No abstract

SummaryPyrrolo[2,1-a]isoquinoline alkaloids have been prepared via a visible light photoredox catalyzed oxidation/[3 + 2] cycloaddition/oxidative aromatization cascade using Rose Bengal as an organo-photocatalyst. A variety of pyrroloisoquinolines have been obtained in good yields under mild and metal-free reaction conditions.

The use of bioorthogonal probes that display fluorogenic or phosphorogenic properties is advantageous to the labeling and imaging of biomolecules in live cells and organisms. Herein we present the design of three iridium(III) complexes containing a nitrone moiety as novel phosphorogenic bioorthogonal probes. These probes were non-emissive owing to isomerization of the C=N group but showed significant emission enhancement upon cycloaddition reaction with strained cyclooctynes. Interestingly, the connection of the nitrone ligand to the cationic iridium(III) center led to accelerated reaction kinetics. These nitrone complexes were also identified as phosphorogenic bioorthogonal labels and imaging reagents for cyclooctyne-modified proteins. These findings contribute to the development of phosphorogenic bioorthogonal probes and imaging reagents.

Sialica cids play important roles in mammalian development, cell-cella ttachment, ands ignaling. As cancer cells utilize their overexpresseds ialylated antigens to propagate metastases, the development of probesf or sialic acids is of high importance. Herein, we report three luminescent cyclometalated iridium(III) bipyridine complexes bearing ap henylboronica cid (PBA) moiety.S pectrophotometric titrations revealed that the PBA complexes displayed higher bindinga ffinity for the most commons ialic acid N-acetylneuraminic acid (Neu5Ac) comparedw ith simple sugars that are commonly found on glycoproteins. Notably,c ellular imaginga nd uptake experimentss howedt hat the PBA complexes were able to recognize cellular sialic acidr esidues,r esulting in more efficient uptake than the boronic acid-free analogs. Additionally,o ne of the PBA complexes was shown to discriminate between cancerous and noncancerous cells.

The use of bioorthogonal probes that display fluorogenic or phosphorogenic properties is advantageous to the labeling and imaging of biomolecules in live cells and organisms.H erein we present the design of three iridium(III) complexes containing an itrone moiety as novel phosphorogenic bioorthogonal probes.T hese probes were non-emissive owingt oi somerization of the C = Ng roup but showed significant emission enhancement upon cycloaddition reaction with strained cyclooctynes.Interestingly,the connection of the nitrone ligand to the cationic iridium(III) center led to accelerated reaction kinetics.T hese nitrone complexes were also identified as phosphorogenic bioorthogonal labels and imaging reagents for cyclooctyne-modified proteins.T hese findings contribute to the development of phosphorogenic bioorthogonal probes and imaging reagents.