Heck reaction synthesis of anthracene and naphthalene derivatives as traps and clean chemical sources of singlet molecular oxygen in biological systems

Studies have previously shown that anthracene and naphthalene derivatives serve as compounds for trapping and chemically generating singlet molecular oxygen [O 2 ( 1 Δ g )], respectively. Simple and efficient synthetic routes to anthracene and naphthalene derivatives are needed, for improved capture and release of O 2 ( 1 Δ g ) in cellular environments. Because of this need, we have synthesized a dihydroxypropyl amide naphthlene endoperoxide as a O 2 ( 1 Δ g ) donor, as well as five anthracene derivatives as O 2 ( 1 Δ g ) acceptor. The anthracene derivatives bear dihydroxypropyl amide, ester, and sulfonate ion end groups connected to 9,10-positions by way of unsaturated (vinyl) and saturated (ethyl) bridging groups. Heck reactions were found to yield these six compounds in easy-to-carry out 3-step reactions in yields of 50-76%. Preliminary results point to the potential of the anthracene compounds to serve as O 2 ( 1 Δ g ) acceptors and would be amenable for future use in biological systems to expand the understanding of O 2 ( 1 Δ g ) in biochemistry. Our study shows that new anthracene and naphthalene derivatives function as compounds for trapping and chemically generating singlet molecular oxygen [O 2 ( 1 Δ g )], respectively. The syntheses of these derivatives are described, as well as some localization testing in cells.