DNA interaction studies of sesamol (3,4-methylenedioxyphenol) food additive

Kashanian, Soheila; Ghobadi, Ameneh Tahmasian; Roshanfekr, Hamideh; Shariati, Zohreh

doi:10.1007/s11033-012-2159-x

Cited by 8 publications

(8 citation statements)

References 30 publications

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“…The values of (η/η 0 ) 1/3 were plotted against [DNA]/[Cu complex], where η and η 0 are the relative viscosities of DNA in the presence and absence of the complex, respectively (figure 3). The plot of figure 3 reveals that the drug shows little change in DNA viscosity, which is consistent with DNA groove binding [53]. both B and C conformation.…”

Section: Viscosity Measurementssupporting

confidence: 65%

Synthesis, characterization, molecular modeling, and DNA interaction studies of a Cu(II) complex containing drug of chronic hepatitis B: adefovir dipivoxil

Shahabadi

Falsafi

Fili

2015

Journal of Coordination Chemistry

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A new copper(II) complex [Cu(adefovir) 2 Cl 2 ], where adefovir = adefovir dipivoxil drug, was synthesized and characterized by using different physicochemical methods. Binding interaction of this complex with calf thymus DNA (ct-DNA) has been investigated by multi-spectroscopic techniques and molecular modeling study. The complex displays significant binding properties of ct-DNA. The results of fluorescence and UV-vis absorption spectroscopy indicated that, this complex interacted with ct-DNA in a groove-binding mode, and the binding constant was 4.3(±0.2) × 10 4 M −1 . The fluorimeteric studies showed that the reaction between the complex and ct-DNA is exothermic (ΔH = 73.91 kJ M −1 ; ΔS = 357.83 J M −1 K −1 ). Furthermore, the complex induces detectable changes in the CD spectrum of ct-DNA and slightly increases its viscosity which verified the groove-binding mode. The molecular modeling results illustrated that the complex strongly binds to the groove of DNA by relative binding energy of the docked structure −5.74 kcal M −1 . All experimental and molecular modeling results showed that the Cu(II) complex binds to DNA by a groove-binding mode.

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Section: Viscosity Measurementssupporting

confidence: 65%

Synthesis, characterization, molecular modeling, and DNA interaction studies of a Cu(II) complex containing drug of chronic hepatitis B: adefovir dipivoxil

Shahabadi

Falsafi

Fili

2015

Journal of Coordination Chemistry

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“…CD spectroscopy is a very sensitive technique that has been used extensively for analysis of changes that occur in the secondary structure of polypeptides, proteins and DNA under the influence of interacting ligands . Non‐covalent drug–DNA interactions affect the structure of DNA, and hence alter the CD spectral behaviour.…”

Section: Resultsmentioning

confidence: 99%

Naproxen intercalates with DNA and causes photocleavage through ROS generation

Husain

Yaseen

Rehman

et al. 2013

FEBS J

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Naproxen is an important non-steroidal anti-inflammatory drug with many pharmacological and biological properties. In this study, we have attempted to ascertain the mode of action and the mechanism of binding of naproxen to DNA. We have also demonstrated that, upon irradiation with white light, naproxen generates reactive oxygen species, causing DNA cleavage. Generation of reactive oxygen species from photo-irradiated naproxen as determined spectrophotometrically was found to lead to nicking of plasmid DNA as analyzed by agarose gel electrophoresis. Without photo-irradiation, naproxen binds to DNA and forms drug-DNA complexes as revealed by spectroscopic techniques. Several experiments such as determination of the effect of urea, iodide-induced quenching and a competitive binding assay with ethidium bromide showed that naproxen binds to DNA primarily in an intercalative manner. These observations were further supported by CD analysis, viscosity measurements and molecular docking. Using DNA as a template, fluorescence resonance energy transfer between naproxen and ethidium bromide was also observed, further strengthening the evidence for intercalative binding of naproxen with DNA.

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“…By virtue of its small size and low molecular weight (138.12 g/ mole), it could be inserted in the DNA grooves, leading to helix unwinding and cell apoptosis. 2 To the best of our knowledge, its cytotoxic effect has been tested on hepatic, 3 breast, 4 lung, 5 skin, 6 and colon cancers 7 but not on any type of brain cancers. Unfortunately, the physicochemical characters of sesamol as a small molecule with adequate aqueous solubility (38.8 mg/mL) and an almost balanced partition coefficient value (1.29) allow its even biodistribution throughout the body and absence of specific affinity toward a pathological site/ tissue.…”

Section: Introductionmentioning

confidence: 99%

“…Recently, sesamol was exploited as a potential cytotoxic material on different cancer cell lines. By virtue of its small size and low molecular weight (138.12 g/mole), it could be inserted in the DNA grooves, leading to helix unwinding and cell apoptosis . To the best of our knowledge, its cytotoxic effect has been tested on hepatic, breast, lung, skin, and colon cancers but not on any type of brain cancers.…”

Section: Introductionmentioning

confidence: 99%

Synchronizing In Silico, In Vitro, and In Vivo Studies for the Successful Nose to Brain Delivery of an Anticancer Molecule

et al. 2021

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Sesamol is a sesame seed constituent with reported activity against many types of cancer. In this work, two types of nanocarriers, solid lipid nanoparticles (SLNs) and polymeric nanoparticles (PNs), were exploited to improve sesamol efficiency against the glioma cancer cell line. The ability of the proposed systems for efficient brain targeting intranasally was also inspected. By the aid of two docking programs, the virtual loading pattern inside these nanocarriers was matched to the real experimental results. Interactions involved in sesamol–carrier binding were also assessed, followed by a discussion of how different scoring functions account for these interactions. The study is an extension of the computer-assisted drug formulation design series, which represents a promising initiative for an upcoming industrial innovation. The results proved the power of combined in silico tools in predicting members with the highest sesamol payload suitable for delivering a sufficient dose to the brain. Among nine carriers, glyceryl monostearate (GMS) and polycaprolactone (PCL) scored the highest sesamol payload practically and computationally. The EE % was 66.09 ± 0.92 and 61.73 ± 0.47 corresponding to a ΔG (binding energy) of −8.85 ± 0.16 and −5.04 ± 0.11, respectively. Dynamic light scattering evidenced the formation of 215.1 ± 7.2 nm and 414.25 ± 1.6 nm nanoparticles, respectively. Both formulations demonstrated an efficient cytotoxic effect and brain-targeting ability compared to the sesamol solution. This was evidenced by low IC50 (38.50 ± 10.37 μM and 27.81 ± 2.76 μM) and high drug targeting efficiency (7.64 ± 1.89-fold and 13.72 ± 4.1-fold) and direct transport percentages (86.12 ± 3.89 and 92.198 ± 2.09) for GMS-SLNs and PCL-PNs, respectively. The results also showed how different formulations, having different compositions and characteristics, could affect the cytotoxic and targeting ability.

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DNA interaction studies of sesamol (3,4-methylenedioxyphenol) food additive

Cited by 8 publications

References 30 publications

Synthesis, characterization, molecular modeling, and DNA interaction studies of a Cu(II) complex containing drug of chronic hepatitis B: adefovir dipivoxil

Synthesis, characterization, molecular modeling, and DNA interaction studies of a Cu(II) complex containing drug of chronic hepatitis B: adefovir dipivoxil

Naproxen intercalates with DNA and causes photocleavage through ROS generation

Synchronizing In Silico, In Vitro, and In Vivo Studies for the Successful Nose to Brain Delivery of an Anticancer Molecule

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