ArticlePhotochemistry and photobiology2019
A Cyanine Photooxidation/β-Elimination Sequence Enables Near-infrared Uncaging of Aryl Amine Payloads.
Article in Photochemistry and photobiology, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
What it found
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
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Who cites it
8 citing papers in PubMed, 24 citations in OpenAlex.
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- Development of label-free light-controlled gene expression technologies using mid-IR and terahertz light.Frontiers in bioengineering and biotechnology · 2024Review
- Spatiotemporal Control of Biology: Synthetic Photochemistry Toolbox with Far-Red and Near-Infrared Light.ACS chemical biology · 2022Review
- Photouncaging of Carboxylic Acids from Cyanine Dyes with Near-Infrared Light.Angewandte Chemie (International ed. in English) · 2022Article
- Visible-to-NIR-Light Activated Release: From Small Molecules to Nanomaterials.Chemical reviews · 2020Article
- Cyanine Nanocages Activated by Near-Infrared Light for the Targeted Treatment of Traumatic Brain Injury.Frontiers in chemistry · 2020Article
- Long-wavelength photoremovable protecting groups: On the way toComputational and structural biotechnology journal · 2020Review
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Authors and funding
4 authors at 3 institutions in 2 countries.
Funding
Abstract
Uncaging strategies that use near-infrared wavelengths can enable the highly targeted delivery of biomolecules in complex settings. Many methods, including an approach we developed using cyanine photooxidation, are limited to phenol-containing payloads. Given the critical role of amines in diverse biological processes, we sought to use cyanine photooxidation to initiate the release of aryl amines. Heptamethine cyanines substituted with an aryl amine at the C4' position undergo only inefficient release, likely due electronic factors. We then pursued the hypothesis that the carbonyl products derived from cyanine photooxidation could undergo efficient β-elimination. After examining both symmetrical and unsymmetrical scaffolds, we identify a merocyanine substituted with indolenine and coumarin heterocycles that undergoes efficient photooxidation and aniline uncaging. In total, these studies provide a new scheme-cyanine photooxidation followed by β-elimination-through which to design photocages with efficient uncaging properties.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.