Chemistry and biology of manganese carbon-releasing molecules containing thiosemicarbazone ligands

Daniels, Hannah G.; Fast, Olivia G; Shell, Steven M.; Beckford, Floyd A.

doi:10.1016/j.jphotochem.2019.01.037

Cited by 13 publications

(5 citation statements)

References 67 publications

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“…172 Four Mn(I) photoCORMs, 13a-13d (Figure 3), containing 6nitro-piperonal thiosemicarbazone ligands, were found to have both antibacterial and cytotoxic characteristics. 173 The photoCORMs were categorized as fast CO releasers. When exposed to a UV/Vis light source (365 (UV), 405 (purple) and 435 (blue) nm), the CO release t1/2 values were between 11 and 95 s. While the purple and blue lights caused the release of around 1.5 and 1.0 equivalents of CO, respectively, the UV-light produced two equivalents of CO. PhotoCORMs 13a-13d and their iCORMs, exhibited dose-dependent cytotoxicity against A549 as well as normal HEK-293T cell lines.…”

Section: Manganese(i) Cormsmentioning

confidence: 99%

“…The results imply that some CORMs have cytotoxic effects on HEK-293T, but that CO release from these molecules is not the only toxic mechanism. 173 As a continuation of their efforts on finding the appropriate Mn(I) photoCORMs with desirable properties for the clinical applications, Mascharak and co-workers synthesized two visible light-activated luminescent photoCORMs, 14 and 15 (Figure 4), functionalized with diazabutadiene ligand. 174 For 24 h, 14 showed good stability in 2% (CH3OH/H2O) mixture as well as CH2Cl2 and CHCl3.…”

Section: Manganese(i) Cormsmentioning

confidence: 99%

“…The results imply that some CORMs have cytotoxic effects on HEK-293T, but that CO release from these molecules is not the only toxic mechanism. 175…”

Section: Next Generation Cormsmentioning

confidence: 99%

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Metal-based carbon monoxide releasing molecules with promising cytotoxic properties

Mansour,

Khaled,

Ferraro

et al. 2024

Dalton Trans.

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Section: Manganese(i) Cormsmentioning

confidence: 99%

Section: Manganese(i) Cormsmentioning

confidence: 99%

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Metal-based carbon monoxide releasing molecules with promising cytotoxic properties

Mansour,

Khaled,

Ferraro

et al. 2024

Dalton Trans.

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“…Initial efforts include those of Motterlini and Mann by using CO-immobilized on a metal center as CO-releasing molecules (CORMs) as well as using Hb as a carrier (Motterlini et al, 2002;Motterlini and Otterbein, 2010;Mann, 2012;Garc ıa-Gallego and Bernardes, 2014;Heinemann et al, 2014). Later efforts by others expanded to CORMs capable of triggered release of CO by light (Niesel et al, 2008;Jackson et al, 2011;Jimenez et al, 2016;Daniels et al, 2019;Kawahara et al, 2019a) and enzyme (Romanski et al, 2011;Sitnikov et al, 2015); encapsulated or conjugated CORMs to minimize metal exposure (Br€ uckmann et al, 2011;Steiger et al, 2016Steiger et al, , 2017Wollborn et al, 2018); and organic CORMs, which are photo-sensitive (Poloukhtine and Popik, 2006;Antony et al, 2013;Peng et al, 2013;Palao et al, 2016;Fig. 2.…”

Section: General Considerations In Examining the Molecular Targets Of Comentioning

confidence: 99%

Carbon Monoxide Signaling: Examining Its Engagement with Various Molecular Targets in the Context of Binding Affinity, Concentration, and Biologic Response

et al. 2022

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Carbon monoxide (CO) has been firmly established as an endogenous signaling molecule with a variety of pathophysiological and pharmacological functions, including immunomodulation, organ protection, and circadian clock regulation, among many others. In terms of its molecular mechanism(s) of action, CO is known to bind to a large number of hemoproteins with at least 25 identified targets, including hemoglobin, myoglobin, neuroglobin, cytochrome c oxidase, cytochrome P450, soluble guanylyl cyclase, myeloperoxidase, and some ion channels with dissociation constant values spanning the range of sub-nM to high lM. Although CO's binding affinity with a large number of targets has been extensively studied and firmly established, there is a pressing need to incorporate such binding information into the analysis of CO's biologic response in the context of affinity and dosage. Especially important is to understand the reservoir role of hemoglobin in CO storage, transport, distribution, and transfer. We critically review the literature and inject a sense of quantitative assessment into our analyses of the various relationships among binding affinity, CO concentration, target occupancy level, and anticipated pharmacological actions. We hope that this review presents a picture of the overall landscape of CO's engagement with various targets, stimulates additional research, and helps to move the CO field in the direction of examining individual targets in the context of all of the targets and the concentration of available CO. We believe that such work will help the further understanding of the relationship of CO concentration and its pathophysiological functions and the eventual development of CO-based therapeutics.-Significance Statement--The further development of carbon monoxide (CO) as a therapeutic agent will significantly rely on the understanding of CO's engagement with therapeutically relevant targets of varying affinity. This review critically examines the literature by quantitatively analyzing the intricate relationships among targets, target affinity for CO, CO level, and the affinity state of carboxyhemoglobin and provide a holistic approach to examining the molecular mechanism(s) of action for CO.

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“…However, the most commonly used stimulus to turn on CO release is light. Many photosensitive metal carbonyl complexes were studied to this end. − Despite significant developments, stimuli-responsive CORMs for biological applications and allosteric regulation/activation for CO release are not known.…”

Section: Introductionmentioning

confidence: 99%

Allosteric Regulation in Carbon Monoxide (CO) Release: Anion Responsive CO-Releasing Molecule (CORM) Derived from (Terpyridine)phenol Manganese Tricarbonyl Complex with Colorimetric and Fluorescence Monitoring

et al. 2019

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A new CO-releasing terpyridine based manganese(I) tricarbonyl complex, [MnBr(CO)3(terpy-C6H4OH)] (1·Mn-OH) functioning via light has been reported. For the first time, we have demonstrated the allosteric regulation concept to control the CO-releasing properties of a CO-releasing molecule (CORM). Fluoride ion is reported to function as an allosteric activator to control the rate of CO release in the CORM. Complex 1·Mn-OH represents an interesting new class of CO-releasing system that releases CO upon irradiation with blue light (410 nm) over a period of 40 min with the half-time of 9.8 min. Fluoride ion selectively binds to the phenol moiety of the complex through hydrogen bonding and deprotonates to phenolate with a color change. Interestingly in the presence of fluoride ion, the rate of CO release is fast with the half-time of less than a minute. The rate of CO release is allosterically regulated by fluoride anion and can be monitored through a color change, fluorescence, and absorption based spectral changes along with IR studies and myoglobin assay.

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Chemistry and biology of manganese carbon-releasing molecules containing thiosemicarbazone ligands

Cited by 13 publications

References 67 publications

Metal-based carbon monoxide releasing molecules with promising cytotoxic properties

Metal-based carbon monoxide releasing molecules with promising cytotoxic properties

Carbon Monoxide Signaling: Examining Its Engagement with Various Molecular Targets in the Context of Binding Affinity, Concentration, and Biologic Response

Allosteric Regulation in Carbon Monoxide (CO) Release: Anion Responsive CO-Releasing Molecule (CORM) Derived from (Terpyridine)phenol Manganese Tricarbonyl Complex with Colorimetric and Fluorescence Monitoring

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