Citation: Sheikhi MASOOME, Shahab SIYAMAK, Alhosseini Almodarresiyeh HORA, Khaleghian MEHRNOOSH, Kumar RAKESH, Strogova ALEKSANDRA. Theoretical Study of Adsorption Behavior of Vemurafenib Drug over BNNT(5,5-9) as a Factor of Drug Delivery: a DFT Study[J]. Chinese Journal of Structural Chemistry, ;2020, 39(8): 1422-1436. doi: 10.14102/j.cnki.0254–5861.2011–2473 shu

Theoretical Study of Adsorption Behavior of Vemurafenib Drug over BNNT(5,5-9) as a Factor of Drug Delivery: a DFT Study

a.
Young Researchers and Elite Club, Gorgan Branch, Islamic Azad University, Gorgan, Iran
b.
Belarusian State University, ISEI BSU, Minsk, Republic of Belarus
c.
Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus, 13 Surganov Str., Minsk 220072, Republic of Belarus
d.
Institute of Chemistry of New Materials, National Academy of Sciences of Belarus, 36 Skarina Str., Minsk 220141, Republic of Belarus
e.
Department of Materials and Metallurgy Engineering, Meybod University, Meybod, Iran
f.
Department of Chemistry, Islamshahr Branch, Islamic Azad University, Islamshahr, Iran
g.
Department of Chemistry, MCM DAV College Kangra Himachal Pradesh 176001 (India)

Corresponding author: Sheikhi MASOOME, m.sheikhi2@gmail.com Shahab SIYAMAK, siyamak.shahab@yahoo.com
Received Date: 28 May 2019
Accepted Date: 10 June 2020

Fund Project:

Figures(7)

In this research, a density functional theory (DFT) calculation was performed for investigation adsorption behavior of the anticancer drug Vemurafenib on BNNT(5,5-9) by using the M06-2X/6-31G* level of theory in the solvent water. The electronic spectra of the Vemurafenib drug, BNNT(5,5-9) and complex BNNT(5,5-9)/Vemurafenib in solvent water were calculated by Time Dependent Density Functional Theory (TD-DFT) for the study of adsorption effect. The non-bonded interaction effects of the Vemurafenib drug with BNNT(5,5-9) on the electronic properties, natural charges and chemical shift tensors have been also detected. The results display the change in title parameters after process adsorption. According to the natural bond orbital (NBO) results, the molecule Vemurafenib and BNNT(5,5-9) play as both electron donor and acceptor at the complex BNNT(5,5-9)/Vemurafenib. On the other hand, the charge transfer occurs between the bonding, antibonding or nonbonding orbitals in two molecules drug and BNNT. As a consequence, BNNT(5,5-9) can be considered as a drug delivery system for the transportation of Vemurafenib as anticancer drug within the biological systems.
- vemurafenib,
- BNNT(5,5-9),
- DFT,
- charge transfer,
- NBO
1. [1]
  Bertrand, N.; Leroux, J. C. The journey of a drug-carrier in the body: an anatomo-physiological perspective. J. Control. Release 2012, 161, 152–163. doi: 10.1016/j.jconrel.2011.09.098
2. [2]
  Kumar, B.; Jalodia, K.; Kumar, P.; Gautam, H. K. Recent advances in nanoparticle-mediated drug delivery. J. Drug Deliv. Sci. Technol. 2017, 41, 260–268. doi: 10.1016/j.jddst.2017.07.019
3. [3]
  Wang, Y.; Wang, F.; Shen, Y.; He, Q.; Guo, S. Tumor-specific disintegratable nanohybrids containing ultrasmall inorganic nanoparticles: from design and improved properties to cancer applications. Mater. Horiz. 2018, 5, 184–205. doi: 10.1039/C7MH01071K
4. [4]
  Padma, V. D.; Jain, S. ed. Targeted Drug Delivery: Concepts and Design Advances in Delivery Science and Technology. Springer 2014.
5. [5]
  Bae, Y. H.; Mrsny, R. J.; Park, K. ed. Cancer Targeted Drug Delivery: An Elusive Dream. Springer Science & Business Media 2013.
6. [6]
  Dai, L.; Liu, J.; Luo, Z.; Li, M.; Cai, K. Tumor therapy: targeted drug delivery systems. J. Mater. Chem. B 2016, 4, 6758–6772. doi: 10.1039/C6TB01743F
7. [7]
  Bhirde, A. A.; Patel, V.; Gavard, J.; Zhang, G.; Sousa, A. A.; Masedunskas, A.; Leapman, R. D.; Weigert, R.; Gutkind, J. S.; Rusling, J. F. Targeted killing of cancer cells in vivo and in vitro with EGF-directed carbon nanotubebased drug delivery. ACS Nano 2009, 3, 307–316. doi: 10.1021/nn800551s
8. [8]
  Heister, E.; Neves, V.; Tîlmaciu, C.; Lipert, K.; Beltrán, V. S.; Coley, H. M.; Silva, S. R. P.; McFadden, J. Triplefunctionalisation of single-walled carbon nanotubes with doxorubicin, a monoclonal antibody, and a fluorescentmarker for targeted cancer therapy. Carbon 2009, 47, 2152–2160. doi: 10.1016/j.carbon.2009.03.057
9. [9]
  Raju, H. B.; Goldberg, J. L. Nanotechnology for ocular therapeutics and tissue repair. Expert Rev. Ophthalom. 2008, 3, 431–436. doi: 10.1586/17469899.3.4.431
10. [10]
  (a) https://www.curemelanoma.org (b)https://www.cancerresearchuk.org.
11. [11]
  Zhi, C.; Bando, Y.; Tang, C.; Golberg, D. Boron nitride nanotubes. Mater. Sci. Eng. R Rep. 2010, 70, 92–111. doi: 10.1016/j.mser.2010.06.004
12. [12]
  Chen, X.; Wu, P.; Rousseas, M.; Okawa, D.; Gartner, Z.; Zettl, A.; Bertozzi, C. R. Boron nitride nanotubesarenoncytotoxic and can be functionalized for interaction with proteins and cells. J. Am. Chem. Soc. 2009, 131, 890–891. doi: 10.1021/ja807334b
13. [13]
  Chen, J.; Chen, S.; Zhao, X.; Kuznetsova, L. V.; Wong, S. S.; Ojima, I. Functionalized single-walled carbonnanotubes as rationally designed vehicles for tumor-targeted drug delivery. J. American Chem. Soc. 2008, 130, 16778–16785. doi: 10.1021/ja805570f
14. [14]
  Han, W.; Bando, Y.; Kurashima, K.; Sato, T. Synthesis of boron nitride nanotubes from carbon nanotubes by a substitution reaction. Appl. Phys. Lett. 1998, 73, 3085–3087. doi: 10.1063/1.122680
15. [15]
  Terrones, M.; Romo-Herrera, J.; Cruz-Silva, E.; López-Urías, F.; Munoz-Sandoval, E.; Velázquez-Salazar, J.; Terrones, H.; Bando, Y.; Golberg, D. Pure and doped boron nitride nanotubes. Mater. Today 2007, 10, 30–38.
16. [16]
  Yang, C. K. Exploring the interaction between the boron nitride nanotube and biological molecules. Comput. Phys. Commun. 2011, 182, 39–42. doi: 10.1016/j.cpc.2010.07.040
17. [17]
  Zhao, J. X.; Ding, Y. H. Theoretical investigation of the divacancies in boron nitride nanotubes: propertiesand surface reactivity toward various adsorbates. J. Chem. Phys. 2009, 131, 014706–014712. doi: 10.1063/1.3167409
18. [18]
  (a) Chen, Y.; Zhou, J.; Campbell, S. J.; Caer, G. L. Boron nitride nanotubes: pronounced resistance to oxidation. Appl. Phys. Lett. 2004, 84, 2430–2432. (b) Cohen, M. L.; Zettl, A. The physics of boron nitride nanotubes. Phys. Today 2010, 63, 34–38.
19. [19]
  Kalay, S.; Yilmaz, Z.; Sen, O.; Emanet, M.; Kazanc, E.; Çulha, M. Synthesis of boron nitride nanotubes and their applications. Beilstein. J. Nanotech. 2015, 6, 84–102. doi: 10.3762/bjnano.6.9
20. [20]
  Mukhopadhyay, S.; Scheicher, R. H.; Pandey, R.; Karna, S. P. Sensitivity of boron nitride nanotubes toward biomolecules of different polarities. J. Phys. Chem. Lett. 2011, 2, 2442–2447. doi: 10.1021/jz2010557
21. [21]
  Sheikhi, M.; Shahab, S.; Filippovich, L.; Khaleghian, M.; Dikusar, E.; Mashayekhi, M. Interaction between new synthesized derivative of (E, E)-azomethines and BN(6, 6-7) nanotube for medical applications: Geometry optimization, molecular structure, spectroscopic (NMR, UV/Vis, excited state), FMO, MEP and HOMO-LUMO investigations. J. Mol. Struct. 2017, 1146, 881–888. doi: 10.1016/j.molstruc.2017.06.017
22. [22]
  Sheikhi, M.; Shahab, S.; Khaleghian, M.; Kumar, R. Interaction between new anti-cancer drug syndros and CNT(6, 6-6) nanotube for medical applications: geometry optimization, molecular structure, spectroscopic (NMR, UV/Vis, excited state), FMO, MEP and HOMO-LUMO investigation. Appl. Surf. Sci. 2018, 434, 504–513. doi: 10.1016/j.apsusc.2017.10.154
23. [23]
  Sheikhi, M.; Shahab, S.; Khaleghian, M.; Haji Hajikolaee, F.; Balakhanava, I.; Alnajjar, R. Adsorption properties of the molecule resveratrol on CNT(8, 0-10) nanotube: Geometry optimization, molecular structure, spectroscopic (NMR, UV/Vis, excited state), FMO, MEP and HOMO-LUMO investigations. J. Mol. Struct. 2018, 1160, 479–487. doi: 10.1016/j.molstruc.2018.01.005
24. [24]
  Sheikhi, M.; Shahab, S.; Alnajjar, R.; Ahmadianarog, M. Adsorption properties of the new anti-cancer drug alectinib on CNT(6, 6-6) nanotube: Geometry optimization, molecular structure, spectroscopic (NMR, UV/Vis, Excited State), FMO, MEP and HOMO-LUMO investigations. J. Clust. Sci. 2019, 30, 83–96. doi: 10.1007/s10876-018-1460-9
25. [25]
  Shahab, S.; Filippovich, L.; Sheikhi, M.; Kumar, R.; Dikusar, E.; Yahyaei, H.; Muravsky, A. Polarization, excited states, trans-cis properties and anisotropy of thermal and electrical conductivity of the 4-(phenyldiazenyl)aniline in PVA matrix. J. Mol. Struct. 2017, 1141, 703–709. doi: 10.1016/j.molstruc.2017.04.014
26. [26]
  Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09 Revision A02, Gaussian, Inc., Wallingford CT 2009.
27. [27]
  Frisch, A.; Nielsen, A. B.; Holder, A. J. Gauss View Users Manual, Gaussian Inc. 2000.
28. [28]
  Sheikhi, M.; Shahab, S.; Filippovich, L.; Yahyaei, H.; Dikusar, E.; Khaleghian, M. New derivatives of (E, E)-azomethines: design, quantum chemical modeling, spectroscopic (FT-IR, UV/Vis, polarization) studies, synthesis and their applications: experimental and theoretical investigations. J. Mol. Struct. 2018, 1152, 368–385. doi: 10.1016/j.molstruc.2017.09.108
29. [29]
  Shahab, S.; Sheikhi, M.; Filippovich, L.; DikusarAnatol'evich, E.; Yahyaei, H. Quantum chemical modeling of new derivatives of (E, E)-azomethines: synthesis, spectroscopic (FT-IR, UV/Vis, polarization) and thermophysical investigations. J. Mol. Struct. 2017, 1137, 335–348. doi: 10.1016/j.molstruc.2017.02.056
30. [30]
  Weinhold, F.; Landis, C. R. Neutral bond orbitals and extensions of localized. Chem. Educ. Res. Pract. Eur. 2001, 2, 91–104. doi: 10.1039/B1RP90011K
31. [31]
  Shahab, S.; Sheikhi, M.; Filippovich, L.; Khaleghian, M.; Dikusar, E.; Yahyaei, H.; Yousefzadeh Borzehandani, M. Spectroscopic studies (Geometry optimization, E → Z isomerization, UV/Vis, excited states, FT-IR, HOMO-LUMO, FMO, MEP, NBO, polarization) and anisotropy of thermal and electrical conductivityof new azomethine dyes in stretched polymer matrix. Silicon 2018, 10, 2361–2385. doi: 10.1007/s12633-018-9773-8
32. [32]
  Sheikhi, M.; Shahab, S.; Filippovich, L.; Dikusar E.; Khaleghian, M. DFT investigations (Geometry optimization, UV/Vis, FT-IR, NMR, HOMO-LUMO, FMO, MEP, NBO, excited states) and the syntheses of new pyrimidine dyes. Chin. J. Struct. Chem. 2018, 37, 1201–1222.
33. [33]
  Shahab, S.; Sheikhi, M.; Filippovich, L.; Dikusar, E.; Yahyaei, H.; Kumar, R.; Khaleghian, M. Design of geometry, synthesis, spectroscopic (FT-IR, UV/Vis, excited state, polarization) and anisotropy (thermal conductivity and electrical) properties of new synthesized derivatives of (E, E)-azomethines in colored stretched poly (vinyl alcohol) matrix. J. Mol. Struct. 2018, 1157, 536–550. doi: 10.1016/j.molstruc.2017.12.094
1. [1]
  Zhengyu Zhou , Huiqin Yao , Youlin Wu , Teng Li , Noritatsu Tsubaki , Zhiliang Jin . Synergistic Effect of Cu-Graphdiyne/Transition Bimetallic Tungstate Formed S-Scheme Heterojunction for Enhanced Photocatalytic Hydrogen Evolution. Acta Physico-Chimica Sinica, 2024, 40(10): 2312010-. doi: 10.3866/PKU.WHXB202312010
2. [2]
  Tsegaye Tadesse Tsega , Jiantao Zai , Chin Wei Lai , Xin-Hao Li , Xuefeng Qian . Earth-abundant CuFeS2 nanocrystals@graphite felt electrode for high performance aqueous polysulfide/iodide redox flow batteries. Chinese Journal of Structural Chemistry, 2024, 43(1): 100192-100192. doi: 10.1016/j.cjsc.2023.100192
3. [3]
  Chunyan Yang , Qiuyu Rong , Fengyin Shi , Menghan Cao , Guie Li , Yanjun Xin , Wen Zhang , Guangshan Zhang . Rationally designed S-scheme heterojunction of BiOCl/g-C₃N₄ for photodegradation of sulfamerazine: Mechanism insights, degradation pathways and DFT calculation. Chinese Chemical Letters, 2024, 35(12): 109767-. doi: 10.1016/j.cclet.2024.109767
4. [4]
  Run-Han Li , Tian-Yi Dang , Wei Guan , Jiang Liu , Ya-Qian Lan , Zhong-Min Su . Evolution exploration and structure prediction of Keggin-type group IVB metal-oxo clusters. Chinese Chemical Letters, 2024, 35(5): 108805-. doi: 10.1016/j.cclet.2023.108805
5. [5]
  Chaozheng He , Jia Wang , Ling Fu , Wei Wei . Nitric oxide assists nitrogen reduction reaction on 2D MBene: A theoretical study. Chinese Chemical Letters, 2024, 35(5): 109037-. doi: 10.1016/j.cclet.2023.109037
6. [6]
  Ting-Ting Huang , Jin-Fa Chen , Juan Liu , Tai-Bao Wei , Hong Yao , Bingbing Shi , Qi Lin . A novel fused bi-macrocyclic host for sensitive detection of Cr₂O₇²⁻ based on enrichment effect. Chinese Chemical Letters, 2024, 35(7): 109281-. doi: 10.1016/j.cclet.2023.109281
7. [7]
  Sanmei Wang , Yong Zhou , Hengxin Fang , Chunyang Nie , Chang Q Sun , Biao Wang . Constant-potential simulation of electrocatalytic N₂ reduction over atomic metal-N-graphene catalysts. Chinese Chemical Letters, 2025, 36(3): 110476-. doi: 10.1016/j.cclet.2024.110476
8. [8]
  Sanmei Wang , Dengxin Yan , Wenhua Zhang , Liangbing Wang . Graphene-supported isolated platinum atoms and platinum dimers for CO₂ hydrogenation: Catalytic activity and selectivity variations. Chinese Chemical Letters, 2025, 36(4): 110611-. doi: 10.1016/j.cclet.2024.110611
9. [9]
  Chen Chen , Jinzhou Zheng , Chaoqin Chu , Qinkun Xiao , Chaozheng He , Xi Fu . An effective method for generating crystal structures based on the variational autoencoder and the diffusion model. Chinese Chemical Letters, 2025, 36(4): 109739-. doi: 10.1016/j.cclet.2024.109739
10. [10]
  Fan JIA , Wenbao XU , Fangbin LIU , Haihua ZHANG , Hongbing FU . Synthesis and electroluminescence properties of Mn²⁺ doped quasi-two-dimensional perovskites (PEA)₂Pb_yMn_1-yBr₄. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1114-1122. doi: 10.11862/CJIC.20230473
11. [11]
  Yuan Teng , Zichun Zhou , Jinghua Chen , Siying Huang , Hongyan Chen , Daibin Kuang . Dual atom-bridge effect promoting interfacial charge transfer in 2D/2D Cs₃Bi₂Br₉/BiOBr epitaxial heterojunction for efficient photocatalysis. Chinese Chemical Letters, 2025, 36(2): 110430-. doi: 10.1016/j.cclet.2024.110430
12. [12]
  Dexuan Xiao , Tianyu Chen , Tianxu Zhang , Sirong Shi , Mei Zhang , Xin Qin , Yunkun Liu , Longjiang Li , Yunfeng Lin . Transdermal treatment for malignant melanoma by aptamer-modified tetrahedral framework nucleic acid delivery of vemurafenib. Chinese Chemical Letters, 2024, 35(4): 108602-. doi: 10.1016/j.cclet.2023.108602
13. [13]
  Dan-Ying Xing , Xiao-Dan Zhao , Chuan-Shu He , Bo Lai . Kinetic study and DFT calculation on the tetracycline abatement by peracetic acid. Chinese Chemical Letters, 2024, 35(9): 109436-. doi: 10.1016/j.cclet.2023.109436
14. [14]
  Yihu Ke , Shuai Wang , Fei Jin , Guangbo Liu , Zhiliang Jin , Noritatsu Tsubaki . Charge transfer optimization: Role of Cu-graphdiyne/NiCoMoO4 S-scheme heterojunction and Ohmic junction. Chinese Journal of Structural Chemistry, 2024, 43(12): 100458-100458. doi: 10.1016/j.cjsc.2024.100458
15. [15]
  Jieqiong Xu , Wenbin Chen , Shengkai Li , Qian Chen , Tao Wang , Yadong Shi , Shengyong Deng , Mingde Li , Peifa Wei , Zhuo Chen . Organic stoichiometric cocrystals with a subtle balance of charge-transfer degree and molecular stacking towards high-efficiency NIR photothermal conversion. Chinese Chemical Letters, 2024, 35(10): 109808-. doi: 10.1016/j.cclet.2024.109808
16. [16]
  Xiao Yu , Dongyue Cui , Mengmeng Wang , Zhaojin Wang , Mengzhu Wang , Deshuang Tu , Vladimir Bregadze , Changsheng Lu , Qiang Zhao , Runfeng Chen , Hong Yan . Boron cluster-based TADF emitter via through-space charge transfer enabling efficient orange-red electroluminescence. Chinese Chemical Letters, 2025, 36(3): 110520-. doi: 10.1016/j.cclet.2024.110520
17. [17]
  Xin-Tong Zhao , Jin-Zhi Guo , Wen-Liang Li , Jing-Ping Zhang , Xing-Long Wu . Two-dimensional conjugated coordination polymer monolayer as anode material for lithium-ion batteries: A DFT study. Chinese Chemical Letters, 2024, 35(6): 108715-. doi: 10.1016/j.cclet.2023.108715
18. [18]
  Huizhong Wu , Ruiheng Liang , Ge Song , Zhongzheng Hu , Xuyang Zhang , Minghua Zhou . Enhanced interfacial charge transfer on Bi metal@defective Bi₂Sn₂O₇ quantum dots towards improved full-spectrum photocatalysis: A combined experimental and theoretical investigation. Chinese Chemical Letters, 2024, 35(6): 109131-. doi: 10.1016/j.cclet.2023.109131
19. [19]
  Ying Hou , Zhen Liu , Xiaoyan Liu , Zhiwei Sun , Zenan Wang , Hong Liu , Weijia Zhou . Laser constructed vacancy-rich TiO_2-x/Ti microfiber via enhanced interfacial charge transfer for operando extraction-SERS sensing. Chinese Chemical Letters, 2024, 35(9): 109634-. doi: 10.1016/j.cclet.2024.109634
20. [20]
  Hui Liu , Xiangyang Tang , Zhuang Cheng , Yin Hu , Yan Yan , Yangze Xu , Zihan Su , Futong Liu , Ping Lu . Constructing multifunctional deep-blue emitters with weak charge transfer excited state for high-performance non-doped blue OLEDs and single-emissive-layer hybrid white OLEDs. Chinese Chemical Letters, 2024, 35(10): 109809-. doi: 10.1016/j.cclet.2024.109809

Get Citation

PDF

XML

Metrics

PDF Downloads(1)
Abstract views(321)
HTML views(4)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142