Abstract
The thermotropic behavior of three fluorinated phospholipids has been studied by means of high-sensitivity differential scanning calorimetry. The three lipids are 1,2-di(X,X-difluoromyristovyl)phosphatidylcholine with X = 4,8, or 12. The compound with X = 4 has a higher transition temperature than dimyristoylphosphatidylcholine whereas the other two have lower values. All three lipids have transition enthalpies approximately twice that of the unsubstituted lipid. It was found the substituted lipids form strikingly nonideal mixtures with the parent compound. In view of these observations it is evident that results obtained using these or related compounds as probes of bilayer or membrane behavior must be interpreted with due caution. Some of the properties exhibited by geminal fluorine atoms in fluorinated phospholipids appear to be similar to those of cis double bonds in lipids.
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Selected References
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- Albon N., Sturtevant J. M. Nature of the gel to liquid crystal transition of synthetic phosphatidylcholines. Proc Natl Acad Sci U S A. 1978 May;75(5):2258–2260. doi: 10.1073/pnas.75.5.2258. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Barton P. G., Gunstone F. D. Hydrocarbon chain packing and molecular motion in phospholipid bilayers formed from unsaturated lecithins. Synthesis and properties of sixteen positional isomers of 1,2-dioctadecenoyl-sn-glycero-3-phosphorylcholine. J Biol Chem. 1975 Jun 25;250(12):4470–4476. [PubMed] [Google Scholar]
- Birdsall N. J., Lee A. G., Levine Y. K., Metcalfe J. C. 19 F NMR of monofluorostearic acids in lecithin vesicles. Biochim Biophys Acta. 1971 Aug 13;241(2):693–696. doi: 10.1016/0005-2736(71)90069-1. [DOI] [PubMed] [Google Scholar]
- Brockerhoff H., Yurkowski M. Simplified preparation of L-alpha-glyceryl phosphoryl choline. Can J Biochem. 1965 Oct;43(10):1777–1777. doi: 10.1139/o65-197. [DOI] [PubMed] [Google Scholar]
- Dahlquist F. W., Muchmore D. C., Davis J. H., Bloom M. Deuterium magnetic resonance studies of the interaction of lipids with membrane proteins. Proc Natl Acad Sci U S A. 1977 Dec;74(12):5435–5439. doi: 10.1073/pnas.74.12.5435. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Gent M. P., Armitage I. M., Prestegard J. H. 19F nuclear magnetic resonance studies of lipid bilayer systems. I. J Am Chem Soc. 1976 Jun 23;98(13):3749–3755. doi: 10.1021/ja00429a002. [DOI] [PubMed] [Google Scholar]
- Gent M. P., Cottam P. F., Ho C. Fluorine-19 nuclear magnetic resonance studies of Escherichia coli membranes. Proc Natl Acad Sci U S A. 1978 Feb;75(2):630–634. doi: 10.1073/pnas.75.2.630. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Gent M. P., Ho C. Fluorine-19 nuclear magnetic resonance studies of lipid phase transitions in model and biological membranes. Biochemistry. 1978 Jul 25;17(15):3023–3038. doi: 10.1021/bi00608a014. [DOI] [PubMed] [Google Scholar]
- Ladbrooke B. D., Williams R. M., Chapman D. Studies on lecithin-cholesterol-water interactions by differential scanning calorimetry and X-ray diffraction. Biochim Biophys Acta. 1968 Apr 29;150(3):333–340. doi: 10.1016/0005-2736(68)90132-6. [DOI] [PubMed] [Google Scholar]
- Longmuir K. J., Capaldi R. A., Dahlquist F. W. Nuclear magnetic resonance studies of lipid-protein interactions. A model of the dynamics and energetics of phosphatidylcholine bilayers that contain cytochrome c oxidase. Biochemistry. 1977 Dec 27;16(26):5746–5755. doi: 10.1021/bi00645a015. [DOI] [PubMed] [Google Scholar]
- Mabrey S., Sturtevant J. M. Investigation of phase transitions of lipids and lipid mixtures by sensitivity differential scanning calorimetry. Proc Natl Acad Sci U S A. 1976 Nov;73(11):3862–3866. doi: 10.1073/pnas.73.11.3862. [DOI] [PMC free article] [PubMed] [Google Scholar]