Lipids

Phosphatidylethanol (PEth) is formed primarily by transphosphatidylation of phosphatidylcholine (PC) by phospholipase D. Most PEth (about 75%) is incorporated into erythrocyte membranes and is one of the longest-lived circulating EtOH metabolite yet identified. BODIPY-FL Phosphatidylethanol (BODIPY-FL PEth) is a novel flourescent phospholipid analog of this intriguing and rare lipid found in nature.

Phosphatidylethanol (PEth) is formed primarily in the liver by transphosphatidylation of phosphatidylcholine (PC) by phospholipase D. PEth is associated with lipoprotein particles VLDL and HDL transferred between lipoproteins and PEth-lipoprotein complexes may have a protective effect against atherogenesis by promoting VEGF secretion by SMC and endothelium.  Most PEth (about 75%) is incorporated into erythrocyte membranes and is the longest-lived circulating EtOH metabolite yet identified.  NBD-Phosphatidylethanol (NBD-PEth) is a novel flourescent phospholipid analog of this intriguing and rare lipid found in nature.

Thio-ccPA is a stabilized analogue of carbacyclic phosphatidic acid (ccPA). It inhibits the lysoPLD activity of Autotaxin (ATX) and acts as an LPA1/3 receptor antagonist. Thio-ccPA decreases the viability of B16F10 A375 and MeWo melanoma cell lines. Addition of endogenous LPA did not reverse these effects in B16F10 cells. Thio-ccPA decreased the number of pulmonary and non-pulmonary metastases in a B16F10 metastatic melanoma mouse model.

Oleoyl 3-carbacyclic Phosphatidic Acid (ccPA) is an analog of naturally occurring cyclic phosphatidic acid in which the sn-3 oxygen has been replaced with carbon making a stable phosphonate with is resistant to ring opening. ccPA is an analog of LPA but does not activate the LPA1-4 receptors. It also acts as a potent inhibitor of Autotaxin and can inhibit the metastasis of B16-F10 melanoma cells when injected into mice.;References1) Baker D. L. et al. "Carba Analogs of Cyclic Phosphatidic Acid Are Selective Inhibitors of Autotaxin and Cancer Cell Invasion and Metastasis” J. Biol. Chem. 2006 281 22786.2) Uchiyama A. et al. “Inhibition of transcellular tumor cell migration and metastasis by novel carba-derivatives of cyclic phosphatidic acid.” Biochim. Biophys. Acta 2007 1771 103.3) Williams J. R. et al “Unique ligand selectivity of the GPR92/LPA5 lysophosphatidate receptor indicates role in human platelet activation” J. Biol. Chem. 2009 284 17304.

Monocaprin is a derivative of cycloartane that was originally isolated from the trunk bark of Monocarpia marginalis. Cycloartane triterpenoids are of interest for their potential anti-inflammatory and immune system modulation properties.

Monolaurin is a monoglyceride mono-ester formed from glycerol and lauric acid. Monolaurin has shown antibacterial and antiviral effects when examined in vitro.  Its usefulness in clinical settings is currently under investigation.

Monomyristin aka rac-glycerol 1-myristate or glycerol α-monomyristate is used as a nonionic surfactant in the development of micelles in colloidal chemistry. Monomyristin has antibacterial activity against several Gram-positive bacterial strains.

Ether C12 Lysobisphosphatidic acid ((R R)-2 2’-Bisdodecyl-LBPA ammonium salt) is an ether analog of the naturally occurring biologically active isomer of LPBA.Lysobisphosphatidic acids (LBPAs) known also as bis-(monoacylglycerol)phosphates (BMPs) are specialized lipids reported to play a role in intracellular protein and lipid transport in healthy cells. Their accumulation was observed in pathologic liver tissue and they also serve as antigens for auto-antibody generation in a human autoimmune condition termed antiphospholipid syndrome. Accumulation of LBPAs in intracellular often multilamellar membranes is related to biomembrane polymorphism which may impact intracellular cholesterol transport.

Ether C18 Lysobisphosphatidic acid ((S S)-2 2’-Bisoctadecyl-LBPA ammonium salt) is an ether analog of the naturally occurring biologically active isomer of LPBA.Lysobisphosphatidic acids (LBPAs) known also as bis-(monoacylglycerol)phosphates (BMPs) are specialized lipids reported to play a role in intracellular protein and lipid transport in healthy cells. Their accumulation was observed in pathologic liver tissue and they also serve as antigens for auto-antibody generation in a human autoimmune condition termed antiphospholipid syndrome. Accumulation of LBPAs in intracellular often multilamellar membranes is related to biomembrane polymorphism which may impact intracellular cholesterol transport.