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Synthesis of Isatin Monohydrazone, Spectroscopic Analysis, DFT Studies, and Molecular Docking Applications to MCF-7 Cell Line

Year 2025, Volume: 46 Issue: 1, 41 - 47, 25.03.2025

Ceylan Alkaya Yıldız , Sultan Erkan

https://doi.org/10.17776/csj.1500189

Abstract

In this study, 3-hydrazinoindolin-2-one (S), an isatin monohydrazone compound, was synthesized. Spectroscopic (IR and 1H-NMR) analyses were performed for the synthesized isatin monohydrazone compound. To compare the experimental spectroscopic data obtained, isatin was optimized at B3LYP/6-31G(d,p). The calculated data were found to be compatible with the experimental data obtained for structural analysis. Contour diagrams and MEP maps were also obtained to identify the electrophilic and nucleophilic attack sites of the synthesis compound. To evaluate their compatibility with biomolecular system, the synthesized compounds were fused with target protein representing MCF-7 cell line. The PDB ID of the synthesized compound: 1M17 and 3HY3 were calculated as -5.70 and -5.73 kcal/mol with the target proteins, respectively. Based on the obtained molecular docking parameters, it was determined to be suitable for anti-cancer applications

Keywords

Synthesis Computational chemistry Molecular docking

References

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  • [26] Erkan S., Structural, Spectroscopic and Anti-Cancer Properties of Hydroxy-and Sulfonamide-Azobenzene Platinum (II) Complexes: DFT and Molecular Docking Studies, Cumhuriyet Science Journal, 39(4) (2018) 1036-1051.
  • [27] Stamos J., Sliwkowski M.X., Eigenbrot C., Epidermal Growth Factor Receptor Tyrosine Kinase Domain with 4-Anilinoquinazoline İnhibitor Erlotinib, URL https://doi. org/10.2210/pdb1m17/pdb., sep 2002.
  • [28] Wu D., Li Y., Song G., Cheng C., Zhang R., Joachimiak A., Liu Z.J., Structural Basis for the İnhibition of Human 5, 10-Methenyltetrahydrofolate Synthetase by N10-Substituted Folate Analogues, Cancer Research, 69(18) (2009) 7294-7301.
  • [29] Erkan S., Karakaş D., DFT İnvestigation and Molecular Docking Studies on Dinuclear Metal Carbonyls Containing Pyridyl Ligands with Alkyne Unit, Chemical Papers, 73 (2019) 2387-2398.

Year 2025, Volume: 46 Issue: 1, 41 - 47, 25.03.2025

Ceylan Alkaya Yıldız , Sultan Erkan

https://doi.org/10.17776/csj.1500189

Abstract

References

  • [1] Kaya Y., Erçağ, A., Serdaroğlu G., Kaya S., Grillo I.B., Rocha G.B., Synthesis, Spectroscopic Characterization, DFT Calculations, and Molecular Docking Studies of New Unsymmetric Bishydrazone Derivatives, Journal of Molecular Structure, (2021) 1244, 131224.
  • [2] Mathur G., Nain S., Recent Advancement in Synthesis of İsatin as Anticonvulsant Agents: A review, Med chem., 4(4) (2014) 417-27.
  • [3] Cheke R.S., Patil V.M., Firke S.D., Ambhore J.P., Ansari I.A., Patel H.M., Snoussi M., Therapeutic Outcomes of İsatin and its Derivatives Against Multiple Diseases: Recent Developments in Drug Discovery, Pharmaceuticals, 15(3) (2022) 272.
  • [4] Nath R., Pathania S., Grover G., Akhtar M.J., Isatin Containing Heterocycles for Different Biological Activities: Analysis of Structure Activity Relationship, Journal of Molecular Structure, 1222 (2020) 128900.
  • [5] Vine K.L., Locke J.M., Ranson M., Pyne S.G., Bremner J.B., In Vitro Cytotoxicity Evaluation of Some Substituted İsatin Derivatives, Bioorganic & Medicinal Chemistry, 15(2) (2007) 931-938.
  • [6] Murukan B., Mohanan K., Synthesis, Characterization and Antibacterial Properties of Some Trivalent Metal Complexes With [(2-Hydroxy-1-Naphthaldehyde)-3-İsatin]-Bishydrazone, Journal of Enzyme Inhibition and Medicinal Chemistry, 22(1) (2007) 65-70.
  • [7] Pandeya S. N., Sriram D., Nath G., De Clercq E., Synthesis and Antimicrobial Activity of Schiff and Mannich Bases of İsatin and its Derivatives With Pyrimidine, Il Farmaco, 54(9) (1999) 624-628.
  • [8] Retnam C.G., Rose S.V., Kumari B.S., Synthesis, Characterization, Biological Activity and Molecular Docking Study of Transition Metal Complexes from Heterocyclic Ligand System, Journal of Molecular Structure, 1282 (2023) 135162.
  • [9] Ernzerhof M., Scuseria G.E., Perspective on “Inhomogeneous Electron Gas” (2000). Hohenberg P, Kohn W., Phys Rev 136: B864, Theoretical Chemistry Accounts, 103 (1964) 259-262.
  • [10] Stamos J., Sliwkowski M.X., Eigenbrot C., Structure of the Epidermal Growth Factor Receptor Kinase Domain Alone and in Complex With a 4-Anilinoquinazoline İnhibitor, Journal of Biological Chemistry., 277(48) (2002) 46265-46272.
  • [11] Wu D., Li Y., Song G., Cheng C., Zhang R., Joachimiak A., Liu Z. J., Structural Basis for the İnhibition of Human 5, 10-Methenyltetrahydrofolate Synthetase by N10-Substituted Folate Analogues, Cancer Research, 69(18) (2009) 7294-7301.
  • [12] Dennington R., Keith T.A., & Millam J.M., GaussView Version 6.1. In., (2016).
  • [13] Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Scalmani G., Barone V., Petersson G.A., Nakatsuji H., Li X., Caricato M., Marenich A. V., Bloino J., Janesko B. G., Gomperts R., Mennucci B., Hratchian H.P., Ortiz J.V., Fox D.J., Gaussian 16 Rev. C.01. In., (2016).
  • [14] Becke A.D., Density‐Functional Thermochemistry. I. The Effect of the Exchange‐Only Gradient Correction, The Journal of Chemical Physics, 96(3) (1992) 2155-2160.
  • [15] Blaudeau J.P., McGrath M.P., Curtiss L.A., Radom L., Extension of Gaussian-2 (G2) Theory to Molecules., (1997).
  • [16] Phillips J.C., Generalized Koopmans' Theorem, Physical Review, 123(2) (1961) 420.
  • [17] Stewart J.J., Stewart computational Chemistry, http://openmopac. net/., (2007).
  • [18] Bikadi Z., Hazai E., Application of the PM6 Semi-Empirical Method to Modeling Proteins Enhances Docking Accuracy of AutoDock, Journal of Cheminformatics., 1 (2009) 1-16.
  • [19] Huey R., Morris G.M., Olson A.J., Goodsell D.S., A Semiempirical Free Energy Force Field with Charge‐Based Sesolvation, Journal of Computational Chemistry, 28(6) (2007) 1145-1152.
  • [20] Devi J., Batra N., Synthesis, Characterization and Antimicrobial Activities of Mixed Ligand Transition Metal Complexes with İsatin Monohydrazone Schiff Base Ligands and Heterocyclic Nitrogen Base, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 135 (2015) 710-719.
  • [21] Kaya S., Erkan S., Karakaş D., Computational İnvestigation of Molecular Structures, Spectroscopic Properties and Antitumor-Antibacterial Activities of Some Schiff Bases, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 244 (2021) 118829.
  • [22] Özdemir E.Ç., Akyol H., The Development of a Reading Comprehension Test, Universal Journal of Educational Research, 7(2) (2019) 563-570.
  • [23] Küçükterzi Ö., Theoretical İnvestigation of the Structure and Spectroscopic Properties of N-trans-Cinnamilidene-M-Toluidine Schiff Base Molecule by DFT and HF Methods, Master's thesis, Ankara University (Turkey)., (2020).
  • [24] Khalid H.H., Erkan S., Bulut N., Halogens Effect on Spectroscopy, Anticancer and Molecular Docking Studies for Platinum Complexes, Optik, 244 (2021) 166324.
  • [25] Kaya S., Erkan S., Karakaş D., Computational İnvestigation of Molecular Structures, Spectroscopic Properties and Antitumor-Antibacterial Activities of Some Schiff Bases, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 244 (2021) 118829.
  • [26] Erkan S., Structural, Spectroscopic and Anti-Cancer Properties of Hydroxy-and Sulfonamide-Azobenzene Platinum (II) Complexes: DFT and Molecular Docking Studies, Cumhuriyet Science Journal, 39(4) (2018) 1036-1051.
  • [27] Stamos J., Sliwkowski M.X., Eigenbrot C., Epidermal Growth Factor Receptor Tyrosine Kinase Domain with 4-Anilinoquinazoline İnhibitor Erlotinib, URL https://doi. org/10.2210/pdb1m17/pdb., sep 2002.
  • [28] Wu D., Li Y., Song G., Cheng C., Zhang R., Joachimiak A., Liu Z.J., Structural Basis for the İnhibition of Human 5, 10-Methenyltetrahydrofolate Synthetase by N10-Substituted Folate Analogues, Cancer Research, 69(18) (2009) 7294-7301.
  • [29] Erkan S., Karakaş D., DFT İnvestigation and Molecular Docking Studies on Dinuclear Metal Carbonyls Containing Pyridyl Ligands with Alkyne Unit, Chemical Papers, 73 (2019) 2387-2398.
There are 29 citations in total.

Details

Primary Language English
Subjects Bioinorganic Chemistry
Journal Section Natural Sciences
Authors

Ceylan Alkaya Yıldız 0000-0003-0322-2699

Sultan Erkan 0000-0001-6744-929X

Publication Date March 25, 2025
Submission Date June 12, 2024
Acceptance Date March 8, 2025
Published in Issue Year 2025Volume: 46 Issue: 1

Cite

APA Alkaya Yıldız, C., & Erkan, S. (2025). Synthesis of Isatin Monohydrazone, Spectroscopic Analysis, DFT Studies, and Molecular Docking Applications to MCF-7 Cell Line. Cumhuriyet Science Journal, 46(1), 41-47. https://doi.org/10.17776/csj.1500189
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