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857393 | THI

2-acetyl-5-tetrahydroxybutyl imidazole

THI

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THI

2-acetyl-5-tetrahydroxybutyl imidazole

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).
Data
Hygroscopic
No
Light Sensitive
No
Molecular Formula
C9H14N2O5
Percent Composition
C 46.95%, H 6.13%, N 12.17%, O 34.75%
Purity
>98%
Stability
1 Years
Storage Temperature
-20°C
CAS Number
94944-70-4
CAS Registry Number is a Registered Trademark of the American Chemical Society
Formula Weight
230.218
Exact Mass
230.09
Synonyms
2-acetyl-4-tetrahydroxybutyl imidazole2-acetyl-4(5)-tetrahydroxybutyl imidazole
2-ATHBI
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References

Schwab SR, Pereira JP, Matloubian M, Xu Y, Huang Y, Cyster JG. Lymphocyte sequestration through S1P lyase inhibition and disruption of S1P gradients. Science. 2005 Sep 9;309(5741):1735-9. doi: 10.1126/science.1113640. PMID: 16151014.

 PubMed ID: 16151014

Gugasyan R, Coward A, O'Connor L, Shortman K, Scollay R. Emigration of mature T cells from the thymus is inhibited by the imidazole-based compound 2-acetyl-4-tetrahydroxybutylimidazole. Immunology. 1998 Mar;93(3):398-404. doi: 10.1046/j.1365-2567.1998.00434.x. PMID: 9640251; PMCID: PMC1364089.

 PubMed ID: 9640251

Bradbury MG, Doherty KV, Parish CR, Lyons AB. The immunosuppressive compound 2-acetyl-4-tetrahydroxybutyl imidazole inhibits the allogeneic mixed lymphocyte reaction by sequestration of a recirculating subpopulation of T cells. Immunology. 1996 Jan;87(1):80-5. PMID: 8666439; PMCID: PMC1383971.

 PubMed ID: 8666439

Vogel P, Donoviel MS, Read R, Hansen GM, Hazlewood J, Anderson SJ, Sun W, Swaffield J, Oravecz T. Incomplete inhibition of sphingosine 1-phosphate lyase modulates immune system function yet prevents early lethality and non-lymphoid lesions. PLoS One. 2009;4(1):e4112. doi: 10.1371/journal.pone.0004112. Epub 2009 Jan 1. PMID: 19119317; PMCID: PMC2606024.

 PubMed ID: 19119317
Certificates of Analysis

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