Diaminobenzene schiff base, a novel class of DNA minor groove binder

Helal, Muath; Al-Mudaris, Zena A.; Al–Douh, Mohammed Hadi; Osman, Hasnah; Wahab, Habibah A.; Al-Najjar, Belal O.; Abdallah, Hassan H.; Majid, Amin Malik Shah Abdul

doi:10.3892/ijo.2012.1491

Cited by 13 publications

(5 citation statements)

References 31 publications

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“…The molecular docking technique helps in understanding non-covalent drug-DNA interactions of small molecules into the targeted region of DNA for rational drug design and discovery. The minor groove of DNA is preferred over major one due to lesser steric hindrance, electrostatic factors and its narrow shape [35, 36, 37, 38, 39, 40].…”

Section: Resultsmentioning

confidence: 99%

Synthesis, DFT studies, molecular docking, antimicrobial screening and UV fluorescence studies on ct-DNA for novel Schiff bases of 2-(1-aminobenzyl) benzimidazole

Singhal

Khanna

2019

Heliyon

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Novel Schiff bases (SBs) were synthesized by condensation of 2-(1-Amino benzyl) benzimidazole with heterocyclic and aromatic carbonyl compounds. The structural characterization was done using 1H, 13C NMR, FTIR and ES-MS spectroscopic techniques. The in silico pharmacokinetics showed that nearly all compounds obeyed Lipinski rule of 5 with low toxicity and metabolic stability. The global reactivity descriptors were calculated using DFT approach. The molecular docking result of SBs with ct-DNA suggested interaction via groove binding mode. The antibacterial activity was tested against S. aureus and E. coli, indicated significant inhibition than reference drug. The compound 4d gave best results at 50 μg ml−1 concentrations. UV/Vis and Fluorescence spectroscopy tools were used to evaluate ct-DNA binding ability of compounds 4a–e through hypochromic shift. The steady state fluorescence predicted a moderate binding constant of 1.12 × 104 for 4d, indicative of non-intercalative mode.

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Section: Resultsmentioning

confidence: 99%

Synthesis, DFT studies, molecular docking, antimicrobial screening and UV fluorescence studies on ct-DNA for novel Schiff bases of 2-(1-aminobenzyl) benzimidazole

Singhal

Khanna

2019

Heliyon

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“…Both unsymmetrical and symmetrical bis-Schiff bases can be coordinated as ligands with the central transition metal ion to form complexes. The complexes of unsymmetrical bis-Schiff base ligands are used as irregular binding model with peptides [7], while the intercalation of some symmetrical bis-Schiff bases with DNA and UV-Vis spectroscopy has been studied [8,9]. However, some symmetrical bis-Schiff base structures are studied and characterized by 1D and 2D NMR spectroscopy and X-Ray Crystallography analysis [10][11][12].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Antimicrobial Activity Studies of New Schiff Base Tetradentate Ligands and Their Manganese (II) Complexes

Selim

Al–Douh

Al–Nohey

et al. 2020

AJOCS

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Two Schiff base tetradentate ligands 4 and 5 were synthesized by condensation reactions of 4-hydroxy-3-methoxy-5-((2-nitrophenyl)diazenyl) benzaldehyde 1 with 1,2-diaminoethane 2 and 1,2-diaminobenzene 3, respectively. Treatment of synthesized ligands with the manganese (II) chloride MnCl2 6 gave two complexes 7 and 8 of general formula ML. The synthesized ligands and their complexes were characterized by FTIR, UV-Vis, Mass spectroscopy, and elemental analysis. The biological activity of the synthesized compounds were tested. It was found that ligand 5 and the complexes 7 and 8 possess antibacterial activity against the gram –ve Proteus mirabilis.

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“…Following conjugation of PD0721 scFv with DOX, the UV-Vis spectrum analysis revealed a significant red shift in the maximum absorption, primarily attributed to the presence of two aldehyde groups in oxidized Dex T-10. The latter could undergo condensation with the amino groups in DOX and PD0721 scFv, thus forming a covalent cross-linking structure, known as the Schiff base (31). As a result, the molecular weight and the degree of conjugation were increased.…”

Section: Discussionmentioning

confidence: 99%

Preparation and evaluation of the PD0721‑DOX antibody‑drug conjugate targeting EGFRvIII to inhibit glioblastoma

Hu,

Liu,

Zhang

et al. 2024

Exp Ther Med

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Epidermal growth factor receptor variant III (EGFRvIII) is prominently expressed in various epithelial tumors. PD0721, a single-chain antibody (scFv), has been developed to specifically target EGFRvIII. Although doxorubicin (DOX) is an essential treatment approach for glioblastoma (GBM), its toxic effects and limited targeting capabilities are a challenge. To overcome the above limitations, antibody-drug conjugates (ADCs) have been developed to exploit the specificity of monoclonal antibodies in directing potent cytotoxic drugs to tumor cells expressing the target antigens. The present study aimed to conjugate DOX with PD0721 scFv to construct a PD0721-DOX ADC targeting EGFRvIII and examine its targeting effect and in vitro anti-GBM activity. PD0721-DOX ADC was generated by combining PD0721 scFv with DOX, using dextran T-10 as a linker. The drug-to-antibody ratio (DAR) was measured by ultraviolet and visible spectrophotometry (UV-Vis). A series of techniques, including cytotoxicity assays, immunofluorescence, cell internalization and flow cytometry assays were employed to evaluate the targeting efficacy and anti-GBM activity of the PD0721-DOX ADC. Following the conjugation of PD0721 scFv with DOX, the UV-Vis results showed a noticeable red shift in the maximum absorbance. The DAR of PD0721 scFv and DOX was 9.23:1. Cytotoxicity assays demonstrated that DK-MG cells treatment with PD0721-DOX ADC at 10 and 20 µg/ml significantly increased cytotoxicity compared with U-87MG ATCC cells (all P<0.01). Confocal microscopy revealed distinct green and red fluorescence in EGFRvIII-expressing DK-MG cells, while no fluorescence was observed in EGFRvIII negative U-87MG ATCC cells. Furthermore, compared with U-87MG ATCC cells, DK-MG cells showed effective internalization of the PD0721-DOX ADC (P<0.001). Finally, flow cytometric analyses indicated that the PD0721-DOX ADC significantly promoted the apoptosis of DK-MG cells compared with U-87MG ATCC cells (P<0.01). In summary, the current study suggested that the PD0721-DOX ADC could exhibit a notable targeting efficacy and potent anti-GBM activity.

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Diaminobenzene schiff base, a novel class of DNA minor groove binder

Cited by 13 publications

References 31 publications

Synthesis, DFT studies, molecular docking, antimicrobial screening and UV fluorescence studies on ct-DNA for novel Schiff bases of 2-(1-aminobenzyl) benzimidazole

Synthesis, DFT studies, molecular docking, antimicrobial screening and UV fluorescence studies on ct-DNA for novel Schiff bases of 2-(1-aminobenzyl) benzimidazole

Synthesis, Characterization, and Antimicrobial Activity Studies of New Schiff Base Tetradentate Ligands and Their Manganese (II) Complexes

Preparation and evaluation of the PD0721‑DOX antibody‑drug conjugate targeting EGFRvIII to inhibit glioblastoma

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