Effects of Diacylglycerols on Conformation of Phosphatidylcholine Headgroups in Phosphatidylcholine/phosphatidylserine Bilayers

Overview

Journal Biophys J

Publisher Cell Press

Specialty Biophysics

Date 1995 Sep 1

PMID 8519996

Citations 5

Authors

E M Goldberg

D S Lester

D B Borchardt

R Zidovetzki

Affiliations

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Abstract

The effects of five diacylglycerols (DAGs), diolein, 1-stearoyl,2-arachidonoyl-sn-glycerol, dioctanoylglycerol, 1-oleoyl,2-sn-acetylglycerol, and dipalmitin (DP), on the structure of lipid bilayers composed of mixtures of phosphatidylcholine and phosphatidylserine (4:1 mol/mol) were examined by 2H nuclear magnetic resonance (NMR). Dipalmitoylphosphatidylcholine deuterated at the alpha- and beta-positions of the choline moiety was used to probe the surface region of the membranes. Addition of each DAG except DP caused a continuous decrease in the beta-deuteron quadrupole splittings and a concomitant increase in the alpha-deuteron splittings indicating that DAGs induce a conformational change in the phosphatidylcholine headgroup. Additional evidence of conformational change was found at high DAG concentrations (> or = 20 mol%) where the alpha-deuteron peaks became doublets indicating that the two alpha-deuterons were not equivalent. The changes induced by DP were consistent with the lateral phase separation of the bilayers into gel-like and fluid-like domains with the phosphatidylcholine headgroups in the latter phase being virtually unaffected by DP. The DAG-induced changes in alpha-deuteron splittings were found to correlate with DAG-enhanced protein kinase C (PK-C) activity, suggesting that the DAG-induced conformational changes of the phosphatidylcholine headgroups are either directly or indirectly related to a mechanism of PK-C activation. 2H NMR relaxation measurements showed significant increase of the spin-lattice relaxation times for the region of the phosphatidylcholine headgroups, induced by all DAGs except DP. However, this effect of DAGs did not correlate with the DAG-induced activation of PK-C.

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References

Jain M, Berg O . The kinetics of interfacial catalysis by phospholipase A2 and regulation of interfacial activation: hopping versus scooting. Biochim Biophys Acta. 1989; 1002(2):127-56. DOI: 10.1016/0005-2760(89)90281-6. View

Browning J . Motions and interactions of phospholipid head groups at the membrane surface. 2. Simple alkyl head groups. Biochemistry. 1981; 20(25):7123-33. DOI: 10.1021/bi00528a012. View

Beschiaschvili G, Seelig J . Melittin binding to mixed phosphatidylglycerol/phosphatidylcholine membranes. Biochemistry. 1990; 29(1):52-8. DOI: 10.1021/bi00453a007. View

Seelig J, Macdonald P, Scherer P . Phospholipid head groups as sensors of electric charge in membranes. Biochemistry. 1987; 26(24):7535-41. DOI: 10.1021/bi00398a001. View

Berridge M . Inositol trisphosphate and diacylglycerol: two interacting second messengers. Annu Rev Biochem. 1987; 56:159-93. DOI: 10.1146/annurev.bi.56.070187.001111. View

LEWIS R, McElhaney R, Harper P, Turner D, Gruner S . Studies of the thermotropic phase behavior of phosphatidylcholines containing 2-alkyl substituted fatty acyl chains: a new class of phosphatidylcholines forming inverted nonlamellar phases. Biophys J. 1994; 66(4):1088-103. PMC: 1275816. DOI: 10.1016/S0006-3495(94)80890-2. View

Roux M, Neumann J, Hodges R, Devaux P, Bloom M . Conformational changes of phospholipid headgroups induced by a cationic integral membrane peptide as seen by deuterium magnetic resonance. Biochemistry. 1989; 28(5):2313-21. DOI: 10.1021/bi00431a050. View

Mayer L, Hope M, Cullis P, Janoff A . Solute distributions and trapping efficiencies observed in freeze-thawed multilamellar vesicles. Biochim Biophys Acta. 1985; 817(1):193-6. DOI: 10.1016/0005-2736(85)90084-7. View

Kishimoto A, Takai Y, Mori T, Kikkawa U, NISHIZUKA Y . Activation of calcium and phospholipid-dependent protein kinase by diacylglycerol, its possible relation to phosphatidylinositol turnover. J Biol Chem. 1980; 255(6):2273-6. View

10.

Ulrich A, Watts A . Molecular response of the lipid headgroup to bilayer hydration monitored by 2H-NMR. Biophys J. 1994; 66(5):1441-9. PMC: 1275864. DOI: 10.1016/S0006-3495(94)80934-8. View

11.

Lapetina E, Reep B, Ganong B, Bell R . Exogenous sn-1,2-diacylglycerols containing saturated fatty acids function as bioregulators of protein kinase C in human platelets. J Biol Chem. 1985; 260(3):1358-61. View

12.

De Boeck H, Zidovetzki R . Interactions of saturated diacylglycerols with phosphatidylcholine bilayers: A 2H NMR study. Biochemistry. 1992; 31(2):623-30. DOI: 10.1021/bi00117a046. View

13.

Macdonald P, Seelig J . Calcium binding to mixed phosphatidylglycerol-phosphatidylcholine bilayers as studied by deuterium nuclear magnetic resonance. Biochemistry. 1987; 26(5):1231-40. DOI: 10.1021/bi00379a005. View

14.

Morrow M, Taneva S, Simatos G, Allwood L, Keough K . 2H NMR studies of the effect of pulmonary surfactant SP-C on the 1,2-dipalmitoyl-sn-glycero-3-phosphocholine headgroup: a model for transbilayer peptides in surfactant and biological membranes. Biochemistry. 1993; 32(42):11338-44. DOI: 10.1021/bi00093a010. View

15.

Barry J, Gawrisch K . Direct NMR evidence for ethanol binding to the lipid-water interface of phospholipid bilayers. Biochemistry. 1994; 33(26):8082-8. DOI: 10.1021/bi00192a013. View

16.

Charp P, Zhou Q, Wood Jr M, Raynor R, Menger F, Kuo J . Synthetic branched-chain analogues of distearoylphosphatidylcholine: structure-activity relationship in inhibiting and activating protein kinase C. Biochemistry. 1988; 27(13):4607-12. DOI: 10.1021/bi00413a004. View

17.

Bonser R, Thompson N, HODSON H, Beams R, Garland L . Evidence that a second stereochemical centre in diacylglycerols defines interaction at the recognition site on protein kinase C. FEBS Lett. 1988; 234(2):341-4. DOI: 10.1016/0014-5793(88)80112-1. View

18.

Konstant P, Pearce L, Harvey S . Langevin dynamics of the choline head group in a membrane environment. Biophys J. 1994; 67(2):713-9. PMC: 1225414. DOI: 10.1016/S0006-3495(94)80532-6. View

19.

Wilschut J, Regts J, Westenberg H, Scherphof G . Action of phospholipases A2 on phosphatidylcholine bilayers. Effects of the phase transition, bilayer curvature and structural defects. Biochim Biophys Acta. 1978; 508(2):185-96. DOI: 10.1016/0005-2736(78)90324-3. View

20.

Zidovetzki R, Lester D . The mechanism of activation of protein kinase C: a biophysical perspective. Biochim Biophys Acta. 1992; 1134(3):261-72. DOI: 10.1016/0167-4889(92)90185-e. View