Synthesis, antioxidant and anti-inflammatory properties of an apocynin-derived dihydrocoumarin

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Autor(es): dc.contributorUniversidade Estadual Paulista (UNESP)-
Autor(es): dc.creatorParacatu, Luana C.-
Autor(es): dc.creatorZeraik, Maria L.-
Autor(es): dc.creatorDe Carvalho Bertozo, Luiza-
Autor(es): dc.creatorDe Andrade Bartolomeu, Aloisio-
Autor(es): dc.creatorDa Silva Filho, Luiz C.-
Autor(es): dc.creatorDa Fonseca, Luiz M.-
Autor(es): dc.creatorXimenes, Valdecir F.-
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Descrição: dc.descriptionCoordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)-
Descrição: dc.descriptionFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)-
Descrição: dc.descriptionConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)-
Descrição: dc.descriptionProcesso FAPESP: #2010/52327-5-
Descrição: dc.descriptionProcesso FAPESP: #2011/03017-6-
Descrição: dc.descriptionProcesso FAPESP: #2013/07600-3-
Descrição: dc.descriptionProcesso FAPESP: #2013/08784-0-
Descrição: dc.descriptionCNPq: #440503/2014-0-
Descrição: dc.descriptionBackground: Coumarin derivatives as dihydrocoumarins have been reported to have multiple biological activities, such as antioxidant and anti-inflammatory properties. Apocynin (APO), which is a substituted-methoxy-catechol, is the most commonly used inhibitor of the multienzymatic complex NADPH-oxidase. Objective: To increase the potency of APO as an NADPH oxidase inhibitor and its antioxidant and anti-inflammatory activities, we synthesized a compound by combining the structural features of a dihydrocoumarin and APO. Method: The dihydrocoumarin-apocynin derivative (HCA) was synthesized and evaluated in antioxidant and cell-based bioassays and compared with APO. Results: We found that HCA (IC50 = 10 μM) acted as an inhibitor of NADPH oxidase (ex vivo assays) and was more potent than APO (EC50 > 10 μM). The inhibitory effect on NADPH oxidase was not related to simple radical scavenger activity. HCA was also a more effective radical scavenger than APO, as verified in the DPPH (EC50 = 50.3 versus EC50 > 100 μM), triene degradation (slope AUC/concentration 759 ± 100 versus 101 ± 15) and FRAP (slope 0.159 versus 0.015) assays. The tested compound demonstrated a similar activity as an inhibitor of the oxidative damage provoked by peroxyl radicals in erythrocyte membranes. Conclusion: HCA showed superior capacity as inhibitor of NADPH oxidase and antioxidant activity. These findings show that HCA could be an improved substitute for APO and deserves further in vivo anti-inflammatory studies.-
Formato: dc.format93-100-
Idioma: dc.languageen-
Relação: dc.relationMedicinal Chemistry-
Relação: dc.relation0,372-
Direitos: dc.rightsclosedAccess-
Palavras-chave: dc.subjectAntioxidant-
Palavras-chave: dc.subjectApocynin-
Palavras-chave: dc.subjectCoumarin-
Palavras-chave: dc.subjectNADPH oxidase-
Palavras-chave: dc.subjectNeutrophils-
Título: dc.titleSynthesis, antioxidant and anti-inflammatory properties of an apocynin-derived dihydrocoumarin-
Tipo de arquivo: dc.typelivro digital-
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