Investigation of the Adsorption Rubraca Anticancer Drug on the CNT(4,4-8) Nanotube as a Factor of Drug Delivery: A Theoretical Study Based on DFT Method

Author(s): Masoome Sheikhi*, Siyamak Shahab, Mehrnoosh Khaleghian, Mahin Ahmadianarog, Fatemeh Azarakhshi, Rakesh Kumar

Journal Name: Current Molecular Medicine

Volume 19 , Issue 7 , 2019

  Journal Home
Translate in Chinese
Become EABM
Become Reviewer
Call for Editor


Background: In the present study, the interaction between new drug Rubraca and CNT(4,4-8) nanotube by Density Functional Theory (DFT) calculations in an aqueous medium for first time have been investigated.

Method and Results: According to calculations, the intermolecular hydrogen bonds take place between active positions of the molecule Rubraca and hydrogen atoms of the nanotube that plays an important role in the stability of the complex CNT(4,4- 8)/Rubraca. The non-bonded interaction effects of the molecule Rubraca with CNT(4,4- 8) nanotube on the electronic properties, chemical shift tensors and natural charge have been also detected. The natural bond orbital (NBO) analysis suggested that the molecule Rubraca as an electron donor and the CNT(4,4-8) nanotube plays the role an electron acceptor at the complex CNT(4,4-8)/Rubraca. The electronic spectra of the Rubraca drug and the complex CNT(4,4-8)/Rubraca were also calculated by Time Dependent Density Functional Theory (TD-DFT) for the investigation of adsorption effect of the Rubraca drug over nanotube.

Conclusion: The use of CNT(4,4-8) nanotube for Rubraca delivery to the diseased cells have been established.

Keywords: Rubraca, CNT(4, 4-8) nanotube, DFT, adsorption, Electronic spectra, NBO.

Jorio A, Dresselhaus G, Dresselhaus MS. Carbon Nanotubes: Advanced topics in the synthesis, structure, properties and applications. Springer 2008.
Gruner G. Carbon nanotube transistors for biosensing applications. Anal Bioanal Chem 2006; 384: 322-35.
Baughman RH, Zakhidov AA, de Heer WA. Carbon nanotubes--the route toward applications. Science 2002; 297: 787-92.
Sinnott SB, Andrews R. Carbon nanotubes: synthesis, properties, and applications. Crit Rev Solid State Mater Sci 2001; 26: 145-249.
Prasek J, Drbohlavova J, Chomoucka J, et al. Methods for carbon nanotubes synthesis-review. J Mater Chem 2011; 21: 15872-84.
Collins PG, Arnold MS, Avouris P. Engineering carbon nanotubes and nanotube circuits using electrical breakdown. Science 2001; 292: 706-9.
Tans S, Verschueren A, Dekker C. Room-temperature transistor based on a single carbon nanotube. Nature 1998; 393: 49-52.
Baughman RH, Cui C, Zakhidov A, et al. Carbon nanotube actuators. Science 1999; 284: 1340-4.
Kong J, Franklin NR, Zhou C, et al. Nanotube Molecular Wires as Chemical Sensors. Science 2000; 287: 622-5.
Staii C, Johnson AT. DNA-decorated carbon nanotubes for chemical sensing. Nano Lett 2005; 5: 1774-8.
Ghosh S, Sood AK, Kumar N. Carbon nanotube flow sensors. Science 2003; 299: 1042-4.
Mehra NK, Palakurthi S. Interactions between carbon nanotubes and bioactives: a drug delivery perspective. Drug Discov Today 2016; 21: 585-97.
Bertrand N, Leroux JC. The journey of a drug-carrier in the body: an anatomo-physiological perspective. J Control Release 2012; 161: 152-63.
Rashid MH, Ralph SF. Carbon nanotube membranes: synthesis, properties, and future filtration applications. Nanomater 2017; 7: 99-126.
Chakrabarti M, Kiseleva R, Vertegel A, Ray SK. Carbon nanomaterials for drug delivery and cancer therapy. J Nanosci Nanotechnol 2015; 15: 5501-11.
Foldvari M. Formulating nanomedicines: focus on carbon nanotubes as novel nanoexcipients In: Key Engineering Materials Trans Tech Publ . 2010; 441: pp. 53-74.
Chen AJ, Hamon MA, Hui H, Haddon RC. Solution properties of single-walled carbon nanotubes. Science 1998; 282: 95-8.
Liu H, Bu Y, Mi Y, Wang Y. Interaction site preference between carbon nanotube and nifedipine: A combined density functional theory and classical molecular dynamics study. J Mol Struct THEOCHEM 2009; 901: 163-8.
Feazell RP, Nakayama-Ratchford N, Dai H, Lippard S. Lippard, soluble single-walled carbon nanotubes as longboat delivery systems for platinum(iv) anticancer drug design. J Am Chem Soc 2007; 129: 8438-9.
Dhar S, Liu Z, Thomale J, Dai H, Lippard SJ. Targeted single-wall carbon nanotube-mediated pt(iv) prodrug delivery using folate as a homing device. J Am Chem Soc 2008; 130: 11467-76.
Liu Z, Chen K, Davis C, et al. Drug delivery with carbon nanotubes for in vivo cancer treatment. Cancer Res 2008; 68: 6652-60.
Pastorin G, Wu W, Wieckowski S, et al. Double functionalisation of carbon nanotubes for multimodal drug delivery. Chem Commun 2006; 11: 1182-4.
Ali-Boucetta H, Al-Jamal KT, McCarthy D, Prato M, Bianco A, Kostarelos K. Multiwalled carbon nanotube–doxorubicin supramolecular complexes for cancer therapeutics. Chem Commun 2008; 4: 459-61.
Liu Z, Sun X, Nakayama-Ratchford N, Dai H. Supramolecular chemistry on water-soluble carbon nanotubes for drug loading and delivery. ACS Nano 2007; 1: 50-6.
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: 504-13.
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: 479-87.
Syed YY. Rucaparib: First Global Approval. Drugs 2017; 77: 585-92.
Plummer R, Lorigan P, Steven N, et al. A phase II study of the potent PARP inhibitor, rucaparib (PF-01367338, AG014699), with temozolomide in patients with metastatic melanoma 590 Y. Y. Syed demonstrating evidence of chemopotentiation. Cancer Chemother Pharmacol 2013; 71: 1191-9.
Jenner ZB, Sood AK, Coleman RL. Evaluation of rucaparib and companion diagnostics in the PARP inhibitor landscape for recurrent ovarian cancer therapy. Future Oncol 2016; 12: 1439-56.
Shahab S, Filippovich L, Sheikhi M, et al. 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: 703-9.
Frisch MJ, Trucks GW, Schlegel HB, et al. Gaussian 09 revision A02. Gaussian, Inc., Wallingford CT;. 2009.
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: 881-8.
Frisch A, Nielson AB, Holder AJ. GAUSSVIEW User Manual. Gaussian Inc., Pittsburgh, PA;. 2000.
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: 368-85.
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: 335-48.
Weinhold F, Landis CR. Natural bond orbitals and extensions of localized bonding concepts. Chem Educ Res Pract 2001; 2: 91-104.
Sheikhi M, Sheikh D. Quantum chemical investigations on phenyl-7,8- dihydro-[1,3]dioxolo[4,5-g]quinolin-6(5h)-one. Rev Roum Chim 2014; 59: 761-7.
Sheikhi M, Balali E, Lari H. Theoretical investigations on molecular structure, NBO, HOMO-LUMO and MEP analysis of two crystal structures of N-(2-benzoyl-phenyl) oxalyl: A DFT study. J Phys Theor Chem 2016; 13: 155-71.

Rights & PermissionsPrintExport Cite as

Article Details

Year: 2019
Published on: 01 August, 2019
Page: [473 - 486]
Pages: 14
DOI: 10.2174/1566524019666190506143152
Price: $65

Article Metrics

PDF: 28
PRC: 1