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Join us! · InformexUSA 2012 · New Orleans, Louisiana · February 14-17, 2012 · Booth 2514

2-Acetyl-5-tetrahydroxybutyl Imidazole

Cayman Chemical Item Number 13222

THI; 2-ATHBI; 2-Acetyl-4-tetrahydroxybutyl Imidazole (CAS 94944-70-4)

2-Acetyl-5-tetrahydroxybutyl Imidazole (CAS 94944-70-4)

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Description

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.1 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.1,2 The resulting lymphopenia is reversible following cessation of THI treatment.3 Reducing S1P lyase activity results in therapeutic levels of immunosuppression without the non-lymphoid lesions that result from synthetic S1P receptor agonists.4

1 Schwab, S.R., Pereira, J.P., Matloubian, M., et al. Lymphocyte sequestration through S1P lyase inhibition and disruption of S1P gradients. Science 309 1735-1739 (2005).

2 Gugasyan, R., Coward, A., O'Connor, L., et al. Emigration of mature T cells from the thymus is inhibited by the imidazole-based compound 2-acetyl-4-tetrahydroxybutylimidazole. Immunology 93 398-404 (1998).

3 Bradbury, M.G., Doherty, K.V., Parish, C.R., et al. The immunosuppressive compound 2-acetyl-4-tetrahydroxybutyl imidazole inhibits the allogeneic mixed lymphocyte reaction by sequestration of a recirculating subpopulation of T cells. Immunology 87 80-85 (1996).

4 Vogel, P., Donoviel, M.S., Read, R., et al. Incomplete inhibition of sphingosine 1-phosphate lyase modulates immune system function yet prevents early lethality and non-lymphoid lesions. PLoS One 4(1) (2009).

Synonyms
  • THI
  • 2-ATHBI
  • 2-Acetyl-4-tetrahydroxybutyl Imidazole
Formal Name 1-​[5-​[(1R,​2S,​3R)-​1,​2,​3,​4-​tetrahydroxybutyl]-​1H-​imidazol-​2-​yl]-​ethanone
CAS Number 94944-70-4
Molecular Formula C9H14N2O5
Formula Weight 230.2
Formulation A crystalline solid
Purity ≥95%
λmax 288 nm
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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CC(=O)​c1ncc([C@@H]​(O)​[C@H]​(O)​C(O)​CO)​[nH]​1

Background Reading

Schwab, S.R., Pereira, J.P., Matloubian, M., et al. Lymphocyte sequestration through S1P lyase inhibition and disruption of S1P gradients. Science 309 1735-1739 (2005).

Bradbury, M.G., Doherty, K.V., Parish, C.R., et al. The immunosuppressive compound 2-acetyl-4-tetrahydroxybutyl imidazole inhibits the allogeneic mixed lymphocyte reaction by sequestration of a recirculating subpopulation of T cells. Immunology 87 80-85 (1996).

Vogel, P., Donoviel, M.S., Read, R., et al. Incomplete inhibition of sphingosine 1-phosphate lyase modulates immune system function yet prevents early lethality and non-lymphoid lesions. PLoS One 4(1) (2009).

Gugasyan, R., Coward, A., O'Connor, L., et al. Emigration of mature T cells from the thymus is inhibited by the imidazole-based compound 2-acetyl-4-tetrahydroxybutylimidazole. Immunology 93 398-404 (1998).

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2-Acetyl-5-tetrahydroxybutyl Imidazole is available in the following screening library:

Size Price Quantity Subtotal
500 µg $51.00 $0.00
1 mg $97.00 $0.00
5 mg $408.00 $0.00
10 mg $714.00 $0.00
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Cart Total $0.00

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Pricing updated 2012-02-10. Prices are subject to change without notice.

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Warning This product is not for human or veterinary use.

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