The Effect of Electron Donor and Withdrawing Groups Attached to 1,2,3-Selendiazole Based Compounds on Anti-Cancer Properties

Abstract

The optimized structure of 1,2,3-selendiazole based compounds 9c, 9c-1 and 9c-2 was obtained at the B3LYP/6-31G+(d) level. The highest occupied molecular orbital energy (EHOMO), the lowest unoccupied molecular orbital energy (ELUMO), the energy gap (ΔE), hardness (η), softness (σ), electronegativity (χ), chemical potential (μ), global molecular Quantum parameters such as electrophilicity (ω) index, global molecular nucleophilicity (ɛ) index, the electron accepting (ω+) and electron donating (ω-) powers were compared. Different from 9c, the effects of ethyl and chloro substituents on 1,2,3-selendiazole were examined. It has been found that ethyl and chlorine substituents change their inhibition activities according to their electron donating properties. Molecular electrostatic potential maps and frontier molecular orbital contour diagrams of the investigated compounds were obtained. Electrophilic and nucleophilic regions were determined. 9c was docked against a breast cancer (MCF7) cell line to investigate the antitumor activities of compounds 9c-1 and 9c-2. Molecular insertion results were found to be higher than 9c-2 versus MCF-7 cell line.

Keywords

• 1,2,3-selendiazole derivatives
• Quantum chemical parameters
• Molecular docking

References

1. [1] W. Fischer, J. Chem. Educ. 78 (2001) 1333.
2. [2] C. Thiry, A. Ruttens, L. De Temmerman, Y.J. Schneider, L. Pussemier, Current knowledge in species-related bioavailability of seleium in food, Food Chem. 130 (4) (2012) 767–784.
3. [3] S. Misra, M. Boylan, A. Selvam, J.E. Spallholz, M. Björnstedt, Redox-active selenium compounds—from toxicity and cell death to cancer treatment, Nutrients 7 (5) (2015) 3536–3556.
4. [4] T. Chen, W. Zheng, Y.S. Wong, F. Yang, Mitochondria-mediated apoptosis in human breast carcinoma MCF-7 cells induced by a novel selenadiazole derivative, Biomed. Pharmacother. 62 (2008) 77–84.
5. [5] T. Chen, Y.S. Wong, W. Zheng, J. Liu, Caspase- and p53-dependent apoptosis in breast carcinoma cells induced by a synthetic selenadiazole derivative, Chem. Biol. Interact. 180 (2009) 54–60.
6. [6] C. Sanmartin, D. Plano, J.A. Palop, Selenium compounds and apoptotic modulation: a new perspective in cancer therapy, Mini Rev. Med. Chem. 8 (2008) 1020–1031.
7. [7] W. Dorr, Effects of selenium on radiation responses of tumor cells and tissue, Strahlenther. Onkol. 182 (2006) 693–695.
8. [8] Atta, S. M. S., Farrag, D. S., Sweed, A. M., & Abdel-Rahman, A. H. (2010). Preparation of new polycyclic compounds derived from benzofurans and furochromones. An approach to novel 1, 2, 3-thia-, and selena-diazolofurochromones of anticipated antitumor activities. European journal of medicinal chemistry, 45(11), 4920-4927.

9. [9] Dennington II, R. D., Keith, T. A., & Millam, J. M. (2009). GaussView 5.0, Wallingford, CT.
10. [10] Gaussian09, R. (2009). 02, MJ Frisch, GW Trucks, HB Schlegel, GE Scuseria, MA Robb, JR Cheeseman, G. Scalmani in no. 3 Gaussian. Inc., Wallingford, 4
11. [11] EL AATIAOUI, A., Koudad, M., Chelfi, T., ERKAN, S., Azzouzi, M., Aouniti, A., ... & Oussaid, A. Experimental and theoretical study of new Schiff bases based on imidazo (1, 2-a) pyridine as corrosion inhibitor of mild steel in 1M HCl. Journal of Molecular Structure, 1226, 129372.
12. [12] Al-Otaibi, J. S., Mary, Y. S., Mary, Y. S., Kaya, S., & Erkan, S. (2020). Spectral analysis and DFT investigation of some benzopyran analogues and their self-assemblies with graphene. Journal of Molecular Liquids, 317, 113924.
13. [13] Erkan, S., & Karakaş, D. (2019). DFT investigation and molecular docking studies on dinuclear metal carbonyls containing pyridyl ligands with alkyne unit. Chemical Papers, 73(10), 2387-2398.
14. [14] Kaya, S., Erkan, S., & Karakaş, D. (2020). Computational investigation of molecular structures, spectroscopic properties and antitumor-antibacterial activities of some Schiff bases. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 244, 118829.
15. [15] Ceylan, M., Erkan, S., Yaglioglu, A. S., Akdogan Uremis, N., & Koç, E. (2020). Antiproliferative Evaluation of Some 2‐[2‐(2‐Phenylethenyl)‐cyclopent‐3‐en‐1‐yl]‐1, 3‐benzothiazoles: DFT and Molecular Docking Study. Chemistry & Biodiversity, 17(4), e1900675.
16. [16] Erkan, S., & Karakaş, D. (2020). A theoretical study on cyclometalated iridium (III) complexes by using a density functional theory.
17. [17] Erkan, S. (2019). Activity of the rocuronium molecule and its derivatives: A theoretical calculation. Journal of Molecular Structure, 1189, 257-264.
18. [18] ERKAN, S. (2018). Structural, Spectroscopic and Anti-cancer Properties of Hydroxy-and Sulfonamide-Azobenzene Platinum (II) Complexes: DFT and Molecular Docking Studies. Cumhuriyet Science Journal, 39(4), 1036-1051.
19. [19] Kaya, S., Erkan, S., & Karakaş, D. (2021). Computational investigation of molecular structures, spectroscopic properties and antitumor-antibacterial activities of some Schiff bases. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 244, 118829.