Mixed alkoxy/hydroxy 1,8-naphthalimides: expanded fluorescence colour palette and <i>in vitro</i> bioactivity
Elley E. Rudebeck, Rosalind P. Cox, Toby D. M. Bell, Rameshwor Acharya, Zikai Feng, Nuri Gueven, Trent D. Ashton, Frederick M. Pfeffer
Abstract
An efficient and functional group tolerant route to access hydroxy 1,8-naphthalimides has been used to synthesise a range of mono- and disubstituted hydroxy-1,8-naphthalimides with fluorescence emissions covering the visible spectrum. The dialkoxy substituted compounds prepared possess high quantum yields (up to 0.95) and long fluorescent lifetimes (up to 14 ns). The method has been used to generate scriptaid analogues that successfully inhibit HDAC6 in vitro with tubulin acetylation assays confirming that these compounds are more effective than tubastatin.
Topics & Concepts
FluorescenceAlkoxy groupPhotochemistryChemistryPalette (painting)In vitroRange (aeronautics)Visible spectrumMaterials scienceOrganic chemistryComputer scienceOptoelectronicsBiochemistryOpticsAlkylComposite materialPhysicsOperating systemMolecular Sensors and Ion DetectionLuminescence and Fluorescent MaterialsNanoplatforms for cancer theranostics