Incorporation of methylene blue into mesoporous silica nanoparticles for singlet oxygen generation

Xu, Jianan; Pelluau, Tristan; Monnereau, Cyrille; Guari, Yannick; Bonneviot, Laurent; Rodríguez, Montserrat; Albela, Belén

doi:10.1039/d2nj04835c

Cited by 9 publications

(6 citation statements)

References 38 publications

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“…It is generally acknowledged that both type I (ROS production) and type II (singlet oxygen production) photodynamic reactions are implicated in the tumor cell response to PDT and that the production of these bioactive compounds correlates with successful PDT [ 9 ]. Our results indicate a higher involvement of type I photodynamic reactions compared to type II ones, despite others who have previously shown that both ROS and 1 O 2 are generated by MB [ 41 , 63 ]. However, these results could be explained, considering that several factors may influence the ratio between type I and type II reactions, such as the type of sensitizer, the concentrations of substrate and oxygen, as well as the binding affinity of the sensitizer for the substrate [ 3 ].…”

Section: Discussioncontrasting

confidence: 82%

Polydopamine-Coated Liposomes for Methylene Blue Delivery in Anticancer Photodynamic Therapy: Effects in 2D and 3D Cellular Models

De Leo,

Marras,

Maurelli

et al. 2024

IJMS

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Photodynamic therapy (PDT) is a therapeutic option for cancer, in which photosensitizer (PS) drugs, light, and molecular oxygen generate reactive oxygen species (ROS) and induce cell death. First- and second-generation PSs presented with problems that hindered their efficacy, including low solubility. Thus, second-generation PSs loaded into nanocarriers were produced to enhance their cellular uptake and therapeutic efficacy. Among other compounds investigated, the dye methylene blue (MB) showed potential as a PS, and its photodynamic activity in tumor cells was reported even in its nanocarrier-delivered form, including liposomes. Here, we prepared polydopamine (PDA)-coated liposomes and efficiently adsorbed MB onto their surface. lipoPDA@MB vesicles were first physico-chemically characterized and studies on their light stability and on the in vitro release of MB were performed. Photodynamic effects were then assessed on a panel of 2D- and 3D-cultured cancer cell lines, comparing the results with those obtained using free MB. lipoPDA@MB uptake, type of cell death induced, and ability to generate ROS were also investigated. Our results show that lipoPDA@MB possesses higher photodynamic potency compared to MB in both 2D and 3D cell models, probably thanks to its higher uptake, ROS production, and apoptotic cell death induction. Therefore, lipoPDA@MB appears as an efficient drug delivery system for MB-based PDT.

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Section: Discussioncontrasting

confidence: 82%

Polydopamine-Coated Liposomes for Methylene Blue Delivery in Anticancer Photodynamic Therapy: Effects in 2D and 3D Cellular Models

De Leo,

Marras,

Maurelli

et al. 2024

IJMS

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“…MB and also with those of our previous systems based on a stellate type of nanoparticles [32]. We monitored the photobleaching of ADPA (3,3ʹ-(anthracene-9,10-diyl) dipropanoic acid) used as an 1 O2 scavenging probe, using the decrease of its characteristic fluorescence signal as outlined in our previously reported methodology, here described in Section 3.…”

Section: Studies In Watermentioning

confidence: 99%

“…The incorporation of methylene blue (MB) was then performed on aqueous surfactantfree samples. An n MB :n SiO2 molar ratio of 0.00064 was adopted, as it was the highest ratio allowing only negligible MB leaching in our previously reported ST nanoparticles [32]. The incorporation of the photosensitizer was performed in water by stirring the mixture at 25 • C for 1 h. The resulting samples were named MB@u-ST, MB@u-RB, MB@cs-ST/RB, MB@cs-RB/r, and MB@csc-ST/PhS/RB, with u = uniform, cs = core-shell, and csc = coreshell-corona.…”

Section: Incorporation Of Methylene Bluementioning

confidence: 99%

“…We carried out 1 O 2 generation experiments for all the samples displaying complete MB retention (MB@u-ST, MB@cs-ST/RB, MB@csc-ST/PhS/RB, and RB@(MB@ST)), in both water and methanol suspensions, in order to compare their performance with that of free MB and also with those of our previous systems based on a stellate type of nanoparticles [32]. We monitored the photobleaching of ADPA (3,3 ′ -(anthracene-9,10-diyl) dipropanoic acid) used as an 1 O 2 scavenging probe, using the decrease of its characteristic fluorescence signal as outlined in our previously reported methodology, here described in Section 3.…”

Section: Singlet Oxygen Generationmentioning

confidence: 99%

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Matrix Effect on Singlet Oxygen Generation Using Methylene Blue as Photosensitizer

Xu,

Bonneviot,

Guari

et al. 2024

Inorganics

Self Cite

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Methylene blue (MB) is a well-established and extensively studied photosensitizer for photodynamic therapy (PDT), since it can generate singlet oxygen with a high quantum yield upon irradiation within the phototherapeutic (600–950 nm) window. However, its activity can decrease due to the formation of dimers or higher aggregates, which can take place in an aqueous solution at relatively high concentrations. The incorporation of this molecule into a matrix can avoid this aggregation and increase its activity relative to PDT. Silica porous nanoparticles are chosen here as a matrix to host MB. The size and pore geometry are tuned in order to decrease MB leaching while maintaining good singlet oxygen generation and colloidal stability for further applications in nanomedicine. In addition, phenyl functions are grafted on the pores of the silica matrix in order to avoid MB aggregation, thereby increasing the activity of the photosensitizer in the singlet oxygen generation. DFT calculations give insight in the structure of the aggregation of the MB units, and the roles of water and organic environments are investigated through time-dependent calculations on UV-vis spectra.

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“…For a meaningful comparison with the molecular dyad, PTS was used for the Coulombic dyad at the same concentration as Ruphen (60 µM), resulting in 92% including oxygen, do not yield any product formation. For comparison, traditional organic photocatalysts for singlet oxygen generation, such as rose bengal, methylene blue, and eosin Y, [118][119][120][121][122][123][124][125] were employed in the experiments. However, their performance was notably lower, with yields below 20% following irradiation under our standardized conditions (yellow, pink and pale blue traces in Figure 5 (b)), despite their considerably higher extinction coefficients in the green spectral region compared to the employed ruthenium complexes.…”

Section: Exploiting the Long 3 Pts Lifetime For Photooxygenationsmentioning

confidence: 99%

Efficient Energy and Electron Transfer Photocatalysis with a Coulombic Dyad

Schmitz,

Bertrams,

Sell

et al. 2024

Preprint

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Photocatalysis holds great promise for changing the way how value-added molecules are currently prepared. However, many photocatalytic reactions suffer from lousy quantum yields, hampering the transition from lab-scale reactions to large-scale or even industrial applications. Molecular dyads can be designed such that the beneficial properties of inorganic and organic chromophores are combined, resulting in milder reaction conditions and improved quantum yields of photocatalytic reactions. We have developed a novel approach for obtaining the advantages of molecular dyads without the time- and resource-consuming synthesis of these tailored photocatalysts. Simply by mixing a cationic ruthenium complex with an anionic pyrene derivative in water a salt bichromophore is produced owing to electrostatic interactions. The long-lived organic triplet state is obtained by static and quantitative energy transfer from the preorganized ruthenium complex. We exploited this so-called Coulombic dyad for energy transfer catalysis with similar reactivity and even higher photostability compared to a molecular dyad and reference photosensitizers in several photooxygenations. In addition, it was shown that this system can also be used to maximize the quantum yield of photoredox reactions. This is due to an intrinsically higher cage escape quantum yield after photoinduced electron transfer for purely organic compounds compared to heavy atom-containing molecules. The combination of laboratory-scale as well as mechanistic irradiation experiments with detailed spectroscopic investigations provided deep mechanistic insights into this easy-to-use photocatalyst class.

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Incorporation of methylene blue into mesoporous silica nanoparticles for singlet oxygen generation

Abstract: Methylene blue is a known photosensitizer able to generate singlet oxygen. The main active species is the monomeric form. However, this dye has tendency to self-aggregate to form dimers and...

Cited by 9 publications

References 38 publications

Polydopamine-Coated Liposomes for Methylene Blue Delivery in Anticancer Photodynamic Therapy: Effects in 2D and 3D Cellular Models

Polydopamine-Coated Liposomes for Methylene Blue Delivery in Anticancer Photodynamic Therapy: Effects in 2D and 3D Cellular Models

Matrix Effect on Singlet Oxygen Generation Using Methylene Blue as Photosensitizer

Efficient Energy and Electron Transfer Photocatalysis with a Coulombic Dyad

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