Evidence map›Paper›PMID 38225711›Full record

ArticleAdvanced science (Weinheim, Baden-Wurttemberg, Germany)2024

Theoretical Design and Synthesis of Caged Compounds Using X-Ray-Triggered Azo Bond Cleavage.

Koki Ogawara, Osamu Inanami, Hideo Takakura, Kenichiro Saita, Kohei Nakajima, Sonu Kumar, Naoya Ieda, Masato Kobayashi, Tetsuya Taketsugu, Mikako Ogawa

Abstract read
In one paragraph

Article in Advanced science (Weinheim, Baden-Wurttemberg, Germany), 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.

0numbers the graph read from it
0cells of the map it votes in
3citing papers in PubMed
–field-weighted citation impact
1 · What the graph read from it

What it found

Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.

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.

2 · The registry

The trial behind it

Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.

Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.

3 · Its place in the literature

Who cites it

3 citing papers in PubMed.

  1. Design rules for externally triggered drug uncaging under optical and radiolytic regimes.European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V · 2026
    Review
  2. Review
  3. Theoretical Design and Synthesis of Caged Compounds Using X-Ray-Triggered Azo Bond Cleavage.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024
    Article
4 · The record

Corrections and comments

PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.

5 · Who and what money

Authors and funding

10 authors.

Koki OgawaraLaboratory of Bioanalysis and Molecular Imaging, Graduate School of Pharmaceutical Sciences, Hokkaido University, Sapporo, Hokkaido, 060-0812, Japan.
Osamu InanamiLaboratory of Radiation Biology, Graduate School of Veterinary Medicine, Hokkaido University, Sapporo, Hokkaido, 060-0818, Japan.ORCID https://orcid.org/0000-0001-7895-3918
Hideo TakakuraLaboratory of Bioanalysis and Molecular Imaging, Graduate School of Pharmaceutical Sciences, Hokkaido University, Sapporo, Hokkaido, 060-0812, Japan.ORCID https://orcid.org/0000-0003-3696-6109
Kenichiro SaitaQuantum Chemistry Lab, Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo, Hokkaido, 060-0810, Japan.ORCID https://orcid.org/0000-0001-7705-5833
Kohei NakajimaLaboratory of Bioanalysis and Molecular Imaging, Graduate School of Pharmaceutical Sciences, Hokkaido University, Sapporo, Hokkaido, 060-0812, Japan.ORCID https://orcid.org/0009-0000-5363-2042
Sonu KumarQuantum Chemistry Lab, Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo, Hokkaido, 060-0810, Japan.ORCID https://orcid.org/0000-0002-3807-836X
Naoya IedaLaboratory of Bioanalysis and Molecular Imaging, Graduate School of Pharmaceutical Sciences, Hokkaido University, Sapporo, Hokkaido, 060-0812, Japan.
Masato KobayashiQuantum Chemistry Lab, Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo, Hokkaido, 060-0810, Japan.ORCID https://orcid.org/0000-0002-4001-3581
Tetsuya TaketsuguQuantum Chemistry Lab, Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo, Hokkaido, 060-0810, Japan.ORCID https://orcid.org/0000-0002-1337-6694
Mikako OgawaLaboratory of Bioanalysis and Molecular Imaging, Graduate School of Pharmaceutical Sciences, Hokkaido University, Sapporo, Hokkaido, 060-0812, Japan.ORCID https://orcid.org/0000-0002-3432-4519

Funding

AMED JP19am0101093JST-CREST JPMJCR1902JST-SPRING JPMJSP2119MEXT JPMXS0420100120
6 · The paper itself

Abstract

Caged compounds are frequently used in life science research. However, the light used to activate them is commonly absorbed and scattered by biological materials, limiting their use to basic research in cells or small animals. In contrast, hard X-rays exhibit high bio-permeability due to the difficulty of interacting with biological molecules. With the main goal of developing X-ray activatable caged compounds, azo compounds are designed and synthesized with a positive charge and long π-conjugated system to increase the reaction efficiency with hydrated electrons. The azo bonds in the designed compounds are selectively cleaved by X-ray, and the fluorescent substance Diethyl Rhodamine is released. Based on the results of experiments and quantum chemical calculations, azo bond cleavage is assumed to occur via a two-step process: a two-electron reduction of the azo bond followed by N─N bond cleavage. Cellular experiments also demonstrate that the azo bonds can be cleaved intracellularly. Thus, caged compounds that can be activated by an azo bond cleavage reaction promoted by X-ray are successfully generated.

Indexed as

azo compoundscancercleavage reactionradical reactionsreaction mechanism

Identifiers

PMID38225711
PMCPMC10966529

What OpenQuestion holds

Textmetadata
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Registered trials

None linked

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.