Switch the click: Ultrafast photochemistry of photoDIBO-OH tracked by time-resolved IR spectroscopy-Reference-Cited by-同舟云学术

Switch the click: Ultrafast photochemistry of photoDIBO-OH tracked by time-resolved IR spectroscopy

Published:2024-05-01 Issue:17 Volume:160 Page:
ISSN:0021-9606
Container-title:The Journal of Chemical Physics
language:en
Short-container-title:

Author:

Denninger L.¹^ORCID,Brunst H.¹^ORCID,van Wilderen L. J. G. W.¹^ORCID,Horz M.²^ORCID,Masood H. M. A.¹^ORCID,McNitt C. D.³^ORCID,Burghardt I.²^ORCID,Popik V. V.³^ORCID,Bredenbeck J.¹^ORCID

Affiliation:

1. Institute of Biophysics, Goethe University 1 , Frankfurt am Main 60438, Germany

2. Institute of Physical and Theoretical Chemistry, Goethe University 2 , Frankfurt am Main 60438, Germany

3. Department of Chemistry, University of Georgia 3 , Athens, Georgia 30602, USA

Abstract

Click chemistry refers to selective reactions developed for grafting of bio(macro)molecules in their biological media. Caged click compounds have been employed to spatiotemporally control click reactions. Here, we survey the uncaging of photo-dibenzocyclooctyne-OH (photoDIBO-OH) to its click-chemistry active form DIBO-OH, with particular attention to its conversion timescale and efficiency. Ultraviolet pump–infrared probe experiments reveal a stepwise decarbonylation: first, carbon monoxide (C≡O) is released within 1.8 ps, and then, it converts, within 10 ps, to DIBO-OH. Completion of uncaging is achieved with an efficiency of ∼50%. A successful demonstration of two-photon uncaging of photoDIBO-OH at long wavelength (700 nm) confers enhanced in vivo compatibility and proceeds on the same timescale.

Funder

Deutsche Forschungsgemeinschaft

Center for Hierarchical Manufacturing, National Science Foundation

Publisher

AIP Publishing

Link

https://pubs.aip.org/aip/jcp/article-pdf/doi/10.1063/5.0196923/19912937/174201_1_5.0196923.pdf

Reference29 articles.

1. Biologically Active Molecules with a “Light Switch”

2. Photoremovable Protecting Groups in Chemistry and Biology: Reaction Mechanisms and Efficacy

3. Photoremovable protecting groups: reaction mechanisms and applications

4. One- and Two-Photon Uncaging of Carbon Monoxide (CO) with Real-Time Monitoring: On-Demand Carbazole-Based Dual CO-Releasing Platform to Test over Single and Combinatorial Approaches for the Efficient Regression of Orthotopic Murine Melanoma In Vivo

5. The nitrodibenzofuran chromophore: a new caging group for ultra-efficient photolysis in living cells