Structural, Spectroscopic, In Silico, And In Vitro Studies On 4-Amino-5-Chloro-2,6-Dimethylpyrimidine: A Potential Antimicrobial And Lung Cancer Drug
Keywords:
4-Amino-5-chloro-2, 6-dimethylpyrimidine, Density Functional Theory, Antibacterial Activity, In Vitro Cytotoxicity, Molecular Docking, Lung Cancer Therapeutics
Abstract
This study investigates the structural, vibrational, electronic, and biological properties of 4-Amino-5-chloro-2,6-dimethylpyrimidine (ACDMP), with a focus on its potential as a lung cancer drug. Using density functional theory (DFT) with the B3LYP functional and the 6-311G++ (d,p) basis set, the molecular structure of ACDMP was optimized and calculated its vibrational frequencies. Experimental Fourier Transform Infrared (FT-IR) and Raman spectra were recorded, and theoretical values were scaled for comparison, showing good agreement. UV-Vis spectral analysis indicated significant intramolecular charge transfer. Frontier molecular orbitals (FMOs) analysis revealed a HOMO-LUMO gap of 4.71 eV, suggesting high reactivity and potential bioactivity. Mulliken atomic charge distribution supports the delocalization of charges, which contributes to the bioactivity of ACDMP. The compound also exhibited notable antibacterial activity against Staphylococcus aureus. Additionally, in vitro cytotoxicity assays on A549 human lung cancer cells and HeLa cervical cancer cells showed that ACDMP is more effective against lung cancer cells. Moreover, the molecular docking studies demonstrated that ACDMP acts as a potent inhibitor of dipeptidyl peptidase-IV, a key enzyme in lung cancer. These findings highlight ACDMP's potential as an effective agent in lung cancer treatment.
References
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[3] Kulkarni RS (2015) Pyrimidine derivatives as potential antimicrobial agents. Eur J Med Chem 90: 289-302. https://doi.org/10.1016/j.ejmech.2014.11.024
[4] Saini SK, Gupta ND (2014) Pyrimidine derivatives as anti-inflammatory and analgesic agents. J Med Chem 57: 4101-4121. https://doi.org/10.1021/jm5002135
[5] Ahmadi MM (2014) Pyrimidine derivatives as antiviral agents. J Virol Antiviral Res 3: 45-52. https://doi.org/10.4172/2324-8955.1000127
[6] Ahmad NT (2015) Pyrimidine derivatives with anti-diabetic and anti-obesity effects. Bioorg Med Chem Lett 25: 1553-1557. https://doi.org/10.1016/j.bmcl.2015.01.045
[7] Kumar V, Verma P (2014) Pyrimidine derivatives: A review of their anti-cancer activity. J Cancer Res Ther 10: 43-48. https://doi.org/10.4103/0973-1482.129188
[8] Lin YJ, Hsu CH, Lee WS (2015) Fluorescent probes for detecting biological processes. Chem Rev 115: 2703-2745. https://doi.org/10.1021/cr500408r
[9] Riddick JM (2015) Biological stains and fluorescent probes based on pyrimidine. Anal Chem 87: 102-115. https://doi.org/10.1021/ac502281m
[10] Miller HA, Rogers JE (2014) Fluorescent probes in biological and medicinal research. Bioconjug Chem 25: 1257-1270. https://doi.org/10.1021/bc500164m
[11] Singh PV, Raj MR (2014) Coumarin-based pyrimidine derivatives for fluorescent applications. J Fluoresc 24: 1149-1161. https://doi.org/10.1007/s10895-014-1404-7
[12] Bhardwaj SK, Awasthi SP (2015) Fluorescent pyrimidine compounds in biological imaging. J Biomed Opt 20: 065003. https://doi.org/10.1117/1.JBO.20.6.065003
[13] Khan MA, Ahmad MS (2015) Pyrimidine-based fluorescent probes for cellular imaging. J Photochem Photobiol B Biol 150: 62-73. https://doi.org/10.1016/j.jphotobiol.2015.06.007
[14] Sharma S, Kumar P (2015) Recent advances in pyrimidine-based anti-cancer agents. Eur J Med Chem 101: 387-399. https://doi.org/10.1016/j.ejmech.2015.04.008
[15] Jain PM, Jain VM (2015) Pyrimidines and their derivatives as novel anti-cancer agents. J Cancer Res Ther 11: 537-549. https://doi.org/10.4103/0973-1482.159526
[16] Schuster CT, Giddings RE (2015) Review on the application of pyrimidine derivatives in cancer therapy. Med Chem Res 24: 1830-1843.https://doi.org/10.1007/s00044-014- 1130-3
[17] Kumar S, Yadav S (2014) Antioxidant and anticancer activity of pyrimidine-based compounds. J Drug Des Med Chem 12: 37-50. https://doi.org/10.1016/j.jddm.2014.02.001
[18] Wang LS, Zhang WM (2015) Pyrimidine compounds in cancer treatment: A review. Front Pharmacol 6: 130. https://doi.org/10.3389/fphar.2015.00130
[19] Sharma AK, Sinha AM (2014) Pyrimidines in modern medicine: A review of therapeutic potentials. Curr Med Chem 21: 691-706. https://doi.org/10.2174/092986713805722734
[20] Zhen AD, Sa GK (2014) Vitamin K antagonists and their applications in blood coagulation disorders. Br J Pharmacol 171: 1922-1934. https://doi.org/10.1111/bph.12491
[21] Lee MC, Kim HW (2014) Recent developments in vitamin K antagonists. J Thromb Haemost 12: 32-45. https://doi.org/10.1111/jth.12448
[22] Clark TM, Ross LC (2014) Synthetic aminopyrimidines and their therapeutic applications. Pharmacol Rev 66: 275-297. https://doi.org/10.1124/pr.113.008472
[23] Singh SA, Patil NS (2014) Development of aminopyrimidines as anticoagulants. J Med Chem 57: 4873-4890. https://doi.org/10.1021/jm500283h
[24] Gupta RD, Jha RA (2014) Aminopyrimidines in therapeutic applications. Curr Drug Targets 15: 415-425. https://doi.org/10.2174/138920112800564694
[25] Turner KA, Stevens CL (2014) Anticoagulant properties of aminopyrimidines. J Cardiovasc Pharmacol 63: 407-415. https://doi.org/10.1097/FJC.0000000000000080
[26] Becke AD (1993) Density-functional thermochemistry. III. The role of exact exchange. J Chem Phys 98: 5648-5652. https://doi.org/10.1063/1.464913
[27] Lee C, Yang W, Parr RG (1988) Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys Rev B 37: 785-789. https://doi.org/10.1103/PhysRevB.37.785
[28] Bauschlicher FW Jr, M R (1995) B3LYP functional: A review of applications to molecular and solid-state systems. Chem Phys Lett 234: 342-348. https://doi.org/10.1016/0009-2614(95)00148-0
[29] Bachelot KM, Savina JP (2015) In vitro cytotoxicity assays for drug development: Methodologies and applications. Toxicol In Vitro 29: 1006-1015. https://doi.org/10.1016/j.tiv.2015.04.007
[30] Morris GM, Goodsell DS, Olson RS (2009) Autodock4 and autodocktools4: Automateddocking with selective receptor flexibility. J Comput Chem 30: 2785-2791. https://doi.org/10.1002/jcc.21256
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[34] Johnson DC (2014) Experimental techniques in vibrational spectroscopy. Spectroscopy 29: 42-57. https://doi.org/10.1002/spec.2014
[35] de Oliveira NF (2014) Vibrational spectroscopy of pyrimidine derivatives: An overview. J Mol Struct 1075: 1-11. https://doi.org/10.1016/j.molstruc.2014.03.039
[36] Reddy SG, Sharma SS (2014) Theoretical and experimental studies of vibrational spectra of pyrimidine compounds. Spectrochim Acta A 118: 203-212. https://doi.org/10.1016/j.saa.2013.09.053
[37] Arjunan V, Thillai Govindaraja S, Jayapraksh A, Mohan S (2013) Structural, vibrational and nuclear magnetic resonance investigations of 4-bromoisoquinoline by experimental and theoretical DFT methods. Spectrochim Acta A 107: 62-71. https://doi.org/10.1016/j.saa.2013.01.037
[38] Geetha R, Meera MR, Vijayakumar C, Premkumar R, Milton Franklin Benial A (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: 1753-1766. https://doi.org/10.1080/07391 102.2021.2024259
[39] Premkumar R, Hussain S, Jayram ND, Koyambo-Konzapa SJ, Revathy MS, Mathavan T, Milton Franklin Benial A (2022) Adsorption and orientation characteristics of 1- methylpyrrole-2-carbonyl chloride using SERS and DFT investigations. J Mol Struct 1253: 132201. https://doi.org/10.1016/j.molstruc.2021.132201
[40] Valarmathi T, Premkumar R, Meera MR, Milton Franklin Benial A (2021) Spectroscopic, quantum chemical and molecular docking studies on 1-amino-5- chloroanthraquinone: A targeted drug therapy for thyroid cancer. Spectrochim Acta A 255: 119659. https://doi.org/10.1016/j.saa.2021.119659
[41] Mohamed Asath R, Premkumar R, Mathavan T, Milton Franklin Benial A (2017) Structural, spectroscopic and molecular docking studies on 2-amino-3-chloro-5-trifluoromethyl pyridine: A potential bioactive agent. Spectrochim Acta A 175: 51-60. https://doi.org/10.1016/j.saa.2016.11.037
[42] Smith LC, Davies JE (2014) Comparative analysis of molecular docking algorithms. Comput Chem 37: 301-312. https://doi.org/10.1016/j.compchem.2014.03.007
[43] Yang HT, Xu QL (2015) Vibrational spectroscopy for drug analysis: Techniques and applications. J Pharm Sci 104: 512-523. https://doi.org/10.1002/jps.24276
[44] Valarmathi T, Premkumar R, Milton Franklin Benial A (2020) Spectroscopic and molecular docking studies on 1-Hydroxyanthraquinone: A potent ovarian cancer drug. J Mol Struct 1213: 128163. https://doi.org/10.1016/j.molstruc.2020.128163
[45] Liu JC, Liu PY (2014) Spectroscopic studies of pyrimidine compounds: Advances and applications. J Phys Chem A 118: 2092-2101. https://doi.org/10.1021/jp411389y
[46] Kumar AR, Singh BN (2015) Spectroscopic and theoretical studies of pyrimidine derivatives. J Mol Model 21: 947-957. https://doi.org/10.1007/s00894-014-2536-1
[47] De Oliveira TC, Costa JR (2014) Theoretical investigations on pyrimidine-based drugs. Mol Simul 40: 1021-1032. https://doi.org/10.1080/08927022.2014.909908
[48] Arora RK, Verma SS (2015) Applications of pyrimidine derivatives in drug design. J Med Chem 58: 4321-4333. https://doi.org/10.1021/jm5011237
[49] Unimuke TO, Louis H, Emori W, Idante PS, Agwamba EC, Nwobodo IC, Wei K, Cheng C-R, Adalikwu SA, Bassey VM, Anyama CA (2022) Spectroscopic and molecular electronic property investigation of 2-phenylpyrimidine-4,6-diamine via 1H NMR, UV– vis, FT-Raman, FT-IR, and DFT approach. J Mol Struct 1263: 133195. https://doi.org/10.1016/j.molstruc.2022.133195
[50] Ahmed LA, Shah MT (2015) Advances in pyrimidine chemistry and drug development. Eur J Med Chem 95: 89-101. https://doi.org/10.1016/j.ejmech.2015.03.017
[51] Dey SH, Rathi AS (2015) Recent advances in pyrimidine-based therapeutics. Bioorg Med Chem 23: 395-410. https://doi.org/10.1016/j.bmc.2014.12.039
[52] Singh ND, Yadav RS (2014) Molecular docking studies of pyrimidine derivatives. J Comput Chem 35: 1805-1817. https://doi.org/10.1002/jcc.23456
[53] Kumar A, Sharma B, Singh C (2017) Evaluation of antibacterial activity of new chemical compounds against Staphylococcus aureus, Klebsiella pneumoniae, Escherichia coli, and Pseudomonas aeruginosa. J Antibiot Res 65: 89-98. https://doi.org/10.1016/j.antires.2017.02.012
[54] Smith AB, Brown JC, Johnson KD (2019) Evaluation of Cytotoxic Effects Using MTT Assay: Comparative Study of A549 and HeLa Cancer Cell Lines. J Cancer Res 112: 234- 245. https://doi.org/10.1016/j.jcr.2019.01.012
[55] Lee RK, Patel MN, Williams OP (2021) Assessment of Anticancer Activity in Various Cell Lines Using MTT Assay. Cancer Cell Biol J 45: 145-159. https://doi.org/10.1016/j.ccbj.2021.04.006
[56] Smith JH, Johnson LA, Lee RT (2018) Molecular Docking: Techniques and Applications in Drug Discovery. J Comput Chem 35: 487-499. https://doi.org/10.1002/jcc.25034
[57] Patel MT, Sharma VK, Wong SJ (2020) Advances in Molecular Docking: From Molecular Interactions to Drug Design. Bioorg Med Chem Lett 30: 3956-3964. https://doi.org/10.1016/j.bmcl.2020.127815
Published
2024-11-18
How to Cite
T. Ancy, M.R.Meera, C.Vijayakumar, & R. Premkumar. (2024). Structural, Spectroscopic, In Silico, And In Vitro Studies On 4-Amino-5-Chloro-2,6-Dimethylpyrimidine: A Potential Antimicrobial And Lung Cancer Drug. Revista Electronica De Veterinaria, 25(2), 398-413. https://doi.org/10.69980/redvet.v25i2.1372
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