scholarly journals Two-Photon Photodynamic Therapy by Water-Soluble Self-Assembled Conjugated Porphyrins

2013 ◽  
Vol 2013 ◽  
pp. 1-11 ◽  
Author(s):  
Kazuya Ogawa ◽  
Yoshiaki Kobuke

Studies on two-photon absorption (2PA) photodynamic therapy (PDT) by using three water-soluble porphyrin self-assemblies consisting of ethynylene-linked conjugatedbis(imidazolylporphyrin) are reviewed. 2PA cross-section values in water were obtained by an open aperture Z-scan measurement, and values were extremely large compared with those of monomeric porphyrins such as hematoporphyrin. These compounds were found to generate singlet oxygen efficiently upon one- as well as two-photon absorption as demonstrated by the time-resolved luminescence measurement at the characteristic band of singlet oxygen at 1270 nm and by using its scavenger. Photocytotoxicities for HeLa cancer cells were examined and found to be as high as those of hematoporphyrin, demonstrating that these compounds are potential candidates for 2PA-photodynamic therapy agents.

2007 ◽  
Vol 11 (06) ◽  
pp. 406-417 ◽  
Author(s):  
Yusuke Inaba ◽  
Kazuya Ogawa ◽  
Yoshiaki Kobuke

Acetylene-bridged bisporphyrins and trisporphyrins having branched bulky bis(carboxylethyl)methyl meso-substituents were synthesized. These compounds showed large effective two-photon absorption cross-section values at 890 nm measured by using a nanosecond Z-scan method. Sodium salt of hydrolyzed trisporphyrins showed broad and red-shifted Q-bands over 900 nm. Two-photon absorption cross-section values of water-soluble dimers in water were similar to, or slightly larger than, those of ester forms evaluated in toluene. Furthermore, the generation of singlet oxygen upon one-photon irradiation for dimers in water was confirmed.


2020 ◽  
Vol 11 (9) ◽  
pp. 2494-2503 ◽  
Author(s):  
Zheng Zheng ◽  
Haixiang Liu ◽  
Shaodong Zhai ◽  
Haoke Zhang ◽  
Guogang Shan ◽  
...  

Mitochondria-targeted photosensitizers with highly efficient singlet oxygen generation, bright near-infrared AIE and good two-photon absorption are obtained through ingenious molecular engineering for cancer cell-selective photodynamic therapy.


2019 ◽  
Vol 15 ◽  
pp. 2438-2446 ◽  
Author(s):  
Alessandro Iagatti ◽  
Baihao Shao ◽  
Alberto Credi ◽  
Barbara Ventura ◽  
Ivan Aprahamian ◽  
...  

In this work we apply a combination of steady state and time resolved luminescence and absorption spectroscopies to investigate the excited-state dynamics of a recently developed molecular photoswitch, belonging to the hydrazone family. The outstanding properties of this molecule, involving fluorescence toggling, bistability, high isomerization quantum yield and non-negligible two-photon absorption cross section, make it very promising for numerous applications. Here we show that the light induced Z/E isomerization occurs on a fast <1 ps timescale in both toluene and acetonitrile, while the excited state lifetime of the Z-form depends on solvent polarity, suggesting a partial charge transfer nature of its low lying excited state. Time-resolved luminescence measurements evidence the presence of a main emission component in the 500–520 nm spectral range, attributed to the Z-isomer, and a very short living blue-shifted emission, attributed to the E-isomer. Finally, transient absorption measurements performed upon far-red excitation are employed as an alternative method to determine the two-photon absorption cross-section of the molecule.


2015 ◽  
Vol 19 (09) ◽  
pp. 1046-1052 ◽  
Author(s):  
Ze-Bin Xu ◽  
Fa-Quan Yu ◽  
Fengshou Wu ◽  
Heng Zhang ◽  
Kai Wang ◽  
...  

Through a new synthetic route, three ruthenium-phenanthroline porphyrins (RPP1, RPP2 and RPP3) were prepared. Their photophysical and photochemical properties, such as DNA photocleavage activity, singlet-oxygen photogeneration and two-photon absorption (2PA) were evaluated. These porphyrins 1–3 had substantial photocleavage activities, with 71%, 74% and 38% observed at 20 μM. The porphyrins with different substituents on phenathroline group had similar singlet oxygen quantum yields, with ΦΔ values at 0.52, 0.47 and 0.41, respectively. The 2PA cross-section (σ(2)) values of RPP 1–3, measured by the Z-scan method, were calculated to be 152, 172 and 135 GM, respectively, which were around 5-fold higher than that of H2TPP . Thus, these porphyrins, with their good photocleavage activities, 1 O 2 quantum yields and high 2PA cross section, suggest great potential as photodynamic therapeutic agents.


2005 ◽  
Vol 871 ◽  
Author(s):  
Han Young Woo ◽  
Dmitry Korystov ◽  
Alexander Mikhailovsky ◽  
Guillermo C. Bazan

AbstractA series of tetradonor substituted [2.2]paracyclophane-based two-photon absorption (TPA) fluorophores were designed, synthesized and characterized. Different substituents were chosen to modulate the conjugation and the donor strength and to allow the molecules to be neutral (N series, organic-soluble) or charged (C series, water-soluble). The overall set of compounds series allows us to examine the correlation among the solvent polarity, donor ability of the substituents, and TPA action cross section (ηδd, where δ is the TPA cross section and η is the quantum yield). In water, a significant drop of both δ and η is observed, approximately one-third relative to those in toluene. Weaker donors and/or weaker acceptors with enhanced conjugation are a better choice due to a minimized quenching related to strong charge transfer (CT) upon excitation. One thus needs to fine-tune the magnitude of CT and find an optimal balance among CT,δ and η.


2006 ◽  
Vol 49 (7) ◽  
pp. 2276-2283 ◽  
Author(s):  
Kazuya Ogawa ◽  
Hideki Hasegawa ◽  
Yusuke Inaba ◽  
Yoshiaki Kobuke ◽  
Hideyuki Inouye ◽  
...  

2014 ◽  
Vol 127 (1) ◽  
pp. 171-175 ◽  
Author(s):  
Julie Schmitt ◽  
Valérie Heitz ◽  
Angélique Sour ◽  
Frédéric Bolze ◽  
Hussein Ftouni ◽  
...  

RSC Advances ◽  
2017 ◽  
Vol 7 (32) ◽  
pp. 20068-20075 ◽  
Author(s):  
Qiong Zhang ◽  
Rongting Guan ◽  
Xiaohe Tian ◽  
Lei Luo ◽  
Hongping Zhou ◽  
...  

Two imidazole–pyrimidine hexafluorophosphate derivatives (6P and 10P) are synthesized. The 2PA cross-section values (σ) were obtained by Z-scan and two-photon excited fluorescence methods. 6P and 10P can be used to quantify and image organelles in living cells and tissues.


2016 ◽  
Vol 14 (10) ◽  
pp. 2985-2992 ◽  
Author(s):  
Liqiang Luan ◽  
Wenjuan Fang ◽  
Wei Liu ◽  
Minggang Tian ◽  
Yuxing Ni ◽  
...  

Phthalocyanine-RGD conjugate was synthesized and examined for its two-photon absorption cross section (TPACS), cellular uptake, and photocytotoxicity.


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