Synthesis of new morpholine containing 3-amido-9-ethylcarbazole derivative and studies on its biophysical interactions with calf thymus DNA/HSA

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Fulya Kıpçaka, Tugba Taskın Tokbc, Halil Duyarde, Zeynel Seferoğlue & Elmas Gökoğlua*a Department of Chemistry, Hacettepe University, Ankara, Turkeyb Department of Chemistry, Gaziantep University, Gaziantep, Turkeyc Department of Bioinformatics and Computational Biology, Gaziantep University, Gaziantep, Turkeyd Department of Chemistry, Gebze Technical University, Kocaeli, Turkeye Department of Chemistry, Gazi University, Ankara, TurkeySupplemental data for this article can be accessed online at https://doi.org/10.1080/07391102.2020.1734093.CONTACT Elmas Gökoğlu gokoglu@hacettepe.edu.tr Department of Chemistry, Hacettepe University, 06800 Ankara, TurkeyAbstractIn this work, we presented the synthesis and investigation of binding properties of the new morpholine containing 3-amido-9-ethylcarbazole derivative (CMR) to calf thymus DNA (ctDNA) and human serum albumin (HSA) by fluorescence spectroscopy, UV absorption spectroscopy and molecular docking method. A decrease in Stern–Volmer constants was obtained with increase in temperature; it shows that static quenching mechanism leads to formation of new CMR-DNA/HSA complexes, which have hydrophobic interaction as the predominant role in the binding modes. Also, binding properties of DNA were investigated with competition assays on two probes (EB and H33258) by absorption, ionic strength and iodide ion quenching methods. The results suggested that CMR entered into the minor groove binding on the A-T region of DNA. The spectral data further confirmed by molecular docking which elicited that CMR complexes have similar interaction and conformation trends to each target, DNA and HSA. The experimental and computational results show that CMR has been classified as a promising molecule in drug designing of other carbazole derivatives.Communicated by Ramaswamy H. Sarma