Interaction of photosensitizers with liposomes containing unsaturated lipid

Chemistry and Physics of Lipids

Volumn 145, Issue 2, 2007, Pages 63-71

  Voszka, István ^a   Budai, Marianna ^a   Szabó, Zsófia ^a   Maillard, Philip ^b   Csík, Gabriella ^a   Gróf, Pál ^a  

^a SEMMELWEIS UNIVERSITY   (Hungary)

^b INSTITUT CURIE   (France)

Author keywords

Differential scanning calorimetry; Electron paramagnetic resonance; Liposomes; Photosensitizer; Porphyrin; Spin labeling

Indexed keywords

12 DOXYLSTEARIC ACID; 16 DOXYLSTEARIC ACID; 5 DOXYLSTEARIC ACID; DIOLEOYLPHOSPHATIDYLCHOLINE; DIPALMITOYLPHOSPHATIDYLCHOLINE; LIPOSOME; NITROXIDE; OXYGEN; PHOTOSENSITIZING AGENT; RADICAL; SOLVENT; STEARIC ACID DERIVATIVE; TETRAPHENYLPORPHYRIN DERIVATIVE; UNCLASSIFIED DRUG; UNSATURATED FATTY ACID;

ARTICLE; CHEMICAL BOND; DIFFERENTIAL SCANNING CALORIMETRY; DOSE RESPONSE; ELECTRON SPIN RESONANCE; GLYCOSYLATION; LIGHT; LIPID ANALYSIS; LIPID BILAYER; LIPID MEMBRANE; MEMBRANE STRUCTURE; OXYGEN SATURATION; PHOTOREACTIVITY; PRIORITY JOURNAL; SIGNAL DETECTION; SPIN LABELING;

1,2-DIPALMITOYLPHOSPHATIDYLCHOLINE; CALORIMETRY, DIFFERENTIAL SCANNING; CYCLIC N-OXIDES; ELECTRON SPIN RESONANCE SPECTROSCOPY; GALACTOSIDES; GLUCOSIDES; LIGHT; LIPID BILAYERS; LIPOSOMES; MEMBRANE FLUIDITY; PHOSPHATIDYLCHOLINES; PHOTOSENSITIZING AGENTS; PORPHYRINS; SPIN LABELS;

EID: 33846168714     PISSN: 00093084     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chemphyslip.2006.10.005     Document Type: Article

References (51)

1. Agrez M.V., Wharen R.E., Anderson R.E., Laws E.R., Ilstrup D.M., Cortese D.A., Shorter R.G., and Lieber M.M. Haematoporphyrin derivative: quantitative uptake in dimethylhydrazine-induced murine colorectal carcinoma. J. Surg. Oncol. 24 (1983) 173-176
2. Biltonen R.L., and Lichtenberg G.D. The use of differential scanning calorimetry as a tool to characterize liposome preparations. Chem. Phys. Lipids 64 (1993) 129-142
3. Cimato A.N., Piehl L.L., Facorro G.B., Tortl H.B., and Hager A.A. Antioxidant effects of water- and lipid-soluble nitroxide radicals in liposomes. Free Rad. Biol. Med. 37 (2004) 2042-2051
4. Csík G., Balog E., Voszka I., Tölgyesi F., Oulmi D., Maillard P., and Momenteau M. Glycosilated derivatives of tetraphenyl porphyrin: photophysical characterisation, self-aggregation and membrane binding. J. Photochem. Photobiol. B: Biol. 44 (1998) 216-224
5. Damoiseau X., Schuitmaker H.J., Lagerberg J.W.M., and Hoebeke M. Increase of the photosensitizing efficiency of the bacteriochlorin a by liposome-incorporation. J. Photochem. Photobiol. B: Biol. 60 (2001) 50-60
6. Diamond I., Granelli S.G., McDonagh A.F., Nielsen S., Wilson C.B., and Jaenicke R. Photodynamic therapy of malignant tumours. Lancet 2 (1972) 1175-1177
7. Dougherty T.J. Activated dyes as anti-tumor agents. Natl. Cancer Inst. 51 (1974) 1333-1336
8. Dougherty T.J., Gomer C.J., Henderson B.W., Jori G., Kessel D., Korbelik M., Moan J., and Peng Q. Photodynamic therapy. J. Natl. Cancer Inst. 90 (1998) 889-905
9. Fong D.S. Photodynamic therapy with verteporfin for age-related macular degeneration. Ophthalmology 107 (2000) 2314-2317
10. Gaspard S., Tempete C., and Werner G.H. Studies on photoinactivation by various phthalocyanines of a free or replicating non-enveloped virus. J. Photochem. Photobiol. B: Biol. 31 (1995) 159-162
11. 2-({radical dot}-) and OH by irradiation of the photosensitizer zinc(II) phthalocyanine. J. Photochem. Photobiol. B: Biol. 38 (1997) 196-202
12. Hill J.S., Kaye A.H., Sawyer W.H., Morstyn G., Medison P.D., and Stylli S.S. Selective uptake of haematoporphyrin derivative into human cerebral glioma. Neurosurgery 26 (1990) 244-248
13. Husain D., Miller J.W., Michaud N., Connolly E., Flotte T.J., and Gragoudas E.S. Intravenous infusion of liposomal benzoporphyrin derivative for photodynamic therapy of experimental choroidal neovascularization. Arch. Ophthalmol. 114 (1996) 978-985
14. Kessel D. Porphyrin-lipoprotein association as a factor in porphyrin localization. Cancer Lett. 33 (1986) 183-188
15. Kessel D. Photodynamic therapy and neoplastic disease. Oncol. Res. 4 (1992) 219-225
16. Kessel D., Woodburn K., Henderson B.W., and Chang C.K. Sites of photodamage in vivo and in vitro by cationic porphyrin. Photochem. Photobiol. 62 (1995) 875-881
17. Killig F., and Stark G. Photodynamic activation of ion transport through lipid membranes and its correlation with an increased dielectric constant of the membrane. Biochim. Biophys. Acta 1564 (2002) 207-213
18. Konan Y.N., Chevallier J., Gurny R., and Allemann E. Encapsulation of p-THPP into nanoparticles: cellular uptake, subcellular localization and effect of serum on photodynamic activity. Photochem. Photobiol. 77 (2003) 638-644
19. Kostecka-Gugala A., Latowski G., and Strzalka K. Thermotropic phase behaviour of alpha dipalmitoylphosphatidylcholine multibilayers is influenced to various extent by carotenoids containing different structural features-evidence from differential scanning calorimetry. BBA-Biomembranes 1609 (2003) 193-202
20. Kunz L., and Stark G. Photodynamic membrane damage at the level of single ion channels. Biochim. Biophys. Acta 1327 (1997) 1-4
21. Ladd B.S., Solomon S.D., Bressler N.M., and Bressler S.B. Photodynamic therapy with verteporfin for choroidal neovascularization in patients with diabetic retinopathy. Am. J. Ophthalmol. 132 (2001) 659-667
22. Laville I., Figueiredo T., Loock B., Pigaglio S., Maillard Ph., Grierson D.S., Carrez D., and Croisy A.B.J. Synthesis, cellular internalization and photodynamic activity of glucoconjugated derivatives of tri and tetra(meta-hydroxyphenyl)chlorins. Bioorg. Med. Chem. 11 (2003) 1643-1652
23. Leman J.A., and Morton C.A. Photodynamic therapy: applications in dermatology. Expert Opin. Biol. Ther. 2 (2002) 45-53
24. Lui H., and Anderson R.R. Photodynamic therapy in dermatology: recent developments. Dermatol. Ther. 11 (1993) 1-13
25. MacDonald L.J., and Dougherty T.J. Basic principles of photodynamic therapy. J. Porphyr. Phthalocyanines 5 (2001) 105-129
26. Maillard Ph., Guerquin-Kern J.-L., Huel Ch., and Momenteau M. Glycoconjugated porphyrins. Part 2. Synthesis of sterically constrained polyglycosylated compounds derived from tetraphenylporphyrins. J. Org. Chem. 58 (1993) 2774-2780
27. Marsh D. Electron spin resonance: spin labels. In: Grell E. (Ed). Molecular Biology Biochemistry and Biophysics Membrane Spectroscopy, vol. 31 (1981), Springer, Berlin 51-142
28. Moan J. On the diffusion length of singlet oxygen in cells and tissues. J. Photochem. Photobiol. B: Biol. 6 (1990) 343-344
29. Moan J., Petterson E.O., and Christensen T. The mechanism of photodynamic inactivation of human cells in vitro in the presence of hematoporphyrin. Br. J. Cancer 39 (1979) 398-402
30. Moore J.V., West C.M.L., and Whitehurst C. The biology of photodynamic therapy. Phys. Med. Biol. 42 (1997) 913-935
31. Moser J.G., Montforts F.P., Kusch D., Vervoorts A., Kirsch D., Berghahn M., Akguen N., Rueck A.C., Andrees S., and Wagner B. How many molecules of a photosensitizer are necessary to photosensitize a tumor cell?. Proceedings of SPIE-The International Society for Optical Engineering 2924 (1996) 22-30
32. Nyamekye I. Vascular and other non-tumour applications of photodynamic therapy. Lasers Med. Sci. 11 (1996) 3-10
33. Oulmi D., Maillard Ph., Guerquin-Kern J.-L., Huel Ch., and Momenteau M. Glycoconjugated porphyrins. Part 3. Synthesis of flat amphiphilic mixed meso-(glycosylated aryl)arylporphyrins and mixed meso-(glycosylated aryl)alkylporphyrins bearing some monosaccharide and disaccharide groups. J. Org. Chem. 60 (1995) 1554-1564
34. Peeler J.P., and Valenzeno D. The role of singlet oxygen in photooxidation of excitable cell membranes. Photochem. Photobiol. 30 (1979) 581-586
35. Penning L.C., and Dubbelman T.M.A.R. Fundamentals of photodynamic therapy: cellular and biochemical aspects. Anti-Cancer Drugs 5 (1994) 139-146
36. Ricchelli F. Photophysical properties of porphyrins in biological membranes. J. Photochem. Photobiol. B: Biol. 29 (1995) 109-118
37. Saija A., Bonina F., Trombetta D., Tomaino A., Montenegro L., Smeriglio P., and Castelli F. Flavonoid-biomembrane interactions-a calorimetric study on dipalmitoylphosphatidylcholine vesicles. Int. J. Pharm. 124 (1995) 1-8
38. Santus R., and Reyftmann J.F. Photosensitization of membrane components. Biochimie 68 (1986) 843-848
39. Schroder T., Chen I.-W., Sperling M., Bell R.H., Brackett K., and Joffe S.N. Haematoporphyrin derivative uptake and photodynamic therapy in pancreatic carcinoma. J. Surg. Oncol. 38 (1988) 4-9
40. Sparrow J.R., Zhou J., and Cai B. DNA is a target of the photodynamic effects elicited in A2E-laden RPE by blue-light illumination. Invest. Ophthalmol. Visual Sci. 4 (2003) 2245-2251
41. Teiten M.H., Marchal S., D'Hallewin M.A., Guillemin F., and Bezdetnaya L. Primary photodamage sites and mitochondrial events after Foscan photosensitization of MCF-7 human breast cancer cells. Photochem. Photobiol. 78 (2003) 9-14
42. + leakage and damage to band 3 in photodynamically treated red cells. Photochem. Photobiol. 75 (2002) 167-171
43. Uzdensky A.B., Dergacheva O.Y., Zhavoronkova A.A., Reshetnikov A.V., and Ponomarev G.V. Photodynamic effect of novel chlorin e6 derivatives on a single nerve cell. Life Sci. 74 (2004) 2185-2197
44. Voszka I., Galántai R., Maillard Ph., and Csík G. Interaction of glycosylated tetraphenyl porphyrins with model lipid membranes of different composition. J. Photochem. Photobiol B: Biol. 52 (1999) 92-98
45. Voszka I., Szabó Zs., Csík G., Maillard Ph., and Gróf P. Interaction of tetraphenyl porphyrin derivatives with DPPC-liposomes: an EPR study. J. Photochem. Photobiol. B: Biol. 79 (2005) 83-88
46. Wainwright M. Photodynamic antimicrobial chemotherapy (PACT). J. Antimicrob. Chemother. 42 (1998) 13-28
47. Weishaupt K.R., Gomer C.J., and Dougherty T.J. Identification of singlet oxygen as the cytotoxic agent in photo-inactivation of a murine tumor. Cancer Res. 36 (1976) 2326-2329
48. Wiehe A., Simonenko E.J., Senge M., and Roder B. Hydrophilicity vs. hydrophobicity-varying the amphiphilic structure of porphyrins related to the photosensitizer m-THPC. J. Porphyrins Phthalocyanines 5 (2001) 758-761
49. Yang H.Y., Li M.F., Zhang W.G., Zhao H.X., and Zhang Z.Y. Characteristics of photosensitization of Pheophorbide a in liposomal media. Sci. China C-Life Sci. 42 (1999) 471-480
50. Yu C., Xu S., Chen S., Zhang M., and Shen T. Investigation of photobleaching of hypocrellin B in non-polar organic solvent and in liposome suspension. J. Photochem. Photobiol. B: Biol. 68 (2002) 73-78
51. Zheng G., Graham A., Shibata M., Missert J.R., Oseroff A.R., Dougherty T.J., and Pandey R.K. Synthesis of B-galactose-conjugated chlorins derived by enyne metathesis as galectin-specific photosensitizers for photodynamic therapy. J. Org. Chem. 66 (2001) 8709-8716