A new mitochondrial probe combining pyrene and a triphenylphosphonium salt for cellular oxygen and free radical detection via fluorescence lifetime measurements

Wawi, Mohamad Jamal; Mähler, Christoph; Inguimbert, Nicolas; Marder, Todd B.; Ribou, Anne‐Cécile

doi:10.1080/10715762.2022.2077202

Cited by 8 publications

(2 citation statements)

References 60 publications

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“…[37][38][40][41][42][43][44][45][46][47][48][49][50][51][52][53][54][55] In cells, pyrene has been used to detect reactive oxygen species (ROS). [56][57][58][59] With its HOMO (Figure 1) having major contributions at carbons 1,3,6 and 8, these positions readily undergo electrophilic substitution. [1,[60][61][62][63][64][65][66] Substitution at the equivalent 4,5,9and 10-positions, referred to as K-region, takes advantages of their alkene-like nature using alkene-selective reagents.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Photophysical and Electronic Properties of a D‐π‐A Julolidine‐Like Pyrenyl‐o‐Carborane

Krebs,

Brändler,

Krummenacher

et al. 2024

Chemistry A European J

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We synthesized 2‐(1‐1,2‐dicarbadodecaboranyl(12))‐6,6,12,12‐tetramethyl‐7,8,11,12‐tetrahydro‐6H,10H‐phenaleno[1,9‐fg]pyrido[3,2,1‐ij]quinoline (4) a julolidine‐like pyrenyl‐o‐carborane, with pyrene substituted at the 2,7‐positions on the HOMO/LUMO nodal plane. Using solid state molecular structures, photophysical data, cyclic voltammetry, DFT and LR‐TDDFT calculations, we compare o‐carborane and B(mes)2 (mes = 2,4,6‐Me3C6H2) as acceptor groups. Whereas the π‐acceptor strength of B(mes)2 is sufficient to drop the pyrene LUMO+1 below the LUMO, the carborane does not do this. We confirm the π‐donor strength of the julolidine‐like moiety, however, which raises the pyrene HOMO‐1 above the HOMO. In contrast to the analogous pyrene‐2‐yl‐o‐carborane, 2‐(1‐1,2‐dicarbadodecaboranyl(12))‐pyrene VI, which exhibits dual fluorescence, because the rate of internal conversion between locally‐excited (LE) and charge transfer (CT) (from the pyrene to the carborane) states is faster than the radiative decay rate, leading to a thermodynamic equilibrium between the 2 states, 4 shows only single fluorescence, as the CT state involving the carborane as the acceptor moiety in not kinetically accessible, so a more localized CT emission involving the julolidine‐like pyrene moiety is observed.

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Section: Introductionmentioning

confidence: 99%

Synthesis, Photophysical and Electronic Properties of a D‐π‐A Julolidine‐Like Pyrenyl‐o‐Carborane

Krebs,

Brändler,

Krummenacher

et al. 2024

Chemistry A European J

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“…DM can lead to changes in transcriptional networks, loss of mitochondrial homeostasis, inflammation, production of reactive oxygen species (ROS), and cell senescence (7,16,20,21,30,32,66,78,79,90,91,108,174,178,193,194,(201)(202)(203). ROS that are generated during oxidative stress include hydrogen peroxide, superoxide free radicals, nitric oxide, singlet oxygen, and peroxynitrite (36,37,65,90,96,113,120,137,154,180,186,(204)(205)(206)(207)(208)(209)(210)(211)(212)(213)(214)(215)(216)(217)(218). During conditions that oversee the detrimental effects of ROS, antioxidant systems are in play that involve glutathione peroxidase, catalase, superoxide dismutase, and the nutrient vitamins B, K, E, D, and C (20,34,42,47,53,100,132,186,…”

Section: Introductionmentioning

confidence: 99%

The impact of aging and oxidative stress in metabolic and nervous system disorders: programmed cell death and molecular signal transduction crosstalk

Maiese

2023

Front. Immunol.

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Life expectancy is increasing throughout the world and coincides with a rise in non-communicable diseases (NCDs), especially for metabolic disease that includes diabetes mellitus (DM) and neurodegenerative disorders. The debilitating effects of metabolic disorders influence the entire body and significantly affect the nervous system impacting greater than one billion people with disability in the peripheral nervous system as well as with cognitive loss, now the seventh leading cause of death worldwide. Metabolic disorders, such as DM, and neurologic disease remain a significant challenge for the treatment and care of individuals since present therapies may limit symptoms but do not halt overall disease progression. These clinical challenges to address the interplay between metabolic and neurodegenerative disorders warrant innovative strategies that can focus upon the underlying mechanisms of aging-related disorders, oxidative stress, cell senescence, and cell death. Programmed cell death pathways that involve autophagy, apoptosis, ferroptosis, and pyroptosis can play a critical role in metabolic and neurodegenerative disorders and oversee processes that include insulin resistance, β-cell function, mitochondrial integrity, reactive oxygen species release, and inflammatory cell activation. The silent mating type information regulation 2 homolog 1 (Saccharomyces cerevisiae) (SIRT1), AMP activated protein kinase (AMPK), and Wnt1 inducible signaling pathway protein 1 (WISP1) are novel targets that can oversee programmed cell death pathways tied to β-nicotinamide adenine dinucleotide (NAD+), nicotinamide, apolipoprotein E (APOE), severe acute respiratory syndrome (SARS-CoV-2) exposure with coronavirus disease 2019 (COVID-19), and trophic factors, such as erythropoietin (EPO). The pathways of programmed cell death, SIRT1, AMPK, and WISP1 offer exciting prospects for maintaining metabolic homeostasis and nervous system function that can be compromised during aging-related disorders and lead to cognitive impairment, but these pathways have dual roles in determining the ultimate fate of cells and organ systems that warrant thoughtful insight into complex autofeedback mechanisms.

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Targeting Specific Barriers

Langel

2023

CPP, Cell-Penetrating Peptides

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A new mitochondrial probe combining pyrene and a triphenylphosphonium salt for cellular oxygen and free radical detection via fluorescence lifetime measurements

Cited by 8 publications

References 60 publications

Synthesis, Photophysical and Electronic Properties of a D‐π‐A Julolidine‐Like Pyrenyl‐o‐Carborane

Synthesis, Photophysical and Electronic Properties of a D‐π‐A Julolidine‐Like Pyrenyl‐o‐Carborane

The impact of aging and oxidative stress in metabolic and nervous system disorders: programmed cell death and molecular signal transduction crosstalk

Targeting Specific Barriers

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