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Fluoxetine scaffold to design tandem molecular antioxidants and green catalysts
RSC Advances ( IF 3.9 ) Pub Date : 2020-5-15 , DOI: 10.1039/d0ra03509b Giovanni Ribaudo 1 , Marco Bortoli 2 , Alberto Ongaro 1 , Erika Oselladore 3 , Alessandra Gianoncelli 1 , Giuseppe Zagotto 3 , Laura Orian 2
RSC Advances ( IF 3.9 ) Pub Date : 2020-5-15 , DOI: 10.1039/d0ra03509b Giovanni Ribaudo 1 , Marco Bortoli 2 , Alberto Ongaro 1 , Erika Oselladore 3 , Alessandra Gianoncelli 1 , Giuseppe Zagotto 3 , Laura Orian 2
Affiliation
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Fluoxetine finds application in the treatment of depression and mood disorders. This selective serotonin-reuptake inhibitor (SSRI) also contrasts oxidative stress by direct ROS scavenging, modulation of the endogenous antioxidant defense system, and/or enhancement of the serotonin antioxidant capacity. We synthesised some fluoxetine analogues incorporating a selenium nucleus, thus expanding its antioxidant potential by enabling a hydroperoxides-inactivating, glutathione peroxidase (GPx)-like activity. Radical scavenging and peroxidatic activity were combined in a water-soluble, drug-like, tandem antioxidant molecule. Selenofluoxetine derivatives were reacted with H2O2 in water, and the mechanistic details of the reaction were unravelled combining nuclear magnetic resonance (NMR), electrospray ionisation-mass spectrometry (ESI-MS) and quantum chemistry calculations. The observed oxidation–elimination process led to the formation of seleninic acid and cinnamylamine in a trans-selective manner. This mechanism is likely to be extended to other substrates for the preparation of unsaturated cinnamylamines.
中文翻译：
氟西汀支架设计串联分子抗氧化剂和绿色催化剂
氟西汀可用于治疗抑郁症和情绪障碍。这种选择性血清素再摄取抑制剂 (SSRI) 还通过直接清除 ROS、调节内源性抗氧化防御系统和/或增强血清素抗氧化能力来对抗氧化应激。我们合成了一些含有硒核的氟西汀类似物，从而通过启用氢过氧化物失活的谷胱甘肽过氧化物酶 (GPx) 样活性来扩展其抗氧化潜力。自由基清除和过氧化活性结合在水溶性、药物样、串联抗氧化分子中。硒氟西汀衍生物与 H 2 O 2反应在水中，结合核磁共振（NMR）、电喷雾电离质谱（ESI-MS）和量子化学计算，揭示了反应的机理细节。观察到的氧化消除过程导致以反式选择性方式形成亚硒酸和肉桂胺。这种机制很可能扩展到其他底物以制备不饱和肉桂胺。
更新日期：2020-05-15
中文翻译：
氟西汀支架设计串联分子抗氧化剂和绿色催化剂
氟西汀可用于治疗抑郁症和情绪障碍。这种选择性血清素再摄取抑制剂 (SSRI) 还通过直接清除 ROS、调节内源性抗氧化防御系统和/或增强血清素抗氧化能力来对抗氧化应激。我们合成了一些含有硒核的氟西汀类似物，从而通过启用氢过氧化物失活的谷胱甘肽过氧化物酶 (GPx) 样活性来扩展其抗氧化潜力。自由基清除和过氧化活性结合在水溶性、药物样、串联抗氧化分子中。硒氟西汀衍生物与 H 2 O 2反应在水中，结合核磁共振（NMR）、电喷雾电离质谱（ESI-MS）和量子化学计算，揭示了反应的机理细节。观察到的氧化消除过程导致以反式选择性方式形成亚硒酸和肉桂胺。这种机制很可能扩展到其他底物以制备不饱和肉桂胺。
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