Near-infrared phosphorescent terpyridine osmium(ii) photosensitizer complexes for photodynamic and photooxidation therapy

2020 ◽  
Vol 7 (20) ◽  
pp. 4020-4027
Author(s):  
Chen Ge ◽  
Jiayi Zhu ◽  
Ai Ouyang ◽  
Nong Lu ◽  
Yi Wang ◽  
...  
Keyword(s):  
Singlet Oxygen ◽  
Near Infrared ◽  
Red Light ◽  
Light Irradiation

NIR phosphorescent terpyridine Os(ii) complexes can produce singlet oxygen and oxidize NADH under both blue and red light irradiation.

Saline hybrid nanoparticles with phthalocyanine and tetraphenylporphine anions showing efficient singlet-oxygen production and photocatalysis

2018 ◽  
Vol 54 (10) ◽  
pp. 1245-1248 ◽  
Author(s):  
Marieke Poß ◽  
Henriette Gröger ◽  
Claus Feldmann
Keyword(s):  
Singlet Oxygen ◽  
Red Light ◽  
Light Irradiation ◽  
Hybrid Nanoparticles ◽  
Oxygen Production ◽  
Organic Hybrid

Gd43+[AlPCS4]34− and La43+[TPPS4]34− ([AlPCS4]4−: aluminium(iii) chlorido phthalocyanine tetrasulfonate; [TPPS4]4−: tetraphenylporphine sulfonate) inorganic–organic hybrid nanoparticles show efficient 1O2 production upon daylight and red-light irradiation.

scholarly journals Enabling in vivo Photocatalytic Activation of Rapid Bioorthogonal Chemistry by Repurposing Si-Rhodamine Fluorophores as Cytocompatible Far-Red Photocatalysts

2021 ◽  
Author(s):  
Chuanqi Wang ◽  
He Zhang ◽  
Tao Zhang ◽  
Xiaoyu Zou ◽  
Hui Wang ◽  
...  
Keyword(s):  
Singlet Oxygen ◽  
Chemical Reactions ◽  
Near Infrared ◽  
Red Light ◽  
3D Culture ◽  
Side Reactions ◽  
Bioorthogonal Chemistry ◽  
Long Wavelength ◽  
Spatiotemporal Control

<p><a></a>Chromophores that absorb in the tissue-penetrant far-red/near-infrared window have long served as photocatalysts for the generation of singlet oxygen for photodynamic therapy. However, the cytotoxicity and side-reactions associated with singlet oxygen sensitization have posed a problem for using long wavelength photocatalysis to initiate other types of chemical reactions in biological environments. Described here is the use of Si-Rhodamine (SiR) dyes as photocatalysts for inducing rapid bioorthogonal chemistry using 660 nm light through the oxidation of a dihydrotetrazine to a tetrazine in the presence of trans-cyclooctene dienophiles. SiRs have been commonly used as fluorophores for applications in biology, but have not previously been applied to catalyze chemical reactions. A dihydrotetrazine/tetrazine pair is described that displays high stability in both oxidation states. A series of SiR derivatives were evaluated, and the Janelia-SiR dyes were found to be especially effective in catalyzing rapid photooxidation at low catalyst loadings (typically 1 µM). A protein that was site-selectively modified by trans-cyclooctene was quantitively conjugated upon exposure to 660 nm light and a dihydrotetrazine. By contrast, a previously described methylene blue catalyst was found to rapidly degrade the protein. SiR-red light photocatalysis was used to crosslink hyaluronic acid derivatives that were functionalized by dihydrotetrazine and trans-cyclooctenes, enabling 3D culture of human prostate cancer cells. This photoinducible hydrogel formation could also be carried out in vivo in live mice through subcutaneous injection of a solution containing SiR photocatalyst and a Cy7-labeled hydrogel precursor, followed by brief in vivo irradiation with 660 nm light to produce a stable hydrogel material. This cytocompatible method for using red light photocatalysis to activate bioorthogonal chemistry is anticipated to find broad applications where spatiotemporal control is needed in the in vivo environment. <br></p>

scholarly journals Enabling in vivo Photocatalytic Activation of Rapid Bioorthogonal Chemistry by Repurposing Si-Rhodamine Fluorophores as Cytocompatible Far-Red Photocatalysts

2021 ◽  
Author(s):  
Chuanqi Wang ◽  
He Zhang ◽  
Tao Zhang ◽  
Xiaoyu Zou ◽  
Hui Wang ◽  
...  
Keyword(s):  
Singlet Oxygen ◽  
Chemical Reactions ◽  
Near Infrared ◽  
Red Light ◽  
3D Culture ◽  
Side Reactions ◽  
Bioorthogonal Chemistry ◽  
Long Wavelength ◽  
Spatiotemporal Control

<p><a></a>Chromophores that absorb in the tissue-penetrant far-red/near-infrared window have long served as photocatalysts for the generation of singlet oxygen for photodynamic therapy. However, the cytotoxicity and side-reactions associated with singlet oxygen sensitization have posed a problem for using long wavelength photocatalysis to initiate other types of chemical reactions in biological environments. Described here is the use of Si-Rhodamine (SiR) dyes as photocatalysts for inducing rapid bioorthogonal chemistry using 660 nm light through the oxidation of a dihydrotetrazine to a tetrazine in the presence of trans-cyclooctene dienophiles. SiRs have been commonly used as fluorophores for applications in biology, but have not previously been applied to catalyze chemical reactions. A dihydrotetrazine/tetrazine pair is described that displays high stability in both oxidation states. A series of SiR derivatives were evaluated, and the Janelia-SiR dyes were found to be especially effective in catalyzing rapid photooxidation at low catalyst loadings (typically 1 µM). A protein that was site-selectively modified by trans-cyclooctene was quantitively conjugated upon exposure to 660 nm light and a dihydrotetrazine. By contrast, a previously described methylene blue catalyst was found to rapidly degrade the protein. SiR-red light photocatalysis was used to crosslink hyaluronic acid derivatives that were functionalized by dihydrotetrazine and trans-cyclooctenes, enabling 3D culture of human prostate cancer cells. This photoinducible hydrogel formation could also be carried out in vivo in live mice through subcutaneous injection of a solution containing SiR photocatalyst and a Cy7-labeled hydrogel precursor, followed by brief in vivo irradiation with 660 nm light to produce a stable hydrogel material. This cytocompatible method for using red light photocatalysis to activate bioorthogonal chemistry is anticipated to find broad applications where spatiotemporal control is needed in the in vivo environment. <br></p>

Singlet Oxygen Release and Cell Toxicity of a Chemiluminescent Squaraine Rotaxane Dye: Implications for Molecular Imaging

2011 ◽  
Vol 64 (5) ◽  
pp. 604 ◽  
Author(s):  
Jung-Jae Lee ◽  
Amanda Gonçalves ◽  
Bryan A. Smith ◽  
Rachel Palumbo ◽  
Alexander G. White ◽  
...  
Keyword(s):  
Molecular Imaging ◽  
Singlet Oxygen ◽  
Cell Cultures ◽  
Near Infrared ◽  
Red Light ◽  
Infrared Emission ◽  
Water Soluble ◽  
Cell Toxicity ◽  
Squaraine Rotaxane

The water soluble tetraguanidinium squaraine rotaxane 2 was prepared and photoconverted to its corresponding squaraine rotaxane endoperoxide (SREP), 2EP. As expected, 2EP undergoes a thermal cycloreversion reaction that releases 60 ± 4% singlet oxygen and produces near-infrared emission in aqueous solution. Cell toxicity assays in the dark, using human and bacterial cell cultures, showed that 2EP (up to 20 µM) is no more toxic than its parent 2. This suggests that SREP-derived imaging probes are not likely to exhibit a significant toxicity effect due to the slow release of stoichiometric amounts of singlet oxygen. Additional photosensitization experiments showed that tetraguanidinium squaraine rotaxane 2 is a weak photosensitizer, but nonetheless, red light irradiation of cell cultures that were pre-incubated with 2 (>3 µM) produced moderate phototoxicity. Fluorescence microscopy studies attribute the phototoxicity of 2 to its ability to penetrate into the cell cytosol. The implications of these results are discussed in the context of effective methods to activate SREP as chemiluminescent probes for in vivo optical molecular imaging.

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

scholarly journals New Approach in the Application of Conjugated Polymers: The Light-Activated Source of Versatile Singlet Oxygen Molecule

Materials ◽  
2021 ◽  
Vol 14 (5) ◽  
pp. 1098
Author(s):  
Agata Blacha-Grzechnik
Keyword(s):  
Conjugated Polymers ◽  
Singlet Oxygen ◽  
Near Infrared ◽  
Photophysical Properties ◽  
Short Review ◽  
The Novel ◽  
New Approach ◽  
Intermolecular Energy ◽  
Intermolecular Energy Transfer ◽  
High Absorption

For many years, the research on conjugated polymers (CPs) has been mainly focused on their application in organic electronics. Recent works, however, show that due to the unique optical and photophysical properties of CPs, such as high absorption in UV–Vis or even near-infrared (NIR) region and efficient intra-/intermolecular energy transfer, which can be relatively easily optimized, CPs can be considered as an effective light-activated source of versatile and highly reactive singlet oxygen for medical or catalytic use. The aim of this short review is to present the novel possibilities that lie dormant in those exceptional polymers with the extended system of π-conjugated bonds.

Biodegradable Nano-photosensitizer with Photoactivatable Singlet Oxygen Generation for Synergistic Phototherapy

2021 ◽  
Author(s):  
Jiaxin Shen ◽  
Dandan Chen ◽  
Ye Liu ◽  
Guoyang Gao ◽  
Zhihe Liu ◽  
...  
Keyword(s):  
Photodynamic Therapy ◽  
Cancer Therapy ◽  
Singlet Oxygen ◽  
Near Infrared ◽  
Promising Method ◽  
Normal Cells ◽  
Oxygen Generation ◽  
Singlet Oxygen Generation ◽  
Nir Light

Photodynamic therapy (PDT) is a promising method for cancer therapy and also may initiate unexpected damages to normal cells and tissues. Herein, we developed a near-infrared (NIR) light-activatable nanophotosensitizer, which...

Tumor Microenvironment-Regulating Immunosenescence-Independent Nanostimulant Synergizing with Near-Infrared Light Irradiation for Antitumor Immunity

2021 ◽  
Vol 13 (4) ◽  
pp. 4844-4852
Author(s):  
Saji Uthaman ◽  
Shameer Pillarisetti ◽  
Hye Suk Hwang ◽  
Ansuja Pulickal Mathew ◽  
Kang Moo Huh ◽  
...  
Keyword(s):  
Tumor Microenvironment ◽  
Antitumor Immunity ◽  
Near Infrared ◽  
Light Irradiation ◽  
Infrared Light ◽  
Near Infrared Light
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