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Lapachol, a natural food component, interacts with human serum albumin: Insights of its impact on the pharmacokinetics of clinically used drugs

Lapachol (LAP), a natural 1,4-naphthoquinone used in popular medicine in South America, is an antioxidant and antimicrobial compound in teas and infusions and used as a food additive; however, its interactive profile with the main protein carrier of compounds in the human bloodstream (human serum al...

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Published in:International journal of biological macromolecules 2024-12, Vol.282 (Pt 6), p.137520, Article 137520
Main Authors: Almeida, Zaida L., Cruz, Pedro F., Costa, Telma, Netto-Ferreira, José Carlos, de Lima, Marco Edilson Freire, da Silva, Márcia Barbosa, Serpa, Carlos, Chaves, Otávio A.
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container_issue Pt 6
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container_title International journal of biological macromolecules
container_volume 282
creator Almeida, Zaida L.
Cruz, Pedro F.
Costa, Telma
Netto-Ferreira, José Carlos
de Lima, Marco Edilson Freire
da Silva, Márcia Barbosa
Serpa, Carlos
Chaves, Otávio A.
description Lapachol (LAP), a natural 1,4-naphthoquinone used in popular medicine in South America, is an antioxidant and antimicrobial compound in teas and infusions and used as a food additive; however, its interactive profile with the main protein carrier of compounds in the human bloodstream (human serum albumin, HSA) was not still characterized. Additionally, the impact of LAP in binding clinically drugs to albumin is still unknown. Thus, the present work describes the interaction HSA:LAP using different biophysical techniques, i.e., 1H saturation-transfer difference nuclear magnetic resonance (1H STD-NMR), isothermal titration calorimetry (ITC), steady-state and time-resolved fluorescence measurements combined with molecular docking calculations. LAP interacts with subdomain region IIA (site I), mainly driven by enthalpy effects, while subdomain region IB (site III) was identified as the second binding site, mainly driven by entropy effects. The binding is spontaneous, strong (binding constant average, Kaverage ≈ 4.45 × 105 M−1), and there is a positive cooperativity in the presence of ibuprofen, with the LAP structure fully buried into the protein cavities. Overall, LAP might impact the residence time (pharmacokinetic profile) of drugs that bind to subdomains regions IIA and IB of albumin, e.g., warfarin, phenylbutazone, diflunisal, naproxen, camptothecin, doxorubicin, daunorubicin, suramin, and tyrosine kinase inhibitors. [Display omitted]
doi_str_mv 10.1016/j.ijbiomac.2024.137520
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subjects Binding Sites
Calorimetry
Drug-displacement
HSA-binding
Humans
Molecular Docking Simulation
Naphthoquinones - chemistry
Naphthoquinones - metabolism
Naphthoquinones - pharmacokinetics
Natural food ingredients
Protein Binding
Serum Albumin, Human - chemistry
Serum Albumin, Human - metabolism
Thermodynamics
title Lapachol, a natural food component, interacts with human serum albumin: Insights of its impact on the pharmacokinetics of clinically used drugs
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