Anticancer cisplatin interactions with bilayers of total lipid extract from pig brain: A 13C, 31P and 15N solid-state NMR study

European Journal of Pharmaceutical Sciences

Volumn 34, Issue 2-3, 2008, Pages 140-148

  Jensen, Magnus ^a   Nerdal, Willy ^a  

^a UNIVERSITY OF BERGEN   (Norway)

Author keywords

13C MAS NMR; 15N MAS NMR; 31P MAS NMR; Bilayers; Cisplatin bilayer interaction

Indexed keywords

BRAIN EXTRACT; CISPLATIN; LIPID;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DNA ADDUCT; DRUG SYNTHESIS; LIPID BILAYER; NEUROTOXICITY; NITROGEN NUCLEAR MAGNETIC RESONANCE; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; SWINE;

ANIMALS; ANTINEOPLASTIC AGENTS; BRAIN CHEMISTRY; CISPLATIN; DRUG CARRIERS; LIPID BILAYERS; LIPOSOMES; MAGNETIC RESONANCE SPECTROSCOPY; PHOSPHATIDYLSERINES; SWINE;

EID: 44349162787     PISSN: 09280987     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ejps.2008.03.002     Document Type: Article

References (57)

1. Adebodun F., Chung J., Montez B., Oldfield E., and Shan X. Spectroscopic studies of lipids and biological membranes: carbon-13 and proton magic-angle sample-spinning nuclear magnetic resonance study of glycolipid-water systems. Biochemistry 31 (1992) 4502-4509
2. Afri M., Ehrenberg B., Talmon Y., Schmidt J., Cohen Y., and Frimer A.A. Active oxygen chemistry within the liposomal bilayer. Part III. Locating Vitamin E, ubiquinol and ubiquinone and their derivatives in the lipid bilayer. Chem. Phys. Lipids 131 (2004) 107-121
3. Akaboshi M., Kowai K., Maki H., Akuta K., Ujeno Y., and Miyahara T. The number of platinum atoms binding to DNA, RNA, and protein molecules of HeLa cells treated with cisplatin at its mean lethal concentration. Jpn. J. Cancer Res. 83 (1992) 522-526
4. 3)(cyclohexylamine)]. Inorg. Chim. Acta 273 (1998) 8-13
5. 15N] NMR spectroscopy. J. Chem. Soc., Chem. Commun. (1992) 789-791
6. Berners-Price S.J., and Sadler P.J. Coordination chemistry of metallodrugs: insights into biological speciation from NMR spectroscopy. Coord. Chem. Rev. 151 (1996) 1-40
7. Binks S.P., and Dobrota M. Kinetics and mechanism of uptake of platinum-based pharmaceuticals by the rat small intestine. Biochem. Pharmacol. 40 (1990) 1329-1336
8. Bosl G.J., Bajorin D.F., and Sheinfeld J. In: DeVita V.T.J., Hellman S., and Rosenberg S.A. (Eds). Cancer of the Testis (2001), Lippincott, Williams and Wilkins, Philadelphia
9. Brabec V., and Kasparkova J. Molecular aspects of resistance to antitumor platinum drugs. Drug Resist. Updates 5 (2002) 147-161
10. Burger N.J., Staffhorst R.W.H.M., and de Kruijff B. Interaction of the anti-cancer drug cisplatin with phosphatidylserine in intact and semi-intact cells. Biochim. Biophys. Acta 1419 (1999) 43-54
11. Chicano J.J., Ortiz A., Teruel J.A., and Aranda F.J. Organotin compounds promote the formation of non-lamellar phases in phosphatidylethanolamine membranes. Biochim. Biophys. Acta 1558 (2002) 70-81
12. Chupin V., de Kroon A.I.P.M., and de Kruijff B. Molecular architecture of nanocapsules, bilayer-enclosed solid particles of cisplatin. J. Am. Chem. Soc. 126 (2004) 13816-13821
13. 31P NMR. Evidence that cholesterol may destabilize bilayer structure in membrane systems containing phosphatidylethanolamine. Biochim. Biophys. Acta 507 (1978) 207-218
14. 31P NMR study. Biochim. Biophys. Acta 513 (1978) 31-42
15. Cullis P.R., and Hope M.J. The bilayer stabilizing role of sphingomyelin in the presence of cholesterol. Biochim. Biophys. Acta 597 (1980) 533-542
16. Devaux P.F., and Seigneuret M. Specificity of lipid-protein interaction as determined by spectroscopic techniques. Biochem. Biophys. Acta 822 (1985) 63-125
17. Eastman A. Reevaluation of interaction of cis-dichloro(ethylenediammine)platinum(II) with DNA. Biochemistry 25 (1986) 3912-3915
18. Epand R.M., and Epand R.F. Non-raft forming sphingomyelin-cholesterol mixtures. Chem. Phys. Lipids 132 (2004) 37-46
19. 13C NMR of multilamellar dispersions of polyunsaturated (22:6) phospholipids. Biophys. J. 79 (2000) 885-897
20. Fichtinger-Schepman A.M., van Dosterom A.T., Lohman P.H., and Berends F. cis-Diamminedichloroplatinum(II)-enhanced DNA adducts in peripheral leukocytes from seven cancer patients: quantitative immunochemical detection of the adduct induction and removal after a single dose of cis-diamminedichloroplatinum(II). Cancer Res. 47 (1987) 3000-3004
21. Gately D.P., and Howell S.B. Cellular accumulation of the anticancer agent cisplatin: a review. Br. J. Cancer 67 (1993) 1171-1176
22. 199Hg NMR. Biochim. Biophys. Acta 1325 (1997) 250-262
23. Guo W., and Hamilton J.A. A multinuclear solid-state NMR study of phospholipid-cholesterol interactions. Dipalmitoylphosphatidylcholine-cholesteol binary system. Biochemistry 34 (1995) 14174-14184
24. Henkels K.M., and Turchi J.J. Induction of apoptosis in cisplatin-sensitive and -resistant human ovarian cancer cell lines. Cancer Res. 57 (1997) 4488-4492
25. Holwerda D.L., Ellis P.D., and Wuthier R.E. Carbon-13 and Phosphorus-31 nuclear magnetic resonance studies on interaction of calcium with phosphatidylserine. Biochemistry 20 (1981) 418-428
26. Hwang F., Zhao D.-Q., Chen J.-W., Chen X.-H., and Ni J.-Z. Effect of lanthanum ions on the lipid polymorphism of phosphatidylethanolamines. Chem. Phys. Lipids 82 (1996) 73-77
27. Jamieson E.R., and Lippard S.J. Structure, recognition, and processing of cisplatin-DNA adducts. Chem. Rev. 99 (1999) 2467-2498
28. Janiak M.J., Small D.M., and Shipley G.G. Temperature and compositional dependence of the structure of hydrated dimyristoyl lecithin. J. Biol. Chem. 254 (1979) 6068-6078
29. Kartalou M., and Essigman J.M. Mechanisms of resistance to cisplatin. Mut. Res. 478 (2001) 23-43
30. Keusgen M., Yu C.-M., Curtis J.M., Brewer D., and Ayer S.W. A cerebroside from the marine fungus Microsphaeropsis olivacea (Bonord.) Höhn. Biochem. Syst. Ecol. 24 (1996) 65-468
31. Keys H.M., Bundy B.N., Stehman F.B., Muderspach L.I., Chafe W.E., Suggs C.L., Walker J.L., and Gersell D. Cisplatin, radiation, and adjuvant hysterectomy compared with radiation and adjuvant hysterectomy for bulky stage IB cervical carcinoma. N. Engl. J. Med. 340 (1999) 1154-1161
32. 15N-NMR spectroscopic examination of the transformation of organic nitrogen in plant biomass during thermal treatment. Soil Biol. Biochem. 28 (1996) 1053-1060
33. Lau T.-L., Ambroggio E.E., Tew D.J., Cappai R., Masters C.L., Fidelio G.D., Barnham K.J., and Separovic F. Amyloid-β peptide disruption of lipid membranes and the effect of metal ions. J. Mol. Biol. 356 (2006) 759-770
34. Levitt M. Symmetrical composite pulse sequences for NMR population inversion. I. Compensation of radiofrequency field inhomogeneity. J. Magn. Reson. 48 (1982) 234-264
35. Liang X., and Huang Y. Physical state changes of membrane lipids in human lung adenocarcinoma A549 cells and their resistance to cisplatin. Int. J. Biochem. Cell Biol. 34 (2002) 1248-1255
36. Liang X.-J., Mukherjee S., Shen D.-W., Maxfield F.R., and Gottesman M.M. Endocytic recycling compartments altered in cisplatin-resistant cancer cells. Cancer Res. 66 (2006) 2346-2353
37. 31P angular dependent nuclear spin relaxation time study. Biophys. J. 56 (1989) 543-549
38. Morris M., Eifel P.J., Lu J., Grigsby P.W., Levenback C., Stevens R.E., Rotman M., Gershenson D.M., and Mutch D.G. Pelvic radiation with concurrent chemotherapy compared with pelvic and para-aortic radiation for high-risk cervical cancer. N. Engl. J. Med. 340 (1999) 1137-1143
39. 13C NMR and differential scanning calorimetry. Biochim. Biophys. Acta 1464 (2000) 165-175
40. Perez R.P. Determinants of cisplatin resistance. Eur. J. Cancer 34 (1998) 1535-1542
41. Pinheiro T.J.T., and Watts A. Resolution of individual lipids in mixed phospholipid membranes and specific lipid-cytochrome c interactions by magic-angle spinning solid-state phosphorus-31 NMR. Biochemistry 33 (1994) 2459-2467
42. 13C-NMR spectroscopic studies as a new tool to screen fatty acids, sterol and cartenoids. J. Appl. Phycol. 4 (1992) 315-322
43. Ramstedt B., and Slotte J.P. Interaction of cholesterol with sphingomyelins and acyl-chain-matched phosphatidylcholines: a comparative study of the effect of the chain length. Biophys. J. 76 (1999) 908-915
44. Rose P.G., Bundy B.N., Watkins E.B., Thigpen J.T., Deppe G., Maimann M.A., Clarke-Pearson D.L., and Insalaco S. Concurrent cisplatin-based radiotherapy and chemotherapy for locally advanced cervical cancer. N. Engl. J. Med. 340 (1999) 1144-1153
45. Seddon J.M. Structure of the inverted hexagonal (HII) phase, and non-lamellar phase transitions of lipids. Biochem. Biophys. Acta 1031 (1990) 1-69
46. 31P nuclear magnetic resonance and the head group structure of phospholipids in membranes. Biochem. Biophys. Acta 515 (1978) 105-140
47. 31P NMR. Biochem. Biophys. Res. Commun. 286 (2001) 758-763
48. Singh M.M., Szafran Z., and Pike R.M. Microscale synthesis of cis-diamminedihaloplatinum(II) and a corresponding trans isomer. A rapid and convenient method of preparing cisplatin-an anticancer drug. J. Chem. Educ. 67 (1990) A261-A262
49. Small D.M. Observations on lecithin. Phase equilibria and structure of dry and hydrated egg lecithin. J. Lipid Res. 8 (1967) 551-557
50. 31P solid-state NMR study. Biophys. Chem. 120 (2006) 178-187
51. 31P solid-state NMR study. Biophys. Chem. 134 (2008) 47-55
52. Speelmans G., Staffhorst R.W.H.M., Versluis K., Reedijk J., and de Kruijff B. Cisplatin complexes with phosphatidylserine in membranes. Biochemistry 36 (1997) 10545-10550
53. van Duyl B.Y., Ganchev D., Chupin V., de Kruijff B., and Killian J.A. Sphingomyelin is much more effective than saturated phosphatidylcholine in excluding unsaturated phosphatidylcholine from domains formed with cholesterol. FEBS Lett. 547 (2003) 101-106
54. Wang D., and Lippard S.J. Cellular processing of platinum anticancer drugs. Nat. Rev. 4 (2005) 307-320
55. 31P-NMR and titration calorimetry study. Biochem. Biophys. Acta 1372 (1998) 227-236
56. Yeagle P.L., Hutton W.C., Huang C., and Martin R.B. Phospholipid head-group conformations; intermolecular interactions and cholesterol effects. Biochemistry 16 (1977) 4344-4349
57. Yeagle P.L., Hutton W.C., and Martin R.B. Sphingomyelin multiple phase behaviour as revealed by multinuclear magnetic resonance spectroscopy. Biochemistry 17 (1978) 5745-5750