IN VITRO AND IN SILICO EVALUATION OF ANTICANCER ACTIVITY OF N,N-DIMETHYLAMINOMETHYLFERROCENE
DOI:
https://doi.org/10.4314/jfas.v11i2.14Keywords:
DNA, Dimethylaminomethylferrocene, Molecular docking, Interaction parameters, Cancer.Abstract
The aim of this stydy was to examine the interaction of DNA with the ligand N,N-dimethylaminomethylferrocene (NDF) in buffer phosphate solution (pH = 7.2) by electronic spectroscopy, electrochemical and molecular docking technics. The electrochemical results showed that the binding constant and free binding energy of the addauct DNA-NDF is equal to 1.48×10-4 and -23,81 KJ.mol-1 respectively. These results were in good agreement with those obtained from electronic spectroscopie assays; furthermore the interaction was also confirmed by the low value of diffusion coefficient of the bounded ligand 1.83×10-8 cm2.s-1 as compared to the free ligand 2.13×10-8 cm2.s-1. In addition the in silico study by molecular docking confirms the obtained in vitro results. Molecular docking further indicated that the ligand is binds to DNA via a hydrogen bond between ist nitrogen atom and the oxygen number 4 of the deoxyadenine of the DNA B-chain.
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References
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[2] Lacave, R., Larsen, Ch-J., Robert, J. (2005). Cancérologie fondamentale, John LibbeyEurotext, Paris, 437p.
[3]Lacroix, R., Sabatier, F., Digna, T.,George, F., Sampol, J. (2009). La leucémie myéloïde chronique, 14 p
[4] Schwab, M. (2011). Encyclopedia of Cancer .Ed: 3. Springer Science & Business Media, New York. 3934p
[5] Ricco, A.J. (1997). Chemical and BiologicalSensors and Analytical Electrochemica lMethods: Proceedings of the Symposium on Chemical and BiologicalSensors and AnalyticalElectrochemicalMethods, The Electrochemical Society, 1100p
[6] Görmen, M. (2010). Synthèse de composès organomètalliques de la série du ferrocénophane et évaluation de leurs activités antiprolifératives sur les cellules du cancer du sein et de la prostate, Cancer. Chimie ParisTech, 2010. Français, 244p
[7] Klajner, M. J. (2011). Organomethalic compounds as a anti-cancer agents: interaction with DNA and migration in cell. Thèse de doctorat. Université de STRASBOURG. P05-06.
[8] Gulam, F. M., Manohar, V. L. (2014). Synthesis of ferrocene based organometallic compounds and antimicrobial activity. Journal of applied chemistry. 7: 27-32
[9] Shafqat, A. (2013). DNA interaction, Antibacterial and Antifungal studies of 3-nitrophenylferrocene. J. Chem. Soc. Pak. 35:3
[10] Didier Astruc.(2016). Why is Ferrocene so Exceptional? Eur. J. Inorg. Chem. 2017, 6–29 DOI: 10.1002/ejic.201600983
[11] Olivier. M.-G. (2009). ELECTROCHIMIE ET APPLICATIONS. EDITION 2009. p11
[12] Raufa, S., Gooding, J.J., Akhtar, K., Ghauri, M.A., Rahman, M., Anwar, M.A.
Khalid, A.M. (2005). Electrochemical approach of anticancer drugs–DNA interaction, Journal of Pharmaceutical and Biomedical Analysis 37, 205–217
[13] Shah, A. (2010). Redox Behavior and DNA Binding Studies of Some Electro active Compounds Quaid-i-AzamUniversity, Islamabad.
[14] Sirajuddin, M., Saqib, Ali., Amin, Badshah. (2013). Drug-DNA interactions and their study by UV-Visible, fluorescence, spectroscopies and cyclic voltamètrie, Elseviers, jornal of photochemistry and photobiology B: Biology science direct, 124(1-19)
[15] Altaf, A.A., Lal, B., Khan,NBadshah, A., Ullah, Sh., Akbar, K .(2016).Spectroscopic, Electrochemical, and In Silico Characterization of ComplexFormedbetween 2- Ferrocenylbenzoic Acid and DNA, Journal of Chemistry, Vol 2016 (2016), Article ID
7468951, 8 p.doi.org/10.1155/2016/7468951
[16] Henni, M. (2017). Synthèse, caractérisation et évaluation in vitro de l'activité biologique et du pouvoir mutagène de quelques N-(ferrocenylmethyl) amino-benzonitrile. Thése de doctorat. Uniiversiité Echahiid Hamma Lakhdar EL-OUED. 185p
[17] H. Nasiri, M. Forouzandeh,n M.J. Rasaee, and F. Rahbarizadeh.(2005) ; Modified Salting-Out Method: High-Yield, High-Quality Genomic
DNA Extraction From Whole Blood Using Laundry Detergent; Journal of Clinical Laboratory Analysis 19:229–232 (2005)
[18] Glasel J. Validity of nucleic acid purities monitored by 260 nm/280 nm absorbance ratios. Biotechniques. 1995;8:62-63
[19] Vijayalakshmi R, Kanthimathi M, Subramanian V, Nair BU. cleavage by a chromium (III) complex. Biochem. Biophys. Res. Commun. 2000; 271:731-734.
[20] Lu X, Zhu K, Zhang M, Liu H, Kang J. Voltammetric studies of the interaction of transition-metal complexes with DNA: J. Biochem. Biophys. Met, 2002;52(3):189-200.
[21] Ozsoz M, Erdem A, Kara P, Kerman K, Ozkan D. Electrochemical biosensor for the detection of interaction between arsenic trioxide and DNA based on guanine signal. Electroanalysis. 2003;15(7):613-619.
[22] Feng, Q., Li, N. Q., Jiang, Y.Y. (1997). Electrochemicalstudies of porphyrininteractingwith DNA and determination of DNA. Anal. Chim. Acta. , 344, 97.
[23] Atkins PW. Physical Chemistry. Oxford University Press, Oxford, UK. 1986; 263-265
[24] Ye H, Cande C, Stephanou NC, Jiang S, Gurbuxani S. Larochette N, Daugas E, Garrido C, Kroemer G, Wu H. DNA Binding Is Required for the Apoptogenic Action of Apoptosis Inducing Factor. Nat. Struct. Mol. Biol. 2002;9:680-684.
[25] Daghriri H, Huq F, Beale P. Studies on activities, cell up take and DNA binding of four multinuclear complexes of the form: [{trans-PtCl(NH3)2}2μ-{trans-Pd(NH3)2-(H2N(CH2)nNH2)2}]Cl4 where n = 4–7. J. Inorg. Biochem. 2004;98(11):1722-1733.
[26] Afzal Shah, abdur rauf, Asad Ullah, Azeema Munir, Rumana Querishi, Iftikhar Ahmad, Muhammad Tahir Soomro, Zia-Ur-Rehman.( 2013). Electrochemical investigations of unexplored anthraquinones and their DNA binding.J.Electrochem.Sci.Eng.3(1), 19-27; doi:10,5599/jese.2012.0026
[27] M.S. Ibrahim. (2001),Voltammetric studies of the interaction of nogalamycin antitumor drug with DNA. Analytica Chimica Acta 443 (2001) 63–72
[28] Brett, C.M.A., Brett. A.M.O. (1993). Electrochemistry : Principles, Methods and Applications, Oxford Science University Publications, Oxford
[29] Aslanoglu, M., Oge, N. (2005).Voltammetric, UV Absorption and ViscometricStudies of the Interaction of Norepinephrinewith DNA, Turk. J. Chem. 29, 477-485.
[30] Aslanoglu M, Ayne G. Voltammetric studies of the Interaction of quinacrine with DNA. Anal. Bioanal. Chem. 2004;380(4):658-663.
[33] Friedli, C. (2002). Chimie générale pour ingénieur, PPUR presses polytechniques, 747p.
[34] Can, Ozluer., Hayriye, Eda., Satana, Kara. (2014). Approche Electrochemical peut-il fournir un nouvel aperçu de la conception rationnelle de médicaments et conduirait à une meilleure compréhension de la mécanisme d'interaction entre les médicaments anti-cancéreux et de l'ADN, Journal of Photochemistry and Photobiology B: Biology, Elseiver 138 (2014) 36–4
[35] Frisch MJ,et al. (2009)Gaussian, Inc., Wallingford CT. 2009.
[36] Becke AD. Densityfunctional thermochemistry. III. The role of exact exchange J. Chem. Phys. 1993;98(7):5648-5662.
[37] Miehlich B, Savin A, Stoll H, Preuss H. Results obtained with the correlation energy density functionals of becke and Lee, Yang and Parr Chem. Phys. Lett. 1989;157(3-5):200-206.
[38] ADELIO R. MATAMALA, ALEJANDRO A. ALARCO´ N.(2011) A Simple Model for the Calculation of HOMO and LUMO Energy Levels
of Benzocatafusenes. International Journal of Quantum Chemistry, Vol 112, 1316–1322 (2012)
[39] Morris GM, Ruth H, Lindstrom W, Sanner MF, Belew RK, Goodsell DS, Olson AJ. Software news and updates AutoDock4 and AutoDockTools4: automated docking with selective receptor flexibility. J. Comput. Chem. 2009;30(16):2785-2791.
[40] Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE. The Protein Data Bank. Nucl. Acids Res. 2000;28(1): 235-242.
[41] Bandyopadhyay N, Pradhan AB, Das S, et al. Synthesis, structure, DFT calculations, electrochemistry, fluorescence, DNA binding and molecular docking aspects of a novel oxime based ligand and its palladium (II) complex. J Photochem Photobiol B Biol. 2016;160:336–346.
[42] Guhathakurta B Basu P, Purohit CS, et al. Synthesis, characterization, structure, DNA binding aspects and molecular docking study of a novel Schiff base ligand and its bis(μ-chloro) bridged Cu(II) dimer. Polyhedron. 2017;126:195–204.
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Published
2019-04-02
How to Cite
ADAIKA, A.; LANEZ, T.; LANEZ, E. IN VITRO AND IN SILICO EVALUATION OF ANTICANCER ACTIVITY OF N,N-DIMETHYLAMINOMETHYLFERROCENE. Journal of Fundamental and Applied Sciences, [S. l.], v. 11, n. 2, p. 748–768, 2019. DOI: 10.4314/jfas.v11i2.14. Disponível em: https://jfas.info/index.php/JFAS/article/view/289. Acesso em: 30 jan. 2025.
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