Experimental and DFT data of p-chlorocalix[4]arene as drugs receptor

Kadir, Maisara Abdul; Razak, Fazira Ilyana Abdul; Haris, Noorazilah

doi:10.1016/j.dib.2020.106263

Cited by 5 publications

(8 citation statements)

References 6 publications

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“…The energies, oscillator strengths, and rotational strengths of the first 60 electronic excitations were calculated using the TDDFT methodology at the M062X/TZVP level with the PCM solvent model of methanol (Table S8). The ECD spectrum was simulated by the overlapping Gaussian function (0.35 eV) in which velocity rotatory strengths of the first seven exited states were adopted . The theoretical ECD curve of 3 R - 1 was obtained by directly reversing that of 3 S - 1 .…”

Section: Resultsmentioning

confidence: 95%

“…After conformational searching in the Spartan 18 program, the results showed three lowest energy conformers within an energy window of 2 kcal/mol. These conformers were then reoptimized using density functional theory (DFT) at the B3LYP/6-31G(d) level using the Gaussian 09 program . The B3LYP/6-31G(d) harmonic vibrational frequencies were further calculated to confirm their stability.…”

Section: Resultsmentioning

confidence: 99%

“…The resulting conformer sets were then geometry optimized using density functional theory (DFT) at the B3LYP/6-31G(d) level in vacuum in the Gaussian 09 program . The frequency analysis was further calculated under the same theoretical level to confirm their stability . For ECD calculation, the first 60 electronic excitations were calculated using the time-dependent DFT (TDDFT) methodology at the M062X/TZVP level with the polarizable continuum model (PCM) using methanol as the solvent.…”

Section: Methods and Materialsmentioning

confidence: 99%

See 2 more Smart Citations

Discovery of a Potential Liver Fibrosis Inhibitor from a Mushroom Endophytic Fungus by Genome Mining of a Silent Biosynthetic Gene Cluster

Cheng

Wang

et al. 2021

J. Agric. Food Chem.

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Liver fibrosis has accounted for liver diseases and overall mortality, but no relevant drug has been developed. Filamentous fungi are important resources of natural products for pharmaceutical development. Calcarisporium arbuscula is a mushroom endophytic fungus, which primarily produces aurovertins. Here, in an aurovertin null-production mutant, one silent gene cluster (mca17) was activated by overexpression of a pathway-specific zinc finger transcriptional regulator, and a tetramic acid-type compound (1, MCA17-1) was identified. Along with detailed structural characterization, its biosynthesis was proposed to be produced from the core PKS-NRPS hybrid enzyme. Moreover, 1 suppressed the activation of LX-2 upon transforming growth factorβ (TGF-β) challenge and had stronger bioactivity than the positive control obeticholic acid (OCA) against liver fibrosis. Our work suggested that this engineered fungus could be a producer of 1 for promising pharmaceutical development, and alternatively, it would be developed as a mushroom ingredient in dietary therapy to prevent liver fibrosis.

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Section: Resultsmentioning

confidence: 95%

Section: Resultsmentioning

confidence: 99%

Section: Methods and Materialsmentioning

confidence: 99%

See 1 more Smart Citation

Discovery of a Potential Liver Fibrosis Inhibitor from a Mushroom Endophytic Fungus by Genome Mining of a Silent Biosynthetic Gene Cluster

Cheng

Wang

et al. 2021

J. Agric. Food Chem.

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“…The 3D structure of BRD4-Cpd4 was download from PDB (PDB code: 6JI4) [ 12 ]. The 3D structure of Cpd9 and Cpd19 were obtained by Gaussian View [ 29 ] and then optimized with Gaussian 09 software [ 29 ] at B3LYP 6-31G* set [ 30 ]. Then, Cpd9 and Cpd19 were docked to BRD4 with AutoDock 4.2.6 software [ 31 ].…”

Section: Methodsmentioning

confidence: 99%

Molecular Dynamic Simulations of Bromodomain and Extra-Terminal Protein 4 Bonded to Potent Inhibitors

Chen

Geng

et al. 2021

Molecules

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Bromodomain and extra-terminal domain (BET) subfamily is the most studied subfamily of bromodomain-containing proteins (BCPs) family which can modulate acetylation signal transduction and produce diverse physiological functions. Thus, the BET family can be treated as an alternative strategy for targeting androgen-receptor (AR)-driven cancers. In order to explore the effect of inhibitors binding to BRD4 (the most studied member of BET family), four 150 ns molecular dynamic simulations were performed (free BRD4, Cpd4-BRD4, Cpd9-BRD4 and Cpd19-BRD4). Docking studies showed that Cpd9 and Cpd19 were located at the active pocket, as well as Cpd4. Molecular dynamics (MD) simulations indicated that only Cpd19 binding to BRD4 can induce residue Trp81-Ala89 partly become α-helix during MD simulations. MM-GBSA calculations suggested that Cpd19 had the best binding effect with BRD4 followed by Cpd4 and Cpd9. Computational alanine scanning results indicated that mutations in Phe83 made the greatest effects in Cpd9-BRD4 and Cpd19-BRD4 complexes, showing that Phe83 may play crucial roles in Cpd9 and Cpd19 binding to BRD4. Our results can provide some useful clues for further BCPs family search.

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“…Supramolecular host molecules, comprising calix[n]arenes (CXs), cyclodextrins (CDs), cucurbiturils (CBs), and pillararenes, have been suggested as smart drug delivery platforms [1,22,23] and have been used as host molecules to encapsulate various chemotherapeutic drugs to improve their bioavailability, prevent their premature degradation in the bloodstream, and increase their targeted intracellular uptake into cancer cells [1][2][3]. Lately, calix[n]arenes (n = 4, 6, and 8) have been employed in drug targeting [24][25][26]. Calixarenes are idyllic host molecules that are synthesized by linking phenolic rings via methylene bridges encompassing three regions; (1) a lower rim with a phenolic hydroxyl group, (2) an upper rim with a para-substituent of a phenolic unit, and (3) a hydrophobic π electron-rich central cavity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and Host-Guest Complexation of Asplatin: Improved In Vitro Cytotoxicity and Biocompatibility as Compared to Cisplatin

et al. 2022

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Para-sulfocalix[n]arenes are promising host molecules that can accommodate various chemotherapeutic drugs. Pt(IV)-based complexes, including satraplatin and asplatin, are promising alternatives that overcome the shortcomings of Pt(II) complexes. In this study, asplatin has been synthesized by fusing acetylsalicylic acid (aspirin) and cisplatin. Furthermore, it has been characterized using 1H NMR, mass spectrometry, elemental analysis, and UHPLC. A host-guest complex of asplatin and p-sulfocalix[4]arene (PSC4) has been developed and characterized using UV, Job’s plot analysis, HPLC, and density functional theory (DFT) calculations. The experimental and computational investigations propose that a 1:1 complex between asplatin and PSC4 is formed. The stability constant of the designed complex has been determined using Job’s plot and UHPLC and computed to be 9.1 × 104 M–1 and 8.7 × 104 M−1, which corresponds to a free energy of complexation of −6.8 kcal mol–1, while the calculated value for the inclusion free energy is −13.2 kcal mol−1. Both experimentally and theoretically estimated complexation free energy show that a stable host-guest complex can be formed in solution. The in vitro drug release study displayed the ability of the complex to release its cargo at a cancerous pH (pH of 5.5). Additionally, the asplatin/PSC4 complex is shown to be biocompatible when tested on human skin fibroblast noncancerous cells, demonstrating the highest in vitro cytotoxic activity against (MCF-7), cervical (HeLa), and lung cancer cells (A-549), with IC50 values of 0.75, 2.15, and 3.60 µg/mL, respectively. This is as compared to either cisplatin (IC50 of 5.47, 5.94 and 9.61 µg/mL, respectively) or asplatin (IC50 of 1.54, 5.05 and 3.91 µg/mL, respectively). On the other hand, the free asplatin exhibited higher cytotoxicity on cancerous cells and lower toxicity on noncancerous cells. The outcomes of the present joint theoretical and experimental investigation reinforce the interest in platinum-based anticancer therapeutics when they are protected from undesired interactions and suggest the use of the PSC4 macromolecule as a promising carrier for Pt(IV) anticancer drugs. The formed asplatin/PSC4 inclusion complex may represent an effective chemotherapeutic agent.

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Experimental and DFT data of p-chlorocalix[4]arene as drugs receptor

Cited by 5 publications

References 6 publications

Discovery of a Potential Liver Fibrosis Inhibitor from a Mushroom Endophytic Fungus by Genome Mining of a Silent Biosynthetic Gene Cluster

Discovery of a Potential Liver Fibrosis Inhibitor from a Mushroom Endophytic Fungus by Genome Mining of a Silent Biosynthetic Gene Cluster

Molecular Dynamic Simulations of Bromodomain and Extra-Terminal Protein 4 Bonded to Potent Inhibitors

Synthesis, Characterization and Host-Guest Complexation of Asplatin: Improved In Vitro Cytotoxicity and Biocompatibility as Compared to Cisplatin

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