Biological activity evaluation and computational study of novel triazene derivatives containing benzothiazole rings

Alamri, Mona A.; Al-Jahdali, Mutlaq; Al‐Radadi, Najlaa S.; Hussien, Mostafa A.

doi:10.1016/j.molstruc.2020.129507

Cited by 10 publications

(14 citation statements)

References 48 publications

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“…[12] 2.5 | Molecular docking Docking studies were performed using the Molecular Operating Environment (MOE) program according to a previously reported protocol. [10,13] The crystal structure of target proteins, breast and colon cancer receptors, was retrieved from the Protein Data Bank (http://www.rcsb. org/pdb/) (PDB code = 1hk7 and 3IG7, respectively).…”

Section: Cytotoxic Activitymentioning

confidence: 99%

“…The two receptors were selected based on literatures suggesting its importance as targets for potential breast and colon cancer therapy. [10,50] Molecular docking studies of the ligand and its metal complexes against both receptors, 3ig7 and 1hk7 were performed to evaluate the binding affinity of these compounds. Generally, a stronger binding affinity between the receptor and the tested compounds reveals lower binding free energy.…”

Section: Molecular Dockingmentioning

confidence: 99%

“…A triazene ligand, ( E )‐2‐(3‐(4‐nitrophenyl)triaz‐1‐en‐1‐yl)benzo[ d ]thiazole (L), with a benzothiazole moiety has been previously designed and investigated in our laboratory. [ 10 ] In this study, we report the synthesis, characterization, and properties of Cu(II), Co(II), Ni(II), Mn(II), and Zn(II) complexes of the triazene L. These complexes were experimentally analyzed by infrared (IR), ultraviolet/visible (UV/Vis), and electron paramagnetic resonance (EPR) spectroscopies, powder X‐ray diffraction (XRD), magnetic moment measurements, and thermogravimetric analysis (TGA). A theoretical investigation was conducted using density functional theory (DFT) calculations.…”

Section: Introductionmentioning

confidence: 99%

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Characterization, theoretical investigation, and biological applications of Mn(II), Co(II), Ni(II), Cu(II), and Zn(II) complexes of a triazene ligand containing a benzothiazole ring

Alamri

Al-Jahdali

Al‐Radadi

et al. 2021

Applied Organom Chemis

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Herein, Mn(II), Co(II), Ni(II), Cu(II), and Zn(II) complexes of a previously synthesized triazene ligand, namely, (E)-2-(3-(4-nitrophenyl)triaz-1-en-1-yl)benzo [d]thiazole (L), were prepared. The metal:ligand ratio of complexes was determined by molar ratio method, and complexes were synthesized based on the result ratio (1:2 for Co(II), Ni(II), and Zn(II) complexes, and (1:1) for Cu(II) and Mn(II)). The complexes were characterized by infrared (IR) and electron paramagnetic resonance (EPR) spectroscopies, magnetic moment, and/or molar conductance measurements. IR spectra suggested the existence of bidentate binding through the nitrogen atom of the thiazole ring and nitrogen atom of the triazene linkage. Molar conductivities indicated the nonelectrolytic nature of all the complexes. Magnetic moment and EPR of the complexes confirmed their octahedral geometries. Thermal studies were conducted to confirm the structures and analyze the thermal stabilities of the complexes. Activation thermodynamic parameters were determined using the Coats-Redfern and Horowitz-Metzger methods. The calf thymus DNA binding activity was investigated by absorption titration experiments and viscosity measurements, and intrinsic binding constants of complexes range from 4.00 Â 10 5 to 5.00 Â 10 5 M À1 . Cytotoxic activities were examined against MCF-7 and HCT-116 cell lines. Although all the complexes exhibited reasonable cytotoxic effects, their cytotoxic activities were in the following order: Zn(II) > Cu(II) > Mn(II) > Co(II) > Ni(II). Zn(II) complex showed the highest activity with IC 50 values are 2.87 and 1.94 μg ml À1 against MCF-7 and HCT-116, respectively. Molecular docking was used to assess the binding affinities of these complexes to colon cancer (3ig7) and breast cancer (1hk7) proteins.Zn(II) complex showed the best docking scores compared with the ligand and other tested complexes. Results of molecular docking well correlated with those of the cytotoxicity experiments.

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Section: Cytotoxic Activitymentioning

confidence: 99%

Section: Molecular Dockingmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Characterization, theoretical investigation, and biological applications of Mn(II), Co(II), Ni(II), Cu(II), and Zn(II) complexes of a triazene ligand containing a benzothiazole ring

Alamri

Al-Jahdali

Al‐Radadi

et al. 2021

Applied Organom Chemis

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“…The HOMO-LUMO gap is related to the global chemical reactivity parameters. Large HOMO-LUMO gap is responsible for high kinetic stability [ 85 ]. In the current study, curcumin showed the highest values of ∆ E, ionization potential, absolute electronegativity, absolute and global hardness, global electrophilicity, and additional electronic charge.…”

Section: Discussionmentioning

confidence: 99%

Interactions of selected cardiovascular active natural compounds with CXCR4 and CXCR7 receptors: a molecular docking, molecular dynamics, and pharmacokinetic/toxicity prediction study

Murad

Alqurashi

Hussien

2022

BMC Complement Med Ther

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Background The chemokine CXCL12 and its two receptors (CXCR4 and CXCR7) are involved in inflammation and hematopoietic cell trafficking. This study was designed to investigate molecular docking interactions of four popular cardiovascular-active natural compounds; curcumin, resveratrol, quercetin, and eucalyptol; with these receptors and to predict their drug-like properties. We hypothesize that these compounds can modify CXCL12/CXCR4/CXCR7 pathway offering benefits for coronary artery disease patients. Methods Docking analyses were carried and characterized by Molecular Environment (MOE) software. Protein Data Bank (http://www.rcsb.org/) has been retrieved from protein structure generation and crystal structures of CXCR4 and CXCR7 receptors (PDB code = 3ODU and 6K3F). The active sites of these receptors were evaluated and extracted from full protein and molecular docking protocol was done for compounds against them. The presented parameters included docking scores, ligand binding efficiency, and hydrogen bonding. The pharmacokinetic/toxic properties (ADME/T) were calculated using SwissADME, ProTox-II, and Pred-hERG softwares to predict drug-like properties of the compounds. The thermochemical and molecular orbital analysis, and molecular dynamics simulations were also done. Results All compounds showed efficient interactions with the CXCR4 and CXCR7 receptors. The docking scores toward proteins 3ODU of CXCR4 and 6K3F of CXCR7 were − 7.71 and − 7.17 for curcumin, − 5.97 and − 6.03 for quercetin, − 5.68 and − 5.49 for trans-resveratrol, and − 4.88 and − 4.70 for (1 s,4 s)-eucalyptol respectively indicating that all compounds, except quercetin, have more interactions with CXCR4 than with CXCR7. The structurally and functionally important residues in the interactive sites of docked CXCR4-complex and CXCR7-complex were identified. The ADME analysis showed that the compounds have drug-like properties. Only (1 s,4 s)-Eucalyptol has potential weak cardiotoxicity. The results of thermochemical and molecular orbital analysis and molecular dynamics simulation validated outcomes of molecular docking study. Conclusions Curcumin showed the top binding interaction against active sites of CXCR4 and CXCR7 receptors, with the best safety profile, followed by quercetin, resveratrol, and eucalyptol. All compounds demonstrated drug-like properties. Eucalyptol has promising potential because it can be used by inhalation or skin massage. To our knowledge, this is the first attempt to find binding interactions of these natural agents with CXCR4 and CXCR7 receptors and to predict their druggability.

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“…Thus, molecular docking analysis was conducted to elucidate how the free ligands and the oxidovanadium(IV) complex interact with the investigated protein. The dock procedures were evaluated against colon cancer (3IG7), which was chosen based on previous research suggesting its inhabitation as colon cancer therapy [53,54]. The binding energy scores for free ligands and their synthesized oxidovanadium(IV) compounds are presented in Table 9.…”

Section: Molecular Dockingmentioning

confidence: 99%

QSAR Modeling, Molecular Docking and Cytotoxic Evaluation for Novel Oxidovanadium(IV) Complexes as Colon Anticancer Agents

et al. 2022

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Four new drug-based oxidovanadium (IV) complexes were synthesized and characterized by various spectral techniques, including molar conductance, magnetic measurements, and thermogravimetric analysis. Moreover, optimal structures geometry for all syntheses was obtained by the Gaussian09 program via the DFT/B3LYP method and showed that all of the metal complexes adopted a square-pyramidal structure. The essential parameters, electrophilicity (ω) value and expression for the maximum charge that an electrophile molecule may accept (ΔNmax) showed the practical biological potency of [VO(CTZ)2] 2H2O. The complexes were also evaluated for their propensity to bind to DNA through UV–vis absorption titration. The result revealed a high binding ability of the [VO(CTZ)2] 2H2O complex with Kb = 1.40 × 10⁶ M−1. Furthermore, molecular docking was carried out to study the behavior of the VO (II) complexes towards colon cancer cell (3IG7) protein. A quantitative structure–activity relationship (QSAR) study was also implemented for the newly synthesized compounds. The results of validation indicate that the generated QSAR model possessed a high predictive power (R2 = 0.97). Within the investigated series, the [VO(CTZ)2] 2H2O complex showed the greatest potential the most selective compound comparing to the stander chemotherapy drug.

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Biological activity evaluation and computational study of novel triazene derivatives containing benzothiazole rings

Cited by 10 publications

References 48 publications

Characterization, theoretical investigation, and biological applications of Mn(II), Co(II), Ni(II), Cu(II), and Zn(II) complexes of a triazene ligand containing a benzothiazole ring

Characterization, theoretical investigation, and biological applications of Mn(II), Co(II), Ni(II), Cu(II), and Zn(II) complexes of a triazene ligand containing a benzothiazole ring

Interactions of selected cardiovascular active natural compounds with CXCR4 and CXCR7 receptors: a molecular docking, molecular dynamics, and pharmacokinetic/toxicity prediction study

QSAR Modeling, Molecular Docking and Cytotoxic Evaluation for Novel Oxidovanadium(IV) Complexes as Colon Anticancer Agents

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