Abstract
3‐Hydroxyisoquinolines (ISOs) and their tautomeric isoquinolin‐3‐ones are heterocycles with attractive biological properties. Here we reported the revisited synthesis of a highly functionalized ISO that showed blue fluorescence and the characterization of its biological properties in an invertebrate animal model, the ascidian Ciona intestinalis. Larvae exposed to ISO at concentrations higher than 1 μM showed an intense fluorescence localized in the cell nuclei of all tissues. Moreover, exposure to ISO interfered with larval ability to swim; this neuromuscular effect was reversible. Overall, these results suggested that ISOs can have promising applications as novel fluorescent dyes of the cell nuclei.
Highlights
3-Hydroxyisoquinolines (ISOs) and their tautomeric isoquinolin3-ones are heterocycles with attractive biological properties
Fluorescence efficiency was strongly affected by the substitution of the isoquinoline core as the quantum yields determined with anthracene as a relative standard (Φf = 0.36) fall in the range of 0.20 to 0.90 (Scheme 1)
After filtration on celite to remove palladium-related impurities, the mixture was treated with trifluoroacetic acid (TFA) to give 3, with 1,8-diazabicyclo [5.4.0]undec-7-ene (DBU) in MeCN to promote the aromatization
Summary
We describe the revisited synthesis of ISO-1, chosen as model compound, and explore its biological properties in invertebrate animal model, the ascidian Ciona intestinalis. Ciona intestinalis larvae have a stereotyped behaviour making them a suitable model to test the effects of chemicals on their neuromuscular system. Larvae show a positive phototropism and swim by lateral bending of their tail towards the surface After few hours, they turn into negative phototropic and start to move toward the substrate searching for an appropriate site to which they adhere by means of three adhesive papillae.[15,16] In addition to their numerous practical advantages, ascidians phylogenetic position makes these organisms suitable for testing chemicals. Synthetic strategy for the preparation of a library of substituted 3-hydroxyisoquinolines and structure and photophysical properties of compound ISO-1
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