lisofylline   Click here for help

GtoPdb Ligand ID: 9225

Synonyms: (R)-lisophylline | CT-1501R
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Lisophylline is an active metabolite of pentoxifylline. The compound has novel anti-inflammatory properties, likely through inhibition of IL-12 signalling and STAT-4 activation [2]. It is reported to prevent type 1 diabetes in preclinical models [3] and improve the function and viability of isolated or transplanted pancreatic islets [1]. Evidence suggests that combined treatment with lisofylline (for its anti-inflammatory action) and exendin-4 (to enhance beta-cell proliferation) can reverse autoimmune diabetes in the non-obese diabetic (NOD) mouse model [4].
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 82.05
Molecular weight 280.15
XLogP 2.31
No. Lipinski's rules broken 0
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Canonical SMILES CC(CCCCn1c(=O)c2n(C)cnc2n(c1=O)C)O
Isomeric SMILES C[C@H](CCCCn1c(=O)c2n(C)cnc2n(c1=O)C)O
InChI InChI=1S/C13H20N4O3/c1-9(18)6-4-5-7-17-12(19)10-11(14-8-15(10)2)16(3)13(17)20/h8-9,18H,4-7H2,1-3H3/t9-/m1/s1
1. Cui P, Macdonald TL, Chen M, Nadler JL. (2006)
Synthesis and biological evaluation of lisofylline (LSF) analogs as a potential treatment for Type 1 diabetes.
Bioorg Med Chem Lett, 16 (13): 3401-5. [PMID:16650991]
2. Rice GC, Rosen J, Weeks R, Michnick J, Bursten S, Bianco JA, Singer JW. (1994)
CT-1501R selectively inhibits induced inflammatory monokines in human whole blood ex vivo.
Shock, 1 (4): 254-66. [PMID:7735959]
3. Tersey SA, Carter JD, Rosenberg L, Taylor-Fishwick DA, Mirmira RG, Nadler JL. (2012)
Amelioration of type 1 diabetes following treatment of non-obese diabetic mice with INGAP and lisofylline.
J Diabetes Mellitus, 2 (2): 251-257. [PMID:26473085]
4. Yang Z, Chen M, Carter JD, Nunemaker CS, Garmey JC, Kimble SD, Nadler JL. (2006)
Combined treatment with lisofylline and exendin-4 reverses autoimmune diabetes.
Biochem Biophys Res Commun, 344 (3): 1017-22. [PMID:16643856]