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Bioconjugatable synthetic chlorins rendered water-soluble with three PEG-12 groups via click chemistry

    https://doi.org/10.1142/S1088424619501219Cited by:9 (Source: Crossref)

    Chlorins provide many ideal features for use as red-region fluorophores but require molecular tailoring for solubilization in aqueous solution. A chlorin building-block bearing 18,18-dimethyl, 15-bromo and 10-[2,4,6-tris(propargyloxy)phenyl] substituents has been transformed via click chemistry with CH3(OCH2CH2)12-N3 followed by Suzuki coupling with 3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoic acid, thereby installing a water-solubilization motif and a bioconjugatable handle, respectively. In toluene, N,N-dimethylformamide (DMF) or water, the resulting facially encumbered free base chlorin exhibits characteristic chlorin absorption (λabs412, 643 nm) and fluorescence (λem645 nm) spectra with only modest variation in fluorescence quantum yield (Φf) values (0.24, 0.25 and 0.19, respectively). The zinc chlorin derived therefrom exhibits similar spectral constancy (λabs414 and 613 nm, λem616 nm) and Φf= 0.094, 0.10 and 0.086 in the three solvents. The results together indicate the viability of the molecular design and synthetic methodology to create red-region fluorophores for use in diverse applications.

    Dedicated to Professor Atsuhiro Osuka on the occasion of his 65th birthday.

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