI (50 μg/ml in drinking water) increases lymphoid tissue S1P concentrations 100-fold, reducing lymphocyte egress from thymus and peripheral lymphoid organs. The resulting lymphopenia is reversible following cessation of THI treatment. Reducing S1P lyase activity results in therapeutic levels of immunosuppression without the non-lymphoid lesions that result from synthetic S1P receptor agonists.

Biochem/physiol Actions

2-Acetyl-5-tetrahydroxybutyl imidazole (THI) can block S1P lyase in vivo and up-regulates circulatory and tissue S1P levels. It has the ability to repress dystrophic muscle degeneration.

Packaging

5 mL Amber Glass Screw Cap Vial (857393P-1mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Emigration of mature T cells from the thymus is inhibited by the imidazole-based compound 2-acetyl-4-tetrahydroxybutylimidazole.
Gugasyan R, et al.
Immunology, 93, 398-404 (1998)
The immunosuppressive compound 2-acetyl-4-tetrahydroxybutyl imidazole inhibits the allogeneic mixed lymphocyte reaction by sequestration of a recirculating subpopulation of T cells.
Bradbury MG, et al.
Immunology, 87, 80-85 (1996)
2-Acetyl-5-tetrahydroxybutyl imidazole (THI) protects 661W cells against oxidative stress
Fabiani C, et al.
Naunyn-Schmiedeberg'S Archives of Pharmacology, 390(7), 741-751 (2017)
Lymphocyte sequestration through S1P lyase inhibition and disruption of S1P gradients.
Schwab SR, et al.
Science, 309, 1735-1739 (2005)
Molecular mechanism of sphingosine-1-phosphate action in Duchenne muscular dystrophy
Nguyen TDH, et al.
Disease models & mechanisms, 7(1), 41-54 (2014)
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