The four tocopherols (α, β, .delta., and γ) and four tocotrienols (α, β, .delta., and γ) are forms of vitamin E, which is known for its antioxidant activity. Tocotrienols are found at high concentrations in palm oil and rice bran. Recent studies show tocotrienols…

An alkaloid metabolite of nicotine as well as a major product of its pyrolysis; binds comparably to CYP2A6 and CYP2A13 (Kis = 7.5 and 5.6 µM, respectively), but appears to more effectively inactivate CYP2A6.

11β-PGF2α-EA is the theoretical hepatic metabolite of PGD2-EA, produced during COX-2 metabolism of the endogenous cannabinoid AEA which is found in brain, liver, and other mammalian tissues. AEA can be used directly by COX-2 and specific PG synthase to produce ethanolamide congeners of…

A metabolite of lipoxygenase-mediated oxidation of DPA; activates Nrf2-dependent antioxidant gene expression, acts as a PPARγ agonist (EC₅₀ = ~200 nM), and inhibits pro-inflammatory cytokine and nitric oxide production at biological concentration ranges (5-25 µM).

An internal standard for the quantification of DHA by GC- or LC-MS.

A water soluble prodrug analog of AEA with similar activity to that of AEA in the growth inhibition of C6 glioma cells; also a structural variant of LPA, however, its effects on the various LPA receptors have not been tested.

Thioetheramide-PC is a structurally modified phospholipid that functions as a competitive, reversible inhibitor of sPLA2. The IC₅₀ value for thioetheramide-PC is 2 µM at a substrate concentration of 0.5 mM. In addition to binding to the catalytic site of sPLA2, thioetheramide-PC…

Initiates glycogen synthesis in hepatocytes by causing inactivation of phosphorylase a and activation of glycogen synthase a (maximal effects with ~20 µM Itu); potent inhibitor of ERK2 (Ki = 525 nM).

A reversible, competitive thrombin inhibitor (Ki = 5 nM) that shows selectivity for thrombin over other clotting pathway enzymes.

Modified with a carboxylic acid group terminating the C-16 alkyl chain, providing a convenient site for chemical crosslinking.

Oleyloxyethyl phosphorylcholine is an inhibitor of PLA2 with an IC₅₀ value of 6.2 µM for porcine pancreatic PLA2.

An EPA-containing MAG amide analog that inhibits the growth of human lung carcinoma A549 cells, producing 98.4% growth inhibition when applied at 3 µM; an analog of EPEA, a natural N-acylethanolamide that impacts aging and inflammation.

Linolein hydroperoxides are a mixture of 132 possible isomers of mono-, di-, and tri-hydroperoxides produced from the autoxidation of trilinolein. Autoxidation of linoleic acid containing triglycerides (for example, trilinolein) in vivo could result in the formation of these hydroperoxides. Unlike…

A potent and selective agonist of the human PGE2 receptor, EP4 with a Ki value of 0.38 nM and an EC50 value of 0.6 nM; induces thermal hyperalgesia when injected into guinea pig forepaw and increases vasodilation of human pulmonary vein.

(+)-15(R)-Fluprostenol isopropyl ester is a prodrug (Travoprost) which is converted by esterase enzymatic activity in the cornea to yield the corresponding free acid. The free acid, (+)-15(R)-fluprostenol, is a potent FP receptor agonist. The 15(R)-epimers of most PGs are about 100 times less…

A minor impurity produced in the synthesis of (+)-cloprostenol; 20-fold less active than (+)-cloprostenol in terminating pregnancy in the hamster.

An ester of the free acid that is less water soluble, but more amenable for the formulation of stearidonate-containing diets and dietary supplements.

A homolog of LOEA, characterized by the addition of an (S)-α-methyl group at the methylene carbon adjacent to the amide nitrogen.

A natural monoacylglycerol that is metabolized by monoacylglycerol lipase; an agonist of GPR119 (EC₅₀ = 2.5 µM), stimulating the release of glucagon-like peptide-1 from intestinal L-cells.

Unnatural C-15 epimer of Travoprost.

Travoprost is the Alcon trade name for fluprostenol isopropyl ester, an F-series prostaglandin analog which has been approved for use as an ocular hypotensive drug. Fluprostenol isopropyl ester is a prodrug which is converted by esterase enzymatic activity in the cornea to yield the corresponding…

PPHP is a substrate for the measurement of peroxidase enzymes. PPHP has been used to quantitate the peroxidase activity of COX-1 and COX-2.

5(Z),11(Z),14(Z)-Eicosatrienoic acid is a PUFA found in various natural sources including maritime pine (Pinus pinaster) seed oil (MPSO), gymnospermae leaves and seeds, and freshwater gastropods. A diet containing MPSO lowered HDL and ApoA1 levels in transgenic mice expressing human ApoA1. MPSO was…

DAN-1 EE is a fluorescent indicator for the bioimaging of NO. DAN-1 EE is a cell permeable derivative of DAN, a molecule which has been used extensively in the quantitation of nitrate and nitrite using fluorescence spectroscopy. Upon entry into the cell, DAN-1 EE is transformed into the less cell…

13(S)-HODE is the LO metabolite of linoleic acid. 13(S)-HODE modulates the PAF, LTB4, and fMLP-induced calcium influx in human PMNL. The mechanism by which 13(S)-HODE elicits its inhibitory effect is still unclear. The use of biotinylated 15(S)-HETE as a probe for detecting binding proteins and/or…

A potent inhibitor of HCV infection (EC₅₀ = 17 nM) that displays low cytotoxicity of virally-infected human hepatoma Huh7.5.1 cells (CC₅₀ = 21.3 µM); displays good pharmacokinetics in mice when delivered intraperitoneally, with preferential liver distribution without…

An internal standard for the quantification of OEA by GC- or LC-MS.

A homolog of DHEA, characterized by the addition of an (S)-β-methyl group at the terminal ethanolamine carbon.

An isomer of Vitamin E that has less potent antioxidant properties than α-tocotrienol.

The product of nitration of linoleate by NO-derived reactive species; activates PPARγ (Ki = 133 nM), inducing CD36 expression in macrophages, adipocyte differentiation, and glucose uptake; can also be metabolized to produce nitrite derivatives which in turn form NO, leading to increased cGMP production.

An endocannabinoid analog that does not bind to CB1, CB2, or TRPV1; at 5 mg/kg antagonizes the hypotensive effects of a 10 mg/kg IV bolus of abnormal cannabidiol (Abn-CBD) in an anesthetized rat blood pressure model; relaxes isolated rat mesenteric arteries and abdominal aorta, and increases the…

A homolog of DHEA, characterized by the addition of an (R)-β-methyl group at the terminal ethanolamine carbon.