Photooxidation of Alkaloids: Considerable Quantum Yield Enhancement by Rose Bengal‐sensitized Singlet Molecular Oxygen Generation

Görner, Helmut; Miskolczy, Zsombor; Megyesi, Mónika; Biczók, László

doi:10.1111/j.1751-1097.2011.00994.x

Cited by 17 publications

(4 citation statements)

References 40 publications

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“… The 1 O 2 , and subsequently O 2 •– , appeared to be powerful, selective, and efficient oxidizing reagents for tertiary amines and particularly for fragile alkaloids. The studies on 1 O 2 and O 2 •– have received substantial attention because of their role in photosensitized oxidation reactions. − In biological systems containing polar aqueous media, the single-electron-transfer processes are expected to have a crucial role in the interaction of electron-rich substrates with 1 O 2 …”

Section: Generation Of the Superoxide Ionmentioning

confidence: 99%

Superoxide Ion: Generation and Chemical Implications

Hayyan¹,

Hashim²,

AlNashef³

2016

Chem. Rev.

1,718

1,058

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Superoxide ion (O2(•-)) is of great significance as a radical species implicated in diverse chemical and biological systems. However, the chemistry knowledge of O2(•-) is rather scarce. In addition, numerous studies on O2(•-) were conducted within the latter half of the 20th century. Therefore, the current advancement in technology and instrumentation will certainly provide better insights into mechanisms and products of O2(•-) reactions and thus will result in new findings. This review emphasizes the state-of-the-art research on O2(•-) so as to enable researchers to venture into future research. It comprises the main characteristics of O2(•-) followed by generation methods. The reaction types of O2(•-) are reviewed, and its potential applications including the destruction of hazardous chemicals, synthesis of organic compounds, and many other applications are highlighted. The O2(•-) environmental chemistry is also discussed. The detection methods of O2(•-) are categorized and elaborated. Special attention is given to the feasibility of using ionic liquids as media for O2(•-), addressing the latest progress of generation and applications. The effect of electrodes on the O2(•-) electrochemical generation is reviewed. Finally, some remarks and future perspectives are concluded.

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Section: Generation Of the Superoxide Ionmentioning

confidence: 99%

Superoxide Ion: Generation and Chemical Implications

Hayyan¹,

Hashim²,

AlNashef³

2016

Chem. Rev.

1,718

1,058

View full text Add to dashboard Cite

show abstract

“…BBR is a weak PS in water, but in non-polar environments, it can produce both 1 O 2 and radical species. It is proven that BBR is more prone to photochemical reactions in non-polar solvents than in polar solvents; also, the ROS yield is higher in non-polar solvents [ 108 , 118 ], and the quantum yield of BBR-sensitized oxidation increases with an increase in pH [ 119 ]. Other reactions upon laser irradiation of BBR exist besides photooxidation processes, including photoionization and photoexcitation of BBR in N 2 and O 2 -saturated systems [ 108 , 111 ].…”

Section: Berberine’s Potential As a Bioactive Moleculementioning

confidence: 99%

Elucidating Berberine’s Therapeutic and Photosensitizer Potential through Nanomedicine Tools

Marques,

Fernandes,

Lima

2023

Pharmaceutics

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Berberine, an isoquinoline alkaloid extracted from plants of the Berberidaceae family, has been gaining interest due to anti-inflammatory and antioxidant activities, as well as neuro and cardiovascular protective effects in animal models. Recently, photodynamic therapy demonstrated successful application in many fields of medicine. This innovative, non-invasive treatment modality requires a photosensitizer, light, and oxygen. In particular, the photosensitizer can selectively accumulate in diseased tissues without damaging healthy cells. Berberine’s physicochemical properties allow its use as a photosensitising agent for photodynamic therapy, enabling reactive oxygen species production and thus potentiating treatment efficacy. However, berberine exhibits poor aqueous solubility, low oral bioavailability, poor cellular permeability, and poor gastrointestinal absorption that hamper its therapeutic and photodynamic efficacy. Nanotechnology has been used to minimize berberine’s limitations with the design of drug delivery systems. Different nanoparticulate delivery systems for berberine have been used, as lipid-, inorganic- and polymeric-based nanoparticles. These berberine nanocarriers improve its therapeutic properties and photodynamic potential. More specifically, they extend its half-life, increase solubility, and allow a high permeation and targeted delivery. This review describes different nano strategies designed for berberine delivery as well as berberine’s potential as a photosensitizer for photodynamic therapy. To benefit from berberine’s overall potential, nanotechnology has been applied for berberine-mediated photodynamic therapy.

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“… a : in DMSO, b : in H 2 O, c : in benzene, d : in MeCN, e : in dioxane, f : in dichloromethane, g : in DMF. Data obtained in references [ 86 , 87 , 88 , 91 , 92 , 93 , 95 , 99 , 100 , 101 , 102 ]. …”

Section: Figures Scheme and Tablesmentioning

confidence: 99%

Alkaloids as Photosensitisers for the Inactivation of Bacteria

et al. 2021

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Antimicrobial photodynamic therapy has emerged as a powerful approach to tackle microbial infections. Photodynamic therapy utilises a photosensitiser, light, and oxygen to generate singlet oxygen and/or reactive oxygen species in an irradiated tissue spot, which subsequently react with nearby biomolecules and destroy the cellular environment. Due to the possibility to irradiate in a very precise location, it can be used to eradicate bacteria, fungus, and parasites upon light activation of the photosensitiser. In this regard, natural products are low-cost molecules capable of being obtained in large quantities, and some of them can be used as photosensitisers. Alkaloids are the largest family among natural products and include molecules with a basic nature and aromatic rings. For this study, we collected the naturally occurring alkaloids used to treat microorganism infections using a photodynamic inactivation approach. We gathered their main photophysical properties (excitation/emission wavelengths, quantum yields, and oxygen quantum yield) which characterise the ability to efficiently photosensitise. In addition, we described the antibacterial activity of alkaloids upon irradiation and the mechanisms involved in the microorganism killing. This review will serve as a reference source to obtain the main information on alkaloids used in antimicrobial photodynamic therapy.

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Photooxidation of Alkaloids: Considerable Quantum Yield Enhancement by Rose Bengal‐sensitized Singlet Molecular Oxygen Generation

Cited by 17 publications

References 40 publications

Superoxide Ion: Generation and Chemical Implications

Superoxide Ion: Generation and Chemical Implications

Elucidating Berberine’s Therapeutic and Photosensitizer Potential through Nanomedicine Tools

Alkaloids as Photosensitisers for the Inactivation of Bacteria

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