Tetra-azobenzene extended calix[4]pyrroles: influence of photo-isomerization on chloride binding and its transport through liposomal membranes

Ferreira, Pedro; Aragay, Gemma; Ballester, Pablo

doi:10.1039/d4qo00399c

Org. Chem. Front.

2024

DOI: 10.1039/d4qo00399c

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Tetra-azobenzene extended calix[4]pyrroles: influence of photo-isomerization on chloride binding and its transport through liposomal membranes

Pedro Ferreira,

Gemma Aragay,

Pablo Ballester

Abstract: Photo-modulation in chloride binding affinity and transmembrane transport with tetra-azobenzene extended calix[4]pyrroles.

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Control of Bilayer Transport through a Photoswitchable Membrane‐Stiffening Agent

Bos,

Duindam,

Kock

et al. 2024

Angewandte Chemie

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The mobility of proteins in the bilayer membrane is affected by (local) changes in lipid environment, which is important to their biological functioning. Artificial molecular systems that – to some extent – imitate tasks of membrane‐embedded proteins are increasingly developed, however, they are usually controlled through responsive units in their core structure. Here we present an alternative approach based on an amphiphilic stiff‐stilbene derivative that enables control of membrane fluidity by light. The fluidity increase upon E‐to‐Z isomerization is shown to enhance the activity of known synthetic anion transporters as a result of a higher mobility. The photoisomerization process is studied by UV‐vis and 1H NMR spectroscopy in solution and in POPC vesicles, where the light‐induced changes in fluidity and hence, activity of anion transporters, are monitored by fluorescence spectroscopy. Dynamic light‐scattering (DLS) and cryo‐EM studies show that vesicle integrity is not impaired by photoswitching. Our work introduces a versatile approach to control solute transport by carrier molecules. Moreover, the photocontrol over membrane fluidity and, with that, mobility could eventually be used for directed motion, which we expect to be key in achieving active transport in the future.

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Control of Bilayer Transport through a Photoswitchable Membrane‐Stiffening Agent

Bos,

Duindam,

Kock

et al. 2024

Angewandte Chemie

View full text Add to dashboard Cite

show abstract

Control of Bilayer Transport through a Photoswitchable Membrane‐Stiffening Agent

Bos,

Duindam,

Kock

et al. 2024

Angew Chem Int Ed

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show abstract

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Tetra-azobenzene extended calix[4]pyrroles: influence of photo-isomerization on chloride binding and its transport through liposomal membranes

Abstract: Photo-modulation in chloride binding affinity and transmembrane transport with tetra-azobenzene extended calix[4]pyrroles.

Cited by 2 publications

References 40 publications

Control of Bilayer Transport through a Photoswitchable Membrane‐Stiffening Agent

Control of Bilayer Transport through a Photoswitchable Membrane‐Stiffening Agent

Control of Bilayer Transport through a Photoswitchable Membrane‐Stiffening Agent

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