TY - JOUR
T1 - Evaluation of a new benzothiazole derivative with antioxidant activity in the initial phase of acetaminophen toxicity
AU - Cabrera-Pérez, Laura C.
AU - Padilla-Martínez, Itzia I.
AU - Cruz, Alejandro
AU - Mendieta-Wejebe, Jessica E.
AU - Tamay-Cach, Feliciano
AU - Rosales-Hernández, Martha C.
N1 - Publisher Copyright:
© 2016 The Authors
PY - 2019/12
Y1 - 2019/12
N2 - Increasing evidence indicates that benzothiazoles and thioureas have the ability to inactivate reactive chemical species through their antioxidant activity. In this context, we designed and synthesized two benzothiazole-isothiourea derivatives, (E)-5-((benzo[d]thiazol-2-ylimino)(methylthio)methylamino)-2-hydroxybenzoic acid (compound 1) and (S,E)-2-((benzo[d]thiazol-2-ylimino)(methylthio)methylamino)-3-(4-hydroxyphenyl) propanoic acid (compound 2). The 2,2′-diphenyl-1-picrylhydrazyl radical reduction and Fenton reaction were used to evaluate the free radical scavenging activity of both compounds in vitro. The results indicated that compound 1 exhibited the highest scavenging activity. Hence, it was evaluated ex vivo using the initial phase of the acetaminophen-induced hepatotoxicity model. In particular, we demonstrated that compound 1 increased the reduced glutathione content and decreased the malondialdehyde levels. In addition, it was capable of inhibiting cytochrome P450 and producing a protective effect against the reactive intermediary N-acetyl-p-benzoquinoneimine.
AB - Increasing evidence indicates that benzothiazoles and thioureas have the ability to inactivate reactive chemical species through their antioxidant activity. In this context, we designed and synthesized two benzothiazole-isothiourea derivatives, (E)-5-((benzo[d]thiazol-2-ylimino)(methylthio)methylamino)-2-hydroxybenzoic acid (compound 1) and (S,E)-2-((benzo[d]thiazol-2-ylimino)(methylthio)methylamino)-3-(4-hydroxyphenyl) propanoic acid (compound 2). The 2,2′-diphenyl-1-picrylhydrazyl radical reduction and Fenton reaction were used to evaluate the free radical scavenging activity of both compounds in vitro. The results indicated that compound 1 exhibited the highest scavenging activity. Hence, it was evaluated ex vivo using the initial phase of the acetaminophen-induced hepatotoxicity model. In particular, we demonstrated that compound 1 increased the reduced glutathione content and decreased the malondialdehyde levels. In addition, it was capable of inhibiting cytochrome P450 and producing a protective effect against the reactive intermediary N-acetyl-p-benzoquinoneimine.
KW - Acetaminophen
KW - Antioxidants
KW - Benzothiazole derivatives
KW - Cytochrome P-450
KW - Hepatotoxicity
KW - Isothiourea derivatives
UR - http://www.scopus.com/inward/record.url?scp=84975705712&partnerID=8YFLogxK
U2 - 10.1016/j.arabjc.2016.02.004
DO - 10.1016/j.arabjc.2016.02.004
M3 - Artículo
SN - 1878-5352
VL - 12
SP - 3871
EP - 3882
JO - Arabian Journal of Chemistry
JF - Arabian Journal of Chemistry
IS - 8
ER -