Photophysical properties and localization of chlorins substituted with methoxy groups, hydroxyl groups and alkyl chains in liposome-like cellular membrane

Biomedical Materials

Volumn 2, Issue 2, 2007, Pages 107-115

  Al Omari, S ^a  

^a HASHEMITE UNIVERSITY   (Jordan)

Author keywords

[No Author keywords available]

Indexed keywords

2,3 DIHYDRO 2,3 DIHYDROXY 5,10,15,20 TETRAKIS(3 HYDROXYPHENYL)PORPHYRIN; 2,3 DIHYDRO 2,3 DIHYDROXY 5,10,15,20 TETRAKIS(3 METHOXYPHENYL)PORPHYRIN; 2,3 DIHYDRO 2,3 DIHYDROXY 5,10,15,20 TETRAPHENYLPORPHYRIN; 5 HEXYL 12,13 DIHYDRO 12,13 DIHYDROXY 10,15,20 TRIS(3 METHOXYPHENYL)PORPHYRIN; 5 HEXYL 2,3 DIHYDRO 2,3 DIHYDROXY 10,15,20 TRIS(3 METHOXYPHENYL)PORPHYRIN; ALKYL GROUP; HYDROXYL GROUP; LIPOSOME; PORPHYRIN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CELL MEMBRANE; CONTROLLED STUDY; FLUORESCENCE SPECTROSCOPY; HUMAN; HUMAN CELL; LEUKEMIA CELL LINE; LIGHT; PHOTODYNAMIC THERAPY; PHOTOSENSITIZATION; TEMPERATURE DEPENDENCE;

ALKYLATION; BIOMIMETIC MATERIALS; CELL MEMBRANE; HUMANS; HYDROXYL RADICAL; JURKAT CELLS; LIGHT; LIPID BILAYERS; LIPOSOMES; MATERIALS TESTING; PHOSPHOLIPIDS; PHOTOCHEMISTRY; PORPHYRINS;

EID: 34249102274     PISSN: 17486041     EISSN: 1748605X     Source Type: Journal    
DOI: 10.1088/1748-6041/2/2/008     Document Type: Article

References (46)

1. Bonnett R 1995 Photosensitizers of the porphyrin and phthalocyanine series for photodynamic theory Chem. Soc. Rev. 24 19-33
2. Fong D S 2000 Photodynamic therapy with verteporfin for age-related macular degeneration Ophthalmology 107 2314-7
3. Ali H and VanLier J E 1999 Metal complexes as photo- and radiosensitizers Chem. Rev. 99 2397-450
4. Murfee H J, Thoms T P, Greaves J and Hong B 2000 New metallodendrimers containing an octakis(diphenylphosphino)-functionalized silsesquioxane core and ruthenium(II)-based chromophores Inorg. Chem. 39 5209-17
5. Robert J C, Adams Y E, Tomalia D, Mercer-Smith J A and LavaLlee D 1990 Using starburst dendrimers as linker molecules to radiolabel antibodies Bioconjug. Chem. 1 305-8
6. MacDonald I and Dougherty T 2001 Basic principles of photodynamic therapy Porphyrins Phthalocyanines 5 105-29
7. Bonnett R, Charlesworth P, Djelal B D, Foley S, McGarvey D J and Truscott T G 1999 Photophyscial properties of 5,10,15,20-tetrakis(m-hydroxyphenyl) porphyrin (m-HPP), 5,10,15,20-tetrakis(m-hydoxyphenyl) chlorin (m-THPC) and 5,10,15,20-tetrakis(m-hydroxyphenyl) bacteriochlorin (m-THPBC): a comparative study J. Chem. Soc. Perkin Trans. 2 325-34
8. Boyle R W and Dolphin D 1996 Structure and biodistribution relationships of photodynamic sensitizers Photochem. Photobiol. 64 469-85
9. Matroule J, Bonizzi G, Morliere P, Paillous N, Santus R, Bours V and Piette J 1999 Pyropheophorbide-a methyl ester-mediated photosensitization activates transcription factor NF-kB through the interleukin-1 receptor-dependent signaling pathway J. Biol. Chem. 274 2988-3000
10. Macalpine J, Boch R and Dolphin D J 2002 Evaluation of tetraphenyl-2,3-dihydroxychlorins as potential photosensitizers Porphyrins Phthalocyanines 6 146-55
11. Riis H, Altermatt H, Inderbitzi R, Hess R, Nachbur B, Stewart J, Wang Q, Lim C, Bonnett R, Berenbaum M and Althaus U 1991 Photodynamic therapy with chlorins for diffuse malignant mesothelioma: initial clinical results Br. J. Cancer 64 1116-20
12. Berenbaum M C, Akande S L, Bonnet R, Kaur H, Ioannou S, White R D and Winfield U J 1986 Meso-tetra(hydroxyphenyl)-porphyrins, a new class of potent tumour photosensitizers with favourable selectivity Br. J. Cancer 54 717-25
13. Bonnett R and Berenbaum M 1989 In Photosensitizing Compounds: Their Chemistry, Biology and Clinical Use vol 146 ed Ciba Symposium Foundation (Chichester: Wiley) pp 40-59
14. Fischer H and Eckoldt H 1940 Liebigs Ann. Chem. 544 138-162
15. Chang C K and Sotiriou C 1985 J. Org. Chem. 50 4989-91
16. Bonnett R, Nizhnik A N and Berenbaum M C 1989 J. Chem. Soc. Chem. Commun. 14 1822-3
17. Inhoffen H H, Ulrich J, Hoffmann H A and Klinzmann G 1969 Tetrahedron Lett. 23 613-16
18. Woodburn K, Chang C K, Lee S, Henderson B and Kessel D 1994 Photochem. Photobiol. 60 154-9
19. Bonnett R, Nizhnik A N, White S G and Berenbaum M C 1990 Porphyrin sensitizers in tumour phototherapy. Novel sensitizers of the chlorin and bacteriochlorin class with amphiphilic properties J. Photochem. Photobiol. B 6 29-37
20. Adams K R, Berenbaum M C, Bonnett R, Nizhnik A N, Salgado A and Vallés M A 1992 Second generation tumour photosensitizers: the synthesis and biological activity of octaalkylchlorins and bacteriochlorins with graded amphiphilic character J. Chem. Soc. Perkin Trans. 1 1465-70
21. Pandey R K et al 1997 Synthesis, photophysical properties, in vivo photosensitizing efficacy, and human serum albumin (HSA) binding properties of some novel bacteriochlorins J. Med. Chem. 40 2770-9
22. Macalpine J, Boch R and Dolphin D 2002 Evaluation of tetraphenyl-2,3- dihydroxychlorins as potential photosensitizers J. Porphyrins Phthalocyanines 6 14-6
23. Rancan F, Wiehe A, Nöbel M, Senge M, Al-Omari S, Böhm F, John M and Röder B 2004 Influence of substitutions on asymmetric dihydroxychlorins with regard to intracellular uptake, subcellular localization and photosensitization of Jurkat cells Photochem. Photobiol. 78 17-28
24. Kongshaug M 1992 Distribution of tetrapyrrole photosensitizers among human plasma proteins Int. J. Biochem. 24 1239-65
25. Van Lier J E and Spikes J D 1989 Photosensitizing Compounds: Their Chemistry Biology Clinical Use vol 146 ed Ciba Symposium Foundation (Chichester: Wiley) pp 17-32
26. Redmond R W, Land E J and Truscott T G 1985 Advances in Experimental Medicine and Biology vol 193 (New York: Plenum) p 301
27. Wiehe A, Simonenko E J, Senge M O and Röder B 2001 Hydrophilicity vs hydrophobicity-varying the amphiphilic structure of porphyrins related to the photosensitizer m-THPC J. Porphyrins Phthalocyanines 5 758-61
28. Brückner C, Rettig S and Dolphin D 1998 Formation of a meso-tetraphenylsecochlorin and a homoporphyrin with a twist J. Org. Chem. 63 2094-98
29. Oelckers St, Sczepan M, Hanke Th and Röder B 1997 Time-resolved detection of singlet oxygen luminescence in red ghost cell suspensions J. Photochem. Photobiol. B: Biol. 39 219-23
30. Kremer J, Esker M, Pathmamanoharan C and Wiersema P 1977 Vesicles of variable diameter prepared by a modified injection method Biochemistry 16 3932-35
31. Korth O, Hanke Th, Rückmann I and Röder B 1995 High sensitive and spatially resolved absorption fluorescence measurements on ultrathin Langmuir-Blodgett-films Exp. Tech. Phys. 41 25-36
32. Spiller W, Kliesch H, Wöhrle D, Hackbarth St and Röder B 1998 Singlet oxygen quantum yields of different photosensitizers in polar solvents and micellar solutions J. Porphyrins Phthalocyanines 2 145-58
33. Reichardt C 1988 Solvents and Solvent Effects in Organic Chemistry 2nd edn (Weinheim: VCH)
34. Abraham M, Grellier P, Abboud J, Doherty R and Taft R 1988 Solvent effects in organic chemistry recent developments Can. J. Chem. 66 2673-86
35. Röder B, Hackbarth St, Korth O, Zimmermann C, Herter Hanke T and Höhne W 1996 Photophysical properties of pheophorbide a in different carrier-systems SPIE 2625 179-86
36. Redmond W, Valduga G, Nonell S, Braslavsky S, Schaffner K, Vogel E, Pramod K and Koecher M 1989 The photophysical properties of porphycene incorporated in small unilamellar lipid vesicles J. Photochem. Photobiol. B: Biol. 3 193-207
37. Röder B, Hanke Th, Oelckers St, Hackbarth St and Symietz C 2000 Photophysical properties of pheophorbide a in solution and in model membrane systems J. Porphyrins Phthalocyanines 4 37-44
38. Henderson B and Dougherty T 1992 How does photodynamic therapy work? Photochem. Photobiol. 55 145-57
39. Lenz B R, Barenholz Y and Thompson T E 1976 Fluorescence depolarization studies of phase transitions and fluidity in phospholipid bilayers single component phosphatidylcholine liposomes Biochemistry 15 4521-8
40. II'ichev YuV, Demyashkevich A B, Kuzmin M G and Lemmetyinen H 1993 J. Photochem. Photobiol. A: Chem. 74 155-9
41. Osuka A, Wada Y and Shinoda S 1996 Covalently linked pyropheophorbide dimers as models of the special pair in the photosynthetic reaction center Tetrahedron 52 4311-26
42. Lacowicz J 1999 Principles of Fluorescence Spectroscopy (Dordrecht/New York: Kluwer/Plenum) p 6
43. Hagan T, Pilloud D and Suppan P 1987 Chem. Phys. Lett. 139 499-502
44. Dolphin D 1978 The Porphyrins: Vol II. Structure and Synthesis: Part B vol 3 (New York: Academic) p 7
45. Margaron P, Gregorie M, Scasnor V, Ali H and Van Lier J E 1996 Structure-photodynamic activity relationships of a series of 4-substituted zinc phthalocyanines Photochem. Photobiol. 63 217-23
46. Gomer C and Smith D 1980 Photoinactivation of Chinese-Hamster cells by hematoporphyrin derivative and red light Photochem. Photobiol. 32 341-8