Quantifying the hydrogen-bond propensity of drugs and its relationship with Lipinski's rule of five

Haritha, Mambatta; Sreerag, Manikandan; Suresh, Cherumuttathu H.

doi:10.1039/d3nj05476d

Cited by 4 publications

(1 citation statement)

References 55 publications

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“…The log p values of compounds A6 (2.269) and E3 (3.280) were both less than 5, indicating that they could be easily absorbed and transported in the plants . Surprisingly, compound A6 had eight HBAs (no more than 10) and four HBDs (no more than five), which complied with the Ribinski rule . Therefore, compound A6 can be used as a promising candidate for the development of new antiviral drugs targeting TMV CP.…”

Section: Resultsmentioning

confidence: 97%

Ferulic Acid Dimers as Potential Antiviral Agents by Inhibiting TMV Self-Assembly

Tai,

Zhang,

et al. 2024

J. Agric. Food Chem.

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A series of ferulic acid dimers were designed, synthesized, and evaluated for anti-TMV activity. Biological assays demonstrated that compounds A6, E3, and E5 displayed excellent inactivating against tobacco mosaic virus (TMV) with EC 50 values of 62.8, 94.4, and 85.2 μg mL −1 , respectively, which were superior to that of ningnanmycin (108.1 μg mL −1 ). Microscale thermophoresis indicated that compounds A6, E3, and E5 showed strong binding capacity to TMV coat protein with binding affinity values of 1.862, 3.439, and 2.926 μM, respectively. Molecular docking and molecular dynamics simulation revealed that compound A6 could firmly bind to the TMV coat protein through hydrogen and hydrophobic bonds. Transmission electron microscopy and self-assembly experiments indicated that compound A6 obviously destroyed the integrity of the TMV particles and blocked the virus from infecting the host. This study revealed that A6 can be used as a promising leading structure for the development of antiviral agents by inhibiting TMV self-assembly.

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Section: Resultsmentioning

confidence: 97%

Ferulic Acid Dimers as Potential Antiviral Agents by Inhibiting TMV Self-Assembly

Tai,

Zhang,

et al. 2024

J. Agric. Food Chem.

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Unveiling Drug Discovery Insights Through Molecular Electrostatic Potential Analysis

Haritha,

Suresh

2024

WIREs Comput Mol Sci

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Molecular electrostatic potential (MESP) analysis has emerged as a pivotal tool in drug discovery, providing insights into molecular reactivity and noncovalent interactions essential for drug function. While widely used MESP‐on‐isodensity surface analysis offers interpretations of electron‐rich or deficient regions of a drug molecule, the MESP topology parameters such as spatial minimum (Vmin) and MESP at nuclei (Vn) provide a quantitative understanding. The investigation into the correlation between MESP parameters and various molecular properties such as lipophilicity, pKa (acidity/basicity), conformations, and tautomeric forms is crucial for understanding the impact on biological activity of drugs and facilitating drug design. Moreover, MESP topology analysis serves as a fundamental tool in elucidating the pharmacological behavior of compounds and optimizing their therapeutic efficacy. A quantitative study utilizing Vn parameters to assess the hydrogen bond propensity of a drug presents a novel strategy for investigating drug‐receptor interactions with increased precision. The qualitative and quantitative analysis of the MESP features of various drugs, including their applications in cancer, tuberculosis, tumors, inflammation, and infectious diseases such as malaria, bacterial infections, fungal infections, and viral infections, is conducted in this review.

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Novel naphthoquinones as potent aromatase inhibitors: Synthesis, anticancer, and in silico studies

Leechaisit,

Mahalapbutr,

Suriya

et al. 2024

Journal of Molecular Structure

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Quantifying the hydrogen-bond propensity of drugs and its relationship with Lipinski's rule of five

Abstract: We define Vn as the molecular electrostatic potential (MESP) at the nucleus of a free atom, calculated excluding the contribution of that nucleus charge. The Vn value at the nucleus...

Cited by 4 publications

References 55 publications

Ferulic Acid Dimers as Potential Antiviral Agents by Inhibiting TMV Self-Assembly

Ferulic Acid Dimers as Potential Antiviral Agents by Inhibiting TMV Self-Assembly

Unveiling Drug Discovery Insights Through Molecular Electrostatic Potential Analysis

Novel naphthoquinones as potent aromatase inhibitors: Synthesis, anticancer, and in silico studies

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