Synthesis of 5-(4-(1H-phenanthro[9,10-d]imidazol-2-yl)benzylidene)thiazolidine-2,4-dione as promising DNA and serum albumin-binding agents and evaluation of antitumor activity

Singh, Iqubal; Rani, Richa; Luxami, Vijay; Paul, Kamaldeep

doi:10.1016/j.ejmech.2019.01.053

Cited by 33 publications

(22 citation statements)

References 46 publications

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“…Temperature did not vary in a broad range; therefore, the value of the enthalpy change can be regarded as constant, and the van't Hoff equation can be used in order to estimate the thermodynamic parameters:

\ln K = - normalΔ H / italicRT + normalΔ S / R,

where K is the binding constant at the corresponding temperature (K), Δ H is the enthalpy change, R is the universal gas constant, and Δ S is the entropy change. [ 20 ] The values of Δ H and Δ S were obtained from the slope and the y intercept of a ln K versus 1/ T plot. Moreover, the free energy change (Δ G ) can be calculated from the following relationship [ 20 ] :

normalΔ G = normalΔ H - T normalΔ S .

…”

Section: Methodsmentioning

confidence: 99%

“…[ 20 ] The values of Δ H and Δ S were obtained from the slope and the y intercept of a ln K versus 1/ T plot. Moreover, the free energy change (Δ G ) can be calculated from the following relationship [ 20 ] :

normalΔ G = normalΔ H - T normalΔ S .

…”

Section: Methodsmentioning

confidence: 99%

“…where K is the binding constant at the corresponding temperature (K), ΔH is the enthalpy change, R is the universal gas constant, and ΔS is the entropy change. [20] The values of ΔH and ΔS were obtained from the slope and the y intercept of a lnK versus 1/T plot. Moreover, the free energy change (ΔG) can be calculated from the following relationship [20] :…”

Section: Fluorescence Spectra Acquisition and Mathematical Formulaementioning

confidence: 99%

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New heteroleptic lanthanide complexes as multimodal drugs: Cytotoxicity studies, apoptosis, cell cycle analysis, DNA interactions, and protein binding

Arbănași

Musat

Mihăilă³

et al. 2020

Applied Organom Chemis

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We report herein the synthesis and characterization of four new heteroleptic complexes of Sm(III), Eu(III), Gd(III), and Tb(III) with the natural flavonoid 5-hydroxyflavone (primuletin) and 1,10-phenanthroline. According to the physicochemical characterization, the mononuclear complexes correspond to the general formula [Ln(OH) 2 L 1 L 2 ]ÁnH 2 O, where L 1 = C 15 H 9 O 3 (deprotonated 5-hydroxyflavone) and L 2 = C 12 H 8 N 2 (1,10-phenanthroline), Ln is the lanthanide cation, and n = 4 for Sm(III), 3.5 for Eu(III), 2 for Gd(III), and 3 for Tb(III). A six-coordinated distorted octahedron geometry was proposed for the complexes, and density functional theory (DFT) studies were used to calculate their optimized geometry. Cytotoxicity was studied using MTS assay on cervical, colorectal, colon, breast, and ovarian adenocarcinoma cell lines. Flow cytometry data were consistent with apoptotic cell death and disruption of the cell cycle in cervical and colon cancer cells. As a means to investigate the mechanism underlying the cytotoxic effects, the abilities of the complexes to interact with calf thymus DNA, human serum albumin, and transferrin have also been assessed. According to experimental and computational studies, the four lanthanide complexes act as DNA intercalators and bind strongly to serum proteins.

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\ln K = - normalΔ H / italicRT + normalΔ S / R,

normalΔ G = normalΔ H - T normalΔ S .

…”

Section: Methodsmentioning

confidence: 99%

normalΔ G = normalΔ H - T normalΔ S .

…”

Section: Methodsmentioning

confidence: 99%

Section: Fluorescence Spectra Acquisition and Mathematical Formulaementioning

confidence: 99%

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New heteroleptic lanthanide complexes as multimodal drugs: Cytotoxicity studies, apoptosis, cell cycle analysis, DNA interactions, and protein binding

Arbănași

Musat

Mihăilă³

et al. 2020

Applied Organom Chemis

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“…A series of compounds reported by Singh et al explored the benzimidazole scaffold for the synthesis of DNA-interactive anticancer candidates [ 104 , 105 , 106 , 107 ]. In one such effort, naphthalimide–benzimidazole hybrid compounds were prepared as potential antiproliferative agents against the NCI panel of 60 human cancer cell lines [ 104 ].…”

Section: Imidazoles As Inhibitors Of Other Targetsmentioning

confidence: 99%

“…Compound 107 displayed greater potency against A549 cells (IC 50 = 1.85 µM) compared to compound 104 (IC 50 = 5.02 µM). As above, spectroscopic experiments were used to provide evidence for the binding of these compounds to DNA via intercalation.A series of compounds reported by Singh et al explored the benzimidazole scaffold for the synthesis of DNA-interactive anticancer candidates[104][105][106][107]. In one such effort, naphthalimide-benzimidazole hybrid compounds were prepared as potential antiprolif-…”

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confidence: 99%

Imidazoles as Potential Anticancer Agents: An Update on Recent Studies

et al. 2021

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Nitrogen-containing heterocyclic rings are common structural components of marketed drugs. Among these heterocycles, imidazole/fused imidazole rings are present in a wide range of bioactive compounds. The unique properties of such structures, including high polarity and the ability to participate in hydrogen bonding and coordination chemistry, allow them to interact with a wide range of biomolecules, and imidazole-/fused imidazole-containing compounds are reported to have a broad spectrum of biological activities. This review summarizes recent reports of imidazole/fused imidazole derivatives as anticancer agents appearing in the peer-reviewed literature from 2018 through 2020. Such molecules have been shown to modulate various targets, including microtubules, tyrosine and serine-threonine kinases, histone deacetylases, p53-Murine Double Minute 2 (MDM2) protein, poly (ADP-ribose) polymerase (PARP), G-quadraplexes, and other targets. Imidazole-containing compounds that display anticancer activity by unknown/undefined mechanisms are also described, as well as key features of structure-activity relationships. This review is intended to provide an overview of recent advances in imidazole-based anticancer drug discovery and development, as well as inspire the design and synthesis of new anticancer molecules.

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Phenanthrene Appending Ruthenium Complexes: DNA Binding, Molecular Docking, TDDFT Calculation, and Photocytoxicity In Vitro

Liu,

Ma,

et al. 2024

Applied Organom Chemis

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Photodynamic therapy (PDT) has been an effective tumor treatment to reduce the side effects of chemotherapy. Herein, we described the synthesis of two Ru (II) complexes by introducing a phenanthrene unit and their photocytotoxicity. Ru1 and Ru2 displayed high DNA affinities by intercalation. Under light, two complexes produced high singlet oxygen (1O2) quantum yields and cleaved DNA efficiently. Both high DNA affinities and 1O2 quantum yields of two complexes resulted in obvious photocytotoxicity towards Hela, A549, and A375 cells. Furthermore, low dark cytotoxicity was also observed for two complexes, which may promote them to act as potential PDT agents. TDDFT (Time‐dependent density functional theory) calculations also demonstrated two complexes that might display the PDT activities via 1O2 photogeneration.

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Synthesis of 5-(4-(1H-phenanthro[9,10-d]imidazol-2-yl)benzylidene)thiazolidine-2,4-dione as promising DNA and serum albumin-binding agents and evaluation of antitumor activity

Cited by 33 publications

References 46 publications

New heteroleptic lanthanide complexes as multimodal drugs: Cytotoxicity studies, apoptosis, cell cycle analysis, DNA interactions, and protein binding

New heteroleptic lanthanide complexes as multimodal drugs: Cytotoxicity studies, apoptosis, cell cycle analysis, DNA interactions, and protein binding

Imidazoles as Potential Anticancer Agents: An Update on Recent Studies

Phenanthrene Appending Ruthenium Complexes: DNA Binding, Molecular Docking, TDDFT Calculation, and Photocytoxicity In Vitro

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