An Overview on the Anticancer Potential of Punarnavine: Prediction of Drug-Like Properties

Ahmad, Imad; Khan, Haroon; Amin, Muhammad Usman; Khalid, Shah; Behl, Tapan; Rahman, Najeeb

doi:10.32604/oncologie.2021.018296

Cited by 10 publications

(15 citation statements)

References 50 publications

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“…Te H-bond acceptor and donor are within accurately strict limit, except C3 being within limit but a little higher nRB and nHBA (Table 2). Oral drugs have fewer H-bond acceptors, donors, and rotatable bonds [20].…”

Section: Discussionmentioning

confidence: 99%

“…Te SwissADME database has assigned to TZDs derivatives the scores of 3.16 to 3.84 which suggest easy step reactions of synthesis. Te difcult synthetic approaches for those molecules having a score of 10 [20].…”

Section: Discussionmentioning

confidence: 99%

“…Compounds with pharmacokinetic characteristics that enable them to endure the end of human phase I clinical trials are referred to as drug-like chemical space [19]. Te SwissADMET database was used to estimate the physicochemical qualities, such as lipophilicity and water solubility, pharmacokinetic profle, drug likeness, and medicinal chemistry of the compounds [20,21]. Te 2D structures were drawn in the database which also allowed for a string-based search (Table 1).…”

Section: Characterizationmentioning

confidence: 99%

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Synthesis, Characterization, and Pharmacokinetic Studies of Thiazolidine-2,4-Dione Derivatives

Ansari

Khan

Jan

et al. 2023

Journal of Chemistry

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Various derivatives of thiazolidine-2,4-dione (C1–C5) were designed and synthesized by chemical reaction with 4-nitrobenzaldehyde using Knoevenagel reaction conditions which results in the reduction of nitro group to amine and further modification results in target compounds. The chemical structures of all the 2,4-thiazolidinedione derivatives have been elucidated by 1H and 13C NMR spectroscopy. These compounds were further characterized by in silico ADME (absorption, distribution, metabolism, and excretion) studies. The pharmacokinetic properties were assessed by SwissADME software. The in silico ADME (absorption, distribution, metabolism, and excretion) assessment reveals that all derivatives (C1 to C5) have 5 to 7 rotatable bonds. Lipophilicity and water solubility showed that C1, C2, and C4 are water soluble except for C3 and C5 which are moderately soluble. All the compounds have high GI absorption except C3. None of the derivatives are blood-brain barrier permeant. Drug metabolism of TZDs derivatives showed that C3 was identified as an inhibitor of CYP2C9 and C5 as an inhibitor of CYP1A2 and CYP2C19. Drug likeness properties indicate that C1 has only one violation of the Ghose rule while C3 has violations in the Ghose and Egan rules. The in silico pharmacokinetic studies revealed high GI absorption and the inability to pass blood-brain barrier which can be further assessed by in vitro and in vivo antihyperglycemic activity. This study will contribute to providing TZDs derivatives with an improved pharmacokinetic profile and decreased toxicity.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Section: Characterizationmentioning

confidence: 99%

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Synthesis, Characterization, and Pharmacokinetic Studies of Thiazolidine-2,4-Dione Derivatives

Ansari

Khan

Jan

et al. 2023

Journal of Chemistry

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“…Tis flter is justifed, however, by the potential of in vitro screening due to the potency of ligand afnity drops at a rate of, on average, 0.5 kcal for every two rotatable bonds [43]. Both the H-bond-acceptor and the donor is still within range and thus H-bond acceptors, donors, and rotatable bonds are less frequent in oral medicines [44]. Tese three factors promote the oral mode of delivery as being adaptable, practical, and easy one.…”

Section: Discussionmentioning

confidence: 99%

“…Te oxindole derivatives compounds (C-1 and C-2) were given scores of 2.52 and 2.55 by the SwissADME database, indicating simple step processes for synthesis. Te challenging synthetic methods are for compounds with scores of 10 [44].…”

Section: Discussionmentioning

confidence: 99%

In Silico, SwissADME, and DFT Studies of Newly Synthesized Oxindole Derivatives Followed by Antioxidant Studies

Rauf,

Khan,

Khan

et al. 2023

Journal of Chemistry

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The compounds were synthesized by refluxing 6-chlorooxindole with 2,3-dichlorobenzaldehyde and 2,6-dichlorobenzaldehyde in the presence of piperidine as a catalyst and characterized by spectroscopic analysis using 1H NMR, 13C NMR, and mass spectrometry as (E)-3-(2,3-dichlorobenzylidene)-6-chloroindolin-2-one (C-1) and (E)-3-(2,6-dichlorobenzylidene)-6-chloroindolin-2-one (C-2). Additionally, in silico ADME studies indicated that C-1 and C-2 with 1,1 rotatable bonds could have moderate water solubility and therefore could have the potential ability to cross the blood-brain barrier. Both showed high GI absorption, indicating that they are suitable for intestinal absorption while the compounds showed CYP1A2, CYP2C19, and CYP2C9 inhibition. The five drug-likeness criteria, which were Lipinski, Muegge, Ghose, Veber, and Egan, and the principles of drug-likeness are not violated by compounds C-1 and C-2. Also, the DFT computations were performed at the B3LYP level and at 6-311++G ∗ ∗ basis set to evaluate and support the obtained results from the experiment. The FMO results revealed that C-1 could likely prefer the intramolecular interactions rather than the intermolecular interactions, and vice versa for C-2. In addition, the NBO results indicated that the resonance interaction, especially the shift of electron to empty orbitals from lone pair electrons of nitrogen, would contribute to the stabilization of both compounds greatly. In DPPH assay, the compounds showed IC50 values of 37.390 and 34.676 μM, respectively. Similarly, in ABTS assay, the calculated IC50 values for the compounds were 25.381 and 33.706 μM, respectively. In short, these results provided a solid ground for further preclinical studies in quest of new effective therapeutic agents.

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Physicochemical properties, drug likeness, ADMET, DFT studies, and in vitro antioxidant activity of oxindole derivatives

Ahmad

Khan

Serdaroğlu

2023

Computational Biology and Chemistry

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An Overview on the Anticancer Potential of Punarnavine: Prediction of Drug-Like Properties

Cited by 10 publications

References 50 publications

Synthesis, Characterization, and Pharmacokinetic Studies of Thiazolidine-2,4-Dione Derivatives

Synthesis, Characterization, and Pharmacokinetic Studies of Thiazolidine-2,4-Dione Derivatives

In Silico, SwissADME, and DFT Studies of Newly Synthesized Oxindole Derivatives Followed by Antioxidant Studies

Physicochemical properties, drug likeness, ADMET, DFT studies, and in vitro antioxidant activity of oxindole derivatives

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