Double click macrocyclization with Sondheimer diyne of aza-dipyrrins for B–Free bioorthogonal imaging

Dan Wu; Gonzalo Durán-Sampedro; Sheila Fitzgerald; Massimiliano Garre; Donal F. O'Shea

doi:10.1039/D2CC06461H

You do not have JavaScript enabled. Please enable JavaScript to access the full features of the site or access our non-JavaScript page.

Double click macrocyclization with Sondheimer diyne of aza-dipyrrins for B–F_ree bioorthogonal imaging†

Dan Wu,^a Gonzalo Durán-Sampedro,^a Sheila Fitzgerald,

^a Massimiliano Garre

^a and Donal F. O'Shea

*^a

Author affiliations

* Corresponding authors

^a Department of Chemistry, RCSI, 123 St Stephen's Green, Dublin 2, Ireland
E-mail: donalfoshea@rcsi.ie

Abstract

Sequential azide/diyne cycloadditions proved highly effective for the macrocyclization of a bis-azido aza-dipyrrin. Macrocyclic aza-dipyrrin could be produced in 30 min at rt in water with changes in fluorescence intensity and lifetimes measurable upon reaction. Live cell microscopy showed that aza-dipyrrins were suitable for confocal and STED super-resolution imaging and a bioorthogonal response to macrocyclization could be detected in cellular compartments. These results will encourage a broader examination of the sensing and imaging uses of aza-dipyrrins.

This article is part of the themed collection: Chemosensors and Molecular Logic

Download options Please wait...

Supplementary files

Supplementary information PDF (2180K)

Article information

DOI: https://doi.org/10.1039/D2CC06461H
Article type: Communication
Submitted: 28 Nov 2022
Accepted: 19 Jan 2023
First published: 20 Jan 2023
This article is Open Access

Download Citation

Chem. Commun., 2023,59, 1951-1954

Permissions

Request permissions

Double click macrocyclization with Sondheimer diyne of aza-dipyrrins for B–F_ree bioorthogonal imaging

D. Wu, G. Durán-Sampedro, S. Fitzgerald, M. Garre and D. F. O'Shea, Chem. Commun., 2023, 59, 1951 DOI: 10.1039/D2CC06461H

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. You can use material from this article in other publications, without requesting further permission from the RSC, provided that the correct acknowledgement is given and it is not used for commercial purposes.

To request permission to reproduce material from this article in a commercial publication, 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 commercial publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Social activity

Fetching data from CrossRef.
This may take some time to load.

Chemical Communications