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

Author(s):Show less -

Oliveira, Marilene Silva ^{[1, 2, 3]} ; Chorociejus, Gabriel ^[1] ; Angeli, Jose Pedro F. ^[4] ; Vila Verde, Giuliana ^[3] ; Aquino, Gilberto L. B. ^[3] ; Ronsein, Graziella E. ^[1] ; Oliveira, Mauricio Cesar Bof de ^[5] ; Barbosa, Livea F. ^[1] ; Medeiros, Marisa H. G. ^[1] ; Greer, Alexander ^{[6, 7]} ; Di Mascio, Paolo ^[1]

Affiliation

^[1] Univ Sao Paulo, Inst Quim, Dept Bioquim, BR-05508000 Sao Paulo, SP - Brazil

^[2] Inst Fed Educ Ciencia & Tecnol Goiano, Dept Agroquim, Campus Rio Verde, Rio Verde, Go - Brazil

^[3] Univ Estadual Goias, Campus Anapolis Ciencias Exatas & Tecnol Henr San, BR-75001970 Anapolis, Go - Brazil

^[4] Univ Wurzburg, Rudolf Virchow Ctr Translat Bioimaging, D-97080 Wurzburg - Germany

^[5] Policia Fed, Setor Tecn Cient, BR-05038090 Sao Paulo, SP - Brazil

^[6] CUNY Brooklyn Coll, Dept Chem, Brooklyn, NY 11210 - USA

^[7] CUNY, PhD Program Chem, Grad Ctr, 365 Fifth Ave, New York, NY 10016 - USA

• Document type: Journal article
• Source: PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES; v. 19, n. 11, p. 1590-1602, NOV 1 2020.
• Web of Science Citations: 0

Abstract

Studies have previously shown that anthracene and naphthalene derivatives serve as compounds for trapping and chemically generating singlet molecular oxygen {[}O-2((1)Delta(g))], respectively. Simple and efficient synthetic routes to anthracene and naphthalene derivatives are needed, for improved capture and release of O-2((1)Delta(g)) in cellular environments. Because of this need, we have synthesized a dihydroxypropyl amide naphthlene endoperoxide as a O-2((1)Delta(g)) donor, as well as five anthracene derivatives as O-2((1)Delta(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)Delta(g)) acceptors and would be amenable for future use in biological systems to expand the understanding of O-2((1)Delta(g)) in biochemistry. (AU)

• FAPESP's process: 12/12663-1 - Singlet molecular oxygen and peroxides in chemical biology
• Grantee: Paolo Di Mascio
• Support Opportunities: Research Projects - Thematic Grants
• FAPESP's process: 13/07937-8 - Redoxome - Redox Processes in Biomedicine
• Grantee: Ohara Augusto
• Support Opportunities: Research Grants - Research, Innovation and Dissemination Centers - RIDC