Characterization of the interaction of glycyrrhizin and glycyrrhetinic acid with bovine serum albumin by spectrophotometric-gradient flow injection titration technique and molecular modeling simulations

Manouchehri, Firouzeh; Izadmanesh, Yahya; Ghasemi, Jahan B.

doi:10.1016/j.ijbiomac.2017.02.106

Cited by 10 publications

(5 citation statements)

References 78 publications

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“…This enhances the metabolic stability of the compounds and extends their duration of action within the body. 22 In compound 3e , the fluorine atom also engages in halogen interactions with His263, which bears structural significance similar to weak hydrogen bonding. Additionally, the benzene ring connected to the fluorine in 3e forms pi–alkyl conjugation with Ala286 and Val283, pi–pi stacked/T-shaped hydrophobic interactions with His 85 and His263.…”

Section: Resultsmentioning

confidence: 99%

Design, synthesis, and inhibitory activity of hydroquinone ester derivatives against mushroom tyrosinase

Xie,

Han,

Jiang

et al. 2024

RSC Adv.

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Section: Resultsmentioning

confidence: 99%

Design, synthesis, and inhibitory activity of hydroquinone ester derivatives against mushroom tyrosinase

Xie,

Han,

Jiang

et al. 2024

RSC Adv.

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“…These findings indicate an increase in hydrophobicity and a decrease in polarity surrounding the aromatic amino acids (TRP and TYR) of the protein. [ 31,33–37 ]…”

Section: Resultsmentioning

confidence: 99%

“…[3,23,28,[30][31][32] ity and a decrease in polarity surrounding the aromatic amino acids (TRP and TYR) of the protein. [31,[33][34][35][36][37] The interaction between the HCQ/SM mixture and HSA at different temperatures was analyzed using Equation (1), yielding the values of K SV are 1.71 × 10 5 , 1.41 × 10 5 , and 1.23 × 10 5 (L mol −1 ) at 298 K, 310 K, and 318 K, respectively, and the number of binding sites n is almost 1. These data suggest that a static quenching technique is most likely the mechanism used to quench the fluorescence of HSA by HCQ/SM because K SV decreased with increasing temperature.…”

Section: Circular Dichroism (Cd) Spectroscopymentioning

confidence: 99%

Spectroscopic investigation and structural simulation in human serum albumin with hydroxychloroquine/Silybum marianum and a possible potential COVID‐19 drug candidate

Tekyeh,

Shushtarian,

Bakhsh

et al. 2024

Archiv der Pharmazie

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In this study, the interaction between human serum albumin (HSA) and the hydroxychloroquine/Silybum marianum (HCQ/SM) mixture was investigated using various techniques. The observed high binding constant (Kb) and Stern–Volmer quenching constant (KSV) indicate a strong binding affinity between the HCQ/SM mixture and HSA. The circular dichroism (CD) analysis revealed that HCQ/SM induced conformational changes in the secondary structure of HSA, leading to a decrease in the α‐helical content. UV‐Vis analysis exhibited a slight redshift, indicating that the HCQ/SM mixture could adapt to the flexible structure of HSA. The experimental results demonstrated the significant conformational changes in HSA upon binding with HCQ/SM. Theoretical studies were carried out using molecular dynamics simulation via the Gromacs simulation package to explore insights into the drug interaction with HSA‐binding sites. Furthermore, molecular docking studies demonstrated that HCQ/SM‐HSA exhibited favorable docking scores with the receptor (5FUZ), suggesting a potential therapeutic relevance in combating COVID‐19 with a value of −6.24 kcal mol−1. HCQ/SM exhibited stronger interaction with both SARS‐CoV‐2 virus main proteases compared to favipiravir. Ultimately, the experimental data and molecular docking analysis presented in this research offer valuable insights into the pharmaceutical and biological properties of HCQ/SM mixtures when interacting with serum albumin.

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Section: Resultsmentioning

confidence: 99%

“…Besides, GA was reported to interact with albumin [8,9]; this could possibly inhibit the evaluation of GA's action using mAb6D6 and the quantification of GA in the serum in vivo. Indeed, to evaluate the level of GA in the serum using ELISA, Itoh and Mizugaki et al have reported that pretreatment with ibuprofen is an useful method to detect and quantify the serum albumin-bound GA using ELISA, with an anti-GA monoclonal antibody that they had established before [10,11].…”

Section: Preparation Of Monoclonal Antibody Against Gamentioning

confidence: 99%

Immunological validation of the pharmacological and anti‐allergic action of glycyrrhetinic acid from Glycyrrhizae Radix

Hisaka

Murase

Kishi

et al. 2021

Traditional & Kampo Medicine

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Aim Glycyrrhetinic acid (GA) is an important and active metabolite derived from glycyrrhizin (GL) in Glycyrrhizae Radix (GR) that induces anti‐allergic, anti‐inflammatory, anti‐oxidant, anti‐viral, and anti‐microbial effects in vivo. To validate these beneficial actions of GA as an active compound of GR in vivo, we prepared a monoclonal antibody against GA. Methods The monoclonal antibody, mAb6D6, was prepared and evaluated for cross‐reactivity with GA and its analogs using competitive enzyme‐linked immunosorbent assay. Subsequently, mAb6D6 was used to validate the anti‐allergic action of GA, which was orally administered as GL or hot water extracts of GR, in the IgE‐mediated passive cutaneous anaphylaxis model for immediate hypersensitivity and contact hypersensitivity model. Results MAb6D6 specifically identified GA and had no reactivity against other oleanane‐type compounds and endogenous steroids. This antibody could neutralise the anti‐allergic action of GA in both models in which mice were orally treated with GL or extracts of GR after intravenous injection of the antibody. Conclusion MAb6D6 neutralised the activity of GA in vivo. Therefore, it is essential to analyse the role of GA from GR in Kampo medicine and elucidate its mechanism of action.

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Characterization of the interaction of glycyrrhizin and glycyrrhetinic acid with bovine serum albumin by spectrophotometric-gradient flow injection titration technique and molecular modeling simulations

Cited by 10 publications

References 78 publications

Design, synthesis, and inhibitory activity of hydroquinone ester derivatives against mushroom tyrosinase

Design, synthesis, and inhibitory activity of hydroquinone ester derivatives against mushroom tyrosinase

Spectroscopic investigation and structural simulation in human serum albumin with hydroxychloroquine/Silybum marianum and a possible potential COVID‐19 drug candidate

Immunological validation of the pharmacological and anti‐allergic action of glycyrrhetinic acid from Glycyrrhizae Radix

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