ArticlesNo Access

Dendrimeric-like hexadecahydroxylated zinc phthalocyanine: Synthesis and evaluation of photodynamic efficiency

Serkan Alpugan

Gebze Institute of Technology, Department of Chemistry, P.O. Box 141, Gebze, 41400 Kocaeli, Turkey

Search for more papers by this author

Guillaume Garcia

Institut Curie, Section de Recherche, Bât 110-112, Centre Universitaire, F-91405 Orsay, France

UMR 176 CNRS, Bât 110, Centre Universitaire, F-91405 Orsay, France

Université Paris-Sud, Centre Universitaire, F-91405 Orsay, France

CNRS GDR 3049 PHOTOMED, UMR 5623 Université Paul Sabatier, F-31062 Toulouse Cedex 9, France

Search for more papers by this author

Florent Poyer

Institut Curie, Section de Recherche, Bât 110-112, Centre Universitaire, F-91405 Orsay, France

Université Paris-Sud, Centre Universitaire, F-91405 Orsay, France

CNRS GDR 3049 PHOTOMED, UMR 5623 Université Paul Sabatier, F-31062 Toulouse Cedex 9, France

U759 INSERM, Bât 112, Centre Universitaire, F-91405 Orsay, France

Search for more papers by this author

Mahmut Durmuş

Gebze Institute of Technology, Department of Chemistry, P.O. Box 141, Gebze, 41400 Kocaeli, Turkey

Search for more papers by this author

Philippe Maillard

Institut Curie, Section de Recherche, Bât 110-112, Centre Universitaire, F-91405 Orsay, France

UMR 176 CNRS, Bât 110, Centre Universitaire, F-91405 Orsay, France

Université Paris-Sud, Centre Universitaire, F-91405 Orsay, France

CNRS GDR 3049 PHOTOMED, UMR 5623 Université Paul Sabatier, F-31062 Toulouse Cedex 9, France

SPP full member in good standing.

Search for more papers by this author

Vefa Ahsen

Gebze Institute of Technology, Department of Chemistry, P.O. Box 141, Gebze, 41400 Kocaeli, Turkey

SPP full member in good standing.

Search for more papers by this author

, and

Fabienne Dumoulin

Gebze Institute of Technology, Department of Chemistry, P.O. Box 141, Gebze, 41400 Kocaeli, Turkey

Corresponding author, fax: +90 262-605-3101, tel: +90 262-605-3106.

SPP full member in good standing.

Search for more papers by this author

https://doi.org/10.1142/S1088424613500508Cited by:6 (Source: Crossref)

Abstract

The design of a dendrimeric-like diglycerol-tetrasubstituted Zn(II) phthalocyanine resulted in a remarkably water-soluble compound due to the presence of 16 hydroxyls. Several parameters relevant to evaluate the photodynamic efficiency of a potentiel photosensitizer such as: aggregation behavior, fluorescence properties, singlet oxygen generation, binding to a carrier protein model (Bovine Serum Albumin) and partition coefficient have been measured. Biocompatibility was demonstrated by dark cytotoxicity in in vitro experiments. The absence of phototoxicity can be explained by an elevated hydrophilicity. All the collected data have confirmed that this new substitution pattern is promising to be used on phthalocyanines aiming at being photodynamic therapy agents.

Dedicated to Professor Özer Bekaroğlu on the occasion of his 80th birthday

Keywords:

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

References

R. W. Boyle and D. Dolphin , Photochem. Photobiol. 64 , 469 ( 1996 ) . Crossref, Web of Science, Google Scholar
L. B. Josefsen and R. W. Boyle , Metal-Based Drugs ( 2008 ) . Google Scholar
T. J. Kinsella et al. , Front. Oncol. 1 , 1 ( 2011 ) . Google Scholar
V. V. Sokolovet al., Proceedings of The Society of Photo-Optical Instrumentation Engineers (SPIE)2625, eds. B. Ehrenberget al. (1996) pp. 281–287. Google Scholar
F. Dumoulin et al. , Coord. Chem. Rev. 254 , 2792 ( 2010 ) . Crossref, Web of Science, Google Scholar
a) Zorlu Y, Ermeydan MA, Dumoulin F, Ahsen V, Savoie H and Boyle RW. Photochem. Photobiol. Sci. 2008; 8: 312–318. b) Güzel E, Atsay A, NalbantoÈlu S, şaki N, DoÈan AL, Gül A and Burkut K.cak M. Dyes Pig. 2013; 97: 238–243. c) Zorlu Y, Ün and Dumoulin F. J. Porphyrins Phthalocyanines 2009; 13: 760–768. d) Allen CM, Sharman WM and Van L.er JE. J. Porphyrins Phthalocyanines 2001; 5: 161–169. e) Zorlu Y, Dumoulin F, Bouchu D, Ahsen V and Lafont D. Tetrahedron Lett. 2010; 51: 6615–6618. (e) Dumoulin F, Ali H, Ahsen V and van L.er JE. Tetrahedron Lett. 2011; 52: 4395–4397 . Google Scholar
M. Durmuê , C. Lebrun and V. Ahsen , J. Porphyrins Phthalocyanines 8 , 1175 ( 2004 ) . Link, Web of Science, Google Scholar
Noiret N, Rivaux Y, Brochette P, Algarra L and Patin H. J. Surfact. Deterg. 1999; 2: 349–355. (b) Kawagishi T, Yoshikawa K, Ubukata M, Hamada M and Nakajima N. Heterocycles 2006; 69: 107–111 . Google Scholar
C. A. Lipinski et al. , Adv. Drug Deliv. Rev. 23 , 3 ( 1997 ) . Crossref, Web of Science, Google Scholar
a) Lv F, He X, Wu L and Liu T. Bioorg. Med. Chem. Lett. 2013; http://dx.doi.org/10.1016/j.bmcl. 2012.12.103. b) Lv F, He X, Lu I, Wu L and Liu T. J. Porphyrins Phthalocyanines 2012; 16: 77–84 . Google Scholar
a) Gürol, Durmuê M, Ahsen V and Nyokong T. Dalton Trans. 2007; 34: 3782–3791. b) Ogunsipe A, Chen J-Y and Nyokong T. New J. Chem. 2004; 28: 822–827 . Google Scholar
N. Kuznetsova et al. , Russ. J. Gen. Chem. 70 , 133 ( 2000 ) . Web of Science, Google Scholar
a) Jiang CQ, Gao MX and He JX. Anal. Chim. Acta 2002; 452: 185–189. b) Gou M, Zou JW, Yi PG, Shang ZC, Hu GX and Yu QS. Anal. Sci. 2004; 20: 465–470 . Google Scholar
S. L. Murov , I. Carmichael and G. L. Hug , Handbook of Photochemistry , 2nd edn. ( M. Decker , New York , 1993 ) . Google Scholar
a) Nunes SMT, Sguilla FS and Tedesco AC. Braz. J. Med. Biol. Res. 2004; 37: 273–284. b) Uslan C, Sesalan BŞ and Durmuş M. J. Photochem. Photobiol. A: Chem. 2012; 235: 56–64. c) Bıyıklıǧlu Z, Durmuş M and Kantekin H. J. Photochem. Photobiol. A: Chem. 2011; 222: 87–96 . Google Scholar
J. G. Young and W. J. Onyebuagu , Org. Chem. 55 , 2155 ( 1990 ) . Crossref, Web of Science, Google Scholar
D. D. Perrin and W. L. F. Armarego , Purification of Laboratory Chemicals , 2nd edn. ( Pergamon Press , Oxford , 1989 ) . Google Scholar