Taurine-modified Ru(ii)-complex targets cancerous brain cells for photodynamic therapy

2017 ◽  
Vol 53 (44) ◽  
pp. 6033-6036 ◽  
Author(s):  
Enming Du ◽  
Xunwu Hu ◽  
Sona Roy ◽  
Peng Wang ◽  
Kieran Deasy ◽  
...  
Keyword(s):  
Photodynamic Therapy ◽  
Quantum Yield ◽  
Cancer Cells ◽  
Water Solubility ◽  
Brain Cells ◽  
Independent Manner ◽  
Ru Complex

Symmetrical taurine modification not only enhances the intracellular affinity of a polypyridyl Ru-complex to cancer cells, but also boosts the quantum yield in a pH-independent manner without sacrificing water solubility for cytosolic photosensitizers of photodynamic therapy, with prominent efficacy in cancerous brain cells.

scholarly journals Evaluation of Polyhedral Oligomeric Silsesquioxane Porphyrin Derivatives on Photodynamic Therapy

Molecules ◽  
2020 ◽  
Vol 25 (21) ◽  
pp. 4965
Author(s):  
Paolo Siano ◽  
Alexis Johnston ◽  
Paula Loman-Cortes ◽  
Zaneta Zhin ◽  
Juan L. Vivero-Escoto
Keyword(s):  
Photodynamic Therapy ◽  
Quantum Yield ◽  
Singlet Oxygen ◽  
Cancer Cells ◽  
Functional Groups ◽  
Steric Hindrance ◽  
Polyhedral Oligomeric Silsesquioxane ◽  
Porphyrin Derivatives ◽  
And Performance ◽  
Oligomeric Silsesquioxane

Polyhedral oligomeric silsesquioxane (POSS) is a promising scaffold to be used as delivery system. POSS can modify the properties of photosensitizers to enhance their efficacy toward photodynamic therapy (PDT). In this work, we designed, synthesized and characterized five different POSS porphyrin (POSSPs 1–5) derivatives containing hydrophobic (1–3) and hydrophilic (4 and 5) functional groups. In general, all the POSSPs showed a better singlet oxygen quantum yield than the parent porphyrins due to the steric hindrance from the POSS unique structure. POSSPs 1 and 3 containing isobutyl groups showed better PDT performance in cancer cells at lower concentrations than POSSPs 4 and 5. However; at higher concentrations, the POSSP4 containing hydrophilic groups has an enhanced PDT efficiency as compared with the parent porphyrin. We envision that the chemical tunability of POSSs can be used as a promising option to improve the delivery and performance of photosensitizers.

Effect of PVP formulation on the in vitro photodynamic efficiency of a photosensitizing phthalocyanine

2019 ◽  
Vol 23 (11n12) ◽  
pp. 1587-1591
Author(s):  
Eda Gazel Pehlivan ◽  
Yıldız Ek ◽  
Derya Topkaya ◽  
Uygar Halis Tazebay ◽  
Fabienne Dumoulin
Keyword(s):  
Photodynamic Therapy ◽  
Cancer Cells ◽  
Water Solubility ◽  
Human Cancer ◽  
Food Additive ◽  
Human Cancer Cells ◽  
Classical Formulation ◽  
Therapy Treatment

The administration of photosensitizers and their biocompatibility is crucial to the success of photodynamic therapy treatment. Amongst the various strategies developed to administer photosensitizers of low water-solubility, the use of polyvinylpyrrolidone (PVP), an FDA-approved food additive, is emerging as extremely promising. Its effect on photodynamic outcome was compared to more classical formulation in DMSO and direct solubilization in water. The tetrakis (2-(2-(2-methoxyethoxy)ethoxy)ethoxy)-Zn(II) phthalocyanine chosen as the model photosensitizer for this study proved to be a powerful photosensitizer. Even if slightly less efficient than DMSO formulation, PVP formulation proved to work very well, with submicromolar IC50 and IC90 values against MDA-MB-231 human cancer cells.

Biotinylated-cationic zinc(II) phthalocyanine towards photodynamic therapy

2019 ◽  
Vol 23 (01n02) ◽  
pp. 46-55 ◽  
Author(s):  
Basma Ghazal ◽  
Esra Nur Kaya ◽  
Ali Husain ◽  
Asaithampi Ganesan ◽  
Mahmut Durmuş ◽  
...  
Keyword(s):  
Photodynamic Therapy ◽  
Cancer Treatment ◽  
Cancer Cells ◽  
Elemental Analysis ◽  
Water Solubility ◽  
Spectroscopic Techniques ◽  
Ft Ir ◽  
Photochemical Properties ◽  
Pharmaceutical Properties ◽  
C Nmr

Targeting biotin receptors in cancer cells can improve specifying of photosensitizers (PSs) for cancer treatment by photodynamic therapy (PDT) applications. Consequently, there has been extensive research focusing mainly on the design of PSs with optimized pharmaceutical properties and better targeting toward cancer cells. Herein a tailored mono-biotinylated zinc(II) phthalocyanine (Pc-1) substituted with six phenoxy-bis(triazolyl) substituents has been synthesized. This Pc-1 has been further modified to its cationic version (Pc-2) through quaternizing of the triazole moiety to gain water solubility. Both non-ionic zinc(II) phthalocyanine (Pc-1) and its cationic derivative (Pc-2) were characterized by standard spectroscopic techniques, namely; FT-IR, 1H and [Formula: see text]C NMR, UV-Vis and MALDI-TOF, and by elemental analysis. The photophysical and photochemical properties were evaluated in DMSO for the non-ionic Pc-1 and in both DMSO and water for the cationic Pc-2.

Cyclometalated iridium(iii) complex nanoparticles for mitochondria-targeted photodynamic therapy

Nanoscale ◽  
2020 ◽  
Vol 12 (26) ◽  
pp. 14061-14067 ◽  
Author(s):  
Huan Lu ◽  
Xinpeng Jiang ◽  
Yanyan Chen ◽  
Ke Peng ◽  
Yiming Huang ◽  
...  
Keyword(s):  
Breast Cancer ◽  
Photodynamic Therapy ◽  
Cancer Cells ◽  
White Light ◽  
Breast Cancer Cells ◽  
Water Solubility ◽  
Targeting Ability ◽  
Targeted Photodynamic Therapy ◽  
Mitochondria Targeting ◽  
Mcf 7

Ir(tiq)2ppy nanoparticles are prepared to achieve water solubility and mitochondria-targeting ability with high PDT efficiency to MCF-7 breast cancer cells under white light irradiation.

Synthesis and Characterization of ROSA Dye - A Rhodamine B-type Fluorophore, Suitable for Bioconjugation and Fluorescence Studies in Live Cells

2019 ◽  
Vol 26 (10) ◽  
pp. 758-767
Author(s):  
Vicente Rubio ◽  
Vijaya Iragavarapu ◽  
Maciej J. Stawikowski
Keyword(s):  
Quantum Yield ◽  
Cancer Cells ◽  
Fluorescent Probe ◽  
Extinction Coefficient ◽  
Rhodamine B ◽  
Solid Phase ◽  
Total Yield ◽  
Molar Extinction Coefficient ◽  
Αvβ3 Integrin ◽  
Αvβ3 Integrins

Background: Herein we report the multigram-scale synthesis, characterization and application of a rhodamine B-based fluorophore (ROSA) suitable for fluorescent studies in biological applications. This fluorophore is devoid of rhodamine spirolactone formation and furthermore characterized by a high molar extinction coefficient (ϵ=87250 ± 1630 M-1cm-1) and quantum yield (φ) of 0.589 ± 0.070 in water. Reported here is also the application of ROSA towards synthesis of a ROSA-PEG-GRGDS-NH2 fluorescent probe suitable for live cell imaging of αvβ3 integrins for in vitro assays. Objective: The main objective of this study is to efficiently prepare rhodamine B derivative, devoid of spirolactone formation that would be suitable for bioconjugation and subsequent bioimaging. Methods: Rhodamine B was transformed into rhodamine B succinimide ester (RhoB-OSu) using N-hydroxysuccinimide. RhoB-OSu was further coupled to sarcosine to obtain rhodamine Bsarcosine dye (ROSA) in good yield. The ROSA dye was then coupled to a αvβ3 integrin binding sequence using standard solid-phase conditions. Resulting ROSA-PEG-GRGDS-NH2 probe was used to image integrins on cancer cells. Results: The rhodamine B-sarcosine dye (ROSA) was obtained in multigram scale in good total yield of 47%. Unlike rhodamine B, the ROSA dye does not undergo pH-dependent spirolactone/spirolactam formation as compared with rhodamine B-glycine. It is also characterized by excellent quantum yield (φ) of 0.589 ± 0.070 in water and high molar extinction coefficient of 87250 ± 1630 M-1cm-1. ROSA coupling to the RGD-like peptide was proved to be efficient and straightforward. Imaging using standard filters on multimode plate reader and confocal microscope was performed. The αvβ3 integrins present on the surface of live WM-266-4 (melanoma) and MCF- 7 (breast cancer) cells were successfully imaged. Conclusion: We successfully derivatized rhodamine B to create an inexpensive, stable and convenient to use fluorescent probe. The obtained derivative has excellent photochemical properties and it is suitable for bioconjugation and many imaging applications.

scholarly journals Use of Half-Generation PAMAM Dendrimers (G0.5–G3.5) with Carboxylate End-Groups to Improve the DACHPtCl2 and 5-FU Efficacy as Anticancer Drugs

Molecules ◽  
2021 ◽  
Vol 26 (10) ◽  
pp. 2924
Author(s):  
Cláudia Camacho ◽  
Helena Tomás ◽  
João Rodrigues
Keyword(s):  
Cancer Cells ◽  
Cell Lines ◽  
Cancer Cell ◽  
Anticancer Drug ◽  
Water Solubility ◽  
Cancer Cell Lines ◽  
Pamam Dendrimers ◽  
Binding Assays ◽  
End Groups ◽  
Ic50 Values

The DACHPtCl2 compound (trans-(R,R)-1,2-diaminocyclohexanedichloroplatinum(II)) is a potent anticancer drug with a broad spectrum of activity and is less toxic than oxaliplatin (trans-l-diaminocyclohexane oxalate platinum II), with which it shares the active metal fragment DACHPt. Nevertheless, due to poor water solubility, its use as a chemotherapeutic drug is limited. Here, DACHPtCl2 was conjugated, in a bidentate form, with half-generation PAMAM dendrimers (G0.5–G3.5) with carboxylate end-groups, and the resulting conjugates were evaluated against various types of cancer cell lines. In this way, we aimed at increasing the solubility and availability at the target site of DACHPt while potentially reducing the adverse side effects. DNA binding assays showed a hyperchromic effect compatible with DNA helix’s disruption upon the interaction of the metallodendrimers and/or the released active metallic fragments with DNA. Furthermore, the prepared DACHPt metallodendrimers presented cytotoxicity in a wide set of cancer cell lines used (the relative potency regarding oxaliplatin was in general high) and were not hemotoxic. Importantly, their selectivity for A2780 and CACO-2 cancer cells with respect to non-cancer cells was particularly high. Subsequently, the anticancer drug 5-FU was loaded in a selected metallodendrimer (the G2.5COO(DACHPt)16) to investigate a possible synergistic effect between the two drugs carried by the same dendrimer scaffold and tested for cytotoxicity in A2780cisR and CACO-2 cancer cell lines. This combination resulted in IC50 values much lower than the IC50 for 5-FU but higher than those found for the metallodendrimers without 5-FU. It seems, thus, that the metallic fragment-induced cytotoxicity dominates over the cytotoxicity of 5-FU in the set of considered cell lines.

scholarly journals Ruthenium-based PACT agents based on bisquinoline chelates: synthesis, photochemistry, and cytotoxicity

2021 ◽  
Author(s):  
Anja Busemann ◽  
Ingrid Flaspohler ◽  
Xue-Quan Zhou ◽  
Claudia Schmidt ◽  
Sina K. Goetzfried ◽  
...  
Keyword(s):  
Quantum Yield ◽  
Singlet Oxygen ◽  
Cancer Cells ◽  
Cellular Uptake ◽  
Ruthenium Complex ◽  
Human Cancer ◽  
Light Irradiation ◽  
Quantum Yields ◽  
Light Activation ◽  
Human Cancer Cells

AbstractThe known ruthenium complex [Ru(tpy)(bpy)(Hmte)](PF6)2 ([1](PF6)2, where tpy = 2,2’:6’,2″-terpyridine, bpy = 2,2’-bipyridine, Hmte = 2-(methylthio)ethanol) is photosubstitutionally active but non-toxic to cancer cells even upon light irradiation. In this work, the two analogs complexes [Ru(tpy)(NN)(Hmte)](PF6)2, where NN = 3,3'-biisoquinoline (i-biq, [2](PF6)2) and di(isoquinolin-3-yl)amine (i-Hdiqa, [3](PF6)2), were synthesized and their photochemistry and phototoxicity evaluated to assess their suitability as photoactivated chemotherapy (PACT) agents. The increase of the aromatic surface of [2](PF6)2 and [3](PF6)2, compared to [1](PF6)2, leads to higher lipophilicity and higher cellular uptake for the former complexes. Such improved uptake is directly correlated to the cytotoxicity of these compounds in the dark: while [2](PF6)2 and [3](PF6)2 showed low EC50 values in human cancer cells, [1](PF6)2 is not cytotoxic due to poor cellular uptake. While stable in the dark, all complexes substituted the protecting thioether ligand upon light irradiation (520 nm), with the highest photosubstitution quantum yield found for [3](PF6)2 (Φ[3] = 0.070). Compounds [2](PF6)2 and [3](PF6)2 were found both more cytotoxic after light activation than in the dark, with a photo index of 4. Considering the very low singlet oxygen quantum yields of these compounds, and the lack of cytotoxicity of the photoreleased Hmte thioether ligand, it can be concluded that the toxicity observed after light activation is due to the photoreleased aqua complexes [Ru(tpy)(NN)(OH2)]2+, and thus that [2](PF6)2 and [3](PF6)2 are promising PACT candidates. Graphic abstract

Linear and high-molecular-weight poly-porphyrins for efficient photodynamic therapy

2021 ◽  
Author(s):  
Nan Zheng ◽  
Xiahui Li ◽  
Shangwei Huangfu ◽  
Kangkai Xia ◽  
Ruofei Yue ◽  
...  
Keyword(s):  
Molecular Weight ◽  
Photodynamic Therapy ◽  
Quantum Yield ◽  
Singlet Oxygen ◽  
High Molecular Weight ◽  
Linear Poly ◽  
High Molecular Weight Poly

A linear poly-porphyrin with high Mw and conjugated by PEG and acetazolamide was developed with enhanced singlet oxygen quantum yield, improved photo-toxicity and excellent in vivo photodynamic therapy.

Photodynamic therapy activities of phthalocyanine-based macromolecular photosensitizers on MCF-7 breast cancer cells

2021 ◽  
pp. 1-10
Author(s):  
Erem Ahmetali ◽  
Pinar Sen ◽  
N. Ceren Süer ◽  
Tebello Nyokong ◽  
Tarik Eren ◽  
...  
Keyword(s):  
Breast Cancer ◽  
Photodynamic Therapy ◽  
Cancer Cells ◽  
Breast Cancer Cells ◽  
Mcf 7
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