Abstract
A series of phthalocyanine-peptide-quencher conjugates (6-9) were synthesized as photosensitizers for photodynamic therapy in cancer treatment. The photophysical, photochemical and photobiological properties of these activatable molecular beacons were also investigated in this study. For this purpose, the fluorescence, singlet oxygen and photodegradation quantum yields and fluorescence lifetime values of the compounds were determined in DMSO solutions. The phototoxicity and cytotoxicity of the systems were studied against the cervical cancer cell line named HeLa for an evaluation of their suitability for photodynamic therapy. The results showed that a maximum of 80% of HeLa cells were killed following light irradiation with photodynamic efficiency. All of the results showed that the novel activatable molecular beacons could be suitable candidates for cancer treatment via PDT technique.
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M. R. Detty, S. L. Gibson and S. J. Wagner, J. Med. Chem., 2004, 47, 3897–3915.
B. Turk, Nat. Rev., 2006, 5, 785–799.
B. Law and C. Tung, Bioconjugate Chem., 2009, 20, 1683–1695.
M. Cicek and M. J. Oursler, Cancer Metastasis Rev., 2006, 25, 635–644.
R. L. Scherer, J. O. Mc Intyre and L. M. Matrisian, Cancer Metastasis Rev., 2008, 27, 679–690.
T. W. Liu, J. Chen and G. Zheng, Amino Acids, 2011, 41(2), 1123–1134.
C. E. Brinckerhoff and L. M. Matrisian, Nat. Rev. Mol. Cell Biol., 2002, 3, 207–214.
T. A. Guise, Genes Dev., 2009, 23, 2117–2123.
M. Ii, H. Yamamoto, Y. Adachi, Y. Maruyama and Y. Shinomura, Exp. Biol. Med., 2006, 231, 20–27.
K. Kessenbrock, V. Plaks and Z. Werb, Cell, 2010, 141, 52–67.
C. H. Tung, Biopolymers, 2004, 76, 391–403.
T. Jiang, E. S. Olson, Q. T. Nguyen, M. Roy, P. A. Jennings and R. Y. Tsien, Proc. Natl. Acad. Sci. U. S. A., 2004, 101, 17867–17872.
E. A. Goun, R. Shinde, K. W. Dehnert, A. Adams-Bond, P. A. Wender, C. H. Contag and B. L. Franc, Bioconjugate Chem., 2006, 17, 787–796.
G. Blum, S. R. Mullins, K. Keren, M. Fonovic, C. Jedeszko, M. J. Rice, B. F. Sloane and M. Bogyo, Nat. Chem. Biol., 2005, 1, 203–209.
D. Kato, K. M. Boatright, A. B. Berger, T. Nazif, G. Blum, C. Ryan, K. A. Chehade, G. S. Salvesen and M. Bogyo, Nat. Chem. Biol., 2005, 1, 33–38.
G. Blum, G. von Degenfeld, M. J. Merchant, H. M. Blau and M. Bogyo, Nat. Chem. Biol., 2007, 3, 668–677.
M. Verhille, H. Benachour, A. Ibrahim, M. Achard, P. Arnoux, M. Barberi-Heyob, J. C. Andre, X. Allonas, F. Baros, R. Vanderesse and C. Frochot, Curr. Med. Chem., 2012, 19, 5580–5594.
M. Verhille, P. Couleaud, R. Vanderesse, D. Brault, M. Barberi-Heyob and C. Frochot, Curr. Med. Chem., 2010, 17, 3925–3943.
J. Chen, K. Stefflova, M. J. Niedre, B. C. Wilson, B. Chance, J. D. Glickson and G. Zheng, J. Am. Chem. Soc., 2004, 126(37), 11450–11451.
G. Zheng, J. Chen, K. Stefflova, M. Jarvi, H. Li and B. C. Wilson, Proc. Natl. Acad. Sci. U. S. A., 2007, 104(21), 8989–8994.
J. Chen, K. Stefflova, M. Warren, J. Bu, B. C. Wilson and G. Zheng, Proc. SPIE-Int. Soc. Opt. Eng., 2007, 6449, 1–9, (Genetically Engineered and Optical Probes for Biomedical Applications IV).
P. Lo, J. Chen, K. Stefflova, M. S. Warren, R. Navab, B. Bandarchi, S. Mullins, M. Tsao, J. D. Cheng and G. Zheng, J. Med. Chem., 2009, 52(2), 358–368.
J. F. Lovell, T. W. B. Liu, J. Chen and G. Zheng, Chem. Rev., 2010, 110, 2839–2857.
S. Lee, K. Park, K. Kim, K. Choi and I. C. Kwon, Chem. Commun., 2008, 4250–4260.
B. Ballou, et al., Cancer Immunol. Immunother., 1995, 41, 257–263.
K. Licha, et al., Photochem. Photobiol., 2000, 72, 392–398.
A. Becker, et al., Photochem. Photobiol., 2000, 72, 234–241.
R. Weissleder, C. H. Tung, U. Mahmood, A. Bogdanov Jr., Nat. Biotechnol., 1999, 17, 375–378.
A. Becker, C. Hessenius, K. Licha, B. Ebert, U. Sukowski, W. Semmler, B. Wiedenmann, C. Grötzinger, Nat. Biotechnol., 2001, 19, 327–331.
M. Göksel, M. Durmuş and D. Atilla, J. Photochem. Photobiol., A, 2013, 266, 37–46.
M. Sibrian-Vazquez, J. Ortiz, I. V. Nesterova, F. Fernandez-Lazaro, A. Sastre-Santos, S. A. Soper and M. G. H. Vicente, Bioconjugate Chem., 2007, 18, 410–420.
R. B. Merrifield, J. Am. Chem. Soc., 1963, 85(14), 2149–2154.
M. J. Stillman and T. Nyokong, in Phthalocyanines: Properties and Applications, ed. C. C. Leznoff and A. B. P. Lever, VCH Publishers, New York, 1989, vol. 1, ch. 3.
I. Gürol, M. Durmuş, V. Ahsen and T. Nyokong, Dalton Trans., 2007, 34, 3782–3791.
J. F. Lovell, J. Chen, M. T. Jarvi, W. Cao, A. D. Allen, Y. Liu, T. T. Tidwell, B. C. Wilson and G. Zheng, J. Phys. Chem. B, 2009, 113, 3203–3211.
M. Durmuş, Photochemical and photophysical characterization, in Photosensitizers in Medicine, Environment, and Security, ed. T. Nyokong and V. Ahsen, Springer, New York, 2012, pp. 135–267.
T. Nyokong, Coord. Chem. Rev., 2007, 251, 1707–1722.
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Göksel, M., Durmuş, M. & Atilla, D. Peptide-substituted phthalocyanine photosensitizers: design, synthesis, photophysicochemical and photobiological studies. Photochem Photobiol Sci 15, 1318–1329 (2016). https://doi.org/10.1039/c6pp00231e
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DOI: https://doi.org/10.1039/c6pp00231e