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

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Abstract

Studies have previously shown that anthracene and naphthalene derivatives serve as compounds for trapping and chemically generating singlet molecular oxygen [O2(1Δg)], respectively. Simple and efficient synthetic routes to anthracene and naphthalene derivatives are needed, for improved capture and release of O2(1Δg) in cellular environments. Because of this need, we have synthesized a dihydroxypropyl amide naphthlene endoperoxide as a O2(1Δg) donor, as well as five anthracene derivatives as O2(1Δg) 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 O2(1Δg) acceptors and would be amenable for future use in biological systems to expand the understanding of O2(1Δg) in biochemistry.

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Authors and Affiliations

  1. Departamento de Bioquímica, Instituto de Química, Universidade de São Paulo, CP CP26077, CEP 05508-000, São Paulo, SP, Brazil

    Marilene Silva Oliveira, Gabriel Chorociejus, Graziella E. Ronsein, Livea F. Barbosa, Marisa H. G. Medeiros & Paolo Di Mascio

  2. Departamento de Agroquímica, Instituto Federal de Educação, Campus Rio Verde, Rio Verde, Goiás, Brazil

    Marilene Silva Oliveira

  3. Campus Anápolis de Ciências Exatas e Tecnológicas Henrique Santillo, Universidade Estadual de Goiás, 75001-970, Anápolis, GO, Brazil

    Marilene Silva Oliveira, Giuliana Vila Verde & Gilberto L. B. Aquino

  4. Rudolf Virchow Center for Translational Bioimaging, University of Würzburg, 97080, Würzburg, Germany

    José Pedro F. Angeli

  5. Setor Técnico-Científico, Polícia Federal, CEP 05038-090, São Paulo, SP, Brazil

    Maurício César Bof de Oliveira

  6. Department of Chemistry, Brooklyn College, Brooklyn, New York, 11210, USA

    Alexander Greer

  7. Ph.D. Program in Chemistry, The Graduate Center of the City University of New York, 365 Fifth Avenue, New York, 10016, USA

    Alexander Greer

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  1. Marilene Silva Oliveira
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  2. Gabriel Chorociejus
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  3. José Pedro F. Angeli
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  4. Giuliana Vila Verde
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Correspondence to Marilene Silva Oliveira or Paolo Di Mascio.

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Oliveira, M.S., Chorociejus, G., Angeli, J.P.F. et al. Heck reaction synthesis of anthracene and naphthalene derivatives as traps and clean chemical sources of singlet molecular oxygen in biological systems. Photochem Photobiol Sci 19, 1590–1602 (2020). https://doi.org/10.1039/d0pp00153h

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