Integrated Spectroscopic, DFT, Molecular Docking and In Vitro Evaluation of 2,6-Diaminoanthraquinone: A Promising Lead for Lung Cancer
Keywords:
2,6-Diaminoanthraquinone; DFT; Vibrational analysis; Cytotoxicity; Molecular Docking; Lung Cancer
Abstract
The compound 2,6-Diaminoanthraquinone (DAAQ) was investigated through experimental (FT-IR, FT-Raman, UV-Vis) and theoretical (DFT, TD-DFT) approaches, along with in vitro cytotoxicity and molecular docking studies. The optimized molecular structure and vibrational frequencies were obtained using the B3LYP/cc-pVTZ basis set. The vibrational assignments were supported by PED analysis, showing good agreement with experimental spectra. UV-Vis analysis confirmed n→π* electronic transitions associated with the amino and carbonyl functionalities. The FMOs revealed a HOMO–LUMO gap of 2.85 eV, indicating charge transfer properties. Mulliken charge distribution and MEP surface confirmed the role of NH₂ groups and carbonyl oxygens in intramolecular charge transfer. Molecular docking revealed strong binding of DAAQ with lung cancer-related proteins, particularly DPP-4, while in vitro cytotoxicity assays demonstrated significant inhibition of A549 lung cancer cell growth compared to HeLa cervical cancer cells. These combined findings suggest that DAAQ is a promising candidate for targeted lung cancer therapy.
References
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[5] Duval J, Pecher V, Poujol M, Lesellier E (2016) Research advances for the extraction, analysis and uses of anthraquinones: A review. Ind Crops Prod. 94:812–833.
[6] Huang Q, Lu G, Shen HM, Chung MCM, Ong CN (2007) Anti-cancer properties of anthraquinones from rhubarb. Med Res Rev. 27:609–630.
[7] Schripsema J, Dagnino D (1996) Elucidation of the substitution pattern of 9,10-anthraquinones through the chemical shifts of peri-hydroxyl protons. Phytochemistry 42:177–184.
[8] Andersen DO, Weber ND, Wood SG, Hughes BG, Murray BK, North JA (1991) In vitro virucidal activity of selected anthraquinones and anthraquinone derivatives. Antiviral Res. 16:185–196.
[9] Valarmathi T, Premkumar R, Benial AMF (2020) Spectroscopic and molecular docking studies on 1-hydroxyanthraquinone: A potent ovarian cancer drug. J Mol Struct. 1213:128163.
[10] Geetha R, Meera MR, Vijayakumar C, Premkumar R, Benial AMF (2023) Synthesis, spectroscopic characterization, molecular docking and in vitro cytotoxicity investigations on 8-amino-6-methoxy quinolinium picrate: A novel breast cancer drug. J Biomol Struct Dyn. 41(5):1753–1766.
[11] Jamróz M.H. (2004) Vibrational Energy Distribution Analysis VEDA 4: Program for Vibrational Mode Analysis, Warsaw, Poland.
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[14] Jamróz M H (2004) Vibrational Energy Distribution Analysis VEDA 4: Program for Vibrational Mode Analysis, Warsaw, Poland.
[15] Dennington R, Keith T, Millam J (2009) GaussView, Version 5.0, Semichem Inc., Shawnee Mission, KS.
[16] Morris G M, Huey R, Lindstrom W, Sanner M F, Belew R K, Goodsell D S, Olson A J (2009) AutoDock4 and AutoDockTools4: Automated docking with selective receptor flexibility. J Comput Chem 30(16):2785–2791.
[17] Wesley U V, Tiwari S, Houghton A N (2004) Role for dipeptidyl peptidase IV in tumor suppression of human non-small cell lung carcinoma cells. Int J Cancer 109(6):855–866.
[18] Bulavin D V, Fornace A J (2004) p38 MAP kinase's emerging role as a tumor suppressor. Adv Cancer Res 92:95–118.
[19] Khan, M. S.; Kumar, S.; Choudhury, A. R. (2017) Structural, electronic, and vibrational study of anthraquinone derivatives: A DFT approach. J. Mol. Struct. 1134, 469–478.
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[25]K. Langeswaran, Saad AlGarni, M.Muthuramamoorthy, P. Saravanan, R. Premkumar*, R. Sangeetha (2025) 4-Fluorochalcone as a novel therapeutic agent for cervical cancer: An in-depth spectroscopic and computational study, Journal of Molecular Structure 1326 (2025) 141130.
[26] R. Geetha, M.R. Meera, C. Vijayakumar, R. Premkumar*, R. Govindharaju (2024) Synthesis, spectroscopic characterization, biological evaluation studies on 6-methoxy-8-nitroquinolinium picrate: A potent lung cancer drug, Journal of Molecular Structure 1317, 139029.
[27] Ganesan Venkatesh, Palanisamy Vennila, Savas Kaya, Samia Ben Ahmed, Paramasivam Sumathi, Vadivel Siva, Premkumar Rajendran, Chennapan Kamal (2024) Synthesis and Spectroscopic Characterization of Schiff Base Metal Complexes, Biological Activity, and Molecular Docking Studies, ACS Omega, DOI: 10.1021/acsomega.3c08526 (2024).
[28] V. Meenakumari, J. Mangaiyarkkarasi, R. Premkumar, R. Mohamed Asath, T. Thenmozhi, A. Milton Franklin Benial (2024) Spectroscopic Characterization, Quantum Chemical and Molecular Docking Investigations on Methyl Indole-3-Carboxylate: A Potent Cervical Cancer Drug, Journal of Molecular Structure, 1305(17) (2024) 137711.
Published
2024-12-10
How to Cite
Hima S, M.R. Meera, C.Vijayakumar, & R. Premkumar. (2024). Integrated Spectroscopic, DFT, Molecular Docking and In Vitro Evaluation of 2,6-Diaminoanthraquinone: A Promising Lead for Lung Cancer. Revista Electronica De Veterinaria, 25(2), 2219-2232. https://doi.org/10.69980/redvet.v25i2.2158
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Articles
