Article
Dalton Trans. 2009, 10914–10925. (d) Ruiz, J.; Vicente, C.; de Haro,
C.; Bautista, D. A novel ruthenium(II) arene based intercalator with
potent anticancer activity. Dalton Trans. 2009, 5071–5073.
(11) For a very recent review article about Ru-arene compounds with
Journal of Medicinal Chemistry, 2010, Vol. 53, No. 12 4689
Decesare, M.; Marchesini, R.; Woodburn, K. W.; Reiss, J. A.; Phillips,
D. R.; Zunino, F. Biodistribution of haematoporphyrin analogues in a lung
carcinoma model. Cancer Lett. 1995, 88, 41–48. (c) Woodburn, K. W.;
Phillips, D. R.; Bellinger, G. C. A.; Sadek, M.; Brownlee, R. T. C.; Reiss,
J. A. Synthesis and phototoxicity of a series of haematoporphyrin
analogues. Bioorg. Med. Chem. Lett. 1992, 2, 343–344.
€
anticancer properties see: Suss-Fink, G. Arene ruthenium com-
plexes as anticancer agents. Dalton Trans. 2010, 39, 1673–1688.
(12) Serli, B.; Zangrando, E.; Gianferrara, T.; Scolaro, C.; Dyson, P. J.;
Bergamo, A.; Alessio, E. Is the aromatic fragment of piano-stool
ruthenium compounds an essential feature for anticancer activity?
The development of new Ru(II)-[9]aneS3 analogues. Eur. J. Inorg.
Chem. 2005, 3423–3434.
(13) Bratsos, I.; Jedner, S.; Bergamo, A.; Sava, G.; Gianferrara, T.;
Zangrando, E.; Alessio, E. Half-sandwich RuII-[9]aneS3 complexes
structurally similar to antitumor-active organometallic piano-
stool compounds: preparation, structural characterization and in
vitro cytotoxic activity. J. Inorg. Biochem. 2008, 102, 1120–1133.
(14) (a) Lottner, C.; Bart, K.-C.; Bernhardt, G.; Brunner, H. Hemato-
porphyrin-derived soluble porphyrin-platinum conjugates with
combined cytotoxic and phototoxic antitumor activity. J. Med.
Chem. 2002, 45, 2064–2078. (b) Lottner, C.; Bart, K.-C.; Bernhardt, G.;
Brunner, H. Soluble tetraarylporphyrin-platinum conjugates as
cytotoxic and phototoxic antitumor agents. J. Med. Chem. 2002, 45,
2079–2089.
(15) Mao, J. F.; Zhang, Y. M.; Zhu, J. H.; Zhang, C. L.; Guo, Z. J.
Molecular combo of photodynamic therapeutic agent silicon(IV)
phthalocyanine and anticancer drug cisplatin. Chem. Commun.
2009, 908–910.
(16) (a) Ben-Hur, E.; Chan, W.-S. Phthalocyanines in photobiology and
their medical applications. In The Porphyrin Handbook; Kadish,
K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: Boston, 2003;
Vol. 19, pp 1-35. (b) Pandey, R. K.; Zheng, G. Porphyrins as
photosensitizers in photodynamic therapy. In The Porphyrin Hand-
book; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press:
Boston, 2000; Vol. 6, pp 157-230.
(26) (a) Gullotti, E.; Yeo, Y. Extracellularly activated nanocarriers: a
new paradigm of tumor targeted drug delivery. Mol. Pharmaceutics
2009, 6, 1041–1051. (b) Maeda, H. The enhanced permeability and
retention (EPR) effect in tumor vasculature: the key role of tumor-
selective macromolecular drug targeting. Adv. Enzyme Regul. 2001,
41, 189–207. (c) Baban, D. F.; Seymour, L. W. Control of tumour
vascular permeability. Adv. Drug Delivery Rev. 1998, 34, 109–119.
(27) Gabrielsson, A.; Lindsay Smith, J. R.; Perutz, R. N. Remote site
photosubstitution in metalloporphyrin-rhenium tricarbonylbi-
pyridine assemblies: photoreactions of molecules with very short
lived excited states. Dalton Trans. 2008, 4259–4269.
€
(28) (a) Schmitt, F.; Govindaswamy, P.; Zava, O.; Suss-Fink, G.;
Juillerat-Jeanneret, L.; Therrien, B. Combined arene ruthenium
porphyrins as chemotherapeutics and photosensitizers for cancer
therapy. J. Biol. Inorg. Chem. 2009, 14, 101–109. (b) Schmitt, F.;
Govindaswamy, P.; S€uss-Fink, G.; Han Ang, W.; Dyson, P. J.; Juillerat-
Jeanneret, L.; Therrien, B. Ruthenium porphyrin compounds for
photodynamic therapy of cancer. J. Med. Chem. 2008, 51, 1811–1816.
(29) (a) Rani-Beeram, S.; Meyer, K.; McCrate, A.; Hong, Y.; Nielsen,
M.; Swavey, S. A fluorinated ruthenium porphyrin as a potential
photodynamic therapy agent: synthesis, characterization, DNA
binding, and melanoma cell studies. Inorg. Chem. 2008, 47, 11278–
11283. (b) Davia, K.; King, D.; Hong, Y.; Swavey, S. A porphyr-
in-ruthenium photosensitizer as a potential photodynamic therapy
agent. Inorg. Chem. Commun. 2008, 11, 584–586.
ꢁ
ꢀ
(30) Gianferrara, T.; Bratsos, I.; Iengo, E.; Milani, B.; Ostric, A.;
Spagnul, C.; Zangrando, E.; Alessio, E. Synthetic strategies to-
wards ruthenium-porphyrin conjugates for anticancer activity.
Dalton Trans. 2009, 10742–10756.
(17) Nyman, E. S.; Hynninen, P. H. Research advances in the use of
tetrapyrrolic photosensitizers for photodynamic therapy. J. Photo-
chem. Photobiol., B 2004, 73, 1–28.
(18) Detty, M. R.; Gibson, S. L.; Wagner, S. J. Current clinical and
preclinical photosensitizers for use in photodynamic therapy.
J. Med. Chem. 2004, 47, 3897–3915.
(31) Gianferrara, T.; Giust, D.; Bratsos, I.; Alessio, E. Metalloporphyr-
ins as chemical shift reagents: the unambiguous NMR character-
ization of the cis- and trans-isomers of meso-(bis)-40-pyridyl-(bis)-
40-carboxymethylphenylporphyrins. Tetrahedron 2007, 63, 5006–
5013.
(32) Gianferrara, T.; Serli, B.; Zangrando, E.; Iengo, E.; Alessio, E.
Pyridylporphyrins peripherally coordinated to ruthenium-nitro-
(19) MacDonald, I. J.; Dougherty, T. J. Basic principles of photody-
namic therapy. J. Porphyrins Phthalocyanines 2001, 5, 105–129.
(20) DeRosa, M. C.; Crutchley, R. J. Photosensitized singlet oxygen
and its applications. Coord. Chem. Rev. 2002, 233-234, 351–371.
(21) Weersink, R. A.; Bogaards, A.; Gertner, M.; Davidson, S. R. H.;
Zhang, K.; Netchev, G.; Trachtenberg, J.; Wilson, B. C. Techni-
ques for delivery and monitoring of TOOKAD (WST09)-mediated
photodynamic therapy of the prostate: clinical experience and
practicalities. J. Photochem. Photobiol., B 2005, 79, 211–222.
(22) (a) Farrer, N. J.; Salassa, L.; Sadler, P. J. Photoactivated che-
motherapy (PACT): the potential of excited-state d-block metals in
medicine. Dalton Trans. 2009, 10690–10701. (b) Szacizowski, K.;
Macyk, W.; Drzewiecka-Matuszek, A.; Brindell, M.; Stochel, G.
Bioinorganic photochemistry: frontiers and mechanisms. Chem. Rev.
2005, 105, 2647–2694. (c) Ali, H.; van Lier, J. E. Metal complexes as
photo- and radiosensitizers. Chem. Rev. 1999, 99, 2379–2450.
(23) (a) Song, R.; Kim, Y.-S.; Lee, C. O.; Sohn, Y. S. Synthesis and
antitumor activity of DNA binding cationic porphyrin-platinum-
(II) complexes. Tetrahedron Lett. 2003, 44, 1537–1540. (b) James,
B. R.; Meng, G. G.; Posakony, J. J.; Ravensbergen, J. A.; Ware, C. J.;
Skov, K. A. Porphyrins and metalloporphyrins: potential hypoxic
agents. Met.-Based Drugs 1996, 3, 85–89. (c) Ding, L.; Etemad-
Moghadam, G.; Cros, S.; Auclair, C.; Meunier, B. Syntheses and in
vitro evaluation of water-soluble “cationic metalloporphyrin-
ellipticine” molecules having a high affinity for DNA. J. Med. Chem.
1991, 34, 900–906.
(24) (a) Sun, R. W.-Y.; Che, C.-M. The anti-cancer properties of
gold(III) compounds with dianionic porphyrin and tetradentate
ligands. Coord. Chem. Rev. 2009, 253, 1682–1691. (b) To, Y. F.; Sun,
R. W.-Y.; Chen, Y.; Chan, V. S.-F.; Yu, W.-Y.; Tam, P. K.-H.; Che, C.-
M.; Lin, C.-L. S. Gold(III) porphyrin complex is more potent than
cisplatin in inhibiting growth of nasopharyngeal carcinoma in vitro and
in vivo. Int. J. Cancer. 2009, 124, 1971–1979. (c) Wang, Y.; He, Q.-Y.;
Sun, R. W.-Y.; Che, C.-M.; Chiu, J.-F. Cellular pharmacological
properties of gold(III) porphyrin 1a, a potential anticancer drug lead.
Eur. J. Pharmacol. 2007, 554, 113–122. (d) Wang, Y.; He, Q.-H.; Sun,
R. W.-Y.; Che, C.-M.; Chiu, J.-F. Gold(III) porphyrin 1a induced
apoptosis by mitochondrial death pathways related to reactive oxygen
species. Cancer Res. 2005, 65, 11553–11564.
syls, including the water-soluble Na4[Zn 40TPyP{RuCl4(NO)}4]:
3
synthesis and structural characterization. New J. Chem. 2005, 29,
895–903.
(33) (a) Lauceri, R.; Purrello, R.; Shetty, S. J.; Vicente, M. G. H.
Interactions of anionic carboranylated porphyrins with DNA.
J. Am. Chem. Soc. 2001, 123, 5835–5836. (b) Ribo, J. M.; Crusats,
J.; Farrera, J.-A.; Valero, M. L. Aggregation in water solutions of
tetrasodium diprotonated meso-tetrakis(4-sulfonatophenyl)porphyrin.
J. Chem. Soc., Chem. Commun. 1994, 681–682.
(34) (a) Barrett, A. J.; Kennedy, J. C.; Jones, R. A.; Nadeau, P.; Pottier,
R. H. The effect of tissue and cellular pH on the selective biodis-
tribution of porphyrin-type photochemotherapeutic agents: a
volumetric titration study. J. Photochem. Photobiol., B 1990, 6,
309–323. (b) Cohen, L.; Schwartz, S. Modification of radiosensitivity
by porphyrins: II. Transplanted rhabdomyosarcoma in mice. Cancer
Res. 1966, 26, 1769–1773.
(35) Gianferrara, T.; Bratsos, I.; Alessio, E. A categorization of metal
anticancer compounds based on their mode of action. Dalton
Trans. 2009, 7588–7598.
(36) Ochsner, M. Photophysical and photobiological processes in the
photodynamic therapy of tumours. J. Photochem. Photobiol., B
1997, 39, 1–18.
(37) He, X. Y.; Sikes, R. A.; Thomsen, S.; Chung, L. W.; Jacques, S. L.
Photodynamic therapy with photofrin II induces programmed
cell death in carcinoma cell lines. Photochem. Photobiol. 1994, 59,
468–473.
(38) Dahle, J.; Steen, H. B.; Moan, J. The mode of cell death induced by
photodynamic treatment depends on cell density. Photochem.
Photobiol. 1999, 70, 363–367.
(39) (a) Luo, Y.; Chang, C. K. Initiation of apoptosis versus necrosis by
photodynamic therapy. Photochem. Photobiol. 1996, 66, 479–483.
(b) Bugelsky, P. J.; Porter, C. W.; Dougherty, T. J. Autoradiographic
distribution of hematoporphyrin derivate in normal and tumour tissue of
the mouse. Cancer Res. 1981, 41, 4606–4612.
(40) (a) Klein, A. V.; Hambley, T. W. Platinum drug distribution in
cancer cells and tumors. Chem. Rev. 2009, 109, 4911–4920. (b) Kapp,
T.; Dullin, A.; Gust, R. Mono- and polynuclear [alkylamine]plati-
num(II) complexes of [1,2-bis(4-fluorophenyl)ethylenediamine]plati-
num(II): synthesis and investigations on cytotoxicity, cellular distri-
bution, and DNA and protein binding. J. Med. Chem. 2006, 49,
(25) (a) Vicente, M. G. H. Porphyrin-based sensitizers in the detection
and treatment of cancer: recent progress. Curr. Med. Chem. Antic-
ancer Agents 2001, 1, 175–194. (b) Tronconi, W.; Colombo, A.;