Synthesis of new glucosylated porphyrins bearing an α-D-linkage

Journal of Carbohydrate Chemistry

Volumn 25, Issue 4, 2006, Pages 345-360

  Sol, Vincent ^a   Charmot, Alexandre ^a   Krausz, Pierre ^a   Trombotto, Stéphane ^b   Queneau, Yves ^c  

^a UNIVERSITÉ DE LIMOGES   (France)

^b Laboratoire des Materiaux Polymeres et des Biomateriaux UMR 5627   (France)

^c UNIVERSITÉ LYON 1   (France)

Author keywords

Isomaltulose; Photodynamic therapy; Porphyrins; D glucose

Indexed keywords

EID: 33745793414     PISSN: 07328303     EISSN: 15322327     Source Type: Journal    
DOI: 10.1080/07328300600770527     Document Type: Article

References (24)

1. Cornia, M.; Casiraghi, G.; Binacchi, S.; Zanardi, F.; Rassu, G. Facile entry to 5,10,15,20-tetra-C-glycosylporphyrins. J. Org. Chem. 1994, 59, 1226-1230.
2. Momenteau, M.; Oulmi, D.; Maillard, P.; Croisy, A. In vitro photobiological activity of a new series of photosensitizers: the glycoconjugated porphyrins. SPIE, Photodynamic Therapy Cancer II. 1994, 2325, 13-23.
3. Hombrecher, H.K.; Ohm, S.; Koll, D. Synthesis of galactopyranosyl substituted porphyrins. Tetrahedron 1996, 52, 5441-5448.
4. Sol, V.; Blais, J.C.; Bolbach, G.; Carré, V.; Granet, R.; Guilloton, M.; Spiro, M.; Krausz, P. Toward glycosylated peptidic porphyrins: a new strategy for PDT? Tetrahedron Lett. 1997, 38, 6391-6394.
5. Mikata, Y.; Onchi, Y.; Tabata, K.; Ogura, S.; Okura, I.; Ono, H.; Yano, S. Sugar-dependent photocytotoxic property of tetra- and octa-glycoconjugated tetraphenylporphyrins. Tetrahedron Lett. 1998, 39, 4505-4508.
6. Schell, C.; Hombrecher, H.K. Synthesis, self-assembly properties and incorporation of carbohydrate-substituted porphyrins into cell membrane models. Chem. Eur. J. 1999, 5, 587-598.
7. Sol, V.; Blais, J.C.; Carré, V.; Granet, R.; Guilloton, M.; Spiro, M.; Krausz, P. Synthesis, spectroscopy and photocytotoxicity of glycosylated amino acid porphyrins derivatives as promising molecules for cancer phototherapy. J. Org. Chem. 1999, 64, 4431-4444.
8. Zheng, G.; Graham, A.; Shibata, M.; Missert, J.R.; Oseroff, A.R.; Dougherty, T.J.; Pandey, R.K. Synthesis of β-galactose-conjugated chlorins derivated by enyme metathesis as galectin-specific photosensitizers for photodynamic therapy. J. Org. Chem. 2001, 66, 8709-8716.
9. Laville, I.; Figueiredo, T.; Loock, B.; Pigaglio, S.; Maillard, P.; Grierson, D.S.; Sarrez, C.D.; Croisy, A.; Blais, J. Synthesis, cellular internalization and photodynamic activity of glucoconjugated derivated of tri and tetra(meta-hydroxyphenyl)-chlorins. Bioorg. Med. Chem. 2003, 11, 1643-1652.
10. Sylvain, I.; Benhaddou, R.; Carré, V.; Cottaz, S.; Driguez, H.; Granet, R.; Guilloton, M.; Krausz, P. Synthesis and biological evaluation of thioglycosylated meso-arylporphyrins. J. Porphyrins Phthalocyanines 1999, 3, 1-4.
11. Chaleix, V.; Sol, V.; Huang, Y-M.; Guilloton, M.; Granet, R.; Blais, J.C.; Krausz, P. RGD-porphyrin conjugates: synthesis and potential application in photodynamic therapy. Eur. J. Org. Chem. 2003, 1486-1493.
12. Kieda, C.; Monsigny, M. Involvement of membrane sugar receptors and membrane glycoconjugates in the adhesion of 3LL cell subpopulations to cultured pulmonary cells. Invasion Metastasis 1986, 6, 347-366.
13. Monsigny, M.; Roche, A.C.; Midoux, P.; Kieda, C.; Mayer, R. Lectins and Glycoconjugates in Oncolog: Structure, Function, Clinical Application. Gabius, H.J. and Nagel, G.A. Ed: Spinger-Verlag, Heidelberg., 1988, 1.
14. Fujimoto, K.; Miyata, T.; Aoyama, Y. Saccharide-directed cell recognition and molecular delivery using macrocyclic saccharide clusters: masking of hydrophobicity to enhance the saccharide specificity. J. Am. Chem. Soc. 2000, 122, 3358-3359.
15. Ono, N.; Bougauchi, M.; Maruyama, K. Water-soluble porphyrins with four sugar molecules. Tetrahedron. Lett. 1992, 33, 1629-1632.
16. Lee, Y.C.; Lee, R.T. Affinity enhancement by multivalent lectin-carbohydrate interaction Glycoconjug. J. 2000, 17, 543-551.
17. Trombotto, S.; Bouchu, A.; Descotes, G.; Queneau, Y. Hydrogen peroxide oxidation of palatinose and trehalulose: direct preparation of carboxymethyl α-D-glucopyranoside. Tetrahedron Lett. 2000, 41, 8273-8277.
18. Trombotto, S.; Danel, M.; Fitremann, J.; Bouchu, A.; Queneau, Y. Straightforward route for anchoring a glucosyl moiety onto nucleophilic species: reaction of amines and alcohols with carboxymethyl 3,4,6 tri-O-acetyl-α- D-glucopyranoside 2-O-lactone. J. Org. Chem, 2003, 68, 6672-6678.
19. Little, R.G.; Anton, J.A.; Loach, P.A.; Ibers, J-A. The synthesis of some substituted tetraalkylporphyrins. J. Heterocycl. Chem. 1975, 12, 345-349.
20. Furhop, J.H.; Demoulin, C.; Boettcher, C.; Koning, J.; Siggel, U. Chiral micellar porphyrin fibers with 2-aminoglycosamide head groups. J. Am. Chem. Soc. 1992, 114, 4159-4165.
21. Barber, D.C.; Freitag-Beeston, R.A.; Whitten, D.G. Atropisomer-specific formation of premicellar porphyrin J-aggregates in aqueous surfactant solutions. J. Phys. Chem. 1991, 95, 4074-4086.
22. Ohloff, G. Singlet oxygen: a reagent in organic synthesis Pure. Appl. Chem. 1975, 43, 481-502.
23. Albro, P.W.; Corbett, J.T.; Shroeder, J.L. Doubly allylic hydroperoxide formed in the reaction between sterol 5,7 dienes and singlet oxygen. Photochem. Photobiol. 1994, 60, 310-315.
24. Böcking, T.; Barrow, K.D.; Netting, A.G.; Chilcott, T.C.; Coster, H.G.; Höfer, M. Effect of singlet oxygen on membrane sterols in the yeast saccharomyces cerevisiae. Eur. J. Biochem. 2000, 267, 1607-1618.