Voltametric and molecular docking investigations of ferrocenylmethylaniline and its N-acetylated derivative interacting with DNA: Original scientific paper

Asma Yahiaoui; Nabil Benyza; Amel Messai; Touhami Lanez; Elhafnaoui  Lanez

doi:10.5599/jese.2061

Authors

Asma Yahiaoui University of El Oued, Chemistry Department, VTRS Laboratory, B.P.789, 39000, El Oued https://orcid.org/0009-0004-1641-7254
Nabil Benyza University of Khenchela, laboratory of sensors, instrumentations and process, 40000, Khenchela https://orcid.org/0009-0005-0853-4458
Amel Messai University of Khenchela, laboratory of sensors, instrumentations and process, 40000, Khenchela https://orcid.org/0000-0002-5862-1905
Touhami Lanez University of El Oued, Chemistry Department, VTRS Laboratory, B.P.789, 39000, El Oued https://orcid.org/0000-0002-3978-7635
Elhafnaoui Lanez University of El Oued, Chemistry Department, VTRS Laboratory, B.P.789, 39000, El Oued, https://orcid.org/0000-0002-6543-2547

DOI:

https://doi.org/10.5599/jese.2061

Keywords:

Ferrocene derivatives, DNA minor groove binding, binding site size, binding free energy, docking simulations

Abstract

N-ferrocenylmethylaniline (FA) and its N-acetylated derivative (NFA) have been synthesized and fully characterized by various physicochemical techniques such as ¹H and ¹³C NMR spectroscopy. Interactions of FA and NFA with chicken blood DNA were studied by cyclic voltammetry (CV) and molecular docking (MD). The obtained results suggest that both FA and NFA bind strongly via electrostatic interactions to the minor groove of double helix DNA. These electrostatic interactions were evidenced by the ﬁndings like a negative formal potential shift in CV and ionic strength effect. The results further show that the binding constants and free binding energies obtained by MD analysis are roughly matched to those obtained from CV. Furthermore, the binding site size was evaluated from voltammetric data.

Downloads

Download data is not yet available.

References

J. F. Alhmoud, J. F. Woolley, A.-E. Al Moustafa, M.I. Malki, DNA Damage/Repair Management in Cancers, Cancers (Basel) 12 (2020) 1050. https://doi.org/10.3390/cancers12041050

N. Chowdhury, A. Bagchi, An Overview of DNA-Protein Interactions, Current Chemical Biology 9 (2016) 73-83. https://doi.org/10.2174/2212796809666151022202255

M. R. Shorkaei, Z. Asadi, M. Asadi, Synthesis, characterization, molecular docking and DNA binding studies of Al(III), Ga(III) and In(III) water-soluble complexes, Journal of Molecular Structure 1109 (2016) 22-30. https://doi.org/https://doi.org/10.1016/j.molstruc.2015.12.070

S. Ghosh, Cisplatin, The first metal based anticancer drug, Bioorganic Chemistry 88 (2019) 102925. https://doi.org/10.1016/j.bioorg.2019.102925

V. J. Fiorina, R. J. Dubois, S. Brynes. Ferrocenyl polyamines as agents for the chemoimmunotherapy of cancer, Journal of Medicinal Chemistry 21 (1978) 393-395. https://doi.org/10.1021/jm00202a016

N. Zegheb, C. Boubekri, T. Lanez, E. Lanez, In Silico Study on N-Ferrocenylmethyl-N-Phenylpropionohydrazide and N-Ferrocenylmethyl-N-Pheylbenzohydrazide as Anticancer Drugs for Breast and Prostate Cancer, International Journal of Pharmacology, Phytochemistry and Ethnomedicine 11 (2018) 17-25. https://doi.org/10.18052/WWW.SCIPRESS.COM/IJPPE.11.17

A. Khennoufa, L. Bechki, T. Lanez, E. Lanez, N. Zegheb, Spectrophotometric, voltametric and molecular docking studies of binding interaction of N-ferrocenylmethylnitroanilines with bovine serum albumin, Journal of Molecular Structure 1224 (2021) 129052. https://doi.org/10.1016/j.molstruc.2020.129052

A. Kedadra, T. Lanez, E. Lanez, H. Hemmami, M. Henni, Synthesis and antioxidant activity of six novel N-ferrocenylmethyl-N-(nitrophenyl)- and -N-(cyanophenyl)-acetamides: Cyclic voltammetry and molecular docking studies, Journal of Electrochemical Science and Engineering 12 (2022) 293-304. https://doi.org/10.5599/jese.1162

T. Lanez, E. Lanez, A Molecular Docking Study of N-Ferrocenylmethylnitroanilines as Potential Anticancer Drugs, International Journal of Pharmacology, Phytochemistry and Ethnomedicine 2 (2016) 5-12. https://doi.org/10.18052/www.scipress.com/IJPPE.2.5

N. Zegheb, C. Boubekri, T. Lanez, E. Lanez, T. T. Küçükkılınç, E. Öz, A. Khennoufa, S. Khamouli, S. Belaidi, In Vitro and In Silico Determination of Some N-ferrocenylmethylaniline Derivatives as Anti-Proliferative Agents Against MCF-7 Human Breast Cancer Cell Lines, Anti-Cancer Agents in Medicinal Chemistry 22 (2022) 1426-1437. https://doi.org/10.2174/1871520621666210624141712

O. Kennard, DNA-drug interactions, Pure and Applied Chemistry 65 (1993) 1213-1222. https://doi.org/10.1351/pac199365061213

N. Shahabadi, A. Fatahi, Multispectroscopic DNA-binding studies of a tris-chelate nickel(II) complex containing 4,7-diphenyl 1,10-phenanthroline ligands, Journal of Molecular Structure 970 (2010) 90-95. https://doi.org/10.1016/j.molstruc.2010.02.048

J. M. Osgerby, P. L. Pauson, 128. Ferrocene derivatives. Part VI. DL-ferrocenylalanine, Journal of the Chemical Society (Resumed) (1958) 656-660. https://doi.org/10.1039/JR9580000656

T. Lanez, H. Benaicha, E. Lanez, M. Saidi, Electrochemical, spectroscopic and molecular docking studies of 4-methyl-5-((phenylimino)methyl)-3H- and 5-(4-fluorophenyl)-3H-1,2-dithiole-3-thione interacting with DNA, Journal of Sulfur Chemistry 39 (2018) 76-88. https://doi.org/10.1080/17415993.2017.1391811

E. Lanez, L. Bechki, T. Lanez, Computational molecular docking, voltammetric and spectroscopic DNA interaction studies of 9N-(Ferrocenylmethyl)adenine, Chemistry and Chemical Technology 13 (2019) 11-17. https://doi.org/10.23939/chcht13.01.011

R. Vijayalakshmi, M. Kanthimathi, V. Subramanian, B.U. Nair, DNA cleavage by a chromium(III) complex, Biochemical and Biophysical Research Communications 271 (2000) 731-734. https://doi.org/10.1006/bbrc.2000.2707

J. A. Glasel, Validity of nucleic acid purities monitored by 260nm/280nm absorbance ratios, Biotechniques 18 (1995) 62-63.

Anthony J. Pearson, Metallo-organic chemistry, Chichester [West Sussex] ; New York, John Wiley & Sons, 1985. ISBN: 978-0471904403

C.-S. Lu, X.-M. Ren, C.-J. Hu, H.-Z. Zhu, Q.-J. Meng, The Inclusion Compound of a New Ionizable Derivative of b b-Cyclodextrin with Ferrocenium Drug, Chemical and Pharmaceutical Bulletin 49 (2001) 818-821. https://doi.org/10.1248/cpb.49.818

M. Frisch, G. Trucks, H. Schlegel, G. S. Wallingford, U. CT, U. 2009, Gaussian 09; Gaussian, Inc, Gaussian, (2016). https://gaussian.com/g09citation

C. Chizallet, S. Lazare, D. Bazer-Bachi, F. Bonnier, V. Lecocq, E. Soyer, A.-A. Quoineaud, N. Bats, Catalysis of Transesterification by a Nonfunctionalized Metal−Organic Framework: Acido-Basicity at the External Surface of ZIF-8 Probed by FTIR and ab Initio Calculations, Journal of the American Chemical Society 132 (2010) 12365-12377. https://doi.org/10.1021/ja103365s

M. Shahsavari, S. Tajik, I. Sheikhshoaie, H. Beitollahi, Fabrication of Nanostructure Electrochemical Sensor Based on the Carbon Paste Electrode (CPE) Modified with Ionic Liquid and Fe3O4/ZIF-67 for Electrocatalytic Sulfamethoxazole Detection, Topics in Catalysis 65 (2022) 577-586. https://doi.org/10.1007/s11244-021-01471-8

O. Trott, A. J. Olson, AutoDock Vina: Improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading, Journal of Computational Chemistry 30 (2009) 455-461. https://doi.org/10.1002/jcc.21334

N. Li, Y. Ma, C. Yang, L. Guo, X. Yang, Interaction of anticancer drug mitoxantrone with DNA analyzed by electrochemical and spectroscopic methods, Biophysical Chemistry 116 (2005) 199-205. https://doi.org/10.1016/j.bpc.2005.04.009

G.-C. Zhao, J.-J. Zhu, J.-J. Zhang, H.-Y. Chen, Voltametric studies of the interaction of methylene blue with DNA by means of β-cyclodextrin, Analytica Chimica Acta 394 (1999) 337-344. https://doi.org/10.1016/S0003-2670(99)00292-5

M. Aslanoğlu, N. Öge, Voltametric, UV Absorption and Viscometric Studies of the Interaction of Norepinephrine with DNA, Turkish Journal of Chemistry 29 (2005) 477-485. https://journals.tubitak.gov.tr/chem/vol29/iss5/3

M. Aslanoglu, G. Ayne, Voltammetric studies of the interaction of quinacrine with DNA, Analytical and Bioanalytical Chemistry 380 (2004) 658-663. https://doi.org/10.1007/s00216-004-2797-5

M. Coll, J. Aymami, G. A. van der Marel, J. H. van Boom, A. Rich, A. H. J. Wang, Molecular structure of the netropsin-d(CGCGATATCGCG) complex: DNA conformation in an alternating AT segment, Biochemistry 28 (1989) 310-320. https://doi.org/10.1021/bi00427a042

G. M. Morris, H. Ruth, W. Lindstrom, M. F. Sanner, R. K. Belew, D. S. Goodsell, A. J. Olson, Software news and updates AutoDock4 and AutoDockTools4: Automated docking with selective receptor flexibility, Journal of Computational Chemistry 30 (2009) 2785-2791. https://doi.org/10.1002/jcc.21256

BIOVIA, Dassault Systems, Discovery Studio Visualizer, v21.1.1.020289, San Diego: Dassault Systems, 2020. https://www.3ds.com/products/biovia/all-products

Voltametric and molecular docking investigations of ferrocenylmethylaniline and its N-acetylated derivative interacting with DNA

Original scientific paper

Authors

DOI:

Keywords:

Abstract

Downloads

References

Downloads

Published

How to Cite

Issue

Section

License

Funding data

Most read articles by the same author(s)

clarivate

elsevier

links

Information