Carbon monoxide – physiology, detection and controlled release

Heinemann, Stefan H.; Hoshi, Toshinori; Westerhausen, Matthias; Schiller, Alexander

doi:10.1039/c3cc49196j

Cited by 355 publications

(286 citation statements)

References 204 publications

(369 reference statements)

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“…There has therefore been significant effort to produce molecules which can release CO, so-called CORMs (carbon monoxide releasing molecules). [16][17][18][19][20] The majority of these systems are based around metal carbonyl fragments, which offer a direct route to the release of CO. Such organometallic therapeutics are unusual, and efforts have been made to exploit alternative CO sources.…”

Section: Introductionmentioning

confidence: 99%

PhotoCORMs: CO release moves into the visible

Wright

2016

Dalton Trans.

117

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The potential of carbon monoxide to act as a therapeutic agent is now well-established. Controlled delivery of CO is best achieved using 'CORMs': molecules which release known amounts of carbon monoxide in response to a stimulus. Metal carbonyl complexes will release CO if irradiated with ultraviolet light, but it is only in the past five years that development of true 'photoCORMs' has been explored. Recent exciting developments in this area now show that design of photoCORMs operating well into the visible region is achievable. In this Perspective, we examine the growth of photoCORMs from their origins in the photophysics of metal carbonyls to the latest visible-light agents.

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Section: Introductionmentioning

confidence: 99%

PhotoCORMs: CO release moves into the visible

Wright

2016

Dalton Trans.

117

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“…Transition metal carbonyl complexes are the most prominent CORMs because they can be triggered via light, solvent exchange on the metal coordination sphere, and enzymes (29,30). Macromolecular systems have also been exploited as CORM carriers to adapt CO release kinetics and retain toxic metabolites after CO release (27 (10,(31)(32)(33)(34). Besides inhibition of the respiratory chain, CORMs seem to also target other proteins, because the bactericidal effects were found under aerobic and anaerobic conditions (33,35).…”

Section: Discussionmentioning

confidence: 99%

“…For the controlled delivery and release of the toxic gas in aqueous environments, carbon monoxide-releasing molecules (CORMs) have proven to be the most promising for therapeutic usage (27,28). Transition metal carbonyl complexes are the most prominent CORMs because they can be triggered via light, solvent exchange on the metal coordination sphere, and enzymes (29,30).…”

Section: Discussionmentioning

confidence: 99%

Bactericidal Effect of a Photoresponsive Carbon Monoxide-Releasing Nonwoven against Staphylococcus aureus Biofilms

Klinger-Strobel

Gläser

Makarewicz

et al. 2016

Antimicrob Agents Chemother

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Staphylococcus aureus is a leading pathogen in skin and skin structure infections, including surgical and traumatic infections that are associated with biofilm formation. Because biofilm formation is accompanied by high phenotypic resistance of the embedded bacteria, they are almost impossible to eradicate by conventional antibiotics. Therefore, alternative therapeutic strategies are of high interest. We generated nanostructured hybrid nonwovens via the electrospinning of a photoresponsive carbon monoxide (CO)-releasing molecule [CORM-1, Mn 2 (CO) 10 ] and the polymer polylactide. This nonwoven showed a CO-induced antimicrobial activity that was sufficient to reduce the biofilm-embedded bacteria by 70% after photostimulation at 405 nm. The released CO increased the concentration of reactive oxygen species (ROS) in the biofilms, suggesting that in addition to inhibiting the electron transport chain, ROS might play a role in the antimicrobial activity of CORMs on S. aureus. The nonwoven showed increased cytotoxicity on eukaryotic cells after longer exposure, most probably due to the released lactic acid, that might be acceptable for local and short-time treatments. Therefore, CO-releasing nonwovens might be a promising local antimicrobial therapy against biofilm-associated skin wound infections. Staphylococcus aureus, both methicillin-resistant S. aureus (MRSA) and methicillin-susceptible S. aureus (MSSA), is the leading pathogen in skin and skin structure infections (SSSIs), including surgical and traumatic infections (1, 2). S. aureus has developed a highly effective mechanism to invade tissues and evade the immune system by biofilm formation and intracellular persistence. This can result in chronic and recurring SSSI, particularly in patients with comorbidities such as diabetes mellitus (e.g., diabetic foot syndrome). Noneradicable S. aureus SSSI can be the focus of S. aureus bacteremia, which has a mortality of up to 30% (3). In the United States, community-acquired MRSA has emerged as one of the leading causes of community-acquired SSSI (2).Biofilms are sessile matrix-embedded microbial communities that colonize nearly all artificial and natural surfaces. They are thought to be present in more than 80% of all nosocomial bacterial infections (4). Compared to their planktonic counterparts, bacteria embedded in a biofilm benefit from the protective properties of the matrix, conveying up to 1,000-fold-higher resistance to antibiotics (5). The enhanced phenotypic resistance (correctly termed tolerance) of biofilms is caused mainly by decreased growth rates and metabolically inactive persister cells (a protected phenotypic state) (6). Most antibiotics inhibit metabolic processes in the cell, such as replication (e.g., fluoroquinolones), transcription (e.g., rifampin) or translation (e.g., aminoglycosides and macrolides), and therefore they become ineffective in these persister cells. Altered microenvironments (7) and enzymes hydrolyzing or modifying the antimicrobials that are enriched within the matrix are additio...

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“…For soluble CORMs, low toxicity is required for the CORMs as well as for their degradation end-products after CO release. In all these manganese(I)-based CORMs, the metal centers show a low spin state in an octahedral environment with a d 6 configuration. During CO liberation, most commonly an oxidation to manganese(II) has been observed.…”

Section: Introductionmentioning

confidence: 99%

“…Metal carbonyls are usually considered for this purpose because numerous carbonyl ligands can be transported to a predetermined disease site and liberated via diverse triggers. Thus, CORMs are distinguished by the liberation initiators such as enzymes (ET-CORMs), illumination (photoCORMs), pH change, or substitution reactions (for recent reviews see [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17]). Especially photoCORMs represent a prominent group because a clean delivery of CO seems to be possible without the necessity to add another chemical trigger [8,[13][14][15].…”

Section: Introductionmentioning

confidence: 99%

Manganese(I)-Based CORMs with 5-Substituted 3-(2-Pyridyl)Pyrazole Ligands

et al. 2017

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Abstract:The reaction of [(OC) 5 MnBr] with substituted 3-(2-pyridyl)pyrazoles) 2-PyPz R H (1a-l) in methanol or diethyl ether yields the yellow to orange manganese(I) complexes, and 1-adamantyl (l). The carbonyl ligands are arranged facially, leading to three chemically different CO ligands due to different trans-positioned Lewis donors. The diversity of the substituent R demonstrates that this photoCORM backbone can easily be varied with a negligible influence on the central (OC) 3 MnBr fragment, because the structural parameters and the spectroscopic data of this unit are very similar for all these derivatives. Even the ferrocenyl complex 2k shows a redox potential for the ferrocenyl subunit which is identical to the value of the free 5-ferrocenyl-3-(2-pyridyl)pyrazole (1k). The ease of variation of the starting 5-substituted 3-(2-pyridyl)pyrazoles) offers a modular system to attach diverse substituents at the periphery of the photoCORM complex.

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Carbon monoxide – physiology, detection and controlled release

Cited by 355 publications

References 204 publications

PhotoCORMs: CO release moves into the visible

PhotoCORMs: CO release moves into the visible

Bactericidal Effect of a Photoresponsive Carbon Monoxide-Releasing Nonwoven against Staphylococcus aureus Biofilms

Manganese(I)-Based CORMs with 5-Substituted 3-(2-Pyridyl)Pyrazole Ligands

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