A Multi-Spectroscopic and Molecular Docking Analysis of the Biophysical Interaction between Food Polyphenols, Urolithins, and Human Serum Albumin

被引:0
作者
Zelenovic, Nevena [1 ]
Ristic, Predrag [2 ]
Polovic, Natalija [2 ]
Todorovic, Tamara [2 ]
Kojadinovic, Milica [3 ]
Popovic, Milica [2 ]
机构
[1] Univ Belgrade, Inst Chem Technol & Met, Natl Inst Republ Serbia, Njegoseva 12, Belgrade 11000, Serbia
[2] Univ Belgrade, Fac Chem, Studentski trg 12-16, Belgrade 11000, Serbia
[3] Univ Belgrade, Inst Med Res, Natl Inst Republ Serbia, Tadeusa Koscuska 1, Belgrade 11000, Serbia
来源
MOLECULES | 2024年 / 29卷 / 18期
关键词
urolithins; human serum albumin; binding affinity; fluorescence spectroscopy; Fourier transform infrared spectroscopy; molecular docking; ELLAGIC ACID; TEST SET; BINDING; DRUG; FLUORESCENCE; SITES;
D O I
10.3390/molecules29184474
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Secondary polyphenol metabolites, urolithins (UROs), have anti-oxidative, anti-inflammatory, and antidiabetic properties. Therefore, their biological activity relies on blood transport via human serum albumin (HSA) and tissue distribution. The main goal we set was to investigate the interaction between HSA and different URO (URO A, URO B, URO C, URO D, and glucuronidated URO A and B) using a combination of multi-spectroscopic instrumental and in silico approaches. The fluorescence spectroscopy revealed that URO can quench the naturally occurring fluorescence of HSA in a concentration-dependent manner. The HSA fluorescence was quenched by both a static and dynamic mechanism. The results showed that free UROs bind to HSA with higher affinity than their conjugated forms. CD spectroscopy and FTIR revealed that the alpha-helical structure of HSA is preserved. The calculated Gibbs free energy change indicates that the URO-HSA complex forms spontaneously. There is a single binding site on the HSA surface. The molecular docking results indicated that unconjugated Uro binds to Sudlow I, while their conjugation affects this binding site, so in the conjugated form, they bind to the cleft. Docking experiments indicate that all UROs are capable of binding to both thyroxine recognition sites of ligand-bound HSA proteins. Examining interactions under the following conditions (298 K, 303 K, and 310 K, pH 7.4) is of great importance for determining the pharmacokinetics of these bioactive compounds, as the obtained results can be used as a basis for modulating the potential dosing regimen.
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页数:23
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共 53 条
  • [1] CONFORMATIONAL-ANALYSIS .130. MM2 - HYDROCARBON FORCE-FIELD UTILIZING V1 AND V2 TORSIONAL TERMS
    ALLINGER, NL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (25) : 8127 - 8134
  • [2] Physiological Relevance of the Antiproliferative and Estrogenic Effects of Dietary Polyphenol Aglycones versus Their Phase-II Metabolites on Breast Cancer Cells: A Call of Caution
    Angeles Avila-Galvez, Maria
    Carlos Espin, Juan
    Gonzalez-Sarrias, Antonio
    [J]. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2018, 66 (32) : 8547 - 8555
  • [3] Avila-Gálvez MA, 2019, FOOD FUNCT, V10, P3135, DOI [10.1039/c9fo00298g, 10.1039/C9FO00298G]
  • [4] Announcing the worldwide Protein Data Bank
    Berman, H
    Henrick, K
    Nakamura, H
    [J]. NATURE STRUCTURAL BIOLOGY, 2003, 10 (12) : 980 - 980
  • [5] Urolithins, Intestinal Microbial Metabolites of Pomegranate Ellagitannins, Exhibit Potent Antioxidant Activity in a Cell-Based Assay
    Bialonska, Dobroslawa
    Kasimsetty, Sashi G.
    Khan, Shabana I.
    Ferreira, Daneel
    [J]. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2009, 57 (21) : 10181 - 10186
  • [6] CORRECTION FOR LIGHT-ABSORPTION IN FLUORESCENCE STUDIES OF PROTEIN-LIGAND INTERACTIONS
    BIRDSALL, B
    KING, RW
    WHEELER, MR
    LEWIS, CA
    GOODE, SR
    DUNLAP, RB
    ROBERTS, GCK
    [J]. ANALYTICAL BIOCHEMISTRY, 1983, 132 (02) : 353 - 361
  • [7] Biological Significance of Urolithins, the Gut Microbial Ellagic Acid-Derived Metabolites: The Evidence So Far
    Carlos Espin, Juan
    Larrosa, Mar
    Teresa Garcia-Conesa, Maria
    Tomas-Barberan, Francisco
    [J]. EVIDENCE-BASED COMPLEMENTARY AND ALTERNATIVE MEDICINE, 2013, 2013
  • [8] New Insights About Albumin and Liver Disease
    Carvalho, Joana R.
    Machado, Mariana Verdelho
    [J]. ANNALS OF HEPATOLOGY, 2018, 17 (04) : 547 - 560
  • [9] Metabolism of antioxidant and chemopreventive ellagitannins from strawberries, raspberries, walnuts, and oak-aged wine in humans:: Identification of biomarkers and individual variability
    Cerdá, B
    Tomás-Barberán, FA
    Espín, JC
    [J]. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2005, 53 (02) : 227 - 235
  • [10] Recent Advances and Perspectives on the Health Benefits of Urolithin B, A Bioactive Natural Product Derived From Ellagitannins
    Chen, Peng
    Guo, Zhiei
    Chen, Fuchao
    Wu, Yue
    Zhou, Benhong
    [J]. FRONTIERS IN PHARMACOLOGY, 2022, 13