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(S)-Lisofylline
inactive optical enantiomer of (R)-LSF, an anti-inflammatory agent

Catalog No.C4161
Size Price Stock Qty
1mg
$63.00
In stock
5mg
$283.00
In stock
10mg
$502.00
In stock

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Sample solution is provided at 25 µL, 10mM.

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Quality Control & MSDS

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Chemical structure

(S)-Lisofylline

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Chemical Properties

Cas No. 100324-80-9 SDF Download SDF
Synonyms (+)-Lisofylline,(S)-LSF
Chemical Name 3,7-dihydro-1-[5S-hydroxyhexyl]-3,7-dimethyl-1H-purine-2,6-dione
Canonical SMILES O=C(N(C)C1=C2N(C)C=N1)N(CCCC[[email protected]@H](O)C)C2=O
Formula C13H20N4O3 M.Wt 280.3
Solubility Soluble in DMSO Storage Store at -20°C
Shipping Condition Evaluation sample solution : ship with blue ice.All other available size: ship with RT , or blue ice upon request
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.

Background

Lisofylline (LSF) is a potent anti-inflammatory agent. LSF is a chiral metabolite of pentoxifylline [1]. Pentoxifylline is exclusively reduced to (S)-LSF in the cytosol when metabolized by isolated human liver cells [2].

In vitro: Lisofylline preserved β-cell insulin secretion and inhibited DNA damage of islets in the presence of IL-1β [3]. Simultaneous application of LSF and cytokines to INS-1 cells restored insulin secretion, mitochondrial membrane potential, MTT metabolism, and cell viability to control levels. LSF increased β-cell MTT metabolism as well as insulin release and glucose responsiveness [4].

In vivo: In rats subjected to hemorrhagic shock and resuscitation, LSF increased the intestinal and hepatic blood flow. Treatment with LSF (15 mg/kg) ameliorated the development of mucosal damage and hyperpermeability. Rats treated with LSF showed lower plasma concentrations of the intracellular hepatic enzyme, aspartate aminotransferase. LSF treatment increased concentrations of adenosine triphosphate in intestinal and hepatic tissue [1]. In NOD mice, lisofylline suppressed IFN-γ production, reduced the onset of insulitis and diabetes, and inhibited diabetes after transfer of splenocytes from Lisofylline-treated donors to NOD.scid recipients [3].

References:
[1] Wattanasirichaigoon S, Menconi M J, Fink M P.  Lisofylline ameliorates intestinal and hepatic injury induced by hemorrhage and resuscitation in rats[J]. Critical care medicine, 2000, 28(5): 1540-1549.
[2] Lillibridge, J. A.,Kalhorn, T.F. and Slattery, J.T. Metabolism of lisofylline and pentoxifylline in human liver microsomes and cytosol. Drug Metabolism and Disposition 24(11), 1174-1179 (1996).
[3] Yang Z D, Chen M, Wu R, et al.  The anti-inflammatory compound lisofylline prevents Type I diabetes in non-obese diabetic mice[J]. Diabetologia, 2002, 45(9): 1307-1314.
[4] Chen M, Yang Z, Wu R, et al.  Lisofylline, a novel antiinflammatory agent, protects pancreatic β-cells from proinflammatory cytokine damage by promoting mitochondrial metabolism[J]. Endocrinology, 2002, 143(6): 2341-2348.