Cited by 149Free Radicals and AntioxidantsBioactive Compounds and Antitumor AgentsRedox biology and oxidative stress

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Apocynin: Chemical and Biophysical Properties of a NADPH Oxidase Inhibitor

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Petrônio, Maicon, Zeraik, Maria, Fonseca, Luiz, Ximenes, Valdecir·2013·Molecules

DOI 10.3390/molecules18032821PMC PMC6269682

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Abstract

Apocynin is the most employed inhibitor of NADPH oxidase (NOX), a multienzymatic complex capable of catalyzing the one-electron reduction of molecular oxygen to the superoxide anion. Despite controversies about its selectivity, apocynin has been used as one of the most promising drugs in experimental models of inflammatory and neurodegenerative diseases. Here, we aimed to study the chemical and biophysical properties of apocynin. The oxidation potential was determined by cyclic voltammetry (Epa = 0.76V), the hydrophobicity index was calculated (logP = 0.83) and the molar absorption coefficient was determined (e275nm = 1.1 × 104 M−1 cm−1). Apocynin was a weak free radical scavenger (as measured using the DPPH, peroxyl radical and nitric oxide assays) when compared to protocatechuic acid, used here as a reference antioxidant. On the other hand, apocynin was more effective than protocatechuic acid as scavenger of the non-radical species hypochlorous acid. Apocynin reacted promptly with the non-radical reactive species H2O2 only in the presence of peroxidase. This finding is relevant, since it represents a new pathway for depleting H2O2 in cellular experimental models, besides the direct inhibition of NADPH oxidase. This could be relevant for its application as an inhibitor of NOX4, since this isoform produces H2O2 and not superoxide anion. The binding parameters calculated by fluorescence quenching showed that apocynin binds to human serum albumin (HSA) with a binding affinity of 2.19 × 104 M−1. The association did not alter the secondary and tertiary structure of HSA, as verified by synchronous fluorescence and circular dichroism. The displacement of fluorescent probes suggested that apocynin binds to site I and site II of HSA. Considering the current biomedical applications of this phytochemical, the dissemination of these chemical and biophysical properties can be very helpful for scientists and physicians interested in the use of apocynin.

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Authors: Petrônio, M., Zeraik, M., Fonseca, L., & Ximenes, V.
Affiliations: Universidade Estadual Paulista (Unesp) (BR)
Corresponding author: Ximenes, Valdecir
ORCID: Petrônio, Maicon
Zeraik, Maria
Ximenes, Valdecir
Venue: Molecules
Publisher: MDPI AG
Published: 2013-03-01
Volume: 18
Issue: 3
Pages: 2821-2839
ISSN: 1420-3049 (ISSN-L)
DOI: 10.3390/molecules18032821
PMC: PMC6269682
OpenAlex: W2036509107
Cited by: 149
References: 49
Citations by year: 2026: 8 · 2025: 12 · 2024: 8 · 2023: 11 · 2022: 14 · 2021: 14 · 2020: 9 · 2019: 12 · 2018: 11 · 2017: 11 · 2016: 6 · 2015: 12 · 2014: 14 · 2013: 7
FWCI: 5.91
Type: journal article
Language: en
Open access: gold
doi.org
Licence: cc-by
creativecommons.org/licenses/by/3.0/ (vor)
Locations: Molecules (publishedVersion, cc-by)
Europe PMC (PubMed Central) (publishedVersion, cc-by)
PubMed Central (publishedVersion, cc-by)
PubMed (publishedVersion)
Acervo Digital da Universidade Estadual Paulista (Universidade Estadual Paulista) (submittedVersion, other-oa)
Americanae (AECID Library) (submittedVersion, other-oa)
DOAJ (DOAJ: Directory of Open Access Journals) (submittedVersion, cc-by-sa)
LA Referencia (Red Federada de Repositorios Institucionales de Publicaciones Científicas) (submittedVersion, other-oa)
Funders: Fundação de Amparo à Pesquisa do Estado de São Paulo
Conselho Nacional de Desenvolvimento Científico e Tecnológico
Topics: Physical Sciences › Chemistry › Organic Chemistry › Free Radicals and Antioxidants
Life Sciences › Pharmacology, Toxicology and Pharmaceutics › Toxicology › Bioactive Compounds and Antitumor Agents
Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Redox biology and oxidative stress
Keywords: apocynin, NADPH oxidase inhibitors, NOX4, superoxide, hydrogen peroxide scavenging, free radical scavenging, hypochlorous acid, protocatechuic acid, human serum albumin binding, fluorescence quenching, antioxidant activity, physicochemical properties
MeSH terms: Acetophenones, Enzyme Inhibitors, Hydrogen Peroxide, Hydrogen-Ion Concentration, Hypochlorous Acid, Kinetics, Oxidation-Reduction, Free Radical Scavengers, NADPH Oxidases, Hydrophobic and Hydrophilic Interactions

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Apocynin: Chemical and Biophysical Properties of a NADPH Oxidase Inhibitor

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