ArticlesNo Access

Aggregation behavior and UV-vis spectra of tetra- and octaglycosylated zinc phthalocyanines

Alexey Lyubimtsev

Institut für Organische Chemie der Universität Tübingen, Auf der Morgenstelle 18, 72076 Tübingen, Germany

Ivanovo State University of Chemistry and Technology, F. Engels str. 7, 15300 Ivanovo, Russia

Search for more papers by this author

Zafar Iqbal

Institut für Organische Chemie der Universität Tübingen, Auf der Morgenstelle 18, 72076 Tübingen, Germany

Karakoram International University, Department of Chemistry, Gilgit, Pakistan

Search for more papers by this author

Göran Crucius

Institut für Organische Chemie der Universität Tübingen, Auf der Morgenstelle 18, 72076 Tübingen, Germany

Search for more papers by this author

Sergey Syrbu

Ivanovo State University of Chemistry and Technology, F. Engels str. 7, 15300 Ivanovo, Russia

Search for more papers by this author

Ekaterina S. Taraymovich

Institut für Organische Chemie der Universität Tübingen, Auf der Morgenstelle 18, 72076 Tübingen, Germany

Ivanovo State University of Chemistry and Technology, F. Engels str. 7, 15300 Ivanovo, Russia

Search for more papers by this author

Thomas Ziegler

Institut für Organische Chemie der Universität Tübingen, Auf der Morgenstelle 18, 72076 Tübingen, Germany

Search for more papers by this author

, and

Michael Hanack

Institut für Organische Chemie der Universität Tübingen, Auf der Morgenstelle 18, 72076 Tübingen, Germany

Corresponding author, tel: +49 7071-2972432, fax: +49 7071-295268.

SPP full member in good standing.

Search for more papers by this author

https://doi.org/10.1142/S1088424611002891Cited by:52 (Source: Crossref)

Abstract

Several tetra- and octaglycosylated PcZn's 1a, 2a–2d, 3a-b and 4 were investigated for their aggregation behavior using different concentrations of the PcZn-species in pure DMSO, water and in various DMSO/water mixtures by comparing their UV-vis spectra. The PcZn's 1–4 are independent of the concentration in pure DMSO and in up to 25 vol.% water/DMSO mixtures are non aggregated. Increasing amounts of water leads to higher aggregation ratios. The aggregation behavior is influenced by the nature and the position of the sugar substituents on the Pc-ring. PcZn4 was found the least aggregated compound even in pure water.

Keywords:

Most comprehensive & up-to-date research on PORPHYRINS
Handbook of Porphyrin Science now available in 46 volumes

References

a) Soares A. R. M., Tome J. P. C., Neves M. G. P. M. S., Tome A. C., Cavaleiro J. A. S. and Torres T. Carbohydr. Res. 2009; 344: 507–510. b) Liu J.-Y., Lo P.-C., Fong W.-P. and Ng D. K. P. Org. Biomol. Chem. 2009; 7: 1583–1591. c) Kumru U., Ermeydan M. A., Dumoulin F. and Ahsen V. J. Porphyrins Phthalocyanines 2008; 12: 1090–1095. d) Ribeiro A. O., Tome J. P. C., Neves M. G. P. M. S., Tome A. C., Cavaleiro J. A. S., Iamamoto Y. and Torres T. Tetrahedron Lett. 2006; 47: 9177–9180. e) Choi C.-F., Huang J.-D., Lo P.-C., Fong W.-P. and Ng D. K. P. Org. Biomol. Chem. 2008; 6: 2173–2181. f) Lo P.-C., Chan C. M. H., Liu J.-Y., Fong W.-P. and Ng D. K. P. J. Med. Chem. 2007; 50: 2100–2107. g) Reddy M. R., Shibata N., Yoshiyama H., Nakamura S. and Toru T. Synlett 2007; 628–632. h) Lee P., Lo C., Chan E., Fong W.-P., Ko W. H. and Ng D. K. P. Tetrahedron Lett. 2005; 46: 1551–1554. i) Zorlu Y., Ermeydan M. A., Dumoulin F., Ahsen V., Savoie H. and Boyle R. S. Photochem. Photobiol. Sci. 2009; 8: 312–318. j) Camerin M., Rello S., Villanueva A., Ping X., Kenney M. E., Rodgers M. A. J. and Jori G. Eur. J. Cancer 2005; 41: 1203–1212 . Google Scholar
R. Van Hillegersberg, W. Kort and J. Wilson, Drugs 48, 510 (1994). Crossref, Web of Science, Google Scholar
a) Ono N., Bougauchi M. and Maruyama K. Tetrahedron Lett. 1992; 33: 1629. b) Maillard P., Guerquin-Kern J. L., Huel C. and Momemteau M. J. Org. Chem. 1993; 58: 2774. c) Fujimoto K., Miyata T. and Aoyama Y. J. Am. Chem. Soc. 2000; 122: 3558. d) Chen X., Hui L., Foster D. and Drain C. Biochemistry 2004; 43: 10918. e) Li G., Pandey S., Graham A., Dobhal M., Ricky M., Chen Y., Gryshuk A., Rittenhouse-Olson K., Osero A. and Pandey R. J. Org. Chem. 2004; 69: 158 . Google Scholar
a) Chandler J., Williams E., Slavin J., Best J. and Rogers S. Cancer 2003; 97: 2035. b) Kumamoto K., Goto Y., Sekikawa K., Takenoshita S., Ishida N., Kawakita M. and Kannagi R. Cancer Res. 2001; 61: 4620 . Google Scholar
X. Alvarez-Micoet al., Tetrahedron Lett. 47, 3283 (2006), DOI: 10.1016/j.tetlet.2006.03.029. Crossref, Web of Science, Google Scholar
X. Alvarez-Micoet al., Synthesis 14, 2186 (2007). Google Scholar
Z. Iqbal, M. Hanack and T. Ziegler, Tetrahedron Lett. 50, 873 (2009). Crossref, Web of Science, Google Scholar
Z. Iqbalet al., Tetrahedron Lett. 50, 5681 (2009), DOI: 10.1016/j.tetlet.2009.07.127. Crossref, Web of Science, Google Scholar
Z. Iqbalet al., J. Porphyrins Phthalocyanines 14, 494 (2010), DOI: 10.1142/S1088424610002343. Link, Web of Science, Google Scholar
Z. Iqbalet al., Synthesis 18, 3097 (2010). Google Scholar
R. Edreiet al., J. Porphyrins Phthalocyanines 2, 191 (1998). Link, Web of Science, Google Scholar
B. C. Wilson and W. P. Jeeves, Photodynamic Therapy of Cancer 2, eds. E. Ben-Hur and I. Rosental (CRC Press, Boca Raton, 1987) p. 127. Google Scholar
a) Sinn H. J., Schrenk H.-H., Maier-Borst W., Friedrich E., Graschew G., Wöhrle D. and Klemmer T. Polyether-Substituted Anti-Tumor Agents; European Patent PCTlEP9lJOo992, 1991. b) Wöhrle D., Ardeschirpur A., Heuermann A., Müller S., Graschew G., Rinneberg H., Kohl M. and Neukammer J. Makromol. Chem. Makromol. Symp. 1992; 59: 17–33 . Google Scholar
a) Yates N. C., Moan J. and Western A. J. Photochem. Photobiol. B 1990; 4: 379–390. b) Wöhrle D., Shopova M., Mueller S., Milev A.D., Mantareva V. N. and Krastev K. K. J. Photochem. Photobiol. B 1993; 21: 155–165. c) Shopova M., Wöhrle D., Stoichkova N., Milev A., Mantareva V., Muller S., Kassabov K. and Georgiev K. J. Photochem. Photobiol. B 1994; 23: 35–42. d) Camerin M., Rello S., Villanueva A., Ping X., Kenney M. E., Rodgers M. A. J. and Jori G. Eur. J. Cancer 2005; 41: 1203–1212. e) Brasseur N., Nguyen T. L., Langlois R., Ouellet R., Marengo S., Houde D. and Van Lier J. E. J. Med. Chem. 1994; 37: 415–420. f) Sun W., Wang G., Li Y., Calvete M. J. F., Dini D. and Hanack M. J. Phys. Chem. A 2007; 111: 3263–3270 . Google Scholar
A. W. Snow, The Porphyrin Handbook-Phthalocyanines: Properties and Materials 17, eds. K. M. Kadish, K. M. Smith and R. Guilard (Academic Press, New York, 2003) pp. 129–176. Crossref, Google Scholar
M. J. Cooket al., J. Chem. Soc. Chem. Commun. 1086 (1987), DOI: 10.1039/c39870001086. Google Scholar
a) Li H., Nguyen N., Fronczek F. R. and Vincente M. G. H. Tertahedron 2009; 65: 3357–3363. b) Liu W., Jensen T. J., Fronczek F. R., Hammer R. P., Smith K. M. and Vicente M. G. H. J. Med. Chem. 2005; 48: 1033–1041. c) Li H., Jensen T. J., Fronczek F. R. and Vicente M. G. H. J. Med. Chem. 2008; 51: 502–511. d) Dhami S. and Phillips D. J. Photochem. Photobiol. A 1996; 100: 77–84. e) Sharman W. M., Kudrevich S. V. and Van Lier J. E. Tetrahedron Lett. 1996; 37: 5831–5834. f) Li H., Fronczek F. R. and Vicente M. G. H. Tetrahedron Lett. 2008; 49: 4828–4830. g) Sibrian-Vazquez M., Ortiz J., Nesterova IV, Fernandez-Lazaro F., Sastre-Santos A., Soper S. A. and Vicente M. G. H. Bioconjugate Chem. 2007; 18: 410–420. h) Li H., Fronczek F. R. and Vicente M. G. H. J. Organom. Chem. 2009, 694: 1607–1611 . Google Scholar
P. C. Martinet al., Inorg. Chem. 30, 3305 (1991), DOI: 10.1021/ic00017a016. Crossref, Web of Science, Google Scholar
N. A. Kuznetsovaet al., J. Porphyrins Phthalocyanines 7, 147 (2003), DOI: 10.1142/S1088424603000203. Link, Web of Science, Google Scholar
a) The Porphyrin Handbook-Phthalocyanines: Properties and Materials, Vol. 17, Kadish K. M., Smith K. M. and Guilard R. (Eds.) Academic Press: New York, 2003. b) Durmus M., Ayhan M. M., Gurek A. G. and Ahsen V. Dyes Pigm. 2008; 77: 570–577. c) Schutte W. J., Sluyters-Rehbach M. and Sluiters J. H. J. Phys. Chem. 1993; 97: 6069–6073. d) Stillman M. J. and Nyokong T. In Phthalocyanines: Properties and Applications, Vol. 1, Leznoff C. C. and Lever A. B. P. (Eds.) VCH Publishers: New York, 1989 . Google Scholar
N. Kobayashiet al., Chem. Eur. J. 9, 5123 (2003), DOI: 10.1002/chem.200304834. Crossref, Web of Science, Google Scholar
A. B. Anderson, T. L. Gorden and M. E. Kenney, J. Am. Chem. Soc. 107, 192 (1985), DOI: 10.1021/ja00287a034. Crossref, Web of Science, Google Scholar
a) Liu J.-Y., Lo P.-C., Fong W.-P. and Ng D. K. P. Org. Biomol. Chem. 2009; 7: 1583–1591. b) Choi C.-F., Huang J.-D., Lo P.-C., Fong W.-P. and Ng D. K. P. Org. Biomol. Chem. 2008; 6: 2173–2181. c) Durmue M. and Nyokong T. Inorg. Chem. Commun. 2007; 10: 332–338. d) Ogunsipe A., Nyokong T. and Durmue M. J. Porphyrins Phthalocyanines 2007; 11: 635–644 . Google Scholar
W. Eberhardt and M. Hanack, Synthesis 95 (1997), DOI: 10.1055/s-1997-1495. Google Scholar
Lyubimtsev A and Hanack M. in preparation . Google Scholar