Aromatic Ketones as Photocatalysts: Combined Action as Triplet Photosensitiser and Ground State Electron Acceptor

Pérez‐Prieto, Julia; Galian, Raquel E.; Morant‐Miñana, Maria C.

doi:10.1002/cphc.200600328

Cited by 6 publications

(2 citation statements)

References 19 publications

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“…To understand the discrepancy better, we analyzed the structures of the seven compounds that could not be confirmed by the BODIPY-prazosin assay. Metyrapone, acepromazine, piperacetazine and acetophenazine have an aromatic ketone functional group, which can act as an electron acceptor and deactivate the singlet state of BODIPY via an intermolecular electron-transfer process (30), (31). Porphyrin in verteporin and benzopteridine in riboflavin can quench the fluorescence of BODIPY by way of photoinduced electron transfer (32) (33).…”

Section: Discussionmentioning

confidence: 99%

Identification of Inhibitors of ABCG2 by a Bioluminescence Imaging–Based High-Throughput Assay

et al. 2009

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ABCG2 is a member of the ATP-binding cassette (ABC) family of transporters, the overexpression of which is associated with tumor resistance to a variety of chemotherapeutic agents. Accordingly, combining ABCG2 inhibitor(s) with chemotherapy has the potential to improve treatment outcome. To search for clinically useful ABCG2 inhibitors, a bioluminescence imaging (BLI)-based assay was developed to allow highthroughput compound screening. This assay exploits our finding that D-luciferin, the substrate of firefly luciferase ( fLuc), is a specific substrate of ABCG2, and ABCG2 inhibitors block the export of D-luciferin and enhance bioluminescence signal by increasing intracellular D-luciferin concentrations. HEK293 cells, engineered to express ABCG2 and fLuc, were used to screen the Hopkins Drug Library that includes drugs approved by the Food and Drug Administration (FDA) as well as drug candidates that have entered phase II clinical trials. Forty-seven compounds showed BLI enhancement, a measure of anti-ABCG2 activity, of z5-fold, the majority of which were not previously known as ABCG2 inhibitors. The assay was validated by its identification of known ABCG2 inhibitors and by confirming previously unknown ABCG2 inhibitors using established in vitro assays (e.g., mitoxantrone resensitization and BODIPY-prazosin assays). Glafenine, a potent new inhibitor, also inhibited ABCG2 activity in vivo. The BLI-based assay is an efficient method to identify new inhibitors of ABCG2. As they were derived from a FDA-approved compound library, many of the inhibitors uncovered in this study are ready for clinical testing.

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Section: Discussionmentioning

confidence: 99%

Identification of Inhibitors of ABCG2 by a Bioluminescence Imaging–Based High-Throughput Assay

et al. 2009

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“…It is affordable, readily available, and has shown many practical photochemical transformations. Yet, its application is largely confined to excess loading and diminished reactivity on a catalytic scale without the presence of a sacrificial reagent 32 , 33 . Therefore, the regeneration of ketones without stoichiometric loading of strong oxidants would be beneficial.…”

Section: Introductionmentioning

confidence: 99%

Acceptorless cross-dehydrogenative coupling for C(sp3)-H heteroarylation mediated by a heterogeneous GaN/ketone photocatalyst/photosensitizer system

Kang,

Tan,

Han

et al. 2023

Commun Chem

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Alkanes are naturally abundant chemical building blocks that contain plentiful C(sp3)-H bonds. While inert, the activation of C(sp3)-H via hydrogen atom abstraction (HAT) stages an appealing approach to generate alkyl radicals. However, prevailing shortcomings include the excessive use of oxidants and alkanes that impede scope. We herein show the use of gallium nitride (GaN) as a non-toxic, recyclable, heterogeneous photocatalyst to enable alkyl C(sp3)-H in conjunction with the catalytic use of simple photosensitizer, benzophenone, to promote the desired alkyl radical generation. The dual photocatalytic cycle enables cross-dehydrogenative Minisci alkylation under mild and chemical oxidant-free conditions.

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Taming of superacids: PVP-triflic acid as an effective solid triflic acid equivalent for Friedel–Crafts hydroxyalkylation and acylation

Prakash

Paknia

Kulkarni

et al. 2015

Journal of Fluorine Chemistry

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Aromatic Ketones as Photocatalysts: Combined Action as Triplet Photosensitiser and Ground State Electron Acceptor

Cited by 6 publications

References 19 publications

Identification of Inhibitors of ABCG2 by a Bioluminescence Imaging–Based High-Throughput Assay

Identification of Inhibitors of ABCG2 by a Bioluminescence Imaging–Based High-Throughput Assay

Acceptorless cross-dehydrogenative coupling for C(sp3)-H heteroarylation mediated by a heterogeneous GaN/ketone photocatalyst/photosensitizer system

Taming of superacids: PVP-triflic acid as an effective solid triflic acid equivalent for Friedel–Crafts hydroxyalkylation and acylation

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