Molecular structure, homo-lumo analysis and vibrational spectroscopy of the cancer healing pro-drug temozolomide based on dft calculations

Ramesh Rijal; Hari Prasad Lamichhane; Kiran Pudasainee; Ramesh Rijal; Hari Prasad Lamichhane; Kiran Pudasainee

doi:10.3934/biophy.2022018

AIMS Biophysics

2022, Volume 9, Issue 3: 208-220. doi: 10.3934/biophy.2022018

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Molecular structure, homo-lumo analysis and vibrational spectroscopy of the cancer healing pro-drug temozolomide based on dft calculations

1.
Physics Department, St. Xavier's College, Kathmandu, Nepal
2.
Central Department of Physics, Tribhuvan University, Kirtipur, Kathmandu, Nepal

Received: 22 May 2022 Revised: 19 July 2022 Accepted: 25 July 2022 Published: 05 August 2022

The molecular structure and spectroscopic analysis of the Temozolomide molecule have been performed using the density functional theory in neutral and anion states as well as with the addition of DMSO solvent. The 6-311G(d) basis set was employed to optimize the molecular structure of the TMZ molecule using the DFT/B3LYP method. The HOMO-LUMO energies and MEP map were computed to determine the energy gap and probable sites of electrophilic and nucleophilic reactivity in the 6-311G+(d) basis set. The vibrational frequencies were calculated using a computational method and the major fundamental modes of vibration were assigned to their respective frequencies. The potential of the computational method to explain the vibrational modes was determined by comparing simulated spectra with experimental spectra. On isotope labeling of carbon, the frequency was shifted significantly.
- DMSO,
- HOMO-LUMO,
- TMZ,
- MEP,
- isotope labeling,
- energy gap,
- vibrational spectroscopy
Citation: Ramesh Rijal, Hari Prasad Lamichhane, Kiran Pudasainee. Molecular structure, homo-lumo analysis and vibrational spectroscopy of the cancer healing pro-drug temozolomide based on dft calculations[J]. AIMS Biophysics, 2022, 9(3): 208-220. doi: 10.3934/biophy.2022018

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Abstract

The molecular structure and spectroscopic analysis of the Temozolomide molecule have been performed using the density functional theory in neutral and anion states as well as with the addition of DMSO solvent. The 6-311G(d) basis set was employed to optimize the molecular structure of the TMZ molecule using the DFT/B3LYP method. The HOMO-LUMO energies and MEP map were computed to determine the energy gap and probable sites of electrophilic and nucleophilic reactivity in the 6-311G+(d) basis set. The vibrational frequencies were calculated using a computational method and the major fundamental modes of vibration were assigned to their respective frequencies. The potential of the computational method to explain the vibrational modes was determined by comparing simulated spectra with experimental spectra. On isotope labeling of carbon, the frequency was shifted significantly.

Acknowledgments

We are very thankful to the University Grant Commission of Nepal for providing financial support and to St. Xavier's College for providing computational support.

Conflict of interest

All authors declare no conflicts of interest in this paper.

References

[1]	Newlands ES, Stevens MFG, Wedge SR, et al. (1997) Temozolomide: a review of its discovery, chemical properties, pre-clinical development and clinical trials. Cancer Treat Rev 23: 35-61. https://doi.org/10.1016/S0305-7372(97)90019-0
[2]	Svec RL, McKee SA, Berry MR, et al. (2022) Novel imidazotetrazine evades known resistance mechanisms and is effective against temozolomide-resistant brain cancer in cell culture. ACS Chem Biol 17: 299-313. https://doi.org/10.1021/acschembio.2c00022
[3]	Wesolowski JR, Rajdev P, Mukherji SK (2010) Temozolomide (Temodar). Am J Neuroradiol 31: 1383-1384. https://doi.org/10.3174/ajnr.A2170
[4]	National Center for Biotechnology Information: PubChem Compound Summary for CID 11830328, Temozolomide Acid, 2022. Available from: https://pubchem.ncbi.nlm.nih.gov/compound/Temozolomide-Acid
[5]	Villano JL, Seery TE, Bressler LR (2009) Temozolomide in malignant gliomas: current use and future targets. Cancer Chemoth Pharm 64: 647-655. https://doi.org/10.1007/s00280-009-1050-5
[6]	Sansom C (1999) Temozolomide presents breakthrough in glioblastoma multiforme treatment. Pharm Sci Technol Toda y 4: 131-133.
[7]	Louis DN, Perry A, Reifenberger G, et al. (2016) The 2016 World Health Organization classification of tumors of the central nervous system: a summary. Acta Neuropathol 131: 803-820. https://doi.org/10.1007/s00401-016-1545-1
[8]	O'reilly SM, Newlands ES, Brampton M, et al. (1993) Temozolomide: A new oral cytotoxic chemotherapeutic agent with promising activity against primary brain tumours. Eur J Cancer 29: 940-942. https://doi.org/10.1016/S0959-8049(05)80198-4
[9]	Bower M, Newlands ES, Bleehen NM, et al. (1997) Multicentre CRC phase II trial of temozolomide in recurrent or progressive high-grade glioma. Cancer Chemoth Pharm 40: 484-488. https://doi.org/10.1007/s002800050691
[10]	Klepper B, Pauker D (2006) Medicare's drug plan: huge price disparities for common cancer drugs. Community Oncol 12: 753-755. https://doi.org/10.1016/S1548-5315(11)70942-1
[11]	Thomas A, Tanaka M, Trepel J, et al. (2017) Temozolomide in the era of precision medicine. Cancer Res 77: 823-826. https://doi.org/10.1158/0008-5472.CAN-16-2983
[12]	Kumer A, Sarker MN, Paul S (2019) The thermo physical, HOMO, LUMO, vibrational spectroscopy and QSAR study of morphonium formate and acetate ionic liquid salts using computational method. Turk Comput Theor Chem 3: 59-68. https://doi.org/10.33435/tcandtc.481878
[13]	Kumer A, Paul S, Sarker M, et al. (2019) The prediction of thermo physical, vibrational spectroscopy, chemical reactivity, biological properties of morpholinium borate, phosphate, chloride and bromide ionic liquid: a DFT study. Int J New Chem 6: 236-253. https://dx.doi.org/10.22034/ijnc.2019.110412.1053
[14]	Yahiaoui K, Seridi L, Mansouri K (2021) Temozolomide binding to Cucurbit[7]uril: QTAIM, NCI-RDG and NBO analyses. J Incl Phenom Macro Chem 99: 61-77. https://doi.org/10.1007/s10847-020-01027-5
[15]	Frisch MJ, Trucks GW, Schlegel HB, et al. (2009) Gaussian 09 Package. Wallingford, CT: Gaussian. Inc..
[16]	Becke A (1993) Density-functional thermochemistry.III. The role of exact exchange. J Chem Phys 98: 5648-5652. https://doi.org/10.1063/1.464913
[17]	Lee C, Yang W, Parr RG (1998) 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
[18]	Dennington R, Keith T, Millam J (2009) GaussView, Version 5.0. 8, R. Dennington: Semichem Inc.
[19]	Koopmans T (1934) Über die zuordnung von wellenfunktionen und eigenwerten zu den einzelnen elektronen eines atoms. Physica 1: 104-113. https://doi.org/10.1016/S0031-8914(34)90011-2
[20]	O'boyle NM, Tenderholt AL, Langner KM (2008) A library for package-independent computational chemistry algorithms. J Comput Chem 29: 839-845. https://doi.org/10.1002/jcc.20823
[21]	Jamróz MH (2013) Vibrational energy distribution analysis (VEDA): scopes and limitations. Spectrochim Acta A Mol Biomol Spectrosc 114: 220-230. https://doi.org/10.1016/j.saa.2013.05.096
[22]	Nkungli NK, Ghogomu JN (2017) Theoretical analysis of the binding of iron (III) protoporphyrin IX to 4-methoxyacetophenone thiosemicarbazone via DFT-D3, MEP, QTAIM, NCI, ELF, and LOL studies. J Mol Model 23: 200. https://doi.org/10.1007/s00894-017-3370-4
[23]	Krack M, Jug K (1996) Molecular electrostatic potentials for large systems. Theoretical and Computational Chemistry. Amsterdam: Elsevier 297-331. https://doi.org/10.1016/S1380-7323(96)80047-1
[24]	Gunasekaran S, Balaji RA, Kumaresan S, et al. (2008) Experimental and theoretical investigations of spectroscopic properties of N-acetyl-5-methoxytryptamine. Can J Anal Sci Spectrosc 53: 149-162.
[25]	Kumar PS, Vasudevan K, Prakasam A, et al. (2010) Quantum chemistry calculations of 3-Phenoxyphthalonitrile dye sensitizer for solar cells. Spectrochim Acta A Mol Biomol Spectrosc 77: 45-50. https://doi.org/10.1016/j.saa.2010.04.021
[26]	Sang-Aroon W, Ruangpornvisuti V, Amornkitbamrung V (2016) Tautomeric transformation of temozolomide, their proton affinities and chemical reactivities: a theoretical approach. J Mol Graph Model 66: 76-84. https://doi.org/10.1016/j.jmgm.2016.03.016
[27]	AlRabiah H, Muthu S, Al-Omary F, et al. (2017) Molecular structure, vibrational spectra, NBO, Fukui function, HOMO-LUMO analysis and molecular docking study of 6-[(2-methylphenyl)sulfanyl]-5-propylpyrimidine-2,4(1H,3H)-dione. Maced J Chem Chem Eng 36: 59-80. https://doi.org/10.20450/mjcce.2017.1001
[28]	Chen M, Waghmare UV, Friend CM, et al. (1998) A density functional study of clean and hydrogen-covered α-MoO3 (010): Electronic structure and surface relaxation. J Chem Phys 109: 6854-6860. https://doi.org/10.1063/1.477252
[29]	Mulliken RS (1955) Electronic population analysis on LCAO–MO molecular wave functions. J Chem Phys 23: 1833-1840. https://doi.org/10.1063/1.1740588
[30]	Socrates G (2004) Infrared and Raman Characteristic Group Frequencies: Tables and Charts. Chichester: John Wiley and Sons Ltd 12-14.
[31]	Sui H, Ju X, Liu X, et al. (2014) Primary thermal degradation effects on the polyurethane film. Polym Degrad Stabil 101: 109-113. https://doi.org/10.1016/j.polymdegradstab.2013.11.021
[32]	Wolpert M, Hellwig P (2006) Infrared spectra and molar absorption coefficients of the 20 alpha amino acids in aqueous solutions in the spectral range from 1800 to 500 cm⁻¹. Spectrochim Acta A Mol Biomol Spectrosc 64: 987-1001. https://doi.org/10.1016/j.saa.2005.08.025
[33]	Tanskanen H, Khriachtchev L, Lundell J, et al. (2004) Organo-noble-gas hydride compounds HKrCCH, HXeCCH, HXeCC, and HXeCCXeH: Formation mechanisms and effect of 13 C isotope substitution on the vibrational properties. J Chem Phys 121: 8291-8298. https://doi.org/10.1063/1.1799611

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