Effect of dipole moment on amphiphile solubility and partition into liquid ordered and liquid disordered phases in lipid bilayers was written by Cardoso, Renato M. S.;Martins, Patricia A. T.;Ramos, Cristiana V.;Cordeiro, Margarida M.;Leote, Ricardo J. B.;Razi Naqvi, Kalbe;Vaz, Winchil L. C.;Moreno, Maria Joao. And the article was included in Biochimica et Biophysica Acta, Biomembranes in 2020.Reference of 26662-94-2 The following contents are mentioned in the article:
Association of amphiphiles with biomembranes is important for their availability at specific locations in organisms and cells, being critical for their biol. function. A prominent role is usually attributed to the hydrophobic effect, and to electrostatic interactions between charged amphiphiles and lipids. This work explores a closely related and complementary aspect, namely the contribution made by dipole moments to the strength of the interactions established. Two xanthene amphiphiles with opposite relative orientations of their dipole and amphiphilic moments have been selected (Rhodamine-C14 and Carboxyfluorescein-C14). The membranes studied have distinct lipid compositions, representing typical cell membrane pools, ranging from internal membranes to the outer and inner leaflet of the plasma membrane. A comprehensive study is reported, including the affinity of the amphiphiles for the different membranes, the stability of the amphiphiles as monomers and their tendency to form small clusters, as well as their transverse location in the membrane. The orientation of the amphiphile dipole moment, which determines whether its interaction with the membrane dipole potential is repulsive or attractive, is found to exert a large influence on the association of the amphiphile with ordered lipid membranes. These interactions are also responsible for the formation of small clusters or stabilization of amphiphile monomers in the membrane. The results obtained allow understanding the prevalence of protein lipidation at the N-terminal for efficient targeting to the plasma membrane, as well as the tendency of GPI-anchored proteins (usually lipidated at the C-terminal) to form small clusters in the membrane ordered domains. This study involved multiple reactions and reactants, such as (2R,9Z)-1-(((2-Aminoethoxy)(hydroxy)phosphoryl)oxy)-3-(palmitoyloxy)propan-2-yl oleate (cas: 26662-94-2Reference of 26662-94-2).
(2R,9Z)-1-(((2-Aminoethoxy)(hydroxy)phosphoryl)oxy)-3-(palmitoyloxy)propan-2-yl oleate (cas: 26662-94-2) belongs to esters. Esters are widespread in nature and are widely used in industry. In nature, fats are in general triesters derived from glycerol and fatty acids. Esters are responsible for the aroma of many fruits. Esters contain a carbonyl center, which gives rise to 120掳 C鈥揅鈥揙 and O鈥揅鈥揙 angles. Unlike amides, esters are structurally flexible functional groups because rotation about the C鈥揙鈥揅 bonds has a low barrier. Their flexibility and low polarity is manifested in their physical properties; they tend to be less rigid (lower melting point) and more volatile (lower boiling point) than the corresponding amides. Reference of 26662-94-2
Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics