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- W2000389519 abstract "A series of synthetic analogs of naturally occurring glycerophospholipids has been studied for gel-to-liquid transition temperature (Tc) by using differential scanning calorimetry. The compounds investigated were dihexadecyl phosphatidylcholine (DHPC) plus 11 newly synthesized phosphonolipids. Six were racemates and have ether-ether fatty chains and 5 were chiral (R) with ether-amide fatty chains bonded to the glycerol moiety; each series also contained a methylene isosteric substitution for one of the oxygen atoms in naturally occurring glycerophospholipid phosphate esters. All analogs have fatty chains of equivalent length in saturated carbon atoms C2C16, but varied in N-headgroup structures. The thermal behaviors of these novel molecules were found to depend upon the degree of alkylation of the headgroups and upon whether the hydrocarbon chains are bonded as ethers or amides. The ether-ether (diether) phosphonolipid (DEPN) analogs of dipalmitoyl phosphatidylcholine (DPPC) and dipalmitoyl phosphatidylethanolamine (DPPE) had increased gel-to-liquid crystal transition temperatures (Tc) compared to their naturally occurring (fatty acyl ester) glycerophospholipid counterparts. In general, DEPN analogs had Tc values 3.7−5.8°C higher than ether-amide phosophonolipid (EAPN) compounds of equivalent headgroup, although EAPN-13 was an exception with the highest Tc of any compound studied. In both the DEPN and EAPN series, analogs with hydrogen atom(s) covalently bonded to the headgroup nitrogen atom showed higher Tc values, possibly related to their increased potential for hydrogen bonding. Interfacial property studies (adsorption, Wilhelmy balance, oscillating bubble) showed that several analogs with higher transitions than DPPC, the principal lung surfactant glycerophospholipid, had improved adsorption and respreading, with equivalent surface tension lowering in compressed spread films on the balance and with minimum surface tensions <1 mN/m in pulsated dispersions on the bubble. Surface activity did not correlate simply with Tc and results suggested that other factors, such as molecular shape (wedge shaped as in phosphatidylethanolamine, PE) or bilayer structure (interdigitated as in DHPC) may be important in understanding dynamic respreading differences in interfacial films compressed dynamically past collapse." @default.
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- W2000389519 date "1992-11-01" @default.
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- W2000389519 title "Differential scanning calorimetry studies of phosphonolipid analogs of lung surfactant glycerophospholipids" @default.
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- W2000389519 doi "https://doi.org/10.1016/0021-9797(92)90075-w" @default.
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