466
K. Imato and Y. Ooyama
Pal P, Zeng H, Durocher G, Girard D, Li T, Gupta AK, Giasson R, Blanchard L, Gaboury
L, Balassy A, Turmel C, Laperrière A, Villeneuve L (1996) Phototoxicity of some brominesubstituted rhodamine dyes: synthesis, photophysical properties and application as photosensitizers. Photochem Photobiol 63:161–168. https://doi.org/10.1111/j.1751-1097.1996.tb03008.x
Patrice T (2003) Photodynamic therapy. Royal Society of Chemistry, London
Pawlicki M, Collins HA, Denning RG, Anderson HL (2009) Two-photon absorption and the design
of two-photon dyes. Angew Chem Int Ed 48:3244–3266. https://doi.org/10.1002/anie.200805257
Prein M, Adam W (1996) The Schenck ene reaction: diastereoselective oxyfunctionalization with
singlet oxygen in synthetic applications. Angew Chem Int Ed 35:477–494. https://doi.org/10.
1002/anie.199604771
Ramaiah D, Joy A, Chandrasekhar N, Eldho NV, Das S, George MV (1997) Halogenated squaraine
dyes as potential photochemotherapeutic agents: synthesis and study of photophysical properties
and quantum efficiencies of singlet oxygen generation. Photochem Photobiol 65:783–790. https://
doi.org/10.1111/j.1751-1097.1997.tb01925.x
Redmond RW, Gamlin JN (1999) A compilation of singlet oxygen yields from biologically relevant molecules. Photochem Photobiol 70:391–475. https://doi.org/10.1111/j.1751-1097.1999.tb0
8240.x
Ronzani F, Trivella A, Arzoumanian E, Blanc S, Sarakha M, Richard C, Oliveros E, Lacombe S
(2013) Comparison of the photophysical properties of three phenothiazine derivatives: transient
detection and singlet oxygen production. Photochem Photobiol Sci 12:2160–2169. https://doi.
org/10.1039/c3pp50246e
Rubio N, Prat F, Bou N, Borrell JI, Teixidó J, Villanueva Á, Juarranz Á, Cañete M, Stockert JC,
Nonell S (2005) A comparison between the photophysical and photosensitising properties of
tetraphenyl porphycenes and porphyrins. New J Chem 29:378–384. https://doi.org/10.1039/B41
5314F
Salice P, Arnbjerg J, Pedersen BW, Toftegaard R, Beverina L, Pagani GA, Ogilby PR (2010)
Photophysics of squaraine dyes: role of charge-transfer in singlet oxygen production and removal.
J Phys Chem a 114:2518–2525. https://doi.org/10.1021/jp911180n
Schmitt J, Heitz V, Sour A, Bolze F, Ftouni H, Nicoud J-F, Flamigni L, Ventura B (2015)
Diketopyrrolopyrrole-porphyrin conjugates with high two-photon absorption and singlet oxygen
generation for two-photon photodynamic therapy. Angew Chem Int Ed 54:169–173. https://doi.
org/10.1002/anie.201407537
Shimakoshi H, Baba T, Iseki Y, Aritome I, Endo A, Adachi C, Hisaeda Y (2008) Photophysical and
photosensitizing properties of brominated porphycenes. Chem Commun 25:2882–2884. https://
doi.org/10.1039/b802730g
Shinmori H, Kodaira F, Matsugo S, Kawabata S, Osuka A (2005) Photosensitizing properties of
diazaporphyrin derivatives for singlet oxygen generation. Chem Lett 34:322–323. https://doi.org/
10.1246/cl.2005.322
Stacey OJ, Pope SJA (2013) New avenues in the design and potential application of metal complexes
for photodynamic therapy. RSC Adv 3:25550–25564. https://doi.org/10.1039/c3ra45219k
Takizawa S-Y, Aboshi R, Murata S (2011) Photooxidation of 1,5-dihydroxynaphthalene with iridium
complexes as singlet oxygen sensitizers. Photochem Photobiol Sci 10:895–903. https://doi.org/
10.1039/c0pp00265h
Tian J, Ding L, Xu H-J, Shen Z, Ju H, Jia L, Bao L, Yu J-S (2013) Cell-specific and pH-activatable
rubyrin-loaded nanoparticles for highly selective near-infrared photodynamic therapy against
cancer. J Am Chem Soc 135:18850–18858. https://doi.org/10.1021/ja408286k
Watley RL, Awuah SG, Bio M, Cantu R, Gobeze HB, Nesterov VN, Das SK, D’Souza F, You
Y (2015) Dual functioning thieno-pyrrole fused BODIPY dyes for NIR optical imaging and
photodynamic therapy: singlet oxygen generation without heavy halogen atom assistance. Chem
Asian J 10:1335–1343. https://doi.org/10.1002/asia.201500140
Yamakoshi Y, Umezawa N, Ryu A, Arakane K, Miyata N, Goda Y, Masumizu T, Nagano T (2003)
Active oxygen species generated from photoexcited fullerene (C60) as potential medicines: O2-•
versus 1O2. J Am Chem Soc 125:12803–12809. https://doi.org/10.1021/ja0355574
K. Imato and Y. Ooyama
Pal P, Zeng H, Durocher G, Girard D, Li T, Gupta AK, Giasson R, Blanchard L, Gaboury
L, Balassy A, Turmel C, Laperrière A, Villeneuve L (1996) Phototoxicity of some brominesubstituted rhodamine dyes: synthesis, photophysical properties and application as photosensitizers. Photochem Photobiol 63:161–168. https://doi.org/10.1111/j.1751-1097.1996.tb03008.x
Patrice T (2003) Photodynamic therapy. Royal Society of Chemistry, London
Pawlicki M, Collins HA, Denning RG, Anderson HL (2009) Two-photon absorption and the design
of two-photon dyes. Angew Chem Int Ed 48:3244–3266. https://doi.org/10.1002/anie.200805257
Prein M, Adam W (1996) The Schenck ene reaction: diastereoselective oxyfunctionalization with
singlet oxygen in synthetic applications. Angew Chem Int Ed 35:477–494. https://doi.org/10.
1002/anie.199604771
Ramaiah D, Joy A, Chandrasekhar N, Eldho NV, Das S, George MV (1997) Halogenated squaraine
dyes as potential photochemotherapeutic agents: synthesis and study of photophysical properties
and quantum efficiencies of singlet oxygen generation. Photochem Photobiol 65:783–790. https://
doi.org/10.1111/j.1751-1097.1997.tb01925.x
Redmond RW, Gamlin JN (1999) A compilation of singlet oxygen yields from biologically relevant molecules. Photochem Photobiol 70:391–475. https://doi.org/10.1111/j.1751-1097.1999.tb0
8240.x
Ronzani F, Trivella A, Arzoumanian E, Blanc S, Sarakha M, Richard C, Oliveros E, Lacombe S
(2013) Comparison of the photophysical properties of three phenothiazine derivatives: transient
detection and singlet oxygen production. Photochem Photobiol Sci 12:2160–2169. https://doi.
org/10.1039/c3pp50246e
Rubio N, Prat F, Bou N, Borrell JI, Teixidó J, Villanueva Á, Juarranz Á, Cañete M, Stockert JC,
Nonell S (2005) A comparison between the photophysical and photosensitising properties of
tetraphenyl porphycenes and porphyrins. New J Chem 29:378–384. https://doi.org/10.1039/B41
5314F
Salice P, Arnbjerg J, Pedersen BW, Toftegaard R, Beverina L, Pagani GA, Ogilby PR (2010)
Photophysics of squaraine dyes: role of charge-transfer in singlet oxygen production and removal.
J Phys Chem a 114:2518–2525. https://doi.org/10.1021/jp911180n
Schmitt J, Heitz V, Sour A, Bolze F, Ftouni H, Nicoud J-F, Flamigni L, Ventura B (2015)
Diketopyrrolopyrrole-porphyrin conjugates with high two-photon absorption and singlet oxygen
generation for two-photon photodynamic therapy. Angew Chem Int Ed 54:169–173. https://doi.
org/10.1002/anie.201407537
Shimakoshi H, Baba T, Iseki Y, Aritome I, Endo A, Adachi C, Hisaeda Y (2008) Photophysical and
photosensitizing properties of brominated porphycenes. Chem Commun 25:2882–2884. https://
doi.org/10.1039/b802730g
Shinmori H, Kodaira F, Matsugo S, Kawabata S, Osuka A (2005) Photosensitizing properties of
diazaporphyrin derivatives for singlet oxygen generation. Chem Lett 34:322–323. https://doi.org/
10.1246/cl.2005.322
Stacey OJ, Pope SJA (2013) New avenues in the design and potential application of metal complexes
for photodynamic therapy. RSC Adv 3:25550–25564. https://doi.org/10.1039/c3ra45219k
Takizawa S-Y, Aboshi R, Murata S (2011) Photooxidation of 1,5-dihydroxynaphthalene with iridium
complexes as singlet oxygen sensitizers. Photochem Photobiol Sci 10:895–903. https://doi.org/
10.1039/c0pp00265h
Tian J, Ding L, Xu H-J, Shen Z, Ju H, Jia L, Bao L, Yu J-S (2013) Cell-specific and pH-activatable
rubyrin-loaded nanoparticles for highly selective near-infrared photodynamic therapy against
cancer. J Am Chem Soc 135:18850–18858. https://doi.org/10.1021/ja408286k
Watley RL, Awuah SG, Bio M, Cantu R, Gobeze HB, Nesterov VN, Das SK, D’Souza F, You
Y (2015) Dual functioning thieno-pyrrole fused BODIPY dyes for NIR optical imaging and
photodynamic therapy: singlet oxygen generation without heavy halogen atom assistance. Chem
Asian J 10:1335–1343. https://doi.org/10.1002/asia.201500140
Yamakoshi Y, Umezawa N, Ryu A, Arakane K, Miyata N, Goda Y, Masumizu T, Nagano T (2003)
Active oxygen species generated from photoexcited fullerene (C60) as potential medicines: O2-•
versus 1O2. J Am Chem Soc 125:12803–12809. https://doi.org/10.1021/ja0355574