AI Article Synopsis
- Aryl-urea substituted fatty acids function as protonophores and mitochondrial uncouplers, leveraging a synthetic anion transport system to disrupt proton gradients.
- By substituting the urea with carbamate, a newly identified functional group, the modified compounds still effectively uncouple oxidative phosphorylation and reduce ATP production.
- The study illustrates that dimeric structures formed by the interaction between carboxylate groups and carbamate enable efficient proton transport across membranes, demonstrating the anion transport potential of carbamates.
Article Abstract
Aryl-urea substituted fatty acids are protonophores and mitochondrial uncouplers that utilise a urea-based synthetic anion transport moiety to carry out the protonophoric cycle. Herein we show that replacement of the urea group with carbamate, a functional group not previously reported to possess anion transport activity, produces analogues that retain the activity of their urea counterparts. Thus, the aryl-carbamate substituted fatty acids uncouple oxidative phosphorylation and inhibit ATP production by collapsing the mitochondrial proton gradient. Proton transport proceeds self-assembly of the deprotonated aryl-carbamates into membrane permeable dimeric species, formed by intermolecular binding of the carboxylate group to the carbamate moiety. These results highlight the anion transport capacity of the carbamate functional group.
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| http://dx.doi.org/10.1039/d2ob02049a | DOI Listing |
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