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• W2013517198 abstract "The synthesis and characterization of spin-labeled phospholipids (SLP)—derivatives of 1,2-dipalmitoyl-sn-glycero-3-phosphothioethanol (PTE)—with pH-reporting nitroxides that are covalently attached to the lipid’s polar headgroup are being reported. Two lipids were synthesized by reactions of PTE with thiol-specific, pH-sensitive methanethiosulfonate spin labels methanethiosulfonic acid S-(1-oxyl-2,2,3,5,5-pentamethylimidazolidin-4-ylmethyl) ester (IMTSL) and S-4-(4-(dimethylamino)-2-ethyl-5,5-dimethyl-1-oxyl-2,5-dihydro-1H-imidazol-2-yl)benzyl methanethiosulfonate (IKMTSL). The pKa values of the IMTSL−PTE lipid measured by EPR titration in aqueous buffer/isopropyl alcohol solutions of various compositions were found to be essentially the same (pKa ≈ 2.35), indicating that in mixed aqueous/organic solvents, the amphiphilic lipid molecules could be shielded from changing bulk conditions by a local shell of solvent molecules. To overcome this problem, the spin-labeled lipids were modeled by synthesizing IMTSL- and IKMTSL−2-mercaptoethanol adducts. These model compounds yielded the intrinsic pKa0’s for IMTSL−PTE and IKMTSL−PTE in aqueous buffers as 3.33 ± 0.03 and 5.98 ± 0.03, respectively. A series of EPR titrations of IMTSL−PTE in mixed water/isopropyl alcohol solution allowed for calibrating the polarity-induced pKa shifts, ΔpKapol, vs bulk solvent dielectric permittivity. These calibration data allowed for estimating the local dielectric constant, εeff, experienced by the reporter nitroxide of the IMTSL−PTE lipid incorporated into the nonionic Triton X-100 micelles as 60 ± 5 and 57 ± 5 at 23 and 48 °C, respectively. For micelles formed from an anionic surfactant sodium dodecyl sulfate (SDS) the electrostatic-induced pKa shift, ΔpKael = 2.06 ± 0.04 units of pH, was obtained by subtracting the polarity-induced contribution. This shift yields Ψ = −121 mV electric potential of the SDS micelle surface." @default.
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• W2013517198 date "2009-02-23" @default.
• W2013517198 modified "2023-10-10" @default.
• W2013517198 title "Spin-Labeled pH-Sensitive Phospholipids for Interfacial p<i>K</i>_a Determination: Synthesis and Characterization in Aqueous and Micellar Solutions" @default.
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• W2013517198 doi "https://doi.org/10.1021/jp810993s" @default.
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