New peptide-conjugated chlorin-type photosensitizer targeting neuropilin-1 for anti-vascular targeted photodynamic therapy

International Journal of Molecular Sciences

Volumn 16, Issue 10, 2015, Pages 24059-24080

  Kamarulzaman, Ezatul Ezleen ^a,b,c   Gazzali, Amirah Mohd ^a,b,c   Acherar, Samir ^a,b   Frochot, Céline ^b,d   Barberi Heyob, Muriel ^b,e   Boura, Cédric ^b,e   Chaimbault, Patrick ^b,f   Sibille, Estelle ^g   Wahab, Habibah A ^c   Vanderesse, Régis ^a,b  

^a CNRS   (France)

^b UNIVERSITÉ DE LORRAINE   (France)

^c SCHOOL OF PHARMACEUTICAL SCIENCES   (Malaysia)

^d UNIVERSITÉ DE LORRAINE   (France)

^e CENTRE DE RECHERCHE EN AUTOMATIQUE DE NANCY   (France)

^f NANCY UNIVERSITÉ   (France)

^g UNIVERSITÉ DE LORRAINE   (France)

Author keywords

In vivo stability; Neuropilin 1; Peptide targeted photosensitizer; Photodynamic therapy

Indexed keywords

1 AMINO 3,6 DIOXAOCTANOIC ACID; 1 AMINO 9 AZA 3,6,12,15 TETRAOXA 10 ON HEPTADECANOIC ACID; 5 (4 CARBOXYPHENYL) 10,15, 20 TRIPHENYL CHLORINE; 5 (4 CARBOXYPHENYL) 10,15,20 TRIPHENYLPORPHYRIN; AMINOCAPROIC ACID; NEUROPILIN 1; OXYGEN; PENTAPEPTIDE; PHOTOSENSITIZING AGENT; UNCLASSIFIED DRUG; 5-(4-CARBOXYPHENYL)-10,15,20-TRIPHENYLCHLORIN; MACROGOL DERIVATIVE; PEPTIDE; PORPHYRIN; PROTEIN BINDING; VASCULAR ENDOTHELIAL GROWTH FACTOR A, MOUSE; VASCULOTROPIN A;

ABSORPTION SPECTROSCOPY; ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; BLOOD ANALYSIS; CHEMICAL ANALYSIS; CONJUGATION; CONTROLLED STUDY; DRUG STABILITY; ENZYME LINKED IMMUNOSORBENT ASSAY; FEMALE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; IC50; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MOUSE; NEOPLASM; NONHUMAN; PARTITION COEFFICIENT; PHOTODYNAMIC THERAPY; PHOTOOXIDATION; SYNTHESIS; TISSUE DISTRIBUTION; ANIMAL; CHEMISTRY; DISEASE MODEL; METABOLISM; NEOPLASMS; NUDE MOUSE; PHOTOCHEMOTHERAPY; PROCEDURES;

ANIMALS; DISEASE MODELS, ANIMAL; FEMALE; MICE; MICE, NUDE; NEOPLASMS; NEUROPILIN-1; OXYGEN; PEPTIDES; PHOTOCHEMOTHERAPY; PHOTOSENSITIZING AGENTS; POLYETHYLENE GLYCOLS; PORPHYRINS; PROTEIN BINDING; VASCULAR ENDOTHELIAL GROWTH FACTOR A;

EID: 84944042619     PISSN: 16616596     EISSN: 14220067     Source Type: Journal    
DOI: 10.3390/ijms161024059     Document Type: Article

References (30)

1. Dougherty, T.J.; Gomer, C.J.; Henderson, B.W.; Jori, G.; Kessel, D.; Korbelik, M.; Moan, J.; Peng, Q. Photodynamic therapy. J. Natl. Cancer Inst. 1998, 90, 889-905.
2. Bechet, D.; Tirand, L.; Faivre, B. Neuropilin-1 targeting photosensitization-induced early stages of thrombosis via tissue factor release. Pharm. Res. 2010, 27, 468-479.
3. Mukai, H.; Yasuhiro, W.; Watanabe, Y. The synthesis of 64Cu-chelated porphyrin photosensitizers and their tumor-targeting peptide conjugates for the evaluation of target cell uptake and PET image-based pharmacokinetics of targeted photodynamic therapy agents. Ann. Nucl. Med. 2013, 27, 625-639.
4. Lafont, D.; Zorlu, Y.; Savoie, H.; Albrieux, F.; Ahsen, V.; Boyle, R.W.; Dumoulin, F. Monoglycoconjugated phthalocyanines: Effect of sugar and linkage on photodynamic activity. Photodiagn. Photodyn. Ther. 2013, 10, 252-259.
5. Mazière, J.C.; Morlière, P.; Santus, R. The role of the low density lipoprotein receptor pathway in the delivery of lipophilic photosensitizers in the photodynamic therapy of tumours. J. Photochem. Photobiol. B 1991, 8, 351-360.
6. Schmidt-Erfurth, U.; Diddens, H.; Birngruber, R.; Hasan, T. Photodynamic targeting of human retinoblastoma cells using covalent low-density lipoprotein conjugates. Br. J. Cancer 1997, 75, 54-61.
7. Mew, D.; Wat, C.K.; Towers, G.H.; Lew, J.G. Photoimmunotherapy: Treatment of animal tumors with tumor-specific monoclonal antibody-hematoporphyrin conjugates. J. Immunol. 1983, 130, 1473-1477.
8. Bryden, F.; Maruani, A.; Savoie, H.; Chudasama, V.; Smith, M.E.B.; Caddick, S.; Boyle, R.W. Regioselective and stoichiometrically controlled conjugation of photodynamic sensitizers to a HER2 targeting antibody fragment. Bioconjug. Chem. 2014, 25, 611-617.
9. Gupta, S.; Dwarakanath, B.S.; Chaudhury, N.K.; Mishra, A.K.; Muralidhar, K.; Jain, V. In vitro and in vivo targeted delivery of photosensitizers to the tumor cells for enhanced photodynamic effects. J. Cancer Res. Ther. 2011, 7, 310-320.
10. Lovell, J.F.; Liu, T.W.B.; Chen, J.; Zheng, G. Activatable Photosensitizers for Imaging and Therapy. Chem. Rev. 2010, 110, 2839-2857.
11. Schneider, R.; Tirand, L.; Frochot, C.; Vanderesse, R.; Thomas, N.; Gravier, J.; Guillemin, F.; Barberi-Heyob, M. Recent improvements in the use of synthetic peptides for a selective photodynamic therapy. Anticancer Agents Med. Chem. 2006, 6, 469-488.
12. Tirand, L.; Frochot, C.; Vanderesse, R.; Thomas, N.; Trinquet, E.; Pinel, S.; Viriot, M.L.; Guillemin, F.; Barberi-Heyob, M. A peptide competing with VEGF165 binding on neuropilin-1 mediates targeting of a chlorin-type photosensitizer and potentiates its photodynamic activity in human endothelial cells. J. Control. Release 2006, 111, 153-164.
13. Tirand, L.; Thomas, N.; Dodeller, M.; Dumas, D.; Frochot, C.; Maunit, B.; Guillemin, F.; Barberi-Heyob, M. Metabolic profile of a peptide-conjugated chlorin-type photosensitizer targeting neuropilin-1: An in vivo and in vitro study. Drug Metab. Dispos. 2007, 35, 806-813.
14. Thomas, N.; Bechet, D.; Becuwe, P.; Tirand, L.; Vanderesse, R.; Frochot, C.; Guillemin, F.; Barberi-Heyob, M. Peptide-conjugated chlorin-type photosensitizer binds neuropilin-1 in vitro and in vivo. J. Photochem. Photobiol. B 2009, 96, 101-108.
15. Garcia, G.; Naud-Martin, D.; Carrez, D.; Croisy, A.; Maillard, P. Microwave-mediated "click-chemistry" synthesis of glycoporphyrin derivatives and in vitro photocytotoxicity for application in photodynamic therapy. Tetrahedron 2011, 67, 4924-4932.
16. Chu, E.S.M.; Wong, T.K.S.; Yow, C.M.N. Photodynamic effect in medulloblastoma: downregulation of matrix metalloproteinases and human telomerase reverse transcriptase expressions. Photochem. Photobiol. Sci. 2008, 7, 76-83.
17. Olivo, M.; Bhuvaneswari, R.; Lucky, S.S.; Dendukuri, N.; Thong, S-P.P. Targeted therapy of cancer using photodynamic therapy in combination with multi-faceted anti-tumor modalities. Pharmaceuticals 2010, 3, 1507-1529.
18. Thomas, N.; Pernot, M.; Vanderesse, R.; Becuwe, P.; Kamarulzaman, E.; Da Silva, D.; Francois, A.; Frochot, C.; Guillemin, F.; Barberi-Heyob, M. Photodynamic therapy targeting neuropilin-1: Interest of pseudopeptides with improved stability properties. Biochem. Pharmacol. 2010, 80, 226-235.
19. Thomas, N.; Tirand, L.; Chatelut, E.; Plénat, F.; Frochot, C.; Dodeller, M.; Guillemin, F.; Barberi-Heyob, M. Tissue distribution and pharmacokinetics of an ATWLPPR-conjugated chlorin-type photosensitizer targeting neuropilin-1 in glioma-bearing nude mice. Photochem. Photobiol. Sci. 2008, 7, 433-441.
20. Kamarulzaman, E.E.; Vanderesse, R.; Mohd Gazzali, A.; Barberi-Heyob, M.; Boura, C.; Frochot, C.; Shawkataly, O.; Aubry, A.; Wahab, H.A. Molecular modelling, synthesis and biological evaluation of peptide inhibitors as anti-angiogenic agent targeting Neuropilin-1 for anticancer application. J. Biomol. Struct. Dyn. 2015, in press.
21. Von Wronski, M.A.; Raju, N.; Pillai, R.; Bogdan, N.J.; Marinelli, E.R.; Nanjappan, P.; Ramalingam, K.; Arunachalam, T.; Eaton, S.; Linder, K.E.; et al. Tuftsin binds neuropilin-1 through a sequence similar to that encoded by exon 8 of vascular endothelial growth factor. J. Biol. Chem. 2006, 281, 5702-5710.
22. Cebe-Suarez, S.; Grunewald, F.S.; Jaussi, R.; Li, X.J.; Claesson-Welsh, L.; Spillmann, D.; Mercer, A.A.; Prota, A.E.; Ballmer-Hofer, K. Orf virus VEGF-E NZ2 promotes paracellular NRP-1/VEGFR-2 coreceptor assembly via the peptide RPPR. FASEB J. 2008, 22, 3078-3086.
23. Allain, B.; Jarray, R.; Borriello, L.; Leforban, B.; Dufour, S.; Liu, W.-Q.; Pamonsinlapatham, P.; Bianco, S.; Larghero, J.R.M.; Hadj-Slimane, R.D.; et al. Neuropilin-1 regulates a new VEGF-induced gene, Phactr-1, which controls tubulogenesis and modulates lamellipodial dynamics in human endothelial cells. Cell. Signal. 2012, 24, 214-223.
24. Figueiredo, T.L.C.; Johnstone, R.A.W.; SantAna Sorensen, A.M.P.; Burget, D.; Jacques, P. Determination of fluorescence yields, singlet lifetimes and singlet oxygen yields of water-insoluble porphyrins and metalloporphyrins in organic solvents and in aqueous media. Photochem. Photobiol. 1999, 69, 517-528.
25. DeRosa, M.C.; Crutchley, R.J. Photosensitized singlet oxygen and its applications. Coord. Chem. Rev. 2002, 233, 351-371.
26. Engel, A.; Chatterjee, S.K.; Al-Arifi, A.; Nuhn, P. Influence of Spacer Length on the Agglutination of Glycolipid-Incorporated Liposomes by ConA as Model Membrane. J. Pharm. Sci. 2003, 92, 2229-2235.
27. Kostenich, G.; Livnah, N.; Bonasera, T.A.; Yechezkel, T.; Salitra, Y.; Litman, P.; Kimel, S.; Orenstein, A. Targeting small-cell lung cancer with novel fluorescent analogs of somatostatin. Lung Cancer 2005, 50, 319-328.
28. Schneider, R.; Schmitt, F.; Frochot, C.; Fort, Y.; Lourette, N.; Guillemin, F.; Müller, J.F.; Barberi-Heyob, M. Design, synthesis, and biological evaluation of folic acid targeted tetraphenylporphyrin as novel photosensitizers for selective photodynamic therapy. Bioorg. Med. Chem. 2005, 13, 2799-2808.
29. Bonnett, R.; White, R.D.; Winfield, U.J.; Berenbaum, M.C. Hydroporphyrins of the meso-tetra(hydroxyphenyl)porphyrin series as tumour photosensitizers. Biochem. J. 1989, 261, 277-280.
30. Whitlock, H.W., Jr.; Hanauer, R.; Oester, M.Y.; Bower, B.K. Diimide reduction of porphyrins. J. Am. Chem. Soc. 1969, 91, 7485-7489.