On the Question of Uncatalyzed CO Insertion into a Hydrazone Double Bond: A Comparative Study Using Different CO Sources and Substrates DOI Creative Commons
Dongning Liu, Nicola Bauer,

Wen Lu

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(13), P. 9551 - 9556

Published: June 18, 2024

Because of endogenous signaling roles carbon monoxide (CO) and its demonstrated pharmacological effects, there has been extensive interests in developing fluorescent CO probes. Palladium-mediated insertion successfully used for such applications. However, recent years have seen many publications using uncatalyzed into a hydrazone double bond as way to sense CO. Such chemistry no precedents otherwise. Further, the rigor CO-sensing work was largely based on ruthenium–carbonyl complexes CORM-3 surrogates, which reported chemical reactivity release CO2 instead unless presence strong nucleophile dithionite. For all these, it is important reassess feasibility CO-insertion reaction. By studying two "CO probes" gas, this study finds evidence bond. reaction between gas series eight compounds conducted, leading same conclusion. findings are consistent with state-of-the-art knowledge carbonylation do not support mechanism

Language: Английский

Compelling Evidence: A Critical Update on the Therapeutic Potential of Carbon Monoxide DOI
Nicola Bauer, Qiyue Mao,

Aditi Vashistha

et al.

Medicinal Research Reviews, Journal Year: 2025, Volume and Issue: unknown

Published: April 30, 2025

ABSTRACT Carbon monoxide (CO) is an endogenous signaling molecule. It produced via heme degradation by oxygenase (HMOX), releasing stoichiometric amounts of CO, iron, and biliverdin (then bilirubin). The HMOX‐CO axis has long been shown to offer beneficial effects modulating inflammation, proliferation cell death as they relate tissue organ protection. Recent years have seen a large number studies examining CO pharmacology, its molecular targets, cellular mechanisms action, pharmacokinetics, detection methods using various delivery modalities including inhaled gas, solutions, types donors. Unfortunately, one widely used donor type includes four commercially available carbonyl complexes with metal or borane, CORM‐2 (Ru 2+ ), CORM‐3 CORM‐A1 (BH 3 CORM‐401 (Mn + which minimal and/or unpredictable production extensive CO‐independent chemical reactivity biological activity. As result, not all “CO activities” in the literature can be attributed CO. In this review, we summarize key findings based on gas solution for certainty active principal avoid data contamination resulting from confirmed potential reactivities activities “carrier” portion CORMs. Along similar line, discuss interesting research areas brain newly proposed CO/HMOX/dopamine role cognitive stimulation circadian rhythm. This review critical future development field steering clear complications caused chemically reactive molecules.

Language: Английский

Citations

0

The carbon monoxide prodrug oCOm‐21 increases Ca2+ sensitivity of the cardiac myofilament DOI Creative Commons
Fergus M. Payne,

Samantha Nie,

Gary M. Diffee

et al.

Physiological Reports, Journal Year: 2024, Volume and Issue: 12(6)

Published: March 1, 2024

Abstract Patients undergoing cardiopulmonary bypass procedures require inotropic support to improve hemodynamic function and cardiac output. Current inotropes such as dobutamine, can promote arrhythmias, prompting a demand for improved with little effect on intracellular Ca 2+ flux. Low‐dose carbon monoxide (CO) induces effects in perfused hearts. Using the CO‐releasing pro‐drug, oCOm‐21, we investigated if this results from an increase myofilament sensitivity. Male Sprague Dawley rat left ventricular cardiomyocytes were permeabilized, force was measured of ‐log [Ca ] (pCa) range 9.0–4.5 under five conditions: vehicle, oCOm‐21 control BP‐21, levosimendan, (9 cells/group). sensitivity assessed by concentration at which 50% maximal is produced (pCa 50 ). but not BP‐21 significantly increased pCa compared respectively 5.52 vs. 5.47 5.44; p < 0.05). No change phosphorylation seen after treatment. Pretreatment heme scavenger hemopexin, abolished sensitizing oCOm‐21. These hypothesis that oCOm‐21‐derived CO increases through heme‐dependent mechanism phosphorylation. Further analyses will confirm occurs intact heart.

Language: Английский

Citations

3

Iron porphyrin-mediated production of carbon monoxide from phenylpyruvic acid: from potential therapeutic and diagnostic use to physiological implications DOI
Lu Wen,

Rujuta Ghorpade,

Xiaoxiao Yang

et al.

Medicinal Chemistry Research, Journal Year: 2024, Volume and Issue: 33(9), P. 1671 - 1680

Published: July 7, 2024

Language: Английский

Citations

3

Development of photoactivatable CO-releasing tricarbonylrhenium(I) complexes and their integration into cellulose nanocrystals in view of antibacterial activity DOI Creative Commons
Valentine Guilbaud,

Marie Goizet,

Nadine Leygue

et al.

Journal of Photochemistry and Photobiology A Chemistry, Journal Year: 2024, Volume and Issue: 453, P. 115600 - 115600

Published: March 19, 2024

Antibiotic-resistant bacteria represent a growing threat to global health and efforts continue be made seek new ways of addressing this issue. Photoactivatable carbon monoxide (CO)-releasing molecules (photoCORMs) could an alternative solution conventional antibiotics, but their mechanism action is complex still badly known. In the present work, tricarbonylrhenium(I) (Re-Phe(TPP)) was developed, as well more hydrophobic analogue substituted by adamantyl moiety (Re-Ada(TPP)). When irradiated in near UV, these generate rapidly one molecule CO, small amounts singlet oxygen (1O2). Their decarbonylated photoproducts D-Re-Phe(TPP) D-Re-Ada(TPP) only 1O2, on prolonged period time. Finally, complexes were immobilized biocompatible cellulose nanocrystal (CNC) matrix, so that diffusive species (CO 1O2) may active ones. The bactericidal activity all systems evaluated two strains, causative main wound infections. No compound Pseudomonas aeruginosa. contrast, free Re-Phe(TPP) appeared very good antibacterial agent dark Staphylococcus aureus. same adsorbed CNC material ineffective. Consequently, its mainly attributed direct biological effect. derivative Re-Ada(TPP) presence light, while photoproduct showed moderate activity, suggesting production 1O2 not enough induce significant This work allows identify limits Re(I) photoCORMs corresponding nanomaterials, which are little used fight against bacteria, it provides indications how improve design.

Language: Английский

Citations

2

Characterization of the CO release properties of a common CO donor, CORM-401, in the context of its application in studying CO biology DOI
Nicola Bauer, Qiyue Mao, Xiaoxiao Yang

et al.

Medicinal Chemistry Research, Journal Year: 2024, Volume and Issue: 33(8), P. 1374 - 1383

Published: April 18, 2024

Language: Английский

Citations

2

Inhibitors of NLRP3 Inflammasome Formation: A Cardioprotective Role for the Gasotransmitters Carbon Monoxide, Nitric Oxide, and Hydrogen Sulphide in Acute Myocardial Infarction DOI Open Access
Fergus M. Payne,

Alisha R. Dabb,

Joanne C. Harrison

et al.

International Journal of Molecular Sciences, Journal Year: 2024, Volume and Issue: 25(17), P. 9247 - 9247

Published: Aug. 26, 2024

Myocardial ischaemia reperfusion injury (IRI) occurring from acute coronary artery disease or cardiac surgical interventions such as bypass surgery can result in myocardial dysfunction, presenting as, “stunning”, arrhythmias, infarction, and adverse remodelling, may lead to both a systemic localised inflammatory response. This response is regulated through the nucleotide-binding oligomerisation domain (NACHT), leucine-rich repeat (LRR)-containing protein family pyrin (PYD)-3 (NLRP3) inflammasome, multimeric structure whose components are present within cardiomyocytes fibroblasts. The NLRP3 inflammasome activated via numerous danger signals produced by IRI central resultant innate immune Inhibition of this inherent has been shown protect myocardium stop occurrence syndrome following re-establishment circulation. Therapies prevent formation clinic currently lacking, therefore, new pharmacotherapies required. review will highlight role during examine therapeutic value inhibition with particular attention carbon monoxide, nitric oxide, hydrogen sulphide potential pharmacological inhibitors activation.

Language: Английский

Citations

2

CO prodrugs: a new scaffold of adamantane-fused norbornen-7-ones with tunable water solubility DOI

Ce Yang,

Xingyue Ji,

G. S. Sainaga Jyothi Vaskuri

et al.

Medicinal Chemistry Research, Journal Year: 2024, Volume and Issue: 33(11), P. 2122 - 2130

Published: Oct. 24, 2024

Language: Английский

Citations

2

A comprehensive survey of Mn(i) carbonyls as CO-releasing molecules reported over the last two decades DOI
Ahmed M. Mansour, Rabaa M. Khaled, Ola R. Shehab

et al.

Dalton Transactions, Journal Year: 2024, Volume and Issue: 53(48), P. 19022 - 19057

Published: Jan. 1, 2024

An overview of the CO releasing properties and biological applications (antimicrobial activity cytotoxicity) manganese( i ) carbonyl complexes.

Language: Английский

Citations

2

Visible Light Triggerable CO Releasing Micelles DOI
Mckenna G. Hanson,

Ram Ambre,

Riya Joshi

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 12, 2024

Carbon monoxide (CO), along with nitric oxide and hydrogen sulfide, is one of a trinity known gasotransmitters, or endogenously produced gaseous molecules that signal regulate panoply physiological functions. CO releasing (CORMs) are chemical tools enable the study application this ephemeral gas, that, ideally, release on-demand when externally stimulated. Surveying available triggers, photolysis potentially advantageous: It contactless grants practitioners unparalleled spatial temporal control. However, current phototriggered CORMs capricious do not meet needs. Presented here highly efficient platform for visible light triggered gas. This built on unique containing functionality, cyclopropenone, which undergoes facile decarbonylation through (470 nm) mediated photoredox catalysis. Due to exothermic strain-release occurs upon formation CO, photoreaction rapid, quantitative, has tunable rates. To render photo-CORM water-soluble, deliverable, keep reactants in proximity, necessary components were polymerized into block copolymers self-assemble micelles (CORMIs). was compared directly other state-of-the-art CORMs, showing significantly improved production efficiency, lower toxicity, rates, consistent efficacy

Language: Английский

Citations

2

A novel fluorescent probe for ultra-fast detection of CORM-3 and spatiotemporal multi-organelle targeting DOI

Yongshun Chen,

Bang-Zhao Zhou,

Fengting Liu

et al.

Sensors and Actuators B Chemical, Journal Year: 2023, Volume and Issue: 399, P. 134824 - 134824

Published: Oct. 21, 2023

Language: Английский

Citations

4