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(R)-Lisofylline

Names

[ CAS No. ]:
100324-81-0

[ Name ]:
(R)-Lisofylline

[Synonym ]:
R-1-(5-Hydroxyhexyl)-3,7-dimethylxanthine
(R)-3,7-Dihydro-1-(5-hydroxyhexyl)-3,7-dimethyl-1H-purine-2,6-dione
Lisophylline
ProTec
1-[(5R)-5-Hydroxyhexyl]-3,7-dimethyl-3,7-dihydro-1H-purine-2,6-dione
Lisofylline
1H-Purine-2,6-dione, 3,7-dihydro-1-(5-hydroxyhexyl)-3,7-dimethyl-, (R)-
1-[(R)-5-Hydroxyhexyl]theobromine
CT 1501R
CT-1501R
1H-Purine-2,6-dione, 3,7-dihydro-1-[(5R)-5-hydroxyhexyl]-3,7-dimethyl-

Biological Activity

[Description]:

(R)-Lisofylline ((R)-Lisophylline) is a (R)-enantiomer of the metabolite of Pentoxifylline with anti-inflammatory properties. (R)-Lisofylline is a lysophosphatidic acid acyltransferase inhibitor with an IC50 of 0.6 µM and interrupts IL-12 signaling-mediated STAT4 activation. (R)-Lisofylline has the potential for type 1 diabetes, autoimmune disorders research[1][2].

[Related Catalog]:

Signaling Pathways >> Stem Cell/Wnt >> STAT
Signaling Pathways >> JAK/STAT Signaling >> STAT
Research Areas >> Inflammation/Immunology
Research Areas >> Metabolic Disease

[Target]

IC50: 0.6 µM (Lysophosphatidic acid acyltransferase)[1] STAT4[1]


[In Vitro]

(R)-Lisofylline blocks IL-12-driven Th1 differentiation and T cell proliferation in vitro, yet has no effect on IL-12 secretion from APCs ex vivo or in vitro[3].

[In Vivo]

(R)-Lisofylline reduces the impairment of insulin secretion induced by IL-1β in cultured rat islet cells, suppresses IFN-γ production, the onset of diabetes, and macrophage infiltration into islets from NOD mice, as well as Lisofylline improves insulin response and lowers glucose levels in Streptozotocin-treated rats after the oral glucose tolerance test[1]. (R)-Lisofylline prevents β cell dysfunction in NOD mice by inhibition of STAT4 phosphorylation which interrupts IL-12 signaling. (R)-Lisofylline ameliorates experimental allergic encephalomyelitis in mice[1]. (R)-Lisofylline also improves survival in mice injected with a lethal dose of LPS and ameliorates sepsis-induced lung injury in minipigs. In rats given IL-1 intratracheally (R)-Lisofylline pretreatment reduces lung leak but does not decrease neutrophil accumulation in lungs[1]. (R)-Lisofylline also suppresses release of TNF-α in vivo in mice and ex vivo in human blood stimulated with endotoxin derived from Salmonella or Escherichia coli[1].

[References]

[1]. Elżbieta Wyska, et al. Physiologically Based Modeling of Lisofylline Pharmacokinetics Following Intravenous Administration in Mice. Eur J Drug Metab Pharmacokinet. 2016 Aug;41(4):403-12.

[2]. B M Hybertson, et al. Lisofylline Prevents Leak, but Not Neutrophil Accumulation, in Lungs of Rats Given IL-1 Intratracheally. J Appl Physiol (1985). 1997 Jan;82(1):226-32.

[3]. J J Bright, et al. Prevention of Experimental Allergic Encephalomyelitis via Inhibition of IL-12 Signaling and IL-12-mediated Th1 Differentiation: An Effect of the Novel Anti-Inflammatory Drug Lisofylline. J Immunol. 1998 Dec 15;161(12):7015-22.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
511.2±56.0 °C at 760 mmHg

[ Molecular Formula ]:
C13H20N4O3

[ Molecular Weight ]:
280.323

[ Flash Point ]:
263.0±31.8 °C

[ Exact Mass ]:
280.153534

[ PSA ]:
82.05000

[ LogP ]:
0.34

[ Vapour Pressure ]:
0.0±1.4 mmHg at 25°C

[ Index of Refraction ]:
1.621

Related Compounds