Detection of Lysosome by a Fluorescent Heterocycle: Development of Fused Pyrido–Imidazo–Indole Framework via Cu-Catalyzed Tandem N‑Arylation

Fluorescent active small molecules for organelle-specific bioimaging are in great demand. We synthesized 20 different pyrido–imidazo–indole fused heterocycles (6–5–5–6 ring) via copper catalyzed tandem N-arylation reaction in moderate to good yields. Due to decent fluorescent property, lysosome-dire...

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Veröffentlicht in:Journal of organic chemistry 2018-11, Vol.83 (21), p.13011-13018
Hauptverfasser: Banerji, Biswadip, Chatterjee, Satadru, Chandrasekhar, Kadaiahgari, Ghosh, Saswati, Mukherjee, Kaustuv, Mandal, Chitra
Format: Artikel
Sprache:eng
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Zusammenfassung:Fluorescent active small molecules for organelle-specific bioimaging are in great demand. We synthesized 20 different pyrido–imidazo–indole fused heterocycles (6–5–5–6 ring) via copper catalyzed tandem N-arylation reaction in moderate to good yields. Due to decent fluorescent property, lysosome-directing moieties were attached on two of these heterocycles. Delightfully, those molecules tracked lysosome with bright blue fluorescence and colocalized with a known lysosome marker (Lysotracker Red) in human/murine cells. Therefore, it may be considered as a rapid (10 min) lysosome staining probe.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b01513