Research Article

Synthesis, Structural Characterization and Investigation of DNA/BSA Binding Properties of a Homo-disulphide Schiff Base Compound Carrying Oxo Propargyl Group

Volume: 43 Number: 4 December 27, 2022
EN

Synthesis, Structural Characterization and Investigation of DNA/BSA Binding Properties of a Homo-disulphide Schiff Base Compound Carrying Oxo Propargyl Group

Abstract

In this work, a new homo-disulphide Schiff base compound (HDSB) was prepared and its structure was characterised by common spectroscopic and analytical methods. The compound was obatined from the condensation reaction of 2-aminothiophenol and 2-hydroxy-4-(prop-2-yn-1-yloxy)benzaldehyde in benzene. In the reaction, both Schiff base condensation and oxidation of thiols into disulphide formed. The isolated compound was structurally characterized by single crystal X-ray diffraction experiment. The homo-disulphide Schiff base compound (HDSB) was screened for its DNA/BSA binding properties using UV-Vis absorption and emission spectral studies. The compound showed considerable binding affinity to double-stranded fish sperm DNA (FSds-DNA) with binding constant of 4.1 × 104 M-1. Spectral measurements suggest that HDSB interacts with DNA in a minor groove binding mode. The compound also showed binding properties towards BSA (bovine serum albumin). The incremental addition of HDSB to the BSA solution resulted in a significant decrease in the characteristic emission band of BSA in the range of 320-500 nm (λexc: 280 nm) showing the binding interactions between HDSB and BSA.

Keywords

Homo-disulphide Schiff base, Structural characterization, DNA/BSA binding, Spectroscopy

References

  1. [1] Abdel-Mohsen H. T., Sudheendran K., Conrad J., Beifuss U., Synthesis of disulfides by laccase-catalyzed oxidative coupling of heterocyclic thiols, Green Chem., 15 (2013) 1490–1495.
  2. [2] Ali A. Q., Teoh S. G., Salhin A., Eltayeb N. E., Khadeer Ahamed, M. B., Majid A. M. S. A., Synthesis of isatin thiosemicarbazones derivatives: In vitro anti-cancer, DNA binding and cleavage activities, Spectrochim. Acta - Part A Mol. Biomol. Spectrosc., 125 (2014) 440–448.
  3. [3] Amirnasr M., Bagheri M., Farrokhpour H., Schenk K. J., Mereiter K., Ford P. C., New Zn(II) complexes with N2S2 Schiff base ligands. Experimental and theoretical studies of the role of Zn(II) in disulfide thiolate-exchange, Polyhedron, 71 (2014) 1–7.
  4. [4] Annaraj B., Balakrishnan C., Neelakantan M. A., Synthesis, structure information, DNA/BSA binding affinity and in vitro cytotoxic studies of mixed ligand copper(II) complexes containing a phenylalanine derivative and diimine co-ligands, J. Photochem. Photobiol. B Biol., 160 (2016) 278–291.
  5. [5] Annaraj B., Neelakantan M. A., Synthesis, crystal structure, spectral characterization and biological exploration of water soluble Cu(II) complexes of vitamin B6 derivative, Eur. J. Med. Chem., 102 (2015) 1–8.
  6. [6] Behpour M., Ghoreishi S. M., Mohammadi N., Soltani N., Salavati-Niasari M., Investigation of some Schiff base compounds containing disulfide bond as HCl corrosion inhibitors for mild steel, Corros. Sci., 52 (2010) 4046–4057.
  7. [7] Bharti S., Choudhary M., Mohan B., Rawat S. P., Sharma S. R., Ahmad K., Syntheses, spectroscopic characterization, SOD-like properties and antibacterial activities of dimer copper (II) and nickel (II) complexes based on imine ligands containing 2-aminothiophenol moiety: X-ray crystal structure determination of disulfide Schif, J. Mol. Struct., 1164 (2018) 137–154.
  8. [8] Bhowon M. G., Jhaumeer Laulloo S., Hosten E. C., Khodabaccus M. M., Rhyman L., Ramasami P., Synthesis, spectroscopic, biological and DFT studies of new t-butyl substituted salicylaldimines having disulfide moiety, J. Mol. Struct., 1175 (2019) 13–23.
  9. [9] Chen Y., Ren J. Q., Zhang X. G., Wu D. Y., Shen A. G., Hu J. M., Alkyne-Modulated Surface-Enhanced Raman Scattering-Palette for Optical Interference-Free and Multiplex Cellular Imaging, Anal. Chem., 88 (2016) 6115–6119.
  10. [10] Demircioğlu Z., Synthesis, crystal structure, spectroscopic characterization, chemical activity and molecular docking studies of (E) – 2 - ( ( ( 3 - chloro – 4 -methylphenyl ) imino ) methyl ) – 6 - ethoxyphenol , J. Mol. Struct., 1246 (2021) 131114.
APA
Köse, A. (2022). Synthesis, Structural Characterization and Investigation of DNA/BSA Binding Properties of a Homo-disulphide Schiff Base Compound Carrying Oxo Propargyl Group. Cumhuriyet Science Journal, 43(4), 613-620. https://doi.org/10.17776/csj.1114040
AMA
1.Köse A. Synthesis, Structural Characterization and Investigation of DNA/BSA Binding Properties of a Homo-disulphide Schiff Base Compound Carrying Oxo Propargyl Group. CSJ. 2022;43(4):613-620. doi:10.17776/csj.1114040
Chicago
Köse, Ayşegül. 2022. “Synthesis, Structural Characterization and Investigation of DNA BSA Binding Properties of a Homo-Disulphide Schiff Base Compound Carrying Oxo Propargyl Group”. Cumhuriyet Science Journal 43 (4): 613-20. https://doi.org/10.17776/csj.1114040.
EndNote
Köse A (December 1, 2022) Synthesis, Structural Characterization and Investigation of DNA/BSA Binding Properties of a Homo-disulphide Schiff Base Compound Carrying Oxo Propargyl Group. Cumhuriyet Science Journal 43 4 613–620.
IEEE
[1]A. Köse, “Synthesis, Structural Characterization and Investigation of DNA/BSA Binding Properties of a Homo-disulphide Schiff Base Compound Carrying Oxo Propargyl Group”, CSJ, vol. 43, no. 4, pp. 613–620, Dec. 2022, doi: 10.17776/csj.1114040.
ISNAD
Köse, Ayşegül. “Synthesis, Structural Characterization and Investigation of DNA BSA Binding Properties of a Homo-Disulphide Schiff Base Compound Carrying Oxo Propargyl Group”. Cumhuriyet Science Journal 43/4 (December 1, 2022): 613-620. https://doi.org/10.17776/csj.1114040.
JAMA
1.Köse A. Synthesis, Structural Characterization and Investigation of DNA/BSA Binding Properties of a Homo-disulphide Schiff Base Compound Carrying Oxo Propargyl Group. CSJ. 2022;43:613–620.
MLA
Köse, Ayşegül. “Synthesis, Structural Characterization and Investigation of DNA BSA Binding Properties of a Homo-Disulphide Schiff Base Compound Carrying Oxo Propargyl Group”. Cumhuriyet Science Journal, vol. 43, no. 4, Dec. 2022, pp. 613-20, doi:10.17776/csj.1114040.
Vancouver
1.Ayşegül Köse. Synthesis, Structural Characterization and Investigation of DNA/BSA Binding Properties of a Homo-disulphide Schiff Base Compound Carrying Oxo Propargyl Group. CSJ. 2022 Dec. 1;43(4):613-20. doi:10.17776/csj.1114040