Lisofylline
Chemical compound
From Wikipedia, the free encyclopedia
Lisofylline (LSF) is a synthetic small molecule with novel anti-inflammatory properties. LSF can effectively prevent type 1 diabetes in preclinical models and improves the function and viability of isolated or transplanted pancreatic islets. It is a metabolite of pentoxifylline.
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| Other names | 1-(5-Hydroxyhexyl)-3,7-dimethylxanthine (HDX) |
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| Formula | C13H20N4O3 |
| Molar mass | 280.328 g·mol−1 |
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As well, LSF improves cellular mitochondrial function and blocks interleukin-12 (IL-12) signaling and STAT-4 activation in target cells and tissues. IL-12 and STAT-4 activation are important pathways linked to inflammation and autoimmune damage to insulin producing cells. Therefore, LSF and related analogs could provide a new therapeutic approach to prevent or reverse type 1 diabetes. LSF also directly reduces glucose-induced changes in human kidney cells suggesting that LSF and analogs have the potential to treat the complications associated with diabetes.
Synthesis
The R enantiomer of the pentoxyfylline analogue in which the ketone has been reduced to an alcohol shows enhanced activity as an inhibitor of acetyl CoA over the parent drug.
For analogs see:[8]
Further reading
- DE 3942872, Aretz, Werner; Furrer, Harald & Gebert, Ulrich et al., "Verfahren zur enantioselektiven Darstellung von (ω-1)-Hydroxyalkylxanthinen [Method for the enantioselective preparation of(ω-1)-hydroxyalkylxanthines]", published 1991-06-27, assigned to Hoechst AG
- US 5310666, Aretz, Werner; Furrer, Harald & Gebert, Ulrich et al., "Process for the enantioselective preparation of (β-1)-hydroxyalkylxanthines by reduction using Rhodotorula rubra", published 1994-05-10, assigned to Hoechst AG
- WO 9531450, Klein, J. Peter; Leigh, Alistair J. & Michnick, John et al., "Asymmetric synthesis of chiral secondary alcohols", published 1995-11-23, assigned to Cell Therapeutics Inc.