Visible and NIR light photoactivatable<i>o</i>-hydroxycinnamate system for efficient drug release with fluorescence monitoring

Gupta, Ajay; Singh, Neelu; Gautam, Aryan; Dhakar, Neetesh; Kumar, Sunil; Sasmal, Pijus K.

doi:10.1039/d2md00438k

Cited by 5 publications

(1 citation statement)

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“…The maximum absorption wavelength was slightly redshifted and the photolysis efficiency was improved by introducing electron donor groups. [79] Near-infrared light has a low destructive effect on living cells and tissues, making coumarin suitable for in vivo applications. [80] Reproduced with permission.…”

Section: Photo-degradable Hydrogelsmentioning

confidence: 99%

Photo‐Controllable Smart Hydrogels for Biomedical Application: A Review

Zhao,

Ran,

Lee

et al. 2023

Small Methods

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Nowadays, smart hydrogels are being widely studied by researchers because of their advantages such as simple preparation, stable performance, response to external stimuli, and easy control of response behavior. Photo‐controllable smart hydrogels (PCHs) are a class of responsive hydrogels whose physical and chemical properties can be changed when stimulated by light at specific wavelengths. Since the light source is safe, clean, simple to operate, and easy to control, PCHs have broad application prospects in the biomedical field. Therefore, this review timely summarizes the latest progress in the PCHs field, with an emphasis on the design principles of typical PCHs and their multiple biomedical applications in tissue regeneration, tumor therapy, antibacterial therapy, diseases diagnosis and monitoring, etc. Meanwhile, the challenges and perspectives of widespread practical implementation of PCHs are presented in biomedical applications. This study hopes that PCHs will flourish in the biomedical field and this review will provide useful information for interested researchers.

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Section: Photo-degradable Hydrogelsmentioning

confidence: 99%

Photo‐Controllable Smart Hydrogels for Biomedical Application: A Review

Zhao,

Ran,

Lee

et al. 2023

Small Methods

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Development of Cyclometalated Iridium(III) Complexes of 2‐Phenylbenzimidazole and Bipyridine Ligands for Selective Elimination of Gram‐Positive Bacteria

Gautam,

Gupta,

Prasad

et al. 2024

Chemistry An Asian Journal

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Herein, we have reported a series of cationic aggregation‐induced emission (AIE) active iridium(III) complexes (Ir1‐Ir5) of the type [Ir(C^N)2(N^N)]Cl, wherein C^N is a cyclometalating 2‐phenylbenzimidazole ligand with varying alkyl chain lengths and N^N is a 2,2ˊ‐bipyridine ligand attached to bis‐polyethylene glycol chains, for the treatment of bacterial infections. The AIE phenomenon of the complexes leveraged for detecting bacteria by fluorescence microscopy imaging that displayed a strong red emission in Gram‐positive bacteria. The antibacterial activity of the complexes assessed against Gram‐positive methicillin‐sensitive S. aureus, methicillin‐resistant S. aureus, E.faecium and E.faecalis and Gram‐negative E. coli and P.aeruginosa bacteria of clinical interest. The complexes Ir2‐Ir4 exerted potent antibacterial activity towards Gram‐positive strains with low minimum inhibitory concentrations (MICs) values in the range of 1−9 μM, which is comparable to clinically approved antibiotic vancomycin. In contrast, these complexes were found to be inactive towards Gram‐negative bacterial strains (MICs > 100 µM). The mechanism of antibacterial activity of the complexes implies that ROS generation, membrane depolarization and rupture are responsible for bacterial cell death. Further, the complexes Ir1‐Ir3 were found to be low‐toxic against human red blood cells and human embryonic kidney (HEK293) cells, indicating their potential for use as antibacterial agents.

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Revisiting the Chemistry and Photophysics of 3‐(N‐Methylpyridinium‐4‐yl)Coumarins for Designing “Covalent‐Assembly” and “Molecular Disassembly” Fluorescent Probes**

Gaumerd,

Renault,

Renard

et al. 2024

ChemPhotoChem

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The constant need for high‐performance aniline‐ or phenol‐based fluorophores suitable for the construction of activity‐based fluorescent probes, led us to study both synthesis and photophysics of C3‐N‐methylpyridinium‐4‐yl substituted 7‐(dialkylamino)/7‐hydroxycoumarins. Indeed, in the field of photoactive organic molecules, the positively charged N‐alkylpyridinium‐4‐yl groups are often used as acceptor units to dramatically impact spectral features through promoting intramolecular charge transfer (ICT) processes. They are also known as effective water‐solubilizing and mitochondria targeting moieties. The poor fluorescence efficiency of cationic 7‐hydroxycoumarin derivatives in aqueous physiological conditions was highlighted and rationalized by the predominance of a neutral quinonoid form in such buffer medium. The ability of the excited singlet state (S1) of this neutral species to undergo intersystem crossing (ISC) to triplet state (T1) was partly supported by phosphorescence measurements of singlet oxygen. We also took advantage of green‐emissive properties of 7‐(diethylamino)‐3‐(N‐methylpyridinium‐4‐yl)coumarin to successfully design and validate a novel small‐molecule fluorescent probe for the detection of alkaline phosphatase (ALP), based on the "covalent‐assembly" principle. A practical use of ortho‐formylated 7‐hydroxy‐3‐(N‐methylpyridinium‐4‐yl)coumarin was next considered with the synthesis of a Fe(III)‐salen complex whose the potential as a "molecular disassembly" probe for fluorogenic sensing of pyrophosphate (PPi) anion was assessed.

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Visible and NIR light photoactivatableo-hydroxycinnamate system for efficient drug release with fluorescence monitoring

Abstract: Photoactivatable protecting groups (PPGs) have become the powerful materials for controlling the activity of biologically important molecules in biomedical field. However, designing PPG that can be efficiently activated by biologically...

Cited by 5 publications

References 49 publications

Photo‐Controllable Smart Hydrogels for Biomedical Application: A Review

Photo‐Controllable Smart Hydrogels for Biomedical Application: A Review

Development of Cyclometalated Iridium(III) Complexes of 2‐Phenylbenzimidazole and Bipyridine Ligands for Selective Elimination of Gram‐Positive Bacteria

Revisiting the Chemistry and Photophysics of 3‐(N‐Methylpyridinium‐4‐yl)Coumarins for Designing “Covalent‐Assembly” and “Molecular Disassembly” Fluorescent Probes**

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