Discovery of phenylsulfonylfuroxan derivatives as gamma globin inducers by histone acetylation

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Data

2018-06-25

Autores

Melo, Thais Regina Ferreira de [UNESP]
Kumkhaek, Chutima
Fernandes, Guilherme Felipe Dos Santos [UNESP]
Lopes Pires, Maria Elisa
Chelucci, Rafael Consolin [UNESP]
Barbieri, Karina Pereira [UNESP]
Coelho, Fernanda [UNESP]
Capote, Ticiana Sidorenko de Oliveira [UNESP]
Lanaro, Carolina
Carlos, Iracilda Zeppone [UNESP]

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Resumo

N-oxide derivatives 5(a-b), 8(a-b), and 11(a-c) were designed, synthesized and evaluated in vitro and in vivo as potential drugs that are able to ameliorate sickle cell disease (SCD) symptoms. All of the compounds demonstrated the capacity to releasing nitric oxide at different levels ranging from 0.8 to 30.1%, in vivo analgesic activity and ability to reduce TNF-α levels in the supernatants of monocyte cultures. The most active compound (8b) protected 50.1% against acetic acid-induced abdominal constrictions, while dipyrone, which was used as a control only protected 35%. Compounds 8a and 8b inhibited ADP-induced platelet aggregation by 84% and 76.1%, respectively. Both compounds increased γ-globin in K562 cells at 100 μM. The mechanisms involved in the γ-globin increase are related to the acetylation of histones H3 and H4 that is induced by these compounds. In vitro, the most promising compound (8b) was not cytotoxic, mutagenic and genotoxic.

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Palavras-chave

Analgesic activity, Antiplatelet activity, Epigenetic, Fetal hemoglobin, Furoxan, Sickle cell disease

Como citar

European journal of medicinal chemistry, v. 154, p. 341-353.