Lipids

Phosphatidylinositol 4,5-bisphosphate diC8 (PI(4,5)P2 diC8) is a synthetic, purified dioctanoyl PI(4,5)P2. Phosphoinositides (PIPns) are minor components of cellular membranes but are integral signaling molecules for cellular communication. Phosphatidylinositol 4,5-bisphosphate (PIP2) has been shown to play a central role in a variety of cellular functions. Amongst its many functions, PIP2 is a substrate for Phospholipase C-coupled G-protein pathways involved in intracellular calcium release in a number of tissues and is also a substrate for class I phosphoinositide 3-kinase (PI3-K).

Sphingosine 1-phosphate (S1P) is a bioactive lysophospholipid formed by phosphorylation of sphingosine by sphingosine kinases. S1P binds to five G-protein coupled receptors designated S1P1-5 leading to cell proliferation, motility, and has a role in regulation cell shape. In addition, S1P acts as an intracellular mediator in a receptor-independent manner regulating cell survival and Ca2+ homeostasis. Sphingosine 1-phosphate fluorescein is a S1P analog with natural erythro stereochemistry labeled at the terminus of the alkyl chain with fluorescein.

Phosphatidylethanol (PEth) is formed primarily by transphosphatidylation of phosphatidylcholine (PC) by phosphlipase D. Most PEth (about 75%) is incorporated into erythrocyte membranes, and is one of the longest-lived circulating EtOH metabolite yet identified. 1-Palmitoyl-2-oleoyl-sn-glycero-3-phosphoethanol-d5 (d5-POPEth) has a fully deuterated ethanol headgroup and can be used as a mass spectrometry standard.

Cardiolipin (CL) is an important component in prokaryotic and in eukaryotic inner mitochondrial membrane. In humans, CL is made by cardiolipin synthase from phosphatidylglycerol and cytidinediphosphatediacylglycerol. Due to its four acyl chains and small head group, CL can organize into domains which can be proton sinks, fill cavities at protein interfaces, stabilize protein oligomers, and participate in high-curvature membrane regions. Autoantibodies to CL have been found in patients with anti-phospholipid syndrome and lupus.

1-Palmitoyl-2-oleoyl-sn-glycero-3-phosphoethanol (POPEth) is a form of phosphatidylethanol (PEth), which 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. POPEth is a one of five most abundant naturally occurring PEth species.