Crystal structure and DNA binding properties of khellin oxime

Beyazit, Neslihan; Kaya, Kerem; Şenel, Pelin; Özdemir, Ayşe; Gölcü, Ayşegül

doi:10.1016/j.molstruc.2019.07.019

Cited by 6 publications

(3 citation statements)

References 45 publications

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“…[ 7 ] The interaction and binding properties of khellin with DNA have been studied. [ 8,9 ] Khellin prevents cell damage caused by oxalate in renal epithelial cells. [ 7 ] DFT‐theoretical calculations were used for inspection of the optimized geometries of some furo[3,2‐g]chromenes.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and antimicrobial evaluation of the novel heteroannulated furo[3′,2′:6,7]chromeno[2,3‐b]pyridines: Part 1

Ibrahim

Al‐Harbi

Allehyani

2020

Journal of Heterocyclic Chem

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The chemical behavior of 4,9-dimethoxy-5-oxo-5H-furo[3,2-g]chromene-6-carbonitrile (1) was investigated toward some acyclic and cyclic active methylene ketones namely acetylacetone, ethyl acetoacetate, ethyl benzoylacetate, acetoacetanilide, dimedone, indanedione, pyrazolidine-3,5-dione and 5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one, barbituric acid and 1-allylthiobarbituric acid, and hippuric acid. A variety of novel heteroannulated furochromenopyridines were efficiently synthesized through a cascade reactions between 4,9-dimethoxy-5-oxo-5H-furo[3,2-g]chromene-6-carbonitrile (1) and the carbon nucleophilic reagents. Structures of the new products were inferred based on their analytical and spectral data.

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Section: Introductionmentioning

confidence: 99%

Synthesis and antimicrobial evaluation of the novel heteroannulated furo[3′,2′:6,7]chromeno[2,3‐b]pyridines: Part 1

Ibrahim

Al‐Harbi

Allehyani

2020

Journal of Heterocyclic Chem

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“…Due to the small sample requirement, it has been widely used in biological and chemical analyses. Electrochemical methods of DNA interaction of small molecules such as drugs are possible in two ways: (i) the signal change of the electroactive bases (guanine or adenine, or both) is measured and interpreted according to these changes; (ii) necessary calculations are made by measuring the intensity of the peak currents in the oxidation and/or reduction direction of small molecules (before and after the interaction with DNA) [23][24]39]. In this study, extract 1 or 2 was separately added to the dsDNA solution of a certain concentration, and the changes in the peak current and peak potential of dsDNA were interpreted.…”

Section: Voltammetric Studiesmentioning

confidence: 99%

Pharmacological Properties of <i>Genista sagittalis</i> L. (Fabaceae) Grown in Turkey

et al. 2023

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The genus Genista L. (Family: Fabaceae) is a plant having several traditional uses for treating common ailments such as diabetes, ulcer, and respiratory diseases. In this current study, the composition of essential oil and the biological activities of Genista sagittalis L. (Fabaceae) from Kocaeli: Yuvacık Dam Basin have been studied. A total of fourteen components were identified in the essential oil. The identified compounds belonged to straight-chain alkane, aromatic ether, and terpenoid derivatives. The antibacterial activity analyses demonstrated that G. sagittalis flower extract only had low activity against P. mirabilis and P. aeruginosa with MICs 1 to 2 mg/mL, as the peduncle extract showed strong anti-QS activity at 1.3 mg/mL. To the best of our knowledge, the current work is the first to report the antimicrobial and anti-quorum sensing activity of G. sagittalis growing in Turkey. Double-stranded DNA binding affinity investigations of the flower and peduncle ethanol extracts indicate that there are interactions with double-stranded DNA and related binding constants (Kb) were found as 1.97×103±0.37 and 3.68×102±0.44 for the flower and peduncle extract, respectively.

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“…The therapeutic effects of KHE are directly linked to its photobiological activity, which in turn is related to its photobinding to DNA ability. When KHE is excited by UV radiation, it predominantly photobinds with thymidine in DNA, forming furan monoadducts, in contrast with psoralen compounds, which form diadducts and lead to interstrand crosslinks in the DNA duplex [7,8]. The process involves the intercalation of KHE between the base pairs of the nucleic acid followed by the photocyclo-addition with pyrimidine bases, particularly thymine [8][9][10].…”

Section: Introductionmentioning

confidence: 99%

Development of Gel-in-Oil Emulsions for Khellin Topical Delivery

et al. 2020

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Hypopigmentation is a progressive dermatological condition caused by a reduction in the skin pigment, melanin. Its treatment is considered a challenge due to the lack of a highly efficient single therapy. Currently, the main treatments include photochemotherapy, application of corticosteroids and immunosuppressants, and laser. Khellin-based gel-in-oil emulsions appear as a promising alternative since they ensure a concentration of the drug, a natural furanochromone, at the desired location, skin surface. Khellin promotes repigmentation as it forms a dark colored complex after solar irradiation. The aim of this study was the development and characterization (e.g., rheological behaviour, droplet size, tackiness, adhesion and spreadability) of three topical gel-in-oil emulsions prepared with different emollients, formulated through a cold emulsification process, and suitable for the incorporation of khellin. In vitro studies were performed to evaluate the drug release and permeation profiles across artificial membranes and excised human skin, respectively, using Franz-type vertical diffusion cells. The W/O emulsions developed showed macroscopic appearance, shear-thinning behavior with a mean droplet size from 3.28 to 4.28 μm, suitable for topical application. In vitro studies revealed permeation values of about 1% of khellin across the stratum corneum, making these gel-in-oil emulsions promising for preclinical and clinical studies. The cold process, being an easy and low energy production method, represents an innovative strategy to produce khellin-based gel-in-oil emulsions to treat patients with hypopigmentation.

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Crystal structure and DNA binding properties of khellin oxime

Cited by 6 publications

References 45 publications

Synthesis and antimicrobial evaluation of the novel heteroannulated furo[3′,2′:6,7]chromeno[2,3‐b]pyridines: Part 1

Synthesis and antimicrobial evaluation of the novel heteroannulated furo[3′,2′:6,7]chromeno[2,3‐b]pyridines: Part 1

Pharmacological Properties of <i>Genista sagittalis</i> L. (Fabaceae) Grown in Turkey

Development of Gel-in-Oil Emulsions for Khellin Topical Delivery

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