N lauroyl d erythro sphinganylphosphorylcholine

The synthesis of the polyphenols used in this study has been described previously by us (18 (link)). N-[(1R,2S)-2-Hydroxy-1-hydroxymethyl-2-(2-tridecyl-1-cyclopropenyl)ethyl]octanamide (GT-11) was synthesized as described previously (41 (link)). Stock solutions of polyphenols and GT-11 were prepared at 10 mM in dimethyl sulfoxide (DMSO). N-Lauroyl-d-erythro-sphinganylphosphorylcholine, a synthetic dhSM, was purchased from Avanti Polar Lipids Inc. (Birmingham, AL) and dissolved in ethanol to create a 50 mM stock solution. N-{6-[(7-Nitro-2-1,3-benzoxadiazol-4-yl)amino]hexanoyl}-d-erythro-dihydrosphingosine (dhCerC6NBD) was synthesized as described previously (59 (link)). The same concentration of the drug solvent (DMSO in the case of polyphenols and GT-11 or ethanol in the case of dhSM) was used as the drug vehicle.

Propan-2-one, methanol, 1-butanol, LC-MS grade water, primuline yellow dye, ammonium dihydrogen phosphate, 3,5-Di-tert-4-butylhydroxytoluene (BHT) and ammonium formate were from Sigma-Aldrich (Saint Louis, MO, USA). Ethanol and high performance liquid chromatography (HPLC)-analytical grade chloroform (CHCl₃) were respectively from J.T. Baker (Center Valley, PA, USA) and Carlo Erba (Cornaredo, MI, Italy). N-lignoceroyl-D-erythro-sphingosine (Cer C24:0) 1,2-Dipalmitoyl-sn-Glycero-3-Phosphocholine (DPPC), Cardiolipin (CL), 1,2-Dipalmitoyl-sn-Glycero-3-Phosphoethanolamine (DPPE), D-glucosyl-ß-1,1′-N-stearoyl-D-erythro-sphingosine-d5 (HexCer), N-lauroyl-D-erythro-sphingosine, N-lauroyl-D-erythro-sphinganine, N-lauroyl-D-erythro-sphingosylphosphorylcholine N-lauroyl-D-erythro-sphinganylphosphorylcholine, D-glucosyl-ß−1,1′-N-lauroyl-D-erythro-sphingosine, D-lactosyl-ß-1,1′ N-lauroyl-D-erythro-sphingosine and C17 d-erythro-dihydrosphingosine-1-phosphate lipids standards were from Avanti Polar Lipids (Alabaster, Alabama, USA). SL standard mixture, containing SM and Sulfatides (SLF) was from Matreya LLC (Pleasant Gap, PA, USA).