Issue 29, 2022

Utilising fluorescent reporters to probe the mode of action of norbornen-7-one CO releasing molecules

Abstract

The synthesis of the fluorescent organic carbon monoxide releasing molecules oCOm-57, oCOm-58, and oCOm-66 are reported. These oCOms are water soluble and exhibit a “turn-on” fluorescent behaviour when CO is released under physiological conditions. oCOm-66 also contains an additional nitro-naphthalimide moiety that functions as a fluorescent reporter. Delivery of CO released from these oCOms to the mitochondria of AC-16 cardiomyocytes was confirmed using confocal microscopy in conjuction with MitoTracker Red. While the neutral, PEGylated oCOm-57 was found to remain in the extracellular environment releasing CO to diffuse into the cellular compartments, the positively charged oCOm-58 and -66 are targeted to the mitochondria where they release CO. Notably, the use of the fluorescent oCOms in live cellular imaging, allows the intracellular CO delivery and oCOm localisation to be characterised. This cellular confocal study also shows that, subtoxic concentrations of CO released from these molecules preserved mitochondrial energetics as indicated by the membrane potential dependent MitoTracker Red.

Graphical abstract: Utilising fluorescent reporters to probe the mode of action of norbornen-7-one CO releasing molecules

Supplementary files

Article information

Article type
Paper
Submitted
10 Jun 2022
Accepted
01 Jul 2022
First published
06 Jul 2022

Org. Biomol. Chem., 2022,20, 5812-5819

Utilising fluorescent reporters to probe the mode of action of norbornen-7-one CO releasing molecules

H. M. Johnston, J. T. B. Kueh, R. H. Hartley, A. R. Bland, F. M. Payne, J. C. Harrison, I. A. Sammut and D. S. Larsen, Org. Biomol. Chem., 2022, 20, 5812 DOI: 10.1039/D2OB01076C

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements