Towards improved halogenated BODIPY photosensitizers: clues on structural designs and heavy atom substitution patterns

Sánchez-Arroyo, Antonio J.; Palao, Eduardo; Agarrabeitia, Antonia R.; Ortiz, María J.; García‐Fresnadillo, David

doi:10.1039/c6cp06448e

Cited by 37 publications

(35 citation statements)

References 22 publications

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“…The studied haloBODIPYs were based on 8‐tolylBODIPY (Series A; compounds 2‐8 in Fig. 5 and Table 1) (74,75), trialkylBODIPY (Series B; compounds 9‐13 in Fig. 5 and Table 1) (75) and 8‐heteroatom‐substituted BODIPY (Series C; compounds 14‐17 in Fig.…”

Section: Resultsmentioning

confidence: 99%

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Exploring BODIPY Derivatives as Singlet Oxygen Photosensitizers for PDT

Prieto-Montero

Prieto‐Castañeda

Sola-Llano

et al. 2020

Photochem & Photobiology

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104

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This minireview is devoted to honoring the memory of Dr. Thomas Dougherty, a pioneer of modern photodynamic therapy (PDT). It compiles the most important inputs made by our research group since 2012 in the development of new photosensitizers based on BODIPY chromophore which, thanks to the rich BODIPY chemistry, allows a finely tuned design of the photophysical properties of this family of dyes to serve as efficient photosensitizers for the generation of singlet oxygen. These two factors, photophysical tuning and workable chemistry, have turned BODIPY chromophore as one of the most promising dyes for the development of improved photosensitizers for PDT. In this line, this minireview is mainly related to the establishment of chemical methods and structural designs for enabling efficient singlet oxygen generation in BODIPYs. The approaches include the incorporation of heavy atoms, such as halogens (iodine or bromine) in different number and positions on the BODIPY scaffold, and also transition metal atoms, by their complexation with Ir(III) center, for instance. On the other hand, low‐toxicity approaches, without involving heavy metals, have been developed by preparing several orthogonal BODIPY dimers with different substitution patterns. The advantages and drawbacks of all these diverse molecular designs based on BODIPY structural framework are described.

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Section: Resultsmentioning

confidence: 99%

“…5 and Table 1) (74,75), trialkylBODIPY (Series B; compounds 9‐13 in Fig. 5 and Table 1) (75) and 8‐heteroatom‐substituted BODIPY (Series C; compounds 14‐17 in Fig. 5 and Table 1) (76).…”

Section: Resultsmentioning

confidence: 99%

Exploring BODIPY Derivatives as Singlet Oxygen Photosensitizers for PDT

Prieto-Montero

Prieto‐Castañeda

Sola-Llano

et al. 2020

Photochem & Photobiology

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104

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“…The literature data for similar compounds in non-viscous solvents indicated that significant singlet oxygen production quantum yields (and hence the triplet state yields) are expected for both the alpha-Br and the beta-Br substitution of the BODIPY core. 37 At the same time, the fluorescence quantum yields in non-viscous solvents were not affected, compared to a non-substituted BODIPY. 38 To the best of our knowledge, the viscosity sensitivity of BODIPY dyes modified with Br substituents at the core was not previously investigated.…”

Section: View Article Onlinementioning

confidence: 88%

Exploring viscosity, polarity and temperature sensitivity of BODIPY-based molecular rotors

Vyšniauskas

López‐Duarte

Duchemin

et al. 2017

Phys. Chem. Chem. Phys.

105

126

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Microviscosity is a key parameter controlling the rate of diffusion and reactions on the microscale. One of the most convenient tools for measuring microviscosity is by fluorescent viscosity sensors termed 'molecular rotors'. BODIPY-based molecular rotors in particular proved extremely useful in combination with fluorescence lifetime imaging microscopy, for providing quantitative viscosity maps of living cells as well as measuring dynamic changes in viscosity over time. In this work, we investigate several new BODIPY-based molecular rotors with the aim of improving on the current viscosity sensing capabilities and understanding how the structure of the fluorophore is related to its function. We demonstrate that due to subtle structural changes, BODIPY-based molecular rotors may become sensitive to temperature and polarity of their environment, as well as to viscosity, and provide a photophysical model explaining the nature of this sensitivity. Our data suggests that a thorough understanding of the photophysics of any new molecular rotor, in environments of different viscosity, temperature and polarity, is a must before moving on to applications in viscosity sensing.

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“…One approach to obtain new molecules is focused on the synthesis of improved PS to overcome their limitations but this usually requires multistep chemistry increasing the costs and production time, hampering the implementation for clinical uses. In this context, BODIPY dyes have recently raised attention as potential photosensitizers [15][16][17][18]. They are characterized by intense absorption and emission bands in the green region and resistance to photobleaching [19,20].…”

Section: Introductionmentioning

confidence: 99%

“…Despite being highly fluorescent chromophores (antagonistic property to ROS generation) and poorly soluble in water, their synthesis allows an easy, versatile, and selective modification of their molecular structure to increase the population of the triplet state and consequently their singlet oxygen generation and also shifts their spectroscopic bands into the clinic window. These modifications include the addition of iodine heavy atoms, π-conjugated systems in the BODIPY skeleton, or the design of orthogonal BODIPY dimers [15,17,18,[21][22][23][24][25][26][27][28][29][30][31][32].…”

Section: Introductionmentioning

confidence: 99%

Functionalization of Photosensitized Silica Nanoparticles for Advanced Photodynamic Therapy of Cancer

Prieto-Montero

Prieto‐Castañeda

Katsumiti

et al. 2021

Preprint

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BODIPY dyes have recently raised attention as potential photosensitizers. In this work, commercial and novel photosensitizers (PSs) based on BODIPY chromophores (haloBODIPYs and orthogonal dimers strategically designed with intense bands in the blue, green or red region of the Visible spectra and high singlet oxygen production) were covalently linked to mesoporous silica nanoparticles (MSNs) further functionalized with PEG and folic acid (FA). MSNs of approximately 50 nm in size with different functional groups were synthesized to allow multiple alternatives of PS-PEG-FA decoration of their external surface. Different combinations varying the type of PS (commercial Rose Bengal, Thionine and Chlorine e6 or custom-made BODIPY-based), the linkage design and the length of PEG are detailed. All the nanosystems were physicochemically characterized (morphology, diameter, size distribution and PS loaded amount) and photophysically studied (absorption capacity, fluorescence efficiency, and singlet oxygen production) in suspension. For the most promising PS-PEG-FA silica nanoplatforms, the biocompatibility in dark conditions and the phototoxicity under suitable irradiation wavelengths (blue, green, or red) at regulated light doses (10-15 J/cm2) were compared with PSs free in solution in HeLa cells in vitro.

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Towards improved halogenated BODIPY photosensitizers: clues on structural designs and heavy atom substitution patterns

Cited by 37 publications

References 22 publications

Exploring BODIPY Derivatives as Singlet Oxygen Photosensitizers for PDT

Exploring BODIPY Derivatives as Singlet Oxygen Photosensitizers for PDT

Exploring viscosity, polarity and temperature sensitivity of BODIPY-based molecular rotors

Functionalization of Photosensitized Silica Nanoparticles for Advanced Photodynamic Therapy of Cancer

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