The effect of 3-pentadecylphenol on DPPC bilayers ATR-IR and 31P NMR studies

Biophysical Chemistry

Volumn 140, Issue 1-3, 2009, Pages 51-56

  Cieślik Boczula, Katarzyna ^a   Koll, Aleksander ^a  

^a UNIVERSITY OF WROC AW   (Poland)

Author keywords

31P NMR; ATR IR; DPPC; Liposome; Phase transition; Phenolic lipid

Indexed keywords

DECYLBENZOIC ACID DERIVATIVE; DIPALMITOYLPHOSPHATIDYLCHOLINE; PHENOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CONTROLLED STUDY; DISPERSION; HYDROPHILICITY; HYDROPHOBICITY; INFRARED SPECTROSCOPY; LIPID BILAYER; PHASE TRANSITION; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PHYSICAL CHEMISTRY; PRIORITY JOURNAL;

1,2-DIPALMITOYLPHOSPHATIDYLCHOLINE; HYDROPHOBICITY; LIPID BILAYERS; LIPOSOMES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PHASE TRANSITION; PHENOLS; PHOSPHORUS ISOTOPES; SPECTROPHOTOMETRY, INFRARED; SURFACE PROPERTIES; WATER;

EID: 58549086525     PISSN: 03014622     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bpc.2008.11.009     Document Type: Article

References (28)

1. Kozubek A., and Tyman J.H.P. Cereal grain resorcinolic lipids: mono and dienoic homologues are present in rye grains. Chem. Phys. Lipids 78 (1995) 29-35
2. Kozubek A., and Tyman J.H.P. Resorcinolic lipids, the natural nonisoprenoid phenolic amphiphiles and their biological activity. Chem. Rev. 99 (1999) 1-25
3. Wenkkert E., Loeser E., Mahapatra S.N., Schenker F., and Wilson E.M.J. Wheat bran phenols. J. Org. Chem. 29 (1964) 435-439
4. Reusch P.N., and Sadoff H.L.J. 5-n-Alkylresorcinols from encysting Azotobacter vinelandii: isolation and characterization. J. Bacteriol. 139 (1979) 448-453
5. Bandypadhyay C., Gholap A., and Mamdapur V.J.R. Characterization of alkenylresorcinol in mango (Mangifera indica L.) latex. Agric. Food Chem. 33 (1985) 377-379
6. Itakowa H., Totsuka N., Nakahara K., Maezuru M., Takeya K., Kondo M., Inamatsu M., and Morita H. A quantitative structure-activity relationship for antitumor activity of long-chain phenols from Ginkgo biloba L. Chem. Pharm. Bull. 37 (1989) 1619-1621
7. Kozubek A., Nietubyc M., and Sikorski A.F. Modulation of the activities of membrane enzymes by cereal grain resorcinolic lipids. Z. Naturforsch. 47c (1992) 41-46
8. Kubo I., Komatsu K., and Ochi M. Molluscicides from the cashew Anacardium occidentale and their large-scale isolation. J. Agric. Food Chem. 34 (1986) 970-973
9. shell in organic media. J. Colloid Interface Sci. 312 (2007) 498-505
10. Kato T., Mizoshita N., and Kishimoto K. Functional liquid-crystalline assemblies: self-organized soft material. Angew. Chem. Int. Ed. 45 (2006) 38-68
11. T. Nakatsu and Z. Chen, United States Patent No. 07/685,285, 15.05.1991
12. Amorati R., Pedulli G.F., Valgimigli L., Attanasi O.A., Filippone P., Fiorucci Ch., and Saladino R. Absolute rate constants for the reaction of peroxyl radicals with cardanol derivatives. J. Chem. Soc., Perkin Trans. 2 (2001) 2142-2146
13. Ciesik K., Koll A., and Grdadolnik J. Structural characterization of a phenolic lipid and its derivative using vibrational spectroscopy. Vib. Spectrosc. 41 (2006) 14-20
14. Mantsch H.H., and Chapman D. Infrared Spectroscopy of Biomolecules (1996), Wiley-Liss, New York
15. Cullis P.R., and De Kruijff B. Lipid polymorphism and functional roles of lipids in biological membranes. Biochim. Biophys. Acta 559 (1979) 399-420
16. 31P NMR study. Biochim. Biophys. Acta 513 (1978) 31-42
17. M. Kodoma, M. Kuwabara and S. Seki, Successive phase-transition phenomena and phase diagram of the phosphatidylcholine-water system as revealed by differentia scanning calorimetry, 689 (1982) 567-570.
18. Cieślik-Boczula K., Czarnik-Matusewicz B., Perevozkina M., Filarowski A., Boens N., De Borggraeve W., and Koll A. ATR-IR spectroscopic study of the structural changes in the hydrophobic region of ICPAN/DPPC bilayers. J. Mol. Struct. 878 (2008) 162-168
19. Cameron D.G., Casal H.L., Gudgin E.F., and Mantsch H.H. The gel phase of dipalmitoyl phosphatidylcholine. An infrared characterization of the acyl chain packing. Biochim. Biophis. Acta 596 (1980) 463-467
20. Cameron D.G., Casal H.L., and Mantsch H.H. Characterization of the pretransition in 1,2-dipalmitoyl-sn-glycero-3-phosphocholine by Fourier transform infrared spectroscopy. Biochemistry 19 (1980) 3665-3672
21. Snyder R.G. Vibrational spectra of crystalline n-paraffins: II. Intermolecular effects. J. Mol. Spectrosc. 7 (1961) 116-144
22. Bush S.F., Levin H., and Levin I.W. Cholesterol-lipid interactions: an infrared and Raman spectroscopic study of the carbonyl stretching mode region of 1,2-dipalmitoyl phosphatidylcholine bilayers. Chem. Phys. Lipids 27 (1980) 101-111
23. Levin I.W., Mushayakarara E., and Bittman R. Vibrational assignment of the sn-1 and sn-2 chain carbonyl stretching modes of membrane phospholipids. J. Raman Spectrosc. 13 (1982) 231-234
24. Mushayakarara E., and Levin W.I. Determination of acyl chain conformation at the lipid interface region: Raman spectroscopic study of the carbonyl stretching mode region of dipalmitoyl phosphatidylcholine and structurally related molecules. J. Phys. Chem. 86 (1982) 2324-2327
25. Casal H.L., and Mantsch H.H. Polymorphic phase behaviour of phospholipid membranes studied by infrared spectroscopy. Biochim. Biophys. Acta 779 (1984) 381-401
26. Arronda J.L.R., and Macarulla F.M. Infrared spectroscopy of phosphatidylcholines in aqueous suspension a study of the phosphate group vibrations. Biochim. Biophys. Acta 794 (1984) 165-168
27. Cieślik-Boczula K., and Koll A. Characterisation of the structure of PDP-DPPC bilayers by DFT and PM3 calculations. Pol. J. Chem. 81 (2007) 1081-1093
28. Kozubek A., and Demel R.A. The effect of 5(-n-alk(en)yl) resorcinols from rye on membrane structure. Biochim. Biophys Acta 642 (1981) 242-251