Assessment of drug loading and release efficiencies of zigzag (8, 0) single-walled carbon nanotube as a Bendamustine hydrochloride drug delivery system in silico: DFT approach

References

• Ijima S. Helical nanotubules of peptidic carbon. Nature. 1991;345(6348):56–58. 201902003682439724. https://doi.org/https://doi.org/10.1038/354056a0.
   Google Scholar
• Pantarotto D, Briand JP, Prato M, et al. Translocation of bioactive peptides across cell membranes by carbon nanotubes. Chem Comm. 2004;1(1,2004):16–17. 14737310. https://doi.org/https://doi.org/10.1039/b311254c.
   Google Scholar
• Wang R, Zhang D. Theoretical study of the adsorption of carbon monoxide on pristine and silicon-doped boron nitride nanotubes. Aust J Chem. 2008;61(12):941–945. 95881861. https://doi.org/https://doi.org/10.1071/CH08226.
   Web of Science ®Google Scholar
• Kam NWS, Jessop TC, Wender PA, et al. Nanotube molecular transporters: internalization of carbon nanotube− protein conjugates into mammalian cells. J Am Chem Soc. 2004;126(22):6850–6851.
   PubMed Web of Science ®Google Scholar
• Trzaskowski B, Jalbout AF, Adamowicz L. Molecular dynamics studies of protein-fragment models encapsulated into carbon nanotubes. Chem Phys Lett. 2006;430(1–3):97–100.
   Web of Science ®Google Scholar
• Elhissi A, Ahmed W, Hassan IU, etal Carbon nanotubes in cancer therapy and drug delivery. J Drug Deliv. 2012;2012:837327.
   PubMedGoogle Scholar
• Adeli M, Soleyman R, Beiranvand Z, et al. Carbon nanotubes in cancer therapy: a more precise look at the role of carbon nanotube–polymer interactions. Chem Soc Rev. 2013;42(12):5231–5256.
   PubMed Web of Science ®Google Scholar
• Ahmed W, Elhissi A, Dhanak V, et al. Carbon nanotubes: applications in cancer therapy and drug delivery research. In Subramani k. and Ahmed W. (Eds.): Emerging nanotechnologies in dentistry. William Andrew Publishing; 2018. p. 371–389.
   Google Scholar
• Mortazavifar A, Raissi H, Shahabi M. Comparative prediction of binding affinity of hydroxyurea anti-cancer to boron nitride and carbon nanotubes as smart targeted drug delivery vehicles. J Biomol Struct Dyn. 2019;37(18):4852–4862.
   PubMed Web of Science ®Google Scholar
• Pakdel M, Raissi H, Shahabi M. Predicting doxorubicin drug delivery by single-walled carbon nanotube through cell membrane in the absence and presence of nicotine molecules: a molecular dynamics simulation study. J Biomol Struct Dyn. 2020;38(5):1488–1498.
   PubMed Web of Science ®Google Scholar
• Ghadri Z, Raissi H, Shahabi M, et al. Molecular dynamics simulation study of glycine tip-functionalisation of single-walled carbon nanotubes as emerging nanovectors for the delivery of anticancer drugs. Mol Simul. 2020;46(2):111–120.
   Web of Science ®Google Scholar
• Khatti Z, Hashemianzadeh SM, Shafiei SA. A molecular study on drug delivery system based on carbon nanotube compared to silicon carbide nanotube for encapsulation of platinum-based anticancer drug. Adv Pharm Bull. 2018;8(1):163–167.
   PubMedGoogle Scholar
• Panczyk T, Wolski P, Lajtar L. Coadsorption of doxorubicin and selected dyes on carbon nanotubes. Theoretical investigation of potential application as a pH-controlled drug delivery system. Langmuir. 2016;32(19):4719–4728.
   PubMed Web of Science ®Google Scholar
• Khatti Z, Hashemianzadeh SM. Investigation of thermodynamic and structural properties of drug delivery system based on carbon nanotubes as a carboplatin drug carrier by molecular dynamics simulations. J Incl Phenom Macrocycl Chem. 2015;83(1–2):131–140.
   Web of Science ®Google Scholar
• Balamurugan K, Baskar P, Mahesh Kumar R, et al. Interaction of carbon nanotube with ethylene glycol–water binary mixture: a molecular dynamics and density functional theory investigation. J Phys Chem C. 2012;116(7):4365–4373.
   Web of Science ®Google Scholar
• Arsawang U, Saengsawang O, Rungrotmongkol T, et al. How do carbon nanotubes serve as carriers for gemcitabine transport in a drug delivery system? J Mol Graph Model. 2011;29(5):591–596.
   PubMed Web of Science ®Google Scholar
• Chen Z, Pierre D, He H, et al. Adsorption behavior of epirubicin hydrochloride on carboxylated carbon nanotubes. Int J Pharm. 2011;405(1-2):153–161.
   PubMed Web of Science ®Google Scholar
• Liu Z, Sun X, Nakayama-Ratchford N, et al. Supramolecular chemistry on water-soluble carbon nanotubes for drug loading and delivery. ACS Nano. 2007;1(1):50–56.
   PubMed Web of Science ®Google Scholar
• Ali-Boucetta H, Al-Jamal KT, McCarthy D, et al. Multiwalled carbon nanotube–doxorubicin supramolecular complexes for cancer therapeutics. Chem Commun. 2008;4:459–461.
   PubMed Web of Science ®Google Scholar
• Izadyar A, Farhadian N, Chenarani N. Molecular dynamics simulation of doxorubicin adsorption on a bundle of functionalized CNT. J Biomol Struct Dyn. 2016;34(8):1797–1805.
   PubMed Web of Science ®Google Scholar
• Hashemzadeh H, Raissi H. The functionalization of carbon nanotubes to enhance the efficacy of the anticancer drug paclitaxel: a molecular dynamics simulation study. J Mol Model. 2017;23:222–232.
   PubMed Web of Science ®Google Scholar
• Li Z, Tozer T, Alisaraie L. Molecular dynamics studies for optimization of noncovalent loading of vinblastine on single-walled carbon nanotube. J Phys Chem C. 2016;120:4061–4070.
   Web of Science ®Google Scholar
• Kamel M, Raissi H, Morsali A. Theoretical study of solvent and co-solvent effects on the interaction of flutamide anticancer drug with carbon nanotube as a drug delivery system. J Mol Liq. 2017;248:490–500.
   Web of Science ®Google Scholar
• Bhirde AA, Sousa AA, Patel V, et al. Imaging the distribution of individual platinum-based anticancer drug molecules attached to single-wall carbon nanotubes. Nanomedicine. 2009;4(7):763–772.
   PubMed Web of Science ®Google Scholar
• Khorram R, Raissi H, Morsali A, et al. The computational study of the γ-Fe2O3 nanoparticle as carmustine drug delivery system: DFT approach. J Biomol Struct Dyn. 2019;37(2):454–464.
   PubMed Web of Science ®Google Scholar
• Dubbelman AC, Rosing H, Darwish M, et al. Pharmacokinetics and excretion of 14 C-bendamustine in patients with relapsed or refractory malignancy. Drugs R D. 2013;13(1):17–28.
   PubMedGoogle Scholar
• Sohanian M, Fazaeli R. Study of the mechanism of interaction of oxaliplatin anticancer drug with guanine DNA constituent bases by Ab initio method. The First National Conference on New Technologies in Chemistry and Chemical Engineering, Tehran, Vista Scientific Research Cooperative, 2017.
   Google Scholar
• Miertuš S, Scrocco E, Tomasi J. Electrostatic interaction of a solute with a continuum. A direct utilizaion of AB initio molecular potentials for the prevision of solvent effects. Chem Phys. 1981;55(1):117–129.
   Web of Science ®Google Scholar
• Floris FM, Tomasi J, Ahuir JP. Dispersion and repulsion contributions to the solvation energy: refinements to a simple computational model in the continuum approximation. J Comput Chem. 1991;12(7):784–791.
   Web of Science ®Google Scholar
• Glendening ED, Badenhoop JK, Reed AE, et al. Theoretical chemistry institute. Madison: University of Wisconsin; 2001.
   Google Scholar
• Kiani MK, Ghasemi AS, Ravari F. Theoretical study on carbonaceous materials as high efficient carriers for crizotinib drug in liquid water by density functional theory approach. Struct Chem. 2020;31(4):1553–1561.
   Web of Science ®Google Scholar
• Moradnia H, Raissi H, Bakhtiari A. A density functional theory-based analysis of the structural, topological and electronic properties of gemcitabine drug adsorption on the pyrrolidine functionalized single-walled carbon nanotube. J Biomol Struct Dyn. 2019;37(10):2477–2486.
   PubMed Web of Science ®Google Scholar
• Zaboli M, Raissi H. The influence of nicotine on pioglitazone encapsulation into carbon nanotube: the investigation of molecular dynamic and density functional theory. J Biomol Struct Dyn. 2017;35(3):520–534.
   PubMed Web of Science ®Google Scholar
• Kamel M, Raissi H, Morsali A, et al. Assessment of the adsorption mechanism of flutamide anticancer drug on the functionalized single-walled carbon nanotube surface as a drug delivery vehicle: an alternative theoretical approach based on DFT and MD. Appl Surf Sci. 2018;434:492–503.
   Web of Science ®Google Scholar
• Shahabi M, Raissi H. Screening of the structural, topological, and electronic properties of the functionalized graphene nanosheets as potential tegafur anticancer drug carriers using DFT method. J Biomol Struct Dyn. 2018;36(10):2517–2529.
   PubMed Web of Science ®Google Scholar
• Boys SF, Bernardi FJ. The calculation of small molecular interactions by the differences of separate total energies. Some procedures with reduced errors. Mol Phys. 1970;19(4):553–566.
   Web of Science ®Google Scholar
• Parr RG. PR Absolute hardness: companion parameter to absolute electronegativity. J Am Chem Soc. 1983;105:7512–7516.
   Web of Science ®Google Scholar
• Fukui K. Role of frontier orbitals in chemical reactions. Science. 1982;218(4574):747–754.
   PubMed Web of Science ®Google Scholar
• Pearson RG. Absolute electronegativity and hardness: applications to organic chemistry. J Org Chem. 1989;54(6):1423–1430.
   Web of Science ®Google Scholar
• Sarmah A, Saha S, Bagaria P, et al. On the complementarity of comprehensive decomposition analysis of stabilization energy (CDASE)–scheme and supermolecular approach. Chem Phys. 2012;394(1):29–35.
   Web of Science ®Google Scholar
• Frisch MJ, Trucks GW, Schlegel HB, et al. Gaussian 03. Pittsburgh (PA): Gaussian.
   Google Scholar
• Zhao Y, Truhlar DG. The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other functionals. Theor Chem Acc. 2008;120(1):215–241.
   Web of Science ®Google Scholar
• Zhao Y, Schultz NE, Truhlar DG. Design of density functionals by combining the method of constraint satisfaction with parametrization for thermochemistry, thermochemical kinetics, and noncovalent interactions. J Chem Theory Comput. 2006;2(2):364–382.
   PubMed Web of Science ®Google Scholar
• Zhao Y, Truhlar DG. A density functional that accounts for medium-range correlation energies in organic chemistry. Org Lett. 2006;8(25):5753–5755.
   PubMed Web of Science ®Google Scholar
• Huenerbein R, Schirmer B, Moellmann J, et al. Effects of London dispersion on the isomerization reactions of large organic molecules: a density functional benchmark study. Phys Chem Chem Phys. 2010;12(26):6940–6948.
   PubMed Web of Science ®Google Scholar
• Rayne S, Forest K. Theoretical studies on the pK∼ a∼ values of perfluoroalkyl carboxylic acids. Nat Preced. 2010; 949: 60–69.
   Google Scholar
• Srimathi U, Nagarajan V, Chandiramouli R. Interaction of imuran, pentasa and hyoscyamine drugs and solvent effects on graphdiyne nanotube as a drug delivery system - a DFT study. J Mol Liq. 2018;265:199–207.
   Web of Science ®Google Scholar
• Nagarajan V, Chandiramouli R. A study on quercetin and 5-fluorouracil drug interaction on graphyne nanosheets and solvent effects—a first-principles study. J Mol Liq. 2019;275:713–722.
   Web of Science ®Google Scholar
• Pencheva I, Bogomilova A, Koseva N, et al. HPLC study on the stability of bendamustine hydrochloride immobilized onto polyphosphoesters. J Pharm Biomed Anal. 2008;48(4):1143–1150.
   PubMed Web of Science ®Google Scholar