(R)-Lisofylline

Names

[ 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

The content on this webpage is sourced from various professional data sources. If you have any questions or concerns regarding the content, please feel free to contact service1@chemsrc.com.