JOURNAL OF CHILEAN CHEMICAL SOCIETY

Vol 66 No 4 (2021): Journal of the Chilean Chemical Society
Original Research Papers

A QUANTUM MECHANICS AND MOLECULAR MECHANICS STUDY OF THE EFFECTS OF DIFFERENT SOLVENTS AND TEMPERATURES ON THE CONNECTIONS OF METHOTREXATE DERIVATIVES ANTICANCER DRUG TO NANOTUBES CARRIERS

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  • V. Khodadadi,
  • Neda Hasanzadeh,
  • H. Yahyaei,
  • A. Rayatzadeh
Neda Hasanzadeh
Department of Chemistry, Ahvaz Branch, Islamic Azad University, Ahvaz, Iran
Published December 29, 2021
Keywords
  • Quantum Monte Carlo (QMC), Single-wall carbon nanotubes (SWNTs), Boron nitride nanotubes (BNNTs), methotrexate derivatives anticancer drug, Solvent effect, force field.
How to Cite
Khodadadi, V., Hasanzadeh, N., Yahyaei, H., & Rayatzadeh, A. (2021). A QUANTUM MECHANICS AND MOLECULAR MECHANICS STUDY OF THE EFFECTS OF DIFFERENT SOLVENTS AND TEMPERATURES ON THE CONNECTIONS OF METHOTREXATE DERIVATIVES ANTICANCER DRUG TO NANOTUBES CARRIERS. Journal of the Chilean Chemical Society, 66(4), 5365-5379. Retrieved from https://www.jcchems.com/index.php/JCCHEMS/article/view/1868

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Abstract

In this study, the interactions of two effective derivatives of the methotrexate anticancer drug with Single-wall carbon nanotubes (SWNTs) and Boron nitride nanotubes (BNNTs) in the gas phase were investigated using the DFT calculations. Through the DFT method, the effects of different solvents on the interaction of methotrexate derivatives with SWNTs and BNNTs within the Onsager self-consistent reaction field (SCRF) model, as well as the effects of temperature on the stability of interactions between compounds in various solvents were studied. Thermodynamic parameters, Frontier Molecular Orbitals (FMOs) and Total Density of States (DOS) of the title compounds were also studied using theoretical calculations. Molecular properties of the structures such as the ionization potential (I), electron affinity (A), chemical hardness (η), electronic chemical potential (μ) and electrophilicity (ω) were investigated as well. Also, the interaction of methotrexate derivatives with SWNTs and BNNTs was examined via Amber, Opls, Charmm and MM+ force fields through the molecular mechanic (MM) method. The calculations were carried out through the Monte Carlo simulation methods at different temperatures. The effects of gas phase and various solvent media with different dielectric constants (water, DMSO, methanol, ethanol, CH2Cl2 and DMF) on the interaction of methotrexate derivatives were investigated using the aforementioned force fields. The most significant finding is that with respect to both thermodynamic properties and conformer populations, the Monte Carlo and Molecular Mechanics-Quantum Mechanics results are in agreement.

 

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References

  1. X. Li, Y. Peng, X. Qu, Nucleic Acids Research. 34, 3670, (2006)
  2. C. Klumpp, K. Kostarelos, M. Prato, A. Bianco, Biochimica et Biophysica Acta (BBA) - Biomembranes. 1758, 404, (2006)
  3. N. Sinha, J. T. W. Yeow, IEEE transitions on nanobioscience. 4, 180, (2005)
  4. N. Nishiyama, K. Kataoka, Pharmacology & therapeutics. 112, 630, (2006)
  5. H. Mizusako, T. Tagami, K. Hattori, T. Ozeki, Journal of pharmaceutical sciences. 104, 2934
  6. (2015)
  7. Q. He, J, Shi, Jurnal of Materials Chemistry. 21, 5845, (2011)
  8. G. Kwon, S. Suwa, M. Yokoyama, T. Okano, Y. Sakurai, K. Kataoka, Journal of Controlled Release. 29, 17, (1994)
  9. A. Mahmud, X. B. Xiong, H. M. Aliabadi, A. Lavasanifar, Journal of Drug Targeting. 15, 553 (2007)
  10. S. Khatri, N. G. Das, S. K. Das, Journal of pharmacy & bioallied sciences. 6, 297, (2014)
  11. J. E. Kim, J. Y. Shin, M. H. Cho, Archives of Toxicology. 86, 685, (2012)
  12. C. Sun, J. S. Lee, M. Zhang, Advanced drug delivery reviews. 60, 1252, (2008)
  13. R. Arenal, A. Lopez‐Bezanilla, Computational Molecular Science. 5, 299, (2015)
  14. G. Ciofani, Expert opinion on drug delivery. 7, 889, (2010)
  15. J. H. Kim, T.V. Pham, J. H. Hwang, C. S. Kim, M. J. Kim, Nano convergence. 5, 1, (2018)
  16. J. Iqbal, K. Ayub, Journal of Alloys and Compounds. 687, 976, (2016)
  17. D. Golberg,X. D. Bai, M. Mitome,C. C. Tang, C. Y. Zhi, Y. Bando, Acta materialia. 55, 1293, (2007)
  18. D. Lahiri, F. Rouzaud, T. Richard, A. K. Keshri, S. R. Bakshi, L. Kos, A. Agarwal, Acta biomaterialia. 6, 3524, (2010)
  19. W. An, C. H. Turner, the Journal of Physical Chemistry Letters. 1, 2269, (2010)
  20. C. W. Chang, W. Q. Han, A. Zettl, Journal of Vacuum Science & Technology B: Microelectronics and Nanometer Structures Processing, Measurement, and Phenomena. 23, 1883, (2005)
  21. T. He, T. Li, A. Huang, Z. Tang, X. Guan, Physica E: Low-dimensional Systems and Nanostructures. 107, 182, (2019)
  22. G. Ciofani, S. Danti, G. G. Genchi, B. Mazzolai, V. Mattoli, biocompatibility and potential spill‐over in nanomedicine. Small. 9, 1672, (2013)
  23. Z. Khatti, S. M. Hashemianzadeh, European Journal of Pharmaceutical Sciences. 88, 291, (2016)
  24. F. Azarakhshi, M. Sheikhi, S. Shahab, M. Khaleghian, K. Sirotsina, H. Yurlevich, D. Novik, Chemical Papers. 75, 1521, (2021)
  25. Z. Mahdavifar, R. Moridzadeh, Journal of Inclusion Phenomena and Macrocyclic Chemistry. 79, 443, (2014)
  26. P. N. Samanta, K. K. Das, RSC advances. 6, 92547, (2016)
  27. B. N. Cronstein, Arthritis & Rheumatism. 39, 1951, (1996)
  28. M. Wojtoniszak, K. Urbas, M. Perużyńska, M. Kurzawski, M. Droździk, E. Mijowska, Chemical Physics Letters. 568, 151, (2013)
  29. H. Matsuoka, N. Ohi, M. Mihara,H. Suzuki, K. Miyamoto, N. Maruyama, T. Kuroki, Journal of medicinal chemistry. 40, 105, (1997)
  30. T. M. Goszczyński, B, Filip‐Psurska, K. Kempińska, J. Wietrzyk, J. Boratyński, Pharmacology research & perspectives. 2, e00047, (2014)
  31. R. Segal, M. Yaron, B. Tartakovsky, arthritis and rheumatism. 20, 190, (1990)
  32. J. A. Moura, C. J. Valduga, E. R. Tavares, I. F. Kretzer, D. A. Maria, R. C. Maranhão, journal of nanomedicine. 6, 2285, (2011)
  33. S. Moura, J. Noro, P. Cerqueira, C. Silva, A. Cavaco-Paulo, A. Loureiro, International journal of pharmaceutics. 575, 118924, (2020)
  34. R. J. Kempton, A. M. Black, G. M. Anstead, A. A. Kumar, d. T. Blankenship, J. H. Freisheim, Journal of medicinal chemistry. 25, 475-(1982)
  35. A. Nemat, I. N. Khan, S. Kalsoom, S. A. Malik, S. Ayub, F. Adnan, M. A. Kamal, M. Iqbal, Journal of Biomolecular Structure and Dynamics. 38, 1, (2020)
  36. ‏ Y. Kokuryo, K. Kawata, T. Nakatani, A. Kugimiya, Y. Tamura, K. Kawada, M. Ohtani, Journal of medicinal chemistry. 40, 3280, (1997)
  37. S. Ekins, J. Mestres, B. Testa, British Journal of Pharmacology. 152, 21, (2007)
  38. L. Fraenkel, W. B. Nowell, G. Michel, C. Wiedmeyer. Annals of the Rheumatic Diseases. 77, 678, (2018)
  39. A. L. Mathews, A. Coleska, P. B. Burns, K. C. Chung, Arthritis Care & Research. 68, 318, (2016)
  40. P. Workman, Cold Spring Harbor Symposia on Quantitative Biology. 70, 499, (2005)
  41. I. Collins, P. Workman, Nature Chemical Biology. 2, 689, (2006)
  42. A. D. MacKerell, D. Bashford, M. Bellott, R. L. Dunbrack, Jr, J. D. Evanseck, M. J. Field, S. Fischer, J. Gao, H. Guo, S. Ha, D. Joseph-McCarthy, L. Kuchnir, K. Kuczera, F. T. K. Lau, C. Mattos, S. Michnick, T. Ngo, D. T. Nguye, B. Prodhom, W. E. Reiher, B. Roux, M. Schlenkrich, J. C Smith, R. Stote, J. Straub, M. Watanabe, J. Wiórkiewicz-Kuczera, D. Yin, M. Karplus, J. Phys. Chem. B. 102, 3586, (1998)
  43. A. D. MacKerell Jr, M. Feig, Journal of Computational Chemistry. 25, 1400, (2004)
  44. W. L. Jorgensen, D. S. Maxwell, J. Tirado-Rives, J. Am. Chem. Soc. 118, 11225, (1996)
  45. V. Hornak, R. Abel, A Okur, B. Strockbine, A. Roitberg, C. Simmerling, Proteins. 65, 712, (2006)
  46. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, O. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox, Gaussian 09 revision A02, Gaussian, Inc., Wallingford CT, 2009.
  47. A. Frisch, A. B. Nielson, A. J. Holder, 2000, GAUSSVIEW User Manual, Gaussian Inc.; Pittsburgh, PA.
  48. A. D.J. Becke, Chem. Phys. 98, 5648, (1993)
  49. J. Tomasi, B. Mennucci, R. Cammi, Chem. Rev. 105, 2999, (2005)
  50. S. Shahab, M. Sheikhi, L. Filippovich, E. Dikusar, H. Yahyaei, R. Kumar, M. Khaleghian, J Mol Struct. 1157, 536, (2018)
  51. H. Yahyaei, S. Sharifi, S. Shahab, M. Sheikhi. M. Ahmadianarog, Letters in Organic Chemistry. 18, 115, (2021)
  52. S. Shahab, M. Sheikhi, L. Filippovich, R. Kumar, E. Dikusar, H. Yahyaei, M. Khaleghian, Journal of Molecular Structure. 1148, 134, (2017)
  53. A. Szczepanska, J. L. Espartero, A. Moreno-Vargas, A. T. Carmona, I. Robina, S. Remmert, C. Parish, J. Org. Chem. 72, 6776, (2007)
  54. N. Metropolis, A. W. Rosenbluth, M. N. Rosenbluth, A. H. Teller, E. Teller, J. Chem. Phys. 21, 1087, (2004)
  55. HyperChem 7.0. (2001) Hypecube Inc., FL. Gainesville,
  56. H. Yahyaei, M. Monajjemi, H. Aghaie, K. Zare, Journal of Computational and Theoretical Nanoscience. 10, 2332, (2013)
  57. M. Kastner, Communications in Nonlinear Science and Numerical Simulation. 15, 1589, (2010)
  58. W. K. Hastings, Biometrika. 57, 97, (1970)
  59. J. S. Liu, F. Liang, W. H. Wong, Journal of the American Statistical Association. 95, 121, (2000)
  60. J. A. Champion, S. Mitragotri, Natl Aead Sei. 103, 4930, (2006)
  61. SL. Kinnings, N. Liu, N. Buchmeier, P. J. Tonge, L. Xie, P. E. Bourne, PLOS Computational Biology. 5, e1000423, (2009)
  62. I. Collins, P. Workman, Nature Chemical Biology. 2, 689, (2006)
  63. N. Scheinfeld, Dermatology online journal. 12, 15, (2006)
  64. BN. Cronstein, Pharmacol Rev. 57, 163, (2005)
  65. M. R. Sawaya, J. Kraut, Biochemistry, 36,586, (1997)
  66. L. M. Meyer, F. R. Miller, M. J. Rowen, G. Bock, J. Rutzky, Acta Haematologica. 4, 1571, (1950)

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