Recent developments of BODIPY-based colorimetric and fluorescent probes for the detection of reactive oxygen/nitrogen species and cancer diagnosis

Nguyen, Van‐Nghia; Ha, Jeongsun; Cho, Moonyeon; Li, Haidong; Swamy, K. M.K.; Yoon, Juyoung

doi:10.1016/j.ccr.2021.213936

Cited by 171 publications

(70 citation statements)

References 102 publications

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“…Among them, para -pyridinium BODIPY PS VI attracted our attention and we selected it as the leading compound since it contained the methyl pyridinium portion both as the key substituent of BODIPY and as the important interaction moiety to microbials. Among our reported works and from other reports, it has been well demonstrated that meso -pyridinium species induces significantly reduced fluorescence of BODIPY fluorophore due to photoinduced electron transfer (PET), and the immolation of pyridinium to pyridine moiety is useful to develop various fluorescent probes of biothiols, ROS, etc. , Such PET regulation was also applied to adjust the production of ROS. , We speculate that by installation of pyridinium moiety at the meso position of 2,6-diiodo-1,3,5,7-tetramethyl BODIPY by varying the position of nitrogen and evaluating the capping moiety, we may understand important factors for aPDT activities, e.g., PET effect, π–π stacking, water solubility, etc. It is well known that π–π stacking plays an important role in ROS production and fluorescence emission .…”

Section: Resultsmentioning

confidence: 80%

“…Among our reported works and from other reports, it has been well demonstrated that meso-pyridinium species induces significantly reduced fluorescence of BODIPY fluorophore due to photoinduced electron transfer (PET), and the immolation of pyridinium to pyridine moiety is useful to develop various fluorescent probes of biothiols, ROS, etc. 48,49 Such PET regulation was also applied to adjust the production of ROS. 50,51 We speculate that by installation of pyridinium moiety at the meso position of 2,6-diiodo-1,3,5,7-tetramethyl BODIPY by varying the position of nitrogen and evaluating the capping moiety, we may understand important factors for aPDT activities, e.g., PET effect, π−π stacking, water solubility, etc.…”

Section: Resultsmentioning

confidence: 99%

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Discovery of Meso-(meta-Pyridinium) BODIPY Photosensitizers: In Vitro and In Vivo Evaluations for Antimicrobial Photodynamic Therapy

Lin

Zhang

et al. 2021

J. Med. Chem.

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Antimicrobial photodynamic therapy (aPDT) has emerged as a novel and promising approach for the treatment of pathogenic microorganism infections. The efficacy of aPDT depends greatly on the behavior of the photosensitizer. Herein, we report the design, preparation, antimicrobial photodynamic activities, as well as structure–activity relationships of a series of photosensitizers modified at the meso position of a 1,3,5,7-tetramethyl BODIPY scaffold with various pyridinyl and pyridinium moieties. The photodynamic antimicrobial activities of all photosensitizers have been tested against Staphylococcus aureus, Escherichia coli, Candida albicans, and Methicillin-resistant S. aureus (MRSA). The methyl meso-(meta-pyridinium) BODIPY photosensitizer (3c) possessed the highest phototoxicity against these pathogens at minimal inhibitory concentrations (MIC) ranging from 0.63 to 1.25 μM with a light dose of 81 J/cm2. Furthermore, 3c exhibited an impressive antimicrobial efficacy in S. aureus-infected mice wounds. Taken together, these findings suggest that 3c is a promising candidate as the antimicrobial photosensitizer for combating pathogenic microorganism infections.

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Section: Resultsmentioning

confidence: 80%

Section: Resultsmentioning

confidence: 99%

Discovery of Meso-(meta-Pyridinium) BODIPY Photosensitizers: In Vitro and In Vivo Evaluations for Antimicrobial Photodynamic Therapy

Lin

Zhang

et al. 2021

J. Med. Chem.

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“…Over the past few decades, boron-dipyrromethene (BODIPY) dyes have received considerable attention as promising theranostic agents because of unique advantages, such as large molar absorption coefficients, high fluorescence quantum yields, outstanding photo- and chemical stabilities, and feasible derivatizations. , BODIPY-based PSs are generally designed by incorporating heavy atoms to enhance intersystem crossing (ISC), − which, however, limits biomedical applications mainly because of concerns about dark toxicity and reduced triplet state lifetimes. , To overcome these drawbacks, great efforts have been devoted to developing BODIPY-based PSs without heavy atoms for PDT. − Recently, a promising strategy to develop efficient heavy-atom-free BODIPY PSs based on donor–acceptor (D–A) structures has been demonstrated, but the ISC mechanism remains elusive. − An enhanced understanding of the ISC mechanism is crucial for guiding the molecular design of BODIPY-based PSs. Although several BODIPY PSs based on D–A structures have been used for cancer PDT, ROS generation by D-BODIPY PSs has not been effectively realized thus far in a practical application .…”

Section: Introductionmentioning

confidence: 99%

Access to the Triplet Excited States of Heavy-Atom-Free Boron-Dipyrromethene Photosensitizers via Radical Pair Intersystem Crossing for Image-Guided Tumor-Targeted Photodynamic Therapy

Nguyen

Koh

et al. 2021

Chem. Mater.

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Boron-dipyrromethene (BODIPY) dyes have aroused considerable interest in cancer theranostics over the past decade because of robust photochemical properties. Although a large number of BODIPY photosensitizers (PSs) containing heavy atoms have been reported, the development of heavy-atom-free BODIPY PSs for oncologic photodynamic therapy (PDT) has been limited mainly by the uncertainty in intersystem crossing (ISC) mechanisms, unbalanced phototoxic effectiveness and fluorescence quantum yields, and aggregation-caused quenching effects. In addition, the lack of extensive in vivo studies of heavy-atom-free BODIPY PSs continues to limit clinical application. Herein, novel heavy-atom-free BODIPY-phenoxazine triads (BDP-8/BDP-9) that generate efficient excited triplet states via radical pair intersystem crossing (RP-ISC) followed by triplet charge recombination were developed for use in fluorescence image-guided PDT. BDP-8/BDP-9 exhibited high molar absorption coefficients, prominent aggregation-induced emission, and excellent singlet oxygen generation capability upon light irradiation. The corresponding BODIPY nanoparticles (BDP-8/BDP-9 NPs) with bright red emission, considerable phototoxicity, and excellent tumor-targeting ability were simply prepared by encapsulating BDP-8/BDP-9 PSs in a polymeric matrix. More importantly, the results of both in vitro and in vivo experiments demonstrated the considerable potential of BDP-8 NPs for image-guided photodynamic cancer therapy. This study may inspire the development of potential BODIPY-based nanoagents for cancer theranostics.

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“…In recent years, colorimetric and fluorescent probes have become an effective analytical tool due to unique capability for sensitive monitoring of metal ions [1,2], anions [3,4], reactive oxygen species [5,6] and biomolecules [7,8]. Among the various chromophore scaffolds, lactam derivatives of rhodamines represent one of the most developed platform for the design of selective colorimetric and fluorescent probes due to their high extinction coefficients, high quantum yields, and excellent chemical and photostability [9,10].…”

Section: Introductionmentioning

confidence: 99%

FRET Pumping of Rhodamine-Based Probe in Light-Harvesting Nanoparticles for Highly Sensitive Detection of Cu2+

Mironenko

Tutov

Chepak

et al. 2021

Preprint

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In this work we presented novel strategy for increasing the performance of popular fluorescent probes on the basis of rhodamine-lactam platform. This strategy is based on the incorporation of probe molecules into the light-harvesting nanoparticles to pump modulated optical signal by Förster resonant energy transfer. Using the commercially available Cu2+ probe as a reference chemical, we have developed an efficient approach to significantly improve its sensing performance. Within obtained nanoparticles coumarin-30 nanoantenna absorbs excitation light and pumps incorporated sensing molecules providing bright fluorescence to a small number of emitters, while changing the probe-analyte equilibrium from liquid-liquid to solid-liquid significantly increased the apparent association constant, which together provided a ~100-fold decrease in the detection limit. The developed nanoprobe allows highly sensitive detection of Cu2+ ions in aqueous media without organic co-solvents usually required for dissolution of the probe, and demonstrate compatibility with inexpensive fluorometers and the ability to detect low concentrations with the naked eye.

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Recent developments of BODIPY-based colorimetric and fluorescent probes for the detection of reactive oxygen/nitrogen species and cancer diagnosis

Cited by 171 publications

References 102 publications

Discovery of Meso-(meta-Pyridinium) BODIPY Photosensitizers: In Vitro and In Vivo Evaluations for Antimicrobial Photodynamic Therapy

Discovery of Meso-(meta-Pyridinium) BODIPY Photosensitizers: In Vitro and In Vivo Evaluations for Antimicrobial Photodynamic Therapy

Access to the Triplet Excited States of Heavy-Atom-Free Boron-Dipyrromethene Photosensitizers via Radical Pair Intersystem Crossing for Image-Guided Tumor-Targeted Photodynamic Therapy

FRET Pumping of Rhodamine-Based Probe in Light-Harvesting Nanoparticles for Highly Sensitive Detection of Cu2+

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