5 F. Yukruk, A. L. Dogan, H. Canpinar, D. Guc and E. U. Akkaya,
Org. Lett., 2005, 7, 2885–2887.
6 (a) A. Loudet and K. Burgess, Chem. Rev., 2007, 107, 4891–4932;
(b) G. Ulrich, R. Ziessel and A. Harriman, Angew. Chem., Int. Ed.,
2008, 47, 1184–1201.
7 Selected recent examples: (a) S. Badre, V. Monnier, R. Meallet-
Renault, C. Dumas-Verdes, E. Y. Schmidt, A. I. Mikhaleva,
G. Laurent, G. Levi, A. Ibanez, B. A. Trofimov and
R. B. Pansu, J. Photochem. Photobiol., A: Chem., 2006, 183,
238–246; (b) T. Rousseau, A. Cravino, T. Bura, G. Ulrich,
R. Ziessel and J. Roncali, Chem. Commun., 2009, 1673–1675;
(c) X. Qi, S. K. Kim, S. J. Han, L. Xu, A. Y. Jee, H. N. Kim,
C. Lee, Y. Kim, M. Lee, S. J. Kim and J. Yoon, Tetrahedron Lett.,
2008, 49, 261–264.
8 (a) A. Gorman, J. Killoran, C. O’Shea, T. Kenna, W. M. Gallagher
and D. F. O’Shea, J. Am. Chem. Soc., 2004, 126, 10619–10631;
(b) S. O. McDonnel, M. J. Hall, L. T. Allen, A. Byrne,
W. M. Gallagher and D. F. O’Shea, J. Am. Chem. Soc., 2005,
127, 16360–16361; (c) T. Yogo, Y. Urano, Y. Ishitsuka, F. Maniwa
and T. Nagano, J. Am. Chem. Soc., 2005, 127, 12162–12163.
9 D. Pantarotto, J. P. Briant, M. Prato and A. Bianco, Chem.
Commun., 2004, 16–17.
10 (a) N. W. S. Kam, T. C. Jessop, P. A. Wender and H. J. Dai, J. Am.
Chem. Soc., 2004, 126, 6850–6851; (b) N. W. S. Kam, Z. Liu and
H. Dai, Angew. Chem., Int. Ed., 2005, 44, 1–6.
11 K. Kostarelos, L. Lacerda, G. Pastorin, W. Wu, S. Wieckowski,
J. Luangsivilay, S. Godefroy, D. Pantarotto, J. P. Briand,
S. Muller, M. Prato and A. Bianco, Nat. Nanotech., 2007, 2,
108–113.
Fig. 3 Absorbance of DPBF in isopropanol at 411 nm without
compound 1, in the presence of compound 1 only, and in the presence
of compound 1 non-covalently attached to SWNT. Samples were kept
in the dark for the first 15 min and then irradiated at 660 nm for 40 min.
Absorbance was measured at 5 min intervals. Black line: solution
containing DPBF alone; red line: solution containing DPBF (50 mM)
and SWNT-adsorbed compound 1 (62 nM); blue line: solution
containing DPBF (50 mM) and compound 1 without SWNT (62 nM).
When the red LED array was turned on, rapid degradation
started. In just 40 min, the absorbance at 412 nm decreased to
1/5 of the original value. Considering the low concentrations
(62.0 nM and 50.0 mM for the 1–SWNT and the trap
compound, respectively) and low intensity irradiation, this is
quite remarkable. In another experiment, we also showed that
under the experimental conditions of the study, the trap
molecule is not degraded by simple exposure to red light at
660 nm (Fig. 3). In conclusion, our work demonstrates that
SWNTs can be useful delivery agents for photodynamic
therapy. While a small decrease in the singlet oxygen generation
efficiency is observed, that may be a small price to pay
considering the additional benefit of non-covalent modifications
through pyrenyl–SWNT interactions; as various targeting and
signaling moieties can be brought together with equal ease on
the SWNT carrier, resulting in a multifunctional PDT agent.
Our work to that end is in progress.
12 (a) Z. Liu, C. Davis, W. Cai, L. He, X. Chen and H. Dai, Proc.
Natl. Acad. Sci. U. S. A., 2008, 105, 1410–1415; (b) M. L. Schipper,
N. Nakayama-Ratchford, C. R. Davis, N. W. S. Kam, P. Chu,
Z. Liu, X. Sun, H. Dai and S. S. Gambhir, Nat. Nanotech., 2008, 3,
216–221.
13 (a) L. Qu, R. B. Martin, W. Huang, K. Fu, D. Zweifel, Y. Lin,
Y. P. Su, C. E. Bunker, B. A. Harruff, J. R. Gord and L. F. Allard,
J. Chem. Phys., 2002, 117, 8089–8094; (b) A. Hirsch, Angew.
Chem., Int. Ed., 2002, 41, 1853–1859; (c) A. Hirsch and
O. Vostrowski, Top. Curr. Chem., 2005, 245, 193–223; (d) H. Hu,
Y. Ni, S. K. Mandal, V. Montana, B. Zhao, R. C. Haddon and
P. Parpura, J. Phys. Chem. B, 2005, 109, 4285–4289; (e) R. Singh,
D. Pantarotto, D. McCarthy, O. Chaloin, J. Hoebeke,
C. D. Partidos, J. P. Briand, M. Prato, A. Biancho and
A. Kostarelos, J. Am. Chem. Soc., 2005, 127, 4388–4396;
(f) S. Dhar, Z. Liu, J. Thomale, H. Dai and S. J. Lippard,
J. Am. Chem. Soc., 2008, 130, 11467–11476; (g) J. Chen,
S. Chen, X. Zhao, L. V. Kuznetsova, S. S. Wong and I. Ojima,
J. Am. Chem. Soc., 2008, 130, 16778–16785.
14 (a) Z. Liu, M. Winters, M. Holodniy and H. Dai, Angew. Chem.,
Int. Ed., 2007, 46, 2023–2027; (b) N. Shao, S. Lu, E. Wickstrom
and B. Panchapakesan, Nanotechnology, 2007, 18, 315101–315109;
(c) Z. Zhu, Z. Tang, J. A. Phillips, R. Yang, H. Wang and W. Tan,
J. Am. Chem. Soc., 2008, 130, 10856–10857; (d) B. Kang, D. Yu,
S. Chang, D. Chen, Y. Dai and Y. Ding, Nanotechnology, 2008, 19,
375103–375110; (e) H. G. Sudibya, J. Ma, X. Dong, S. Ng, L. J. Li,
X. W. Liu and P. Chen, Angew. Chem., Int. Ed., 2009, 48,
2723–2726.
The authors gratefully acknowledge partial support from
the Turkish Academy of Sciences (TUBA). We also thank
Dr Aykutlu Dana for his help and guidance in the acquisition
of AFM images.
Notes and references
1 R. Bonnet, Chemical Aspects of Photodynamic Therapy, Gordon
and Breach Science, Amsterdam, 2000.
15 R. J. Chen, Y. Zhang, D. Wang and H. Dai, J. Am. Chem. Soc.,
2001, 123, 3838–3839.
2 R. Bonnet and G. Martinez, Tetrahedron, 2001, 57, 9513–9547.
3 (a) R. Waksman, P. E. McEwan, T. I. Moore, R. Pakala,
F. D. Kolodgie, D. G. Hellinga, R. C. Seabron,
S. J. Rychnovsky, J. Vasek, R. W. Scott and R. Virmani, J. Am.
Coll. Cardiol., 2008, 52, 1024–1032; (b) S. G. Rockson, P. Kramer,
M. Razavi, A. Szuba, S. Filardo, P. Fitzgerald, J. P. Cooke,
S. Yousuf, A. R. DeVault, M. F. Renschler and D. C. Adelman,
Circulation, 2000, 102, 2322–2324; (c) M. P. Jenkins,
G. A. Buonaccorsi and M. Raphael, Br. J. Surg., 1999, 86,
1258–1263.
16 W. T. Christian, C. Christensen and M. Meldal, J. Org. Chem.,
2002, 67, 3057–3064.
17 (a) N. Saki, T. Dinc and E. U. Akkaya, Tetrahedron, 2006, 62,
2721–2725; (b) Z. Dost, S. Atilgan and E. U. Akkaya, Tetrahedron,
2006, 62, 8484–8488.
18 H. Zhao, B. Rubio and J. Xia, U.S. Pat., 7 301 003, 2005.
19 Z. Liu, W. Cai, L. He, N. Nakayama, K. Chen and X. Sun, Nat.
Nanotech., 2007, 2, 47–52.
20 T. Ogoshi, Y. Takashima, H. Yamaguchi and A. Harada, J. Am.
Chem. Soc., 2007, 129, 4878–4879.
4 (a) S. Atilgan, Z. Ekmekci, A. L. Dogan, D. Guc and
E. U. Akkaya, Chem. Commun., 2006, 4398–4400; (b) S. Ozlem
and E. U. Akkaya, J. Am. Chem. Soc., 2009, 131, 48–49.
21 F. D’Souza, R. Chitta, A. S. D. Sandanayaka, N. K. Subbaiyan,
L. D’Souza, Y. Araki and O. Ito, J. Am. Chem. Soc., 2007, 129,
15865–15871.
ꢀc
This journal is The Royal Society of Chemistry 2009
4958 | Chem. Commun., 2009, 4956–4958