Nanomeghyas

Nanomeghyas

Theoretical Study of the interaction of Chlorambucil and Melphalan with carbon nanotube surface as a drug nanocarrier in aqueous solution

Document Type : Original Article

Authors
Vahid Moradi, 1
sepideh ketabi 2
Marjaneh Samadizadeh 3
Elaheh Konoz, 1
Nasrin Masnabadi 4
1 Department of Chemistry, Islamic Azad University, Central Tehran Branch, Tehran, Iran
2 Department of pharmaceutical chemistry, Faculty of pharmaceutical chemistry, Tehran medical sciences, Islamic Azad University, Tehran, Iran
3 Department of Chemistry, Central Tehran Branch, Islamic Azad University, Tehran, Iran
4 Department of chemistry, Roudehen Branch, Islamic Azad University, Roudehen, Iran.
Abstract
Biological application of carbon nanotubes in drug delivery is our main concern in this investigation. For this purpose, possibility of the interaction of chlorambucil and melphalan with carbon nanotube surface as a carrier was studied in both gas phase and in aqueous media. At first step each species was modeled using quantum mechanical calculations, in the next step, solvation free energies and association free energies of considered structures in water were studied by Monte Carlo simulation and perturbation method. The results of density functional calculations in gas phase showed that both two drugs can interact with carbon nanotube. Monte Carlo simulation results revealed that interaction with carbon nanotube enhanced the solubility of drugs in water which improve the pharmaceutical applications. Calculated association free energies indicated that melphalan produced more stable complex with carbon nanotube than chorambucil in aqueous solution. This tendency could be observed in gas and liquid phase similarly.
Keywords
Monte Carlo simulation
carbon nanotube
solvation free energy
Chlorambucil
Melphalan
[1] T. Xu, N. Zhang, H.L. Nichols, D. Shi, X. Wen, Modification of nanostructured materials for biomedical applications, Materials Science and Engineering: C 27, 579-594, 2007.
[2] F. Danhier, E. Ansorena, J.M. Silva, R. Coco, A. Le Breton, V. Préat, PLGA-based nanoparticles: an overview of biomedical applications, Journal of controlled release 161, 505-522, 2012.
[3] Z. Liu, M. Winters, M. Holodniy, H. Dai, siRNA delivery into human T cells and primary cells with carbon‐nanotube transporters, Angewandte Chemie International Edition 46 ,2023-2027, 2007.
[4] M.R. McDevitt, D. Chattopadhyay, B.J. Kappel, J.S. Jaggi, S.R. Schiffman, C. Antczak, J.T. Njardarson, R. Brentjens, D.A. Scheinberg, Tumor targeting with antibody-functionalized, radiolabeled carbon nanotubes, Journal of Nuclear Medicine 48 , 1180-1189, 2007.
[5] M. Mohajeri, B. Behnam, A. Sahebkar, Biomedical applications of carbon nanomaterials: Drug and gene delivery potentials, Journal of cellular physiology 234 , 298-319, 2019.
[6] S. Ketabi, S.M. Hashemianzadeh, M. MoghimiWaskasi, Study of DNA base-Li doped SiC nanotubes in aqueous solutions: a computer simulation study, Journal of molecular modeling 19, 1605-1615, 2013.
[7] R.P. Feazell, N. Nakayama-Ratchford, H. Dai, S.J. Lippard, Soluble single-walled carbon nanotubes as longboat delivery systems for platinum (IV) anticancer drug design, Journal of the American Chemical Society 129, 8438-8439, 2007.
[8] S.K.S. Kushwaha, S. Ghoshal, A.K. Rai, S. Singh, Carbon nanotubes as a novel drug delivery system for anticancer therapy: a review, Brazilian Journal of Pharmaceutical Sciences 49, 629-643, 2013.
[9] K. Kostarelos, L. Lacerda, G. Pastorin, W. Wu, S. Wieckowski, J. Luangsivilay, S. Godefroy, D. Pantarotto, J.-P. Briand, S. Muller, Cellular uptake of functionalized carbon nanotubes is independent of functional group and cell type, Nature nanotechnology 2, 108-113, 2007.
[10] W. Yang, P. Thordarson, J.J. Gooding, S.P. Ringer, F. Braet, Carbon nanotubes for biological and biomedical applications, Nanotechnology 18, 412001,2007.
[11] S. Hampel, D. Kunze, D. Haase, K. Krämer, M. Rauschenbach, M. Ritschel, A. Leonhardt, J. Thomas, S. Oswald, V. Hoffmann, Carbon nanotubes filled with a chemotherapeutic agent: a nanocarrier mediates inhibition of tumor cell growth, (2008).
[12] Z. Liu, A.C. Fan, K. Rakhra, S. Sherlock, A. Goodwin, X. Chen, Q. Yang, D.W. Felsher, H. Dai, Supramolecular stacking of doxorubicin on carbon nanotubes for in vivo cancer therapy, Angewandte Chemie International Edition 48, 7668-7672, 2009.
[13] C. Samorì, H. Ali-Boucetta, R. Sainz, C. Guo, F.M. Toma, C. Fabbro, T. Da Ros, M. Prato, K. Kostarelos, A. Bianco, Enhanced anticancer activity of multi-walled carbon nanotube–methotrexate conjugates using cleavable linkers, Chemical Communications 46 , 1494-1496, 2010.
[14] S. Roosta, S.M. Hashemianzadeh, S. Ketabi, Encapsulation of cisplatin as an anti-cancer drug into boron-nitride and carbon nanotubes: Molecular simulation and free energy calculation, Materials Science and Engineering: C 67, 98-103, 2016.
[15] S. Ketabi, L. Rahmani, Carbon nanotube as a carrier in drug delivery system for carnosine dipeptide: A computer simulation study, Materials Science and Engineering: C 73, 173-181, 2017.
[16] N. Ershadi, R. Safaiee, M. Golshan, Functionalized (4, 0) or (8, 0) SWCNT as novel carriers of the anticancer drug 5-FU; a first-principle investigation, Applied Surface Science 536 , 147718, 2021.
[17] V. Moradi, S. Ketabi, M. Samadizadeh, E. Konoz, N. Masnabadi, Potentiality of carbon nanotube to encapsulate some alkylating agent anticancer drugs: a molecular simulation study, Structural Chemistry 32 ,869-877, 2021.
[18] S. Karimzadeh, B. Safaei, T.-C. Jen, Theorical investigation of adsorption mechanism of doxorubicin anticancer drug on the pristine and functionalized single-walled carbon nanotube surface as a drug delivery vehicle: A DFT study, Journal of Molecular Liquids 322,114890, 2021.
[19] Y. Ketabi, S. Ketabi, Simulation study of Li doped carbon nanotube as a carrier system for Aspirin in aqueous media, Nano Biomed. Eng 7, 20-27, 2015.
[20] G. Petersson, M.A. Al‐Laham, A complete basis set model chemistry. II. Open‐shell systems and the total energies of the first‐row atoms, The Journal of chemical physics 94, 6081-6090, 1991.
[21] M. Frisch, G. Trucks, H. Schlegel, G. Scuseria, M. Robb, J. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. Petersson, Gaussian 09; Gaussian, Inc, Wallingford, CT 32 ,5648-5652, 2009.
[22] N. Metropolis, A.W. Rosenbluth, M.N. Rosenbluth, A.H. Teller, E. Teller, Equation of state calculations by fast computing machines, The journal of chemical physics 21, 1087-1092, 1953.
[23] A.K. Rappé, C.J. Casewit, K. Colwell, W.A. Goddard III, W.M. Skiff, UFF, a full periodic table force field for molecular mechanics and molecular dynamics simulations, Journal of the American chemical society 114,10024-10035, 1992.
[24] J.-P. Hansen, I.R. McDonald, Theory of simple liquids: with applications to soft matter, Academic press,2013.
[25] W.L. Jorgensen, Transferable intermolecular potential functions for water, alcohols, and ethers. Application to liquid water, J. Am. Chem. Soc.;(United States) 103,1981.
[26] R.W. Zwanzig, High‐temperature equation of state by a perturbation method. I. Nonpolar gases, The Journal of Chemical Physics 22, 1420-1426, 1954.

  • Receive Date 30 April 2022
  • Revise Date 25 July 2022
  • Accept Date 16 August 2022