Hantzsch‐Like Synthesis, DNA Photocleavage, DNA/BSA Binding, and Molecular Docking Studies of Bis(sulfanediyl)bis(tetrahydro‐5‐deazaflavin) Analogs Linked to Naphthalene Core

The cyclocondensation reaction of aldehydes with dimedone and bis(6‐aminopyrimidin‐4‐one) in acetic acid led to the formation of the corresponding bis(pyrimido[4,5‐b]quinoline‐4,6‐diones) which are known as bis(sulfanediyl)bis(tetrahydro‐5‐deazaflavin) analogs in a single step. Also, bis(pyrimido[4,...

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Bibliographic Details
Published in:Chemistry & biodiversity 2022-09, Vol.19 (9), p.e202100958-n/a
Main Authors: Ragheb, Mohamed A., Abdelwahab, Reham E., Darweesh, Ahmed F., Soliman, Marwa H., Elwahy, Ahmed H. M., Abdelhamid, Ismail A.
Format: Article
Language:English
Subjects:
Acetic acid
Aldehydes
Analogs
Binding
Biomolecules
Bis(6-aminopyrimidin-4-one)
bis(sulfanediyl)bis(tetrahydro-5-deazaflavin)
Bovine serum albumin
Deoxyribonucleic acid
Diketones
DNA
DNA biosynthesis
DNA photocleavage
DNA/BSA binding
Electrophoresis
Gel electrophoresis
Molecular docking
Naphthalene
Plasmids
Quinoline
Serum albumin
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Summary:The cyclocondensation reaction of aldehydes with dimedone and bis(6‐aminopyrimidin‐4‐one) in acetic acid led to the formation of the corresponding bis(pyrimido[4,5‐b]quinoline‐4,6‐diones) which are known as bis(sulfanediyl)bis(tetrahydro‐5‐deazaflavin) analogs in a single step. Also, bis(pyrimido[4,5‐b]quinoline‐4,6‐diones) which are linked to naphthyl core via phenoxymethyl linkage is prepared. The interactions of the synthesized compounds with DNA and bovine serum albumin (BSA) were studied. Gel electrophoresis assay was used to show the capability of the compounds to photocleave the supercoiled pBR322 plasmid DNA in UV‐A (365 nm). Besides, the most photocleavable compound, bis(tetrahydropyrimido[4,5‐b]quinoline‐4,6‐dione) linked to pyridin‐3‐yl at position‐5 exhibits good binding affinities toward CT‐DNA and BSA as supported by UV/VIS spectral studies. In addition to the experimental findings, a molecular docking simulation was performed to collect detailed binding data for this compound to both biomolecules.
ISSN:1612-1872
1612-1880
DOI:10.1002/cbdv.202100958