Regulating 1O2 generation from heavy-atom-free triplet photosensitizers based on thiophene-fused BODIPY

Pham, Thanh Chung; Cho, Moonyeon; Nguyen, Van‐Nghia; Nguyen, Timothy; Kim, Gyoungmi; Min, Sung-Wook; Kim, Mi-Ra; Yoon, Juyoung; Lee, Songyi

doi:10.1016/j.dyepig.2023.111617

Cited by 6 publications

(5 citation statements)

References 24 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Cz-SB was synthesized through the trifluoroacetic acid-catalyzed condensation of 9-ethyl-3-carbazolecarboxaldehyde with thiophene-fused pyrrole, subsequent oxidation, and borylation, as delineated in Scheme . The synthetic methodology employed herein has been detailed in our antecedent publication . The structural authenticity of Cz-SB was ascertained through 1 H NMR and HR-MS, as illustrated in Figure S1 and Supporting Information.…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Charge Transfer-Promoted Excited State of a Heavy-Atom-Free Photosensitizer for Efficient Application of Mitochondria-Targeted Fluorescence Imaging and Hypoxia Photodynamic Therapy

Pham,

Cho,

Nguyen

et al. 2024

ACS Appl. Mater. Interfaces

Self Cite

View full text Add to dashboard Cite

Conventional photosensitizers (PSs) used in photodynamic therapy (PDT) have shown preliminary success; however, they are often associated with several limitations including potential dark toxicity in healthy tissues, limited efficacy under acidic and hypoxic conditions, suboptimal fluorescence imaging capabilities, and nonspecific targeting during treatment. In response to these challenges, we developed a heavy-atom-free PS, denoted as Cz-SB, by incorporating ethyl carbazole into a thiophene-fused BODIPY core. A comprehensive investigation into the photophysical properties of Cz-SB was conducted through a synergistic approach involving experimental and computational investigations. The enhancement of intersystem crossing (k ISC ) and fluorescence emission (k fl ) rate constants was achieved through a donor−acceptor pair-mediated charge transfer mechanism. Consequently, Cz-SB demonstrated remarkable efficiency in generating reactive oxygen species (ROS) under acidic and low-oxygen conditions, making it particularly effective for hypoxic cancer PDT. Furthermore, Cz-SB exhibited good biocompatibility, fluorescence imaging capabilities, and a high degree of localization within the mitochondria of living cells. We posit that Cz-SB holds substantial prospects as a versatile PS with innovative molecular design, representing a potential "one-for-all" solution in the realm of cancer phototheranostics.

show abstract

Section: Resultsmentioning

confidence: 99%

“…The synthetic methodology employed herein has been detailed in our antecedent publication. 49 The structural authenticity of Cz-SB was ascertained through 1 H NMR and HR-MS, as illustrated in Figure S1 and Supporting Information.…”

Section: •−mentioning

confidence: 99%

Charge Transfer-Promoted Excited State of a Heavy-Atom-Free Photosensitizer for Efficient Application of Mitochondria-Targeted Fluorescence Imaging and Hypoxia Photodynamic Therapy

Pham,

Cho,

Nguyen

et al. 2024

ACS Appl. Mater. Interfaces

Self Cite

View full text Add to dashboard Cite

show abstract

“…Besides, the oxygen reduction radicals’ patterns from the CV test were studied by electron paramagnetic resonance (EPR) spectroscopy, where 2,2,6,6-tetramethyl-4-piperidinol (TMP) acted as the capture agent (Figure D). The characteristic triple peaks appear with the intensity ratio of 1:1:1 for the BET-[BMIm] system, corresponding to the typical TMP– 1 O 2 adduct (curve a), showing the stronger interactions of the emitter with the oxygen-based radials . This phenomenon is forcefully supported by the BET system, where a similar peak is found with a stronger intensity under the same conditions (curve b).…”

Section: Resultsmentioning

confidence: 99%

“…Simultaneously, there emerge the stronger characteristic triple peaks of 1 O 2 radicals in the EPR spectrum of PPIX by lighting irradiation (Figure B, curve a), identifying PPIX as an excellent photosensitizer in this test . Interestingly, the corresponding peak intensities decrease violently for the PPIX/BET under the same condition (Figure B, curve b), illustrating the stronger interactions of the BET with 1 O 2 species . Upon light irradiation, there display the minimal EPR peaks (Figure B, curve c), certifying that the ionic liquid enhances the photodynamic reaction of the emitter with 1 O 2 species.…”

Section: Resultsmentioning

confidence: 99%

Photodynamic-Assisted Electrochemiluminescence Enhancement toward Advanced BODIPY for Precision Diagnosis of Parkinson

Song,

Liu,

Bao

et al. 2024

Anal. Chem.

View full text Add to dashboard Cite

Nowadays, signal enhancement is imperative to increase sensitivity of advanced ECL devices for expediting their promising applications in clinic. In this work, photodynamicassisted electrochemiluminescence (PDECL) device was constructed for precision diagnosis of Parkinson, where an advanced emitter was prepared by electrostatically linking 2,6-dimethyl-8-(3carboxyphenyl)4,4′-difluoroboradiazene (BET) with 1-butyl-3methylimidazole tetrafluoroborate ([BMIm][BF 4 ]). Specifically, protoporphyrin IX (PPIX) can trigger the photodynamic reaction under light irradiation with a wavelength of 450 nm to generate lots of singlet oxygen ( 1 O 2 ), showing a 2.43-fold magnification in the ECL responses. Then, the aptamer (Apt) was assembled on the functional BET-[BMIm] for constructing a "signal off" ECL biosensor. Later on, the PPIX was embedded into the G-quadruplex (G4) of the Apt to magnify the ECL signals for bioanalysis of α-synuclein (α-syn) under light excitation. In the optimized surroundings, the resulting PDECL sensor has a broad linear range of 100.0 aM ∼ 10.0 fM and a low limit of detection (LOD) of 63 aM, coupled by differentiating Parkinson patients from normal individuals according to the receiver operating characteristic (ROC) curve analysis of actual blood samples. Such research holds great promise for synthesis of other advanced luminophores, combined with achieving an early clinical diagnosis.

show abstract

“…Historically, research on thiophenes has been predominantly focused on petrochemical derivatization processes, particularly in the context of asphaltenes [ 53 , 54 ]. Their potential in the medical field, especially in PDT, has been largely overlooked [ 55 , 56 , 57 ]. This lack of recognition might account for the limited exploration of the reactivity of thiophene-containing compounds in the presence of singlet oxygen.…”

Section: Introductionmentioning

confidence: 99%

Thiophene Stability in Photodynamic Therapy: A Mathematical Model Approach

Alcázar

2024

IJMS

View full text Add to dashboard Cite

Thiophene-containing photosensitizers are gaining recognition for their role in photodynamic therapy (PDT). However, the inherent reactivity of the thiophene moiety toward singlet oxygen threatens the stability and efficiency of these photosensitizers. This study presents a novel mathematical model capable of predicting the reactivity of thiophene toward singlet oxygen in PDT, using Conceptual Density Functional Theory (CDFT) and genetic programming. The research combines advanced computational methods, including various DFT techniques and symbolic regression, and is validated with experimental data. The findings underscore the capacity of the model to classify photosensitizers based on their photodynamic efficiency and safety, particularly noting that photosensitizers with a constant rate 1000 times lower than that of unmodified thiophene retain their photodynamic performance without substantial singlet oxygen quenching. Additionally, the research offers insights into the impact of electronic effects on thiophene reactivity. Finally, this study significantly advances thiophene-based photosensitizer design, paving the way for therapeutic agents that achieve a desirable balance between efficiency and safety in PDT.

show abstract

Regulating 1O2 generation from heavy-atom-free triplet photosensitizers based on thiophene-fused BODIPY

Cited by 6 publications

References 24 publications

Charge Transfer-Promoted Excited State of a Heavy-Atom-Free Photosensitizer for Efficient Application of Mitochondria-Targeted Fluorescence Imaging and Hypoxia Photodynamic Therapy

Charge Transfer-Promoted Excited State of a Heavy-Atom-Free Photosensitizer for Efficient Application of Mitochondria-Targeted Fluorescence Imaging and Hypoxia Photodynamic Therapy

Photodynamic-Assisted Electrochemiluminescence Enhancement toward Advanced BODIPY for Precision Diagnosis of Parkinson

Thiophene Stability in Photodynamic Therapy: A Mathematical Model Approach

Contact Info

Product

Resources

About