Glycodendrimeric phenylporphyrins as new candidates for retinoblastoma PDT: Blood carriers and photodynamic activity in cells

Journal of Photochemistry and Photobiology B: Biology

Volumn 115, Issue , 2012, Pages 16-24

  Wang, Ze Jian ^a   Chauvin, Benoît ^a   Maillard, Philippe ^b,c   Hammerer, Fabien ^b,c   Carez, Danile ^b,d   Croisy, Alain ^b,d   Sandré, Catherine ^e   Chollet Martin, Sylvie ^e   Prognon, Patrice ^a   Paul, Jean Louis ^f,g   Blais, Jocelyne ^a   Kasselouri, Athena ^a  

^a University Paris Saclay   (France)

^b INSTITUT CURIE   (France)

^c CNRS   (France)

^d Centre Universitaire   (France)

^e Universite Paris Sud   (France)

^f HÔPITAL EUROPÉEN GEORGES POMPIDOU   (France)

^g EA 4529   (France)

Author keywords

Glycodendrimeric porphyrins; Photocytotoxicity; Photodynamic therapy (PDT); Plasma proteins; Retinoblastoma cells

Indexed keywords

GLYCODENDRIMERIC PHENYLPORPHYRIN DERIVATIVE; PLASMA PROTEIN; PORPHYRIN DERIVATIVE; TETRAPHENYLPORPHYRIN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG ACTIVITY; DRUG STRUCTURE; HUMAN; HUMAN CELL; PHOTODYNAMIC THERAPY; PHOTOTOXICITY; PRIORITY JOURNAL; RETINOBLASTOMA;

BIOLOGICAL TRANSPORT; BLOOD PROTEINS; CELL LINE, TUMOR; DENDRIMERS; ETHYLENE GLYCOL; ETHYLENE GLYCOLS; HUMANS; MANNOSE; PHOTOCHEMOTHERAPY; PHOTOSENSITIZING AGENTS; PORPHYRINS; RETINOBLASTOMA;

EID: 84865452061     PISSN: 10111344     EISSN: 18732682     Source Type: Journal    
DOI: 10.1016/j.jphotobiol.2012.06.005     Document Type: Article

References (35)

1. F. Doz, H. Brisse, D. Stoppa-Lyonnet, X. Sastre, J.-M. Zucker, and L. Desjardins Retinoblastoma, Paediatric Oncology 2004 Arnold Press London
2. L. Lumbroso-Le Rouic, I. Aerts, C. Lévy-Gabriel, R. Dendale, X. Sastre, M. Esteve, B. Asselain, D. Bours, F. Doz, and L. Desjardins Conservative Treatments of Intraocular Retinoblastoma Ophthalmology 115 2008 1405 1410
3. A.L. Murphree, M. Cote, and C.J. Gomer The evolution of photodynamic therapy techniques in the treatment of intraocular tumours Photochem. Photobiol. 46 1987 919 923
4. A.E. O'Connor, W.M. Gallagher, and A.T. Byrne Porphyrin and nonporphyrin photosensitizers in oncology: preclinical and clinical advances in photodynamic therapy Photochem. Photobiol. 85 2009 1053 1074
5. I. Laville, S. Pigaglio, J.-C. Blais, F. Doz, B. Loock, Ph. Maillard, D.S. Grierson, and J. Blais Photodynamic efficiency of diethylene glycol-linked glycoconjugated porphyrins in human retinoblastoma cells J. Med. Chem. 49 2006 2558 2567
6. S. Griegel, M.F. Rajewsky, T. Ciesiolka, and H.J. Gabius Endogenous sugar receptor (lectin) profiles of human retinoblastoma and retinoblast cell lines analyzed by cytological markers, affinity chromatography and neoglycoprotein-targeted photolysis Anticancer Res. 9 1989 723 730 (Pubitemid 19194307)
7. M. Monsigny, R. Mayer, and A.-C. Roche Sugar-lectin interactions: sugar clusters, lectin multivalency and avidity Carboh. Lett. 4 2000 35 52
8. L.L. Kiessling, J.E. Gestwicki, and L.E. Strong Synthetic multivalent ligands in the exploration of cell surface interactions Curr. Opin. Chem. Biol. 4 2000 696 703
9. L.L. Kiessling, and N.L. Pohl Strength in numbers: non-natural polyvalent carbohydrate derivatives Chem. Biol. 3 1996 71 77
10. S. Ballut, A. Makky, B. Loock, J.-Ph. Michel, Ph. Maillard, and V. Rosilio New strategy for targeting of photosensitizers. Synthesis of glycodendrimeric phenylporphyrins, incorporation into a liposome membrane and interaction with a specific lectin Chem. Commun. 2009 224 226
11. S. Ballut, D. Naud-Martin, B. Loock, and Ph. Maillard A strategy for the targeting of photosensitizers. Synthesis, characterization, and photobiological property of porphyrins bearing glycodendrimeric moieties J. Org. Chem. 76 2011 2010 2028
12. S. Ballut, A. Makky, B. Chauvin, J.-P. Michel, A. Kasselouri, Ph. Maillard, and V. Rosilio Tumor targeting in photodynamic therapy. From glycoconjugated photosensitizers to glycodendrimeric one. Concept, design and properties Org. Biomol. Chem. 10 2012 4485 4495
13. J.T.C. Wojtyk, R. Goyan, E. Gudgin-Dickson, and R. Pottier Exploiting tumour biology to develop novel drug delivery strategies for PDT Med. Laser Appl. 21 2006 225 238 (Pubitemid 44740537)
14. W.M. Sharman, J.E. van Lier, and C.M. Allen Targeted photodynamic therapy via receptor mediated delivery systems Adv. Drug Del. Rev. 56 2004 53 76 (Pubitemid 38045424)
15. S.S. Stylli, and A.H. Kaye Photodynamic therapy of cerebral glioma - a review Part I - A biological basis J. Clin. Neurosci. 13 2006 615 625 (Pubitemid 44066804)
16. M. Ochsner Photophysical and photobiological processes in the photodynamic therapy of tumours J. Photochem. Photobiol. B, Biol. 39 1997 1 18 (Pubitemid 27285576)
17. 23Na MRI longitudinal follow-up of PDT in a xenograft model of human retinoblastoma Photodiagn. Photodyn. Therapy 6 2009 214 220
18. A. Bautista-Sanchez, A. Kasselouri, M.-C. Desroches, J. Blais, Ph. Maillard, D.-M. de Oliveira, A.C. Tedesco, P. Prognon, and J. Delaire Photophysical properties of glucoconjugated chlorins and porphyrins and their associations with cyclodextrins J. Photochem. Photobiol. B, Biol. 81 2005 154 162 (Pubitemid 41722587)
19. J.D. Krass, B. Jastorff, and H.-G. Genieser Determination of lipophilicity by gradient elution high-performance liquid chromatography Anal. Chem. 69 1997 2575 2585
20. M.-C. Desroches, A. Bautista-Sanchez, C. Lamotte, B. Labeque, D. Auchre, R. Farinotti, Ph. Maillard, D.S. Grierson, P. Prognon, and A. Kasselouri Pharmacokinetics of a tri-glucoconjugated 5,10,15-(meta)-trihydroxyphenyl-20- phenyl porphyrin photosensitizer for PDT. A single dose study in the rat J. Photochem. Photobiol. B. Biol. 85 2006 56 64 (Pubitemid 44350103)
21. Q. Wang, H.J. Altermatt, H.B. Ris, B.E. Reynolds, J.C. Stewart, R. Bonnett, and C.K. Lim Determination of 5,10,15,20-tetra-(m-hydroxyphenyl)chlorin in tissues by high performance liquid chromatography Biomed. Chromatogr. 7 1993 155 157 (Pubitemid 23160949)
22. M. Kongshaug, and J. Moan Separation of lipoproteins, albumin and γ-globulin by single-step ultracentrifugation of human serum. Application I: Binding of hematoporphyrin to human serum and to albumin Int. J. Biochem. Cell Biol. 27 1995 371 384
23. I. Laville, S. Pigaglio, J.-C. Blais, B. Loock, Ph. Maillard, D.S. Grierson, and J. Blais A study of the stability of tri(glucosyloxyphenyl) chlorin, a sensitizer for photodynamic therapy, in human colon tumoural cells: a liquid chromatography and MALDI-TOF mass spectrometry analysis Bioorg. Med. Chem. 12 2004 3673 3682 (Pubitemid 38746870)
24. Ph. Maillard, B. Loock, D.S. Grierson, I. Laville, J. Blais, F. Doz, L. Desjardins, D. Carrez, J.-L. Guerquin-Kern, and A. Croisy In vitro phototoxicity of glycoconjugated porphyrins and chlorins in colorectal adenocarcinoma (HT29) and retinoblastoma (Y79) cell lines Photodiagn. Photodyn. Therapy 4 2007 261 268 (Pubitemid 350161878)
25. T. Mosmann Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays J. Immunol. Meth. 65 1983 55 63 (Pubitemid 14203433)
26. H. Ibrahim, A. Kasselouri, C. You, Ph. Maillard, V. Rosilio, R. Pansu, and P. Prognon Meso-tetraphenyl porphyrin derivatives: the effect of structural modifications on binding to DMPC liposomes and albumin J. Photochem. Photobiol. A: Chem. 217 2011 10 21
27. S. Ballut, Personal communication, 2011.
28. D. Oulmi, Ph. Maillard, C. Vever-Bizet, M. Momenteau, and D. Brault Glycosylated porphyrins: characterization of association in aqueous solutions by absorption and fluorescence spectroscopies and determination of singlet oxygen yield in organic media Photochem. Photobiol. 67 1998 511 518 (Pubitemid 128472273)
29. I. Laville, T. Figueiredo, B. Loock, S. Pigaglio, Ph. Maillard, D.S. Grierson, D. Carrez, A. Croisy, J. Blais, and Synthesis Cellular internalization and photodynamic activity of glucoconjugated derivatives of tri and tetra(meta-hydroxyphenyl)chlorins Bioorg. Med. Chem. 11 2003 1643 1652 (Pubitemid 36349145)
30. A.P. Castano, T.N. Demidova, and M.R. Hamblin Mechanisms in photodynamic therapy: Part III - Photosensitizer pharmacokinetics, biodistribution, tumor localization and modes of tumor destruction Photodiagn. Photodyn. Therapy 2 2005 91 106 (Pubitemid 41160479)
31. M. Kongshaug, J. Moan, and S.B. Brown The distribution of porphyrins with different tumour localising ability among human plasma proteins Br. J. Cancer 59 1989 184 188 (Pubitemid 19072714)
32. A. Makky, J.-P. Michel, A. Kasselouri, E. Biand, Ph. Maillard, and V. Rosilio Evaluation of the specific interactions between glycodendrimeric porphyrins, free or incorporated into liposomes, and concanavaline a by fluorescence spectroscopy, surface pressure, and QCM-D measurements Langmuir 26 2010 12761 12768
33. R.M. Bohmer, and G. Morstyn Uptake of hematoporphyrin derivative by normal and malignant cells: effect of serum, pH, temperature, and cell size Cancer Res. 45 1985 5328 5334 (Pubitemid 16200840)
34. M. Korbelik, J. Hung, S. Lam, and B. Palcic The effects of low density lipoproteins on the uptake of Photofrin II Photochem. Photobiol. 51 1990 191 196
35. M. Korbelik, and J. Hung Cellular delivery and retention of Photofrin II: The effects of interaction with human plasma proteins Photochem. Photobiol. 53 1991 501 510