Synthesis and photophysics of an octathioglycosylated zinc(II) phthalocyanine

Tetrahedron Letters

Volumn 52, Issue 42, 2011, Pages 5456-5459

  Aggarwal, Amit ^a   Singh, Sunaina ^a   Zhang, Yazhou ^b   Anthes, Mariah ^a   Samaroo, Diana ^c   Gao, Ruomei ^b   Drain, Charles Michael ^a,d  

^a CITY UNIVERSITY OF NEW YORK   (United States)

^b JACKSON STATE UNIVERSITY   (United States)

^c CITY UNIVERSITY OF NEW YORK   (United States)

^d ROCKEFELLER UNIVERSITY   (United States)

Author keywords

Fluorescence; Glucose; Photodynamic therapy; Phthalocyanine; Quantum yield

Indexed keywords

DICHLOROMETHANE; PHTHALOCYANINE; PHTHALOCYANINE ZINC; THIOGLUCOSE;

ABSORPTION; ARTICLE; CANCER CELL; CELL AGGREGATION; CHEMICAL ANALYSIS; CONTROLLED STUDY; GLYCOSYLATION; HYDROLYSIS; NUCLEOPHILICITY; PHOTOCHEMISTRY; PHOTODEGRADATION; PHOTODYNAMIC THERAPY; PROTON NUCLEAR MAGNETIC RESONANCE; SUBSTITUTION REACTION; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY;

EID: 80052809120     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.08.028     Document Type: Article

References (60)

1. Y. Zorlu, M.A. Ermeydan, F. Dumoulin, V. Ahsen, H. Savoie, and R.W. Boyle Photochem. Photobiol. Sci. 8 2009 312 318
2. L.B. Josefsen, and R.W. Boyle Metal-Based Drugs 2008 2008 276109
3. P. Zhang, S. Zhang, and G. Han Molecules 14 2009 3688 3693
4. R. van Hillegersberg, W.J. Kort, and J.H.P. Wilson Drugs 48 1994 510 527
5. R. Bonnett, and G. Martínez Tetrahedron 57 2001 9513 9547
6. I.J. Macdonald, and T.J. Dougherty J. Porphyrins Phthalocyanines 5 2001 105 129
7. J.E. van Lier, and J.D. Spikes Photosensitizing Compounds: Their Chemistry Biology and Clinical Use G. Block, S. Harnett, CIBA Foundation Symposium 146 vol. 17 1989 Wiley Chichester 17 39
8. C.M. Allen, W.M. Sharman, and J.E. Van Lier J. Porphyrins Phthalocyanines 5 2001 161 169
9. H. Ali, and J.E. van Lier Chem. Rev. 99 1999 2379 2450
10. S. Arslan, and I. Yilmaz Polyhedron 26 2007 2387 2394
11. H.A. Diner, A. Koca, A. Gül, and M.B. Koak Dyes Pigments 76 2008 825 831
12. B.S. Sesalan, A. Koca, and A. Gül Dyes Pigments 79 2008 259 264
13. R.W. Boyle, C.C. Leznoff, and J.E. van Lier Br. J. Cancer 67 1993 1177 1181
14. R.E. Airley, and A. Mobasheri Chemotherapy 53 2007 233 256
15. O. Warburg Science 123 1956 309 314
16. A. Toschi, E. Lee, S. Thompson, N. Gadir, P. Yellen, C.M. Drain, M. Ohh, and D.A. Foster Cancer Lett. 299 2010 72 79
17. X. Chen, L. Hui, D.A. Foster, and C.M. Drain Biochem. 43 2004 10918 10929
18. P. Pasetto, X. Chen, C.M. Drain, and R.W. Franck Chem. Commun. 2001 81 82
19. S. Thompson, X. Chen, L. Hui, A. Toschi, D.A. Foster, and C.M. Drain Photochem. Photobio. Sci. 7 2008 1415 1421
20. S. Singh, A. Aggarwal, S. Thompson, J.P.C. Tomé, X. Zhu, D. Samaroo, M. Vinodu, R. Gao, and C.M. Drain Bioconjugate Chem. 21 2010 2136 2146
21. G. Li, S.K. Pandey, A. Graham, M.P. Dobhal, R. Mehta, Y. Chen, A. Gryshuk, K. Rittenhouse-Olson, A. Oseroff, and R.K. Pandey J. Org. Chem. 69 2004 158 172
22. K. Fujimoto, T. Miyata, and Y. Aoyama J. Am. Chem. Soc. 122 2000 3558 3559
23. X. Álvarez-Micó, M.J.F. Calvete, M. Hanack, and T. Ziegler Synthesis 14 2007 2186 2192
24. C.-F. Choi, J.-D. Huang, P.-C. Lo, W.-P. Fong, and D.K.P. Ng Org. Biomol. Chem. 6 2008 2173 2181
25. J.-Y. Liu, P.-C. Lo, W.-P. Fong, and D.K.P. Ng Org. Biomol. Chem. 7 2009 1583 1591
26. X. Alvarez-Mico, M.J.F. Calvete, M. Hanack, and T. Ziegler Tetrahedron Lett. 47 2006 3283 3286
27. A.O. Ribeiro, J.P.C. Tomé, M.G.P.M.S. Neves, A.C. Tomé, J.A.S. Cavaleiro, Y. Iamamoto, and T. Torres Tetrahedron Lett. 47 2006 9177 9180
28. P. Maillard, S. Gaspard, J.L. Guerquin-Kern, and M. Momenteau J. Am. Chem. Soc. 111 1989 9125 9127
29. A. Lyubimtsev, Z. Iqbal, G. Crucius, S. Syrbu, E.S. Taraymovich, T. Ziegler, and M. Hanack J. Porphyrins Phthalocyanines 15 2011 39 46
30. Z. Iqbal, M. Hanack, and T. Ziegler Tetrahedron Lett. 50 2009 873 875
31. X. Álvarez-Micó, M.J.F. Calvete, M. Hanack, and T. Ziegler Carbohydrate Res. 342 2007 440 447
32. Z. Iqbal, A. Lyubimtsev, M. Hanack, and T. Ziegler J. Porphyrins Phthalocyanines 14 2010 494 498
33. A.R.M. Soares, J.P.C. Tomé, M.G.P.M.S. Neves, A.C. Tomé, J.A.S. Cavaleiro, and T. Torres Carbohydrate Res. 344 2009 507 510
34. J.-p. Taquet, C. Frochot, V. Manneville, and M. Barberi-Heyob Curr. Med. Chem. 14 2007 1673 1687
35. D. Samaroo, M. Vinodu, X. Chen, and C.M. Drain J. Combi. Chem. 9 2007 998 1011
36. C.M. Drain, S. Singh, K. Kadish, R. Guilard, and K. Smith Combinatorial Chemistry of Porphyrins. in The Handbook of Porphyrin Science with Applications to Chemistry, Physics, Materials Science, Engineering, Biology and Medicine vol. 2 2010 World Scientific Singapore 485 540
37. T. Goslinski, T. Osmalek, K. Konopka, M. Wierzchowski, P. Fita, and J. Mielcarek Polyhedron 30 2011 1538 1546
38. S. Vedachalam, B.-H. Choi, K.K. Pasunooti, K.M. Ching, K. Lee, H.S. Yoon, and X.-W. Liu Med. Chem. Commun. 2 2011 371 377
39. I. Laville, S. Pigaglio, J.C. Blais, B. Loock, P. Maillard, D.S. Grierson, and J. Blais Bioorg. Med. Chem. 12 2004 3673 3682
40. X. Zheng, and R.K. Pandey Anti-Cancer Agents Med. Chem. 8 2008 241 268
41. M.G. Vander Heiden, L.C. Cantley, and C.B. Thompson Science 324 2009 1029 1033
42. M. Cornia, M. Menozzi, E. Ragg, S. Mazzini, A. Scarafoni, F. Zanardi, and G. Casiraghi Tetrahedron 56 2000 3977 3983
43. S. Ahmed, E. Davoust, H. Savoie, A.N. Boa, and R.W. Boyle Tetrahedron Lett. 45 2004 6045 6047
44. C.C. Leznoff, A. Hiebert, and S. Ok J. Porphyrins Phthalocyanines 11 2007 537 546
45. C.C. Leznoff, and J.L. Sosa-Sanchez Chem. Commun. 2004 338 339
46. V.N. Nemykin, and E.A. Lukyanets Key Role of peripheral substitution in the chemistry of phthalocyanines K. Kadish, R. Guilard, K. Smith, The Handbook of Porphyrin Science with Applications to Chemistry, Physics, Materials Science, Engineering, Biology and Medicine Vol. 3 2010 World Scientific Singapore 1 323
47. E.A. Lukyanets, and V.N. Nemykin J. Porphyrins Phthalocyanines 14 2010 1 40
48. A. Varotto, C.-Y. Nam, I. Radivojevic, J.P.C. Tomé, J.A.S. Cavaleiro, C.T. Black, and C.M. Drain J. Am. Chem. Soc. 132 2010 2552 2554
49. P. Tau, A.O. Ogunsipe, S. Maree, M.D. Maree, and T. Nyokong J. Porphyrins Phthalocyanines 7 2003 439 446
50. C.M. Drain, G. Smeureanu, S. Patel, X. Gong, J. Garno, and J. Arijeloye New J. Chem. 30 2006 1834 1843
51. X.C. Gong, T. Milic, C. Xu, J.D. Batteas, and C.M. Drain J. Am. Chem. Soc. 124 2002 14290 14291
52. A. Ogunsipe, J.-Y. Chen, and T. Nyokong New. J. Chem. 28 2004 822 827
53. D. Atilla, M. Durmus, A.G. Gürek, V. Ahsena, and T. Nyokong Dalton Trans. 2007 1235 1243
54. A.C. Beveridge, B.A. Bench, S.M. Gorun, and G.J. Diebold J. Phys. Chem. A 107 2003 5138 5143
55. T. Nyokong Coord. Chem. Rev. 251 2007 1707 1722
56. W. Li, N. Gandra, E. Ellis, S. Cartney, and R.A.C.S. Gao Appl. Mater. Interfaces 1 2009 1778 1784
57. W. Li, N. Gandra, S.N. Courtney, and R. Gao ChemPhysChem 10 2009 1789 1793
58. Y. Zhang, X. Zhu, J. Smith, M.T. Haygood, and R. Gao J. Phys. Chem. B 115 2011 1889 1894
59. D. Bechet, P. Couleaud, C. Frochot, M.-L. Viriot, F. Guillemin, and M. Barberi-Heyob Trends in Biotechnology 26 2008 612 621
60. A. Busetti, M. Soncin, E. Reddi, M.A.J. Rodgers, M.E. Kenney, and G. Jori J. Photochem. Photobiol. B: Biol. 53 1999 103 109