Synthesis and antiproliferative mechanism of action of pyrrolo[3′,2′:6,7] cyclohepta[1,2-d]pyrimidin-2-amines as singlet oxygen photosensitizers

Virginia Spano', Daniele Giallombardo, Paola Barraja, Girolamo Cirrincione, Alessandra Montalbano, Patrizia Diana, Anna Carbone, Barbara Parrino, Filippo Doria, Matteo Nadai, Ilaria Frasson, Mauro Freccero, Sara N. Richter

Risultato della ricerca: Article

11 Citazioni (Scopus)

Abstract

A new series of pyrrolo[3′,2′:6,7]cyclohepta[1,2-d]pyrimidin-2-amines, was conveniently prepared using a versatile and high yielding multistep sequence. A good number of derivatives was obtained and the cellular photocytotoxicity was evaluated in vitro against three different human tumor cell lines with EC50 (0.08–4.96 μM) values reaching the nanomolar level. Selected compounds were investigated by laser flash photolysis. The most photocytotoxic derivative, exhibiting a fairly long-lived triplet state (τ ∼ 7 μs) and absorbance in the UV–Vis, was tested in the photo-oxidations of 9,10-anthracenedipropionic acid (ADPA) by singlet oxygen. The photosentizing properties are responsible for the compounds’ ability to photoinduce massive cell death with involvement of mitochondria.
Lingua originaleEnglish
pagine (da-a)447-461
Numero di pagine15
RivistaEuropean Journal of Medicinal Chemistry
Volume123
Stato di pubblicazionePublished - 2016

All Science Journal Classification (ASJC) codes

  • Pharmacology
  • Drug Discovery
  • Organic Chemistry

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