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Apocynin: Chemical and Biophysical Properties of a NADPH Oxidase Inhibitor
Open accessAbstract
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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“Finally, it must be noted that arginases play an important role in the regulation of l-arginine levels (144, 259, 734, 804).”
From Sources of Vascular Nitric Oxide and Reactive Oxygen Species and Their Regulation (2019) · cites this paper as [734]
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Cites
Principles of Fluorescence Spectroscopy
Lakowicz, J. R. (1999) · Springer eBooks · doi:10.1007/978-1-4757-3061-6 · Cited by 26,948
Use of a Free Radical Method to Evaluate Antioxidant Activity
Brand-Williams, W., Cuvelier, M. E., & Berset, C. (1995) · LWT - Food Science and Technology · doi:10.1016/s0023-6438(95)80008-5 · Cited by 25,994
Principles of Fluorescence Spectroscopy
Lakowicz, J. R. (2006) · Springer eBooks · doi:10.1007/978-0-387-46312-4 · Cited by 19,795
How to measure and predict the molar absorption coefficient of a protein
Pace, C., Vajdos, F., Fee, L. R., Grimsley, G., & Gray, T. (1995) · Protein Science · doi:10.1002/pro.5560041120 · Cited by 3,924
Quenching of fluorescence by oxygen. Probe for structural fluctuations in macromolecules
Lakowicz, J. R., & Weber, G. (1973) · Biochemistry · doi:10.1021/bi00745a020 · Cited by 2,795
Human serum albumin: From bench to bedside
Fanali, G., di Masi, A., Trezza, V., Marino, M., Fasano, M., & Ascenzi, P. (2011) · Molecular Aspects of Medicine · doi:10.1016/j.mam.2011.12.002 · Cited by 2,008
FLUORESCENCE AND THE LOCATION OF TRYPTOPHAN RESIDUES IN PROTEIN MOLECULES
Burstein, E. A., Vedenkina, N. S., & Mn, I. (1973) · Photochemistry and Photobiology · doi:10.1111/j.1751-1097.1973.tb06422.x · Cited by 1,187
Ghose, A. K., & Crippen, G. M. (1987) · Journal of Chemical Information and Computer Sciences · doi:10.1021/ci00053a005 · Cited by 804
Apocynin Is Not an Inhibitor of Vascular NADPH Oxidases but an Antioxidant
Heumüller, S., Wind, S., Barbosa-Sicard, E., Schmidt, H. H. H. W., Busse, R., Schröder, K., & Brandes, R. P. (2008) · Hypertension · doi:10.1161/hypertensionaha.107.100214 · Cited by 735
Brown, R., James, C., Henderson, L. A., & Macefield, V. G. (2012) · Frontiers in Physiology · doi:10.3389/fphys.2012.00394 · Cited by 730
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Bhatia, A., Thakur, S., Kohal, R., Brar, S., Gupta, G. D., & Verma, S. K. (2025) · Fitoterapia · doi:10.1016/j.fitote.2025.106558 · Cited by 8
Frara, N. A., Giaddui, D., Braverman, A. S., Jawawdeh, K., Wu, C., Ruggieri, M. R., & Barbe, M. F. (2023) · PLoS ONE · doi:10.1371/journal.pone.0287212 · Cited by 7
Kuru-Yaşar, R., Kuru, D., Şen, A., Şener, G., Ercan, F., & Yarat, A. (2021) · Turkish Journal of Ophthalmology · doi:10.4274/tjo.galenos.2021.27981 · Cited by 7
Guo, J. X., Yu, X., Liu, Y., Lu, L., Zhu, D., Zhang, Y., Li, L., Zhang, P., Gao, Q., Lu, X., et al. (2022) · Reproductive Toxicology · doi:10.1016/j.reprotox.2022.08.009 · Cited by 7
Characteristics of Japanese Mint Extracts Obtained by Subcritical-water Treatment
Nomura, S., Lee, W., Konishi, M., Saitoh, T., Murata, M., Ohtsu, N., Shimotori, Y., Kohari, Y., Nagata, Y., & Chiou, T. (2019) · Food Science and Technology Research · doi:10.3136/fstr.25.695 · Cited by 7
dos Reis, V. P., Setúbal, S. D. S., Ferreira, A. A. F. E., Santana, H. M., Silva, M. D. S., Sousa, O. D. O., Boeno, C. N., Soares, A. M., Zamunér, S. R., & Zuliani, J. P. (2022) · BioMed Research International · doi:10.1155/2022/5266211 · Cited by 6
Zahid, H. M., Ferdaus, M. Z., Ohara, H., Isomura, M., & Nabika, T. (2016) · Scientific Reports · doi:10.1038/srep36739 · Cited by 6
Hatcher, J. T., Gu, H., & Cheng, Z. J. (2015) · Oxidative Medicine and Cellular Longevity · doi:10.1155/2016/3686829 · Cited by 5
Davis, C. K., Bathula, S., Jeong, S., Arruri, V. K., Choi, J., Subramanian, S., Ostrom, C. M., & Vemuganti, R. (2024) · Experimental Neurology · doi:10.1016/j.expneurol.2024.114795 · Cited by 6
Feng, X., Liu, X., Wang, F., Zhang, X., Zhu, L., Shu, H., Wang, C., Duan, L., Wang, H., Ren, Q., et al. (2024) · Molecular Nutrition & Food Research · doi:10.1002/mnfr.202300871 · Cited by 5
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Higuera-Martínez, G., Arciniega-Martínez, I. M., Luna, R. A. J., Cárdenas‐Jaramillo, L. M., Levaro‐Loquio, D., Velásquez-Torres, M., Abarca‐Rojano, E., Reséndiz‐Albor, A. A., & Pacheco‐Yépez, J. (2023) · Biomedicines · doi:10.3390/biomedicines11082322 · Cited by 4
Sharma, S., Sharma, A., & Chauhan, R. S. (2024) · Journal of Biomolecular Structure and Dynamics · doi:10.1080/07391102.2024.2438358 · Cited by 4
The Effect of Apocynin on Motor and Cognitive Functions in Experimental Alzheimer’s disease.
Akyuva, Y., Onal, C., Parlakpınar, H., Gul, M., Çiğremiş, Y., Ates, T., & Kablan, Y. (2018) · Periodicum Biologorum · doi:10.18054/pb.v120i1.5975 · Cited by 4
Xu, X., Wang, Q., Liu, Z., Li, J., Wang, S., & Qian, L. (2026) · Antioxidants · doi:10.3390/antiox15050571 · Cited by 4
Ruiz-Hernández, A. A., Rouzaud‐Sández, O., Frı́as, J., Ayala-Zavala, J. F., Astiazarán‐García, H., Salazar‐López, N. J., López‐Saiz, C. M., Reé-Rodríguez, S. C. D. L., & Robles-Sánchez, R. M. (2023) · Journal of Functional Foods · doi:10.1016/j.jff.2023.105857 · Cited by 3
Yu, L., Gong, Y., Song, H., Lang, L., Yu, J., Ma, Y., Qu, Z., Zhang, X., Zou, X., Zhang, C., et al. (2025) · Journal of Ethnopharmacology · doi:10.1016/j.jep.2025.120034 · Cited by 4
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Michałkiewicz, S., Skorupa, A., Jakubczyk, M., & Bębacz, K. (2024) · Materials · doi:10.3390/ma17071593 · Cited by 2
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Lichitsky, B. V., Komogortsev, A. N., & Melekhina, V. G. (2022) · Molbank · doi:10.3390/m1357 · Cited by 2
Krupashree, K., & Rachitha, P. (2022) · Research Square · doi:10.21203/rs.3.rs-1478335/v1 · Cited by 2
Mevada, S., Patel, H., & Shukla, S. (2025) · Accreditation and Quality Assurance · doi:10.1007/s00769-025-01633-1 · Cited by 1
Skorupa, A., Jakubczyk, M., & Michałkiewicz, S. (2025) · Materials · doi:10.3390/ma18092044 · Cited by 1
Activities of apocynin in cytotoxicity assays of potential pathological relevance
Wong, S. P., Fong, V. H., & Vieira, A. V. (2015) · Biomedicine & Pharmacotherapy · doi:10.1016/j.biopha.2015.10.007 · Cited by 1
Md. Shaekh, F., Wan Maznah, W. I., Mohd Fadhlizil Fasihi, M. A., Shihab Uddin, A., Kamrul, R., Saiful Nizam, T., & Akm Moyeenul, H. (2023) · Medicine & health · doi:10.17576/mh.2023.1801.12 · Cited by 1
Lee, M. T. W., Mahy, W., & Rackham, M. D. (2021) · RSC Medicinal Chemistry · doi:10.1039/d1md00113b · Cited by 1
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Kapoor, M., Sharma, S., Sandhir, R., & Nehru, B. (2021) · Advances in Redox Research · doi:10.1016/j.arres.2021.100012 · Cited by 1
Villivalam, S. D., You, D., Ebert, S. M., Kim, J., Han, X., Palacios, H. H., Adams, C. M., & Kang, S. (2020) · bioRxiv (Cold Spring Harbor Laboratory) · doi:10.1101/2020.05.18.102400 · Cited by 1
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Bedford, F. L. (2021) · SSRN Electronic Journal · doi:10.2139/ssrn.3773896 · Cited by 1
Devine, I., Chen, Q., Ondrasik, R. M., Chau, W. L., Navitsky, K., Lau, O., Parker, C. W., Bartol, K. D., Casey, B., Barsotti, R., et al. (2013) · American Peptide Symposium (APS) · doi:10.17952/23aps.2013.00142
Guimarães, F. L. R. (2015) · Digital Library of Theses and Dissertations (Universidade de São Paulo) · doi:10.11606/d.39.2015.tde-02072015-093347
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Rozycki, M. (2015) · TSpace (University of Toronto)
Characterizing the Role of IL-1β in Macrophage Clearance of Citrobacter rodentium Infection
Bording‐Jorgensen, M. (2018) · ERA: Education and Research Archive (University of Alberta) · doi:10.7939/r3td9nq61
de Oliveira, C. C. (2018) · Digital Library of Theses and Dissertations (Universidade de São Paulo) · doi:10.11606/d.42.2019.tde-16082019-155417
Kim, J.-H., Jo, S., Lee, S. J., Yoo, G. M., Na, H. G., Choi, Y. S., Bae, C. H., Song, S., & Kim, Y. (2021) · Korean Journal of Otorhinolaryngology - Head and Neck Surgery · doi:10.3342/kjorl-hns.2021.00171
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Giongo, C. N., Lopes, V. F., Fortkamp, D., & Miranda, E. H. (2020) · PERIÓDICO TCHÊ QUÍMICA · doi:10.52571/ptq.v17.n34.2020.502_p34_pgs_478_501.pdf
Chan, S. M. H., Brassington, K., Almerdasi, S. A., Dobric, A., Luca, S. N. D., Coward‐Smith, M., Wang, H., Mou, K., Akhtar, A., Alateeq, R., et al. (2022) · doi:10.22541/au.167103364.45088107/v1
Reduction of oxidative damage in prostate tissue caused by radiation and/or chloroquine by apocynin
Ertik, O., Us, A. S., Bugan, I., Us, H., Cöremen, M., Bulan, Ö. K., & Yanardağ, R. (2024) · Free Radical Research · doi:10.1080/10715762.2024.2393147
NADPH oxidase, obesity, and metabolic syndrome: Therapeutic opportunity
Tikhonova, I. V., & Safronova, V. G. (2025) · Elsevier eBooks · doi:10.1016/b978-0-443-27370-4.00024-x
Xue, X., Liu, M., Almoallim, H. S. M., Alahmadi, T. A., & Wang, W. (2026) · Journal of Pharmaceutical Innovation · doi:10.1007/s12247-026-10577-z
Apocynin in Diabetes: Modulation of Oxidative Stress and Inflammatory Signaling
Khan, U. R., Otari, K. V., & Kale, A. Y. (2026) · Biosciences Biotechnology Research Asia · doi:10.13005/bbra/3517
Li, D., Wuerzberger‐Davis, S. M., Chen, Y., Phan, F. P., Yu, M., Lisiero, D. N., Aguilar, C. C., Cleven, T., Tejera, M. M., Khatri, P., et al. (2026) · The EMBO Journal · doi:10.1038/s44318-026-00875-0
Lee, K. S., Kim, S., Vinh, L. B., Han, J. S., Hwang, B. Y., Lee, M. K., & Lee, K. Y. (2026) · Antioxidants · doi:10.3390/antiox15081023
Arancibia, D., Lira, M., Alcota, B., Simirgiotis, M. J., Paredes, A., & Zárate, R. V. (2026) · Molecules · doi:10.3390/molecules31203765
Naseem, T., Khan, H., & Parvez, S. (2026) · Elsevier eBooks · doi:10.1016/b978-0-443-27544-9.00018-0
Metadata
- Authors
- Petrônio, M., Zeraik, M., Fonseca, L., & Ximenes, V.
- Affiliations
- Universidade Estadual Paulista (Unesp) (BR)
- Corresponding author
- Ximenes, Valdecir
- Venue
- Molecules
- Publisher
- MDPI AG
- Published
- 2013-03-01
- Volume
- 18
- Issue
- 3
- Pages
- 2821-2839
- ISSN
- 1420-3049 (ISSN-L)
- 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
- 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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