3-Hydroxyflavones and 3-Hydroxy-4-oxoquinolines as Carbon Monoxide-Releasing Molecules

Soboleva, Tatiana; Berreau, Lisa M.

doi:10.3390/molecules24071252

Cited by 39 publications

(36 citation statements)

References 126 publications

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“…9-(Diethylamino)-3-methoxy-5H-benzo[a]phenoxazin-5-one (15). The compound was synthesized according to a literature procedure.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

“…It has been evidenced that CO is biologically relevant; it exhibits antiapoptotic, anti-inflammatory, antiproliferative, and anticoagulation effects − and prevention of tissue damage and cardiovascular pathology, although the mechanisms are still not well understood. To utilize these potentially chemopreventive and/or therapeutic effects, CO-releasing molecules (CORMs) have been developed as artificial tools to deliver therapeutic amounts of CO into the cell using various initiation approaches. ,− …”

Section: Introductionmentioning

confidence: 99%

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Structural Modifications of Nile Red Carbon Monoxide Fluorescent Probe: Sensing Mechanism and Applications

et al. 2020

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Carbon monoxide (CO) is a cell-signaling molecule (gasotransmitter) produced endogenously by oxidative catabolism of heme, and the understanding of its spatial and temporal sensing at the cellular level is still an open challenge. Synthesis, optical properties, and study of the sensing mechanism of Nile red Pd-based CO chemosensors, structurally modified by core and bridge substituents, in methanol and aqueous solutions are reported in this work. The sensing fluorescence "off−on" response of palladacycle-based sensors possessing low-background fluorescence arises from their reaction with CO to release the corresponding highly fluorescent Nile red derivatives in the final step. Our mechanistic study showed that electron-withdrawing and electron-donating core substituents affect the rate-determining step of the reaction. More importantly, the substituents were found to have a substantial effect on the Nile red sensor fluorescence quantum yields, hereby defining the sensing detection limit. The highest overall fluorescence and sensing rate enhancements were found for a 2-hydroxy palladacycle derivative, which was used in subsequent biological studies on mouse hepatoma cells as it easily crosses the cell membrane and qualitatively traces the localization of CO within the intracellular compartment with the linear quantitative response to increasing CO concentrations.

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“…9-(Diethylamino)-3-methoxy-5H-benzo[a]phenoxazin-5-one (15). The compound was synthesized according to a literature procedure.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Structural Modifications of Nile Red Carbon Monoxide Fluorescent Probe: Sensing Mechanism and Applications

et al. 2020

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“…11,14 Rational design of such photoactivatable CORMs (photoCORMs), based on, for example, xanthene 14 or BODIPY moieties, 40 allowed for fine-tuning of their optical and chemical properties. The bathochromic shift of absorption spectra toward the visible and nearinfrared region (i.e., a phototherapeutic window), [41][42][43] is especially important for bioapplications. The potential therapeutic use of photoCORMs depends on the same legal and economic considerations as for other drugs.…”

Section: Introductionmentioning

confidence: 99%

Photochemistry of Common Xanthene Fluorescent Dyes as Efficient Visible-light Activatable CO-Releasing Molecules

Martínek

Ludvíková

Šranková

et al. 2022

Preprint

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Xanthene derivatives are organic dyes, some of which are routinely used in different chemical and biological applications, including human medicine. In this work, we investigated the photochemistry of some of the most common ones, fluorescein, eosin Y, and rose bengal, and major products of their photodegradation using optical spectroscopy, NMR, chromatography and mass spectroscopy techniques. These substances, usually considered (photo)chemically stable, were found to liberate carbon monoxide (CO) in 40–80% chemical yields upon extensive irradiation with visible light in aqueous solutions during their multistep concomitant degradation processes. In addition, a number of low-mass secondary photoproducts, such as phthalic and formic acids, were identified in the irradiated mixtures. We demonstrate that these common fluorescent dyes can also be considered as visible-light activatable carbon monoxide (CO)-releasing molecules (photoCORMs) under specific conditions with potential biological implications.

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“…One key obstacle in developing CO‐based therapeutics is the difficulty in its controlled delivery because inhalation of gaseous CO does not allow easy control of quantity and risk factors 134,135 . Therefore, there has been much interest in developing CO‐releasing molecules (CO‐RMs) 135–137 and recently CO prodrugs for controlled delivery via oral or parenteral administration 124,138 . Aiming for developing controlled CO delivery methods, an enrichment‐triggered method was used to target the mitochondrion, which is the site of action for CO.…”

Section: Enrichment‐triggered Drug Releasementioning

confidence: 99%

Making smart drugs smarter: The importance of linker chemistry in targeted drug delivery

Yang

Pan

Choudhury

et al. 2020

Medicinal Research Reviews

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Smart drugs, such as antibody-drug conjugates, for targeted therapy rely on the ability to deliver a warhead to the desired location and to achieve activation at the same site. Thus, designing a smart drug often requires proper linker chemistry for tethering the warhead with a vehicle in such a way that either allows the active drug to retain its potency while being tethered or ensures release and thus activation at the desired location. Recent years have seen much progress in the design of new linker activation strategies. Herein, we review the recent development of chemical strategies used to link the warhead with a delivery vehicle for preferential cleavage at the desired sites. K E Y W O R D S antibody-drug conjugates, click and release, drug delivery, linker chemistry, targeted delivery, triggered release 1 | INTRODUCTION In the world of drug discovery and development, the concept of "smart drugs" broadly refers to those that can selectively affect disease-relevant target(s). However, to a certain degree, essentially all drugs are already selective toward the desired target(s) whether they are enzyme inhibitors, receptor ligands, ion channel blockers, inhibitors of protein-protein interaction, or even genotoxins used for cancer chemotherapy, among others. They would not have made through the various milestones of drug discovery and developmental processes if they were not sufficiently selective for the intended target(s). However, once administered into the human body, the highly complex living system often leads to many unexpected off-target effects. Thus, various additional approaches have been studied and

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3-Hydroxyflavones and 3-Hydroxy-4-oxoquinolines as Carbon Monoxide-Releasing Molecules

Cited by 39 publications

References 126 publications

Structural Modifications of Nile Red Carbon Monoxide Fluorescent Probe: Sensing Mechanism and Applications

Structural Modifications of Nile Red Carbon Monoxide Fluorescent Probe: Sensing Mechanism and Applications

Photochemistry of Common Xanthene Fluorescent Dyes as Efficient Visible-light Activatable CO-Releasing Molecules

Making smart drugs smarter: The importance of linker chemistry in targeted drug delivery

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