Synthesis, structural, spectroscopic, computational and cytotoxic studies of BODIPY dyes

Laine, Marina; Barbosa, Nuno; Kochel, Andrzej; Osiecka, Beata J.; Szewczyk, Grzegorz; Sarna, Tadeusz; Ziółkowski, Piotr; Wieczorek, Robert; Filarowski, Aleksander

doi:10.1016/j.snb.2016.07.103

Cited by 27 publications

(13 citation statements)

References 54 publications

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“…35 However, the covalent attachment of heavy atoms further hinders synthetic work and often leads to an increase in dark toxicity. 36,37 Also, the presence of heavy atoms covalent binding to BODIPY inhibits its emission of fluorescence. On the other hand, by external addition of the heavy atoms, it is possible to use these compounds in dual form, as photosensitizers and also as fluorophores for cellular imaging.…”

Section: Discussionmentioning

confidence: 99%

Photodynamic inactivation of microorganisms sensitized by cationic BODIPY derivatives potentiated by potassium iodide

Reynoso

Quiroga

Agazzi

et al. 2017

Photochem Photobiol Sci

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The photodynamic inactivation mediated by 1,3,5,7-tetramethyl-8-[4-(N,N,N-trimethylamino)phenyl]-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene 3 and 8-[4-(3-(N,N,N-trimethylamino)propoxy)phenyl]-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene 4 was investigated on Staphylococcus aureus, Escherichia coli and Candida albicans. In vitro experiments indicated that BODIPYs 3 and 4 were rapidly bound to microbial cells at short incubation periods. Also, fluorescence microscopy images showed green emission of BODIPYs bound to microbial cells. Photosensitized inactivation improved with an increase of the irradiation time. Similar photoinactivation activities were found for both BODIPYs in bacteria. The photoinactivation induced by these BODIPYs was effective for both bacteria. However, the Gram-positive bacterium was inactivated sooner and with a lower concentration of a photosensitizer than the Gram-negative bacterium. After 15 min irradiation, the complete eradication of S. aureus was obtained with 1 μM photosensitizer. A reduction of 4.5 log in the E. coli viability was found when using 5 μM photosensitizer and 30 min irradiation. Also, the last conditions produced a decrease of 4.5 log in C. albicans cells treated with BODIPY 3, while 4 was poorly effective. On the other hand, the effect of the addition of KI on photoinactivation at different irradiation periods and salt concentrations was investigated. A smaller effect was observed in S. aureus because the photosensitizers alone were already very effective. In E. coli, photokilling potentiation was mainly found at longer irradiation periods. Moreover, the photoinactivation of C. albicans mediated by these BODIPYs was increased in the presence of KI. In solution, an increase in the formation of the BODIPY triplet states was observed with the addition of the salt, due to the effect of external heavy atoms. The greater intersystem crossing together with the formation of reactive iodine species induced by BODIPYs may be contributing to enhance the inactivation of microorganisms. Therefore, these BODIPYs represent interesting photosensitizers to inactivate microorganisms. In particular, BODIPY 3 in combination with KI was highly effective as a broad spectrum antimicrobial photosensitizer.

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Section: Discussionmentioning

confidence: 99%

Photodynamic inactivation of microorganisms sensitized by cationic BODIPY derivatives potentiated by potassium iodide

Reynoso

Quiroga

Agazzi

et al. 2017

Photochem Photobiol Sci

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“…Among the multiple therapies against cancer, photodynamic therapy (PDT) is a promising one due to its advantages of low systemic damage, noninvasion, and controllable characteristics. Thus, various photosensitizers have been developed for PDT. − Among these photosensitizers, boron dipyrromethene (BODIPY) derivatives are recognized as potential candidates for dual-use as bioimaging and PDT therapeutic agents owing to their excellent photostability and high molar extinction coefficient. − These BODIPY derivatives, however, usually suffer from low singlet oxygen ( 1 O 2 ) quantum yield (QYs, Φ Δ ), which is one key factor to determine the performance of photosensitizers.…”

Section: Introductionmentioning

confidence: 99%

BODIPY Derivatives for Photodynamic Therapy: Influence of Configuration versus Heavy Atom Effect

Zou

Yin

Ding

et al. 2017

ACS Appl. Mater. Interfaces

219

131

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Heavy atom effect and configuration are important for BODIPY derivatives to generate singlet oxygen (O) for photodynamic therapy. Herein, a series of BODIPY derivatives with different halogens were synthesized. O quantum yields (QYs) and MTT assay confirm that incorporation of more heavy atoms onto dimeric BODIPY cannot effectively enhance the O QYs. Rather, the dark toxicity increases. This phenomenon can be attributed to the competition of heavy atom effect and configuration of dimeric BODIPY. In addition the BODIPY derivative with two iodine atoms (BDPI) owns the highest O QYs (73%) and the lowest phototoxicity IC (1 μM). Furthermore, an in vivo study demonstrates that BDPI NPs can effectively inhibit tumor growth and can be used as a promising threanostic agent for photodynamic therapy in clinic.

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“…7 Chemists continue to design and synthesize a variety of novel NIR dyes, including organic uorophores such as cyanines, rhodamine analogs, 4,4-diuoro-4-bora-3a,4a-diaza-s-indacene (BODIPYs), squaraines, phthalocyanines, porphyrin derivatives, conjugated polymer and inorganic dyes (quantum dots). [7][8][9][10][11] Although the quantum dots principally present interesting alternatives, cytotoxicity and stability concerns, as well as difficulties in the reproducibility of their preparation, need to be resolved. 2,11 Compared to inorganic dyes, organic NIR uorophores display an improvement in photophysical properties and have availability for large-scale chemical synthesis.…”

Section: Introductionmentioning

confidence: 99%

“…2,11 Compared to inorganic dyes, organic NIR uorophores display an improvement in photophysical properties and have availability for large-scale chemical synthesis. 7,9 However, only a few of them are readily available owing to poor water solubility, which probably brings about dye accumulation in normal organs causing systemic toxicity.…”

Section: Introductionmentioning

confidence: 99%

Near-infrared polyfluorene encapsulated in poly(ε-caprolactone) nanoparticles with remarkable large Stokes shift

et al. 2020

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Synthesis, structural, spectroscopic, computational and cytotoxic studies of BODIPY dyes

Cited by 27 publications

References 54 publications

Photodynamic inactivation of microorganisms sensitized by cationic BODIPY derivatives potentiated by potassium iodide

Photodynamic inactivation of microorganisms sensitized by cationic BODIPY derivatives potentiated by potassium iodide

BODIPY Derivatives for Photodynamic Therapy: Influence of Configuration versus Heavy Atom Effect

Near-infrared polyfluorene encapsulated in poly(ε-caprolactone) nanoparticles with remarkable large Stokes shift

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