Adsorption behavior of mercaptopurine and 6-thioguanine drugs on the B₁₂N₁₂, AlB₁₁N₁₂ and GaB₁₁N₁₂ nanoclusters, a comparative DFT study

References

• Abdel-Latif, M. K., Abd El-Mageed, H. R., Mohamed, H. S., & Mustafa, F. M. (2020). Study the solvation effect on 6-phenyl-2-thioxo-1, 2-dihydropyridine-3-carbonitrile derivatives by TD-DFT calculations and molecular dynamics simulations. Journal of Molecular Structure, 1200, 127056. https://doi.org/10.1016/j.molstruc.2019.127056
   Web of Science ®Google Scholar
• Abdolahi, N. (2018). Adsorption of celecoxib on B12N12 fullerene: Spectroscopic and DFT/TD-DFT study. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 204, 348–353. https://doi.org/10.1016/j.saa.2018.06.077
   PubMed Web of Science ®Google Scholar
• Abdolahi, N., Singla, P., Soltani, A., Javan, M., Aghaei, M., Heidari, F., & Sedighi, S. (2020). Gold decorated B12N12 nanocluster as an effective sulfasalazine drug carrier: A theoretical investigation. Physica E: Low-Dimensional Systems and Nanostructures, 124, 114296. https://doi.org/10.1016/j.physe.2020.114296
   Web of Science ®Google Scholar
• Ahmadi Peyghan, A., Hadipour, N., & Bagheri, Z. (2013). Effects of Al doping and double-antisite defect on the adsorption of HCN on a BC 2 N nanotube: Density functional theory studies. The Journal of Physical Chemistry C, 117(5), 2427–2432. https://doi.org/10.1021/jp312503h
   Web of Science ®Google Scholar
• Aihara, J. I. (1999). Reduced HOMO-LUMO gap as an index of kinetic stability for polycyclic aromatic hydrocarbons. The Journal of Physical Chemistry A, 103(37), 7487–7495. https://doi.org/10.1021/jp990092i
   Web of Science ®Google Scholar
• Baei, M. T., Bagheri, Z., & Peyghan, A. A. (2013). Transition metal atom adsorptions on a boron nitride nanocage. Structural Chemistry, 24(4), 1039–1044. https://doi.org/10.1007/s11224-012-0132-x
   Web of Science ®Google Scholar
• Baei, M. T., Kanani, Y., Rezaei, V. J., & Soltani, A. (2014). Adsorption phenomena of gas molecules upon Ga-doped BN nanotubes: A DFT study. Applied Surface Science, 295, 18–25. https://doi.org/10.1016/j.apsusc.2013.12.136
   Web of Science ®Google Scholar
• Beheshtian, J., Baei, M. T., & Peyghan, A. A. (2012). Theoretical study of CO adsorption on the surface of BN, AlN, BP and AlP nanotubes. Surface Science, 606(11-12), 981–985. https://doi.org/10.1016/j.susc.2012.02.019
   Web of Science ®Google Scholar
• Bertino, J. R., Waud, W. R., & Parker, W. B. (2011). Targeting tumors that lack methylthioadenosine phosphorylase (MTAP) activity: Current strategies. Cancer Biology & Therapy, 11, 627–632. https://doi.org/10.4161/cbt.11.7.14948
   PubMed Web of Science ®Google Scholar
• Bezi Javan, M., Soltani, A., Ghasemi, A. S., Tazikeh Lemeski, E., Gholami, N., & Balakheyli, H. (2017). Ga-doped and antisite double defects enhance the sensitivity of boron nitride nanotubes towards Soman and Chlorosoman. Applied Surface Science, 411, 1–10. https://doi.org/10.1016/j.apsusc.2017.03.187
   Web of Science ®Google Scholar
• Bezi Javan, M., Soltani, A., Tazikeh Lemeski, E., Ahmadi, A., & Moazen Rad, S. (2016). Interaction of B12N12 nano-cage with cysteine through various functionalities: A DFT study. Superlattices and Microstructures, 100, 24–37. https://doi.org/10.1016/j.spmi.2016.08.035
   Web of Science ®Google Scholar
• Burchenal, J. H., Murphy, M. L., Ellison, R. R., Sykes, M. P., Tan, T. C., Leone, L. A., Karnof-Sky, D. A., Craver, L. F., Dargeon, H. W., & Rhoads, C. P. (1953). Clinical evaluation of a new antimetabolite, 6-mercaptopurine, in the treatment of acute leukemia and allied diseases. Blood, 8(11), 965–999. https://doi.org/10.1182/blood.V8.11.965.965
   PubMed Web of Science ®Google Scholar
• Chai, J.-D., & Head-Gordon, M. (2008). Long-range corrected hybrid density functionals with damped atom–atom dispersion corrections. Physical Chemistry Chemical Physics, 10(44), 6615–6620. https://doi.org/10.1039/b810189b
   PubMed Web of Science ®Google Scholar
• Chen, X., Wu, P., Rousseas, M., Okawa, D., Gartner, Z., Zettl, A., & Bertozzi, C. R. (2009). Boron nitride nanotubes are noncytotoxic and can be functionalized for interaction with proteins and cells. Journal of the American Chemical Society, 131(3), 890–891. https://doi.org/10.1021/ja807334b
   PubMed Web of Science ®Google Scholar
• El-Mageed, H. A., &Ibrahim, M. A. (2021). Elucidating the adsorption and detection of amphetamine drug by pure and doped Al12N12, and Al12P12nano-cages, a DFT study. Journal of Molecular Liquids, 326, 115297. https://doi.org/10.1016/j.molliq.2021.115297
   Web of Science ®Google Scholar
• El-Mageed, H. A., Mustafa, F. M., & Abdel-Latif, M. K. (2020). Boron nitride nanoclusters, nanoparticles and nanotubes as a drug carrier for isoniazid anti-tuberculosis drug, computational chemistry approaches. Journal of Biomolecular Structure and Dynamics, 1–10.
   PubMed Web of Science ®Google Scholar
• Eslami, M., Vahabi, V., & Peyghan, A. A. (2016). Sensing properties of BN nanotube toward carcinogenic 4-chloroaniline: A computational study. Physica E: Low-Dimensional Systems and Nanostructures, 76, 6–11. https://doi.org/10.1016/j.physe.2015.09.043
   Web of Science ®Google Scholar
• Esrafili, M. D., & Nurazar, R. (2014). A DFT study on the possibility of using boron nitride nanotubes as a dehydrogenation catalyst for methanol. Applied Surface Science, 314, 90–96. https://doi.org/10.1016/j.apsusc.2014.06.148
   Web of Science ®Google Scholar
• Farmanzadeh, D., & Keyhanian, M. (2019). Computational assessment on the interaction of amantadine drug with B12N12 and Zn12O12 nanocages and improvement in adsorption behaviors by impurity Al doping. Theoretical Chemistry Accounts, 138, 11. https://doi.org/10.1007/s00214-018-2400-3
   Web of Science ®Google Scholar
• Farzad, F., & Hashemzadeh, H. (2020). Probing the effect of polyethene glycol on the adsorption mechanisms of Gem on the hexagonal boron nitride as a highly efficient polymerbased drug delivery system: DFT, classical MD and well-tempered metadynamics simulations. Journal of Molecular Graphics and Modelling, 98, 107613. https://doi.org/10.1016/j.jmgm.2020.107613
   PubMed Web of Science ®Google Scholar
• Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Scalmani, G., Barone, V., Petersson, G. A., Nakatsuji, H., Li, X. ,Caricato, M., Marenich, A., Bloino, J. ,Janesko, B. G., Gomperts, R., Mennucci, B., Hratchian, H. P., Ortiz, J. V., … Fox, D. J. (2003). Gaussian 09, Revision A.1. Gaussian Inc.
   Google Scholar
• Ganji, M. D., Yazdani, H., & Mirnejad, A. (2010). B36N36 fullerene-like nanocages: A novel material for drug delivery. Physica E: Low-Dimensional Systems and Nanostructures, 42(9), 2184–2189. https://doi.org/10.1016/j.physe.2010.04.018
   Web of Science ®Google Scholar
• Golberg, D., Bando, Y., Stéphan, O., & Kurashima, K. (1998). Octahedral boron nitride fullerenes formed by electron beam irradiation. Applied Physics Letters, 73(17), 2441–2443. https://doi.org/10.1063/1.122475
   Web of Science ®Google Scholar
• Goldberg, D., Bando, Y., Eremets, M., Takemura, K., Kurashima, K., Tamiya, K., & Yusa, H. (1997). Boron nitride nanotube growth defects and their annealing-out under electron irradiation. Chemical Physics Letters, 279(3-4), 191–196. https://doi.org/10.1016/S0009-2614(97)00962-7
   Web of Science ®Google Scholar
• Golipour-Chobar, E., Salimi, F., & Ebrahimzadeh Rajaei, G. (2020). Boron nitride nanocluster as a carrier for lomustine anticancer drug delivery: DFT and thermodynamics studies. Monatshefte Für Chemie - Chemical Monthly, 151(3), 309–318. https://doi.org/10.1007/s00706-020-02564-y
   Google Scholar
• Hasanzade, Z., & Raissi, H. (2017). Solvent/co-solvent effects on the electronic properties and adsorption mechanism of anticancer drug thioguanine on graphene oxide surface as a nanocarrier: Density functional theory investigation and a molecular dynamics. Applied Surface Science, 422, 1030–1041. https://doi.org/10.1016/j.apsusc.2017.05.245
   Web of Science ®Google Scholar
• Hashemzadeh, H., & Raissi, H. (2019). Loading and release of anticancer drug from phosphorene as a template material with high efficient carrier: From vacuum to cell membrane. Journal of Molecular Liquids, 291, 111346. https://doi.org/10.1016/j.molliq.2019.111346
   Web of Science ®Google Scholar
• Hohenberg, P., & Kohn, W. (1964). Inhomogeneous electron gas. Physical Review, 136(3B), B864–BB71. https://doi.org/10.1103/PhysRev.136.B864
   Web of Science ®Google Scholar
• Hoseininezhad-Namin, M. S., Pargolghasemi, P., Alimohammadi, S., Rad, A. S., & Taqavi, L. (2017). Quantum Chemical Study on the adsorption of metformin drug on the surface of pristine, Si- and Al-doped (5, 5) SWCNTs. Physica E: Low-Dimensional Systems and Nanostructures, 90, 204–213. https://doi.org/10.1016/j.physe.2017.04.002
   Web of Science ®Google Scholar
• Hossain, M. R., Hasan, M. M., Nishat, M., Noor-E-Ashrafi, Ahmed, F., Ferdous, T., & Hossain, M. A. (2021). DFT and QTAIM investigations of the adsorption of chlormethine anticancer drug on the exterior surface of pristine and transition metal functionalized boron nitride fullerene. Journal of Molecular Liquids, 323, 114627. https://doi.org/10.1016/j.molliq.2020.114627
   Web of Science ®Google Scholar
• Keith, T. A. (2019). AIMAll (Version 19.02.13). TK Gristmill Software. aim.tkgristmill.com.
   Google Scholar
• Kim, K. K., Hsu, A., Jia, X., Kim, S. M., Shi, Y., Hofmann, M., Nezich, D., RodriguezNieva, J. F., Dresselhaus, M., Palacios, T., & Kong, J. (2012). Synthesis of monolayer hexagonal. Boron nitride on Cu foil using chemical vapor deposition. Nano Letters, 12, 161–166. https://doi.org/10.1021/nl203249a
   PubMed Web of Science ®Google Scholar
• Kraszewski, S., Duverger, E., Ramseyer, C., & Picaud, F. (2013). Theoretical study of amino derivatives and anticancer platinum drug grafted on various carbon nanostructures. Journal of Chemical Physics, 139(17), 1–14.
   Web of Science ®Google Scholar
• Li, J., Lu, Y., Ye, Q., Cinke, M., Han, J., & Meyyappan, M. (2003). Carbon nanotube sensors for gas and organic vapor detection. Nano Letters, 3(7), 929–933. https://doi.org/10.1021/nl034220x
   Web of Science ®Google Scholar
• Matxain, J. M., Eriksson, L. A., Mercero, J. M., Lopez, X., Piris, M., Ugalde, J. M., Poater, J., Matito, E., & Solà, M. (2007). New solids based on B12N12 fullerenes. The Journal of Physical Chemistry C, 111(36), 13354–13360. https://doi.org/10.1021/jp073773j
   Web of Science ®Google Scholar
• Mirkamali, E. S., & Ahmadi, R. (2020). Adsorption of melphalan anticancer drug on the surface of boron nitride cage (B12N12): A comprehensive DFT study. Journal of Medicinal and Chemical Sciences, 3(3), 199–207.
   Google Scholar
• Munshi, P. N., Lubin, M., & Bertino, J. R. (2014). 6-thioguanine: A drug with unrealized potential for cancer therapy. Oncologist, 19(7), 760–765. https://doi.org/10.1634/theoncologist.2014-0178
   PubMed Web of Science ®Google Scholar
• Noormohammadbeigi, M., Kamalinahad, S., Izadi, F., Adimi, M., & Ghasemkhani, A. (2020). Theoretical investigation of thioguanine isomers anticancer drug adsorption treatment on B12N12 nanocage. Materials Research Express, 6(12), 1250g2. https://doi.org/10.1088/2053-1591/ab672a
   Web of Science ®Google Scholar
• Oku, T., Narita, I., & Nishiwaki, A. (2004). Synthesis, atomic structures, and electronic states of boron nitride nanocage clusters and nanotubes. Materials and Manufacturing Processes, 19(6), 1215–1239. https://doi.org/10.1081/AMP-200035336
   Web of Science ®Google Scholar
• Padash, A., Esfahani, M. R., & Rad, A. S. (2020). The computational quantum mechanical study of sulfamide drug adsorption onto X12Y12 fullerenelikenanocages: Detailed DFT and QTAIM investigations. Journal of Biomolecular Structure and Dynamics. https://doi.org/10.1080/07391102.2020.1792991
   PubMedGoogle Scholar
• Padash, R., Sobhani Nasab, A., Rahimi Nasrabadi, M., Mirmotahari, M., Ehrlich, H., Rad, A. S., & Peyravi, M. (2018). Is it possible to use X12Y12 (X = Al, B, and Y = N, P) nanocages for drug-delivery systems? A DFT study on the adsorption property of 4-aminopyridine drug. Applied Physics A, 124(9), 582. https://doi.org/10.1007/s00339-018-1965-y
   Web of Science ®Google Scholar
• Paine, R. T., & Narula, C. K. (1990). Synthetic routes to boron nitride. Chemical Reviews, 90(1), 73–91. https://doi.org/10.1021/cr00099a004
   Web of Science ®Google Scholar
• Paek, H.-J., Lee, Y.-J., Chung, H.-E., Yoo, N.-H., Lee, J.-A., Kim, M.-K., Lee, J. K., Jeong, J., & Choi, S.-J. (2013). Modulation of the pharmacokinetics of zinc oxide nanoparticles and their fates in vivo. Nanoscale, 5(23), 11416–11427. https://doi.org/10.1039/c3nr02140h
   PubMed Web of Science ®Google Scholar
• Rad, A. S., & Ayub, K. (2016). A comparative density functional theory study of guanine chemisorption on Al12N12, Al12P12, B12N12, and B12P12 nano-cages. Journal of Alloys and Compounds, 672, 161–169.
   Web of Science ®Google Scholar
• Responsive photonic nanostructures: Smart nanoscale optical materials. n.d. Google Books. https://books.google.com.bd/books?hl=en&lr=&id=CmX2L_rJ4JoC&oi=fnd&pg=PA292&dq=D.+Golberg,+Y.+Bando,+Y.+Huang,+T.+Terao,+M.+Mitome,+C.+Tang,+C
   Google Scholar
• Saikia, N., & Deka, R. C. (2013). Ab initio study on the noncovalent adsorption of camptothecin anticancer drug onto graphene, defect modified graphene and graphene oxide. Journal of Computer-Aided Molecular Design, 27(9), 807–821. https://doi.org/10.1007/s10822-013-9681-3
   PubMed Web of Science ®Google Scholar
• Seifert, G., Fowler, P. W., Mitchell, D., Porezag, D., & Frauenheim, T. (1997). Boron-nitrogen analogues of the fullerenes: Electronic and structural properties. Chemical Physics Letters, 268(5-6), 352–358. https://doi.org/10.1016/S0009-2614(97)00214-5
   Web of Science ®Google Scholar
• Shakerzadeh, E., Khodayar, E., & Noorizadeh, S. (2016). Theoretical assessment of phosgene adsorption behavior onto pristine, Al- and Ga-doped B12N12 and B16N16 nanoclusters. Computational Materials Science, 118, 155–171. https://doi.org/10.1016/j.commatsci.2016.03.016
   Web of Science ®Google Scholar
• Sierpe, R., Noyong, M., Simon, U., Aguayoe, D., Huerta, J., Kogan, M. J., & Yutronic, N. (2017). Construction of 6-thioguanine and 6-mercaptopurine carriers based on βcyclodextrins and gold nanoparticles. Carbohydrate Polymers, 177, 22–31. https://doi.org/10.1016/j.carbpol.2017.08.102
   PubMed Web of Science ®Google Scholar
• Singla, P., Riyaz, M., Singhal, S., & Goel, N. (2016). Theoretical study of adsorption of amino acids on graphene and BN sheet in gas and aqueous phase with empirical DFT dispersion correction. Physical Chemistry Chemical Physics, 18(7), 5597–5604. https://doi.org/10.1039/C5CP07078C
   PubMed Web of Science ®Google Scholar
• Soltani, A., Baei, M. T., Tazikeh Lemeski, E., & Shahini, M. (2014). Sensitivity of BN nano-cages to caffeine andnicotine molecules. Superlattices and Microstructures, 76, 315–325. https://doi.org/10.1016/j.spmi.2014.09.031
   Web of Science ®Google Scholar
• Soltani, A., & Javan, M. B. (2015). Carbon monoxide interactions with pure and doped B11XN12 (X = Mg, Ge, Ga) nano-clusters: A theoretical study. RSC Advances, 5(110), 90621–90631. https://doi.org/10.1039/C5RA12571E
   Web of Science ®Google Scholar
• Soltani, A., Taghartapeh, M. R., Erfani-Moghadam, V., Javan, M. B., Heidari, F., Aghaei, M., & Mahon, P. J. (2018). Serine adsorption through different functionalities on the B12N12 and PtB12N12 nanocages. Materials Science and Engineering: C, 92, 216–227. https://doi.org/10.1016/j.msec.2018.06.048
   PubMed Web of Science ®Google Scholar
• Vatanparast, M., & Shariatinia, Z. (2019). Hexagonal boron nitride nanosheet as novel drug delivery system for anticancer drugs: Insights from DFT calculations and molecular dynamics simulations. Journal of Molecular Graphics and Modelling, 89, 50–59. https://doi.org/10.1016/j.jmgm.2019.02.012
   PubMed Web of Science ®Google Scholar
• Vessally, E., Esrafili, M. D., Nurazar, R., Nematollahi, P., & Bekhradnia, A. (2017). A DFT study on electronic and optical properties of aspirin-functionalized B12N12 fullerene-like nanocluster. Structural Chemistry, 28(3), 735–748. https://doi.org/10.1007/s11224-016-0858-y
   Web of Science ®Google Scholar
• Wang, Q., Sun, Q., Jena, P., & Kawazoe, Y. (2009). Potential of AlN nanostructures as hydrogen storage materials. ACS Nano, 3(3), 621–626. https://doi.org/10.1021/nn800815e
   PubMed Web of Science ®Google Scholar
• Wu, H. S., Zhang, F. Q., Xu, X. H., Zhang, C. J., & Jiao, H. (2003). Geometric and energetic aspects of aluminum nitride cages. The Journal of Physical Chemistry A, 107(1), 204–209. https://doi.org/10.1021/jp027300i
   Web of Science ®Google Scholar
• Zhu, H. Y., Schmalz, T. G., & Klein, D. J. (1997). Alternant boron nitride cages: A theoretical study. International Journal of Quantum Chemistry, 63(2), 393–401. https://doi.org/10.1002/(SICI)1097-461X(1997)63:2<393::AID-QUA10>3.0.CO;2-A
   Web of Science ®Google Scholar
• Zhu, H., Zhao, C., Cai, Q., Fu, X., & Sheykhahmad, F. R. (2020). Adsorption behavior of 5-aminosalicylic acid drug on the B12N12, AlB11N12 and GaB11N12 nanoclusters: A comparative DFT study. Inorganic Chemistry Communications, 114, 107808. https://doi.org/10.1016/j.inoche.2020.107808
   Web of Science ®Google Scholar