ArticleBiochemical pharmacology2013
3,4-Dihydroxy-5-nitrobenzaldehyde (DHNB) is a potent inhibitor of xanthine oxidase: a potential therapeutic agent for treatment of hyperuricemia and gout.
Article in Biochemical pharmacology, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 18 papers.
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Who cites it
18 citing papers in PubMed, 79 citations in OpenAlex.
- Heterocyclic compounds as xanthine oxidase inhibitors for the management of hyperuricemia: synthetic strategies, structure-activity relationship and molecular docking studies (2018-2024).RSC medicinal chemistry · 2024Review
- Effect of Hydroxytyrosol Derivatives of Donepezil on the Activity of Enzymes Involved in Neurodegenerative Diseases and Oxidative Damage.Molecules (Basel, Switzerland) · 2024Article
- Targeting Neutrophil Extracellular Traps in Gouty Arthritis: Insights into Pathogenesis and Therapeutic Potential.Journal of inflammation research · 2024Review
- Past, present and future of xanthine oxidase inhibitors: design strategies, structural and pharmacological insights, patents and clinical trials.RSC medicinal chemistry · 2023Review
- Novel Reversible Inhibitors of Xanthine Oxidase Targeting the Active Site of the Enzyme.Antioxidants (Basel, Switzerland) · 2023Article
- Phenolic Profile, Antioxidant, Antidiabetic, and Antigout Potential of Stem Extracts of Four Sweet Cherry Cultivars.Evidence-based complementary and alternative medicine : eCAM · 2023Article
- Anti-hyperuricemia effect of hesperetin is mediated by inhibiting the activity of xanthine oxidase and promoting excretion of uric acid.Frontiers in pharmacology · 2023Article
- Effect of Bining decoction on gouty nephropathy: a network pharmacology analysis and preliminary validation of gut microbiota in a mouse model.Annals of translational medicine · 2022Article
- Synergistic Impacts ofBioMed research international · 2022Article
- A theoretical study of allopurinol drug sensing by carbon and boron nitride nanostructures: DFT, QTAIM, RDG, NBO and PCM insights.RSC advances · 2021Article
- Anti-Gout Effects of the Medicinal FungusFrontiers in pharmacology · 2021Article
- The Role of Oxidative Stress in Hyperuricemia and Xanthine Oxidoreductase (XOR) Inhibitors.Oxidative medicine and cellular longevity · 2021Review
- Clinical Effects of Xanthine Oxidase Inhibitors in Hyperuricemic Patients.Medical principles and practice : international journal of the Kuwait University, Health Science Centre · 2021Review
- From Xanthine Oxidase Inhibition toEvidence-based complementary and alternative medicine : eCAM · 2020Review
- Suppressing Effect of 2-Nitrobenzaldehyde on Singlet Oxygen Generation, Fatty Acid Photooxidation, and Dye-Sensitizer Degradation.Antioxidants (Basel, Switzerland) · 2018Article
- The Effect of Xanthine Oxidase Inhibitors on Blood Pressure and Renal Function.Current hypertension reports · 2017Review
- An evidence-based review on urate-lowering treatments: implications for optimal treatment of chronic hyperuricemia.Vascular health and risk management · 2017Review
- Hyperuricemia-Related Diseases and Xanthine Oxidoreductase (XOR) Inhibitors: An Overview.Medical science monitor : international medical journal of experimental and clinical research · 2016Review
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
Hyperuricemia, excess of uric acid in the blood, is a clinical problem that causes gout and is also considered a risk factor for cardiovascular disease. The enzyme xanthine oxidase (XO) produces uric acid during the purine metabolism; therefore, discovering novel XO inhibitors is an important strategy to develop an effective therapy for hyperuricemia and gout. We found that 3,4-dihydroxy-5-nitrobenzaldehyde (DHNB), a derivative of the natural substance protocatechuic aldehyde, potently inhibited XO activity with an IC₅₀ value of 3 μM. DHNB inhibited XO activity in a time-dependent manner, which was similar to that of allopurinol, a clinical XO inhibitory drug. DHNB displayed potent mixed-type inhibition of the activity of XO, and showed an additive effect with allopurinol at the low concentration. Structure-activity relationship studies of DHNB indicated that the aldehyde moiety, the catechol moiety, and nitration at C-5 were required for XO inhibition. DHNB interacted with the molybdenum center of XO and was slowly converted to its carboxylic acid at a rate of 10⁻¹⁰ mol/L/s. In addition, DHNB directly scavenged free radical DPPH and ROS, including ONOO⁻ and HOCl. DHNB effectively reduced serum uric acid levels in allantoxanamide-induced hyperuricemic mice. Furthermore, mice orally given a large dose (500 mg/kg) of DHNB did not show any side effects, while 42% of allopurinol (500 mg/kg)-treated mice died and their offspring lost their fur. Thus, DHNB could be an outstanding candidate for a novel XO inhibitory drug that has potent activity and low toxicity, as well as antioxidant activity and a distinct chemical structure from allopurinol.
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