Ruthenium imidazole oxime carbonyls and their activities as CO-releasing molecules

Oresmaa, Larisa; Tarvainen, Heli; Machal, Kalle; Haukka, Matti

doi:10.1039/c2dt31002c

Cited by 14 publications

(18 citation statements)

References 34 publications

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“…171 The mechanisms of CO release from ruthenium(II)-based CORMs with methoxycarbonyl or ethoxycarbonyl ligands are also known. 172 Whereas in this example the oxidation state of Ru remained 2+, transition metals can adopt several stable oxidation states and the CO release properties may interfere with the redox chemistry of these metals in aqueous solution. Mann already mentioned that CORMs might be able to catalyze Fenton-type reactions leading to the formation of ROS.…”

Section: Controlled Release Of Comentioning

confidence: 99%

Carbon monoxide – physiology, detection and controlled release

et al. 2014

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Carbon monoxide (CO) is increasingly recognized as a cell-signalling molecule akin to nitric oxide (NO). CO has attracted particular attention as a potential therapeutic agent because of its reported anti-hypertensive, anti-inflammatory and cell-protective effects. We discuss recent progress in identifying new effector systems and elucidating the mechanisms of action of CO on, e.g., ion channels, as well as the design of novel methods to monitor CO in cellular environments. We also report on recent developments in the area of CO-releasing molecules (CORMs) and materials for controlled CO application. Novel triggers for CO release, metal carbonyls and degradation mechanisms of CORMs, are highlighted. In addition, potential formulations of CORMs for targeted CO release are discussed.

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Section: Controlled Release Of Comentioning

confidence: 99%

Carbon monoxide – physiology, detection and controlled release

et al. 2014

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“…From the temperature-variable kinetic measurements, an activation energy of 78 kJ mol −1 was determined for the CO release from the IONPsurface-bound CORM-3 analog in the alginate@dextran polymer shell. 66 In a follow-up study, oxime-based CORMs 69 were similarly covalently immobilized on IONPs, followed by the oximeCORM@IONP encapsulation in dextran and alginate (Fig. 22).…”

Section: Covalently-bound Corm Conjugates In Combination With Encapsumentioning

confidence: 99%

CO-releasing molecule (CORM) conjugate systems

2016

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The development of CORMs (CO-releasing molecules) as a prodrug for CO administration in living organisms has attracted significant attention. CORMs offer the promising possibility of a safe and controllable release of CO in low amounts triggered by light, ligands, enzymes, etc. For the targeting of specific tissues or diseases and to prevent possible side effects from metals and other residues after CO release, these CORMs are attached to biocompatible systems, like peptides, polymers, nanoparticles, dendrimers, protein cages, non-wovens, tablets, and metal-organic frameworks. We discuss in this review the known CORM carrier conjugates, in short CORM conjugates, with covalently-bound or incorporated CORMs for medicinal and therapeutic applications. Most conjugates are nontoxic, show increasing half-lives of CO release, and make use of the EPR-effect, but still show problems because of a continuous background of CO release and the absence of an on/off-switch for the CO release.

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“…The chemistry and pharmacological properties of these compounds is becoming a topic of great interest since in the last 2-3 years other research groups have synthesized a variety of different new CO-RMs. Recently ruthenium imidazole oxime carbonyls [62], photoactive and nanoCO-RMs [63,64], enzyme-triggered CO-RMs [65], CO-RMs encapsulated in micelles [66] and rhenium-based CO-RMs [67] have been developed. However, for most of these new molecules a detailed picture of their behaviour in cells, tissues and in vivo models of disease is not yet available, and will be required to evaluate their full pharmacological potential.…”

Section: Introductionmentioning

confidence: 99%

Emerging concepts on the anti-inflammatory actions of carbon monoxide-releasing molecules (CO-RMs)

2012

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Carbon monoxide-releasing molecules (CO-RMs) are a class of organometallo compounds capable of delivering controlled quantities of CO gas to cells and tissues thus exerting a broad spectrum of pharmacological effects. CO-RMs containing transition metal carbonyls were initially implemented to mimic the function of heme oxygenase-1 (HMOX1), a stress inducible defensive protein that degrades heme to CO and biliverdin leading to anti-oxidant and anti-inflammatory actions. Ten years after their discovery, the research on the chemistry and biological activities of CO-RMs has greatly intensified indicating that their potential use as CO delivering agents for the treatment of several pathological conditions is feasible. Although CO-RMs are a class of compounds that structurally diverge from traditional organic-like pharmaceuticals, their behaviour in the biological environments is progressively being elucidated revealing interesting features of metal-carbonyl chemistry towards cellular targets. Specifically, the presence of carbonyl groups bound to transition metals such as ruthenium, iron or manganese appears to make CO-RMs unique in their ability to transfer CO intracellularly and amplify the mechanisms of signal transduction mediated by CO. In addition to their well-established vasodilatory activities and protective effects against organ ischemic damage, CO-RMs are emerging for their striking anti-inflammatory properties which may be the result of the multiple activities of metal carbonyls in the control of redox signaling, oxidative stress and cellular respiration. Here, we review evidence on the pharmacological effects of CO-RMs in models of acute and chronic inflammation elaborating on some emerging concepts that may help to explain the chemical reactivity and mechanism(s) of action of this distinctive class of compounds in biological systems.

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Ruthenium imidazole oxime carbonyls and their activities as CO-releasing molecules

Cited by 14 publications

References 34 publications

Carbon monoxide – physiology, detection and controlled release

Carbon monoxide – physiology, detection and controlled release

CO-releasing molecule (CORM) conjugate systems

Emerging concepts on the anti-inflammatory actions of carbon monoxide-releasing molecules (CO-RMs)

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